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Ionic liquids (ILs) have attracted considerable attention as green alternatives to conventional toxic organic solvents. They have several advantageous properties that make them potentially useful in various areas of modern science, especially drug delivery. Owing to their intrinsic tunability and exceptional properties, ILs are undoubtedly capable of addressing the drawbacks associated with sparingly soluble drugs, such as polymorphism, limited solubility, and poor bioavailability. ILs can be used as replacements for conventional volatile organic solvents. Their task-specific optimization at the molecular level can be exploited to obtain effective drug formulations. The structural properties of ILs can be tailored by altering their constituent anions and cations to improve the pharmacokinetic and pharmacodynamic properties and biological activities of drugs. This chapter describes the progress of IL-related research in pharmaceutics. It comprises a discussion of the use of ILs, either as solubilizing agents or solvents/carriers for pharmaceutical drugs. Specifically, the chapter deals with the use of ILs as potential solvents/agents for dissolving sparingly soluble drugs, and with the exploitation of the possible mechanism by which ILs increase solubility. An understanding of the ionic interactions between drug molecules and ILs in an aqueous solution will also stimulate innovative IL-based technologies and the use of ILs in pharmaceuticals and medicine.
Rahman Md Moshikur; Korban Ali; Masahiro Goto. Ionic Liquids for Increasing the Solubility of Sparingly Soluble Drug Molecules. Application of Ionic Liquids in Drug Delivery 2021, 51 -70.
AMA StyleRahman Md Moshikur, Korban Ali, Masahiro Goto. Ionic Liquids for Increasing the Solubility of Sparingly Soluble Drug Molecules. Application of Ionic Liquids in Drug Delivery. 2021; ():51-70.
Chicago/Turabian StyleRahman Md Moshikur; Korban Ali; Masahiro Goto. 2021. "Ionic Liquids for Increasing the Solubility of Sparingly Soluble Drug Molecules." Application of Ionic Liquids in Drug Delivery , no. : 51-70.
The oral route is the preferred mode of drug administration because it is non-invasive, self-administration is easy, and less physician supervision is required. However, the pharmaceutical industry faces several challenges in supplying many newly developed drugs by oral means because of their low water and other solvent solubility, formulation complexity, and limited bioavailability. In response to these constraints, tailor-made solvents known as ionic liquids (ILs) are increasingly being used in various pharmaceuticals sectors including drug delivery systems and active pharmaceutical ingredient formation because of their environmentally friendly and tunable physicochemical and biological properties. ILs and IL-based self-emulsifying drug delivery systems have been used for solubilizing poorly soluble drugs, protecting therapeutics from hostile gastrointestinal environments, improving permeability across the intestinal barrier, and enhancing absorption into the systemic circulation. This chapter highlights the potential of ILs as a tool for addressing key pharmaceutical issues in drug delivery/formulation, such as low solubility, stability, and bioavailability, with a specific focus on the latest developments.
Rafiqul Islam; Masahiro Goto. Ionic Liquid-Based Oral Drug Delivery Systems. Application of Ionic Liquids in Drug Delivery 2021, 91 -112.
AMA StyleRafiqul Islam, Masahiro Goto. Ionic Liquid-Based Oral Drug Delivery Systems. Application of Ionic Liquids in Drug Delivery. 2021; ():91-112.
Chicago/Turabian StyleRafiqul Islam; Masahiro Goto. 2021. "Ionic Liquid-Based Oral Drug Delivery Systems." Application of Ionic Liquids in Drug Delivery , no. : 91-112.
The development of effective drug delivery systems for poorly water-soluble drugs remains a significant challenge for the pharmaceutical industry because of their limited solubility, bioavailability, permeability and stability and their polymorphic conversion. A well-established approach to address these limitations is to convert the active compounds to salts; however, the challenges related to bioavailability, permeability and polymorphic transformation of crystalline drugs remain. The incorporation of active pharmaceutical ingredients (APIs) into ionic liquids (ILs) has been shown to be an attractive method for resolving these challenges and/or significantly increasing the pharmacokinetic and pharmacodynamic properties of drugs. To date, API-ILs have been designed to enhance the solubility of poorly water-soluble drugs in both water and simulated fluids, and to disrupt physiological barriers to deliver drugs to target sites. This chapter highlights the progress of ILs in API-related research. The discussion is focussed on the importance and advantages of the API-IL approach for the development of novel drugs, considering not only the physicochemical properties but also the pharmacological profiles of the API-ILs.
Rahman Md Moshikur; Masahiro Goto. Ionic Liquids as Active Pharmaceutical Ingredients (APIs). Application of Ionic Liquids in Drug Delivery 2021, 13 -33.
AMA StyleRahman Md Moshikur, Masahiro Goto. Ionic Liquids as Active Pharmaceutical Ingredients (APIs). Application of Ionic Liquids in Drug Delivery. 2021; ():13-33.
Chicago/Turabian StyleRahman Md Moshikur; Masahiro Goto. 2021. "Ionic Liquids as Active Pharmaceutical Ingredients (APIs)." Application of Ionic Liquids in Drug Delivery , no. : 13-33.
