Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
Masahiro Goto Last modified date:2019.07.26

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


Papers
1. 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..
2. 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..
3. 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..
4. 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..
5. 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
1
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..
6. 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..
7. 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..
8. 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
1
and f
2
) 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..
9. 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..
10. 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
1
H and
13
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
0

m
, ΔH
0

m
, and ΔS
0

m
)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..
11. 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..
12. 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..
13. 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..
14. 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..
15. 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..
16. 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..
17. 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
-3
NaClO
4
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..
18. 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
2
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
2
O
2
. The addition of H
2
O
2
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..
19. 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..
20. 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..
21. 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..
22. 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..
23. 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
6
]), 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
6
] 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..
24. 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..
25. 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.
26. 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..
27. 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..
28. 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..
29. 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..
30. 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..
31. 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..
32. 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..
33. 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..
34. 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..
35. 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..
36. 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..
37. 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..
38. 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..
39. 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..
40. 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..
41. 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..
42. 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..
43. 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..
44. 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..
45. 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.
46. 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.
47. 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.
48. 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.
49. 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.
50. 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.
51. 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.
52. 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.
53. 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.
54. 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.
55. 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.
56. 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.
57. 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.
58. 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.
59. 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.
60. 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.
61. 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.
62. 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。.
63. 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.
64. 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.
65. 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.
66. 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.
67. 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.
68. 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.
69. 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.
70. 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.
71. Kojiro Shimojo, Masahiro Goto, Highly Efficient Extraction Separation of Lanthanides Using a Diglycolamic Acid Extractant, ANALYTICAL SCIENCES, 30, 2, 263-269, 2014.02.
72. 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.
73. 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.
74. 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.
75. 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.
76. 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.
77. 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.
78. 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.
79. 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.
80. 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.
81. Yukiho Hosomomi, Fukiko Kubota, Masahiro Goto, Biosorption of Rare Earth Elements by Escherichia coli, J. Chem. Eng. Japan, 46, 7, 450-454, 2013.09.
82. 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.
83. Atsuomi Shundo, Masahiro Goto, Keiji Tanaka, Spatial Heterogeneity in the Sol-gel Transition of a Supramolecular System, Soft Matter,, 9, 5166-5172, 2013.07.
84. 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.
85. 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.
86. 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.
87. 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.
88. 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。.
89. 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.
90. 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.
91. 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.
92. 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.
93. 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.
94. 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.
95. 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.
96. 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.
97. 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.
98. 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.
99. 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.
100. 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.
101. 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.
102. 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.
103. 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.
104. 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.
105. 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.
106. 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.
107. 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.
108. 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.
109. 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.
110. 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.
111. 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.
112. Kojiro Shimojo, Masahiro Goto, Noriho Kamiya, Facile, rapid and efficient biofabrication of gold nanoparticles decorated with functional proteins, Analyst., 137, 2300-2303, 2012.07.
113. 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.
114. 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.
115. 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.
116. Masahiro Goto, Josui Shimada, Noriho Kamiya, Programmable protein protein conjugation via DNA-based self-assembly, Chem. Commun, 48, 6226-6228, 2012.05.
117. 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.
118. Uju, Masahiro Goto, Noriho Kamiya, Short time ionic liquids pretreatment on lignocellulosic biomass to enhance enzymatic saccharification, Bioresour. Technol., 103, 446-452, 2012.05.
119. Eiichi Toorisaka, Masahiro Goto, Intestinal patches with an immobilized solid-in-oil formulation for oral protein delivery, Acta Biomaterialia, 8, 653-658, 2012.04.
120. 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.
121. 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.
122. 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.
123. 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.
124. 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.
125. A. Shundo, K. Mizuguchi, M. Miyamoto, M. Goto, K. Tanaka, Controllable Heterogeneity in a Supramolecular Hydrogel, Chem. Commun., 47, 31, 8844-8846, 2011.07.
126. 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.
127. 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.
128. 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.
129. 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.
130. 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.
131. 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.
132. 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.
133. 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.
134. 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.
135. 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.
136. 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.
137. 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.
138. 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.
139. 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.
140. 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.
141. 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.
142. H. Abe, M. Goto, N. Kamiya, Enzymatic single-step preparation of multifunctional proteins, Chem. Commun., 33, 213-215, 2010.08.
143. 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.
144. 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.
145. 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.
146. 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.
147. 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.
148. 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.
149. 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.
150. 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.
151. 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.
152. 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.
153. 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.
154. 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.
155. 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.
156. 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.
157. 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.
158. 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.
159. 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.
160. 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.
161. 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.
162. 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.
163. 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.
164. 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.
165. 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.
166. 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.
167. 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.
168. 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.
169. 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.
170. 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.
171. 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.
172. 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.
173. 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.
174. 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.
175. 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.
176. 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.
177. 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.
178. 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.
179. 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.
180. 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.
181. 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.
182. 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.
183. 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.
184. 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.
185. 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.
186. T. Maruyama, T. Hosogi, M. Goto, Sequence-selective extraction of single-stranded DNA using DNA-functionalized reverse micelles. , Chem. Commun. , 4450 (2007) , 2007.08.
187. 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.
188. K. Shimojo, T. Oshima, H. Naganawa, M. Goto, "Calixarene-Assisted Protein Refolding via Liquid-Liquid Extraction", , Biomacromolecules,, 8, 3061-3066 (2007), 2007.10.
189. 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.
190. 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.
191. 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.
192. 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.
193. 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.
194. 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.
195. J. Tominaga, N. Kamiya and M. Goto, , An enzyme-labeled protein polymer bearing pendant haptens. , Bioconjugate Chem. , 18, 860-865 (2007), 2007.05.
196. 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.
197. 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.
198. 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.
199. 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.
200. 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.
201. 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.
202. J. Tominaga, N. Kamiya and M. Goto, An enzyme-labeled protein polymer bearing pendant haptens. , Bioconjugate Chem, 18, 860-865 (2007), 2007.03.
203. 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.
204. 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.
205. 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.
206. 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.
207. 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.
208. 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.
209. M. Kukizaki, M. Goto, Size control of nanobubbles generated from Shirasu-porous-glass (SPG) membranes. , J. Membr. Sci, 281, 386-396 (2006), 2006.12.
210. 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.
211. 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.
212. 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.
213. 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.
214. 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.
215. 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.
216. M. Shinshi, Takayasu Sugihara, T. Osakai, M. Goto, Electrochemical Extraction of Proteins by Reverse Micelle Formation. , Langmuir, 22, 5937-5944 (2006). , 2006.07.
217. 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.
218. 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.
219. 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.
220. 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.
221. T. Ono, M. Goto, Peroxidative catalytic behavior of cytochrome c solubilized in reverse micelles, Biochem. Eng. J., 28, 156-160 (2006)., 2006.05.
222. 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.
223. 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.
224. 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.
225. 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.
226. 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.
227. 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.
228. 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.
229. 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.
230. 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.
231. 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.
232. 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.
233. 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.
234. Development of Microbioreactor for biodegradation of organic pollutants.