To Cut the Mustard: Antimicrobial Activity of Selenocyanates on the Plate and in the Gas Phase

Muhammad Sarfraz; Muhammad Jawad Nasim; Martin C H Gruhlke; Jadwiga Handzlik; Claus Jacob

doi:10.3390/antibiotics12020290

To Cut the Mustard: Antimicrobial Activity of Selenocyanates on the Plate and in the Gas Phase

Antibiotics (Basel). 2023 Feb 1;12(2):290. doi: 10.3390/antibiotics12020290.

Authors

Muhammad Sarfraz^{1

2}, Muhammad Jawad Nasim², Martin C H Gruhlke¹, Jadwiga Handzlik³, Claus Jacob²

Affiliations

¹ Department of Plant Physiology, RWTH Aachen University, Worringer Weg 1, 52056 Aachen, Germany.
² Division of Bioorganic Chemistry, Saarland University, Campus B2 1, 66123 Saarbruecken, Germany.
³ Department of Technology and Biotechnology of Drugs, Faculty of Pharmacy, Jagiellonian University Medical College in Kraków, Medyczna 9, 30-688 Cracow, Poland.

Abstract

Organic selenocyanates (RSeCN) are among the most reactive and biologically active Se species, often exhibiting a pronounced cytotoxic activity against mammalian cells and microorganisms. Various aromatic selenocyanates have been synthesized and, similar to some of the most Reactive Sulfur Species (RSS), such as allicin, found to be active against a range of bacteria, including Escherichia coli, Pseudomonas syringae and Micrococcus luteus, and fungi, including Verticillium dahlia, Verticillium longisporum, Alternaria brassicicola, and Botrytis cinerea, even via the gas phase. The highest antimicrobial activity has been observed for benzyl selenocyanate, which inhibited the growth of all bacteria considerably, even at the lowest tested concentration of 50 µM. Notably, neither the analogues thiocyanate (BTC) nor isothiocyanate (BITC) show any of these activities, rendering this selenium motif rather special in activity and mode of action. Eventually, these findings advocate a range of potential applications of organic selenocyanates in medicine and agriculture.

Keywords: (iso-)thiocyanates; gas phase activity; microbiological assays; selenocyanates.

Grants and funding

The authors acknowledge the financial support provided by Landgard Stiftung and Deutscher Akademischer Austauschdienst (DAAD) Scholarship Scheme (57202887). The authors also acknowledge the financial support provided by the University of Saarland, Saarbruecken, Germany and RWTH Aachen University, Aachen, Germany.