Antimicrobial and Cytotoxic Activity of Novel Imidazolium-Based Ionic Liquids

Abstract

In this study, a series of 10 novel 1-methyl-3-octyloxymethylimidazolium derivatives carrying various anionic moieties (4-hydroxybenzenesulfonate, benzenesulfonate, carvacroloxyacetate, chloride, formate, propionate, thymoloxyacetate, vanillinoxyacetate, eugenoloxyacetate and trimethylacetate) were synthesized. Compounds were tested for their antimicrobial activity against six microbe strains (Staph-ylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli, Enterococcus faecalis, and Candida albicans), cytotoxic activity against the mouse melanoma cell line (B16 F10), and surface active properties. All synthesized compounds exhibited antimicrobial activity (expressed as minimum inhibitory concentration; in range of 0.10–27.82 mM/L), especially against Gram-positive bacteria and fungi. In addition, all compounds demonstrated cytotoxicity on B16 F10 cells (IC50 values 0.0101–0.0197 mM/L). Surface properties defined as CMC values, ranged from 0.72 to 32.35 mmol L-1. The obtained results provide an insight into the promising activity of a novel group of quaternary imidazolium derivatives having ionic liquid properties. The most potent compounds, containing a thymoloxyacetate and eugenoloxyacetate moiety, could be candidates for new antimicrobial agents or surfactants.

New Potential Agents for Malignant Melanoma Treatment—Most Recent Studies 2020–2022

“…Pałkowski et al obtained novel 1-methyl 3-octyloxymethylimidazolium derivatives carrying various anionic moieties [ 141 ]. The basis for the syntheses were the few scientific reports on the anticancer activity of ionic liquids [ 142 , 143 ].…”

“…Compound (57) exhibited the most promising activity against melanoma cell line B16F10 with IC 50 = 1.01 × 10 −2 µM/L. The most active derivative bore the thymoloxyacetic anion [ 141 ].…”

Surface-Active Ionic Liquids and Surface-Active Quaternary Ammonium Salts from Synthesis, Characterization to Antimicrobial Properties

“…It is noteworthy that, due to the ability to design the structure of multifunctional surface-active compounds, there has been a significant increase in interest in these compounds, especially owing to their use as antimicrobials [ 19 , 20 , 21 , 22 , 23 ]. For example, Shaheen et al [ 22 ] described SAILs in the context of their antimicrobial activity, similar to their quaternary ammonium counterparts.…”

“…For example, Shaheen et al [ 22 ] described SAILs in the context of their antimicrobial activity, similar to their quaternary ammonium counterparts. Also, in our recent works, we discussed the role of imidazolium SAILs with high surface activity as a potential tool for destroying microbes [ 5 , 19 ]. Another important use of SAILs and surface-active QASs focuses on sectors such as agriculture.…”

Rhodobacter sphaeroides as a model to study the ecotoxicity of 1-alkyl-3-methylimidazolium bromide

“…Previous investigations mainly focused on the relationship between the chemical structure of ILs and their toxicity. Studies have indicated that the inhibition of bacterial growth by ILs is due to their affinity and disruptive effect of ILs on the cell membrane and cell wall ( Docherty and Kulpa, 2005 ; Cornmell et al, 2008 ; Busetti et al, 2010 ; Ventura et al, 2013 ; Ghanem et al, 2015 ; Zheng et al, 2016 ; Cook et al, 2019 ; Pałkowski et al, 2022 ). The cationic structure of ILs is key to their toxicity because it allows ILs to be easily adsorbed and enriched in the negatively charged cell walls of bacteria.…”