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Open AccessArticle

Antimicrobial and Antifungal Activity of Rare Substituted 1,2,3-Thiaselenazoles and Corresponding Matched Pair 1,2,3-Dithiazoles

1
School of Pharmacy, Faculty of Health Sciences, University of Eastern Finland, 70211 Kuopio, Finland
2
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia
3
Nanotechnology Education and Research Center, South Ural State University, Lenina Ave. 76, 454080 Chelyabinsk, Russia
4
Department of Internal Medicine VIII, University Hospital Tübingen University of Tübingen, 72076 Tübingen, Germany
5
Department of Pharmacology, School of Medicine, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA
*
Author to whom correspondence should be addressed.
Antibiotics 2020, 9(7), 369; https://doi.org/10.3390/antibiotics9070369
Received: 7 June 2020 / Revised: 23 June 2020 / Accepted: 26 June 2020 / Published: 1 July 2020
We report our investigations into the underlying differences between 1,2,3-dithiazole and their ultra-rare counterpart, 1,2,3-thiaselenazole. This rare 1,2,3-thiaselenazole chemotype was afforded by sulfur extrusion and selenium insertion into the preconstructed 1,2,3-dithiazoles. We built a library of matched paired compounds to compare and contrast the two ring systems. This led to the development of both narrow and broad-spectrum antimicrobial compounds with sub-micro molar potency, limited to no toxicity and a further understanding of the transition state electronics through molecular simulations. We also identified the potent 4,5,6-trichlorocyclopenta[d][1,2,3]thiaselenazole 11a, for use against Candida albicans, Cryptococcus neoformans var. grubii, Staphylococcus aureus and Acinetobacter baumannii, all of which have limited clinical treatment options. The 1,2,3-thiaselenazole represents a new class of potential compounds for the treatment of a host of multi-resistant hospital derived infections. View Full-Text
Keywords: 1,2,3-dithiazole; 1,2,3-thiaselenazole; sulfur extrusion; selenium dioxide; antimicrobial; antibacterial; antifungal 1,2,3-dithiazole; 1,2,3-thiaselenazole; sulfur extrusion; selenium dioxide; antimicrobial; antibacterial; antifungal
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MDPI and ACS Style

Laitinen, T.; Baranovsky, I.V.; Konstantinova, L.S.; Poso, A.; Rakitin, O.A.; Asquith, C.R.M. Antimicrobial and Antifungal Activity of Rare Substituted 1,2,3-Thiaselenazoles and Corresponding Matched Pair 1,2,3-Dithiazoles. Antibiotics 2020, 9, 369.

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