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Article

Antimicrobial Properties and Cytotoxic Effect of Imidazolium Geminis with Tunable Hydrophobicity

by
Syumbelya K. Amerkhanova
1,
Alexandra D. Voloshina
1,
Alla B. Mirgorodskaya
1,
Anna P. Lyubina
1,
Darya A. Kuznetsova
1,
Rushana A. Kushnazarova
1,
Vasilii A. Mikhailov
2 and
Lucia Ya. Zakharova
1,*
1
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov st., 420088 Kazan, Russia
2
L.M. Litvinenko Institute of Physical Organic Chemistry and Coal Chemistry, R. Luxemburg st., 70, 83114 Donetsk, Ukraine
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2021, 22(23), 13148; https://doi.org/10.3390/ijms222313148
Submission received: 19 November 2021 / Revised: 29 November 2021 / Accepted: 2 December 2021 / Published: 5 December 2021
(This article belongs to the Special Issue The Self-Assembly and Design of Polyfunctional Nanosystems 3.0)
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Abstract

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.
Keywords: dicationic imidazolium surfactants; antimicrobial activity; cytotoxicity; hemolysis; antimicrobial resistance; selectivity dicationic imidazolium surfactants; antimicrobial activity; cytotoxicity; hemolysis; antimicrobial resistance; selectivity
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MDPI and ACS Style

Amerkhanova, S.K.; Voloshina, A.D.; Mirgorodskaya, A.B.; Lyubina, A.P.; Kuznetsova, D.A.; Kushnazarova, R.A.; Mikhailov, V.A.; Zakharova, L.Y. Antimicrobial Properties and Cytotoxic Effect of Imidazolium Geminis with Tunable Hydrophobicity. Int. J. Mol. Sci. 2021, 22, 13148. https://doi.org/10.3390/ijms222313148

AMA Style

Amerkhanova SK, Voloshina AD, Mirgorodskaya AB, Lyubina AP, Kuznetsova DA, Kushnazarova RA, Mikhailov VA, Zakharova LY. Antimicrobial Properties and Cytotoxic Effect of Imidazolium Geminis with Tunable Hydrophobicity. International Journal of Molecular Sciences. 2021; 22(23):13148. https://doi.org/10.3390/ijms222313148

Chicago/Turabian Style

Amerkhanova, Syumbelya K., Alexandra D. Voloshina, Alla B. Mirgorodskaya, Anna P. Lyubina, Darya A. Kuznetsova, Rushana A. Kushnazarova, Vasilii A. Mikhailov, and Lucia Ya. Zakharova. 2021. "Antimicrobial Properties and Cytotoxic Effect of Imidazolium Geminis with Tunable Hydrophobicity" International Journal of Molecular Sciences 22, no. 23: 13148. https://doi.org/10.3390/ijms222313148

APA Style

Amerkhanova, S. K., Voloshina, A. D., Mirgorodskaya, A. B., Lyubina, A. P., Kuznetsova, D. A., Kushnazarova, R. A., Mikhailov, V. A., & Zakharova, L. Y. (2021). Antimicrobial Properties and Cytotoxic Effect of Imidazolium Geminis with Tunable Hydrophobicity. International Journal of Molecular Sciences, 22(23), 13148. https://doi.org/10.3390/ijms222313148

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