Ionic liquid-mediated skin technologies: Recent advances and prospects

Abednejad, 2019, Polyvinylidene fluoride–Hyaluronic acid wound dressing comprised of ionic liquids for controlled drug delivery and dual therapeutic behavior, Acta Biomater., 100, 142, 10.1016/j.actbio.2019.10.007 Aditya, 2018, Zinc oxide nanoparticles dispersed in ionic liquids show high antimicrobial efficacy to skin-specific bacteria, ACS Appl. Mater. Interfaces, 10, 15401, 10.1021/acsami.8b01463 Agatemor, 2018, Ionic liquids for addressing unmet needs in healthcare, Bioeng. Transl. Med., 3, 7, 10.1002/btm2.10083 Alam, 2019, Biofilms: A Phenotypic Mechanism of Bacteria Conferring Tolerance Against Stress and Antibiotics, 315 Alexander, 2012, Approaches for breaking the barriers of drug permeation through transdermal drug delivery, J. Control. Release, 164, 26, 10.1016/j.jconrel.2012.09.017 Araki, 2015, Ionic liquid-mediated transcutaneous protein delivery with solid-in-oil nanodispersions, Medchemcomm, 6, 2124, 10.1039/C5MD00378D Ardiyanti, 2014, Design and characterization of Chitin-Glucan polymeric structures for wound dressing materials Bains, 2018, Development of biological self-cleaning wound- dressing gauze for the treatment of bacterial infection, ACS Sustainable Chem. Eng., 7, 969, 10.1021/acssuschemeng.8b04608 Baleeiro, 2013, Topical Vaccination with Functionalized Particles Targeting Dendritic Cells, J, Invest. Dermatol., 133, 1933, 10.1038/jid.2013.79 Banerjee, 2017, Transdermal protein delivery using choline and geranate (CAGE) deep eutectic solvent, Adv. Healthcare Mater., 6, 1601411, 10.1002/adhm.201601411 Banerjee, 2018, Ionic liquids for oral insulin delivery, Proc. Natl. Acad. Sci., 115, 7296, 10.1073/pnas.1722338115 Benson, 2019, Topical and transdermal drug delivery: From simple potions to smart technologies, Curr. Drug Deliv., 16, 444, 10.2174/1567201816666190201143457 Carter, 2019, Biocompatible nanoparticles and vesicular systems in transdermal drug delivery for various skin diseases, Int. J. Pharm., 555, 49, 10.1016/j.ijpharm.2018.11.032 Chantereau, 2019, Design of nonsteroidal anti-inflammatory drug-based ionic liquids with improved water solubility and drug delivery, ACS Sustain. Chem. Eng., 7, 14126, 10.1021/acssuschemeng.9b02797 Chaudhari, A.A., Vig, K., Baganizi, D.R., Sahu, R., Dixit, S., Dennis, V., Singh, S.R., Pillai, S.R., 2016. Future prospects for scaffolding methods and biomaterials in skin tissue engineering: a review. Int. J. Mol. Sci. 1974. Chen, 2020, Hierarchically crosslinked gels containing hydrophobic ionic liquids towards reliable sensing applications, Chin. J. Polym. Sci., 38, 332, 10.1007/s10118-020-2357-2 Chowdhury, 2016, Regenerated cellulose/polypyrrole/silver nanoparticles/ionic liquid composite films for potential wound healing applications, Wound Med., 14, 16, 10.1016/j.wndm.2016.07.001 Cornwell, P.A., Barry, B.W., Bouwstra, J.A., Gooris, G.S., 1996. Modes of action of terpene penetration enhancers in human skin; Differential scanning calorimetry, small-angle X-ray diffraction and enhancer uptake studies. Int. J. Pharm. 