生物機能ならびに生物材料を利用した高性能イオン交換材料の開発に関して、これまで発表した４００編以上の業績が認められ、日本イオン交換学会の学会賞が授与された。

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DOI： 10.1002/cben.202300051

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DOI： 10.1016/j.foodchem.2023.136911

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DOI： 10.21203/rs.3.rs-3338523/v1

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DOI： 10.1002/tcr.202300026

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DOI： 10.1021/acsami.3c03900

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Japan Association of Solvent Extraction  

<p>Recycling platinum group metals from secondary resources such as spent automotive exhaust catalysts is promising for the circular economy. However, the selective separation of Pt over massive amounts of impurity metals such as Mg and Al is particularly challenging. In this study, non-aqueous direct leaching of platinum from a spent automotive catalyst (SAC) using hydrophobic ionic liquids, namely, trihexyl(tetradecyl)phosphonium chloride (P₆₆₆₁₄Cl) and trioctyl(dodecyl)phosphonium chloride (P₈₈₈₁₂Cl) with the aid of pre-loading hydrochloric acid/hydrogen peroxide was proposed. The more hydrophobic P₈₈₈₁₂Cl exhibited more efficient and selective leaching of Pt over Mg and Al. The recovery of Pt from the metal-loaded P₈₈₈₁₂Cl, and the reusability of the IL for SAC leaching were also demonstrated. </p>

DOI： 10.15261/serdj.30.149

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DOI： 10.3390/pr11041112

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DOI： 10.3390/molecules28072969

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DOI： 10.3390/molecules28052345

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DOI： 10.1016/j.hydromet.2023.106024

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DOI： 10.3390/pharmaceutics15041179

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DOI： 10.3390/molecules28072969

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Malaria is a mosquito-borne infectious disease that is widespread in developing countries. Malaria vaccines are important in efforts to eradicate malaria; however, vaccines are usually administered by injection, which requires medical personnel and has a risk of causing infection. Transdermal vaccines can be administered without damaging the skin and thus are ideal for the prevention of malaria. However, the stratum corneum forms a "brick and mortar" like structure in which stratum corneum cells are embedded in a hydrophobic matrix composed of lipids, which strongly inhibits the permeation of hydrophilic substances. In the present study, we designed a transdermal vaccine against vivax malaria using a solid-in-oil (S/O) dispersion. The S/O dispersion of a transmission blocking vaccine candidate, Pvs25 from Plasmodium vivax, showed higher skin penetration than that of the aqueous solution. Mice immunized with the S/O dispersion generated antibodies at similar titers as the mice immunized by injection, over the mid- to long-term. These results provide information for the development of transdermally administered malaria vaccines toward the eradication of malaria.

DOI： 10.1016/j.xphs.2022.10.031

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acsomega.2c06654

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The transdermal delivery of hydrophilic drugs remains challenging owing to their poor ability to permeate the skin; formulation with oil media is difficult without adding chemical permeation enhancers or co-solvents. Herein, we synthesized 12 oil-miscible ionic liquid (IL) drugs comprising lidocaine-, imipramine-, and levamisole (Lev)-hydrochloride with fatty acid permeation enhancers, i.e., laurate, oleate, linoleate, and stearate as counterions. A set of in vitro and in vivo studies was performed to investigate the potency and deliverability of the transdermal drug formulations. All of the synthesized compounds were freely miscible with pharmaceutically acceptable solvents/agents (i.e., ethanol, N-methyl pyrrolidone, Tween 20, and isopropyl myristate (IPM)). In vitro permeation studies revealed that the oleate-based Lev formulation had 2.6-fold higher skin permeation capability than the Lev salts and also superior ability compared with the laurate-, linoleate-, and stearate-containing samples. Upon in vivo transdermal administration to mice, the peak plasma concentration, elimination half-life, and area under the plasma concentration curve values of Lev-IL were 4.6-, 2.9-, and 5.4-fold higher, respectively, than those of the Lev salt. Furthermore, in vitro skin irritation and in vivo histological studies have demonstrated that Lev-IL has excellent biocompatibility compared with a conventional ionic liquid-based carrier. The results indicate that oil-miscible IL-based drugs provide a simple and scalable strategy for the design of effective transdermal drug delivery systems.

DOI： 10.1021/acsami.2c15636

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DOI： 10.1016/j.molliq.2022.120151

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Language：Others   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.bej.2022.108690

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DOI： 10.1021/acssuschemeng.2c03480

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

Transdermal drug delivery systems (TDDSs) may be useful for preventing various diseases including cancer. However, the stratum corneum (SC) inhibits the permeation of foreign particles into the skin. To obtain an effective TDDS, we developed a protein-containing nanocarrier (PCNC) comprising an antigenic protein (ovalbumin/OVA) stabilized by a combination of surfactants, i.e., a lipid-based surface-active ionic liquid and Tween-80. The PCNC was lyophilized to remove water and cyclohexane and then dispersed in isopropyl myristate. It is biocompatible both in vitro and in vivo, and is suitable for use in a therapeutic TDDS. The skin permeability of the PCNC was significantly (p < 0.0001) enhanced, and the transdermal distribution and transdermal flux of the OVA delivery system were 25 and 28 times greater, respectively, than those of its aqueous formulation. The PCNC disrupted the order of lipid orientation in the skin's SC and increased intercellular protein delivery. It demonstrated effective antitumor activity, drastically (p < 0.001) suppressed tumor growth, increased mouse survival rates, and significantly (p < 0.001) stimulated the OVA-specific tumor immune response. The PCNC also increased the number of cytotoxic T cells expressing CD8 antibodies on their surfaces (CD8 + T-cells) in the tumor microenvironment. These findings suggest that PCNCs may be promising biocompatible carriers for transdermal antigenic protein delivery in tumor immunotherapy.

DOI： 10.1021/acsabm.2c00061

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

Hydrophobic eutectic solvents composed of synergistic metal ligands were utilized for recycling cathode materials of lithium-ion batteries as alternatives to inorganic acids and organic solvents in conventional hydrometallurgical cathode recycling.

DOI： 10.1039/D1GC04846E

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Language：Others   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.iecr.2c00295

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DOI： 10.1016/j.biomaterials.2022.121385

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DOI： 10.1016/j.molliq.2021.118103

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER  

To establish more efficient and environmentally friendly lithium-ion battery (LiB) recycling processes, novel extractants derived from amino acids that enable better separation of Ni and Co were explored using density functional theory (DFT) calculations. DFT calculations and experimental validation indicated that of the three coordination sites-namely amine, amide, and carboxyl groups in the amic-acid ligands-the bond strength of the central amine group to the metal determines the Ni and Co separation performance. Based on the findings, the glycine-derived amic-acid extractant N-[N,N-di(2-ethylhexyl)aminocarbonylmethyl]glycine (D2EHAG) was applied for the recovery of Ni and Co from a spent automotive LiB leachate. Preferential and mutual recovery of Ni and Co from manganese by the D2EHAG-based recycling process was demonstrated. This study provides insights into the design of extractants that enable the mutual separation of Ni, Co, and Mn, and indicates the suitability of amic-acid extractants for LiB recycling processes.