Lipid-based biocompatible ionic liquids (LBILs) have attracted attention as carriers in transdermal drug delivery systems (TDDSs) because of their lipophilic character. In this study, we report the formulation of a peptide–LBIL complex microencapsulated in an oil phase as a potential carrier for the transdermal delivery of leuprolide acetate as a model hydrophilic peptide. The peptide–LBIL complexes were prepared via a water-in-oil emulsion composed of 1,2-dimyristoyl-sn-glycerol-3-ethyl-phosphatidylcholine (EDMPC), a fatty acid (stearic, oleic, and linoleic acid)-based LBIL, and cyclohexane followed by freeze-drying to remove the water and cyclohexane. Then, the peptide–LBIL complexes were nanodispersed and stabilized in isopropyl myristate (IPM) using sorbitol laurate (Span-20). Ionic-liquid-in-oil nanodispersions (IL/O-NDs) were prepared with varying weight ratios of LBILs and Span-20 as the surfactant and the cosurfactant, respectively. Keeping the overall surfactant constant at 10 wt % in IPM, a 5:5 wt % ratio of surfactant (IL) and cosurfactant (Span-20) in the IL/O-NDs significantly (p < 0.0001) increased the physiochemical stability, drug-loading capacity, and drug encapsulation efficiency. The in vitro and in vivo peptide delivery across the skin was increased significantly (p < 0.0001) using IL/O-NDs, compared with non-IL-treated groups. Of all of the LBIL-based formulations, [EDMPC][Linoleate]/O-ND was considered the most preferable for a TDDS based on the pharmacokinetic parameters. The transdermal delivery flux with [EDMPC][Linoleate]/O-ND was increased 65-fold compared with the aqueous delivery vehicle. The IL/O-NDs were able to deform the lipid and protein arrangements of the skin layers to enhance the transdermal permeation of the peptide. In vitro and in vivo cytotoxicity studies of the IL/O-NDs revealed the biocompatibility of the LBIL-based formulations. These results indicated that IL/O-NDs are promising biocompatible carriers for lipid–peptide TDDSs.
Shihab Uddin; Rafiqul Islam; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. Lipid-Based Ionic-Liquid-Mediated Nanodispersions as Biocompatible Carriers for the Enhanced Transdermal Delivery of a Peptide Drug. ACS Applied Bio Materials 2021, 4, 6256 -6267.
AMA StyleShihab Uddin, Rafiqul Islam, Raihan Chowdhury, Rie Wakabayashi, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto. Lipid-Based Ionic-Liquid-Mediated Nanodispersions as Biocompatible Carriers for the Enhanced Transdermal Delivery of a Peptide Drug. ACS Applied Bio Materials. 2021; 4 (8):6256-6267.
Chicago/Turabian StyleShihab Uddin; Rafiqul Islam; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. 2021. "Lipid-Based Ionic-Liquid-Mediated Nanodispersions as Biocompatible Carriers for the Enhanced Transdermal Delivery of a Peptide Drug." ACS Applied Bio Materials 4, no. 8: 6256-6267.
Enzymatic reaction offers site-specific conjugation of protein units to form protein conjugates or protein polymers with intrinsic functions. Herein, we report horseradish peroxidase (HRP)- and microbial transglutaminase (MTG)-catalyzed orthogonal conjugation reactions to create antifungal protein polymers composed of Pteris ryukyuensis chitinase-A (ChiA) and its two domains, catalytic domain, CatD, and chitin-binding domain, LysM2. We engineered the ChiA and CatD by introducing a peptide tag containing tyrosine (Y-tag) at N-termini and a peptide tag containing lysine and tyrosine (KY-tag) at C-termini to construct Y-ChiA-KY and Y-CatD-KY. Also, LysM2 with Y-tag and KY-tag (Y-LysM2-KY) or with a glutamine-containing peptide tag (Q-tag) (LysM2-Q) were constructed. The proteins with Y-tag and KY-tag were efficiently polymerized by HRP reaction through the formation of dityrosine bonds at the tyrosine residues in the peptide tags. The Y-CatD-KY polymer was further treated by MTG to orthogonally graft LysM2-Q to the KY-tag via isopeptide formation between the side chains of the glutamine and lysine residues in the peptide tags to form LysM2-grafted CatD polymer. The LysM2-grafted CatD polymer exhibited significantly higher antifungal activity than the homopolymer of Y-ChiA-KY and the random copolymer of Y-CatD-KY and Y-LysM2-KY, demonstrating that the structural differences of artificial chitinase polymers have a significant impact on the antifungal activity. This strategy of polymerization and grafting reaction of protein can contribute to the further research and development of functional protein polymers for specific applications in various fields in biotechnology.
Kosuke Minamihata; Yusuke Tanaka; Pugoh Santoso; Masahiro Goto; Dan Kozome; Toki Taira; Noriho Kamiya. Orthogonal Enzymatic Conjugation Reactions Create Chitin Binding Domain Grafted Chitinase Polymers with Enhanced Antifungal Activity. Bioconjugate Chemistry 2021, 32, 1688 -1698.
