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。

記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：ChemBioEng Reviews  

Despite advances in cancer treatment, many types of cancer still have high mortality rates, and the existing therapies can cause considerable side effects. Therefore, discovering new therapies, especially ones with fewer side effects, is desirable to improve the outcomes for cancer patients. Ionic liquids (ILs) have emerged as potential candidates for cancer treatment because of their particular physicochemical properties, which can be tailored for specific applications. In recent years, interest in exploring the potential of ILs in cancer treatment has been growing, and several studies have demonstrated the effectiveness of ILs in inhibiting cancer-cell growth. This review provides insight into the anticancer potential of ILs, exploring the diverse applications and the underlying mechanisms behind the cytotoxicity toward cancer cells of ILs. Understanding the mechanisms behind the cytotoxicity of ILs can aid in the design and optimization of IL-based cancer therapies. By focusing on specific pathways and targets, IL-based cancer therapies may be developed that offer new possibilities for treating this devastating disease.

DOI： 10.1002/cben.202300051

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Food Chemistry  

Flavonoids have diverse beneficial roles that potentiate their application as nutraceutical agents in nutritional supplements and as natural antimicrobial agents in food preservation. To address poor solubility and bioactivity issues, we developed water-soluble micellar formulations loaded with single and multiple flavonoids using the biocompatible surface-active ionic liquid choline oleate. The food preservation performance was investigated using luteolin, naringenin, and quercetin as model bioactive compounds. The micellar formulations formed spherical micelles with particle sizes of <150 nm and exhibited high aqueous solubility (>5.15 mg/mL). Co-delivery of multiple flavonoids (luteolin, naringenin, and quercetin in LNQ-MF) resulted in 84.85% antioxidant activity at 100 μg/mL. The effects on Staphylococcus aureus and Salmonella enterica were synergistic with fractional inhibitory concentration indices of 0.87 and 0.71, respectively. LNQ-MF hindered the growth of S. aureus in milk (0.83–0.89 log scale) compared to the control. Co-delivered encapsulated flavonoids are a promising alternative to chemical preservatives.

DOI： 10.1016/j.foodchem.2023.136911

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記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.21203/rs.3.rs-3338523/v1

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Chemical Record  

Ionic liquids (ILs) have been extensively used in drug formulation and delivery as designer solvents and other components because of their inherent tunability and useful physicochemical and biopharmaceutical properties. ILs can be used to manage some of the operational and functional challenges of drug delivery, including drug solubility, permeability, formulation instability, and in vivo systemic toxicity, that are associated with conventional organic solvents/agents. Furthermore, ILs have been recognized as potential solvents to address the polymorphism, limited solubility, poor permeability, instability, and low bioavailability of crystalline drugs. In this account, we discuss the technological progress and strategies toward designing biocompatible ILs and explore potential biomedical applications, namely the solubilization of small and macromolecular drugs, the creation of active pharmaceutical ingredients, and the delivery of pharmaceuticals.

DOI： 10.1002/tcr.202300026

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Applied Materials and Interfaces  

Nucleic acid drugs, including antisense oligonucleotides (ASOs), have received considerable attention as novel therapeutics for the treatment of intractable diseases. Despite their potential benefits, ASOs are currently administered via injection, which can negatively impact patient quality of life because of the prevalence of severe injection site reactions. Non-invasive transdermal administration of ASOs is desirable but highly challenging owing to the strong barrier imposed by the stratum corneum, which only permits the penetration of small molecules under 500 Da. For ASOs to exert their antisense effect, they must traverse the negatively charged cell membrane and reach the cytoplasm. In this study, we used the solid-in-oil (S/O) dispersion technology to facilitate the skin permeation of ASOs by coating the drug with a hydrophobic surfactant molecule, specifically lipid-based ionic liquid (IL) surfactants with high biocompatibility and transdermal penetration-enhancing properties. To induce the antisense effect, it was important to achieve simultaneous transdermal delivery and intracellular entrapment of ASOs. In vitro investigations indicated that the newly prepared IL-S/O enhanced the transdermal penetration and intracellular delivery of ASOs, thus inhibiting mRNA translation of the target TGF-β. In addition, in vivo investigations of tumor-bearing mice suggested that the anti-tumor effect of the IL-S/O was similar to that of injection. This study demonstrates the potential of non-invasive transdermal delivery carriers based on biocompatible ILs, which can be applied to a variety of nucleic acid drugs.

DOI： 10.1021/acsami.3c03900

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：日本溶媒抽出学会  

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.

DOI： 10.15261/serdj.30.149

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Processes  

The current alternative of using aromatic-based wax soak solvents has been found to be hazardous and imposes a high cost on field expenditures. These solvents are widely used in the oil and gas industry to soften up wax before the pigging process. However, their impacts on the environment are quite concerning. Plus, they also impose hazardous exposure and are found to be damaging to both plastic and rubber hoses. To replace the current alternative with other hydrocarbon-based wax soak solvents, ionic liquids were found to have the capability to increase the solvent power capabilities and the efficiency of wax soak solvent in dissolving heavy crude oil. To optimise the application of hydrocarbon solvents and ionic liquid in wax dissolution, the affinity of ionic liquids in three solvents was studied. The solvents were condensate, ethyl acetate, and xylene. It was found that from four types of ionic liquids tested, only BMIMCL and HMIMBr were miscible in all three of the solvents used. Dissolution of hard deposited paraffin wax in condensate, ethyl acetate and xylene was conducted using the spectral analysis method, and it was found that the dissolution of paraffin wax was greatest in ethyl acetate. However, enchantment on wax dissolution was also observed for gas condensate and xylene. The wax soaking time was also optimised, in which the dissolution of wax was found to reach a saturation level when the wax had been soaked for over 90 min in the solvents, especially for gas condensate. Further study on the effect of ionic liquid introduced alongside condensate, ethyl acetate and xylene, aiming to enhance the solvent power, was also conducted using the spectral analysis method. The introduction of ionic liquids to all hydrocarbon-based wax soak solvents used in this project was proven to significantly increase the UV-VIS absorbance of the extracted solvents after paraffin wax had been soaked for 30 min.