DOI： 10.1016/j.seppur.2021.119898

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Transcutaneous drug delivery is a promising method in terms of drug repositioning and reformulation because of its non-invasive and easy-to-use features. To overcome the skin barrier, which is the biggest challenge in transcutaneous drug delivery, a number of techniques, such as microemulsion, solid-in-oil dispersions and liposomes, have been studied extensively. However, the low viscosity of these formulations limits drug retention on the skin and reduces patient acceptability. Although viscosity can be increased by adding a thickening reagent, such an addition often alters formulation nanostructures and drug solubility, and importantly, decreases skin permeability. In this study, a gel-like lyotropic liquid crystal (LLC) was used as a tool to enhance skin permeability. In particular, we prepared 1-monolinolein (ML)-based LLCs with different water contents. All LLCs significantly enhanced skin permeation of a peptide drug, an epitope peptide of melanoma, despite their high viscoelasticity. Fourier transform infra-red spectroscopic analysis of the skin surface treated with the LLCs revealed that the gyroid geometry more strongly interacted with the lamellar structure inside the stratum corneum (SC) than the diamond geometry. Finally, as the result of the in vivo tumor challenge experiment using B16F10 melanoma-bearing mice, the LLC with the gyroid geometry showed stronger vaccine effect against tumor than a subcutaneous injection. Collectively, ML-based LLCs, especially with the gyroid geometry, are a promising strategy to deliver biomacromolecules into skin. Statement of significance: Transcutaneous drug delivery is a promising method for drug repositioning and reformulation because of its non-invasive and easy-to-use features. To overcome the skin barrier, which is the biggest challenge in transcutaneous drug delivery, we used a gel-like lyotropic liquid crystal (LLC) as a novel tool to enhance skin permeability. In this paper, we demonstrated that an LLC with a specific liquid crystalline structure has the highest skin permeation enhancement effect for a peptide antigen as a model drug. Moreover, the peptide antigen-loaded LLC showed a vaccine effect that was comparable to a subcutaneous injection in vivo. This study provides a basis for designing a transcutaneous delivery system of peptide drugs with LLC.

DOI： 10.1016/j.actbio.2021.11.008

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DOI： https://doi.org/10.1016/j.molliq.2021.118103

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DOI： 10.1021/acsami.1c11533

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DOI： 10.1021/acs.molpharmaceut.1c00324

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DOI： 10.1021/acsabm.1c00563

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DOI： 10.1021/acsami.1c03111

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DOI： 10.1016/j.ijpharm.2021.120582

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DOI： https://doi.org/10.1016/j.ejps.2020.105667

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DOI： 10.1016/j.ejps.2020.105667

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Other Link： https://doi.org/10.1016/j.ejps.2020.105521

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Other Link： https://doi.org/10.1016/j.molliq.2020.114424

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Other Link： https://doi.org/10.1039/d0cc04491a

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DOI： 10.1021/acs.molpharmaceut.0c00598

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Other Link： https://doi.org/10.1016/j.molliq.2020.113603

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DOI： 10.3390/COSMETICS7030052

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Other Link： https://doi.org/10.3390/pharmaceutics12090814

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Other Link： https://dx.doi.org/10.1021/acssuschemeng.0c03419

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Other Link： https://doi.org/10.1021/acssuschemeng.0c03205

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DOI： 10.1016/j.ijpharm.2020.119335

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Other Link： https://dx.doi.org/10.1021/acsomega.0c00867

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DOI： 10.3390/pharmaceutics12040392

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Other Link： https://doi.org/10.1021/acssuschemeng.9b07773

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An allergy to cow’s milk proteins is the most common food allergy in infants and toddlers. Conventional oral immunotherapy for cow’s milk allergies requires hospital admission due to the risk of severe allergic reactions, including anaphylaxis. Therefore, a simpler and safer immunotherapeutic method is desirable. We examined transcutaneous immunotherapy with a solid-in-oil (S/O) system. In the S/O system, nano-sized particles of proteins are dispersed in an oil-vehicle with the assistance of nonionic surfactants. In the present study, the S/O system enhanced the skin permeation of the allergen molecule β-lactoglobulin (BLG), as compared with a control PBS solution. The patches containing BLG in the S/O nanodispersion skewed the immune response in the allergy model mice toward T helper type 1 immunity, indicating the amelioration of allergic symptoms. This effect was more pronounced when the immunomodulator resiquimod (R-848) was included in the S/O system.

DOI： 10.3390/pharmaceutics12030205

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DOI： 10.3390/pharmaceutics12030240

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DOI： 10.1016/j.molliq.2019.112166

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DOI： 10.1021/acs.molpharmaceut.9b01104

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DOI： 10.1016/j.bej.2019.107426

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DOI： 10.1021/acsomega.9b02540

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DOI： 10.1016/j.ijpharm.2019.118777

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DOI： 10.1021/acs.iecr.9b05183

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DOI： 10.3390/pharmaceutics11110563

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Ionic liquid (IL)surfactants have attracted great interest as promising substitutes for conventional surfactants owing to their exceptional and favorable physico-chemical properties. However, most IL surfactants are not eco-friendly and form unstable micelles, even when using a high concentration of the surfactant. In this study, we prepared a series of halogen-free and biocompatible choline–fatty-acid-based ILs with different chain lengths and degrees of saturation, and we then investigated their micellar properties in aqueous solutions. Characterization of the synthesized surface-active ILs (SAILs)was performed by
H and C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, differential scanning calorimetry, and elemental analysis. The surface-active properties of the SAILs were investigated by tensiometry, conductometry, and dynamic light scattering measurements. The critical micelle concentration of the SAILs was found to be 2–4 times lower than those of conventional surfactants. The thermodynamic properties of micellization (ΔG 0m, ΔH 0m, and ΔS 0m)indicate that the micellization process of the SAILs is spontaneous, stable, and entropy-driven at room temperature. The cytotoxicity of the SAILs was evaluated using mammalian cell line NIH 3T3. Importantly, [Cho][Ole]shows lower toxicity than the analogous ILs with conventional surfactants. These results clearly suggest that these environmentally friendly SAILs can be used as a potential alternative to conventional ILs for various purposes, including biological applications.

