Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
Masahiro Goto Last modified date:2020.04.24

Professor / Applied Chemistry / Department of Applied Chemistry / Faculty of Engineering

1. Momoko Kitaoka, Wei Xiao, Qingliang Kong, Yoshiro Tahara, Noriho Kamiya, Masahiro Goto, A solid-in-oil nanodispersion system for transcutaneous immunotherapy of cow’s milk allergies, Pharmaceutics, 10.3390/pharmaceutics12030205, 12, 3, 2020.03, An allergy to cow’s milk proteins is the most common food allergy in infants and toddlers. Conventional oral immunotherapy for cow’s milk allergies requires hospital admission due to the risk of severe allergic reactions, including anaphylaxis. Therefore, a simpler and safer immunotherapeutic method is desirable. We examined transcutaneous immunotherapy with a solid-in-oil (S/O) system. In the S/O system, nano-sized particles of proteins are dispersed in an oil-vehicle with the assistance of nonionic surfactants. In the present study, the S/O system enhanced the skin permeation of the allergen molecule β-lactoglobulin (BLG), as compared with a control PBS solution. The patches containing BLG in the S/O nanodispersion skewed the immune response in the allergy model mice toward T helper type 1 immunity, indicating the amelioration of allergic symptoms. This effect was more pronounced when the immunomodulator resiquimod (R-848) was included in the S/O system..
2. Dani Permana, Kosuke Minamihata, Ryo Sato, Rie Wakabayashi, Masahiro Goto, Noriho Kamiya, Linear Polymerization of Protein by Sterically Controlled Enzymatic Cross-Linking with a Tyrosine-Containing Peptide Loop, ACS Omega, 10.1021/acsomega.9b04163, 5, 10, 5160-5169, 2020.03, The structure of a protein complex needs to be controlled appropriately to maximize its functions. Herein, we report the linear polymerization of bacterial alkaline phosphatase (BAP) through the site-specific cross-linking reaction catalyzed by Trametes sp. laccase (TL). We introduced a peptide loop containing a tyrosine (Y-Loop) to BAP, and the Y-Looped BAP was treated with TL. The Y-Looped BAP formed linear polymers, whereas BAP fused with a C-terminal peptide containing a tyrosine (Y-tag) showed an irregular shape after TL treatment. The sterically confined structure of the Y-Loop could be responsible for the formation of linear BAP polymers. TL-catalyzed copolymerization of Y-Looped BAP and a Y-tagged chimeric antibody-binding protein, pG2pA-Y, resulted in the formation of linear bifunctional protein copolymers that could be employed as protein probes in an enzyme-linked immunosorbent assay (ELISA). Copolymers comprising Y-Looped BAP and pG2pA-Y at a molar ratio of 100:1 exhibited the highest signal in the ELISA with 26- and 20-fold higher than a genetically fused chimeric protein, BAP-pG2pA-Y, and its polymeric form, respectively. This result revealed that the morphology of the copolymers was the most critical feature to improve the functionality of the protein polymers as detection probes, not only for immunoassays but also for other diagnostic applications..
3. Qingliang Kong, Momoko Kitaoka, Rie Wakabayashi, Yoshiro Tahara, Noriho Kamiya, Masahiro Goto, Solid-in-oil nanodispersions for transcutaneous immunotherapy of Japanese cedar pollinosis, Pharmaceutics, 10.3390/pharmaceutics12030240, 12, 3, 2020.03, Japanese cedar pollinosis (JCP) is a common affliction caused by an allergic reaction to cedar pollen and is considered a disease of national importance in Japan. Antigen-specific immunotherapy (AIT) is the only available curative treatment for JCP. However, low compliance and persistence have been reported among patients subcutaneously or sublingually administered AIT comprising a conventional antigen derived from a pollen extract. To address these issues, many research studies have focused on developing a safer, simpler, and more effective AIT for JCP. Here, we review the novel antigens that have been developed for JCP AIT, discuss their different administration routes, and present the effects of anti-allergy treatment. Then, we describe a new form of AIT called transcutaneous immunotherapy (TCIT) and its solid-in-oil (S/O) nanodispersion formulation, which is a promising antigen delivery system. Finally, we discuss the applications of S/O nanodispersions for JCP TCIT. In this context, we predict that TCIT delivery by using a S/O nanodispersion loaded with novel antigens may offer an easier, safer, and more effective treatment option for JCP patients..
4. Rahman Md Moshikur, Md Raihan Chowdhury, Rie Wakabayashi, Yoshiro Tahara, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto, Ionic liquids with N-methyl-2-pyrrolidonium cation as an enhancer for topical drug delivery
Synthesis, characterization, and skin-penetration evaluation, Journal of Molecular Liquids, 10.1016/j.molliq.2019.112166, 299, 2020.02, The development of non-toxic ionic liquid-based active pharmaceutical ingredients (IL-APIs) for effective topical drug delivery is still challenging. The properties of IL-APIs can be boosted up by selecting potential biocompatible cations. Here, we introduced N-methyl-2-pyrrolidone (NMP) as a potent biocompatible counter ion to prepare ionic liquefied drugs for topical drug delivery. The cytotoxicity of NMP cation was investigated using mammalian cell lines (HepG2, NIH3T3 and L929 cells) and compared with conventional IL-forming cations. The synthesized NMP cation has lower toxicity than that of conventional IL-forming cations. The NMP cation showed at least 3.6, 15.2 and 58.9 times lower toxicity than that of conventional imidazolium, ammonium and phosphonium cations, respectively. The synthesized NMP-based ionic liquid (NMP-IL) was characterized using 1H & 13C NMR, FT-IR, DSC and TGA. NMP-IL showed better physico-thermal stability, enhanced skin penetration, and enriched drug accumulation 2.6 times higher than that of IL [Cho][Ibu] in the target tissue. These results suggested that NMP cation based API-IL can be an effective biocompatible formulation for topical drug delivery by accumulating active drugs in the skin..
5. Amal A.M. Elgharbawy, Muhammad Moniruzzaman, Masahiro Goto, Recent advances of enzymatic reactions in ionic liquids
Part II, Biochemical Engineering Journal, 10.1016/j.bej.2019.107426, 154, 2020.02, As a biocompatible and designer solvents, ionic liquids (ILs) are extensively used for enzymatic conversion of substrates, particularly those that are insoluble or sparingly soluble in water and common organic solvents. More than a decade ago, the first-generation ILs involved in enzymatic reactions generally comprised an imidazolium cation and non-coordinating anions, such as tetrafluoroborate and hexafluorophosphate. Recently, focus has shifted to more environmentally acceptable second- and third-generation ILs comprising enzyme compatible cations (e.g., cholinium salts) and anions, such as amines and amino acids. A wide range of such ILs have been derived from readily available renewable resources and used in biocatalytic reactions. Compared with first-generation ILs, the use of enzymes in second- and third-generation ILs provides better activity and stability, and they are also attractive from both an environmental and an economic viewpoint. In this review, we report the recent advances of enzymatic reactions in second- and third-generation ILs. The intention of this review is not to cover first-generation ILs, but rather to update and overview the potential approaches developed within the last ten years for enzymatic reactions in second- and third-generation ILs..
6. Shuto Kozaka, Yoshiro Tahara, Rie Wakabayashi, Takahiro Nakata, Taro Ueda, Noriho Kamiya, Masahiro Goto, Transcutaneous Cancer Vaccine Using a Reverse Micellar Antigen Carrier, Molecular pharmaceutics, 10.1021/acs.molpharmaceut.9b01104, 17, 2, 645-655, 2020.02, Skin dendritic cells (DCs) such as Langerhans cells and dermal dendritic cells have a pivotal role in inducing antigen-specific immunity; therefore, transcutaneous cancer vaccines are a promising strategy to prophylactically prevent the onset of a variety of diseases, including cancers. The largest obstacle to delivering antigen to these skin DC subsets is the barrier function of the stratum corneum. Although reverse micellar carriers are commonly used to enhance skin permeability to hydrophilic drugs, the transcutaneous delivery of antigen, proteins, or peptides has not been achieved to date because of the large molecular weight of drugs. To achieve effective antigen delivery to skin DCs, we developed a novel strategy using a surfactant as a skin permeation enhancer in a reverse micellar carrier. In this study, glyceryl monooleate (MO) was chosen as a skin permeation enhancer, and the MO-based reverse micellar carrier enabled the successful delivery of antigen to Langerhans cells and dermal dendritic cells. Moreover, transcutaneous vaccination with the MO-based reverse micellar carrier significantly inhibited tumor growth, indicating that it is a promising vaccine platform against tumors..
7. Wataru Yoshida, Fukiko Kubota, Yuzo Baba, Spas D. Kolev, Masahiro Goto, Separation and Recovery of Scandium from Sulfate Media by Solvent Extraction and Polymer Inclusion Membranes with Amic Acid Extractants, ACS Omega, 10.1021/acsomega.9b02540, 4, 25, 21122-21130, 2019.12, We report on the separation and recovery of scandium(III) from sulfate solutions using solvent extraction and a membrane transport system utilizing newly synthesized amic acid extractants. Scandium(III) was quantitatively extracted with 50 mmol dm-3 N-[N,N-di(2-ethylhexyl)aminocarbonylmethyl]glycine (D2EHAG) or N-[N,N-di(2-ethylhexyl)aminocarbonylmethyl]phenylalanine (D2EHAF) in n-dodecane at pH 2 and easily stripped using a 0.5 mol dm-3 sulfuric acid solution. The extraction mechanisms of scandium(III) extraction with D2EHAG and D2EHAF were examined, and it was established that scandium(III) formed a 1:3 complex with both extractants (HR), that is, Sc(SO4)2 - aq + 1.5(HR)2org ⇄ Sc(SO4)R(HR)2org + H+ aq + SO4 2- aq. The equilibrium constants of extraction were evaluated to be 4.87 and 9.99 (mol dm-3)0.5 for D2EHAG and D2EHAF, respectively. D2EHAG and D2EHAF preferentially extracted scandium(III) with a high selectivity compared to common transition metal ions under high acidic conditions (0 < pH ≤ 3). In addition, scandium(III) was quantitatively transported from a feed solution into a 0.5 mol dm-3 sulfuric acid receiving solution through a polymer inclusion membrane (PIM) containing D2EHAF as a carrier. Scandium(III) was completely separated thermodynamically from nickel(II), aluminum(III), cobalt(II), manganese(II), chromium(III), calcium(II), and magnesium(II), and partially separated from iron(III) kinetically using a PIM containing D2EHAF as a carrier. The initial flux value for scandium(III) (J0,Sc = 1.9 × 10-7 mol m-2 s-1) was two times higher than that of iron(III) (J0,Fe = 9.3 × 10-8 mol m-2 s-1)..
8. Aroit T.N. Fajar, Fukiko Kubota, Mochama L. Firmansyah, Masahiro Goto, Separation of Pallaium(II) an Rhoium(III) Using a Polymer Inclusion Membrane Containing a Phosphonium-Base Ionic Liqui Carrier, Industrial and Engineering Chemistry Research, 10.1021/acs.iecr.9b05183, 58, 49, 22334-22342, 2019.12, In this stuy, we report the separation of P(II) an Rh(III) in a chlorie solution using a polymer inclusion membrane (PIM). We esigne a trioctyl(oecyl) phosphonium chlorie (P88812Cl) ionic liqui as a metal carrier for the PIM separation system. The effects of PIM composition an experimental conitions were systematically investigate. The concentrations of hyrochloric aci in the fee solution an thiourea in the receiving solution were foun to play a crucial role in the success of selective separation. Uner the optimize conitions, P(II) coul be effectively separate from Rh(III) with a 98% recovery yiel an 99% purity. We also compare the performance of our esigne carrier, P88812Cl, to that of commercially available ionic liqui trihexyl(tetraecyl) phosphonium chlorie (P66614Cl) using a 7-cycle reusability test. The P88812Cl showe a more stable performance an better urability compare with those of the commercial ionic liqui carrier..
9. Qingliang Kong, Momoko Kitaoka, Yoshiro Tahara, Rie Wakabayashi, Noriho Kamiya, Masahiro Goto, Solid-in-oil nanodispersions for intranasal vaccination
Enhancement of mucosal and systemic immune responses, International Journal of Pharmaceutics, 10.1016/j.ijpharm.2019.118777, 572, 2019.12, En masse vaccination is a promising strategy for combatting infectious diseases. Intranasal vaccination is a viable route of mass vaccination, and it could be performed easily via needle-free administration. However, it is not widely used because it tends not to evoke sufficient immunity. The aim of the present study was to improve the performance of intranasal vaccination by extending the amount of time that administered antigens remain in the nasal cavity, and enhancing immune responses via a nanocarrier-based adjuvant. A simple and safe solid-in-oil (S/O) system was investigated as a nanocarrier in intranasal vaccination. S/O nanodispersions are oil-based dispersions of antigens coated with surfactants. Because of the mucoadhesive capacities of surfactant and oil they have high potential to extend the amount of time that administered antigens remain in the nasal cavity, and can induce strong immune responses due to a nanocarrier-based adjuvant effect. In nasal absorption experiments antigens administered intranasally via S/O nanodispersions remained in the nasal cavity longer and induced strong mucosal and systemic immune responses. Histopathology analysis indicated that S/O nanodispersions did not modify the nasal epithelium or cilia, suggesting non-toxicity of the carrier. These results indicate the potential of intranasal vaccination using S/O nanodispersions for future vaccination..
10. Qingliang Kong, Kouki Higasijima, Rie Wakabayashi, Yoshiro Tahara, Momoko Kitaoka, Hiroki Obayashi, Yanting Hou, Noriho Kamiya, Masahiro Goto, Transcutaneous delivery of immunomodulating pollen extract-galactomannan conjugate by solid-in-oil nanodispersions for pollinosis immunotherapy, Pharmaceutics, 10.3390/pharmaceutics11110563, 11, 11, 2019.11, Japanese cedar pollinosis is a type I allergic disease and has already become a major public health problem in Japan. Conventional subcutaneous immunotherapy (SCIT) and sublingual immunotherapy (SLIT) cannot meet patients’ needs owing to the side effects caused by both the use of conventional whole antigen molecules in the pollen extract and the administration routes. To address these issues, a surface-modified antigen and transcutaneous administration route are introduced in this research. First, the pollen extract (PE) was conjugated to galactomannan (PE-GM) to mask immunoglobulin E (IgE)-binding epitopes in the PE to avoid side effects. Second, as a safer alternative to SCIT and SLIT, transcutaneous immunotherapy (TCIT) with a solid-in-oil (S/O) nanodispersion system carrying PE-GM was proposed. Hydrophilic PE-GM was efficiently delivered through mouse skin using S/O nanodispersions, reducing the antibody secretion and modifying the type 1 T helper (Th1)/ type 2 T helper (Th2) balance in the mouse model, thereby demonstrating the potential to alleviate Japanese cedar pollinosis..
11. Yuya Hirakawa, Hiroshi Ueda, Tetsuya Miyano, Noriho Kamiya, Masahiro Goto, New insight into transdermal drug delivery with supersaturated formulation based on co-amorphous system, International Journal of Pharmaceutics, 10.1016/j.ijpharm.2019.118582, 569, 2019.10, The objective of this study was to prepare a supersaturated formulation based on formation of a co-amorphous system of a drug and a coformer in order to enhance skin permeation. Atenolol (ATE) and urea (URE) were used as the model drug and the coformer, respectively. Thermal analysis of physical mixtures of ATE and URE showed decreases in the melting points and the formation of a co-amorphous system which was in a supercooled liquid state because of a low glass transition temperature. Supersaturated solutions of ATE and URE at different molar ratios in polyethylene glycol 400 (PEG400) were prepared. The precipitations were observed under storage at 25 °C for all formulations except for ATE-URE at 1:8 molar ratio which remained in the supersaturated state for 2 months. 1H NMR analysis confirmed the interactions between ATE and URE in PEG400. The ATE-URE supersaturated formulation showed higher permeability for mice skin than that of ATE saturated formulation, which was superior to the expected permeability from the degree of supersaturation. We concluded that co-amorphous based supersaturated formulation offers much promise for transdermal drug delivery..
12. Md Korban Ali, Rahman Md Moshikur, Rie Wakabayashi, Yoshiro Tahara, Muhammad Moniruzzaman, Noriho Kamiya, Masahiro Goto, Synthesis and characterization of choline–fatty-acid-based ionic liquids
A new biocompatible surfactant, Journal of Colloid And Interface Science, 10.1016/j.jcis.2019.04.095, 551, 72-80, 2019.09, Ionic liquid (IL)surfactants have attracted great interest as promising substitutes for conventional surfactants owing to their exceptional and favorable physico-chemical properties. However, most IL surfactants are not eco-friendly and form unstable micelles, even when using a high concentration of the surfactant. In this study, we prepared a series of halogen-free and biocompatible choline–fatty-acid-based ILs with different chain lengths and degrees of saturation, and we then investigated their micellar properties in aqueous solutions. Characterization of the synthesized surface-active ILs (SAILs)was performed by
H and C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, differential scanning calorimetry, and elemental analysis. The surface-active properties of the SAILs were investigated by tensiometry, conductometry, and dynamic light scattering measurements. The critical micelle concentration of the SAILs was found to be 2–4 times lower than those of conventional surfactants. The thermodynamic properties of micellization (ΔG 0m, ΔH 0m, and ΔS 0m)indicate that the micellization process of the SAILs is spontaneous, stable, and entropy-driven at room temperature. The cytotoxicity of the SAILs was evaluated using mammalian cell line NIH 3T3. Importantly, [Cho][Ole]shows lower toxicity than the analogous ILs with conventional surfactants. These results clearly suggest that these environmentally friendly SAILs can be used as a potential alternative to conventional ILs for various purposes, including biological applications..
13. Safrina Dyah Hardiningtyas, Seiya Nagao, Emiko Yamamoto, Nana Shirakigawa, Rie Wakabayashi, Masahiro Goto, Hiroyuki Ijima, Noriho Kamiya, A nano-sized gel-in-oil suspension for transcutaneous protein delivery, International Journal of Pharmaceutics, 10.1016/j.ijpharm.2019.118495, 567, 2019.08, We developed a new oil-based delivery system for transdermal protein delivery, a gel-in-oil (G/O) nanosuspension, where gelatin-based hydrogel was coated with hydrophobic surfactants. The high entrapment efficiency of a model protein, phycocyanin (PC), into nano-sized gelatin hydrogel particles was achieved. Spectroscopic evaluation of PC suggested that the G/O nanosuspension could retain the functional form of PC in isopropyl myristate. In vitro skin permeation studies showed that the G/O nanosuspension facilitated the delivery of PC through the stratum corneum of Yucatan micropig skin..