DOI： 10.3390/pr11041112

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記述言語：その他  

DOI： 10.3390/molecules28072969

記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Molecules  

Ibuprofen (Ibf) is a biologically active drug (BADs) and an emerging contaminant of concern (CECs) in aqueous streams. Due to its adverse effects upon aquatic organisms and humans, the removal and recovery of Ibf are essential. Usually, conventional solvents are employed for the separation and recovery of ibuprofen. Due to environmental limitations, alternative green extracting agents need to be explored. Ionic liquids (ILs), emerging and greener alternatives, can also serve this purpose. It is essential to explore ILs that are effective for recovering ibuprofen, among millions of ILs. The conductor-like screening model for real solvents (COSMO-RS) is an efficient tool that can be used to screen ILs specifically for ibuprofen extraction. The main objective of this work was to identify the best IL for the extraction of ibuprofen. A total of 152 different cation?anion combinations consisting of eight aromatic and non-aromatic cations and nineteen anions were screened. The evaluation was based upon activity coefficients, capacity, and selectivity values. Furthermore, the effect of alkyl chain length was studied. The results suggest that quaternary ammonium (cation) and sulfate (anion) have better extraction ability for ibuprofen than the other combinations tested. An ionic liquid-based green emulsion liquid membrane (ILGELM) was developed using the selected ionic liquid as the extractant, sunflower oil as the diluent, Span 80 as the surfactant, and NaOH as the stripping agent. Experimental verification was carried out using the ILGELM. The experimental results indicated that the predicted COSMO-RS and the experimental results were in good agreement. The proposed IL-based GELM is highly effective for the removal and recovery of ibuprofen.

DOI： 10.3390/molecules28052345

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記述言語：日本語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Hydrometallurgy  

Solvent extraction of scandium(III) from an aqueous solution, which simulates a concentrated scandium solution generated from nickel/cobalt mixed-sulfide production process, was performed using a ternary mixed extractant system. Addition of tri-n-octylphosphine oxide and a long-chain alkyl carboxylic acid (Versatic 10) to an organophosphonic ester (PC-88A) drastically improved the separation factor of scandium over zirconium in comparison with that of a single extractant system. The optimum mixing ratio in the ternary extractant system was 10 mol% PC-88A, 60 mol% tri-n-octylphosphine oxide, and 30 mol% Versatic 10. The degree of scandium extraction was 90%, and the separation factors between scandium and other metals (i.e., Al, Fe, Ni, Cr, and Zr) were > 140 at pH 2 with the optimized ternary extractant system. The operating conditions for a countercurrent multistage extraction of scandium were investigated by McCabe?Thiele analysis. Ninety-nine percent recovery from 1800 mg dm?3 scandium was achieved by two- to three-stage countercurrent extraction at the flow ratio (A/O) = 1.01. The stripping efficiency of scandium reached >98% with 7 mol dm?3 H3PO4. Based on the results, a conceptual flowsheet for scandium recovery from waste solutions of laterite ore leachate is proposed.

DOI： 10.1016/j.hydromet.2023.106024

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Pharmaceutics  

The development of effective drug formulations and delivery systems for newly developed or marketed drug molecules remains a significant challenge. These drugs can exhibit polymorphic conversion, poor bioavailability, and systemic toxicity, and can be difficult to formulate with traditional organic solvents due to acute toxicity. Ionic liquids (ILs) are recognized as solvents that can improve the pharmacokinetic and pharmacodynamic properties of drugs. ILs can address the operational/functional challenges associated with traditional organic solvents. However, many ILs are non-biodegradable and inherently toxic, which is the most significant challenge in developing IL-based drug formulations and delivery systems. Biocompatible ILs comprising biocompatible cations and anions mainly derived from bio-renewable sources are considered a green alternative to both conventional ILs and organic/inorganic solvents. This review covers the technologies and strategies developed to design biocompatible ILs, focusing on the design of biocompatible IL-based drug formulations and delivery systems, and discusses the advantages of these ILs in pharmaceutical and biomedical applications. Furthermore, this review will provide guidance on transitioning to biocompatible ILs rather than commonly used toxic ILs and organic solvents in fields ranging from chemical synthesis to pharmaceutics.

DOI： 10.3390/pharmaceutics15041179

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記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.3390/molecules28072969

記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Journal of Pharmaceutical Sciences  

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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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Omega  

To reduce the exploitation of mine resources and decrease the harm to the environment caused by urban electronic wastes, the recovery of critical metals in secondary resources is crucial. In this study, we have successfully developed an eco-friendly process to integrate the leaching and separation of cobalt (Co) from a spent lithium-ion battery (LIB) cathode using an amino acid-based aqueous biphasic system (ABS). We, for the first time, demonstrated a simple method for leaching a LIB cathode using only amino acids. In addition, we have investigated the leaching mechanism using the typical cathode active material lithium cobalt oxide (LiCoO2). Then, the Co was selectively extracted by a biphasic system (amino acid?PPG400?H2O). This novel process has an excellent prospect in the field of spent-battery recycling because of its eco-friendly and process-simplified advantages.

DOI： 10.1021/acsomega.2c06654

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Applied Materials and Interfaces  

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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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Journal of Molecular Liquids  

Luteolin (LUT), an important flavonoid, shows excellent antioxidant and antimicrobial properties. However, its low solubility and stability in water, as well as challenges related to its formulation, have limited its use in food preservation. Here, we develop a highly water-soluble LUT-loaded micellar formulation (LUT-MF) using a solid-in-water nanodispersion technique involving emulsification and lyophilization processes. LUT solubilized in an organic phase comprising acetone, methanol, and cyclohexane (5:10:85 v/v) was emulsified with an aqueous solution of a surface-active ionic liquid, choline oleate ([Cho][Ole]), and the oil in water emulsion was lyophilized to remove the organic phase and water and obtain a solid LUT-[Cho][Ole] complex. LUT-[Cho][Ole] complex was dispersed again in water to prepare the LUT-MF formulation with good stability. Dynamic light scattering and transmission electron microscopy confirmed that the LUT-MF formed spherical micelles with a mean particle size of approximately 73 nm. LUT-MF showed excellent encapsulation efficiency (94.3%) and enhanced aqueous solubility. An in vitro release study in PBS containing 30% ethanol demonstrated 3.94 times higher release of LUT from LUT-MF than from LUT suspension after 24 h. The developed formulation showed better antioxidant activity than both free LUT and ascorbic acid. LUT-MF demonstrated higher antibacterial activity than sodium benzoate. Food preservation studies revealed that treating strawberries with LUT-MF effectively preserved color and prevented shriveling and decay over 8 days storage at 10 °C, compared with sodium benzoate treatment. The results suggest that LUT-MF is a potential natural preservative alternative to conventional toxic chemical preservatives used in the food industry.