AMA StyleKosuke Minamihata, Yusuke Tanaka, Pugoh Santoso, Masahiro Goto, Dan Kozome, Toki Taira, Noriho Kamiya. Orthogonal Enzymatic Conjugation Reactions Create Chitin Binding Domain Grafted Chitinase Polymers with Enhanced Antifungal Activity. Bioconjugate Chemistry. 2021; 32 (8):1688-1698.
Chicago/Turabian StyleKosuke Minamihata; Yusuke Tanaka; Pugoh Santoso; Masahiro Goto; Dan Kozome; Toki Taira; Noriho Kamiya. 2021. "Orthogonal Enzymatic Conjugation Reactions Create Chitin Binding Domain Grafted Chitinase Polymers with Enhanced Antifungal Activity." Bioconjugate Chemistry 32, no. 8: 1688-1698.
Coronavirus disease 2019 (COVID-19) has spread across the world, and no specific antiviral drugs have yet been approved to combat this disease. Favipiravir (FAV) is an antiviral drug that is currently in clinical trials for use against COVID-19. However, the delivery of FAV is challenging because of its limited solubility, and its formulation is difficult with common organic solvents and water. To address these issues, four FAV ionic liquids (FAV-ILs) were synthesized as potent antiviral prodrugs and were fully characterized by nuclear magnetic resonance (NMR) spectroscopy, Fourier-transform infrared (FT-IR) spectrometry, powder X-ray diffraction (PXRD), thermogravimetric analysis (TGA), derivative thermogravimetry (DTG), and differential scanning calorimetry (DSC). The aqueous solubility and in vivo pharmacokinetic properties of the FAV-ILs were also evaluated. The FAV-ILs exhibited improved aqueous solubility by 78 to 125 orders of magnitude when compared with that of free FAV. Upon oral dosing in mice, the absolute bioavailability of the β-alanine ethyl ester FAV formulation was increased 1.9-fold compared with that of the control FAV formulation. The peak blood concentration, elimination half-life, and mean absorption time of FAV were also increased by 1.5-, 2.0-, and 1.5-fold, respectively, compared with the control. Furthermore, the FAV in the FAV-ILs exhibited significantly different biodistribution compared with the control FAV formulation. Interestingly, drug accumulation in the lungs and liver was improved 1.5-fold and 1.3-fold, respectively, compared with the control FAV formulation. These results indicate that the use of ILs exhibits potential as a simple, scalable strategy to improve the solubility and oral absorption of hydrophobic drugs, such as FAV.
Rahman Md Moshikur; Korban Ali; Rie Wakabayashi; Muhammad Moniruzzaman; Masahiro Goto. Favipiravir-Based Ionic Liquids as Potent Antiviral Drugs for Oral Delivery: Synthesis, Solubility, and Pharmacokinetic Evaluation. Molecular Pharmaceutics 2021, 1 .
AMA StyleRahman Md Moshikur, Korban Ali, Rie Wakabayashi, Muhammad Moniruzzaman, Masahiro Goto. Favipiravir-Based Ionic Liquids as Potent Antiviral Drugs for Oral Delivery: Synthesis, Solubility, and Pharmacokinetic Evaluation. Molecular Pharmaceutics. 2021; ():1.
Chicago/Turabian StyleRahman Md Moshikur; Korban Ali; Rie Wakabayashi; Muhammad Moniruzzaman; Masahiro Goto. 2021. "Favipiravir-Based Ionic Liquids as Potent Antiviral Drugs for Oral Delivery: Synthesis, Solubility, and Pharmacokinetic Evaluation." Molecular Pharmaceutics , no. : 1.
The stratum corneum (SC) covers the outer surface of the skin and prevents the permeation of unwanted materials; however, the SC barrier also inhibits the desired permeation of active pharmaceutical ingredients (APIs). Therefore, the development of a novel method to enhance the permeation of APIs through the skin has been the focus of significant attention. Palmitoyl-glycine-histidine (Pal-GH)—comprising palmitic acid, glycine, and histidine—can be co-assembled with various additives to form a thixotropic hydrogel. Self-assembled Pal-GH enhances the permeation of ivermectin through the skin; however, the permeation mechanism is unclear and has not yet been discussed in detail. In the present study, the self-assembled structure of Pal-GH was analyzed using X-rays and infrared, and its permeation enhancement effect was verified. There was a correlation between the amount of Pal-GH in the skin and permeation enhancement, suggesting the involvement of the Pal-GH molecule. The presence of Pal-GH in the skin was confirmed by liquid chromatography–mass spectrometry and fluorescence labeling (labeling with Thioflavin T, a fluorescent dye that responds to β-sheets). The self-assembled Pal-GH permeated the SC without disrupting its organization. However, the structure of the Pal-GH caused changes to the lipid organization of the SC. The findings indicated that self-assembled Pal-GH is an effective permeation enhancer for transdermal delivery and does not induce skin irritation.
Takayuki Imoto; Masahiro Goto. Self-Assembled Palmitoyl-Glycine-Histidine as a Permeation Enhancer for Transdermal Delivery. Langmuir 2021, 37, 8971 -8977.
AMA StyleTakayuki Imoto, Masahiro Goto. Self-Assembled Palmitoyl-Glycine-Histidine as a Permeation Enhancer for Transdermal Delivery. Langmuir. 2021; 37 (30):8971-8977.
