Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Aromatic Selenocyanates as a New Class of Non-Mutagenic Antimicrobial Selenium Compounds with Pronounced Activity against Multidrug Resistant ESKAPE Bacteria

Muhammad Jawad Nasim
,
Karolina Witek
,
Annamaria Kincses
,
Muhammad Sarfraz
,
Ewa Żesławska
,
Małgorzata Anna Marć
,
Márió Gajdács
,
Gabriella Spengler
,
Wojciech Nitek
,
Gniewomir Latacz
,
Elżbieta Karczewska
,
Katarzyna Kieć-Kononowicz
,
Claus Jacob
* ,
Jadwiga Handzlik
*
Version 1 : Received: 21 February 2018 / Approved: 22 February 2018 / Online: 22 February 2018 (11:34:22 CET)

How to cite: Nasim, M.J.; Witek, K.; Kincses, A.; Sarfraz, M.; Żesławska, E.; Marć, M.A.; Gajdács, M.; Spengler, G.; Nitek, W.; Latacz, G.; Karczewska, E.; Kieć-Kononowicz, K.; Jacob, C.; Handzlik, J. Aromatic Selenocyanates as a New Class of Non-Mutagenic Antimicrobial Selenium Compounds with Pronounced Activity against Multidrug Resistant ESKAPE Bacteria. Preprints 2018, 2018020142. https://doi.org/10.20944/preprints201802.0142.v1 Nasim, M.J.; Witek, K.; Kincses, A.; Sarfraz, M.; Żesławska, E.; Marć, M.A.; Gajdács, M.; Spengler, G.; Nitek, W.; Latacz, G.; Karczewska, E.; Kieć-Kononowicz, K.; Jacob, C.; Handzlik, J. Aromatic Selenocyanates as a New Class of Non-Mutagenic Antimicrobial Selenium Compounds with Pronounced Activity against Multidrug Resistant ESKAPE Bacteria. Preprints 2018, 2018020142. https://doi.org/10.20944/preprints201802.0142.v1

Abstract

Selenocyanates form an interesting class of organic selenium compounds as they serve as multifunctional agents (being the precursors of seleninic acids and diselenides in synthetic chemistry and as antimicrobial and cytotoxic agent in biology) and, due to their similarity with better known thiocyanates promise high biological activity. Yet whilst selenocyanates are common in synthetic chemistry, they are rarely considered in pharmaceutical design. Arylmethyl selenocyanates (1-13) have been synthesized and an insight into their structural properties using X-ray crystallography has been obtained. The compounds subsequently have been evaluated for their potential antimicrobial, nematicidal and cytotoxic activity. ADMET properties in vitro, using mutagenicity (AMES) and permeability (PAMPA) tests, have been determined. The compounds exhibit pronounced activity against various strains of bacteria (both Gram-positive and Gram-negative) and yeasts. Among them, benzylselenocyanate (1) represents the most active anti-ESKAPE agent, with potent antibacterial activity, especially against multidrug resistant MRSA strains (HEMSA 5). Our results demonstrate that the arylmethyl selenocyantes are not only non-mutagenic but also possess moderate cytotoxic activity against cancer cells.

Keywords

reactive selenium species; arylmethyl selenocyanate; cellular thiolstat; antimicrobial; anticancer; ESKAPE; multidrug resistance

Subject

Chemistry and Materials Science, Medicinal Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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