14. Novitri Hastuti, Rizki Fitria Darmayanti, Safrina Dyah Hardiningtyas, Kyohei Kanomata, Kenji Sonomoto, Masahiro Goto, Takuya Kitaoka, Nanocellulose from oil palm biomass to enhance microbial fermentation of butanol for bioenergy applications, BioResources, 14, 3, 6936-6957, 2019.08, Nanocellulose made by 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-catalyzed oxidation, described as TEMPO-oxidized cellulose nanofibers (TOCNs), has a high density of negative charges on its surface. Its use in microbial fermentation systems is expected to benefit microbial process stability. In particular, microbial stability is strongly required in acetone-butanol-ethanol (ABE) fermentation associated with the solvent-extraction process of butanol production. Here, TOCNs derived from oil palm empty fruit bunches pulp were added to extractive ABE fermentation media containing glucose as a main source, which can be potentially obtained from biomass by saccharification. Then, microbial fermentation was carried out using free or immobilized bacterial cells, to produce butanol from glucose. The presence of TOCNs induced higher total butanol production in broth by improving the growth environment of Clostridium saccharoperbutylacetonicum N1-4, which was used as the butanol-producing strain. Microscopic analysis revealed that the spider-web-like TOCN network helped to entrap bacterial cells in alginate beads, by ionic crosslinking of TOCNs and alginates via Ca2+ ions, to increase stability of bacterial cells in the composite gel beads. The addition of TOCNs to fermentation media had significant positive effects on the total butanol yield..
15. Md Raihan Chowdhury, Rahman Md Moshikur, Rie Wakabayashi, Yoshiro Tahara, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto, In vivo biocompatibility, pharmacokinetics, antitumor efficacy, and hypersensitivity evaluation of ionic liquid-mediated paclitaxel formulations, International Journal of Pharmaceutics, 10.1016/j.ijpharm.2019.05.020, 565, 219-226, 2019.06, In order to prevent common hypersensitivity reactions to paclitaxel injections (Taxol), we previously reported an ionic liquid-mediated paclitaxel (IL-PTX)formulation with small particle size and narrow size distribution. The preliminary work showed high PTX solubility in the IL, and the formulation demonstrated similar antitumor activity to Taxol, while inducing a smaller hypersensitivity effect in in vitro cell experiments. In this study, the stability of the IL-PTX formulation was monitored by quantitative HPLC analysis, which showed that IL-PTX was more stable at 4 °C than at room temperature. The in vivo study showed that the IL-PTX formulation could be used in a therapeutic application as a biocompatible component of a drug delivery system. To assess the in-vivo biocompatibility, IL or IL-mediated formulations were administered intravenously by maintaining physiological buffered conditions (neutral pH and isotonic salt concentration). From in vivo pharmacokinetics data, the IL-PTX formulation was found to have a similar systemic circulation time and slower elimination rate compared to cremophor EL mediated paclitaxel (CrEL-PTX). Furthermore, in vivo antitumor and hypersensitivity experiments in C57BL/6 mice revealed that IL-PTX had similar antitumor activity to CrEL-PTX, but a significantly smaller hypersensitivity effect compared with CrEL-PTX. Therefore, the IL-mediated formulation has potential to be an effective and safe drug delivery system for PTX..
16. Wahyu Ramadhan, Genki Kagawa, Yusei Hamada, Kousuke Moriyama, Rie Wakabayashi, Kosuke Minamihata, Masahiro Goto, Noriho Kamiya, Enzymatically Prepared Dual Functionalized Hydrogels with Gelatin and Heparin to Facilitate Cellular Attachment and Proliferation, ACS Applied Bio Materials, 10.1021/acsabm.9b00275, 2, 6, 2600-2609, 2019.06, Biologically active artificial scaffolds for cell seeding are developed by mimicking extracellular matrices using synthetic materials. Here, we propose a feasible approach employing biocatalysis to integrate natural components, that is, gelatin and heparin, into a synthetic scaffold, namely a polyethylene glycol (PEG)-based hydrogel. Initiation of horseradish peroxidase-mediated redox reaction enabled both hydrogel formation of tetra-thiolated PEG via disulfide linkage and incorporation of chemically thiolated gelatin (Gela-SH) and heparin (Hepa-SH) into the polymeric network. We found that the compatibility of the type of gelatin with heparin was crucial for the hydrogelation process. Alkaline-treated gelatin exhibited superior performance over acid-treated gelatin to generate dual functionality in the resultant hydrogel originating from the two natural biopolymers. The Gela-SH/Hepa-SH dual functionalized PEG-based hydrogel supported both cellular attachment and binding of basic fibroblast growth factor (bFGF) under cell culture conditions, which increased the proliferation and phenotype transformation of NIH3T3 cells cultured on the hydrogel. Inclusion of bFGF and a commercial growth factor cocktail in hydrogel matrices effectively enhanced cell spreading and confluency of both NIH3T3 cells and HUVECs, respectively, suggesting a potential method to design artificial scaffolds containing active growth factors..
17. Mari Takahara, Rie Wakabayashi, Naoki Fujimoto, Kosuke Minamihata, Masahiro Goto, Noriho Kamiya, Enzymatic Cell-Surface Decoration with Proteins using Amphiphilic Lipid-Fused Peptide Substrates, Chemistry - A European Journal, 10.1002/chem.201900370, 25, 30, 7315-7321, 2019.05, Lipid modification of proteins plays a significant role in the activation of cellular signals such as proliferation. Thus, the demand for lipidated proteins is rising. However, getting a high yield and purity of lipidated proteins has been challenging. We developed a strategy for modifying proteins with a wide variety of synthetic lipids using microbial transglutaminase (MTG), which catalyzes the cross-linking reaction between a specific glutamine (Q) in a protein and lysine (K) in the lipid-fused peptide. The synthesized lipid-G3S-MRHKGS lipid (lipid: fatty acids, tocopherol, lithocholic acid, cholesterol) was successfully conjugated to a protein fused with LLQG (Q-tagged protein) by an MTG reaction, yielding >90 % conversion of the Q-tagged protein in a lipidated form. The purified lipid–protein conjugates were used for labeling the cell membrane in vitro, resulting in best-anchoring ability of cholesterol modification. Furthermore, in situ cell-surface decoration with the protein was established in a simple manner: subjection of cells to a mixture of cholesterol-fused peptides, Q-tagged proteins and MTG..
18. Mansoor Ul Hassan Shah, Muhammad Moniruzzaman, Magaret Sivapragasam, Md Mahabubur Rahman Talukder, Suzana Bt Yusup, Masahiro Goto, A binary mixture of a biosurfactant and an ionic liquid surfactant as a green dispersant for oil spill remediation, Journal of Molecular Liquids, 10.1016/j.molliq.2019.02.049, 280, 111-119, 2019.04, Formulations based on conventional surfactants and organic solvents have been used as potential dispersants for oil-spill remediation. However, their toxicity restricts their usage in marine environments. As a low-toxicity alternative, in this article we report an oil dispersant based on a binary mixture of an ionic liquid surfactant, choline laurate ([Cho][Lau]), and a biosurfactant, lactonic sophorolipid. We investigated the micellar properties, including the critical micelle concentration, micellar interaction parameter (β), and activity coefficients (f
and f
) for the mixed surfactant system. A non-ideal and synergistic interaction between [Cho][Lau] and lactonic sophorolipid was observed. A stable oil-in-water emulsion formed at an optimal ratio of 40:60 (w/w) of [Cho][Lau] and lactonic sophorolipid. At this ratio, a dispersion effectiveness of 83% was achieved with a dispersant-to-oil ratio of 1:25 (v/v). We observed the dispersed oil droplets with an optical microscope and evaluated their size using dynamic light scattering. The droplet size decreased with increasing dispersant-to-oil ratio. We also assessed the toxicity of the binary surfactant mixture in zebra fish (Danio rerio). Based on this assessment, the mixture can be classified as non-toxic. Therefore, the mixture of [Cho][Lau] and lactonic sophorolipid is a potential alternative to conventional toxic oil-spill dispersants..
19. Daisuke Muraoka, Naohiro Seo, Tae Hayashi, Yoshiro Tahara, Keisuke Fujii, Isao Tawara, Yoshihiro Miyahara, Kana Okamori, Hideo Yagita, Seiya Imoto, Rui Yamaguchi, Mitsuhiro Komura, Satoru Miyano, Masahiro Goto, Shin Ichi Sawada, Akira Asai, Hiroaki Ikeda, Kazunari Akiyoshi, Naozumi Harada, Hiroshi Shiku, Antigen delivery targeted to tumor-associated macrophages overcomes tumor immune resistance, Journal of Clinical Investigation, 10.1172/JCI97642, 129, 3, 1278-1294, 2019.03, Immune checkpoint inhibitors and adoptive transfer of gene-engineered T cells have emerged as novel therapeutic modalities for hard-to-treat solid tumors; however, many patients are refractory to these immunotherapies, and the mechanisms underlying tumor immune resistance have not been fully elucidated. By comparing the tumor microenvironment of checkpoint inhibition–sensitive and –resistant murine solid tumors, we observed that the resistant tumors had low immunogenicity. We identified antigen presentation by CD11b + F4/80 + tumor–associated macrophages (TAMs) as a key factor correlated with immune resistance. In the resistant tumors, TAMs remained inactive and did not exert antigen-presenting activity. Targeted delivery of a long peptide antigen to TAMs by using a nano-sized hydrogel (nanogel) in the presence of a TLR agonist activated TAMs, induced their antigen-presenting activity, and thereby transformed the resistant tumors into tumors sensitive to adaptive immune responses such as adoptive transfer of tumor-specific T cell receptor–engineered T cells. These results indicate that the status and function of TAMs have a significant impact on tumor immune sensitivity and that manipulation of TAM functions would be an effective approach for improving the efficacy of immunotherapies..
20. Mochamad L. Firmansyah, Fukiko Kubota, Wataru Yoshida, Masahiro Goto, Application of a Novel Phosphonium-Based Ionic Liquid to the Separation of Platinum Group Metals from Automobile Catalyst Leach Liquor, Industrial and Engineering Chemistry Research, 10.1021/acs.iecr.8b05848, 58, 9, 3845-3852, 2019.03, The recovery of platinum group metals (PGMs) from automotive exhaust catalysts is important, and hydrometallurgical extraction is an effective approach. In the present study, a newly designed phosphonium-based ionic liquid (IL) was applied to the separation and recovery of PGMs from an automobile catalyst leach liquor in conjunction with varying pH levels. This IL, trioctyldodecyl phosphonium chloride (P8,8,8,12Cl), allows quantitative extraction of Pd(II) at any HCl concentration, with almost 80% removal of Rh(III) at 1 mol L-1 HCl after two extractions. Significant amounts of Fe(III) were extracted into the IL phase, but could be removed using 1 mol L-1 Na2SO3. The Pd(II) and Rh(III) were selectively recovered from the IL using 1 mol L-1 CS(NH2)2 and 5 mol L-1 HCl, respectively. This work therefore demonstrated the selective recovery of PGMs through optimization of various parameters and shows the significant potential of this IL with regard to recycling PGMs from leach liquor..
21. Rahman Md Moshikur, Md Raihan Chowdhury, Rie Wakabayashi, Yoshiro Tahara, Muhammad Moniruzzaman, Masahiro Goto, Ionic liquids with methotrexate moieties as a potential anticancer prodrug
Synthesis, characterization and solubility evaluation, Journal of Molecular Liquids, 10.1016/j.molliq.2019.01.063, 278, 226-233, 2019.03, The technological utility of active pharmaceutical ingredients (APIs) is enormously improved when they are converted into ionic liquids (ILs). API-ILs possess better aqueous solubility and thermal stability than that of solid-state salt or crystalline drugs. However, many such API-ILs are not biocompatible or biodegradable. In the current study, we synthesized a series of IL-APIs using methotrexate (MTX), a potential anticancer prodrug, and biocompatible IL-forming cations (choline and amino acid esters). The MTX-IL moieties were characterized through
H NMR, FTIR, p-XRD, DSC and thermogravimetric analysis. The solubility of the MTX-ILs was evaluated in simulated body fluids (phosphate-buffered saline, simulated gastric, and simulated intestinal fluids). An assessment of the in vitro antitumor activity of the MTX-ILs in a mammalian cell line (HeLa cells) was used to evaluate their cytotoxicity. The MTX-ILs showed aqueous solubility at least 5000 times higher than that of free MTX and two orders of magnitude higher compared with that of a sodium salt of MTX in both water and simulated body fluids. Importantly, a proline ethyl ester MTX prodrug showed similar solubility as the MTX sodium salt but it provided improved in vitro antitumor activity. These results clearly suggest that the newly synthesized API-ILs represent promising potential drug formulations..
22. Wataru Yoshida, Yuzo Baba, Fukiko Kubota, Spas D. Kolev, Masahiro Goto, Selective transport of scandium(III) across polymer inclusion membranes with improved stability which contain an amic acid carrier, Journal of Membrane Science, 10.1016/j.memsci.2018.11.021, 291-299, 2019.02, This paper reports on the development of a polymer inclusion membrane (PIM) for the selective separation of Sc(III) from other REM ions. A comparison is made of the performance of cellulose triacetate (CTA) based PIMs containing 2-thenoyltrifluoroacetone (HTTA), 2-ethylhexylphosphoric acid mono-2-ethylhexyl ester (PC-88A), N-[N,N-di(2-ethylhexyl) aminocarbonylmethyl]glycine (D2EHAG) or N-[N,N-di(2-ethylhexyl)aminocarbonylmethyl]phenylalanine (D2EHAF) as the carrier in the extraction of Sc(III) from its sulfuric acid/ammonium sulfate buffer solutions. The potential of the PIM containing D2EHAF for the selective separation of Sc(III) from a feed solution containing similar concentrations of Y(III), La(III), Nd(III), and Dy(III) into a 0.5 mol L−1 sulfuric acid receiving solution has been demonstrated. In addition, the newly developed PIM containing D2EHAF exhibited excellent stability in 5 cycles of extraction and back-extraction of Sc(III) with insignificant deterioration in its performance. The results obtained in this study indicate that the molecular structure of the carrier has a strong influence on membrane stability, and that the introduction of a phenyl group into the carrier molecule results in a significant stability improvement..
23. Muhamad Alif Razi, Rie Wakabayashi, Masahiro Goto, Noriho Kamiya, Self-Assembled Reduced Albumin and Glycol Chitosan Nanoparticles for Paclitaxel Delivery, Langmuir, 10.1021/acs.langmuir.8b02809, 35, 7, 2610-2618, 2019.02, Cancer continues to pose health problems for people all over the world. Nanoparticles (NPs) have emerged as a promising platform for effective cancer chemotherapy. NPs formed by the assembly of proteins and chitosan (CH) through noncovalent interactions are attracting a great deal of interest. However, the poor water solubility of CH and low stability of this kind of NP limit its practical application. Herein, the formation of reduced bovine serum albumin (rBSA) and glycol chitosan (GC) nanoparticles (rBG-NPs) stabilized by hydrophobic interactions and disulfide bonds was demonstrated for paclitaxel (PTX) delivery. The effects of the rBSA:GC mass ratio and pH on the particle size, polydispersity index (PDI), number of particles, and surface charge were evaluated. The formation mechanism and stability of the NPs were determined by compositional analysis and dynamic light scattering. Hydrophobic and electrostatic interactions were the driving forces for the formation of the rBG-NPs, and the NPs were stable under physiological conditions. PTX was successfully encapsulated into rBG-NPs with a high encapsulation efficiency (90%). PTX-loaded rBG-NPs had a particle size of 400 nm with a low PDI (0.2) and positive charge. rBG-NPs could be internalized by HeLa cells, possibly via endocytosis. An in vitro cytotoxicity study revealed that PTX-loaded rBG-NPs had anticancer activity that was lower than that of a Taxol-like formulation at 24 h but had similar activity at 48 h, possibly because of the slow release of PTX into the cells. Our study suggests that rBG-NPs could be used as a potential nanocarrier for hydrophobic drugs..
24. Shuto Kozaka, Rie Wakabayashi, Onofrio Annunziata, Milan Balaz, Masahiro Goto, Noriho Kamiya, Sergei V. Dzyuba, Effect of macromolecular crowding on the conformational behaviour of a porphyrin rotor, Journal of Photochemistry and Photobiology A: Chemistry, 10.1016/j.jphotochem.2018.10.006, 369, 115-118, 2019.01, Macromolecular crowding modulates the conformational preference of a small molecular rotor, which is used as a molecular viscometer. The shift towards the planar conformation of the porphyrin rotor was observed in the presence of increasing concentrations and sizes of polyethylene glycols. This observation highlights the differences between the behaviour of this molecular viscometer in the crowding and non-crowding types of media..
25. Safrina Dyah Hardiningtyas, Rie Wakabayashi, Ryutaro Ishiyama, Yuki Owada, Masahiro Goto, Noriho Kamiya, Enhanced potential of therapeutic applications of curcumin using solid-in-water nanodispersion technique, JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 10.1252/jcej.18we060, 52, 1, 138-143, 2019.01, Curcumin (Cur), a hydrophobic polyphenol compound, holds promising potential as an anticancer agent. However, the poor solubility in water and the low bioavailability of curcumin have limited its therapeutic applications. In this regard, we reported the formulation of curcumin using a solid-in-water (S/W) nanodispersion technique to enhance the water solubility and therapeutic activity of curcumin. This new aqueous formulation comprises simple preparation protocols: emulsification and freeze-drying for encapsulating hydrophobic biomolecules with a hydrophilic surfactant, followed by redispersion of the resultant solid complexes in an aqueous solution. Pluronics F68 and F127 were used here for the encapsulation of curcumin. Enhanced aqueous solubility of curcumin was achieved by encapsulating curcumin with a hydrophilic surfactant using the S/W nanodispersion technique. The resultant nanosized formulation had a narrow size distribution and high entrapment efficiency of curcumin. The highest loading capacity of curcumin in S/W nanodispersion was obtained with a weight ratio of curcumin to pluronic of 1: 10 for both surfactants. The release profile of the complexes was found to depend on the type of surfactant, suggesting that the selection of a proper surfactant is crucial for controlling curcumin delivery. The anticancer activity of the S/W formulation of curcumin was correlated with the drug release profiles and cellular uptake, which in turn was influenced by the hydrophobicity and chemical structure of the surfactant..
26. Dani Permana, Kosuke Minamihata, Tsuneyuki Tatsuke, Jae M. Lee, Takahiro Kusakabe, Masahiro Goto, Noriho Kamiya, Polymerization of Horseradish Peroxidase by a Laccase-Catalyzed Tyrosine Coupling Reaction, Biotechnology Journal, 10.1002/biot.201800531, 2019.01, The polymerization of proteins can create newly active and large bio-macromolecular assemblies that exhibit unique functionalities depending on the properties of the building block proteins and the protein units in polymers. Herein, the first enzymatic polymerization of horseradish peroxidase (HRP) is reported. Recombinant HRPs fused with a tyrosine-tag (Y-tag) through a flexible linker at the N- and/or C-termini are expressed in silkworm, Bombyx mori. Trametes sp. laccase (TL) is used to activate the tyrosine of Y-tagged HRPs with molecular O
to form a tyrosyl-free radical, which initiates the tyrosine coupling reaction between the HRP units. A covalent dityrosine linkage is also formed through a HRP-catalyzed self-crosslinking reaction in the presence of H
. The addition of H
in the self-polymerization of Y-tagged HRPs results in lower activity of the HRP polymers, whereas TL provides site-selectivity, mild reaction conditions and maintains the activity of the polymeric products. The cocrosslinking of Y-tagged HRPs and HRP-protein G (Y-HRP-pG) units catalyzed by TL shows a higher signal in enzyme-linked immunosorbent assay (ELISA) than the genetically pG-fused HRP, Y-HRP-pG, and its polymers. This new enzymatic polymerization of HRP promises to provide highly active and functionalized polymers for biomedical applications and diagnostics probes..