DOI： 10.1016/j.molliq.2022.120151

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Biochemical Engineering Journal  

Selectivity is a crucial factor for gold recovery from discarded cell phones. This is because discarded cell phones contain a large variety of metals. The use of biomaterials as gold adsorbents is attracting much attention because it is in accordance with sustainability goals. Here, we reported selective adsorption of gold on silk fibroin and its application to gold recovery from the actual leachate of discarded cell phones in a chloride medium. The experimental maximum gold-adsorption capacity of silk fibroin was 5.800 mg/g. Based on a kinetic study, the gold-adsorption mechanism followed the pseudo-second-order model with a rate constant (k2) of 0.077 g mg−1min−1. The adsorption fitted well with the Langmuir model, suggesting a monolayer adsorption mechanism. Despite the small adsorption capacity, silk fibroin showed remarkable selectivity toward gold in synthetic and actual leachate containing Pt4+, Pd2+, Al3+, Cu2+, Ni2+, Zn2+, Pb2+, and Fe3+ metal ions in 0.5 mol/L HCl. The gold uptake from the actual leachate of discarded cell phones was approximately 95 %. The gold loaded on the silk fibroin was completely desorbed by 0.1 mol/L thiourea.

DOI： 10.1016/j.bej.2022.108690

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Sustainable Chemistry and Engineering  

Metals are key components of modern devices; however, available resources of these metals are limited. In this study, we used machine learning (ML) to curate ionic liquids (ILs) that are suitable for metal extraction. We proposed classification and regression models to unravel hidden patterns between IL structures and their specific properties, i.e., metal selectivity and eco-toxicity. Evaluations of ML models using cross-validation indicate that the models were reliable, as described by the accuracy score (0.82) and R2value (0.76). The models also revealed that the metal selectivity of ILs was determined by the cation and anion structures, and the eco-toxicity level was primarily affected by the cation structures. Guided by predictions from the trained models, we selected three ILs (out of the 150 IL structures we initially proposed) that have extraction selectivity toward platinum, lithium, and neodymium as well as low eco-toxicity. We then prepared the ILs in the laboratory and assessed their performance by standard solvent extraction. The experiments indicate that the recommended ILs from ML could selectively extract the targeted metals with high extraction efficiency (>80%), which demonstrates the feasibility of ML as a promising toolkit that can help accelerate innovations in metal extraction.

DOI： 10.1021/acssuschemeng.2c03480

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Applied Bio Materials  

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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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Green Chemistry  

Expansion of the global market for electric vehicles has brought about a significant increase in the demand for the critical metals necessary for lithium-ion battery cathodes. Conventional cathode recycling processes can be detrimentally impactful to the environment because of the high-temperature treatment needed, and the hazardous inorganic acids and organic solvents used. Here, we demonstrate a novel cathode recycling process that employs hydrophobic eutectic solvents (HESs), which have recently attracted interest as green solvents. Our proposed process operates at mild temperatures and uses a reusable HES as an alternative to the aforementioned hazardous acids and solvents. This process consists of two simple steps, starting with direct leaching of the cathode materials by HESs typically composed of synergistic metal ligands, such as a diketone and an alkyl phosphine oxide, after which the leached critical metal ions are then separated and recovered into an aqueous oxalic acid solution. Under the optimal conditions, more than 90% of lithium, cobalt, and other critical metals was leached out from the various cathode materials, aided by ascorbic acid as the natural reducing agent. Subsequently, the metals were quantitatively recovered from the HES into the stripping solution as the cobalt oxalate precipitation and lithium-rich solution. We have succeeded in developing a potentially environmentally harmonious recycling process suitable for the sustainable production of rechargeable batteries.

DOI： 10.1039/D1GC04846E

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Industrial and Engineering Chemistry Research  

The era of electric vehicles is rapidly approaching, and therefore, it is crucial to provide a sustainable technology for ensuring the circular economy of lithium-ion batteries. In this study, we report the development of a novel aqueous biphasic system (ABS) comprising fully biocompatible components, that is, hydrophilic ionic liquids, amino acids, and organic acids, for the selective recovery of Co(II) and Ni(II) from Mn(II), which are critical metals in spent lithium-ion batteries. Separation of Co(II), Ni(II), and Mn(II) from sulfate media was successfully carried out using the ABS in a quite straightforward manner without any hazardous reagents or organic solvents. In addition, the plausible mechanism of metal ion separation within the ABS was elucidated. The regenerated ionic liquid in the ABS exhibited remarkably stable performance during use in three consecutive experimental cycles.

DOI： 10.1021/acs.iecr.2c00295

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Biomaterials  

The biomaterial-based immunoengineering has become one of the most attractive research fields in the last decade. In the present study, a solid-in-oil-in-water (S/O/W) emulsion encapsulating antigen in the oil phase of an oil-in-water (O/W) emulsion was prepared as a novel vaccine carrier consisting of similar materials to the emulsion adjuvant of which the safety, immunogenicity and vaccination efficacy have been already confirmed in human. Direct observation by high-resolution confocal laser scanning microscopy and small angle X-ray scattering analysis showed that the antigens were dispersed inside of the oil phase of the S/O/W emulsion as solid-state particles. The S/O/W emulsion robustly produced antigen-specific antibodies and enhanced the antitumor effects in a therapeutic cancer vaccination compared with free antigens or the O/W emulsion in vivo. This result is in good agreement with the activation effect of antigen-specific cytotoxic T lymphocytes and antigen presentation by the S/O/W emulsion, indicating that the S/O/W emulsion consisting of already approved materials is a promising vaccine carrier to produce both humoral and cellular immunity.