Chicago/Turabian StyleTakayuki Imoto; Masahiro Goto. 2021. "Self-Assembled Palmitoyl-Glycine-Histidine as a Permeation Enhancer for Transdermal Delivery." Langmuir 37, no. 30: 8971-8977.
Chemotherapeutic cytotoxic agents such as paclitaxel (PTX) are considered essential for the treatment of various cancers. However, PTX injection is associated with severe systemic side effects and high rates of patient noncompliance. Micelle formulations (MFs) are nano-drug delivery systems that offer a solution to these problems. Herein, we report an advantageous carrier for the transdermal delivery of PTX comprising a new MF that consists of two biocompatible surfactants: cholinium oleate ([Cho][Ole]), which is a surface-active ionic liquid (SAIL), and sorbitan monolaurate (Span-20). A solubility assessment confirmed that PTX was readily solubilized in the SAIL-based micelles via multipoint hydrogen bonding and cation−π and π–π interactions between PTX and SAIL[Cho][Ole]. Dynamic light scattering (DLS) and transmission electron microscopy revealed that in the presence of PTX, the MF formed spherical PTX-loaded micelles that were well-distributed in the range 8.7–25.3 nm. According to DLS, the sizes and size distributions of the micelle droplets did not change significantly over the entire storage period, attesting to their physical stability. In vitro transdermal assessments using a Franz diffusion cell revealed that the MF absorbed PTX 4 times more effectively than a Tween 80-based formulation and 6 times more effectively than an ethanol-based formulation. In vitro and in vivo skin irritation tests revealed that the new carrier had a negligible toxicity profile compared with a conventional ionic liquid-based carrier. Based on these findings, we believe that the SAIL[Cho][Ole]-based MF has potential as a biocompatible nanocarrier for the effective transdermal delivery of poorly soluble chemotherapeutics such as PTX.
Korban Ali; Rahman Md Moshikur; Rie Wakabayashi; Muhammad Moniruzzaman; Masahiro Goto. Biocompatible Ionic Liquid-Mediated Micelles for Enhanced Transdermal Delivery of Paclitaxel. ACS Applied Materials & Interfaces 2021, 13, 19745 -19755.
AMA StyleKorban Ali, Rahman Md Moshikur, Rie Wakabayashi, Muhammad Moniruzzaman, Masahiro Goto. Biocompatible Ionic Liquid-Mediated Micelles for Enhanced Transdermal Delivery of Paclitaxel. ACS Applied Materials & Interfaces. 2021; 13 (17):19745-19755.
Chicago/Turabian StyleKorban Ali; Rahman Md Moshikur; Rie Wakabayashi; Muhammad Moniruzzaman; Masahiro Goto. 2021. "Biocompatible Ionic Liquid-Mediated Micelles for Enhanced Transdermal Delivery of Paclitaxel." ACS Applied Materials & Interfaces 13, no. 17: 19745-19755.
The well-known toxicity of conventional chemical oil spill dispersants demands the development of alternative and environmentally friendly dispersant formulations. Therefore, in the present study we have developed a pair of less toxic and green dispersants by combining lactonic sophorolipid (LS) biosurfactant individually with choline myristate and choline oleate ionic liquid surfactants. The aggregation behavior of resulted surfactant blends and their dispersion effectiveness was investigated using the baffled flask test. The introduction of long hydrophobic alkyl chain with unsaturation (attached to choline cation) provided synergistic interactions between the binary surfactant mixtures. The maximum dispersion effectiveness was found to be 78.23% for 80:20 (w/w) lactonic sophorolipid-choline myristate blends, and 81.15% for 70:30 (w/w) lactonic sophorolipid-choline oleate blends at the dispersant-to-oil ratio of 1:25 (v/v). The high dispersion effectiveness of lactonic sophorolipid-choline oleate between two developed blends is attributed to the stronger synergistic interactions between surfactants and slower desorption rate of blend from oil-water interface. The distribution of dispersed oil droplets at several DOR were evaluated and it was observed that oil droplets become smaller with increasing DOR. In addition, the acute toxicity analysis of developed formulations against zebra fish (Danio rerio) confirmed their non-toxic behavior with LC50 values higher than 400 ppm after 96 h. Overall, the proposed new blends/formulations could effectively substitute the toxic and unsafe chemical dispersants.
Mansoor Ul Hassan Shah; Ambavaram Vijaya Bhaskar Reddy; Suzana Yusup; Masahiro Goto; Muhammad Moniruzzaman. Ionic liquid-biosurfactant blends as effective dispersants for oil spills: Effect of carbon chain length and degree of saturation. Environmental Pollution 2021, 284, 117119 .
AMA StyleMansoor Ul Hassan Shah, Ambavaram Vijaya Bhaskar Reddy, Suzana Yusup, Masahiro Goto, Muhammad Moniruzzaman. Ionic liquid-biosurfactant blends as effective dispersants for oil spills: Effect of carbon chain length and degree of saturation. Environmental Pollution. 2021; 284 ():117119.
