Amino Acid Ester based Phenolic Ionic Liquids as a Potential Solvent for the Bioactive Compound Luteolin: Synthesis, Characterization, and Food Preservation Activity

Shimul, Islam Md; Moshikur, Rahman Md; Minamihata, Kosuke; Moniruzzaman, Muhammad; Kamiya, Noriho; Goto, Masahiro

doi:10.1016/j.molliq.2021.118103

Cited by 18 publications

(21 citation statements)

References 47 publications

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“…Several groups worldwide have investigated amino acid ILCs (and ILs) and the major focus was put on their thermotropic 25,[32][33][34][35][36][37] and lyotropic phase behaviour 34,[38][39][40][41][42][43][44][45][46] as well as solvation properties. 37,[47][48][49][50][51] Biological properties of amino acid ILCs, on the other hand, remain almost unexplored. 24,25 In our previous work 25 we have shown that cytotoxic and/or antimicrobial properties of amino acid ILCs can be controlled by the type of amino acid, i.e.…”

Section: Introductionmentioning

confidence: 99%

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Does thermotropic liquid crystalline self-assembly control biological activity in amphiphilic amino acids? – tyrosine ILCs as a case study

Grunwald,

Hagenlocher,

Turkanovic

et al. 2023

Phys. Chem. Chem. Phys.

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Section: Introductionmentioning

confidence: 99%

“…Several groups worldwide have investigated amino acid ILCs (and ILs) and the major focus was put on their thermotropic 25,32–37 and lyotropic phase behaviour 34,38–46 as well as solvation properties. 37,47–51 Biological properties of amino acid ILCs, on the other hand, remain almost unexplored. 24,25…”

Section: Introductionmentioning

confidence: 99%

Does thermotropic liquid crystalline self-assembly control biological activity in amphiphilic amino acids? – tyrosine ILCs as a case study

Grunwald,

Hagenlocher,

Turkanovic

et al. 2023

Phys. Chem. Chem. Phys.

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“…have also used COSMO‐RS to screen potential IL solvents to improve the solubility, stability, and extraction from Artemisia annua leaves of the antimalaria drug artemisinin [29] . Recently, we have screened a series of biocompatible amino acid ester‐based phenolic ILs using COSMO‐RS to design green IL solvents and experimentally validated the prediction by solubilizing the natural bioactive compound luteolin [25] . The mechanism by which the drug molecules in ILs are solubilized has been thoroughly investigated in experimental and molecular dynamics simulation studies.…”

Section: Ionic Liquids In Drug Development and Formulationmentioning

confidence: 99%

“…Several biocompatible ILs derived from natural sources have been used to solubilize small and macromolecular therapeutics as potential substitutes for conventional toxic ILs and organic solvents. We have reported the use of amino acid ethyl esters as potent biocompatible IL‐forming cations to prepare a series of ILs with fatty or bioactive phenolic acids [25] . We investigated the drug‐solubilizing ability using the poorly water‐soluble drugs, luteolin and ibuprofen [11,14,25] .…”

Section: Ionic Liquids In Drug Development and Formulationmentioning

confidence: 99%

Pharmaceutical Applications of Ionic Liquids: A Personal Account

Moshikur

Goto

2023

The Chemical Record

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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.

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“…Indeed, IL-based formulations have several advantages over conventional chemical enhancer-based transdermal formulations (e.g., patches, sprays, and ointments). These advantages include improved drug delivery profiles, excellent formulation stability, and enhanced pharmacokinetics and pharmacodynamics profiles. − Various pharmaceutical formulations such as microemulsions, liposomes, invasomes, and drug-loaded nanocarriers are used in cancer treatment. Recently, Dharamdasani et al.…”

Section: Introductionmentioning

confidence: 99%

Transdermal Delivery of Antigenic Protein Using Ionic Liquid-Based Nanocarriers for Tumor Immunotherapy

Uddin

Islam

Moshikur

et al. 2022

ACS Appl. Bio Mater.

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

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Amino Acid Ester based Phenolic Ionic Liquids as a Potential Solvent for the Bioactive Compound Luteolin: Synthesis, Characterization, and Food Preservation Activity

Cited by 18 publications

References 47 publications

Does thermotropic liquid crystalline self-assembly control biological activity in amphiphilic amino acids? – tyrosine ILCs as a case study

Does thermotropic liquid crystalline self-assembly control biological activity in amphiphilic amino acids? – tyrosine ILCs as a case study

Pharmaceutical Applications of Ionic Liquids: A Personal Account

Transdermal Delivery of Antigenic Protein Using Ionic Liquid-Based Nanocarriers for Tumor Immunotherapy

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