DOI： 10.1016/j.jcis.2019.04.095

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DOI： 10.1016/j.ijpharm.2019.05.020

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DOI： 10.1016/j.molliq.2019.02.049

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DOI： 10.1172/JCI97642

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DOI： 10.1016/j.molliq.2019.01.063

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DOI： 10.1021/acs.iecr.8b05848

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DOI： 10.1016/j.memsci.2018.11.021

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DOI： 10.2116/analsci.18N020

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DOI： 10.1039/C8CC08163H

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DOI： 10.1252/jcej.18we175

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DOI： 10.1021/acsbiomaterials.9b00260

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DOI： 10.1002/biot.201800085

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DOI： 10.1080/07366299.2018.1532139

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DOI： 10.1016/j.molliq.2018.06.101

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DOI： 10.1021/acs.molpharmaceut.8b00305

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DOI： 10.1002/jctb.5544

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DOI： 10.1016/j.ijpharm.2018.05.021

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DOI： 10.1021/acs.molpharmaceut.7b00894

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DOI： 10.1016/j.colsurfb.2018.01.041

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DOI： 10.1039/9781788011839-00390

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DOI： 10.1021/acs.bioconjchem.7b00594

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DOI： 10.1007/978-4-431-56526-0_18

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DOI： 10.1016/j.molliq.2017.08.020

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DOI： 10.1016/j.ijpharm.2017.07.020

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DOI： 10.1021/acs.biomac.6b01538

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DOI： 10.1016/j.cjche.2016.06.002

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DOI： 10.1002/biot.201600081

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DOI： 10.1016/j.proeng.2016.06.464

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DOI： 10.1016/j.bej.2016.06.005

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DOI： 10.1002/jctb.4725

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DOI： 10.1016/j.bej.2016.01.021

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DOI： 10.1208/s12249-015-0333-x

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DOI： 10.1016/j.biombioe.2015.05.023

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DOI： 10.1039/c5md00168d

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DOI： 10.1007/s11095-014-1554-5

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DOI： 10.1039/c5md00378d

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DOI： 10.1021/ja510156v

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DOI： 10.1016/j.carbpol.2014.05.003

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DOI： 10.1039/c4ra08897b

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DOI： 10.1016/j.procbio.2014.02.016

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DOI： 10.1039/c4ra02901a

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DOI： 10.1021/ie403524a

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DOI： 10.1016/j.ijpharm.2013.10.006

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DOI： 10.1016/j.jhazmat.2013.03.026

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DOI： 10.1016/j.biortech.2012.06.096

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DOI： 10.1016/j.ejpb.2012.05.016

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Enzyme-Mediated Protein Refolding

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Proteinase-mediated drastic morphological change of peptide-amphiphile to induce supramolecular hydrogelation

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Ionic liquid-assisted transdermal delivery of sparingly soluble drugs

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A Comparative Study of SPG Membrane Emulsification in the Presence and Absence of Continuous-Phase Flow

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Preparation of Lactose-Modified Cellulose Films by a Nonaqueous Enzymatic Reaction and their Biofunctional Characteristics as a Scaffold for Cell Culture

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Simultaneous visual detection of single-nucleotide variations in tuna DNA using DNA/RNA chimeric probes and ribonuclease A

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Extraction Behavior of Indium with TOPO into Ionic Liquids

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Development of a novel immobilization method for enzymes from hyperthermophiles

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Design of a cytochrome P450BM3 reaction system linked by two-step cofactor regeneration catalyzed by a soluble transhydrogenase and glycerol dehydrogenase

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"Spectrophotometric Assay for Protease Activity in Ionic Liquids Using Chromogenic Substrates".

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CO2 separation facilitated by task-specific ionic liquids using a supported liquid membrane

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Formation of Reverse Micelles in a Room-Temperature Ionic Liquid

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DOI： 10.1021/ac050782k

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DOI： 10.1039/b505479f

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DOI： 10.1021/la050364a

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DOI： 10.1002/chem.200400691

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Hypoglycemic effect of surfactant-coated insulin solubilized in a novel solid-in-oil-in-water (S/O/W) emulsion

DOI： 10.1016/S0378-5173(02)00674-9

Language：English   Publishing type：Research paper (scientific journal)  

Enantioselective transport of (S)-ibuprofen through a lipase-facilitated supported liquid membrane based on ionic liquids

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

DNA hybridization in reverse micelles and its application to mutation detection

DOI： 10.1039/b208755n

Language：English   Publishing type：Research paper (scientific journal)  

Novel surfactant for liquid surfactant membrane processes

DOI： 10.1252/jcej.20.157

Publisher：Green Chemistry  

Deep eutectic solvents (DESs) composed of a beta-diketone and phosphine oxides featuring different alkyl chain lengths were prepared and then employed as liquid-liquid extraction and dissolution media for the separation of iron, cobalt, neodymium, and dysprosium. In the dissolution the more sterically hindered DESs exhibited enhanced selectivity to neodymium, which was poorly separated using liquid-liquid extraction. The dissolution selectivity in less sterically hindered DESs could be controlled by the addition of organic acids with different alkyl chain lengths.

DOI： 10.1039/d4gc01089b

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Publisher：Journal of Molecular Liquids  

Quinine has traditionally been used in medicine to treat parasitic disease malaria due to its antimalarial activities. It is sparingly soluble in water and highly soluble in organic solvents. However, these solvents are not environmentally friendly, so greener solvents need to be explored and designed. Ionic liquids (ILs) were successfully observed to be greener and capable of dissolving biologically active compounds. However, finding a potential IL from millions of possible IL combinations is challenging. This work utilizes the conductor-like screening model for real solvents (COSMO-RS) to address this issue. This study aims to determine the dissolution behavior of quinine in ILs employing the COSMO-RS. A total of 540 IL combinations of 9 cations and 60 anions were investigated. The efficacy of each IL was evaluated by predicting the activity coefficients at infinite dilution, solvation-free energy, selectivity, capacity, and performance index (P.I.). This study reveals that ILs with shorter alkyl chains, polar and non-aromatic characteristics, and smaller anions are advantageous for the solubility enhancement of quinine. The most effective ILs, choline acetate, choline glycinate, and choline threoninate, displayed the highest selectivity, capacity, P.I., and lowest activity coefficient and solvation-free energies. The findings of the current study unlock key insights into the solubility behaviour of quinine in an aqueous solution employing ILs.