127, 9–26. https://doi.org/10.1016/0378-5173(95)04108-7. das Kurmi, B., Tekchandani, P., Paliwal, R., Rai Paliwal, S., 2017. Transdermal drug delivery: opportunities and challenges for controlled delivery of therapeutic agents using nanocarriers.Current Drug Metabolism 18, 481–495. Dobler, 2013, Ionic liquids as ingredients in topical drug delivery systems, Int. J. Pharm., 441, 620, 10.1016/j.ijpharm.2012.10.035 Engelbrecht, 2012, Study of the Influence of the Penetration Enhancer Isopropyl Myristate on the Nanostructure of Stratum Corneum Lipid Model Membranes Using Neutron Diffraction and Deuterium Labelling, Skin Pharm. Physiol., 25, 200, 10.1159/000338538 Fang, 2019, Antibacterial activities of N-alkyl imidazolium-based poly (ionic liquid) nanoparticles, Polym. Chem., 10, 209, 10.1039/C8PY01290C Ferraz, 2020, Synthesis and Antibacterial Activity of Ionic Liquids and Organic Salts based on Penicillin G and Amoxicillin hydrolysate derivatives against Resistant Bacteria, Pharmaceutics, 12, 221, 10.3390/pharmaceutics12030221 Forero-Doria, 2019, N-alkylimidazolium Salts Functionalized with p-Coumaric and Cinnamic Acid: A Study of Their Antimicrobial and Antibiofilm Effects, Molecules, 24, 3484, 10.3390/molecules24193484 Gannesen, 2018, Regulation of monospecies and mixed biofilms formation of skin Staphylococcus aureus and Cutibacterium acnes by human natriuretic peptides, Front. Microbiol., 9, 2912, 10.3389/fmicb.2018.02912 Gebreyohannes, 2019, Challenges of intervention, treatment, and antibiotic resistance of biofilm-forming microorganisms, Heliyon, 5, e02192, 10.1016/j.heliyon.2019.e02192 Goindi, 2014, Development of novel ionic liquid-based microemulsion formulation for dermal delivery of 5-fluorouracil, AAPS PharmSciTech, 15, 810, 10.1208/s12249-014-0103-1 Goindi, 2015, An ionic liquid-in-water microemulsion as a potential carrier for topical delivery of poorly water-soluble drug: development, ex-vivo and in- vivo evaluation, Int. J. Pharm., 495, 913, 10.1016/j.ijpharm.2015.09.066 Gomes, 2021, The Emerging Role of Ionic Liquid- Based Approaches for Enhanced Skin Permeation of Bioactive Molecules: A Snapshot of the Past Couple of Years, Int. J. Mol. Sci., 22, 11991, 10.3390/ijms222111991 Gomes, 2019, Biocompatible ionic liquids: fundamental behaviours and applications, Chem. Soc. Rev., 48, 4317, 10.1039/C9CS00016J Haque, 2018, Chemical Enhancer: A Simplistic Way to Modulate Barrier Function of the Stratum Corneum, Adv. Pharm. Bull., 8, 169, 10.15171/apb.2018.021 Hattori, T., Tagawa, H., Inai, M., Kan, T., Kimura, S., Itai, S., Mitragotri, S., Iwao, Y., 2019. Transdermal delivery of nobiletin using ionic liquids. Sci. Rep. 9, 1–11. Huang, W., Wu, X., Qi, J., Zhu, Q., Wu, W., Lu, Y., Chen, Z., 2019. Ionic liquids: Green and tailor- made solvents in drug delivery. Drug Discovery Today. Inui, 2012, Novel Patch for Transdermal Administration of Morphine, J. Pain Symptom Manage., 44, 10.1016/j.jpainsymman.2011.10.022 Iqbal, 2017, An application of ionic liquid for preparation of homogeneous collagen and alginate hydrogels for skin dressing, J. Mol. Liq., 243, 720, 10.1016/j.molliq.2017.08.101 Iqbal, 2019, Development of collagen/PVA composites patches for osteochondral defects using a green processing of ionic liquid, Int. J. Polym. Mater. Polym. Biomater., 68, 590, 10.1080/00914037.2018.1474358 Ji, 2017, Synthesis and characterization of alkali lignin-based hydrogels from ionic liquids, BioResources, 12, 5395, 10.15376/biores.12.3.5395-5406 Kanaan, 2021, Semi-interpenetrating chitosan/ionic liquid polymer networks as electro-responsive biomaterials for potential wound dressings and iontophoretic applications, Mater. Sci. Eng., C, 121, 10.1016/j.msec.2020.111798 Kandasamy, 2018, Formulation and characterization of acetate based ionic liquid in oil microemulsion as a carrier for acyclovir and methotrexate, Sep. Purif. Technol., 196, 149, 10.1016/j.seppur.2017.08.044 Kellar, R., Nieto, N.C., Koppisch, A., del Sesto, R., 2020. Ionic liquids that sterilize and prevent biofilm formation in skin wound healing devices. Kováčik, 2020, Permeation enhancers in transdermal drug delivery: benefits and limitations, Expert Opinion on Drug Delivery, 17, 145, 10.1080/17425247.2020.1713087 Lane, M.E., 2013. Int. J. Pharm Skin penetration enhancers. 