27. Wataru Yoshida, Fukiko Kubota, Riho Kono, Masahiro Goto, Selective separation and recovery of Pt(IV) from Pd(II) through an imidazolium-ionic-liquid-based supported liquid membrane, analytical sciences, 10.2116/analsci.18N020, 35, 3, 343-346, 2019.01, A supported liquid membrane (SLM) system for the selective separation of platinum(IV) from palladium(II) has been developed. The SLM was prepared using imidazolium-based IL 1-octy-3-methylimidazolium bis(trifluoromethanesulfonyl)- imide. The initial flux and separation factor of Pt(IV) from Pd(II) were found to significantly depend on the composition of the receiving solution. Based on the performance, a 0.1 mol dm
solution was selected as a suitable receiving solution. Membrane transport experiments showed that 93% of Pt(IV) can be selectively transported into the receiving solution, whereas most Pd(II) remains in the feed solution..
28. Rie Wakabayashi, Hidetoshi Kono, Shuto Kozaka, Yoshiro Tahara, Noriho Kamiya, Masahiro Goto, Transcutaneous codelivery of tumor antigen and resiquimod in solid-in-oil nanodispersions promotes antitumor immunity, ACS Biomaterials Science and Engineering, 10.1021/acsbiomaterials.9b00260, 2019.01, Cancer vaccines aim to prevent or inhibit tumor growth by inducing an immune response to tumor-associated antigens (TAAs) encoded by or present in the vaccine. Previous work has demonstrated that effective antitumor immunity can be induced using a codelivery system in which nonspecific immunostimulatory molecules are administered together with TAAs. In this study, we investigated the antitumor effects of a solid-in-oil (S/O) nanodispersion system containing a model TAA, ovalbumin (OVA), and resiquimod (R-848), a small molecular Toll-like receptor 7/8 ligand, which induces an antigen-nonspecific cellular immune response that is crucial for the efficacy of cancer vaccines. R-848 was contained in the outer oil phase of S/O nanodispersion. Analysis of OVA and R-848 permeation in mouse skin after application of an R-848 S/O nanodispersion indicated that R-848 rapidly permeated the skin and preactivated Langerhans cells, resulting in efficient uptake of OVA and migration of antigen-loaded Langerhans cells to the draining lymph nodes. Transcutaneous immunization of mice with an R-848 S/O nanodispersion inhibited the growth of E.G7-OVA tumors and prolonged mouse survival to a greater extent than did immunization with an S/O nanodispersion containing OVA alone. Consistent with this observation, antigen-specific secretion of the Th1 cytokine interferon-γand cytolytic activity were both high in splenocytes isolated from mice immunized with R-848 S/O. Our results thus demonstrate that codelivery of R-848 significantly amplified the antitumor immune response induced by antigen-containing S/O nanodispersions and further suggest that S/O nanodispersions may be effective formulations for codelivery of TAAs and R-848 in transcutaneous cancer vaccines..
29. Maha Sharaf, Wataru Yoshida, Fukiko Kubota, Masahiro Goto, A novel binary-extractant-impregnated resin for selective recovery of scandium, JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 10.1252/jcej.18we175, 52, 1, 49-55, 2019.01, Extractant-impregnated resins (EIRs) prepared from 2-ethylhexyl phosphonic acid mono-2-ethylhexyl ester (commercial name PC-88A), neodecanoic acid (Versatic 10), and XAD-7HP polymeric beads have been developed for separation and pre-concentration of scandium (Sc). The separation factors between Sc and other metal ions are very high, allowing for selective recovery of Sc from a complex metal-mixture solution. Furthermore, desorption of Sc is quantitatively achieved using 2 M sulfuric acid, which is difficult for single-extractant-impregnated resins. The adsorption behavior, kinetics, and loading capacity of the binary EIR were investigated. The good reusability of the resin was confirmed by five times repeated use in recycling operation. This binary-extractant-impregnated concept could provide a new way to develop novel ion-exchange resins for metal separation..
30. Rie Wakabayashi, Ayumi Suehiro, Masahiro Goto, Noriho Kamiya, Designer aromatic peptide amphiphiles for self-assembly and enzymatic display of proteins with morphology control, Chemical Communications, 10.1039/C8CC08163H, 55, 5, 640-643, 2019.01, We herein designed bi-functional aromatic peptide amphiphiles both self-assembling to fibrous nanomaterials and working as a substrate of microbial transglutaminase, leading to peptidyl scaffolds with different morphologies that can be enzymatically post-functionalized with proteins..
31. Magaret Sivapragasam, Muhammad Moniruzzaman, Masahiro Goto, An Overview on the Toxicological Properties of Ionic Liquids toward Microorganisms, Biotechnology Journal, 10.1002/biot.201900073, 2019.01, Ionic liquids (ILs), a class of materials with unique physicochemical properties, have been used extensively in the fields of chemical engineering, biotechnology, material sciences, pharmaceutics, and many others. Because ILs are very polar by nature, they can migrate into the environment with the possibility of inclusion in the food chain and bioaccumulation in living organisms. However, the chemical natures of ILs are not quintessentially biocompatible. Therefore, the practical uses of ILs must be preceded by suitable toxicological assessments. Among different methods, the use of microorganisms to evaluate IL toxicity provides many advantages including short generation time, rapid growth, and environmental and industrial relevance. This article reviews the recent research progress on the toxicological properties of ILs toward microorganisms and highlights the computational prediction of various toxicity models..
32. Rie Wakabayashi, Hiroki Obayashi, Ryuichiro Hashimoto, Noriho Kamiya, Masahiro Goto, Complementary interaction with peptide amphiphiles guides size-controlled assembly of small molecules for intracellular delivery, Chemical Communications, 10.1039/c9cc02473e, 55, 49, 6997-7000, 2019.01, We introduced complementary interactions between peptide amphiphiles and a small fluorescence dye to develop a programmable multi-component supramolecular assembly, and intracellular delivery of the dye was controlled by the dimensions of the co-assembly, which was manipulated by the peptide design..
33. Md Raihan Chowdhury, Rahman Md Moshikur, Rie Wakabayashi, Yoshiro Tahara, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto, Development of a novel ionic liquid-curcumin complex to enhance its solubility, stability, and activity, Chemical Communications, 10.1039/c9cc02812a, 55, 54, 7737-7740, 2019.01, We report a one-step emulsification and rapid freeze-drying process to develop a curcumin-ionic liquid (CCM-IL) complex that could be readily dispersed in water with a significantly enhanced solubility of ∼8 mg mL-1 and half-life (t1/2) of ∼260 min compared with free CCM (solubility ∼30 nM and t1/2 ∼ 20 min). This process using an IL consisting of a long chain carbon backbone as a surfactant, may provide an alternative way of enhancing the solubility of poorly water-soluble drugs..
34. Muhammad Moniruzzaman, Masahiro Goto, Ionic Liquid Pretreatment of Lignocellulosic Biomass for Enhanced Enzymatic Delignification, Advances in Biochemical Engineering/Biotechnology, 10.1007/10_2018_64, 61-77, 2019.01, Ionic liquids (ILs), a potentially attractive “green,� recyclable alternative to environmentally harmful volatile organic compounds, have been increasingly exploited as solvents and/or cosolvents and/or reagents in a wide range of applications, including pretreatment of lignocellulosic biomass for further processing. The enzymatic delignification of biomass to degrade lignin, a complex aromatic polymer, has received much attention as an environmentally friendly process for clean separation of biopolymers including cellulose and lignin. For this purpose, enzymes are generally isolated from naturally occurring fungi or genetically engineered fungi and used in an aqueous medium. However, enzymatic delignification has been found to be very slow in these conditions, sometimes taking several months for completion. In this chapter, we highlight an environmentally friendly and efficient approach for enzymatic delignification of lignocellulosic biomass using room temperature ionic liquids (ILs) as (co)solvents or/and pretreatment agents. The method comprises pretreatment of lignocellulosic biomass in IL-aqueous systems before enzymatic delignification, with the aim of overcoming the low delignification efficiency associated with low enzyme accessibility to the solid substrate and low substrate and product solubilities in aqueous systems. We believe the processes described here can play an important role in the conversion of lignocellulosic biomass—the most abundant renewable biomaterial in the world—to biomaterials, biopolymers, biofuels, bioplastics, and hydrocarbons..
35. Takafumi Hanada, Minako Iwakuma, Masahiro Goto, Multifunctional effect of the polymer extractant thiomethylbenzoxazoyl-α-methylstyrene on the extraction of Au(III), Biocontrol Science, 10.15261/serdj.26.91, 26, 2, 91-98, 2019.01, In this study, we synthesized a polymer extractant and its monomer analogue, and the multifunctional effect was investigated by comparing their extraction behavior for Au(III). To increase the affinity for gold ions, we introduced a sulfur atom into the molecular structure of the extractant as a soft donor. The extraction ability of the new extractants for gold ions was influenced by the HCl concentration in the aqueous feed solution. The multifunctional effect appeared when using the polymer extractant in the liquid–liquid extraction of gold ions. Selectivity of the extractants toward Au(III) was evaluated using a model solution generated from leaching of waste cellphones. Selectivity for Au(III) was found to be enhanced by the multifunctional effect of the polymer extractant..
36. Mochamad L. Firmansyah, Fukiko Kubota, Masahiro Goto, Selective recovery of platinum group metals from spent automotive catalysts by leaching and solvent extraction, JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 10.1252/jcej.19we093, 52, 11, 835-842, 2019.01, Platinum group metals (PGMs) play an important role in the automotive industry as key components of exhaust catalysts. Recycling of PGMs from secondary resources, such as waste products, is encouraged to ensure their sustainability. A highly efficient and environmentally benign technique for the separation of PGMs is currently required. In the present study, the recovery of PGMs from a spent automotive catalyst was investigated using the trioctyldodecyl phosphonium chloride (P8,8,8,12Cl) ionic liquid (IL) as the PGM extraction solvent. First, leaching from the catalyst was investigated. Pt and Pd are selectively extracted into undiluted P8,8,8,12Cl from the 5 mol L−1 HCl leachate containing various metals together with Pt, Pd, and Rh. Subsequently, Rh is extracted into fresh P8,8,8,12Cl from the raffinate adjusted to an appropriate HCl concentration. Mutual separation of Pt and Pd is possible by stripping processes. Some common metals co-extracted with PGMs, such as Fe, Cu, and Zn, are removed by each stripping process. Recovery of high purity Pt, Pd, and Rh is achieved by the proposed recycling process. The results demonstrate that separation using phosphonium-based ILs is useful for recycling PGMs..
37. Noriho Kamiya, Yuki Ohama, Kosuke Minamihata, Rie Wakabayashi, Masahiro Goto, Liquid Marbles as an Easy-to-Handle Compartment for Cell-Free Synthesis and In Situ Immobilization of Recombinant Proteins, Biotechnology Journal, 10.1002/biot.201800085, 13, 12, 2018.12, Liquid marble (LM), a self-standing micro-scale aqueous droplet, emerges as a micro-bioreactor in biological applications. Herein, the potential of LM as media for cell-free synthesis and simultaneous immobilization of recombinant proteins is explored. Initially, formation of hydrogel marble (HM) by using an enzymatic disulfide-based hydrogelation technique is confirmed by incorporating three components, horseradish peroxidase (HRP), a tetra-thiolated poly(ethylene glycol) derivative, and glycyl-L-tyrosine, in LM. The compatibility of the enzymatic hydrogelation with cell-free protein synthesis in LM is then validated. Although the hydrogelation reduces the level of protein synthesis in LM when compared with that in a test tube, the biosynthesis of enhanced green fluorescent protein (EGFP) is achieved. Interestingly, EGFP synthesized in LM is entrapped in the HM, and the introduction of a cysteine residue to EGFP by genetic engineering further increases the amount of protein immobilization in the hydrogel matrices. These results suggest that the cell-free synthesis and HRP-catalyzed hydrogelation can be conducted in parallel in LM, and the eventual entrapment of the key components in HM is possible. Facile recovery of macromolecular products immobilized in HM by degrading the hydrogel network under reducing conditions should lead to the design of an easy-to-handle system to screen protein functions..
38. Mari Takahara, Rie Wakabayashi, Kosuke Minamihata, Masahiro Goto, Noriho Kamiya, Design of Lipid-Protein Conjugates Using Amphiphilic Peptide Substrates of Microbial Transglutaminase, ACS Applied Bio Materials, 10.1021/acsabm.8b00271, 1, 6, 1823-1829, 2018.12, Lipid modification of proteins plays a significant role in regulating the cellular environment. Mimicking natural lipidated proteins is a key technique for assessing the function of proteins modified with lipids and also to render self-assembly of lipids to a target protein. Herein, we report a facile method of conjugating proteins with lipid-fused peptides under homogeneous physiological conditions by using the microbial transglutaminase (MTG) reaction. MTG catalyzes the cross-linking reaction between a specific glutamine (Q) in a protein and a lysine (K) in newly designed lipid-fused peptides. The water-soluble peptide substrates for lipid modification, C14-X-MRHKGS, were newly synthesized, where C14, X, and MRHKGS represent myristic acid, linker peptides composed of G, P, or S, and MTG-reactive K surrounded with basic amino acids, respectively. The MTG-mediated cross-linking reaction between a protein fused with LLQG at the C-terminus and C14-X-MRHKGS (5 molar eq) dissolved in a phosphate saline solution resulted in lipid-protein conjugates with yields of 70 to 100%. The anchoring ability of the obtained lipid-protein conjugates to cell membranes was dependent on the number of G residues in the GnS linker, suggesting that self-assembly and hydrophobicity of the GnS motif serves to enhance membrane anchoring of lipid-protein conjugates..
39. Dani Permana, Kosuke Minamihata, Masahiro Goto, Noriho Kamiya, Laccase-catalyzed bioconjugation of tyrosine-tagged functional proteins, Journal of Bioscience and Bioengineering, 10.1016/j.jbiosc.2018.05.013, 126, 5, 559-566, 2018.11, The site-specific cross-linking of functional proteins creates macromolecular assemblies that exhibit unique biochemical and/or physicochemical properties. Herein, we explored the potential of laccase as a biocatalyst for the site-specific cross-linking of tyrosine-tagged proteins. Trametes sp. laccase (TL) was selected as the cross-linking catalyst, and Escherichia coli alkaline phosphatase (BAP) and antibody-binding proteins (pG2pAs) were employed as model proteins. The protein models were genetically fused to a peptide tag containing a tyrosine residue (Y-tag) at the N- and/or C-termini. Proteins without Y-tags were used as controls. The Y-tagged proteins could be recognized by TL as macromolecular substrates, leading to the oxidative formation of protein polymers, whereas no polymerization was observed with intact BAP or pG2pA. The TL-catalyzed cross-linking of Y-tagged proteins proceeded at a relatively high pH in comparison with that of small phenolic substrates. Co-polymers of BAP and pG2pA were able to be prepared by mixing the aqueous solution of each component in the presence of TL. A combination of bis-Y-tagged pG2pA (Y-pG2pA-Y) and Y-tagged BAP (BAP-Y) yielded functional co-polymers compatible with enzyme-linked immunosorbent assay (ELISA). The detection limit of the ELISA of ovalbumin with anti-OVA IgG depended on the molar ratio of BAP-Y and Y-pG2pA-Y in the TL-catalyzed cross-linking reaction. A high molar ratio of BAP-Y to Y-pG2pA-Y (75:1) resulted in the highest absorbance in the ELISA. The results suggested that the formation of a bifunctional protein polymer with a high molar ratio of signaling unit to antibody-binding unit gave better performance in antigen detection than using lower ratios..
40. Maha Sharaf, Wataru Yoshida, Fukiko Kubota, Masahiro Goto, Selective Extraction of Scandium by a Long Alkyl Chain Carboxylic Acid/Organophosphonic Ester Binary Extractant, Solvent Extraction and Ion Exchange, 10.1080/07366299.2018.1532139, 36, 7, 647-657, 2018.11, The organophosphorus extractant 2-ethylhexylphosphonic acid mono-2-ethylhexyl ester (PC88A) is widely used for solvent extraction of rare earth elements in an acidic leaching solution, but stripping of the loaded metals is difficult because of the high affinity between the metals and the extractant. Adding 100 times the concentration of neodecanoic acid (Versatic 10) to the extractant solution reduces the extraction ability for scandium (Sc) and enables quantitative stripping of the loaded Sc with a mild acidic solution, such as a 1 M mineral acid. The loading capacity is dependent on the PC88A concentration, so PC88A is the main species responsible for Sc extraction in the binary mixture. Nuclear magnetic resonance spectroscopy (NMR) of the organic phases suggests a potential interaction between the mixed extractants through the change in the hydrogen bonding. This causes an antagonistic effect and facilitates efficient Sc stripping from the extractant solution, so this method could be used for scandium recovery in industry..
41. Mansoor Ul Hassan Shah, Magaret Sivapragasam, Muhammad Moniruzzaman, Md Mahabubur Rahman Talukder, Suzana Bt Yusup, Masahiro Goto, Aggregation behavior and antimicrobial activity of a micellar system of binary ionic liquids, Journal of Molecular Liquids, 10.1016/j.molliq.2018.06.101, 266, 568-576, 2018.09, Ionic liquid (IL) surfactants have attracted great attention as potential alternatives to conventional surfactants because of their unique tailor-made physicochemical properties. However, in most cases, the aggregations formed by single IL surfactants in aqueous media are unstable, even when using a large amount of surfactant. To address this limitation, here we investigated the aggregation behavior of binary IL surfactant micelles composed of the ILs choline oleate ([Cho][Ol]) and choline laurate ([Cho][Lau]) in aqueous media using tensiometry and dynamic light scattering measurements. Micellar and interfacial parameters including critical micelle concentration (cmc), micellar interaction parameters (β), activity coefficients (f1 and f2), surface excess concentration (Гmax), minimum surface area per molecule (Amin), and the size of surfactant aggregates were studied. In addition, various thermodynamic parameters such as the Gibbs free energy of micellization (∆Go
mic), standard Gibbs free energy of adsorption (∆Go
ad), molar free energy (Gmin), and the excess Gibbs free energy of micellization (ΔGex) were also evaluated. A non-ideal synergistic interaction was observed for the mixed IL surfactant system, which formed larger micelles (105–120 nm) compared with those formed with a single IL (86–102 nm). The formed micelles were found to be thermodynamically stable with regards to all the mole ratio of ILs system. The antimicrobial activity of the single as well of the mixed IL system against Gram-positive and -negative bacteria displayed a low toxicity profile that fell in the range of “practically harmless” (100–1000 mg L−1). The results suggested that the micellar system composed of mixed IL surfactants provides unique physical, chemical, and biological properties may offer novel opportunities for various applications such as oil dispersants..
42. Yuji Matsumoto, Atsuomi Shundo, Masashi Ohno, Nobutomo Tsuruzoe, Masahiro Goto, Keiji Tanaka, Mesoscopic Heterogeneity in Pore Size of Supramolecular Networks, Langmuir, 10.1021/acs.langmuir.8b00641, 34, 25, 7503-7508, 2018.06, There has been a considerable interest in developing new types of gels based on a network of fibrous aggregate composed of low molecular weight gelators, also known as supramolecular gels (SMGs). Unlike conventional polymer gels with chemical cross-linking, the network formation in SMGs does not involve any covalent bonds. Thus, the network in SMGs has been often regarded as homogenous or less heterogeneous in comparison with that in chemically cross-linked polymer gels. In this study, we have experimentally verified the existence of the network heterogeneity even in SMGs. The thermal motion of probe particles in SMGs, which were prepared from aqueous dispersions of gelators having a different number of peptide residues, PalGH, PalG2H, and PalG3H, was tracked. The gels were spatially heterogeneous in terms of the network pore size, as evidenced by the variation in the particle motion depending on the location, at which a particle existed. With varying particle size, it was found that the characteristic length scale of the heterogeneity was in the order of (sub)micrometers and was smaller in the order of the PalG2H, PalG3H, and PalGH gels..