DOI： 10.1016/j.molliq.2024.125388

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Publisher：Fisheries Science  

Ulva is an unutilized green seaweed that grows in the intertidal zone around the coast of Java Island, Indonesia. In this study, U. lactuca samples collected from three regions in south of Java Island (Cihara, Surade, and Tepus) were studied in terms of their chemical composition, physical properties and its bioactivity, to determine the best regions for establishing seaweed industries. The chemical characteristics differed significantly among different regions, where the seaweed from Tepus, Surade and Cihara had the highest content of protein (22.93%), carbohydrate (61.58%), and mineral (28.72%), respectively. The amino acids were dominated with L-aspartic acid and L-glutamic acid. All U. lactuca samples contained abundant pigments, such as chlorophylls and carotenoids, especially samples from Tepus. The highest content of crude ulvan was found in Surade seaweed (26.9%). Chemical and physical analyses showed the presence of S = O and C–O–S functional groups in ulvan, a sulfated polysaccharide unique to Ulva sp., with thermal degradation up to 220 °C. Crude ulvan from Surade and Tepus seaweed exhibited bioactivity to support proliferation of fibroblast cells at 100 and 1000 ppm, respectively. Based on the properties of U. lactuca, Tepus and Surade were identified as potential sites to establish aquaculture and/or processing industries.

DOI： 10.1007/s12562-024-01799-6

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Language：English   Publisher：Environmental Technology (United Kingdom)  

In the present investigation, a total of 108 combinations of ionic liquids (ILs) were screened using the conductor-like screening model for real solvents (COSMO-RS) with the aid of six cations and eighteen anions for the extraction of succinic acid (SA) from aqueous streams through dispersive liquid–liquid microextraction (DLLME). Using the screened ILs, an ionic liquid-based DLLME (IL-DLLME) was developed to extract SA and the role of different reaction parameters in the effectiveness of IL-DLLME approach was investigated. COSMO-RS results suggested that, quaternary ammonium and choline cations form effective IL combinations with [OH¯], [F¯], and [SO42¯] anions due to hydrogen bonding. In view of these results, one of the screened ILs, tetramethylammonium hydroxide [TMAm][OH] was chosen as the extractant in IL-DLLME process and acetonitrile was adopted as the dispersive solvent. The highest SA removal efficiency of 97.8% was achieved using 25 μL of IL [TMAm][OH] as a carrier and 500 μL of acetonitrile as dispersive solvent. The highest amount of SA was extracted with a stir time of 20 min at 300 rpm, followed by centrifugation for 5 min at 4500 rpm. Overall, the findings showed that IL-DLLME is efficient in extracting succinic acid from aqueous environments while adhering to the first-order kinetics.

DOI： 10.1080/09593330.2023.2234669

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Publisher：Waste and Biomass Valorization  

Purpose: This work evaluated the profiles of Industrial agar seaweed waste biomass (ISWB) and pretreated ISWB by using deep eutectic solvent (DESs) and NaOH. The profiles of nanocellulose obtained from pretreated ISWB (with various types of hydrogen bond donors of choline chloride (ChCl)-based hydrated DES) were also evaluated. Methods: ISWB underwent pre-treatment with either 100% wt. DES (1:1 molar ratio of ethylene glycol: citric acid) or 10% wt. NaOH at 80 °C to 90 °C. Subsequent treatment involved 10% wt. DES or ChCl-based hydrated DES with various HBDs (oxalic acid, citric acid, and urea) in a 1:2 molar ratio to produce nanocellulose. Results: Cellulose nanofibers isolated by the CE-DES approach exhibited a substantially higher yield compared with those obtained via the CE-NaOH method. CE-DES method induced swelling of ISWB and facilitate production of cellulose nanofibers. SEM images of samples indicates the presence of fibrous nanostructures across the majority of the specimens. Fourier-transform infrared (FTIR) spectroscopy demonstrated uniformity among all samples; they exhibited a consistent fingerprint pattern. X-ray diffraction (XRD) spectra indicated the presence of cellulose Type I in cellulose nanofibers produced by CE–DES, but not definitively in nanocellulose produced by the CE–NaOH method. Conclusion: Cellulose nanofibers can be isolated from ISWB by using various DES and exhibits substantial characteristics of cellulose nanofibers from different ISWB pretreatment protocols. Graphical Abstract: (Figure presented.)

DOI： 10.1007/s12649-024-02499-z

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Language：English   Publisher：Molecules  

Herein, we report a transdermal patch prepared using an ionic liquid-based solid in oil (IL-S/O) nanodispersion and a pressure-sensitive adhesive (PSA) to deliver the macromolecular antigenic protein, ovalbumin (OVA). The IL-S/O nanodispersion and a PSA were first mixed at an equal weight ratio, then coated onto a release liner, and covered with a support film. To evaluate the effect of the PSA, three types of PSAs, DURO-TAK 87-4098, DURO-TAK 87-4287, and DURO-TAK 87-235A, were used to obtain the corresponding IL-S/O patches SP-4098, SP-4287, and SP-235A, respectively. The prepared IL-S/O patches were characterized for surface morphology, viscoelasticity, and moisture content. In vitro skin penetration and in vivo immunization studies of the IL-S/O patches were performed using Yucatan micropig skin and the C57BL/6NJc1 mice model, respectively. The SP-4098 and SP-4287 delivered 5.49-fold and 5.47-fold higher amounts of drug compared with the aqueous formulation. Although both patches delivered a similar amount of drug, SP-4287 was not detached fully from the release liner after 30 days, indicating low stability. Mice immunized with the OVA-containing SP-4098 produced a 10-fold increase in anti-OVA IgG compared with those treated with an aqueous formulation. These findings suggested that the IL-S/O patch may be a good platform for the transdermal delivery of antigen molecules.

DOI： 10.3390/molecules29132995

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.jbiosc.2024.04.001

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Language：English   Publisher：(公社)日本生物工学会  

Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acssusresmgt.4c00100

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Publisher：ASEAN Journal of Chemical Engineering  

Ulva lactuca is a green seaweed commonly called sea lettuce and contains sulphated polysaccharides that have biological activity. Despite its lack of ecological sustainability, strong acids (HCl) and strong bases (NaOH) are widely used as solvents in the conventional extraction process for ulvan. Deep eutectic solvent (DES) is an alternative to ulvan extraction solvent, which is more environmentally friendly and has low toxicity. This study aims to assess the efficacy of peracetic acid (PAA) pretreatment and post-treatment in enhancing the quality of extracted ulvan using a DES-based solvent in the extraction process. Ulvan extraction using DES with a temperature of 85-95°C for 1 hour and adding 2% PAA pretreatment, 0.1%, 0.5%, and 2% PAA post-treatment were conducted. PAA pre-and post-treatment was carried out with a 1:10 (w/v) ratio at room temperature for 30 minutes. The analysis included moisture content, yield, functional groups, sulphate content, and color. The test results revealed that ulvan treated with 2% PAA pretreatment had the highest moisture content and sulphate content, at 18.71% and 33.39%, respectively, while ulvan treated with 0.1% PAA post-treatment had the highest yield, at 41.96%. Adding peracetic acid concentration can increase the color quality of the ulvan. PAA pre-and post-treatment had a significant effect on all ulvan quality parameters.