DOI： 10.1016/j.biomaterials.2022.121385

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Journal of Molecular Liquids  

Ionic liquids (ILs) have gained great attention as potent solubilizing agents of poorly soluble bioactive compounds. The use of Luteolin (LUT) – a natural bioactive compound – is limited because of its poor aqueous solubility. To address this issue, this study reports potential ILs for effectively solubilizing LUT at ambient temperature. First, promising ILs were screened from a potential 180 ILs that were proposed by the combination of 20 standard amino acid ethyl esters cations and nine phenolic acids anions using the conductor-like screening model for real solvents (COSMO-RS); the activity coefficients of LUT at infinite dilution in ILs were used as the screening criteria. Four proline ethyl ester phenolate ILs (PEEP-ILs) composed of a biocompatible proline ethyl ester and bioactive phenolic acids (trans-ferulic, vanillic, p-coumaric, and 4-hydroxybenzoic acid) were selected and synthesized. The synthesized PEEP-ILs were characterized through 1H NMR, FT-IR, elemental analysis, TGA, and DSC. The experimental solubility of LUT in PEEP-ILs (60% IL in water) showed excellent solubility. Among the PEEP-ILs, proline ethyl ester ferulate (IL[ProEt][Fer]) exhibited the best LUT solubility, followed by ILs with p-coumarate (IL[ProEt][Cou]), vanillate (IL[ProEt][Van]), and 4-hydroxybenzoate (IL[ProEt][Ben]). 1H NMR assessment and COSMO-RS prediction confirmed that the ILs facilitated the solubilization of LUT through multiple hydrogen bonding, π − π, and cation − π interactions between the LUT and the ILs. The biocompatibility study revealed that PEEP-ILs were relatively harmless and low toxicity compared with conventional imidazolium, pyridinium, pyrrolidinium, piperidinium, and morpholinium-based ILs. The LUT dissolved in the newly-synthesized PEEP-ILs and demonstrated better organoleptic properties on red apple slices. These results indicate that PEEP-ILs can be potential green alternatives to conventional toxic solvents for dissolving poorly water-soluble bioactive natural preservatives.

DOI： 10.1016/j.molliq.2021.118103

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Separation and Purification Technology  

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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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Acta Biomaterialia  

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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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsami.1c11533

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.molpharmaceut.1c00324

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsabm.1c00563

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsami.1c03111

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.ijpharm.2021.120582

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.ejps.2020.105667

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://doi.org/10.1016/j.ejps.2020.105521

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://doi.org/10.1016/j.molliq.2020.114424

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://doi.org/10.1039/d0cc04491a

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.molpharmaceut.0c00598

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://doi.org/10.1016/j.molliq.2020.113603

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.3390/COSMETICS7030052

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://doi.org/10.3390/pharmaceutics12090814

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://dx.doi.org/10.1021/acssuschemeng.0c03419

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://doi.org/10.1021/acssuschemeng.0c03205

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.ijpharm.2020.119335

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://dx.doi.org/10.1021/acsomega.0c00867

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.3390/pharmaceutics12040392

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://doi.org/10.1021/acssuschemeng.9b07773

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.3390/pharmaceutics12030240

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.molliq.2019.112166

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.molpharmaceut.9b01104

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.bej.2019.107426

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsomega.9b02540

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.ijpharm.2019.118777

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.iecr.9b05183

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.3390/pharmaceutics11110563

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.ijpharm.2019.05.020

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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DOI： 10.1039/C8CC08163H

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DOI： 10.1252/jcej.18we175

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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記述言語：日本語   掲載種別：研究論文（学術雑誌）  

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記述言語：日本語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

Enzyme-Mediated Protein Refolding

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

Ionic liquid-assisted transdermal delivery of sparingly soluble drugs

記述言語：日本語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

Extraction Behavior of Indium with TOPO into Ionic Liquids

記述言語：英語   掲載種別：研究論文（学術雑誌）  

Development of a novel immobilization method for enzymes from hyperthermophiles

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

Formation of Reverse Micelles in a Room-Temperature Ionic Liquid

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/ac050782k

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1039/b505479f

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/la050364a

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1002/chem.200400691

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：日本語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DNA hybridization in reverse micelles and its application to mutation detection

DOI： 10.1039/b208755n

記述言語：英語   掲載種別：研究論文（学術雑誌）  

Novel surfactant for liquid surfactant membrane processes

DOI： 10.1252/jcej.20.157

出版者・発行元：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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出版者・発行元：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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出版者・発行元：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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記述言語：英語   出版者・発行元：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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PubMed

出版者・発行元：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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記述言語：英語   出版者・発行元：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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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Journal of Bioscience and Bioengineering  

Antibody drugs play a vital role in diagnostics and therapy. However, producing antibodies from mammalian cells is challenging owing to cellular heterogeneity, which can be addressed by applying droplet-based microfluidic platforms for high-throughput screening (HTS). Here, we designed an integrated system based on disulfide-bonded redox-responsive hydrogel beads (redox-HBs), which were prepared through enzymatic hydrogelation, to compartmentalize, screen, select, retrieve, and recover selected Chinese hamster ovary (CHO) cells secreting high levels of antibodies. Moreover, redox-HBs were functionalized with protein G as an antibody-binding module to capture antibodies secreted from encapsulated cells. As proof-of-concept, cells co-producing immunoglobulin G (IgG) as the antibody and green fluorescent protein (GFP) as the reporter molecule, denoted as CHO(IgG/GFP), were encapsulated into functionalized redox-HBs. Additionally, antibody-secreting cells were labeled with protein L-conjugated horseradish peroxidase using a tyramide amplification system, enabling fluorescence staining of the antibody captured inside the beads. Redox-HBs were then applied to fluorescence-activated droplet sorting, and selected redox-HBs were degraded by reducing the disulfide bonds to recover the target cells. The results indicated the potential of the developed HTS platform for selecting a single cell viable for biopharmaceutical production.

