Department of Pharmaceutical Technology, Faculty of Pharmacy, Nicolaus Copernicus University, Jurasza 2, 85-089 Bydgoszcz, Poland.
Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, 60-965 Poznan, Poland.
Molecules. 2022 Mar 18;27(6):1974. doi: 10.3390/molecules27061974.
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.
在这项研究中，合成了一系列 10 种新型 1-甲基-3-辛基甲氧基甲基咪唑鎓衍生物，它们带有各种阴离子部分（对羟基苯磺酸酯、苯磺酸酯、香豆酸酯、氯化物、甲酸盐、丙酸盐、麝香草酚氧乙酸酯、香草醛氧乙酸酯、丁香酚氧乙酸酯和三甲基乙酸酯）。测试了这些化合物对六种微生物菌株（金黄色葡萄球菌、铜绿假单胞菌、肺炎克雷伯菌、大肠杆菌、粪肠球菌和白色念珠菌）的抗菌活性、对小鼠黑色素瘤细胞系（B16 F10）的细胞毒性活性以及表面活性性质。所有合成的化合物均表现出抗菌活性（以最小抑菌浓度表示；在 0.10-27.82 mM/L 范围内），尤其是对革兰氏阳性菌和真菌。此外，所有化合物在 B16 F10 细胞上均表现出细胞毒性（IC50 值为 0.0101-0.0197 mM/L）。表面性质定义为 CMC 值，范围从 0.72 到 32.35 mmol/L。所得结果为具有离子液体性质的新型季铵化咪唑鎓衍生物的有前途的活性提供了深入了解。含有麝香草酚氧乙酸酯和丁香酚氧乙酸酯部分的最有效化合物可能是新型抗菌剂或表面活性剂的候选物。