DOI： 10.22146/ajche.12272

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DOI： 10.1021/acssuschemeng.4c01799

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DOI： 10.1039/d3cc06130b

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DOI： 10.3390/ijms25073567

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DOI： 10.1101/2024.03.04.583322

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Language：English   Publisher：Communications Chemistry  

Assessing the formation of a deep eutectic solvent (DES) necessitates a solid-liquid equilibrium phase diagram. Yet, many studies focusing on DES applications do not include this diagram because of challenges in measurement, leading to misidentified eutectic points. The present study provides a practical approach for estimating the phase diagram of any binary mixture from the structural information, utilizing machine learning and quantum chemical techniques. The selected machine learning model provides reasonably high accuracy in predicting melting point (R2 = 0.84; RMSE = 40.53 K) and fusion enthalpy (R2 = 0.84; RMSE = 4.96 kJ mol−1) of pure compounds upon evaluation by test data. By pinpointing the eutectic point coordinates within an extensive chemical space, we highlighted the impact of the mole fractions and melting properties on the eutectic temperatures. Molecular dynamics simulations of selected mixtures at the eutectic points emphasized the pivotal role of hydrogen bonds in dictating mixture behavior.

DOI： 10.1038/s42004-024-01116-3

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DOI： 10.1021/acs.bioconjchem.3c00544

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DOI： 10.1021/acsbiomaterials.3c01386

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Language：English   Publisher：Japan Association of Solvent Extraction  

<p>We synthesized low-toxicity L-leucine propyl ester linoleate and L-leucine propyl ester oleate pseudo-protic ionic liquids (ILs) for benign extraction of Ni(II), Co(II), and Mn(II). The extraction ability order for both ILs was Ni(II) > Co(II) > Mn(II). In addition, we developed a machine learning model with an eXtreme Gradient Boosting regressor algorithm to evaluate and predict the ecotoxicity level of the ILs. An evaluation of the proposed regression model by cross-validation indicates that the model is reliable, with an R² value of 0.71. The prediction results indicate that the newly synthesized ILs are much less toxic than a commercially available IL (methyltrioctylammonium chloride) that is often used for metal extraction. </p>

DOI： 10.15261/serdj.31.31

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Publisher：Journal of Chemical Engineering of Japan  

This study explored the potential for an environmentally friendly method for refining difficult-to-solubilise noble metals (notably platinum). Conventional noble-metal refining processes rely on the use of strong inorganic acids and oxidants, which cause significant environmental impact. To overcome these challenges, we propose a non-aqueous direct leaching process using an ionic liquid, an organic acid, and a chlorinating agent. Our findings indicate that trihexyl(tetradecyl)phosphonium chloride (P66614Cl) in combination with methanesulfonic acid and trichloroisocyanuric acid effectively solubilises metallic platinum. We investigated the leaching mechanism using ultraviolet–visible spectroscopy and confirmed that Pt(0) was oxidised to Pt(IV) to form PtCl62-Recovery of Pt from Pt-loaded P66614Cl was achieved by stripping with ammonium nitrate solution. . This work advances the development of sustainable refining methods for noble metals.

DOI： 10.1080/00219592.2023.2228363

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Language：English   Publisher：Chemosphere  

Chemical dispersants are extensively used for marine oil spill remediation. However, the increased toxicity and low biodegradability of these dispersants restrict their employment in the marine environment. Hence, in this work, we have developed an eco-friendly formulation composed of an ionic liquid,1-butyl-3-methylimidazolium lauroyl sarcosinate [BMIM][Lausar] and sorbitan monooleate (Span) 80. Micellar and interfacial parameters, dispersion effectiveness, as well as the toxicity and biodegradability of the developed formulation were investigated. Micellar properties confirmed a high degree of synergism among the surfactant molecules and the formation of stable micelle. The dispersion effectiveness, at dispersant-to-oil ratio (DOR) of 1:25 (v/v), against three crude oils (Arab, Ratawi, and Doba) was assessed. We achieved a dispersion effectiveness of 68.49%, 74.05%, and 83.43% for Ratawi, Doba, and Arab crude oil, respectively, using a 70:30 (w/w) ratio of Span 80 to [BMIM][Lausar]. Furthermore, the results obtained from optical microscopy and particle size analysis (PSA) indicated that the oil droplet size decreased with higher DOR. Additionally, acute toxicity experiments were conducted on zebrafish (Danio rerio) using the developed formulation, confirming its non-toxic behavior, with LC50 values of 800 mg/L after 96 h. The formulation also exhibited high biodegradability, with only 25.01% of the original quantity remaining after 28 days. Hence, these results suggest that the new formulation has the potential to be a highly effective and environmentally friendly dispersant for oil spill remediation.

DOI： 10.1016/j.chemosphere.2023.140412

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Publisher：Arabian Journal for Science and Engineering  

In this age of cutting-edge technology, electronic equipment consumption, such as mobile phones, has increased tremendously. This was followed by a staggering increase in electronic waste (e-waste). However, it has been known that e-wastes contain higher amounts of precious metals than pristine sources, such as Au, which is valuable as an alternative precious metal source. Due to its various advantages, adsorption has emerged as one of the most common metal removal or recovery methods. A crucial aspect of adsorption is developing a cost-effective adsorbent for selective recovery of Au from the e-wastes. Thus, functionalized biomass-based adsorbent was developed to recover precious metals from e-waste. Functionalized activated carbon (ACIL900) has an appealing high adsorption capacity (116.2 mg g−1) performance and follows the chemisorption route, which fits with the monolayer model. The presence of IL boosts the adsorption efficiency due to its compatible interaction with the metal complexes. Remarkably, ACIL900 could quantitatively adsorb precious metals and several base metals from mobile phone leachate. The selective recovery of Au from the adsorbent was performed by sequential desorption using various solutions. Finally, Au was successfully recovered from the desorption solution using an electrochemical reduction process. ACIL900 was also found to maintain its performance for three adsorption–desorption cycles. This work reported the full recovery of Au from e-waste to its final pure product through the combination of adsorption, sequential desorption, and electrochemical reduction.

DOI： 10.1007/s13369-023-08327-1

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Publisher：Arabian Journal for Science and Engineering  

The article "Functionalization of Biomass-derived Activated Carbon and Electrochemical Reduction for the Recovery of Gold from Mobile Phone Leachate", written by Mochamad Lutfi Firmansyah, Ilma Amalina, Intan Nurul Rizki, Asmaul Mashad Alfaza,Prastika Krisma Jiwanti, Aishah Abdul Jalil, Masahiro Goto, was originally published electronically on the publisher’s internet portal on 20 October 2023 without open access. With the author(s)’ decision to opt for Open Choice, the copyright of the article changed on 9th October 2023 to © The Author(s) 2023 and the article is forthwith distributed under a Creative Commons Attribution 4.0 Interna?tional License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit.