DOI： 10.1016/j.jbiosc.2024.04.001

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記述言語：英語   出版者・発行元：(公社)日本生物工学会  

掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acssusresmgt.4c00100

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出版者・発行元：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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掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Sustainable Chemistry and Engineering  

The utilization of ionic liquids (ILs) in metal extraction has been massively studied due to their excellent extraction ability, vast structural tunability, and low volatility. However, several ILs can be severely toxic, depending on the structure. It is significant to extract metal ions in a greener way for sustainability, yet the development of low-toxicity ILs for metal extraction remains a challenge. We prepared a series of potentially biocompatible ILs composed of amino acid ester (AAE)-based cations, with varying alkyl chain lengths and amino acid types and a fixed linoleate anion. An in vitro cytotoxicity study on HeLa cells indicates that the EC50 value of the synthesized ILs was ca. 2 orders of magnitude higher than that of commercial ILs (Aliquat 336 and Cyphos 104), suggestive of the low toxicity of the newly synthesized ILs. The ILs extracted the transition metals in the following order: Ni2+ > Co2+ > Mn2+. The separation factors for Ni/Co and Co/Mn ranged from 0.8 to 55 and from 0.6 to 50, respectively. In addition, l-leucine butyl linoleate exhibited highly selective extraction toward Au3+ and Pd2+ over Pt4+ with separation factors for Au/Pt and Pd/Pt of 37 and 40 in 0.05 mol/L HCl, respectively. Thus, AAE-based ILs are promising biocompatible extractants for metals.

DOI： 10.1021/acssuschemeng.4c01799

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Chemical Communications  

Herein, we report ethosome (ET) formulations composed of a safe amount of 1,2-dimyristoyl-sn-glycero-3-phosphatidylcholine (DMPC)-based ionic liquid with various concentrations of ethanol as a carrier for the transdermal delivery of a high molecular weight drug, insulin. The Insulin-loaded ET vesicles exhibited long-term stability compared to conventional DMPC ETs, showing significantly higher drug encapsulation efficiency and increased skin permeation ability.

DOI： 10.1039/d3cc06130b

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：International Journal of Molecular Sciences  

Candida albicans is a prevalent fungal pathogen that displays antibiotic resistance. The polyene antifungal amphotericin B (AmB) has been the gold standard because of its broad antifungal spectra, and its liposomal formulation, AmBisome, has been used widely and clinically in treating fungal infections. Herein, we explored enhancing the antifungal activity of AmBisome by integrating a small chitin-binding domain (LysM) of chitinase A derived from Pteris ryukyuensis. LysM conjugated with a lipid (LysM–lipid) was initially prepared through microbial transglutaminase (MTG)-mediated peptide tag-specific conjugation of LysM with a lipid–peptide substrate. The AmBisome formulation modified with LysM–lipid conjugates had a size distribution that was comparable to the native liposomes but an increased zeta potential, indicating that LysM–lipid conjugates were anchored to AmBisome. LysM–lipid-modified AmBisome exhibited long-term stability at 4 °C while retaining the capacity to bind chitin. Nevertheless, the antifungal efficacy of LysM–lipid-modified AmBisome against C. albicans was modest. We then redesigned a new LysM–lipid conjugate by introducing a peptide linker containing a thrombin digestion (TD) site at the C-terminus of LysM (LysM–TD linker–lipid), thereby facilitating the liberation of the LysM domain from AmBisome upon the addition of thrombin. This new AmBisome formulation anchored with LysM–TD linker–lipid exhibited superior performance in suppressing C. albicans growth in the presence of thrombin compared with the LysM–lipid formulation. These results provide a platform to design stimuli-responsive AmBisome formulations that respond to external environments and thus advance the treatment of pathogenic fungi infections.

DOI： 10.3390/ijms25073567

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記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1101/2024.03.04.583322

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記述言語：英語   出版者・発行元：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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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Bioconjugate Chemistry  

Microbial transglutaminase (MTG) from Streptomyces mobaraensis is a powerful biocatalytic glue for site-specific cross-linking of a range of biomolecules and synthetic molecules that have an MTG-reactive moiety. The preparation of active recombinant MTG requires post-translational proteolytic digestion of a propeptide that functions as an intramolecular chaperone to assist the correct folding of the MTG zymogen (MTGz) in the biosynthesis. Herein, we report engineered active zymogen of MTG (EzMTG) that is expressed in soluble form in the host Escherichia coli cytosol and exhibits cross-linking activity without limited proteolysis of the propeptide. We found that the saturation mutagenesis of residues K10 or Y12 in the propeptide domain generated several active MTGz mutants. In particular, the K10D/Y12G mutant exhibited catalytic activity comparable to that of mature MTG. However, the expression level was low, possibly because of decreased chaperone activity and/or the promiscuous substrate specificity of MTG, which is potentially harmful to the host cells. The K10R/Y12A mutant exhibited specific substrate-dependent reactivity toward peptidyl substrates. Quantitative analysis of the binding affinity of the mutated propeptides to the active site of MTG suggested an inverse relationship between the binding affinity and the catalytic activity of EzMTG. Our proof-of-concept study provides insights into the design of a new biocatalyst using the MTGz as a scaffold and a potential route to high-throughput screening of EzMTG mutants for bioconjugation applications.