Chicago/Turabian StyleMansoor Ul Hassan Shah; Ambavaram Vijaya Bhaskar Reddy; Suzana Yusup; Masahiro Goto; Muhammad Moniruzzaman. 2021. "Ionic liquid-biosurfactant blends as effective dispersants for oil spills: Effect of carbon chain length and degree of saturation." Environmental Pollution 284, no. : 117119.
Human skin contains numerous antigen-presenting cells that are a potential target for several immune-based therapies, including vaccination and cancer immunotherapy. However, the outermost layer of the skin—the stratum corneum—acts as a major physical barrier against the permeation of antigens that have a molecular weight > 500 Da. In this study, an ionic liquid-assisted delivery system (ILDS) was developed, which enabled the successful transdermal delivery of an antigenic protein, ovalbumin (OVA), with a toll-like receptor agonist, imiquimod, as an adjuvant, to stimulate a specific immune response. Both the ionic liquids and ILDS were completely biocompatible for topical or transdermal application for therapeutic purposes. The skin permeation of the antigenic protein and adjuvant was found to be significantly enhanced because of the incorporation of a surface-active ionic liquid in the ILDS. An in vivo immunization study showed that there was a high level of OVA-specific IgG antibody production because of the enhanced permeation of the antigen and adjuvant across and into the skin. In a preclusive anticancer study, vaccination through ILDS showed stronger tumor-growth inhibition compared to control group. These results indicated that the ILDS could be a promising strategy for transdermal immunization as future therapeutics.
Raihan Chowdhury; Rahman Md. Moshikur; Rie Wakabayashi; Muhammad Moniruzzaman; Masahiro Goto. Biocompatible ionic liquids assisted transdermal co-delivery of antigenic protein and adjuvant for cancer immunotherapy. International Journal of Pharmaceutics 2021, 601, 120582 .
AMA StyleRaihan Chowdhury, Rahman Md. Moshikur, Rie Wakabayashi, Muhammad Moniruzzaman, Masahiro Goto. Biocompatible ionic liquids assisted transdermal co-delivery of antigenic protein and adjuvant for cancer immunotherapy. International Journal of Pharmaceutics. 2021; 601 ():120582.
Chicago/Turabian StyleRaihan Chowdhury; Rahman Md. Moshikur; Rie Wakabayashi; Muhammad Moniruzzaman; Masahiro Goto. 2021. "Biocompatible ionic liquids assisted transdermal co-delivery of antigenic protein and adjuvant for cancer immunotherapy." International Journal of Pharmaceutics 601, no. : 120582.
An efficient recovery of lithium (Li(I)) from salt lakes is currently a challenging issue. Herein, we report a feasible extraction of Li(I) from a simulated salt lake solution using a novel extraction system, in which a functionalized ionic liquid (FIL) is dissolved in a different ionic liquid diluent. As a functional extractant, 3-methyl-1-octylimidazolium thenoyltrifluoroacetone [Omim][TTA] was successfully prepared in a simple way and its extraction performance for Li(I) was evaluated. The effects of pH and metal concentration on extraction, as well as the stripping property, were systematically investigated. It was found that the FIL could effectively act as the extractant of Li(I) over a wide range of pH, and even under acidic conditions. The extraction ability of the FIL was markedly enhanced by its use in an ionic liquid diluent. The obtained results demonstrated that Li(I) was extracted from the aqueous solution into the ionic liquids with a high extraction efficiency even in a five-cycle reusability test. Furthermore, using a simulated salt lake solution, Li(I) was selectively extracted with a high separation factor of 227 over Na(I), whereas Na(I) and K(I) remained in the aqueous feed solution.
Chunqing Cai; Takafumi Hanada; Adroit T.N. Fajar; Masahiro Goto. An ionic liquid extractant dissolved in an ionic liquid diluent for selective extraction of Li(I) from salt lakes. Desalination 2021, 509, 115073 .
AMA StyleChunqing Cai, Takafumi Hanada, Adroit T.N. Fajar, Masahiro Goto. An ionic liquid extractant dissolved in an ionic liquid diluent for selective extraction of Li(I) from salt lakes. Desalination. 2021; 509 ():115073.
Chicago/Turabian StyleChunqing Cai; Takafumi Hanada; Adroit T.N. Fajar; Masahiro Goto. 2021. "An ionic liquid extractant dissolved in an ionic liquid diluent for selective extraction of Li(I) from salt lakes." Desalination 509, no. : 115073.
Spent automotive catalysts (SACs) are the most abundant secondary source of platinum group metals (PGMs), but the recycling of these materials is quite challenging. In the present study, we assessed the recovery of Pt, Pd, and Rh from a SAC leachate solution using polymer inclusion membranes (PIMs) containing the ionic liquid trioctyl(dodecyl) phosphonium chloride (P88812Cl). After pretreatment of the SAC using a reducing agent, metals could be extracted using relatively dilute acid solutions. The selective transport of PGMs from such solutions was demonstrated with two types of membranes having the same chemical composition: an isotropic dense membrane (ID-PIM) and an anisotropic porous membrane (AP-PIM). Using the ID-PIM, more than 90% of Pt and Pd in the SAC extraction solutions could be recovered with remarkably high purity. In contrast, the AP-PIM could recover Pt, Pd, and Rh in reasonable yields and purities with dramatically faster transport kinetics. Both membrane types demonstrated excellent durability with no loss of carrier molecules over a 10-day exposure to various harsh chemicals.