DOI： 10.1007/s13369-023-08499-w

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Language：English   Publisher：(公社)日本生物工学会  

ペルオキシダーゼ触媒によるクロスリンク形成を介して生理的な条件下でゲル化を受けるアルブミン派生物を合成した。アルブミンをカルボジイミドを用いてフェノール性水酸基(Alb-Ph-OH)で修飾し、置換度がゲル化に及ぼす影響を解析した。Alb-Ph-OHヒドロゲルの多様な特性、すなわち、ゲル化時間、膨張率、孔径、貯蔵弾性率、および酵素的な分解性は置換度とポリマー濃度の調整により容易に調節可能であった。Alb-Ph-OHヒドロゲル中にカプセル化された細胞の生存率は高かった。

Language：Others   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.jbiosc.2023.09.007

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DOI： 10.1101/2023.10.09.561484

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DOI： 10.1002/tcr.202380802

Language：Japanese   Publisher：THE JAPAN SOCIETY OF DRUG DELIVERY SYSTEM  

The use of ionic liquids as drug delivery systems has received significant attention in recent years, especially due to their ability to enhance transdermal delivery. This function is useful not only for small molecule drugs but also for biopharmaceuticals like peptides and proteins, making it a promising option for developing non-invasive transdermal drug delivery systems. However, it is crucial to ensure the safety of ionic liquids for use as drugs. To address this, we introduce ionic liquids formed from safe materials such as choline, amino acids, fatty acids, and lipids. The use of biocompatible ionic liquids has enabled the development of mid-molecular drugs or transdermal vaccines that exhibit sustained-release properties of DDS. Moreover, there are great expectations for the use of ionic liquids in new modalities such as nucleic acid medicines.

DOI： 10.2745/dds.38.220

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CiNii Research

Language：English   Publishing type：Research paper (scientific journal)  

This study investigated the localization of artificial peptide supramolecular fibers in liquid-liquid phase separation (LLPS). Hierarchical organization led to the localization of supramolecules in LLPS droplets. Moreover, proteins were recruited into confined droplets by the physical adsorption of proteins on the supramolecules, enabling an enhanced cascade reaction.

DOI： 10.1039/D2CC05910J

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Language：Japanese   Publisher：THE MEMBRANE SOCIETY OF JAPAN  

Transdermal drug delivery is receiving a growing concern to alternate conventional drug administration techniques such as oral administration or needle–stick based administration methods. In this review article, we proposed a patch system based on a solid–in–oil nanodispersion technique as a simple and efficient delivery method of drugs, especially protein and peptide vaccines, through the skin. The skin is an attractive route for vaccination because there are many immune cells. We have developed the solid–in–oil nanodisperison technique to deliver pharmaceutical bioactives efficiently through the skin. Solid–in–oil nanodispersions are nanosized drug carriers designed to overcome the skin barrier. Drug administration using a patch is user–friendly and can improve patient compliance. Protein and peptide antigen drugs were efficiently delivered across the intact skin using the solid–in–oil nanodispersions. The technique is potent transcutaneous immunization method without needles.

DOI： 10.5360/membrane.48.25

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Language：English   Publishing type：Research paper (scientific journal)  

Cytoplasm contains high concentrations of biomacromolecules. Protein behavior under such crowded conditions is reportedly different from that in an aqueous buffer solution, mainly owing to the effect of volume exclusion caused by the presence of macromolecules. Using a crosslinking reaction catalyzed by microbial transglutaminase (MTG) as a model, we herein systematically determined how the substrate size affects enzymatic activity in both dilute and crowded solutions of dextran. We first observed a threefold reduction in MTG-mediated crosslinking of a pair of small peptide substrates in 15 wt% dextran solution. In contrast, when proteinaceous substrates were involved, the crosslinking rates in 15 wt% dextran solutions accelerated markedly to levels comparable with the level in the absence of dextran. Our results provide new insights into the action of enzymes with regard to macromolecular substrates under crowded conditions, of which the potential utility was demonstrated by the formation of highly crosslinked protein polymers.

DOI： 10.1039/D2OB01549H

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Language：English   Publisher：Pharmaceutical Research  

Ionic liquids (ILs) have attracted growing interest as designer solvents/materials for exploring unrealized functions in many areas of research including drug formulations and delivery owing to their inherent tunable physicochemical and biological properties. The use of ILs in the pharmaceutical industry can address challenges related to the use of conventional organic solvent-based chemical permeation enhancers. Their tunability in forming ion pairs with a diverse range of ions enables the task-specific optimization of ILs at the molecular level. In particular, ILs comprising second- and third-generation cations and anions have been extensively used to design biocompatible drug delivery systems to address the challenges related to conventional topical and transdermal drug delivery, including limited permeability, high cytotoxicity, and skin irritation. This review highlights the progress in IL-related research with particular emphasis on the very recent conceptual developments in transdermal drug delivery. Technological advancement and approaches for the formation of IL-based topical and transdermal delivery systems, as well as their promising application in drug delivery, are also discussed.

DOI： 10.1007/s11095-022-03322-x

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Language：Others   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Fungal infections affect more than one billion people worldwide and cause more than one million deaths per year. Amphotericin B (AmB), a polyene antifungal drug, has been used as the gold standard for many years because of its broad antifungal spectrum, high activity, and low tendency of drug resistance. However, the side effects of AmB, such as nephrotoxicity and hepatotoxicity, have hampered its widespread use, leading to the development of a liposome-type AmB formulation, AmBisome. Herein, we report a simple but highly effective strategy to enhance the antifungal activity of AmBisome with a lipid-modified protein. The chitin-binding domain (LysM) of the antifungal chitinase, Pteris ryukyuensis chitinase A (PrChiA), a small 5.3 kDa protein that binds to fungal cell wall chitin, was engineered to have a glutamine-containing peptide tag at the C-terminus for the microbial transglutaminase (MTG)-catalyzed crosslinking reaction (LysM-Q). LysM-Q was site-specifically modified with a lysine-containing lipid peptide substrate of MTG with a palmitoyl moiety (Pal-K). The resulting palmitoylated LysM (LysM-Pal) exhibited negligible cytotoxicity to mammalian cells and can be easily anchored to yield LysM-presenting AmBisome (LysM-AmBisome). LysM-AmBisome exhibited a dramatic enhancement of antifungal activity toward Trichoderma viride and Cryptococcus neoformans, demonstrating the marked impact of displaying a cell-wall binder protein on the targeting ability of antifungal liposomal formulations. Our simple strategy with enzymatic protein lipidation provides a potent approach to upgrade other types of lipid-based drug formulations.