43. Md Raihan Chowdhury, Rahman Md Moshikur, Rie Wakabayashi, Yoshiro Tahara, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto, Ionic-Liquid-Based Paclitaxel Preparation
A New Potential Formulation for Cancer Treatment, Molecular pharmaceutics, 10.1021/acs.molpharmaceut.8b00305, 15, 6, 2484-2488, 2018.06, Paclitaxel (PTX) injection (i.e., Taxol) has been used as an effective chemotherapeutic treatment for various cancers. However, the current Taxol formulation contains Cremophor EL, which causes hypersensitivity reactions during intravenous administration and precipitation by aqueous dilution. This communication reports the preliminary results on the ionic liquid (IL)-based PTX formulations developed to address the aforementioned issues. The formulations were composed of PTX/cholinium amino acid ILs/ethanol/Tween-80/water. A significant enhancement in the solubility of PTX was observed with considerable correlation with the density and viscosity of the ILs, and with the side chain of the amino acids used as anions in the ILs. Moreover, the formulations were stable for up to 3 months. The driving force for the stability of the formulation was hypothesized to be the involvement of different types of interactions between the IL and PTX. In vitro cytotoxicity and antitumor activity of the IL-based formulations were evaluated on HeLa cells. The IL vehicles without PTX were found to be less cytotoxic than Taxol, while both the IL-based PTX formulation and Taxol exhibited similar antitumor activity. Finally, in vitro hypersensitivity reactions were evaluated on THP-1 cells and found to be significantly lower with the IL-based formulation than Taxol. This study demonstrated that specially designed ILs could provide a potentially safer alternative to Cremophor EL as an effective PTX formulation for cancer treatment giving fewer hypersensitivity reactions..
44. Mochamad L. Firmansyah, Fukiko Kubota, Masahiro Goto, Solvent extraction of Pt(IV), Pd(II), and Rh(III) with the ionic liquid trioctyl(dodecyl) phosphonium chloride, Journal of Chemical Technology and Biotechnology, 10.1002/jctb.5544, 93, 6, 1714-1721, 2018.04, BACKGROUND: Recycling of spent platinum group metals (PGMs) has attracted much attention in order to overcome the problems associated with the low natural abundance of these resources. To recycle such metals, efficient hydrometallurgical processes are required. To improve the efficiency of these processes, we have designed a new phosphonium-based ionic liquid as an extraction solvent. This paper reports on the potential use of the ionic liquid for extraction and separation of PGMs, namely Pt(IV), Pd(II), and Rh(III). RESULTS: An ionic liquid, trioctyl(dodecyl)phosphonium chloride, P88812Cl, which was newly synthesized, showed highly efficient extraction for Pt(IV), Pd(II), and Rh(III). P88812Cl features several advantages as an extraction solvent, such as high hydrophobicity and low viscosity compared with those features of a commercial analogue, trihexyl(tetradecyl)phosphonium chloride (P66614Cl). The favorable features of our novel ionic liquid were reflected by its high extraction efficiency and low release of phosphorus from the ionic liquid into the aqueous feed solution. Stripping operations were possible, and the high reusability of the ionic liquid was confirmed. CONCLUSION: The novel ionic liquid P88812Cl is potentially useful as an extraction solvent for PGMs. Results highlight the strengths of ionic liquids and the tuneability of their properties through design of their molecular structure..
45. Rahman Md Moshikur, Md Raihan Chowdhury, Rie Wakabayashi, Yoshiro Tahara, Muhammad Moniruzzaman, Masahiro Goto, Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids, International Journal of Pharmaceutics, 10.1016/j.ijpharm.2018.05.021, 546, 1-2, 31-38, 2018.03, The technological utility of active pharmaceutical ingredients (APIs) is greatly enhanced when they are transformed into ionic liquids (ILs). API-ILs have better solubility, thermal stability, and the efficacy in topical delivery than solid or crystalline drugs. However, toxicological issue of API-ILs is the main challenge for their application in drug delivery. To address this issue, 11 amino acid esters (AAEs) were synthesized and investigated as biocompatible counter cations for the poorly water-soluble drug salicylic acid (Sal) to form Sal-ILs. The AAEs were characterized using 1H and 13C NMR, FTIR, elemental, and thermogravimetric analyses. The cytotoxicities of the AAE cations, Sal-ILs, and free Sal were investigated using mammalian cell lines (L929 and HeLa). The toxicities of the AAE cations greatly increased with inclusion of long alkyl chains, sulfur, and aromatic rings in the side groups of the cations. Ethyl esters of alanine, aspartic acid, and proline were selected as a low cytotoxic AAE. The cytotoxicities of the Sal-ILs drastically increased compared with the AAEs on incorporation of Sal into the cations, and were comparable to that of free Sal. Interestingly, the water miscibilities of the Sal-ILs were higher than that of free Sal, and the Sal-ILs were miscible with water at any ratio. A skin permeation study showed that the Sal-ILs penetrated through skin faster than the Sal sodium salt. These results suggest that AAEs could be used in biomedical applications to eliminate the use of traditional toxic solvents for transdermal delivery of poorly water-soluble drugs..
46. Safrina Dyah Hardiningtyas, Rie Wakabayashi, Momoko Kitaoka, Yoshiro Tahara, Kosuke Minamihata, Masahiro Goto, Noriho Kamiya, Mechanistic investigation of transcutaneous protein delivery using solid-in-oil nanodispersion
A case study with phycocyanin, European Journal of Pharmaceutics and Biopharmaceutics, 10.1016/j.ejpb.2018.01.020, 127, 44-50, 2018.03, Phycocyanin (PC), a water-soluble protein-chromophore complex composed of hexameric (αβ)6 subunits, has important biological functions in blue-green algae as well as pharmacological activities in biomedicine. We have previously developed a solid-in-oil (S/O) nanodispersion method to deliver biomacromolecules through the skin, although the transcutaneous mechanism has not yet been fully elucidated. To study the mechanism of transcutaneous protein delivery, we therefore enabled S/O nanodispersion by coating PC with hydrophobic surfactants and evaluated how the proteinaceous macromolecules formulated in an oil phase might permeate the skin. The extent of S/O nanodispersion of PC was dependent on the type of surfactant, suggesting that the selection of a suitable surfactant is crucial for encapsulating a large protein having a subunit structure. By measuring the intrinsic fluorescence of PC, we found that S/O nanodispersion facilitated the accumulation of PC in the stratum corneum (SC) of Yucatan micropig skin. Furthermore, after crossing the SC layer, the fluorescent recovery of PC was evident, indicating the release of the biologically active form of PC from the SC into the deeper skin layer..
47. Muhamad Alif Razi, Rie Wakabayashi, Yoshiro Tahara, Masahiro Goto, Noriho Kamiya, Genipin-stabilized caseinatehitosan nanoparticles for enhanced stability and anti-cancer activity of curcumin, Colloids and Surfaces B: Biointerfaces, 10.1016/j.colsurfb.2018.01.041, 164, 308-315, 2018.03, Nanoparticles formed by the assembly of protein and polysaccharides are of great interest for the delivery of hydrophobic molecules. Herein, the formation of genipin-crosslinked nanoparticles from caseinate (CS) and chitosan (CH) is reported for the delivery of curcumin, a polyphenolic compound from turmeric, to cells. Genipin-crosslinked CS-CH nanoparticles (G-CCNPs) having a diameter of ∼250 nm and a low polydispersity index showed excellent stability over a wide pH range, as indicated by dynamic light scattering and transmission electron microscopic measurements. Cellular uptake of curcumin loaded into G-CCNPs by HeLa cells was improved, as measured by confocal laser scanning microscopy (CLSM) and fluorescence-activated cell-sorting analysis. Cell proliferation assays indicated that G-CCNPs were nontoxic and that curcumin's anticancer activity in vitro was also improved by G-CCNPs. Stability of curcumin at neutral pH was enhanced by G-CCNPs. CLSM study revealed that G-CCNPs were poorly internalized by HeLa cells, possibly because of strong cell membrane interactions and a negative zeta potential. Overall, our results suggested that the enhanced curcumin cytotoxicity might be associated with the enhanced stability of curcumin by G-CCNPs and free curcumin released from G-CCNPs into the cell. These biocompatible NPs might be suitable carriers for enhancing curcumin's therapeutic potential..
48. Rie Wakabayashi, Masato Sakuragi, Shuto Kozaka, Yoshiro Tahara, Noriho Kamiya, Masahiro Goto, Solid-in-Oil Peptide Nanocarriers for Transcutaneous Cancer Vaccine Delivery against Melanoma, Molecular Pharmaceutics, 10.1021/acs.molpharmaceut.7b00894, 15, 3, 955-961, 2018.03, Cancer vaccines represent a prophylactic or therapeutic method of suppressing cancer by activating the adaptive immune system. The immune response is initiated by the delivery of tumor antigens to antigen presenting cells (APCs). The use of peptides as vaccine antigens is advantageous, especially in the availability and productivity of pure and defined antigens. However, their limited immunogenicity remains a major drawback, and therefore, the utilization of nanocarriers as a means of delivering antigens to target cells and/or the addition of immune stimulants have been investigated as an efficient peptide-based cancer vaccine. We have developed a solid-in-oil (S/O) nanodispersion as a transcutaneous nanocarrier for hydrophilic molecules. This system has attractive features as a peptide nanocarrier for cancer vaccines, including transcutaneous targeting of professional APCs in the skin, high encapsulation efficacy of hydrophilic molecules, and capacity for coloading with a variety of immune stimulants such as adjuvants. We therefore sought to utilize the developed S/O nanodispersion for the delivery of the tyrosine-related protein 2 peptide, TRP-2180-188, as a peptide antigen against melanoma. Transcutaneous vaccination of the S/O nanodispersion coloaded with adjuvant R-848 was associated with a significant inhibition of melanoma growth and suppression of lung metastasis in tumor-bearing mice. Our findings indicate the potential of S/O nanodispersions as an endogenous peptide carrier for cancer vaccines..
49. Maha Sharaf, Wataru Yoshida, Fukiko Kubota, Spas D. Kolev, Masahiro Goto, A polymer inclusion membrane composed of the binary carrier PC-88A and Versatic 10 for the selective separation and recovery of Sc, RSC Advances, 10.1039/c7ra12697b, 8, 16, 8631-8637, 2018.01, This study reports on the selective separation of scandium (Sc) from other rare earth metals (REMs) using a polymer inclusion membrane (PIM). The PIM prepared with PC-88A (2-ethylhexyl hydrogen-2-ethylhexylphosphonate) alone as the carrier showed high extractability but the poor back-extraction of the extracted Sc3+ ions did not allow the transport of these ions to the receiving solution of a membrane transport system. To overcome this problem, a novel approach was introduced using a mixture of carriers that allowed Sc3+ transport into the receiving solution. A cellulose triacetate (CTA) based PIM containing both PC-88A and Versatic 10 (decanoic acid) as carriers and dioctyl phthalate (DOP) as a plasticizer was prepared for the selective separation of Sc3+ from other REM ions in nitrate media. The membrane composition was optimized and the effect of operational parameters such as pH of the feed solution and composition of the receiving solution was explored. The flux at the membrane/feed solution interface was found to depend significantly on the carrier concentration in the PIM, pH of the feed solution and the receiving solution acidity. The newly developed PIM allowed quantitative and selective transport of Sc3+ thus demonstrating its suitability for the selective recovery of this metal..
50. M. Moniruzzaman, H. Mahmood, Masahiro Goto, Ionic Liquid Based Nanocarriers for Topical and Transdermal Drug Delivery, Ionic Liquid Devices, 10.1039/9781788011839-00390, 390-403, 2018.01, In the pharmaceutical industry, there are challenges in topical and transdermal administration of drugs, which are sparingly soluble in water and most organic solvents. Ionic liquids (ILs) have been found to be very effective for dissolution of sparingly soluble drugs. However, hydrophilic IL-borne drugs cannot penetrate into or across the skin because of the highly hydrophobic barrier function of the outer skin. In this chapter we report a novel IL-in-oil (IL/o) microemulsion (ME) that is able to dissolve a significant amount of sparingly soluble drug, acyclovir, in the IL core while the continuous oil phase can provide the desired features for topical/transdermal transport through the skin. The ME is composed of a blend of the nonionic surfactants polyoxyethylene sorbitan monooleate (Tween 80) and sorbitan laurate (Span 20), isopropyl myristate (IPM) as an oil phase, and the IL [C1mim][(MeO)2PO2] (dimethylimidazolium dimethylphosphate) as a dispersed phase. The size and size distribution of the aggregates in the MEs were characterized by dynamic light scattering, showing formation of the nanocarrier in the size range 8-34 nm. In vitro drug permeation studies into and across the skin showed that the IL/o ME increased drug administration compared with other formulations. The safety profile of the new carrier was evaluated using a cytotoxicity assay on the human epidermal model LabCyte. We believe that these IL-assisted nonaqueous MEs can serve as a versatile and efficient nanodelivery system for sparingly soluble drug molecules..
51. Fukiko Kubota, Riho Kono, Wataru Yoshida, Maha Sharaf, Spas D. Kolev, Masahiro Goto, Recovery of gold ions from discarded mobile phone leachate by solvent extraction and polymer inclusion membrane (PIM) based separation using an amic acid extractant, Separation and Purification Technology, 10.1016/j.seppur.2018.04.031, 2018.01, This paper reports on the selective separation and recovery of gold ions from leachates of discarded mobile phones using liquid-liquid extraction and a polymer inclusion membrane (PIM) transport system. The collected mobile phones were crushed by a mill and the obtained powder was calcinated. After leaching with aqua regia, the metal composition of the leachate was analyzed by inductively coupled plasma atomic emission spectrometry (ICP-AES). The analysis results confirmed that the mobile phone waste contained 397 g/ton of gold. Liquid-liquid extraction and PIM-based separation procedures for the selective recovery of gold(III) from synthetic and actual leachates were developed. The extracting organic solution and the PIM incorporated the newly synthesized extractant N-[N,N-di(2-ethylhexyl)aminocarbonylmethyl]glycine (D2EHAG) which exhibited high selectivity for the gold(III) ion over the other metal ions present in much higher concentrations in the leachates. The compositions of the feed and receiving solutions in both the liquid-liquid and PIM based extraction and back-extraction of the gold(III) ions were optimized. It was established that optimal extraction required a HCl concentration in the feed solution of 2 mol/L and that a receiving solution containing 0.1 M thiourea in 1 M HCl was capable of back-extracting gold(III) quantitatively. Membrane transport experiments with a synthetic leachate as the feed solution demonstrated that 96% of the gold(III) ions was selectively transported into the receiving solution of the transport cell thus leaving all other metal ions in the leachate..
52. Takahiko Kakoi, Kanako Muranaga, Masahiro Goto, Extraction of rhodium by liquid surfactant membranes containing ionic liquid as a carrier from hydrochloric acid solutions, JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 10.1252/jcej.18we086, 51, 11, 917-920, 2018.01, Extraction behavior of rhodium (III) with a liquid surfactant membrane (LSM) containing an ionic liquid, 1-octyl-3-me-thylimidazolium hexafluorophosphate ([Omim][PF
]), as a carrier from hydrochloric acid solutions has been investigated. At the optimum conditions, rhodium was selectively extracted over tin by using LSMs in which [Omim][PF
] acted as the mobile carrier. The effects of important operational parameters on the recovery of rhodium were examined with three different stripping reagents for LSMs. It was found that the use of 2-amino-2- hydroxymethyl-1,3-propanediol (Tris) as a stripping reagent in LSMs was the key for the effective extraction of rhodium..
53. Muhamad Alif Razi, Rie Wakabayashi, Masahiro Goto, Noriho Kamiya, Formation and characterization of caseinate-chitosan nanocomplexes for encapsulation of Curcumin, JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 10.1252/jcej.17we293, 51, 5, 445-453, 2018.01, Curcumin holds promise as a therapeutic agent due to its capability of conferring several pharmacological activities. While curcumin shows efficacy in preclinical studies as an anti-cancer agent, its translation into the clinic as a drug has yet to be realized. One possible reason is its poor solubility and stability in water, which decreases the bioavailability. Here, we report the formation of biocompatible nanocomplexes (NCs) from caseinate (CS) and chitosan (CH) using an electrostatic interaction-based approach to stabilize and enhance water solubility of curcumin. The formation of CS-CH NCs (CCNCs) was studied as a function of CH concentration. We show that positively charged NCs, having size between approx. 250 nm with a narrow distribution was formed by adjusting CH concentration. CCNCs successfully entrapped curcumin with a high entrapment efficiency. Curcumin was possibly located in a hydrophobic region of CS as indicated by a blue-shift in the emission maxima of curcumin. Ultimately, the stability and water solubility of curcumin in CCNCs could be remarkably enhanced. These results suggest that CCNCs would be useful for increasing the potential of curcumin as a preventive or therapeutic agent..
54. Yoshiro Tahara, Masahiro Goto, Recent advances of ionic liquids for transdermal drug delivery systems, Drug Delivery System, 10.2745/dds.33.303, 33, 4, 303-310, 2018.01, Pharmaceutical application of ionic liquids (ILs), which are commonly defined as salt compounds composed of ionic species and melt below 100℃, is an attractive research field in a drug delivery system (DDS). The solubilization ability for insoluble drug molecules is a promising property of ILs. In 2010, it was reported that acyclovir, a sparingly soluble drug, was dissolved in imidazolium-based ILs, and the IL-in-oil microemulsions enhanced the transdermal delivery of acyclovir. The transdermal delivery is the most studied DDS field using ILs and some hydrophobic ILs were confirmed as skin penetration enhancers due to its higher interaction with the hydrophobic skin surface barrier. Utilization of active pharmaceutical ingredients (API) as the ions of ILs is known as an alternative strategy of IL-based DDSs because the API-IL enables to tune their physical or chemical properties of ILs. To improve the transdermal delivery, drugs were robed with hydrophobic counter ions. Recently, biocompatibility has been regarded as one of the most important properties of ILs for the DDS application. Several biomolecule-derived ions such as choline and amino acids were reported to form ILs and the biocompatible ILs were used as a solvent for solubilizing poorly soluble drugs and skin penetration enhancers. These researches suggest that ILs would be a promising solvent for developing a novel DDS..
55. Mari Takahara, Rie Wakabayashi, Kosuke Minamihata, Masahiro Goto, Noriho Kamiya, Primary Amine-Clustered DNA Aptamer for DNA-Protein Conjugation Catalyzed by Microbial Transglutaminase, Bioconjugate Chemistry, 10.1021/acs.bioconjchem.7b00594, 28, 12, 2954-2961, 2017.12, DNA-protein conjugates are promising biomolecules for use in areas ranging from therapeutics to analysis because of the dual functionalities of DNA and protein. Conjugation requires site-specific and efficient covalent bond formation without impairing the activity of both biomolecules. Herein, we have focused on the use of a microbial transglutaminase (MTG) that catalyzes the cross-linking reaction between a glutamine residue and a primary amine. In a model bioconjugation, a highly MTG-reactive Gln (Q)-donor peptide (FYPLQMRG, FQ) was fused to enhanced green fluorescent protein (FQ-EGFP) and a primary amine-clustered DNA aptamer was enzymatically synthesized as a novel acyl-acceptor substrate of MTG, whose combination leads to efficient and convenient preparation of DNA-protein conjugates with high purity. Dual functionality of the obtained DNA-EGFP conjugate was evaluated by discrimination of cancer cells via c-Met receptor recognition ability of the DNA aptamer. The DNA aptamer-EGFP conjugate only showed fluorescence toward cells with c-Met overexpression, indicating the retention of the biochemical properties of the DNA and EGFP in the conjugated form..
