Antimicrobial Properties and Cytotoxic Effect of Imidazolium Geminis with Tunable Hydrophobicity.

Amerkhanova, Syumbelya K.; Voloshina, Alexandra D.; Mirgorodskaya, Alla B.; Lyubina, Anna P.; Kuznetsova, Darya A.; Kushnazarova, Rushana A.; Mikhailov, Vasilii A.; Zakharova, Lucia Ya.

Antimicrobial, membranotropic and cytotoxic properties of dicationic imidazolium surfactants of n-s-n (Im) series with variable length of alkyl group (n = 8, 10, 12, 14, 16) and spacer fragment (s = 2, 3, 4) were explored and compared with monocationic analogues. Their activity against a representative range of Gram-positive and Gram-negative bacteria, and also fungi, is characterized. The relationship between the biological activity and the structural features of these compounds is revealed, with the hydrophobicity emphasized as a key factor. Among dicationic surfactants, decyl derivatives showed highest antimicrobial effect, while for monocationic analogues, the maximum activity is observed in the case of tetradecyl tail. The leading compounds are 2–4 times higher in activity compared to reference antibiotics and prove effective against resistant strains. It has been shown that the antimicrobial effect is not associated with the destruction of the cell membrane, but is due to specific interactions of surfactants and cell components. Importantly, they show strong selectivity for microorganism cells while being of low harm to healthy human cells, with a SI ranging from 30 to 100.

ALKYL group; GRAM-positive bacteria; GRAM-negative bacteria; SURFACE active agents; CELL anatomy

International Journal of Molecular Sciences, 2021, Vol 22, Issue 23, p13148

1661-6596

Academic Journal

10.3390/ijms222313148