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

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

Journal

Antibiotics-Basel
ISSN: 2079-6382

Output data

Year: 2020, Volume: 9, Number: 7, Article number : 369, Pages count : DOI: 10.3390/antibiotics9070369

Authors

Laitinen Tuomo ¹ , Baranovsky Ilia V. ² , Konstantinova Lidia S. ^2,3 , Poso Antti ^4,5 , Rakitin Oleg A. ^2,3 , Asquith Christopher R.M. ⁶

Affiliations

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	School of Pharmacy, Faculty of Health Sciences, University of Eastern Finland, 70211 Kuopio, Finland
6	Department of Pharmacology, School of Medicine, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA

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.

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-Basel. 2020. V.9. N7. 369 . DOI: 10.3390/antibiotics9070369 WOS Scopus OpenAlex

Web of science:	WOS:000557168200001
Scopus:	2-s2.0-85087415119
OpenAlex:	W3040568245

DB	Citing
OpenAlex	13
Scopus	13
Web of science	12