56. Momoko Kitaoka, Masahiro Goto, Related topic
Solid-in-oil technique to increase skin permeation, Skin Permeation and Disposition of Therapeutic and Cosmeceutical Compounds, 10.1007/978-4-431-56526-0_18, 225-232, 2017.11, Solid-in-oil (S/O) nanodispersion systems represent a new technology that has been developed in the last decade. Nano-sized, solid-state, hydrophilic drug molecules can be dispersed in an oil vehicle by coating the drug with hydrophobic surfactants; these materials are designated here as S/O nanodispersions. Conventional S/O nanodispersion systems were devised to maintain hydrophilic enzymes in their active form in organic solvents. Because the coated molecules are stable in non-aqueous media, S/O nanodispersion systems can be successfully applied in oral and skin drug deliveries. It is known that the permeability of hydrophilic drugs through the skin decreases when the molecular weight of the drug exceeds 500 Da. In addition, hydrophobic molecules tend to permeate through the skin preferentially, compared with hydrophilic molecules, because the outermost layer of the skin is hydrophobic. In our experiments, the permeation of hydrophilic biomolecules such as peptides and proteins through the skin increased by 4-7 times when their molecules were coated with lipophilic surfactants and dispersed in an oil vehicle. Here, we introduce an efficient method for drug delivery through the skin, using the S/O nanodispersion technique..
57. Meysam Lotfi, Muhammad Moniruzzaman, Magaret Sivapragasam, Shalini Kandasamy, M. I. Abdul Mutalib, Noorjahan Banu Alitheen, Masahiro Goto, Solubility of acyclovir in nontoxic and biodegradable ionic liquids
COSMO-RS prediction and experimental verification, Journal of Molecular Liquids, 10.1016/j.molliq.2017.08.020, 243, 124-131, 2017.10, The pharmaceutical industry faces a challenge to find potential solvents for drug molecules that are sparingly soluble in water and conventional organic solvents. Recently, ionic liquids (ILs) have attracted great attention as pharmaceutical solvents owing to their unique physicochemical and biological properties. In this study, the solubility of the sparingly soluble drug molecule acyclovir (ACV) in a wide variety of ILs was investigated by conductor-like screening model for real solvents (COSMO-RS) calculations. The predicted solubilities were validated by experimental measurements, and good agreement was found between the predicted and experimental results. The solubility of ACV was greatly affected by the structure of ILs, particularly the anionic moiety. Among the various ILs tested, ACV showed excellent solubility in ammonium-based ILs with an acetate anion. In vitro cytotoxicity of ILs to the MCF-10 normal breast epithelial cell line and cancer cell lines (MDA MB 231 and MCF 7) was investigated. The ammonium-based ILs showed higher IC50 values than the imidazolium-based ILs with the acetate anion. Biodegradability results showed that diethylammonium acetate, triethylammonium acetate, and choline acetate ILs have high levels of biodegradation under aerobic conditions and can be classified as readily biodegradable. These findings will be useful for the design of IL-based drug delivery carriers that can act as versatile and efficient drug delivery systems for sparingly soluble drug molecules..
58. Qingliang Kong, Momoko Kitaoka, Rie Wakabayashi, Noriho Kamiya, Masahiro Goto, Transcutaneous immunotherapy of pollinosis using solid-in-oil nanodispersions loaded with T cell epitope peptides, International Journal of Pharmaceutics, 10.1016/j.ijpharm.2017.07.020, 529, 1-2, 401-409, 2017.08, Pollinosis, a typical seasonal allergy, is a serious public health problem. Limited numbers of patients receive curative immunotherapy instead of symptomatic therapy; however, there are still some concerns about the inconvenience and side effects of subcutaneous injections and sublingual administration caused by immunotherapy. Here, we propose a simple and safe transcutaneous immunotherapy using solid-in-oil (S/O) nanodispersions loaded with vaccine T cell epitope peptides derived from pollen allergen. S/O nanodispersions are oil-based dispersions of antigens coated with hydrophobic surfactants. They have a high potential to deliver biomolecules including peptides or proteins to immune cells in the skin, and to induce an immune response. The result of quantitative and qualitative analysis by in vitro permeation experiments demonstrated the effective permeation of T cell epitope peptides into the skin. Furthermore, in vivo experiments using a pollinosis mouse model indicated that the S/O nanodispersions loaded with T cell epitopes suppressed serum antibody IgE and cytokine production, and alleviated allergic symptoms to a similar therapeutic level to that observed for subcutaneous injection. These results indicate the potential of transcutaneous immunotherapy using S/O nanodispersions for the future treatment of pollinosis..
59. M. Takano, Y. Ozaki, S. Asano, Y. Baba, F. Kubota, M. Goto, Separation of Cobalt by Solvent Extraction Using Oxide-Amine Mixture System, J. MMIJ., 136, 8, 188-192, 2017.08.
60. Wataru Yoshida, Yuzo Baba, Fukiko Kubota, Noriho Kamiya, Masahiro Goto, Extraction and stripping behavior of platinum group metals using an amic-acid-type extractant, Journal of Chemical Engineering of Japan, 10.1252/jcej.16we335, 50, 7, 521-526, 2017.07, The recovery and separation of platinum group metals (PGMs) are of considerable significance for metal sustainability. To establish an efficient extraction process for PGMs, the novel extractant N-[N,N-di(2-ethylhexyl)aminocarbonylmethyl] phenylalanine (D2EHAF), containing a phenylalanine moiety as the metal-affinity group, was synthesized. The extraction of PGMs from aqueous HCl and HNO3 solutions with D2EHAF, or our previously developed N-[N,N-di(2-ethylhexyl) aminocarbonylmethyl]glycine (D2EHAG), in n-dodecane was investigated. Both D2EHAF and D2EHAG exhibited high extraction affinities for Os4+, Pt4+, and Pd2+ in aqueous HCl. In a HNO3 solution, D2EHAF extracted Pd2+ more efficiently than D2EHAG, and the extraction of Pd2+ from a 1 mol dm-3 HNO3 solution with D2EHAF proceeded quantitatively. The extracted metal ions were stripped from the organic solution using a highly acidic solution, or thiourea..
61. Fukiko Kubota, Eiko Shigyo, Wataru Yoshida, Masahiro Goto, Extraction and separation of Pt and Pd by an imidazolium-based ionic liquid combined with phosphonium chloride, Solvent Extraction Research and Development, 10.15261/serdj.24.97, 24, 2, 97-104, 2017.05, Extraction and separation of Pt(IV) and Pd(II) from a hydrochloric acid solution was examined with a mixture of undiluted ionic liquids, 1-methyl-3-octylimidazolium bis(trifluoromethylsulfonyl)imide ([C8mim][Tf2N]) and trihexyltetradecylphosphonium chloride ([P6,6,6,14][Cl]). Imidazolium-based [C8mim][Tf2N] shows a high selectivity for Pt(VI), whereas [P6,6,6,14][Cl] has a high extraction ability for both Pt(IV) and Pd(II). The addition of [P6,6,6,14][Cl] to [C8mim][Tf2N] improved the extraction efficiency for Pt and the separation factor between Pt and Pd also increased. This improvement was attributed to the presence of Cl- being more hydrophilic than Tf2N- in the [C8mim][Tf2N] extraction phase. Stripping of the metals was possible with HNO3 solution without any degradation of the ionic liquid extraction phase. The ionic liquid mixture was shown to be reusable for at least five extraction cycles..
62. Momoko Kitaoka, Masahiro Goto, Transcutaneous pollinosis immunotherapy using a solid-in-oil nanodispersion system carrying T cell epitope peptide and R848, Bioengineering & Translational Medicine, 10.1002/btm2.10048, 2, 1, 102-108, 2017.04.
63. Yuji Matsumoto, Atsuomi Shundo, Masashi Ohno, Nobutomo Tsuruzoe, Masahiro Goto, Keiji Tanaka, Evolution of heterogeneity accompanying sol-gel transitions in a supramolecular hydrogel, Soft Matter, 10.1039/c7sm01612c, 13, 40, 7433-7440, 2017.04, When a peptide amphiphile is dispersed in water, it self-assembles into a fibrous network, leading to a supramolecular hydrogel. When the gel is physically disrupted by shaking, it transforms into a sol state. After aging at room temperature for a while, it spontaneously returns to the gel state, called sol-gel transition. However, repeating the sol-gel transition often causes a change in the rheological properties of the gel. To gain a better understanding of the sol-gel transition and its reversibility, we herein examined the thermal motion of probe particles at different locations in a supramolecular hydrogel. The sol obtained by shaking the gel was heterogeneous in terms of the rheological properties and the extent decreased with increasing aging time. This time course of heterogeneity, or homogeneity, which corresponded to the sol-to-gel transition, was observed for the 1st cycle. However, this was not the case for the 2nd and 3rd cycles; the heterogeneity was preserved even after aging. Fourier-transform infrared spectroscopy, small-angle X-ray scattering, and atomic force and confocal laser scanning microscopies revealed that, although the molecular aggregation states of amphiphiles both in the gel and sol remained unchanged with the cycles, the fibril density diversified to high and low density regions even after aging. The tracking of particles with different sizes indicated that the partial mesh size in the high density region and the characteristic length scale of the density fluctuation were smaller than 50 nm and 6 μm, respectively..
64. Mansoor Ul Hassan Shah, Magaret Sivapragasam, Muhammad Moniruzzaman, Md Mahabubur Rahman Talukder, Suzana Bt Yusup, Masahiro Goto, Production of sophorolipids by Starmerella bombicola yeast using new hydrophobic substrates, Biochemical Engineering Journal, 10.1016/j.bej.2017.08.005, 127, 60-67, 2017.04, Sophorolipids (SLs) are surface active compounds that have excellent surface-lowering properties. Typically, SLs are produced using different hydrophobic substrates, such as alkanes, vegetable oils, and industrial effluents. The properties of the SLs are highly dependent on the hydrophobic substrate used for their production. The aim of the present study is to investigate the properties of SLs produced using three new hydrophobic substrates: Tapis oil, Melita oil, and Ratawi oil. The structures of the SLs were determined by Fourier transform infrared spectroscopy. The SLs yields using Tapis, Melita, and Ratawi oil were 26, 21, and 19 g L−1, respectively. The SLs produced using Tapis, Melita, and Ratawi oil reduced the surface tension of pure water to 36.38, 37.84, and 38.92 mN/m, respectively, corresponding to critical micelle concentrations (CMCs) of 54.39, 55.68, and 58.34 mg L−1. These values are comparable with SLs produced using palm oil (surface tension 35.38 mN/m and CMC 48.76 mg L−1). The SLs produced using Tapis oil show a maximum emulsification activity of 71.2%. The produced SLs are active over the pH range 2–10 and for salinity up to 20% (w/v) NaCl. Thus, they show potential for various applications, including microbial enhanced oil recovery and oil spill remediation..
65. Yoshiro Tahara, Masahiro Goto, Transdermal protein delivery and immunization by a solid-in-oil nanodispersion technique, Drug Delivery System, 10.2745/dds.32.176, 32, 3, 176-183, 2017.04, Transcutaneous vaccination is an attractive strategy that delivers antigen molecules topically into the skin to induce protective or therapeutic immune responses. In the last two decades, the skin has been regarded as a potential administration site for vaccines due to the abundant antigen presenting cells in the skin such as Langerhans cells and dermal dendritic cells, which are found in the epidermis or dermis. To create an efficient transcutaneous vaccine, the antigen needs to be penetrated across the stratum corneum, which is the outermost layer of the skin and possesses a high barrier function. To overcome this issue, various types of drug delivery systems have been proposed such as ultrasound, jet immunization and microneedles as physical methods, and penetration peptides, liposomes and nanoparticles as chemical methods. In this review, a solid-in-oil (S/O) nanodispersion, which is an oil-based drug carrier for proteins and peptides, and its application for transcutaneous protein delivery and vaccination are summarized. Along with comparing the S/O nanodispersion with the other oil-based drug carriers, the transdermal delivery of proteins such as insulin is introduced. Finally, basic immunological responses via transcutaneous administration with the S/O nanodispersion containing a model antigen, and researches on protect and therapeutic applications are summarized..
66. Rie Wakabayashi, Masahiro Goto, Norah Kamiya, Protein-Grafted Polymers Prepared Through a Site-Specific Conjugation by Microbial Transglutaminase for an Immunosorbent Assay, BIOMACROMOLECULES, 10.1021/acs.biomac.6b01538, 18, 2, 422-430, 2017.02.
67. Rie Wakabayashi, Kensuke Yahiro, Kounosuke Hayashi, Masahiro Goto, Noriho Kamiya, Protein-Grafted Polymers Prepared Through a Site-Specific Conjugation by Microbial Transglutaminase for an Immunosorbent Assay, Biomacromolecules, 10.1021/acs.biomac.6b01538, 18, 2, 422-430, 2017.02, Protein-polymer conjugates have been developed in many fields. Most hybrids are composed of one protein attached to one or several polymer chains. The other form of hybrid involves the construction of multiple proteins on one polymer chain, thereby facilitating protein assemblies that provide multivalent effects. Unfortunately, synthetic methods for production of these types of hybrids are limited and challenging because precise control of the conjugation sites is needed. Herein, a novel synthetic polymer that can enzymatically assemble multiple proteins was developed. Polyacrylamide grafted with multiple microbial transglutaminase (MTG)-recognizable peptide derivatives was synthesized, and MTG-catalyzed site-specific conjugation of proteins with the polymer was achieved. The application for immunological biosensing was demonstrated using the assembly of a fusion protein composed of antibody-binding and enzyme moieties. This enzymatic method to synthesize a one-dimensional protein assembly on a synthetic polymer is versatile and can be expanded to a wide range of applications..
68. Norasikin Othman, Norul Fatiha Mohamed Noah, Lim Yin Shu, Zing Yi Ooi, Norela Jusoh, Mariani Idroas, Masahiro Goto, Easy removing of phenol from wastewater using vegetable oil-based organic solvent in emulsion liquid membrane process, Chinese Journal of Chemical Engineering, 10.1016/j.cjche.2016.06.002, 25, 1, 45-52, 2017.01, Phenol is considered as pollutant due to its toxicity and carcinogenic effect. Thus, variety of innovative methods for separation and recovery of phenolic compounds is developed in order to remove the unwanted phenol from wastewater and obtain valuable phenolic compound. One of potential method is extraction using green based liquid organic solvent. Therefore, the feasibility of using palm oil was investigated. In this research, palm oil based organic phase was used as diluents to treat a simulated wastewater containing 300 × 10-6of phenol solution using emulsion liquid membrane process (ELM). The stability of water-in-oil (W/O) emulsion on diluent composition and the parameters affecting the phenol removal efficiency and stability of the emulsion; such as emulsification speed, emulsification time, agitation speed, surfactant concentration, pH of external phase, contact time, stripping agent concentration and treat ratio were carried out. The results of ELM study showed that at ratio 7 to 3 of palm oil to kerosene, 5 min and 1300 r·min− 1of emulsification process the stabile primary emulsion were formed. Also, no carrier is needed to facilitate the phenol extraction. In experimental conditions of 500 r·min− 1of agitation speed, 3% Span 80, pH 8 of external phase, 5 min of contact time, 0.1 mol·L− 1NaOH as stripping agent and 1:10 of treat ratio, the ELM process was very promising for removing the phenol from the wastewater. The extraction performance at about 83% of phenol was removed for simulated wastewater and an enrichment of phenol in recovery phase as phenolate compound was around 11 times..
69. Tatsuo Maruyama, Masahiro Goto, Liquid-liquid extraction of enzymatically synthesized functional RNA oligonucleotides using reverse micelles with a DNA-surfactant, CHEMICAL COMMUNICATIONS, 10.1039/c6cc06985a, 52, 83, 12376-12379, 2016.12.
70. Momoko Kitaoka, Rie Wakabayashi, Norah Kamiya, Masahiro Goto, Solid-in-oil nanodispersions for transdermal drug delivery systems, BIOTECHNOLOGY JOURNAL, 10.1002/biot.201600081, 11, 11, 1375-1385, 2016.11.
71. Lotfi, Meysam, Moniruzzaman, Muhammad, Masahiro Goto, Analysis of Multiple Solvation Interactions of Methotrexate and Ammonium Based Ionic Liquids Using COSMO-RS, PROCEEDING OF 4TH INTERNATIONAL CONFERENCE ON PROCESS ENGINEERING AND ADVANCED MATERIALS (ICPEAM 2016), 10.1016/j.proeng.2016.06.464, 148, 459-466, 2016.11.
72. Kousuke Moriyama, Masahiro Goto, Norah Kamiya, Enzymatically prepared redox-responsive hydrogels as potent matrices for hepatocellular carcinoma cell spheroid formation, BIOTECHNOLOGY JOURNAL, 10.1002/biot.201600087, 11, 11, 1452-1460, 2016.11.
73. Zhigang Zhao, F. Kubota, Masahiro Goto, Development of novel adsorbent bearing aminocarbonylmethylglycine and its application to scandium separation, JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 10.1002/jctb.4884, 91, 11, 2779-2784, 2016.11.
74. Adawiyah, Noorul, Moniruzzaman, Muhammad, Masahiro Goto, Ionic liquids as a potential tool for drug delivery systems, MEDCHEMCOMM, 10.1039/c6md00358c, 7, 10, 1881-1897, 2016.10.
75. Lili Jia, Masahiro Goto, Norah Kamiya, Synergistic degradation of arabinoxylan by free and immobilized xylanases and arabinofuranosidase, BIOCHEMICAL ENGINEERING JOURNAL, 10.1016/j.bej.2016.07.013, 114, 271-278, 2016.10.
76. Yukio Hosomomi, Masahiro Goto, Diglycolic amic acid-modified E. coli as a biosorbent for the recovery of rare earth elements, BIOCHEMICAL ENGINEERING JOURNAL, 10.1016/j.bej.2016.06.005, 113, 102-106, 2016.09.
77. Sivapragasam, Magaret, Moniruzzaman, Muhammad, Masahiro Goto, Recent advances in exploiting ionic liquids for biomolecules: Solubility, stability and applications, BIOTECHNOLOGY JOURNAL, 10.1002/biot.201500603, 11, 8, 1000-1013, 2016.08.
78. Uju, Masahiro Goto, Norah Kamiya, Powerful peracetic acid-ionic liquid pretreatment process for the efficient chemical hydrolysis of lignocellulosic biomass, BIORESOURCE TECHNOLOGY, 10.1016/j.biortech.2016.04.121, 214, 487-495, 2016.08.
79. Water Yoshida, Masahiro Goto, Cu(II)-Imprinted Chitosan Derivative Containing Carboxyl Groups for the Selective Removal of Cu(II) from Aqueous Solution, JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 10.1252/jcej.15we293, 49, 7, 630-634, 2016.07.