Adroit T.N. Fajar; Takafumi Hanada; Masahiro Goto. Recovery of platinum group metals from a spent automotive catalyst using polymer inclusion membranes containing an ionic liquid carrier. Journal of Membrane Science 2021, 629, 119296 .
AMA StyleAdroit T.N. Fajar, Takafumi Hanada, Masahiro Goto. Recovery of platinum group metals from a spent automotive catalyst using polymer inclusion membranes containing an ionic liquid carrier. Journal of Membrane Science. 2021; 629 ():119296.
Chicago/Turabian StyleAdroit T.N. Fajar; Takafumi Hanada; Masahiro Goto. 2021. "Recovery of platinum group metals from a spent automotive catalyst using polymer inclusion membranes containing an ionic liquid carrier." Journal of Membrane Science 629, no. : 119296.
Supramolecular fibrous materials in biological systems play important structural and functional roles, and therefore, there is a growing interest in synthetic materials that mimic such fibrils, especially those bearing enzymatic reactivity. In this study, we investigated the self-assembly and enzymatic post-modification of short aromatic peptide amphiphiles (PAs), Fmoc-LnQG (n = 2 or 3), which contain an LQG recognition unit for microbial transglutaminase (MTG). These aromatic PAs self-assemble into fibrous structures via π-π stacking interactions between the Fmoc groups and hydrogen bonds between the peptides. The intermolecular interactions and morphologies of the assemblies were influenced by the solution pH because of the change in the ionization states of the C-terminal carboxy group of the peptides. Moreover, MTG-catalyzed post-modification of a small fluorescent molecule bearing an amine group also showed pH dependency, where the enzymatic reaction rate was increased at higher pH, which may be because of the higher nucleophilicity of the amine group and the electrostatic interaction between MTG and the self-assembled Fmoc-LnQG. Finally, the accumulation of the fluorescent molecule on these assembled materials was directly observed by confocal fluorescence images. Our study provides a method to accumulate functional molecules on supramolecular structures enzymatically with the morphology control.
Rie Wakabayashi; Ayato Higuchi; Hiroki Obayashi; Masahiro Goto; Noriho Kamiya. pH-Responsive Self-Assembly of Designer Aromatic Peptide Amphiphiles and Enzymatic Post-Modification of Assembled Structures. International Journal of Molecular Sciences 2021, 22, 3459 .
AMA StyleRie Wakabayashi, Ayato Higuchi, Hiroki Obayashi, Masahiro Goto, Noriho Kamiya. pH-Responsive Self-Assembly of Designer Aromatic Peptide Amphiphiles and Enzymatic Post-Modification of Assembled Structures. International Journal of Molecular Sciences. 2021; 22 (7):3459.
Chicago/Turabian StyleRie Wakabayashi; Ayato Higuchi; Hiroki Obayashi; Masahiro Goto; Noriho Kamiya. 2021. "pH-Responsive Self-Assembly of Designer Aromatic Peptide Amphiphiles and Enzymatic Post-Modification of Assembled Structures." International Journal of Molecular Sciences 22, no. 7: 3459.
Synthesis of lipid–protein conjugates is one of the significant techniques in drug delivery systems of proteins; however, the intact conjugation of a lipid and protein is yet challenging due to the hydrophobicity of lipid molecules. In order to facilitate easy handling of the lipid moiety in conjugation, we have focused on a microbial transglutaminase (MTG) that can ligate specific lysine (K) and glutamine (Q) residues in lipopeptides and a protein of interest. As MTG substrates, monolipid- and dilipid-fused amphiphilic short lipopeptide substrates (lipid-G3S-RHK or lipid2-KG3S-RHK) were designed. These amphiphilic lipopeptides and a model protein (enhanced green fluorescent protein, EGFP) fused with LLQG (LQ-EGFP) were both water-soluble, and thus lipid–protein conjugates were efficiently obtained through the MTG reaction with a >80% conversion rate of LQ-EGFP even using cholesterol-G3S-RHK. In vitro cell adhesion and in vivo half-life stability of the successfully obtained lipid–protein conjugates were evaluated, showing that the monocholesterol-G3S-RHK modification of a protein gave the highest cell adhesion efficiency and longest half-life time by formation of a stable albumin/lipid–protein complex.
Mari Takahara; Shinichi Mochizuki; Rie Wakabayashi; Kosuke Minamihata; Masahiro Goto; Kazuo Sakurai; Noriho Kamiya. Extending the Half-Life of a Protein in Vivo by Enzymatic Labeling with Amphiphilic Lipopeptides. Bioconjugate Chemistry 2021, 32, 655 -660.
AMA StyleMari Takahara, Shinichi Mochizuki, Rie Wakabayashi, Kosuke Minamihata, Masahiro Goto, Kazuo Sakurai, Noriho Kamiya. Extending the Half-Life of a Protein in Vivo by Enzymatic Labeling with Amphiphilic Lipopeptides. Bioconjugate Chemistry. 2021; 32 (4):655-660.