DOI： 10.1021/acs.bioconjchem.3c00544

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Biomaterials Science and Engineering  

Droplet-based high-throughput screening systems are an emerging technology that provides a quick test to screen millions of cells with distinctive characteristics. Biopharmaceuticals, specifically therapeutic proteins, are produced by culturing cells that secrete heterologous recombinant proteins with different populations and expression levels; therefore, a technology to discriminate cells that produce more target proteins is needed. Here, we present a droplet-based microfluidic strategy for encapsulating, screening, and selecting target cells with redox-responsive hydrogel beads (HBs). As a proof-of-concept study, we demonstrate the enrichment of hybridoma cells with enhanced capability of antibody secretion using horseradish peroxidase (HRP)-catalyzed hydrogelation of tetra-thiolate poly(ethylene glycol); hybridoma cells were encapsulated in disulfide-bonded HBs. Recombinant protein G or protein M with a C-terminal cysteine residue was installed in the HBs via disulfide bonding to capture antibodies secreted from the cells. HBs were fluorescently stained by adding the protein L-HRP conjugate using a tyramide signal amplification system. HBs were then separated by fluorescence-activated droplet sorting and degraded by reducing the disulfide bonds to recover the target cells. Finally, we succeeded in the selection of hybridoma cells with enhanced antibody secretion, indicating the potential of this system in the therapeutic protein production.

DOI： 10.1021/acsbiomaterials.3c01386

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記述言語：英語   出版者・発行元：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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出版者・発行元：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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記述言語：英語   出版者・発行元：(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。

記述言語：英語   出版者・発行元：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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出版者・発行元：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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出版者・発行元：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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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Journal of Bioscience and Bioengineering  

Albumin is an attractive component for the development of biomaterials applied as biomedical implants, including drug carriers and tissue engineering scaffolds, because of its high biocompatibility and low immunogenicity. Additionally, albumin-based gelators facilitate cross-linking reactions under mild conditions, which maintains the high viability of encapsulated living cells. In this study, we synthesized albumin derivatives to undergo gelation under physiological conditions via the peroxidase-catalyzed formation of cross-links. Albumin was modified with phenolic hydroxyl groups (Alb–Ph–OH) using carbodiimide chemistry, and the effect of degree of substitution on gelation was investigated. Various properties of the Alb–Ph–OH hydrogels, namely the gelation time, swelling ratio, pore size, storage modulus, and enzymatic degradability, were easily controlled by adjusting the degree of substitution and the polymer concentration. Moreover, the viability of cells encapsulated within the Alb–Ph–OH hydrogel was high. These results demonstrate the potential applicability of Alb–Ph–OH hydrogels as cell-encapsulating materials for biomedical applications, including tissue engineering.

DOI： 10.1016/j.jbiosc.2023.09.007

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記述言語：その他  

DOI： 10.1101/2023.10.09.561484

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記述言語：その他  

DOI： 10.1002/tcr.202380802

記述言語：日本語   出版者・発行元：日本DDS学会  

イオン液体の製剤利用に近年注目が集まっている。なかでも、イオン液体の経皮吸収促進機能は、小分子の薬物のみならず、ペプチドやタンパク質などのバイオ医薬品までおよび、非侵襲性の経皮製剤の開発に大変有用である。特に、イオン液体の製剤利用においては、イオン液体の安全性を担保することが重要な課題となっている。そこで本稿では、コリン、アミノ酸、脂肪酸そして脂質など、安全性の高い素材によって形成されたイオン液体を紹介する。生体適合性の高いイオン液体の活用によって、DDSの徐放特性を発揮する中分子医薬あるいは経皮ワクチンの開発が可能となった。最近では、核酸医薬などの新しいモダリティにも、イオン液体の利用に大きな期待が寄せられている。

DOI： 10.2745/dds.38.220

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Chemical Communications  

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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記述言語：日本語   出版者・発行元：日本膜学会  

DOI： 10.5360/membrane.48.25

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Organic and Biomolecular Chemistry  

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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記述言語：英語   出版者・発行元：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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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Molecular Pharmaceutics  

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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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Omega  

In this study, we present a highly stable vegetable oil ionic liquid (IL)-based emulsion liquid membrane (VOILELM) for the removal of lactic acid from water streams. The system developed as a part of this work comprises a non-ionic surfactant Span 80, sodium hydroxide as an internal stripping agent, sunflower canola oil as a green diluent, and IL-tetramethylammonium acetate [TMAm][Ac]-as a carrier. VOILELM stability was evaluated in terms of breakage, emulsion diameter, and standalone stability. The effect of various parameters, namely, concentration of the surfactant, concentration of the internal stripping agent, concentration of the carrier, phase ratio, homogenizer speed, and homogenization time, on the VOILELM stability was studied. The results revealed that VOILELM was highly stable, with 1.34% minimum breakage, 1.16 μm emulsion diameter, and 131 min standalone stability. The optimal process parameters were 0.1 wt % Span 80, 0.1 M NaOH, 0.3 wt % IL, 0.25 phase ratio, 5000 rpm homogenizer speed, and 5 min homogenization time. At these optimized conditions, 96.08% lactic acid extraction efficiency was achieved. Thus, a highly effective VOILELM was developed, with minimal breakage and emulsion diameter and maximum stability.

DOI： 10.1021/acsomega.2c03425

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Journal of Bioscience and Bioengineering  

Amphotericin B (AMB) is a gold standard antifungal drug because of its broad-spectrum activity toward pathogenic yeasts and molds. Because of its low solubility in water and toxicity toward humans, several lipid-based formulations that either increase the aqueous solubility or decrease the side effects have been employed in practical use. In our previous research, we found that the combination of AMB with an artificial palmitoylated chitin-binding domain from Pteris ryukyuensis chitinase (LysM-Pal) resulted in synergistic antifungal action against Trichoderma viride. Herein, we prepared hybrid liposomal formulations by combining a commercially available AMB formulation and liposomes with different surface charges to explore key factors in the antifungal activity. The characterization of AMB-loaded liposomal formulations (AMB-LFs), including particle size distribution and zeta potential, showed that anionic and neutral AMB-LFs could stably encapsulate AMB. The combination of either anionic or neutral AMB-LFs with unmodified LysM decreased the minimum inhibitory concentration of AMB. The combination of neutral AMB-LF with LysM-Pal resulted in a further decrease in the MIC, up to 15-fold compared with that of the neutral AMB-LF alone. Our results demonstrate the potential utility of lipid-based liposomal formulations of AMB combined with lipid-modified proteinaceous binders to tackle fungal infections.

