Antiproliferative and Antimicrobial Effects of Tris(2-hydroxyethyl)ammonium-Based Protic Ionic Liquids with Some Fatty Acids

Year 2020, Volume: 10 Issue: 3, 2021 - 2027, 01.09.2020

Hüseyin Akbaş , Aslı Yıldırım , Şeyma Menevşe , Nazan Gökşen

https://doi.org/10.21597/jist.695018

Cited By: 2

Abstract

Protic ionic liquids (PILs) that emerge as promising compounds are of great interest in industry and academia due to their easy synthesis and unique physical and chemical properties. This study aims to evaluate the antimicrobial activities against various microorganisms and the antiproliferative effects of four PILs namely, the PILs tris(2-hydroxyethyl)ammonium dodecanoate (TALA), tris(2-hydroxyethyl)ammonium tetradecanoate (TAMA), tris(2-hydroxyethyl)ammonium palmitate (TAPA) and tris(2-hydroxyethyl)ammonium stearate (TASA). Antiproliferative effects of PILs were investigated in vitro on breast cancer cell line (MDA-MB 231), colon cancer cell line (HT29) and prostate cancer cell line (PC3). Furthermore, minimum inhibitory concentrations (MIC) were established for PILs tested against rods, cocci and fungi. The antimicrobial activities of the PILs are strongly related to the alkyl chain length of the anion.

Keywords

Antibacterial effect, Antiproliferative effect, Protic ionic liquids

References

• Akbaş H., 2020. Synthesis and spectroscopic characterization of protic tris (2-Hydroxyethyl)-ammonium ionic liquids. JOTSCA, 7: 19-24.
• Earle MJ and Seddon KR, 2000. Ionic liquids. Green solvents for the future. Pure Appl Chem, 72: 1391-1398.
• Egorova KS and Ananikov VP, 2018. Fundamental importance of ionic interactions in the liquid phase: A review of recent studies of ionic liquids in biomedical and pharmaceutical applications. J Mol Liq, 272: 271-300
• Egorova KS, Gordeev EG and Ananikov VP, 2017. Biological activity of ionic liquids and their application in pharmaceutics and medicine. Chem Rev, 117: 7132-7189.
• El Bourakadi K, Merghoub N, Hicham G, El MehdiMekhzoum M, Essassi EM, Qaiss A and Bouhfid R, 2019. Synthesis, characterization and in vitro antiproliferative evaluation of ionic liquids based on alkyl-substituted thiabendazolium. J Mol Liq, 282: 63-69.
• Erden Tayhan S, Bilgin S and Elmastaş M, 2018. Evaluation of the wound healing potential of Teucrioside. Int J Chem Tech, 2: 16-19.
• Ferraz R, Costa-Rodrigues J, Fernandes MH, Santos MM, Marrucho IM, Rebelo LPN, Prudêncio C, Noronha JP, Petrovski Z and Branco LC, 2015. Antitumor activity of ionic liquids based on ampicillin. ChemMedChem., 10: 1480-1483.
• Freemantle M, 2009. An introduction to ionic liquids. The Royal Society of Chemistry, Cambridge, UK.
• Frizzo CP, Gindri IM, Tier AZ, Buriol L, Moreira DN and Martins MAP, 2013. Pharmaceutical salts: solids to liquids by using ionic liquid design. Ionic Liquids-New Aspects for the Future. IntechOpen.
• Garcia MT, Ribosa I, Perez L, Manresa A and Comelles F, 2013. Aggregation behavior and antimicrobial activity of ester-functionalized imidazolium- and pyridinium-based ionic liquids in aqueous solution. Langmuir, 29: 2536-2545.
• Gökşen N, 2016. Antimicrobial activities of essential oils of Mentha pulegium, Ziziphora tenuior and Echinophora tenuifolia and its effect on biofilm. Gaziosmanpaşa University Graduate School of Natural and Applied Sciences, Master Thesis (Printed).
• Hough WL, Smiglak M, Rodrı´guez H, Swatloski RP, Spear SK, Daly DT, Pernak J, Grisel JE, Carliss RD, Soutullo MD, Davis JH and Rogers RD, 2007. The third evolution of ionic liquids: active pharmaceutical ingredients. New J Chem, 31: 1429-1436.
• İnan A, İkiz M, Erden Tayhan S, Bilgin S, Genç N, Sayın K, Ceyhan G, Köse M, Dağ A and İspir E, 2018. Antiproliferative, antioxidant, computational and electrochemical studies of new azo-containing Schiff base ruthenium complexes. New J Chem, 42: 2952-2963.
• İspir E, İkiz M, Inan A, Sünbül AB, Erden Tayhan S, Bilgin S, Köse M and Elmastaş M, 2019. Synthesis, structural characterization, electrochemical, photoluminescence, antiproliferative and antioxidant properties of Co(II), Cu(II) and Zn(II) complexes bearing the azo-azomethine ligands. J Mol Struct, 1182: 63-71.
• Kumar V and Malhotra SV, 2009. Study on the potential anti-cancer activity of phosphonium and ammonium-based ionic liquids. Bioorg Med Chem Lett, 19: 4643-4646.
• Malhotra SV and Kumar V, 2010. A profile of the in vitro anti-tumor activity of imidazolium-based ionic liquids. Bioorg Med Chem Lett, 20: 581-585.
• Pendleton JN and Gilmore BF, 2015. The antimicrobial potential of ionic liquids: A source of chemical diversity for infection and biofilm control. Int J Antimicrob Agents, 46: 131-139.
• Rezki N, Messali M, Al-Sodies SA, Naqvi A, Bardaweel SK, Al-blewi FF, Aouad MR and El Ashry ESH, 2018. Design, synthesis, in-silico and in-vitro evaluation of di-cationic pyridinium ionic liquids as potential anticancer scaffolds. J Mol Liq, 265: 428-441.
• Tawfik SM, 2015. Simple one step synthesis of gemini cationic surfactant-based ionic liquids: Physicochemical, surface properties and biological activity. J Mol Liq, 209: 320-326.
• Toledo Hijo AAC, Maximo GJ, Costa MC, Cunha RL, Pereira JFB, Kurnia KA, Batista EAC and Meirelles AJA, 2017. Phase behavior and physical properties of new biobased ionic liquid crystals. J Phys Chem B, 121: 3177-3189.
• Vekeriya RL, 2017. A review of ionic liquids: Applications towards catalytic organic transformations. J Mol Liq, 227: 44-60.