447, 12–21. Lee, H., Song, C., Hong, Y.S., Kim, M.S., Cho, H.R., Kang, T., Shin, K., Choi, S.H., Hyeon, T., Kim, D.-H., 2017. Wearable/disposable sweat-based glucose monitoring device with multistage transdermal drug delivery module. Sci. Adv. 3, e1601314. Lee, 2010, Preparation of biopolymer-based materials using ionic liquids for the biomedical application, 115 Leppert, 2018, Transdermal and topical drug administration in the treatment of pain, Molecules, 23, 681, 10.3390/molecules23030681 Lim, 2015, How the spontaneous insertion of amphiphilic imidazolium- based cations changes biological membranes: a molecular simulation study, PCCP, 17, 29171, 10.1039/C5CP04806K Lu, 2022, Ionic liquid transdermal delivery system: Progress, prospects, and challenges, J. Mol. Liq., 351, 10.1016/j.molliq.2022.118643 Lv, 2014, Characterization of chitosan microparticles reinforced cellulose biocomposite sponges regenerated from ionic liquid, Cellulose, 21, 4405, 10.1007/s10570-014-0440-y Mali, A.D., 2015. An updated review on transdermal drug delivery systems. skin 8. Malvey, 2019, Transdermal drug delivery system: A mini review, Pharma Innov. Int. J., 8, 181 Mandal, 2020, Treatment of psoriasis with NFKBIZ siRNA using topical ionic liquid formulations, Sci. Adv., 6, 10.1126/sciadv.abb6049 McNeilly, 2014, Microprojection arrays to immunise at mucosal surfaces, J. Control. Release, 196, 252, 10.1016/j.jconrel.2014.09.028 Md Moshikur, 2020, Design and Characterization of Fatty Acid-Based Amino Acid Ester as a New “Green” Hydrophobic Ionic Liquid for Drug Delivery, ACS Sustainable Chem. Eng., 8, 13660, 10.1021/acssuschemeng.0c03419 Mena, 2020, Cation and anion effect on the biodegradability and toxicity of imidazolium–and choline–based ionic liquids, Chemosphere, 240, 10.1016/j.chemosphere.2019.124947 Meng, Z., Zheng, X., Tang, K., Liu, J., Qin, S., 2012. Dissolution of natural polymers in ionic liquids: A review. e-Polymers 12. Milewski, 2010, In vitro permeation of a pegylated naltrexone prodrug across microneedle-treated skin, J. Control. Release, 146, 37, 10.1016/j.jconrel.2010.05.034 Miwa, 2016, Lidocaine self-sacrificially improves the skin permeation of the acidic and poorly water-soluble drug etodolac via its transformation into an ionic liquid, Eur. J. Pharm. Biopharm., 102, 92, 10.1016/j.ejpb.2016.03.003 Moghadam, S.H., Saliaj, E., Wettig, S.D., Dong, C., Ivanova, M. v., Huzil, J.T., Foldvari, M., 2013. Effect of Chemical Permeation Enhancers on Stratum Corneum Barrier Lipid Organizational Structure and Interferon Alpha Permeability. Mol. Pharm. 