80. Mari Takahara, Masahiro Goto, Norah Kamiya, Enzymatic conjugation of multiple proteins on a DNA aptamer in a tail-specific manner, BIOTECHNOLOGY JOURNAL, 10.1002/biot.201500560, 11, 6, 814-823, 2016.06.
81. Elgharbawy, Amal A., Moniruzzaman, Muhammad, Masahiro Goto, Ionic liquid pretreatment as emerging approaches for enhanced enzymatic hydrolysis of lignocellulosic biomass, BIOCHEMICAL ENGINEERING JOURNAL, 10.1016/j.bej.2016.01.021, 109, 252-267, 2016.05.
82. Yuzo Baba, Masahiro Goto, Mutual Separation of Indium, Gallium, and Zinc with the Amic Acid-type Extractant D2EHAG Containing Glycine and Amide Moieties, SOLVENT EXTRACTION RESEARCH AND DEVELOPMENT-JAPAN, 23, 9-18, 2016.05.
83. Akira Tsuchiya, Masahiro Goto, Shinsuke Sando, BODIPY-labeled Fluorescent Aptamer Sensors for Turn-on Sensing of Interferon-gamma and Adenine Compounds on Cells, ANALYTICAL SCIENCES, 32, 5, 543-547, 2016.05.
84. Akira Tsuchiya, Siti N. Hashim, Shoko Ise, Takafumi Furuhata, Kiyohiko Kawai, Rie Wakabayashi, Masahiro Goto, Noriho Kamiya, Shinsuke Sando, BODIPY-labeled fluorescent aptamer sensors for turn-on sensing of interferon-gamma and adenine compounds on cells, analytical sciences, 10.2116/analsci.32.543, 32, 5, 543-547, 2016.01, An on-cell aptamer sensor has the potential to reveal cell-cell communications by signalling molecules. We attempted to design new fluorescent aptamer sensors for the sensing of IFN-? and adenine compounds on cells. BODIPY-labeled external quencher-free aptamer sensors have allowed a turn-on detection of the target molecule with improved off/on efficiency..
85. Yukiho Hosomomi, Teppei Niide, Rie Wakabayashi, Masahiro Goto, Noriho Kamiya, Biocatalytic formation of gold nanoparticles decorated with functional proteins inside recombinant Escherichia coli cells, analytical sciences, 10.2116/analsci.32.295, 32, 3, 295-300, 2016.01, A novel strategy for the preparation of protein-decorated gold nanoparticles (Au NPs) was developed inside Escherichia coli cells, where an artificial oxidoreductase, composed of antibody-binding protein (pG), Bacillus stearothermophilus glycerol dehydrogenase (BsGLD) and a peptide tag with gold-binding affinity (H 6 C), was overexpressed in the cytoplasm. In situ formation of Au NPs was promoted by a natural electron-donating cofactor, nicotinamide adenine dinucleotide (NAD), which was regenerated to the reduced form of NADH by the catalytic activity of the fusion protein (pG-BsGLDH 6 C) overexpressed in the cytoplasm of E. coli, with the concomitant addition of exogenous glycerol to the reaction system. The fusion protein was self-immobilized on Au NPs inside the E. coli cells, which was confirmed by SDS-PAGE and western blotting analyses of the resultant Au NPs. Finally, the IgG binding ability of the pG moiety displayed on Au NPs was evaluated by an enzyme-linked immunosorbent assay. 2016.
86. Yuzo Baba, Fukiko Kubota, Noriho Kamiya, Masahiro Goto, Mutual separation of indium, gallium, and zinc with the amic acid-type extractant D2EHAG containing glycine and amide moieties, Solvent Extraction Research and Development, 10.15261/serdj.23.9, 23, 1, 9-18, 2016.01, Solvent extraction of indium (In3+), gallium (Ga3+), and zinc (Zn2+) was investigated using N-[N,N-di(2-ethylhexyl)aminocarbonylmethyl]glycine (D2EHAG) and N-[N,N-di(2-ethylhexyl)aminocarbonylmethyl]-sarcosine (D2EHAS) which we have developed recently. Indium and gallium were selectively extracted from zinc under high acid conditions (0 > pH ≥ 2.0), and easily stripped using an acidic solution such as 2 mol dm-3 HNO3. The extraction behavior was compared to that of N,N-dioctyldiglycol amic acid (DODGAA), which has a similar molecular structure to D2EHAG, a commercial alkyl monocarboxylic acid extractant, neodecanoic acid (Versatic 10), or an organophosphorus extractant, di(2-ethylhexyl) phosphoric acid (D2EHPA). Based on the results, D2EHAG and D2EHAS were found to be useful for the separation of In3+ and Ga3+ from Zn2+. The extraction mechanisms of these ions with D2EHAG were investigated through slope analysis and loading tests..
87. Zhigang Zhao, Fukiko Kubota, Noriho Kamiya, Masahiro Goto, Selective extraction of scandium from transition metals by synergistic extraction with 2-thenoyltrifluoroacetone and tri-n-octylphosphine oxide, Solvent Extraction Research and Development, 10.15261/serdj.23.137, 23, 2, 137-143, 2016.01, There has been an increasing demand for scandium (Sc). However the supply is insufficient because the separation and recovery of Sc as a byproduct from ores is difficult. In this study, extraction and separation of Sc3+ from a sulfuric acid solution containing transition metals such as Al3+, Fe3+, Mn2+, Co2+, Ni2+ and Zn2+ was investigated using a β-diketone, HTTA and a neutral extractant, TOPO. Due to the synergistic effect with the two extractants, Sc3+ was effectively and selectively separated even from Fe3+, the separation of which is difficult with HTTA alone. The extraction mechanism was examined and it was revealed that Sc3+ is extracted with three HTTA and one TOPO molecules. Scandium was readily stripped from the extracting phase by 1 M sulfuric acid. The potential use of the combination of the β-diketone with TOPO for the recovery of Sc3+ in a refining process was demonstrated..
88. Masahiro Goto, Transcutaneous immunization against cancer using solid-in-oil nanodispersions, MEDCHEMCOMM, 10.1039/c5md00168d, 6, 7, 1387-1392, 2015.05, 特殊なナノコーティングによって、ガン抗原タンパク質をナノカプセル化し、担ガンマウスを用いて、ガンのワクチン効果を検証した。その結果、経皮投与によって、注射に匹敵するガンの抑制効果が観察された。.
89. Momoko Kitaoka, Masahiro Goto, Transdermal Immunization using Solid-in-oil Nanodispersion with CpG Oligodeoxynucleotide Adjuvants, PHARMACEUTICAL RESEARCH, 10.1007/s11095-014-1554-5, 32, 4, 1486-1492, 2015.04.
90. Jian Yan, Masahiro Goto, Separation of Gold(III) in Acidic Chloride Solution Using Porous Polymeric Ionic Liquid Gel, JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 10.1252/jcej.14we162, 48, 3, 197-201, 2015.04.
91. Tatsuo Maruyama, Masahiro Goto, Cancer Cell Death Induced by the Intracellular Self-Assembly of an Enzyme-Responsive Supramolecular Gelator, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 10.1021/ja510156v, 137, 2, 770-775, 2015.04.
92. 後藤 雅宏, Ionic liquid-mediated transcutaneous protein delivery with solid-in-oil nanodispersions, MEDCHEMCOMM, 10.1039/c5md00378d, 6, 12, 2124-2128, 2015.04.
93. Kosuke Minamihata, Masahiro Goto, Noriho Kamiya, Site-specific conjugation of an antibody-binding protein catalyzed by horseradish peroxidase creates a multivalent protein conjugate with high affinity to IgG, BIOTECHNOLOGY JOURNAL, 10.1002/biot.201400512, 10, 1, 222-226, 2015.01.
94. Kosuke Moriyama, Masahiro Goto, Noriho Kamiya, Enzyme-mediated preparation of hydrogels composed of poly(ethylene glycol) and gelatin as cell culture platforms, RSC ADVANCES, 10.1039/c4ra12334d, 5, 4, 3070-3073, 2015.01.
95. Kosuke Moriyama, Masahiro Goto, Noriho Kamiya, Characterization of enzymatically gellable, phenolated linear poly(ethylene glycol) with different molecular weights for encapsulating living cells, BIOCHEMICAL ENGINEERING JOURNAL, 10.1016/j.bej.2014.09.003, 93, 25-30, 2015.01.
96. M. Moniruzzaman, H. Mahmood, Noriho Kamiya, S. Yusup, Masahiro Goto, Activity and stability of enzyme immobilized with ionic liquid based polymer materials, Journal of Engineering Science and Technology, 10, 60-69, 2015.01, Enzyme immobilization methods are continuously being developed for a wide range of applications including biocatalysis and biotransformation. Compared to other immobilization methods, physical entrapment into a matrix is relatively simple and inexpensive, and causes a relatively small perturbation to the native enzyme structure and function. However, significant enzyme leaching from such biocatalytic polymers is the main constraint in using them for industrial levels. This study reports an ionic liquid (IL) polymer materials incorporating enzymes that can be used as active, stable and reusable biocatalysts to overcome the limitations. Lipase was microencapsulated in surfactant aggregates formed in an IL monomer or the solution of an IL monomer/IL and then incorporated into polymer frameworks through the free radical polymerization of an IL (1-vinyl-3-ethylimidazolium bis(trifluoromethylsulfonyl) amide ([veim][Tf2N]). The activity, stability and reusability of IL polymer materials containing lipase were evaluated using lipase-catalyzed hydrolysis of p-nitrophenyl butyrate (p-PNB) as a model reaction. It was found that lipase IL polymer materials exhibited excellent stability in aqueous solutions. More importantly, these biopolymer materials retained most of their activity after six reaction cycles. We firmly believe that enzyme containing IL polymeric materials developed in this study will provide several advantages over conventional polymer based methods for diverse enzymatic reactions..
97. Rie Wakabayashi, Masahiro Goto, A novel surface-coated nanocarrier for efficient encapsulation and delivery of camptothecin to cells, MEDCHEMCOMM, 10.1039/c4md00179f, 5, 10, 1515-1519, 2014.10.
98. Jian Yan, Masahiro Goto, Application of cellulose acetate to the selective adsorption and recovery of Au(III), CARBOHYDRATE POLYMERS, 10.1016/j.carbpol.2014.05.003, 111, 768-774, 2014.10.
99. Tkahiko Kakoi, Masahiro Goto, Separation of Platinum and Palladium from Hydrochloric Acid Solutions with 1-Octyl-3-methylimidazolium Hexafluorophosphate as an Extractant, JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 10.1252/jcej.14we052, 47, 8, 666-670, 2014.08.
100. Kosuke Noriyama, Masahiro Goto, Noriho Kamiya, Enzymatic preparation of a redox-responsive hydrogel for encapsulating and releasing living cells, CHEMICAL COMMUNICATIONS, 10.1039/c3cc49766f, 50, 44, 5895-5898, 2014.08.
101. Zhigang Zhao, Masahiro Goto, Synergistic Extraction of Rare-Earth Metals and Separation of Scandium Using 2-Thenoyltriuoroacetone and Tri-n-octylphosphine Oxide in an Ionic Liquid System, JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 10.1252/jcej.14we360, 47, 8, 656-662, 2014.08.
102. Atsuomi Shundou, Masahiro Goto, Keiji Tanaka, Facile microcapsule fabrication by spray deposition of a supramolecular hydrogel, RSC ADVANCES, 10.1039/c4ra04636f, 4, 68, 36097-36100, 2014.06.
103. Tatsuo Maruyama, Masahiro Goto, Selective adsorption and recovery of precious metal ions using protein-rich biomass as efficient adsorbents, PROCESS BIOCHEMISTRY, 10.1016/j.procbio.2014.02.016, 49, 5, 850-857, 2014.05.
104. Jian Yang, Fukiko Kubota, Yuzo Baba, Noriho Kamiya, Masahiro Goto, One step effective separation of platinum and palladium in an acidic chloride solution by using undiluted ionic liquids, Solvent Extraction Research and Development, 10.15261/serdj.21.129, 21, 2, 129-135, 2014.05, Imidazolium-based ionic liquids (ILs) with Tf2N- as anions were studied as extractants without dilution for the extractive separation of platinum and palladium in an acidic chloride solution. The effect of the alkyl chain length on the extraction performance was evaluated and, based on the performance, the IL, 1-methyl-3-octylimidazolium bis(trifluoromethylsulfonyl) imide ([Omim][Tf2N]), was selected to be studied in detail. The extraction of Pt(IV) underwent little change over the HCl concentration studied, while that of Pd(II) decreased with increasing HCl concentration. The separation of Pt(IV) and Pd(II) was highly effective, and the highest separation factor between Pt(IV) and Pd(II) reached 312 at the optimum conditions in a binary component system composed of Pt(IV) and Pd(II). The effect of the initial Pt(IV) concentration on loading capacity and extraction efficiency of Pt(IV) was also investigated..
105. Jian Yang, Fukiko Kubota, Yuzo Baba, Noriho Kamiya, Masahiro Goto, Separation of precious metals by using undiluted ionic liquids, Solvent Extraction Research and Development, 10.15261/serdj.21.89, 21, 1, 89-94, 2014.05, The ionic liquid (IL), 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Bmim][Tf2N]), was evaluated as an extractant without dilution for the separation and recovery of precious metals. Au(III) was efficiently extracted from the aqueous phase to the IL phase, and a concentrated Au(III) solution almost 8 times higher than the initial feed solutions could be produced. In contrast, Pd(II) was rarely extracted and Pt(IV) was partly extracted under the present experimental conditions. Furthermore, the effect of the IL anions on the extraction ability for the metal ions was examined, and it was found that an IL having an anion component slightly more hydrophilic compared to [Tf2N], such as 1-butyl-3-methylimidazolium hexafluorophosphate [Bmim][PF6], showed a higher extraction ability than [Bmim][Tf2N]. It was suggested that the extraction proceeded via an anion exchange mechanism and it was shown that ILs could be effective extractants for the separation of precious metals..
106. 二井手 哲平, 後藤 雅宏, 神谷 典穂, Enzymatic self-sacrificial display of an active protein on gold nanoparticles, RSC ADVANCES, 10.1039/c3ra46384b, 4, 12, 5995-5998, 2014.04.
107. Rie Wakabayashi, Masahiro Goto, The self-assembly and secondary structure of peptide amphiphiles determine the membrane permeation activity, RSC ADVANCES, 10.1039/c4ra02901a, 4, 58, 30654-30657, 2014.04.
108. Kojiro Shimojo, Fukiko Kubota, Masahiro Goto, Highly Efficient Extraction Separation of Lanthanides Using a Diglycolamic Acid Extractant, ANALYTICAL SCIENCES, 30, 2, 263-269, 2014.02.
109. Kojiro Shimojo, Masahiro Goto, Highly Efficient Extraction Separation of Lanthanides Using a Diglycolamic Acid Extractant, ANALYTICAL SCIENCES, 30, 2, 263-269, 2014.02.
110. Kojiro Shimojo, Noboru Aoyagi, Takumi Saito, Hiroyuki Okamura, Fukiko Kubota, Masahiro Goto, Hirochika Naganawa, Highly efficient extraction separation of lanthanides using a diglycolamic acid extractant, analytical sciences, 10.2116/analsci.30.263, 30, 2, 263-269, 2014.02, Liquid-liquid extraction of lanthanide ions (Ln 3+ ) using N,N-dioctyldiglycolamic acid (DODGAA) was comprehensively investigated, together with fluorescence spectroscopic characterization of the resulting extracted complexes in the organic phase. DODGAA enables the quantitative partitioning of all Ln 3+ ions from moderately acidic solutions, while showing selectivity for heavier lanthanides, and provides remarkably high extraction separation performance for Ln 3+ compared with typical carboxylic acid extractants. Furthermore, the mutual separation abilities of DODGAA for light lanthanides are higher than those of organophosphorus extractants. Slope analysis, loading tests, and electrospray ionization mass spectrometry measurements demonstrated that the transfer of Ln 3+ with DODGAA proceeded through a proton-exchange reaction, forming a 1:3 complex, Ln(DODGAA) 3 . The stripping of Ln 3+ from the extracting phase was successfully achieved under acidic conditions. Time-resolved laser-induced fluorescence spectroscopy revealed that the extracted Eu 3+ ions were completely dehydrated by complexation with DODGAA..
111. Masahiro Goto, Teppei Niide, Noriho Kamiya, Enzymatic self-sacrificial display of an active protein on gold nanoparticles, RSC ADVANCES, 10.1039/c3ra46384b, 4, 12, 5995-5998, 2014.01.
112. 北岡 桃子, Kana Imamura, Noriho Kamiya, Masahiro Goto, Sucrose laurate-enhanced transcutaneous immunization with a solid-in-oil nanodispersion, MEDCHEMCOMM, 10.1039/c3md00164d, 5, 1, 20-24, 2014.01.
113. Yuzo Baba, Fukiko Kubota, Masahiro Goto, Development of Novel Extractants with Amino Acid Structure for Efficient Separation of Nickel and Cobalt from Manganese Ions, INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 10.1021/ie403524a, 53, 2, 812-818, 2014.01.
114. Mari Takahara, Masahiro Goto, Noriho Kamiya, Tailing DNA aptamers with a functional protein by two-step enzymatic reaction, JOURNAL OF BIOSCIENCE AND BIOENGINEERING, 10.1016/j.jbiosc.2013.05.025, 116, 6, 660-665, 2013.12.
115. Teppei Niide, Masahiro Goto, Noriho Kamiya, Enzymatic Fabrication of Protein-Decorated Gold Nanoparticles by the Aid of Artificial Peptides with Gold-Binding Affinity, LANGMUIR, 10.1021/la401327h, 29, 50, 15596-15605, 2013.12.
116. 北岡 桃子, Kana Imamura, Noriho Kamiya, Masahiro Goto, Needle-free immunization using a solid-in-oil nanodispersion enhanced by a skin-permeable oligoarginine peptide, INTERNATIONAL JOURNAL OF PHARMACEUTICS, 10.1016/j.ijpharm.2013.10.006, 458, 2, 334-339, 2013.12, 注射を不要とするワクチン投与技術野開発に成功した。.
117. Hiromu Yoshiura, Noriho Kamiya, Masahiro Goto, Ionic Liquid-in-Oil Microemulsions as Potential Carrier for the Transdermal Delivery of Methotrexate, J. Chem. Eng. Japan, 46, 11, 794-796, 2013.11.
118. Yukiho Hosomomi, Fukiko Kubota, Masahiro Goto, Biosorption of Rare Earth Elements by Escherichia coli, J. Chem. Eng. Japan, 46, 7, 450-454, 2013.09.
119. Hiroki Abe, Masahiro Goto, Noriho Kamiya, Split Spy0128 as a potent scaffold for protein cross-linking and immobilization, Bioconjugate Chem., 22, 242-250, 2013.08.
120. Kosuke Moriyama, Masahiro Goto, Noriho Kamiya, Enzymatic preparation of streptavidin-immobilized hydrogel using a phenolated linear poly(ethylene glycol), BIOCHEMICAL ENGINEERING JOURNAL, 10.1016/j.bej.2013.04.007, 76, 37-42, 2013.07.
121. Tatsuaya Okuda, Masahiro Goto, Satoru Kidoaki, S/O-nanodispersion electrospun fiber mesh effective for sustained release of healthy plasmid DNA with the structural and functional integrity, JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION, 10.1080/09205063.2012.755600, 24, 10, 1277-1290, 2013.07.