DOI： 10.1021/acs.molpharmaceut.2c00388

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DOI： 10.1021/acsomega.2c03425

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DOI： 10.1016/j.jbiosc.2022.06.005

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Language：English   Publisher：(公社)日本生物工学会  

市販のアンフォテリシンB(AMB)製剤と表面電荷が異なるリポソームを組合せてハイブリッドリポソーム製剤を調製し、抗真菌活性の重要な要因を探索した。AMB含有リポソーム製剤(AMB-LF)の粒子サイズ分布とゼータ電位を含む特性評価では、陰イオン性と中性のAMB-LFはAMBを安定的にカプセル化できた。アニオン性または中性AMB-LFと未修飾LysMの組合せではAMBのMICが低下した。中性AMB-LFとPteris ryukyuensisキチナーゼ由来の人工パルミトイル化キチン結合ドメインの組合せではMICは更に減少し、中性AMB-LF単独と比較して最大15倍になった。以上より、脂質修飾性蛋白質結合剤と組合せたAMBの脂質基盤リポソーム製剤の真菌感染に対する有用であると考えられた。

Language：Others   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Protein palmitoylation, a post-translational modification, is universally observed in eukaryotic cells. The localization of palmitoylated proteins to highly dynamic, sphingolipid- and cholesterol-rich microdomains (called lipid rafts) on the plasma membrane has been shown to play an important role in signal transduction in cells. However, this complex biological system is not yet completely understood. Here, we used a combined approach where an artificial lipidated protein was applied to biomimetic model membranes and plasma membranes in cells to illuminate chemical and physiological properties of the rafts. Using cell-sized giant unilamellar vesicles, we demonstrated the selective partitioning of enhanced green fluorescent protein modified with a C-terminal palmitoyl moiety (EGFP-Pal) into the liquid-ordered phase consisting of saturated phospholipids and cholesterol. Using Jurkat T cells treated with an immunostimulant (concanavalin A), we observed the vesicular transport of EGFP-Pal. Further cellular studies with the treatment of methyl beta-cyclodextrin revealed the cholesterol-dependent internalization of EGFP-Pal, which can be explained by a raft-dependent, caveolae-mediated endocytic pathway. The present synthetic approach using artificial and natural membrane systems can be further extended to explore the potential utility of artificially lipidated proteins at biological and artificial interfaces.

DOI： 10.1021/acs.langmuir.2c01205

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Language：English   Publishing type：Research paper (scientific journal)  

Single-walled carbon nanotubes (SWCNTs) emit photoluminescence (PL) in the near-infrared (NIR) region (>900 nm). To enhance their PL properties, defect doping via local chemical functionalization has been developed. The locally functionalized SWCNTs (lf-SWCNTs) emit red-shifted and bright E11* PL originating from the excitons localized at the defect-doped sites. Here, we observe the E11* PL energy shifts induced by protein adsorption via the avidin-biotin interactions at the doped sites of lf-SWCNTs. We establish that the difference in the structures of the avidin derivatives notably influences the energy shifts. First, lf-SWCNT-tethering biotin groups (lf-SWCNTs-b) are synthesized based on diazonium chemistry, followed by post-modification. The responsiveness of the lf-SWCNTs-b to different microenvironments is investigated, and a correlation between the E11* PL energy shift and the induction-polarity parameters of surrounding solvents is established. The adsorption of neutravidin onto the lf-SWCNTs-b induces an increase in the induction-polarity parameters around the biotin-doped sites, resulting in the red-shift of the E11* PL peak. The E11* PL shift behaviors of the lf-SWCNTs-b change noticeably when avidin and streptavidin are introduced compared to the case with neutravidin. This is due to the different microenvironments formed at the biotin-doped sites, attributed to the difference in the structural features of the introduced avidin derivatives. Moreover, we successfully enhance the detection signals of lf-SWCNTs-b (>three fold) for streptavidin detection using a fabricated film device. Therefore, lf-SWCNTs exhibit significant promise for application in advanced protein detection/recognition devices based on NIR PL.

DOI： 10.1039/D2NR01440H

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Language：Others   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

DOI： 10.1021/acsomega.2c00752

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Language：Japanese   Publisher：The Society of Chemical Engineers, Japan  

<p>Two different ionic liquids, 1-alkyl-3-methylimidazolium hexafluorophosphate and 1-alkyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, were used as a transport carrier of rhodium (III) extraction. Extraction of rhodium from hydrochloric acid media was conducted by liquid surfactant membranes (LSMs) containing the ionic liquid carrier. The extraction of rhodium was accelerated by the addition of tin (II) to the aqueous feed solution. The effects of various operational parameters on the extraction behavior of rhodium and tin were investigated. The extraction rates of both metals were greatly influenced by the ionic liquid species, the surfactant concentration, and the concentration of stripping reagent. The alkyl-chain length and the anionic part in the ionic liquids were proved to be important to get a high extraction yield of rhodium. In addition, it was found that the concentration of 2-amino-2-hydroxymethyl-1,3-propanediol used as the stripping reagent played a crucial role on the selective extraction of rhodium from a large amount of tin, and there was an optimum concentration to obtain the best performance of LSMs. Under the optimum operating conditions for the present system, rapid and quantitative extraction of rhodium was achieved.</p>

DOI： 10.1252/kakoronbunshu.48.81

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Language：English  

DOI： 10.1200/PO.21.00535

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

Combinations of antifungal drugs can have synergistic antifungal activity, achieving high therapeutic efficacy while minimizing the side effects. Amphotericin B (AMB) has been used as a standard antifungal drug for fungal infections; however, because of its high toxicity, new strategies to minimize the required dose are desirable. Chitinases have recently received attention as alternative safe antifungal agents. Herein, we report the combination of palmitoylated chitinase domains with AMB to enhance the antifungal activity. The chitin-binding domain (LysM) from Pteris ryukyuensis chitinase was site-specifically palmitoylated by conjugation reaction catalyzed by microbial transglutaminase. The palmitoylated LysM (LysM-Pal) exhibited strong antifungal activity against Trichoderma viride, inhibiting the growth completely at a concentration of 2 μM. This antifungal effect of LysM-Pal was mainly due to the effect of anchoring of palmitic acid motif to the plasma membrane of fungi. A combination of AMB with LysM-Pal resulted in synergistic enhancement of the antifungal activity. Intriguingly, LysM-Pal exhibited higher level of antifungal activity enhancement than palmitoylated catalytic domain (CatD) and fusion of LysM and CatD. Addition of 0.5 μM LysM-Pal to AMB reduced the minimal inhibition concentration of AMB to 0.31 μM (2.5 μM without LysM-Pal). The possible mechanism of the synergistic effect of AMB and LysM-Pal is destabilization of the plasma membrane by anchoring of palmitic acid and ergosterol extraction by AMB and destabilization of the chitin layer by LysM binding. The combination of LysM-Pal with AMB can drastically reduce the dose of AMB and may be a useful strategy to treat fungal infections.