10, 2248–2260. https://doi.org/10.1021/mp300441c. Moghimipour, 2013, Effect of the Various Solvents on the In Vitro Permeability of Vitamin B12 through Excised Rat Skin, Trop. J. Pharm. Res., 12 Mohammadi-Samani, 2020, Preparation and characterization of sumatriptan loaded solid lipid nanoparticles for transdermal delivery, J. Drug Delivery Sci. Technol., 101719 Moniruzzaman, 2010, Ionic liquid-in-oil microemulsion as a potential carrier of sparingly soluble drug: Characterization and cytotoxicity evaluation, Int. J. Pharm., 400, 243, 10.1016/j.ijpharm.2010.08.034 Monti, 2017, Ionic liquids as potential enhancers for transdermal drug delivery, Int. J. Pharm., 516, 45, 10.1016/j.ijpharm.2016.11.020 Morais, 2019, Anti-inflammatory and antioxidant nanostructured cellulose membranes loaded with phenolic-based ionic liquids for cutaneous application, Carbohydr. Polym., 206, 187, 10.1016/j.carbpol.2018.10.051 Moshikur, 2020, Ionic liquids with N-methyl-2-pyrrolidonium cation as an enhancer for topical drug delivery: Synthesis, characterization, and skin-penetration evaluation, J. Mol. Liq., 299, 10.1016/j.molliq.2019.112166 Notman, 2007, The Permeability Enhancing Mechanism of DMSO in Ceramide Bilayers Simulated by Molecular Dynamics, Biophys. J ., 93, 2056, 10.1529/biophysj.107.104703 Nunes, C.S., Rufato, K.B., Souza, P.R., de Almeida, E.A.M.S., da Silva, M.J. v, Scariot, D.B., Nakamura, C. v, Rosa, F.A., Martins, A.F., Muniz, E.C., 2017. Chitosan/chondroitin sulfate hydrogels prepared in [Hmim][HSO4] ionic liquid. Carbohydrate Polymers 170, 99–106. Palac, 2014, Liposomes for (trans) dermal drug delivery: the skin-PVPA as a novel in vitro stratum corneum model in formulation development, J. Liposome Res., 24, 313, 10.3109/08982104.2014.899368 Parhi, 2015, Physical means of stratum corneum barrier manipulation to enhance transdermal drug delivery, Curr. Drug Deliv., 12, 122, 10.2174/1567201811666140515145329 Parlet, 2019, Commensal staphylococci influence Staphylococcus aureus skin colonization and disease, Trends Microbiol., 27, 497, 10.1016/j.tim.2019.01.008 Patil, 2020, Synthesis of silver nanoparticles colloids in imidazolium halide ionic liquids and their antibacterial activities for gram-positive and gram-negative bacteria, Chemosphere, 243, 10.1016/j.chemosphere.2019.125302 Paz Ramos, 2020, Raman and AFM-IR chemical imaging of stratum corneum model membranes, Can. J. Chem., 10.1139/cjc-2019-0471 Pegoraro, C., MacNeil, S., Battaglia, G., 2012. Transdermal drug delivery: from micro to nano. Nanoscale 4, 1881–1894. Pham, 2017, Application of d-α-tocopheryl polyethylene glycol 1000 succinate (TPGS) in transdermal and topical drug delivery systems (TDDS), J. Pharm. Investig., 47, 111, 10.1007/s40005-016-0300-x Qi, 2020, Comparison of Ionic Liquids and Chemical Permeation Enhancers for Transdermal Drug Delivery, Adv. Funct. Mater., 30, 2004257, 10.1002/adfm.202004257 Qi, 2019, Mechanistic study of transdermal delivery of macromolecules assisted by ionic liquids, J. Control. Release, 311, 162, 10.1016/j.jconrel.2019.08.029 Qu, 2019, Degradable conductive injectable hydrogels as novel antibacterial, anti-oxidant wound dressings for wound healing, Chem. Eng. J., 362, 548, 10.1016/j.cej.2019.01.028 Reddy, G.K.K., Nancharaiah, Y. v, Venugopalan, V.P., 2017. Long alkyl-chain imidazolium ionic liquids: Antibiofilm activity against phototrophic biofilms. Colloids Surf. B: Biointerf. 