122. Masahiro Goto, Kosuke Moriyama, Noriho Kamiya, Enzymatic preparation of streptavidin-immobilized hydrogel using a phenolated linear poly(ethylene glycol), BIOCHEMICAL ENGINEERING JOURNAL, 10.1016/j.bej.2013.04.007, 76, 37-42, 2013.07.
123. Atsuomi Shundo, Masahiro Goto, Keiji Tanaka, Spatial Heterogeneity in the Sol-gel Transition of a Supramolecular System, Soft Matter,, 9, 5166-5172, 2013.07.
124. Fan Yang, Fukiko Kubota, Masahiro Goto, Selective extraction and recovery of rare earth metals from phosphor powders in waste fluorescent lamps using an ionic liquid system, JOURNAL OF HAZARDOUS MATERIALS, 10.1016/j.jhazmat.2013.03.026, 254, 79-88, 2013.06.
125. Masahiro Goto, Noriho Kamiya, Uju, Peracetic acid-ionic liquid pretreatment to enhance enzymatic saccharification of lignocellulosic biomass, BIORESOURCE TECHNOLOGY, 10.1016/j.biortech.2013.03.147, 138, 87-94, 2013.06.
126. Uju, Masahiro Goto, Noriho Kamiya, Low melting point pyridinium ionic liquid pretreatment for enhancing enzymatic saccharification of cellulosic biomass, BIORESOURCE TECHNOLOGY, 10.1016/j.biortech.2012.06.096, 135, 103-108, 2013.05.
127. Fan Yang, Fukiko Kubota, Masahiro Goto, Extraction of Rare-Earth Ions with an 8-Hydroxyquinoline Derivative in an Ionic Liquid, Solvent Extraction Research and Development, Japan, 20, 1, 123-129, 2013.05.
128. Fan Yang, Fukiko Kubota, Masahiro Goto, A Comparative Study of Ionic Liquids and a Conventional Organic Solvent on the Extraction of Rare-earth Ions with TOPO, Solvent Extraction Research and Development, Japan, 20, 1, 225-232, 2013.05.
129. Yutaro Mori, Masahiro Goto, Noriho Kamiya, Protein supramolecular complex formation by site-specific avidin-biotin interactions, ORGANIC & BIOMOLECULAR CHEMISTRY, 10.1039/c2ob26625c, 11, 6, 914-922, 2013.04.
130. T. Monjo, Masahiro Goto, Tatsuo Maruyama, Preparation of affnity membranes using thermally induced phase separation for one-step puri?cation of recombinant proteins, Anal. Biochem., 434, 269-274, 2013.04.
131. Shinya Furukawa, Masahiro Goto, Noriho Kamiya, Enzymatic synthesis of Z-aspartame in liquefied amino acid substrates, BIOCHEMICAL ENGINEERING JOURNAL, 10.1016/j.bej.2012.10.002, 70, 84-87, 2013.04.
132. Uju, Masahiro Goto, Noriho Kamiya, Low melting point pyridinium ionic liquid pretreatment for enhancing enzymatic saccharification of cellulosic biomass, Bioresource Technology, 48, 874-882, 2012.12.
133. Yoshiro Tahara, Noriho Kamiya, Masahiro Goto, Transdermal delivery of insulin using a solid-in-oil nanodispersion enhanced by arginine-rich peptides, MEDCHEMCOMM, 10.1039/c2md20059g, 3, 12, 1496-1499, 2012.12.
134. S. Egusa, Masahiro Goto, Takuya Kitaoka, Facile and direct synthesis oflong-chain chitinfromchitobiose via proton-assisted nonaqueous biocatalysis, J. Molecular Catal. B, Enzymatic, 87, 69-74, 2012.12.
135. Masahiro Goto, Kosuke Minamihata, Noriho Kamiya, Activation of Pyrococcus furiosus alkaline phosphatase by divalent metal ions, BIOTECHNOLOGY LETTERS, 10.1007/s10529-012-0998-0, 34, 11, 2055-2060, 2012.11.
136. Fang Yang, Noriho Kamiya, Masahiro Goto, Transdermal delivery of the anti-rheumatic agent methotrexate using a solid-in-oil nanocarrier, EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS, 10.1016/j.ejpb.2012.05.016, 82, 1, 158-163, 2012.09.
137. S. Egusa, Masahiro Goto, Takuya Kitaoka, One-Step Synthesis of Cellulose from Cellobiose via Protic Acid-Assisted Enzymatic Dehydration in Aprotic Organic Media, BIOMACROMOLECULES, 10.1021/bm3006775, 13, 9, 2716-2722, 2012.09.
138. Masahiro Goto, Yoshiro Tahara, Noriho Kamiya, A novel double-coating carrier produced by solid-in-oil and solid-in-water nanodispersion technology for delivery of genes and proteins into cells, J. Controlled Release, 16, 713-721, 2012.08.
139. Kosuke Minamihata, Masahiro Goto, Noriho Kamiya, Control of a Tyrosyl Radical Mediated Protein Cross-Linking Reaction by Electrostatic Interaction, BIOCONJUGATE CHEMISTRY, 10.1021/bc300137s, 23, 8, 1600-1609, 2012.08.
140. Kojiro Shimojo, Masahiro Goto, Noriho Kamiya, Facile, rapid and efficient biofabrication of gold nanoparticles decorated with functional proteins, Analyst., 137, 2300-2303, 2012.07.
141. K. Nose, Masahiro Goto, Yoshiki Katayama, Gold nanorods in an oil-base formulation for transdermal treatment of type 1 diabetes in mice, Nanoscale, 4, 3776-3780, 2012.06.
142. Momoko Kitaoka, Masahiro Goto, Noriho Kamiya, Transglutaminase-mediated in situ hybridization (TransISH) system: A new methodology for simplified mRNA detection., Anal. Chem, 84, 5885-5891, 2012.06.
143. Tatsuo Maruyama, Masahiro Goto, Versatile Supramolecular Gelators That Can Harden Water, Organic Solvents and Ionic Liquids, LANGMUIR, 10.1021/la301442f, 28, 25, 9259-9266, 2012.06.
144. T. Niide, M. Goto, N. Kamiya, Biocatalytic synthesis of gold nanoparticles with cofactor regeneration in recombinant Escherichia coli, Chem. Comm., 47, 7350-7352, 2012.05.
145. Uju, Masahiro Goto, Noriho Kamiya, Short time ionic liquids pretreatment on lignocellulosic biomass to enhance enzymatic saccharification, Bioresour. Technol., 103, 446-452, 2012.05.
146. Masahiro Goto, Josui Shimada, Noriho Kamiya, Microplate assay for aptamer-based thrombin detection using a DNA-enzyme conjugate based on His-tag chemistry, Anal. Biochem., 421, 541-546, 2012.05.
147. Masahiro Goto, Josui Shimada, Noriho Kamiya, Programmable protein protein conjugation via DNA-based self-assembly, Chem. Commun, 48, 6226-6228, 2012.05.
148. Fang Yang, Fukiko Kubota, Noriho Kamiya, Masahiro Goto, Extraction and Separation of Rare Earth Metal Ions with DODGAA in Ionic liquids, Solv. Extr. Res. Dev. Jpn,, 19, 1, 69-76, 2012.05.
149. Takahiko Kakoi, Masahiro Goto, Extraction Behavior of Gold from Hydrochloric Acid Solution with Ionic Liquids as Extractants, Solvent Extraction Research and Development, Japan, 19, 63-68, 2012.05.
150. Eiichi Toorisaka, Masahiro Goto, Intestinal patches with an immobilized solid-in-oil formulation for oral protein delivery, Acta Biomaterialia, 8, 653-658, 2012.04.
151. Y. Mori, M. Goto, N. Kamiya, Transglutaminase-mediated internal protein labeling with a designed peptide loop, Biochem. Biophys. Res. Commun., 410, 829-833, 2011.10.
152. E. Toorisaka, K. Watanabe, H. Ono, M. Hirata, N. Kamiya, M. Goto, Intestinal patches with an immobilized solid-in-oil formulation for oral protein delivery, Acta Biomaterialia, 8, 965-968, 2011.09.
153. Y.Mori, K. Minamihata, H. Abe, M. Goto, N. Kamiya, protein assemblies by site-specific avidin-biotin interactions, Org. Biomol. Chem., 9, 5641-5644, 2011.09.
154. H. Piao, N. Kamiy, F. Cui, M. Goto, Preparation of a solid-in-oil nanosuspension containing l-ascorbic acid as a novel long-term stable topical formulation, Int. J. Pharm., 420, 156-160, 2011.08.
155. Uju, Y. Shoda, A. Nakamoto, M. Goto, W. Tokuhara, Y. Noritake, S. Katahira, N. Ishida, K. Nakashima, C. Ogino, N. Kamiya, Short Time Ionic Liquids Pretreatment On Lignocellulosic Biomass To Enhance Enzymatic Saccharification, Bioresource Technology, 52, 954-958, 2011.07.
156. A. Shundo, K. Mizuguchi, M. Miyamoto, M. Goto, K. Tanaka, Controllable Heterogeneity in a Supramolecular Hydrogel, Chem. Commun., 47, 31, 8844-8846, 2011.07.
157. T. Maruyama, S. Tabayashi, T. Honjo, K. Hoe, T. Tanaka, J. Shimada, M. Goto, H. Matsuyama, Task-specific membranes for the isolation of recombinant proteins with peptide-tags, RSC Advances, 8, 1254-1259, 2011.07.
158. K. Moriyama, K. Sung, M. Goto, N. Kamiya, Immobilization of bacterial alkaline phosphatase on magnetic particles by site-specific and covalent cross-linking catalyzed by microbial transglutaminase, J. Biosci. Bioeng., 111, 650-653, 2011.06.
159. J. Shimada, T. Maruyama, M. Kitaoka, N. Kamiya, M. Goto, DNA-enzyme conjugate with a weak inhibitor that can specifically detect thrombin in a homogeneous medium, Anal. Biochem., 414, 103-108, 2011.06.
160. F.Kubota, Y. Shimobori, Y. Baba, Y. Koyanagi, K. Shimojo, N. Kamiya, M. Goto, Application of ionic liquids to extraction separation of rare earth metals with an effective diglycol amic acid extractant, J. Chem. Eng. Japan, 51, 878-882, 2011.06.
161. M. Kitaoka, Y. Tanaka, Y. Tada, M. Goto, K. Miyawaki, S. Noji, N. Kamiya, Conjugation of enzymes on RNA probes through Cu(I) catalyzed alkyne-azide cycloaddition, Biotechnol. J., 7, 156-162, 2011.06.
162. T. Mouri, N. Kamiya, M. Goto, New strategy to enhance catalytic performance of Escherichia coli whole cell biocatalysts harboring P450cam mutants, 53, 229-233, 2011.05.
163. K. Minamihata, M. Goto, N. Kamiya, Site-Specific Protein Cross-Linking by Peroxidase-Catalyzed Activation of a Tyrosine-Containing Peptide Tag, Bioconjugate Chem., 22, 74-81, 2011.05.
164. M. Kitaoka, Y. Tsuruda, Y. Tanaka, M. Goto, M. Mitsumori, K. Hayashi, Y. Hiraishi, K. Miyawaki, S. Noji, N. Kamiya, Transglutaminase-mediated synthesis of a novel DNA-(enzyme)n probe for highly sensitive DNA detection, Chem. Eur. J., 17, 19, 5387-5392, 2011.05.
165. Y. Baba, F. Kubota, N. Kamiya, M. Goto, Selective Recovery of Dysprosium and Neodymium Ions by a Supported Liquid Membrane Based on Ionic Liquids, Solvent Extraction Research and Development, Japan, 18, 193-198, 2011.05.
166. M. Sakono, K. Motomura, T. Maruyama, N. Kamiya, M. Goto, Alpha casein micelles show not only molecular chaperone-like aggregation inhibition properties but also protein refolding activity from the denatured state, Biochem. Biophys. Res. Commu, 26, 494-497, 2011.04.
167. D. Pissuwan, K. Nose, R. Kurihara, K. Kaneko, Y. Tahara, N. Kamiya, M. Goto, Y. Katayama, T. Niidome, A solid-in-oil dispersion of gold nanorods can enhance trandermal protein delivery and skin vaccination, Small, 7, 215-220, 2011.04.
168. S. Egusa, T. Kitaoka, K. Igarashi, M. Samejima, M. Goto, H. Wariishi, Preparation and enzymatic behavior of surfactant-enveloped enzymes for glycosynthesis in nonaqueous aprotic media, Journal of Molecular Catalysis B: Enzymatic, 67, 225-230, 2010.12.
169. Y. Tahara, K. Namatsu, N. Kamiya, M. Hagimori, S. Kamiya, M. Arakawa, M. Goto, Transcutaneous immunization by a solid-in-oil nanodispersion, Chem. Comm., 33, 341-343, 2010.11.
170. M. Moniruzzaman, M. Tamura, Y. Tahara, N. Kamiya, M. Goto, Ionic liquid-in-oil microemulsion as a potential carrier of sparingly soluble drug: Characterization and cytotoxicity evaluation, Int. J. Pharm., 400, 243-250, 2010.10.
171. M. Moniruzzaman, N. Kamiya, M. Goto, Ionic Liquid Based Microemulsion with Pharmaceutically Accepted Components: Formulation and Potential Applications, Journal of Colloid & Interface Science, 352, 136-142, 2010.09.
172. H. Abe, M. Goto, N. Kamiya, Enzymatic single-step preparation of multifunctional proteins, Chem. Commun., 33, 213-215, 2010.08.
173. M. Kitaoka, T. Wada, T. Nishio, M. Got, Fluorogenic Ribonuclease Protection (FRIP) Analysis of Single Nucleotide Polymorphisms (SNPs) in Japanese Rice (Oryza sativa L.) DNA for Cultivar Discrimination, Biosci. Biotech. Biochem., 45, 256-261, 2010.07.
174. Y. Okutani, S. Egusa, Y. Ogawa, T. Kitaoka, M. Goto, H. Wariishi, One-Step Lactosylation of Hydrophobic Alcohols by Nonaqueous Biocatalysis, Chem. Cat. Chem., 2, 950-952, 2010.06.
175. J. Okada, T. Maruyama, K. Motomura, K. Kuroki, K. Maenaka, M. Sakono, M. Goto, Enzyme-Mediated Protein Refolding, Chem. Comm., 2009, 7197-7199, 2010.05.
176. T. Niide, H. Shiraki, T. Oshima, Y. Baba, N. Kamiya, M. Goto, Quaternary ammonium bacterial cellulose for adsorption of proteins, Solvent Extr. Res. Dev., Jpn, 17, 73-81, 2010.05.
177. F. Kubota, Y. Shimobori, Y. Koyanagi, K. Shimojo, N. Kamiya, M. Goto, Uphill Transport of Rare Earth Metals through Highly Stable Supported Liquid Membrane Based on Ionic Liquid, Anal. Sci., 26, 289-290, 2010.05.
178. K. Sung, N. Kamiya, N. Kawata, S. Kamiya and M. Goto, Functional glass surface displaying a glutamyl donor substrate for transglutaminase-mediated protein immobilization, Biotechnol. J., 5, 456-462, 2010.04.
179. D. Koda, T. Maruyama, N. Minakuchi, K. Nakashima, and M. Goto, Proteinase-mediated drastic morphological change of peptide-amphiphile to induce supramolecular hydrogelation, Chem. Commun. , 46, 978-981, 2010.01.
180. M. Moniruzzaman, Y. Tahara, M. Tamura, N. Kamiya and M. Goto, Ionic liquid-assisted transdermal delivery of sparingly soluble drugs, Chem. Commun.,, 46, 1452-1454, 2010.01.
181. N. Kamiya, Y. Shiotari, M. Tokunaga, H. Matsunaga, H. Yamanouchi, K. Nakano, M. Goto, Stimuli-responsive nanoparticles composed of naturally occurring amphiphilic proteins, Chem. Commun, 54, 789-791, 2009.10.
182. M. Kukisaki, M. Goto, A Comparative Study of SPG Membrane Emulsification in the Presence and Absence of Continuous-Phase Flow, J. Chem. Eng. Japan, 42, 7, 520-530, 2009.10.
183. N. Kamiya, H. Abe, M. Goto, Y. Tsuji, H. Jikuya, Fluorescent substrates for covalent protein labeling catalyzed by microbial transglutaminase, Org. Biomol. Chem., , 8, 678-681, 2009.09.
184. K. Esaka, S. Yokota, S. Egusa, Y. Okutani, Y. Ogawa, T. Kitaoka, M. Goto, Preparation of Lactose-Modified Cellulose Films by a Nonaqueous Enzymatic Reaction and their Biofunctional Characteristics as a Scaffold for Cell Culture, Biomacromolecules, 10, 1265-1269, 2009.08.
185. M. Kitaoka, H. Ichinose, M. Goto, Simultaneous visual detection of single-nucleotide variations in tuna DNA using DNA/RNA chimeric probes and ribonuclease A, Analytical Biochem., , 389, 6-11, 2009.07.
186. F. Kubota, Y. Shimobori, Y. Koyanagi, K. Nakashima, K. Shimojo, N. Kamiya, M. Goto, Extraction Behavior of Indium with TOPO into Ionic Liquids, Solvent Extraction Research Development, Japan, 16, 142-146, 2009.07.
187. K. Minamihata, M. Tokunaga, N. Kamiya, S. Kiyoyama, H. Sakuraba, T. Ohshima, M. Goto, Development of a novel immobilization method for enzymes from hyperthermophiles, Biotechnology Letters, 21, 125, 128, 2009.06.
188. T. Mouri, T. Shimizu, N. Kamiya, H. Ichinose, M. Goto, Design of a cytochrome P450BM3 reaction system linked by two-step cofactor regeneration catalyzed by a soluble transhydrogenase and glycerol dehydrogenase, Biotechnol. Prog., , 25, 1372-1378, 2009.05.
189. K. Nakashima, N. Kamiya, D. Koda, T. Maruyama, M. Goto, Enzyme Encapsulation in Microparticles Composed of Polymerized Ionic Liquids for Highly Active and Reusable Biocatalysts, Org. Biomol. Chem., 35, 126-131(2009), 2009.04.
190. S. Egusa, S. Yokota, K. Tanaka, K. Esaki, Y. Okutani, Y. Ogawa, T. Kitaoka, M. Goto, H. Wariishi,, Surface modification of a solid-state cellulose matrix with lactose by a surfactant-enveloped enzyme in a nonaqueous medium, J. Mater. Chem., 19, 1836-1842(2009) , 2009.04.
191. M. Kitaoka, H. Ichinose, M. Goto, Simultaneous visual detection of single-nucleotide variations in tuna DNA using DNA/RNA chimeric probes and ribonuclease A, Analytical Biochem., 389, 6-11(2009) , 2009.04.
192. K. Esaka, S. Yokota, S. Egusa, Y. Okutani, Y. Ogawa, T. Kitaoka, M. Goto, H. Wariishi,, Preparation of Lactose-Modified Cellulose Films by a Nonaqueous Enzymatic Reaction and their Biofunctional Characteristics as a Scaffold for Cell Culture, Biomacromolecules, 10, 1265-1269(2009), 2009.04.
193. M.M. Zaman, N. Kamiya, and M. Goto, Biocatalysis in Water-in-Ionic Liquid Microemulsions: A Case Study with Horseradish  Peroxidase, Langmuir, 25, 977-982 (2009)., 2009.01.