DOI： 10.1016/j.jbiosc.2022.06.005

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記述言語：英語   出版者・発行元：(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。

記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Langmuir  

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 β-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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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Nanoscale  

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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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Omega  

Chemical dispersants are used extensively for oil spill remediation. Most of these dispersants are composed of a mixture of surfactants and organic solvents, which raises concerns about aquatic toxicity and environmental impact. In this study, the toxicity and biodegradability of an oil spill dispersant composed of the surface-active ionic liquid 1-butyl-3-methylimidazolium lauroyl sarcosinate [Bmim]-[Lausar] and Tween-80 were investigated. In addition, important environmental factors including salinity, temperature, and wave-mixing energy were optimized to obtain maximum dispersion effectiveness. The acute toxicity against zebrafish (Danio rerio) showed that the developed dispersant was practically non-toxic with a median lethal dose of more than 100 mg L-1 after 96 h. The dispersant also demonstrated outstanding biodegradability of 66% after 28 days. A model was developed using a response surface methodology that efficiently (R2 = 0.992) related the salinity, temperature, and wave-mixing energy of seawater to dispersion effectiveness. The system was then optimized, and a high dispersion effectiveness of 89.70% was obtained with an experimental error of less than 2%. Our findings suggest that the surface-active ionic liquid and Tween-80 mixture could be a viable alternative to toxic chemical dispersants for oil spill remediation.

DOI： 10.1021/acsomega.2c00752

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記述言語：日本語   出版者・発行元：公益社団法人 化学工学会  

<p>各種イオン液体，1-アルキル-3-メチルイミダゾリウムヘキサフルオロホスフェートおよび1-アルキル-3-メチルイミダゾリウムビス（トリフルオロメタンスルフォニル）イミドを輸送キャリアとして用いた乳化液膜による塩酸媒体からのロジウム（III）の抽出を行った．ロジウム（III）の抽出を促進するために，原料水溶液中にスズ（II）を添加し，ロジウムおよびスズの抽出挙動におよぼす各種操作条件の影響を検討した．各種金属の抽出速度は，イオン液体種，界面活性剤濃度，逆抽出剤濃度に大きく影響されることがわかった．イオン液体分子におけるアルキル鎖長並びに対アニオン部の構造の違いが抽出に影響をおよぼすことが示された．また，逆抽出剤として用いた2-アミノ-2-ヒドロキシメチル-1,3-プロパンジオールの存在量が多量のスズからのロジウムの選択的な抽出に影響をおよぼし，最適値が存在することが明らかとなった．本系における最適操作条件下において，迅速かつ定量的なロジウム抽出が達成された．</p>

DOI： 10.1252/kakoronbunshu.48.81

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記述言語：英語  

DOI： 10.1200/PO.21.00535

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACS Infectious Diseases  

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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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：RSC Advances  

Chitosan adsorbents impregnated with a phosphonium-based ionic liquid (Chi_IL), trioctyldodecyl phosphonium chloride, were prepared for the adsorption of hexavalent chromium and compared to the performance of native chitosan. The physical and chemical properties of the adsorbents were characterized by Fourier-transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, and energy-dispersive X-ray spectroscopy. Effects of various parameters, such as pH, adsorbent dosage, contact time, temperature, and multi-component systems, were systematically examined. Chi_IL showed a high adsorption capacity (282.6 mg g?1) compared to native chitosan (238.1 mg g?1). The adsorption kinetics of the metals followed a pseudo-second-order kinetic model, and the experimental data were a good fit for the Freundlich isotherm model. Following the isotherm and activation energy parameter, adsorption of Cr(VI) onto Chi_IL follows a chemisorption process, possibly through an anionic exchange with the anion of the IL. The thermodynamic parameters suggested that the adsorption of Cr(VI) is a spontaneous and exothermic reaction. In the column adsorption, Chi_IL exhibited a longer column exhaustion time than that of native chitosan owing to the enhanced adsorption capacity caused by the introduction of IL. Moreover, the column with the parameters of 6 cm bed depth, 5 mL min?1 flow rate, and 50 mg L?1 was able to achieve the best performance in Cr(VI) adsorption.

DOI： 10.1039/D2RA00064D

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Solvent Extraction Research and Development, Japan  

In this study, we investigated an efficient recovery method of yttrium from a sulfuric acid leaching solution of spent Ni-MH battery electrode materials. In this newly proposed method, yttrium, one of the heavy rare earths (HREEs), was coprecipitated with light rare earths (LREEs) in the preliminary crude separation, and the residual yttrium was precisely recovered by solvent extraction using di-(2-ehylhexyl) phosphoric acid (D2EHPA) as the extractant. Yttrium in the leaching solution of 0.7 g/L that remained at 0.2 g/L after the coprecipitation operation; however, it could be reduced to 0.001 ? 0.002 g/L by the solvent extraction process in the following step. In this technical report, we focused on the solvent extraction operation. The extractant, D2EHPA, has a high affinity for yttrium, and we confirmed the possibility of improving the recovery yield of yttrium from 43% by coprecipitation alone to 98% by introducing solvent extraction.

DOI： 10.15261/serdj.29.79

Scopus

記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Hydrometallurgy  

The recycling of nickel, cobalt and rare earths from spent nickel?metal-hydride batteries was investigated. Nickel and cobalt were recovered as a nickel?cobalt mixed sulfide, which can be used as an intermediate raw material in existing nickel refineries. Rare earths were recovered as double sulfates, which can be recycled into industrial materials. In the recovery of rare earths, yttrium, a heavy rare earth, could be precipitated and recovered by co-precipitation with a light rare-earth double sulfate, which was considered impossible by the double-sulfate precipitation method because of high solubility of yttrium double sulfate. On the other hand, the coprecipitation behavior of yttrium was found to be unstable at the pilot scale because the stirring force was weaker than that in the laboratory experiments. In this study, the optimum conditions for leaching, double-sulfate precipitation, and sulfide precipitation reactions were determined in a laboratory test and the good performance was demonstrated in a pilot test. Based on the results, the estimated metal yields were 87% nickel, 90% cobalt, 54% yttrium, 99% lanthanum and 99% cerium. The nickel and cobalt impurities in the double sulfate that were recovered by this process were 0.04% and 0.005%, respectively, and the rare-earth impurities in the nickel?cobalt mixed sulfide were low at 0.049% yttrium, 0.007% lanthanum and 0.003% cerium. This process combined with a precipitation method showed a high separation performance.