155, 487–496. Reeves, 2020, Tribological Performance of environmental friendly ionic liquids for High-Temperature Applications, J. Cleaner Prod., 123666 Rigon, 2018, Solid lipid nanoparticles optimized by 22 factorial design for skin administration: Cytotoxicity in NIH3T3 fibroblasts, Colloids Surf., B, 171, 501, 10.1016/j.colsurfb.2018.07.065 Rzemieniecki, 2019, Synthesis, properties, and antimicrobial activity of 1-alkyl-4-hydroxy-1-methylpiperidinium ionic liquids with mandelate anion, ACS Sustain. Chem. Eng., 7, 15053, 10.1021/acssuschemeng.9b03690 Santos de Almeida, 2017, Choline-versus imidazole-based ionic liquids as functional ingredients in topical delivery systems: Cytotoxicity, solubility, and skin permeation studies, Drug Dev. Ind. Pharm., 43, 1858, 10.1080/03639045.2017.1349788 Sarheed, 2020, Formation of stable nanoemulsions by ultrasound-assisted two-step emulsification process for topical drug delivery: Effect of oil phase composition and surfactant concentration and loratadine as ripening inhibitor, Int. J. Pharm., 576, 10.1016/j.ijpharm.2019.118952 Scalise, 2015, Microenvironment and microbiology of skin wounds: the role of bacterial biofilms and related factors, Seminars in Vasc. Surg. Elsevier, 151, 10.1053/j.semvascsurg.2016.01.003 Shamshina, 2014, Chitin–calcium alginate composite fibers for wound care dressings spun from ionic liquid solution, J. Mater. Chem. B, 2, 3924, 10.1039/C4TB00329B Shamshina, 2019, Advances in functional chitin materials: a review, ACS Sustain. Chem. Eng., 7, 6444, 10.1021/acssuschemeng.8b06372 Sidat, 2019, Ionic liquids as potential and synergistic permeation enhancers for transdermal drug delivery, Pharmaceutics, 11, 96, 10.3390/pharmaceutics11020096 Silva, 2012, The use of ionic liquids in the processing of chitosan/silk hydrogels for biomedical applications, Green Chem., 14, 1463, 10.1039/c2gc16535j Silva, 2017, Ionic liquids in the processing and chemical modification of chitin and chitosan for biomedical applications, Green Chem., 19, 1208, 10.1039/C6GC02827F Sintra, 2015, Enhancing the antioxidant characteristics of phenolic acids by their conversion into cholinium salts, ACS Sustain. Chem. Eng., 3, 2558, 10.1021/acssuschemeng.5b00751 Songkro, 2009, An overview of skin penetration enhancers: penetration enhancing activity, skin irritation potential and mechanism of action, Songklanakarin J. Sci. Technol., 31, 299 Takahashi, 2001, Characterization of the influence of polyol fatty acid esters on the permeation of diclofenac through rat skin, J. Control. Release, 73, 351, 10.1016/S0168-3659(01)00359-5 Tanner, 2018, Transdermal insulin delivery using choline-based ionic liquids (CAGE), J. Control. Release, 286, 137, 10.1016/j.jconrel.2018.07.029 Tanner, 2019, The influence of water on choline-based ionic liquids, ACS Biomater. Sci. Eng., 5, 3645, 10.1021/acsbiomaterials.9b00243 Tanner, 2020, Stabilization and Topical Skin Delivery of Framework Nucleic Acids using Ionic Liquids, Adv. Therap., 2000041 Tosato, M.G., Maya Girón, J. v, Martin, A.A., Krishna Tippavajhala, V., Fernández Lorenzo de Mele, M., Dicelio, L., 2018. Comparative study of transdermal drug delivery systems of resveratrol: High efficiency of deformable liposomes. Mater. Sci. Eng. C 90, 356–364. https://doi.org/https://doi.org/10.1016/j.msec.2018.04.073. Tran, 2016, Synthesis, structure and antimicrobial property of green composites from cellulose, wool, hair and chicken feather, Carbohydr. Polym., 151, 10.1016/j.carbpol.2016.06.021 Tsolou, 2020, Folate and Pegylated Aliphatic Polyester Nanoparticles for Targeted Anticancer Drug Delivery, Int. J. Nanomed., 15, 4899, 10.2147/IJN.S244712 Uddin, 2022, Transdermal Delivery of Antigenic Protein Using Ionic Liquid-Based Nanocarriers for Tumor Immunotherapy, ACS Applied Bio Materials, 5, 2586, 10.1021/acsabm.2c00061 