194. K. Nakashima, T. Maruyama, F. Kubota, M. Goto, Metal Extraction from Water and Organic Solvents into Fluorous Solvents by Fluorinated β-Diketone and Its Application to the Colorimetric Analysis of Metal Ions, Anal. Sci., 32, 241-245(2009) , 2009.01.
195. M. Kitaoka, N. Okamura, H. Ichinose, M. Goto, Detection of SNPs in Fish DNA: Application of the Fluorogenic Ribonuclease Protection (FRIP) Assay for the Authentication of Food Contents" , J. Agric. Food Chem., 56, 6246-6251 (2008), 2008.12.
196. Y. Tahara, S. Honda, N. Kamiya, H. Piao, A. Hirata, E. Hayakawa, T. Fujii, M. Goto, A solid-in-oil nanodispersion for transcutaneous protein delivery, J. Control. Release, 131, 14-18 (2008), 2008.12.
197. S. Kiyoyama, T. Maruyama, N. Kamiya, M. Goto, Microcapsulation of DNA and the adsorption of toxic substances, J. Microencapsul., 25, 324-329 (2008), 2008.11.
198. J. Shimada, T. Maruyama, T. Hosogi, J. Tominaga, N. Kamiya, M. Goto, Conjugation of DNA with protein using His-tag chemistry and its application to the aptamer-based detection system, Biotechnol. Lett., 30, 2001-2006 (2008), 2008.10.
199. M. Kukizaki, M. Goto, Demulsification of water-in-oil emulsions by permeation through Shirasu-porous-glass (SPG) membranes, J.Membr. Sci., 322, 196-203 (2008), 2008.10.
200. H. Piao, N. Kamiya, A. Hirata, T. Fujii and M. Goto, A Nobel Solid-in-oil Nanosuspension for Transdermal Delivery of Diclofenac Sodium, Pharmaceutical Research., 25, 896-901 (2008)., 2008.08.
201. T. Maruyama, H. Yamamura, M. Hiraki, Y. Kemori, H. Takata and M. Goto, Directed aggregation and fusion of lipid vesicles induced by DNA-surfactants, Colloids and Surfaces B: Biointerfaces, Biointerfaces, 66, 119-124 (2008), 2008.08.
202. F. Kubota, Y. Koyanagi, K. Nakashima, K. Shimojo, N. Kamiya, M. Goto, Extraction of Lanthanide Ions with an Organophosphorous Extractant into Ionic Liquids, Solvent Extr. Res. Dev, -Jpn., 15, 81-87 (2008), 2008.08.
203. M. M. Zaman, N. Kamiya, K. Nakashima and M. Goto, Water-in-Ionic Liquid Microemulsions as a New Medium for Enzymatic Reactions, Green Chem., 10, 497-500 (2008), 2008.07.
204. H. Yoshiura, Y. Tahara, M. Hashida, N. Kamiya, A. Hirata, T. Fujii and M. Goto, Design and in vivo evaluation of solid-in-oil suspension for oral delivery of human growth hormone, Biochemical Engineering Journal, 41, 106-110 (2008), 2008.07.
205. Shiro Kiyoyama, Tatsuo Maruyama, Noriho Kamiya and Masahiro Goto, Immobilization of Proteins into Microcapsules and Their Adsorption Properties with respect to Precious-Metal Ions, Ind. Eng. Chem. Res., 47, 1527-1532 (2008), 2008.06.
206. Y. Tanaka, S. Doi, N. Kamiya, N. Kawata, S. Kamiya, K. Nakama, M. Goto, A chemically modified glass surface that facilitates transglutaminase-mediated protein immobilization, Biotechnol. Lett., 31, 1231-1236 (2008), 2008.05.
207. N. Kamiya, Y. Matsushita, M. Hanaki, K. Nakashima, M Narita, M. Goto and H. Takahashi, Enzymatic in situ Saccharification of Cellulose in Aqueous-Ionic Liquid Media, Biotechnol. Lett., 30, 1037-1040 (2008), 2008.04.
208. K. Nakashima, T. Maruyama, N. Kamiya and M. Goto, , Spectrophotometric Assay for Protease Activity in Ionic Liquids Using Chromogenic Substrates, Anal. Biochem., , 374, 285-290 (2008), 2008.03.
209. S. Hanioka, T. Maruyama, T. Sotani, M. Teramoto, H. Matsuyama, K. Nakashima, M. Hanaki, F. Kubota, M. Goto, , CO2 separation facilitated by task-specific ionic liquids using a supported liquid membrane, J. Membr. Sci. , 314, 1-4 (2008), 2008.02.
210. M. M. Zaman, N. Kamiya, K. Nakashima and M. Goto, Formation of Reverse Micelles in a Room-Temperature Ionic Liquid, ChemPhysChem. , 9, 689-692 (2008), 2008.01.
211. T. Oshima, B. Yoshinari, K. Shimojo, and M. Goto , Recognition of Lysine Residues on Protein Surfaces Using Calixarenes and Its Application. Curr. , Curr. Drug Discovery Tech., , 4, 220-228 (2007), 2007.12.
212. K. Shimojo, T. Oshima, H. Naganawa, M. Goto, "Calixarene-Assisted Protein Refolding via Liquid-Liquid Extraction", , Biomacromolecules,, 8, 3061-3066 (2007), 2007.10.
213. Hongyu Piao, Noriho Kamiya, Akihiko Hirata, Takeru Fujii and Masahiro Goto, 'A Novel Solid-in-oil Nanosuspension for Transdermal Delivery of Diclofenac Sodium' , Pharmaceutical Research, in press., 2007.10.
214. H. Naganawa, K. Shimojo, H. Mitamura, Y. Sugo, J. Noro, and M. Goto, A new "Green" Extractant of the Diglycol Amic Acid Type for Lanthanides, Solv. Extr. Res. & Devel. Japan, , 14, 151-160 (2007) , 2007.09.
215. N.Kamiya, S.Doi, Y.Tanaka, H.Ichinose, M.Goto, , Functional immobilization of recombinant alkaline phosphatases bearing a glutamyl donor substrate peptide of microbial transglutaminase, , J. Biosci. Bioeng., , 104, 195-199 (2007), 2007.09.
216. T. Maruyama, T. Hosogi, M. Goto, Sequence-selective extraction of single-stranded DNA using DNA-functionalized reverse micelles. , Chem. Commun. , 4450 (2007) , 2007.08.
217. Masato Kukizaki, Masahiro Goto, 'Preparation and characterization of a new asymmetric type of Shirasu porous glass (SPG) membrane used for membrane emulsification', JOURNAL OF MEMBRANE SCIENCE , 299 (1-2),190-199, 2007, 2007.08.
218. Muneharu GOTO, Hideaki KAWAKITA, Kazuya UEZU, Satoshi TUNEDA, Kyoichi SAITO, and Masahiro GOTO, , 'Design of Polymer Brushes for Immobilizing Enzymes onto Hollow Fiber Micropores in Organic Media Reaction', Biochem. Eng. J., , 37, 159-165 (2007), 2007.08.
219. T. Maruyama, K. Nakashima, F. Kubota, M. Goto, Perfluorocarbon-based liquid-liquid extraction for separation of transition metal ions., , Anal. Sci., , 23, 763-765 (2007), 2007.07.
220. H. Yoshiura, M. Hashida, N. Kamiya, and M. Goto, , Factors affecting protein release behavior from surfactant-protein complexes under physiological conditions. , Int. J. Pharm. , 228, 654-658 (2007), 2007.06.
221. J. Tominaga, N. Kamiya and M. Goto, , An enzyme-labeled protein polymer bearing pendant haptens. , Bioconjugate Chem. , 18, 860-865 (2007), 2007.05.
222. M. Kukizaki, M. Goto, Spontaneous formation behavior of uniform-sized microbubbles from Shirasu porous glass (SPG) membranes in the absence of water-phase flow. , COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS , 296(1-3) 174-181 (2007), 2007.05.
223. M. Kukizaki, M. Goto, Preparation and evaluation of uniformly sized solid lipid microcapsules using membrane emulsification, COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS , 293(1-3), 87-94 (2007), 2007.05.
224. K. Shimojo, H. Naganawa, J. Noro, F. Kubota, and M. Goto, , Extraction Behavior and Separation of Lanthanides with a Diglycol Amic Acid Derivative and a Nitrogen-donor Ligand., , Anal. Sci., , 23, 1427-1430 (2007), 2007.05.
225. J. Tominaga, Y. Kemori, Y. Tanaka, T. Maruyama, N. Kamiya and M. Goto, An enzymatic method for site-specific labeling of recombinant proteins with oligonucleotides. , Chem. Commun., 401-403 (2007), 2007.04.
226. T. Maruyama, H. Matsushita, Y. Shimada, I. Kamata, M. Hanaki, S. Sonokawa, N. Kamiya, M. Goto, Proteins and protein-rich biomass as environmental-friendly adsorbents selective for precious metal ions. , Environ. Sci. Technol. , 41(4),1359-1364 (2007), 2007.04.
227. H. Piao, N. Kamiya, A. Hirata, H. Yokoyama, T. Fujii, I. Shimizu, S. Ito, M. Goto, , Reduction of gastric ulcerogenicity during multiple administration of diclofenac sodium by a novel solid-in-oil suspension. , Pharmaceutical Development and Technology, , 322, 312-316(2007), 2007.04.
228. Yusuke Tanaka, Yukito Tsuruda, Motohiro Nishi, Noriho Kamiya, Masahiro Goto, 'Exploring Enzymatic Catalysis at a Solid Surface: A Case Study with Transglutaminase-Mediated Protein Immobilization.', Org. Biomol. Chem., , 5, 1764-1770 (2007), 2007.04.
229. F. Kubota, Y. Koyanagi, K. Nakashima, K. Shimojo, N. Kamiya and M. Goto, , Extraction of Cytochrome c by a Functionalized Ionic Liquid Containing a Crown Ether, Solv. Extr. Res. & Devel. Japan, , 14, 115-120 (2007), 2007.04.
230. J. Tominaga, Y. Kemori, Y. Tanaka, T. Maruyama, N. Kamiya and M. Goto, An enzymatic method for site-specific labeling of recombinant proteins with oligonucleotides. , Chem. Commun., 401 - 403 (2007), 2007.03.
231. T. Maruyama, H. Matsushita, Y. Shimada, I. Kamata, M. Hanaki, S. Sonokawa, N. Kamiya, M. Goto, , Proteins and protein-rich biomass as environmental-friendly adsorbents selective for precious metal ions. , Environ. Sci. Technol. , 41, 1356-1364 (2007), 2007.03.
232. J. Tominaga, N. Kamiya and M. Goto, An enzyme-labeled protein polymer bearing pendant haptens. , Bioconjugate Chem, 18, 860-865 (2007), 2007.03.
233. S. Egusa, T. Kitaoka, M. Goto, H. Wariishi, Synthesis of Cellulose In Vitro by Using a Cellulase/Surfactant Complex in a Nonaqueous Mediumc, Angew. , Chem. Int. Edit., 46(12), 2063-2065, (2007), 2007.03.
234. T. Maruyama, C. Komatsu, J. Michizoe, S. Sakai and M. Goto, , Laccase-mediated degradation and reduction of toxicity of the postharvest fungicide imazalil. , Process Biochem., 42, 459-461 (2007), 2007.03.
235. T. Maruyama, S. Sonokawa, H. Matsushita and M. Goto, Inhibitiory effects of gold(III) ions on ribonuclease and deoxyribonuclease. , J. Inorg. Biochem. , 101, 180-186 (2007), 2007.02.
236. T. Maruyama, C. Komatsu, J. Michizoe, S. Sakai and M. Goto, Laccase-mediated degradation and reduction of toxicity of the postharvest fungicide imazalil. , Process Biochem, 42, 459-461 (2007), 2007.01.
237. M. Kukizaki, and M. Goto, Effects of Interfacial Tension and Viscosities of Oil and Water Phases on Monodispersed Droplet Formation Using a Shirasu-Porous-Glass (SPG) Membrane., Membrane, 31, 215-220 (2006), 2006.12.
238. M. Kukizaki, M. Goto, Size control of nanobubbles generated from Shirasu-porous-glass (SPG) membranes. , J. Membr. Sci, 281, 386-396 (2006), 2006.12.
239. K. Shimojo, N. Kamiya, F. Tani, H. Naganawa, Y. Naruta and M. Goto, Extractive Solubilization, Structural Change, and Functional Conversion of Cytochrome c in Ionic Liquids via Crown Ether Complexation. , Anal. Chem., 78, 7735-7742 (2006), 2006.11.
240. N. Othman, H. Mat, M. Goto, Separation of silver from photographic wastes by emulsion liquid membrane system. , JOURNAL OF MEMBRANE SCIENCE , 282, 171-177 (2006), 2006.11.
241. K. Nakashima, J. Okada, T. Maruyama, N. Kamiya, M. Goto, Activation of lipase in ionic liquids by modification with comb-shaped poly(ethylene glycol), Sci. Technol. Adv. Mater, 7, 692-698 (2006), 2006.10.
242. K. Nakashima, T. Maruyama, N. Kamiya, M. Goto, Homogeneous Enzymatic Reactions in Ionic Liquids with Poly(ethylene glycol)-Modified Subtilisin. , Org. Biomol. Chem, 4, 3462-3467 (2006). , 2006.09.
243. M Goto, H Kawakita, K Uezu, S Tsuneda, K Saito, M Goto, M Tamada, T Sugo, Esterification of Lauric Acid Using Lipase Immobilized in the Micropores of a Hollow-Fiber Membrane. , J Amer Oil Chemists' Soc, , 83, 209-213 (2006), 2006.08.
244. M. Shinshi, Takayasu Sugihara, T. Osakai, M. Goto, Electrochemical Extraction of Proteins by Reverse Micelle Formation. , Langmuir, 22, 5937-5944 (2006). , 2006.07.
245. T Mouri, N Kamiya, M Goto, Increasing the catalytic performance of a whole cell biocatalyst harboring a cytochrome P450cam system by stabilization of an electron transfer component. , Biotechnol. Lett, 28, 1509-1513 (2006), 2006.07.
246. K. Shimojo, H. Naganawa, F. Kubota, M. Goto, Solvent Extraction of Lanthanides into an Ionic Liquid Containing N, N, N', N'-tetrakis(2-pyridylmethyl)ethylenediamine. , Anal Biochem , 35, 484-485 (2006)., 2006.06.
247. H. Piao, N Kamiya, J Watanabe, H Yokoyama, A Hirata, T Fujii, I Shimizu, S Ito, M Goto, Oral delivery of diclofenac sodium using a novel solid-in-oil suspension, Int. J. Pharm, 313, 159-162 (2006), 2006.06.
248. N. Othman, C-K. Hie, M. Goto, H. Mat, Emulsion liquid membrane extraction of silver from photographic waste using CYANEX 302 as the mobile carrier. , Solv. Extr. Res. Dev. Jpn, 13, 191-202 (2006). , 2006.06.
249. T. Maruyama, C. Komatsu, J. Michizoe, H. Ichinose and M. Goto, Laccase-mediated oxidative degradation of the herbicide dymron. , Biotechnol Prog, 22, 426-430 (2006). , 2006.05.
250. T. Ono, M. Goto, Peroxidative catalytic behavior of cytochrome c solubilized in reverse micelles, Biochem. Eng. J., 28, 156-160 (2006)., 2006.05.
251. T. Maruyama, T. Shinohara, T. Hosoki, H. Ichinose, N. Kamiya and M. Goto, Masking oligonucleotides improve sensitivity of mutation detection based on guanine quenching. , Anal Biochem , 354, 8-14 (2006). , 2006.05.
252. F. Kubota, H. Yamada, M. Goto, S. Furusaki, Extraction of adenosine nucleotides by a long-chain quaternary ammonium salt, Solv. Extr. Res. Dev. Jpn, 13, 107-114 (2006). , 2006.05.
253. K. Shimojo, K. Nakashima, N. Kamiya, M. Goto, Crown Ether-Mediated Extraction and Functional Conversion of Cytochrome c in Ionic Liquids, Biomacromolecules, Vol.7, 2-6 (2006), 2006.04.
254. T. Mouri, J. Michizoe, H. Ichinose, N. Kamiya, and M. Goto, A recombinant Escherichia coli whole cell biocatalyst harboring a cytochrome P450cam monooxygenase system coupled with enzymatic cofactor regeneration. , Appl. Microbiol. biotechnol, 72, 514-520 (2006), 2006.04.
255. H Ichinose, M Kitaoka, N Okamura, T Maruyama, N Kamiya, M Goto, Detection of single-base mutations by fluorogenic ribonuclease protection (FRAP) assay, Anal Chem, 10.1021/ac050782k, 77, 21, 7047-7053, 77, 7047-7053 (2005), 2005.10.
256. K. Nakashima, T. Maruyama, N. Kamiya, M. Goto, Comb-shaped poly(ethylene glycol)-modified subtilisin Carlsberg is soluble and highly active in ionic liquids, Chem. Commun, 10.1039/b505479f, 34, 4297-4299, 4297-4299 (2005), 2005.09.
257. T. Oshima, H. Higuchi, K. Ohto, K. Inoue, M. Goto, Selective Extraction and Recovery of Cytochrome c by Liquid-Liquid Extraction Using a Calix[6]arene Carboxylic Acid Derivative, Langmuir,, 10.1021/la050364a, 21, 16, 7280-7284, 21, 7280-7284 (2005), 2005.09.
258. J. Michizoe, H. Ichinose, N. Kamiya, T. Maruyama, M. Goto, Functionalization of the Cytochrome P450cam Monooxygenase System in the Cell-like Aqueous Compartments of Water-in-Oil Emulsions, J. Biosci. and Bioeng, 10.1263/jbb.99.012, 99, 1, 12-17, 99巻、第1号、145-152, 2005.02.
259. E. Miyako, T. Maruyama, N. Kamiya, M. Goto, A supported liquid membrane encapsulating a surfactant-lipase complex for selective separation of organic acids, Chem Eur J, 10.1002/chem.200400691, 11, 4, 1163-1170, 11, 1163-1170 (2005)., 2005.01.
260. E. Toorisaka, H. Ono, K. Arimori, N. Kamiya, M. Goto, Hypoglycemic effect of surfactant-coated insulin solubilized in a novel solid-in-oil-in-water (S/O/W) emulsion, Int. J. Pharm, 10.1016/S0378-5173(02)00674-9, 252, 1-2, 271-274, 252, 271-274 (2003), 2003.12.
261. E. Miyako, T. Maruyama, N. Kamiya, and M. Goto, Enantioselective transport of (S)-ibuprofen through a lipase-facilitated supported liquid membrane based on ionic liquids, Chem Commun, 2926-2927 (2003)., 2003.12.
262. Development of Microbioreactor for biodegradation of organic pollutants.
263. L.C. Park, T. Maruyama, M. Goto, DNA hybridization in reverse micelles and its application to mutation detection, Analyst, 10.1039/b208755n, 128, 2, 161-165, 128, 161-165 (2003)., 2003.06.
264. Masahiro Goto, Fumiyuki Nakashio, Development of new surfactants for liquid surfactant membrane process, J. Chem. Eng. Japan, 10.1252/jcej.20.157, 20, 2, 157-164, Vol. 20, No. 2, 157 - 164, 1987.06.