Chicago/Turabian StyleMari Takahara; Shinichi Mochizuki; Rie Wakabayashi; Kosuke Minamihata; Masahiro Goto; Kazuo Sakurai; Noriho Kamiya. 2021. "Extending the Half-Life of a Protein in Vivo by Enzymatic Labeling with Amphiphilic Lipopeptides." Bioconjugate Chemistry 32, no. 4: 655-660.
Novel amide-functionalised phosphonium-based ionic liquid can extract rhodium(iii) efficiently.
Wataru Yoshida; Masahiro Goto. Amide-functionalised phosphonium-based ionic liquids as ligands for rhodium(iii) extraction. RSC Advances 2021, 11, 9386 -9394.
AMA StyleWataru Yoshida, Masahiro Goto. Amide-functionalised phosphonium-based ionic liquids as ligands for rhodium(iii) extraction. RSC Advances. 2021; 11 (16):9386-9394.
Chicago/Turabian StyleWataru Yoshida; Masahiro Goto. 2021. "Amide-functionalised phosphonium-based ionic liquids as ligands for rhodium(iii) extraction." RSC Advances 11, no. 16: 9386-9394.
Objective Nicotinamide, also known as niacinamide, is a water‐soluble vitamin that is used to prevent and treat acne and pellagra. It is often found in water‐based skin care cosmetics because of its high water‐solubility. Nicotinamide is a small molecule with a molar mass of 122.1 g/mol. However, it has a hydrophilic nature that becomes an obstacle when it penetrates through the skin. The topmost layer of the skin, the stratum corneum, acts as a strong hydrophobic barrier for such hydrophilic molecules. The oil‐based formulations are expected to enhance the transdermal delivery efficiency of nicotinamide. Methods We have developed oil‐based microemulsion formulations composed of a squalane‐vehicle. Monoolein was used as an emulsifier that has a potential to enhance the nicotinamide delivery through the stratum corneum. Results Because the mean size of the emulsions measured by dynamic light scattering was 20.9 ± 0.4 nm, the microemulsion formulation was stable under the long‐term storage. Monoolein acted as a skin penetration enhancer, and it effectively enabled the penetration of nicotinamide through human abdominal skin, compared with nicotinamide in a phosphate buffered saline solution. The flux was increased 25‐fold. Microscopic imaging revealed that the hydrophilic bioactive compounds penetrated through the intercellular spaces in the epidermis. Conclusion The monoolein‐based microemulsion was transparent and stable, suggesting that it is a promising formulation for a transdermal nicotinamide delivery.
Momoko Kitaoka; Trung Cong Nguyen; Masahiro Goto. Water‐in‐oil microemulsions composed of monoolein enhanced the transdermal delivery of nicotinamide. International Journal of Cosmetic Science 2021, 43, 302 -310.
AMA StyleMomoko Kitaoka, Trung Cong Nguyen, Masahiro Goto. Water‐in‐oil microemulsions composed of monoolein enhanced the transdermal delivery of nicotinamide. International Journal of Cosmetic Science. 2021; 43 (3):302-310.
Chicago/Turabian StyleMomoko Kitaoka; Trung Cong Nguyen; Masahiro Goto. 2021. "Water‐in‐oil microemulsions composed of monoolein enhanced the transdermal delivery of nicotinamide." International Journal of Cosmetic Science 43, no. 3: 302-310.
Hydrophobic deep eutectic solvents (DESs) have attracted much attention as sustainable extraction media for various metals. However, in previously developed DESs, only one DES component is involved in metal complex formation, which has limited their extraction performance and selectivity. Here, we propose a novel synergistic DES concept for improving the performance of environmentally benign liquid–liquid extraction of lithium (Li). Two different conventional extractants, a beta-diketone and a neutral extractant, were effective for creating the synergistic DESs. When the two extractants were mixed, they formed a liquid DES. DESs have much lower viscosity than conventional hydrophobic ionic liquids. The Conductor-like Screening Model for Real Solvents method was used to estimate the formation of DESs with the melting point depressed by the intermolecular interaction between their components. The extraction performance of Li was greatly enhanced with the synergistic DESs. The extraction capacity of Li reached 4.4 g/L using the optimum DES combination because it was solvent-free and highly concentrated. Using the optimum DES, highly selective recovery of Li over Na and K was demonstrated with a model brine solution. This is the first report of efficient and selective extraction of Li with DES-based liquid–liquid extraction.
Takafumi Hanada; Masahiro Goto. Synergistic Deep Eutectic Solvents for Lithium Extraction. ACS Sustainable Chemistry & Engineering 2021, 9, 2152 -2160.
AMA StyleTakafumi Hanada, Masahiro Goto. Synergistic Deep Eutectic Solvents for Lithium Extraction. ACS Sustainable Chemistry & Engineering. 2021; 9 (5):2152-2160.
Chicago/Turabian StyleTakafumi Hanada; Masahiro Goto. 2021. "Synergistic Deep Eutectic Solvents for Lithium Extraction." ACS Sustainable Chemistry & Engineering 9, no. 5: 2152-2160.