DOI： 10.1021/acsinfecdis.2c00052

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/D2RA00064D

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.15261/serdj.29.79

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.hydromet.2022.105826

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier {BV}  

DOI： 10.1016/j.molliq.2021.118280

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

Self-sorting and co-assembly of aqueous supramolecular fibres were formed using peptide amphiphiles having immiscible hydrophobic tails.

DOI： 10.1039/d1cc05560g

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Language：Others   Publishing type：Research paper (scientific journal)   Publisher：Elsevier {BV}  

DOI： 10.1016/j.molliq.2021.118208

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Language：Japanese   Publisher：Japan Oil Chemists' Society  

<p>Biomolecules such as proteins or nucleic acids have been utilized as biopharmaceutical drugs, which produce various pharmacological activities. The development of a novel transdermal delivery system of biopharmaceuticals attracts much attention because it provides the easy and safe administration method compared to injection. The Solid-in-Oil (S/O) nanodispersion technique consists of the oil-based dispersion, in which the biopharmaceuticals are coated with hydrophobic surfactant molecules and dispersed in the oil phase as nanometer-sized particles. Insulin, a model pharmaceutical drug, enables to be dispersed in isopropyl myristate (IPM), that is known to be an effective skin penetration enhancer, by forming the S/O nanodispersion. The permeability of insulin into the skin was drastically enhanced. Further, the transdermal vaccination has been studied as one of the most important applications of the S/O nanodispersion. It was proved that the S/O nanodispersion containig a model antigen produced the antigen-specific antibodies and induced the cytotoxic cellular immunity in mouse. These results suggested that the S/O nanodispersion technique is useful for delivering biopharmaceuticals into the skin, and expected to become available in clinical.</p>

DOI： 10.5650/oleoscience.22.121

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Language：Others   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.cocis.2021.101515

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DOI： 10.1021/acsami.1c16659

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DOI： 10.1016/j.ijpharm.2021.121129

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DOI： 10.1021/acsami.1c11533

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.desal.2021.115073

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.bioconjchem.1c00235

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DOI： 10.1021/acsabm.1c00563

Language：Others   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.molpharmaceut.1c00324

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.memsci.2021.119296

Language：Others   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.bioconjchem.1c00027

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.2116/analsci.20SCR07

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/d1ra00489a

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.3390/ijms22073459

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DOI： 10.1021/acssuschemeng.0c07606

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DOI： 10.1038/s41598-020-63362-4

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DOI： 10.1016/j.ejps.2020.105521

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DOI： 10.1016/j.molliq.2020.114424

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DOI： 10.1021/acsabm.0c00940

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DOI： 10.1039/d0cc04491a

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DOI： 10.1016/j.jbiosc.2020.05.010

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DOI： 10.1021/acs.molpharmaceut.0c00598

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DOI： https://doi.org/10.1021/acsabm.0c00940

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Ionic liquid (IL)-based drug delivery systems have attracted considerable interest owing to their intrinsic tunability and ability to transport small or large molecules through the skin. However, the development of "green"ILs remains challenging. Herein, eight potentially "green"fatty acid-based amino acid ILs (FAAAE-ILs) were synthesized, and their potency in transdermal drug delivery was investigated using ibuprofen and a peptide drug. The synthesized ILs were characterized to evaluate their physicochemical, thermal, and biological (cytotoxicity) properties. The in vitro skin permeability of the synthesized FAAAE-ILs was evaluated through pig skin. All of the FAAAE-ILs are liquid at room temperature and freely miscible with pharmaceuticals-permitted solvents/agents (e.g., isopropyl myristate (IPM), Span-20, and DMSO). In vitro cytotoxicity study showed that the cell viability of all FAAAE-ILs (10% in IPM) was at least 10 times lower than that for a conventional chemical permeation enhancer (CPE), sodium lauryl sulfate. FAAAE-ILs facilitated excellent ibuprofen solubility through multiple hydrogen bonding interactions between the drug and the ILs. An in vitro permeation study showed that the FAAAE-ILs were more effective in enhancing the permeability of drug molecules than the conventional CPE transcutol. The linoleate-based ILs showed a higher degree of permeation than the oleate-based ILs. Among the linoleate-based ILs and ibuprofen formulations (drug in 10% IL in IPM), the l-proline ethyl ester linoleate ([l-ProEt][Lin])-based formulation exhibited best results, followed by β-alanine ethyl ester linoleate, d-proline ethyl ester linoleate, and l-leucine ethyl ester linoleate after 48 h. Interestingly, the same FAAAE-IL ([l-ProEt][Lin])-containing formulation showed significant enhancement of peptide penetration across pig skin compared with CPE-containing formulations (10% in IPM). The results demonstrate that the FAAAE-IL is a promising green alternative to conventional CPEs for the transdermal delivery of small and large therapeutic molecules.

DOI： 10.1021/acssuschemeng.0c03419

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1252/jcej.20we030

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DOI： 10.3390/pharmaceutics12090814

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DOI： 10.1021/acssuschemeng.0c03205

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DOI： 10.1038/s41428-020-0344-7

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DOI： 10.1016/j.molliq.2020.113122

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DOI： 10.1016/j.jbiosc.2020.05.010

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DOI： 10.1016/j.ab.2020.113700

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DOI： 10.3390/cosmetics7030052

Language：English   Publishing type：Research paper (scientific journal)  

Other Link： https://doi.org/10.1039/C9TA13077B

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acsomega.0c00867

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1038/s41598-020-63362-4

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DOI： 10.1021/acssuschemeng.9b07773

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DOI： 10.1021/acsomega.9b04163

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DOI： 10.1248/bpb.b19-00642

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DOI： 10.1088/1755-1315/415/1/012019

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.molpharmaceut.9b01104

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DOI： 10.1016/j.bej.2019.107426

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DOI： 10.1016/j.molliq.2019.112166

Language：English   Publishing type：Research paper (scientific journal)  

An allergy to cow's milk proteins is the most common food allergy in infants and toddlers. Conventional oral immunotherapy for cow's milk allergies requires hospital admission due to the risk of severe allergic reactions, including anaphylaxis. Therefore, a simpler and safer immunotherapeutic method is desirable. We examined transcutaneous immunotherapy with a solid-in-oil (S/O) system. In the S/O system, nano-sized particles of proteins are dispersed in an oil-vehicle with the assistance of nonionic surfactants. In the present study, the S/O system enhanced the skin permeation of the allergen molecule β-lactoglobulin (BLG), as compared with a control PBS solution. The patches containing BLG in the S/O nanodispersion skewed the immune response in the allergy model mice toward T helper type 1 immunity, indicating the amelioration of allergic symptoms. This effect was more pronounced when the immunomodulator resiquimod (R-848) was included in the S/O system.

DOI： 10.3390/pharmaceutics12030205

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acsomega.9b02540