van Gele, 2011, Three-dimensional skin models as tools for transdermal drug delivery: challenges and limitations, Expert Opinion on Drug Delivery, 8, 705, 10.1517/17425247.2011.568937 Waghule, 2019, Microneedles: A smart approach and increasing potential for transdermal drug delivery system, Biomed. Pharmacother., 109, 1249, 10.1016/j.biopha.2018.10.078 Wang, 2019, Design and Development of Lidocaine Microemulsions for Transdermal Delivery, AAPS PharmSciTech, 20, 63, 10.1208/s12249-018-1263-1 Wu, 2019, Improving dermal delivery of hydrophilic macromolecules by biocompatible ionic liquid based on choline and malic acid, Int. J. Pharm., 558, 380, 10.1016/j.ijpharm.2019.01.021 Wu, 2019, Improved transdermal permeability of ibuprofen by ionic liquid technology: Correlation between counterion structure and the physicochemical and biological properties, J. Mol. Liq., 283, 399, 10.1016/j.molliq.2019.03.046 Xu, 2017, Zinc ion coordinated poly (ionic liquid) antimicrobial membranes for wound healing, ACS Appl. Mater. Interfaces, 9, 14656, 10.1021/acsami.7b01677 Yang, 2021, Synergistic interactions of ionic liquids and antimicrobials improve drug efficacy, iScience, 24, 10.1016/j.isci.2020.101853 Yoshiura, 2013, Ionic liquid-in-oil microemulsions as potential carriers for the transdermal delivery of methotrexate, J. Chem. Eng. Jpn., 46, 794, 10.1252/jcej.13we009 Yu, J., Zhang, Y., Ye, Y., DiSanto, R., Sun, W., Ranson, D., Ligler, F.S., Buse, J.B., Gu, Z., 2015. Microneedle-array patches loaded with hypoxia-sensitive vesicles provide fast glucose-responsive insulin delivery. Proceedings of the National Academy of Sciences 112, 8260–8265. Yu, 2020, Multifunctional hydrogel based on ionic liquid with antibacterial performance, J. Mol. Liq., 299, 10.1016/j.molliq.2019.112185 Yuan, 2021, A cellulose/Konjac glucomannan–based macroporous antibacterial wound dressing with synergistic and complementary effects for accelerated wound healing, Cellulose, 28, 5591, 10.1007/s10570-021-03821-x Zakrewsky, 2016, Choline and geranate deep eutectic solvent as a broad- spectrum antiseptic agent for preventive and therapeutic applications, Adv. Healthcare Mater., 5, 1282, 10.1002/adhm.201600086 Zakrewsky, M., Lovejoy, K.S., Kern, T.L., Miller, T.E., Le, V., Nagy, A., Goumas, A.M., Iyer, R.S., del Sesto, R.E., Koppisch, A.T., 2014. Ionic liquids as a class of materials for transdermal delivery and pathogen neutralization. Proceedings of the National Academy of Sciences 111, 13313–13318. Zhang, 2017, Evaluations of imidazolium ionic liquids as novel skin permeation enhancers for drug transdermal delivery, Pharm. Dev. Technol., 22, 511, 10.3109/10837450.2015.1131718 Zheng, 2017, Metal-containing poly (ionic liquid) membranes for antibacterial applications, ACS Biomater. Sci. Eng., 3, 922, 10.1021/acsbiomaterials.7b00165 Zheng, 2020, Novel skin permeation enhancers based on amino acid ester ionic liquid: Design and permeation mechanism, Int. J. Pharm., 119031 Zhou, 2020, Development of aw/o emulsion using ionic liquid strategy for transdermal delivery of anti–aging component α–lipoic acid: Mechanism of different ionic liquids on skin retention and efficacy evaluation, Eur. J. Pharm. Sci., 141, 10.1016/j.ejps.2019.105042 Zhou, 2021, Self-healing, anti-freezing, adhesive and remoldable hydrogel sensor with ion-liquid metal dual conductivity for biomimetic skin, Compos. Sci. Technol., 203, 10.1016/j.compscitech.2020.108608