Kosuke Minamihata; Yusei Hamada; Genki Kagawa; Wahyu Ramadhan; Ayato Higuchi; Kousuke Moriyama; Rie Wakabayashi; Masahiro Goto; Noriho Kamiya. Dual-Functionalizable Streptavidin–SpyCatcher-Fused Protein–Polymer Hydrogels as Scaffolds for Cell Culture. ACS Applied Bio Materials 2020, 3, 7734 -7742.
AMA StyleKosuke Minamihata, Yusei Hamada, Genki Kagawa, Wahyu Ramadhan, Ayato Higuchi, Kousuke Moriyama, Rie Wakabayashi, Masahiro Goto, Noriho Kamiya. Dual-Functionalizable Streptavidin–SpyCatcher-Fused Protein–Polymer Hydrogels as Scaffolds for Cell Culture. ACS Applied Bio Materials. 2020; 3 (11):7734-7742.
Chicago/Turabian StyleKosuke Minamihata; Yusei Hamada; Genki Kagawa; Wahyu Ramadhan; Ayato Higuchi; Kousuke Moriyama; Rie Wakabayashi; Masahiro Goto; Noriho Kamiya. 2020. "Dual-Functionalizable Streptavidin–SpyCatcher-Fused Protein–Polymer Hydrogels as Scaffolds for Cell Culture." ACS Applied Bio Materials 3, no. 11: 7734-7742.
This study reports a new series of lipid-based biocompatible ionic liquids consisting of long-chain phosphonium compound, 1,2-dimyristoyl-sn-glycero-3-ethyl- phosphatidylcholine, as a cation and long chain fatty acids as anions.
Shihab Uddin; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. Lipid based biocompatible ionic liquids: synthesis, characterization and biocompatibility evaluation. Chemical Communications 2020, 56, 13756 -13759.
AMA StyleShihab Uddin, Raihan Chowdhury, Rie Wakabayashi, Noriho Kamiya, Muhammad Moniruzzaman, Masahiro Goto. Lipid based biocompatible ionic liquids: synthesis, characterization and biocompatibility evaluation. Chemical Communications. 2020; 56 (89):13756-13759.
Chicago/Turabian StyleShihab Uddin; Raihan Chowdhury; Rie Wakabayashi; Noriho Kamiya; Muhammad Moniruzzaman; Masahiro Goto. 2020. "Lipid based biocompatible ionic liquids: synthesis, characterization and biocompatibility evaluation." Chemical Communications 56, no. 89: 13756-13759.
Surface-active ionic liquid (SAIL) surfactants have attracted attention as promising alternatives to conventional surfactants because of their tailor-made and tunable properties. SAILs also address the limitations associated with conventional surfactants including toxicity and formation of unstable micelles. Here, we investigated the aggregation behavior of three biocompatible choline N-lauroyl-amino acid (NLAA)-based ILs with different amino acid side chains in aqueous solutions. The micellar behaviors of NLAA-ILs were investigated using surface tensiometry, conductometry, dynamic light scattering (DLS) and transmission electron microscopy (TEM). The critical micellar concentration (CMC) of the NLAA-ILs was found to be 2 to 4-fold lower compared with the conventional surfactant sodium dodecyl sulfate (SDS). The thermodynamic behavior confirmed that the micelle formation of NLAA-ILs was stable, spontaneous and entropy driven at room temperature. DLS and TEM studies revealed that the size and shape of the micelles depended on the presence of an N‑hydrogen group in the head group of the anion. Choline N-lauroyl glycinate ([Cho][NLG]) and dicholine N-lauroyl aspartate ([Cho]2[NLA]) were predominantly produced as unilamellar vesicles in water whereas choline N-lauroyl sarcosinate ([Cho][NLS]) formed small spherical micelles. Importantly, SAIL [Cho][NLG] showed lower toxicity toward mammalian cells compared with the analogous ILs or the conventional surfactant SDS and similar toxicity to the conventional surfactant Tween 80. SAIL [Cho][NLG] was more efficient at forming hydrophobic ion pairs with the macromolecular drug heparin compared with SAIL [Cho][NLS]. These results clearly suggest that the biocompatible NLAA-ILs represent promising potential substitutes for conventional surfactants in various biomedical applications.
Rahman Md Moshikur; Korban Ali; Rie Wakabayashi; Muhammad Moniruzzaman; Masahiro Goto. Formation and potential application of micelles composed of biocompatible N-lauroyl-amino acid ionic liquids surfactant. Journal of Molecular Liquids 2020, 320, 114424 .
AMA StyleRahman Md Moshikur, Korban Ali, Rie Wakabayashi, Muhammad Moniruzzaman, Masahiro Goto. Formation and potential application of micelles composed of biocompatible N-lauroyl-amino acid ionic liquids surfactant. Journal of Molecular Liquids. 2020; 320 ():114424.
Chicago/Turabian StyleRahman Md Moshikur; Korban Ali; Rie Wakabayashi; Muhammad Moniruzzaman; Masahiro Goto. 2020. "Formation and potential application of micelles composed of biocompatible N-lauroyl-amino acid ionic liquids surfactant." Journal of Molecular Liquids 320, no. : 114424.