DOI： 10.1016/j.hydromet.2022.105826

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Journal of Molecular Liquids  

Salicylic acid is an important component in cosmetics and skincare products and is widely found in aqueous streams as waste material. The present study reported the extraction of salicylic acid from wastewaters using a new technique termed as ‘ionic liquid-based emulsion liquid membrane’ (IL-ELM). Ionic liquids were introduced as carriers in IL-ELMs to enhance the emulsion stability. COSMO-RS simulation tool was employed to identify the effective IL among the 45 ILs composed of different cations and anions. It was found that IL [TMAm][Cl] (tetramethylammonium chloride) was found to be the most effective extracting agent for the extraction of salicylic acid that possesses the higher capacity, selectivity and lower activity coefficient towards analyte molecules. The COSMO-RS prediction results were in good agreement with the experimental data. Furthermore, this study optimized several operating conditions, including surfactant concentration, stripping agent concentration, IL concentration, emulsification time, homogenization speed and extraction time that affected the extraction efficiency. Overall, the proposed IL-ELM showed 90.04% extraction efficiency for salicylic acid under the optimized conditions of 0.005?M NaOH as stripping agent, 1.0?wt% Span-20 as emulsifier, 0.2?wt% [TMAm][Cl], 4000?rpm homogenization speed, 3:1 treat ratio and 25?min of extraction time.

DOI： 10.1016/j.molliq.2021.118280

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Chemical Communications  

Pairs of peptide amphiphiles with immiscible hydrophobic tails were synthesized and their assembly formation was investigated. These pairs formed self-sorting supramolecular fibres using a standard heating?cooling protocol, while one pair with longer hydrophobic tails formed a co-assembly when an additional heating process was applied.

DOI： 10.1039/d1cc05560g

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記述言語：その他   掲載種別：研究論文（学術雑誌）   出版者・発行元：Journal of Molecular Liquids  

Cellulose nanocrystals (CNCs) have attracted a great interest for various industrial applications due to their wide range of characteristics including compatibility, recyclability, and reproducibility. The efficient preparation of the quality cellulose nanocrystals (CNCs) from microcrystalline cellulose (MCC) utilizing ionic liquid (IL) 1-butyl-3-methylimidazoluim hydrogen sulfate ([Bmim][HSO4]) and dimethyl sulfoxide (DMSO) binary mixture was investigated and compared the results with those obtained from the pure IL. The produced CNCs were characterized using atomic force microscopy (AFM), Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA) and x-ray diffractometry (XRD). It was observed that the average diameter of CNCs obtained with IL-cosolvent (C-CNCs), and pure IL (P-CNCs) were 50 nm and 0.77 ?m, respectively, whereas the length of C-CNCs and P-CNCs were found to be 757 nm and 2.11 ?m, respectively. The non-isothermal Coats-Redfern model with numerous mechanisms were used to model the thermal degradation kinetics of CNCs. The C-CNCs and P-CNCs exhibited lower activation energies of 86.45 and 19.10 KJ/mol respectively, than that of MCC 386.8 KJ/mol. The role of DMSO in the production of CNCs was discussed. The proposed IL based binary mixture could be an effective for the production of high quality CNCs for different applications.

DOI： 10.1016/j.molliq.2021.118208

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記述言語：日本語   出版者・発行元：公益社団法人 日本油化学会  

<p>タンパク質や核酸などのバイオ分子は医薬品として利用され，臨床現場で大きな成果をあげるようになった。経皮吸収とは薬を皮膚から送達する方法であり，注射投与と比較して，安全かつ簡便な方法であることから，バイオ分子を経皮吸収させるための技術開発が注目されている。バイオ分子を油中にナノメートルサイズの粒子として分散させるSolid-in-Oil（S/O）技術は，経皮吸収促進効果をもつ油状基剤とバイオ分子を組み合わせることができることから，バイオ分子の経皮吸収において非常に有効であることが知られており，インスリンのようなタンパク質の経皮吸収効率の向上が報告されている。近年では，塗り薬型ワクチンの開発などが盛んに研究されており，抗原特異的な抗体産生や細胞性免疫の誘導が可能であることが明らかとなっている。今後の発展によって，S/O技術によるバイオ分子の経皮吸収製剤が実用化されることが期待される。</p>

DOI： 10.5650/oleoscience.22.121

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記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.cocis.2021.101515

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsami.1c16659

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.ijpharm.2021.121129

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsami.1c11533

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.desal.2021.115073

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.bioconjchem.1c00235

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsabm.1c00563

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.molpharmaceut.1c00324

記述言語：英語   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.memsci.2021.119296

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.bioconjchem.1c00027

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.2116/analsci.20SCR07

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1039/d1ra00489a

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.3390/ijms22073459

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acssuschemeng.0c07606

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1038/s41598-020-63362-4

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.ejps.2020.105521

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.molliq.2020.114424

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsabm.0c00940

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1039/d0cc04491a

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.jbiosc.2020.05.010

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.molpharmaceut.0c00598

記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

記述言語：その他   掲載種別：研究論文（学術雑誌）  

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

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1252/jcej.20we030

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.3390/pharmaceutics12090814

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acssuschemeng.0c03205

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1038/s41428-020-0344-7

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.molliq.2020.113122

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.jbiosc.2020.05.010

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.ab.2020.113700

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.3390/cosmetics7030052

記述言語：英語   掲載種別：研究論文（学術雑誌）  

その他リンク： https://doi.org/10.1039/C9TA13077B

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsomega.0c00867

記述言語：その他   掲載種別：研究論文（学術雑誌）  

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1038/s41598-020-63362-4

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acssuschemeng.9b07773

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acsomega.9b04163

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1248/bpb.b19-00642

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1088/1755-1315/415/1/012019

記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.molpharmaceut.9b01104

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.bej.2019.107426

記述言語：その他   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.molliq.2019.112166