Chalcogen Bonding (ChB) as a Robust Supramolecular Recognition Motif of Benzisothiazolinone Antibacterials.

Autor: Pizzi A; Laboratory of Nanostructured Fluorinated Materials (NFMLab), Dept. Chemistry, Materials and Chemical Engineering 'Giulio Natta', Politecnico di Milano, Via Luigi Mancinelli, 7, I-20131, Milan, Italy., Daolio A; Laboratory of Nanostructured Fluorinated Materials (NFMLab), Dept. Chemistry, Materials and Chemical Engineering 'Giulio Natta', Politecnico di Milano, Via Luigi Mancinelli, 7, I-20131, Milan, Italy., Beccaria R; Laboratory of Nanostructured Fluorinated Materials (NFMLab), Dept. Chemistry, Materials and Chemical Engineering 'Giulio Natta', Politecnico di Milano, Via Luigi Mancinelli, 7, I-20131, Milan, Italy., Demitri N; Elettra - Sincrotrone Trieste, S.S. 14 Km 163.5 in Area Science Park, 34149, Basovizza, Trieste, Italy., Viani F; Istituto di Scienze e Tecnologie Chimiche 'Giulio Natta', C.N.R., Via Mario Bianco 9, 20131, Milano, Italy., Resnati G; Laboratory of Nanostructured Fluorinated Materials (NFMLab), Dept. Chemistry, Materials and Chemical Engineering 'Giulio Natta', Politecnico di Milano, Via Luigi Mancinelli, 7, I-20131, Milan, Italy.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Jun 07; Vol. 29 (32), pp. e202300571. Date of Electronic Publication: 2023 Apr 25.
DOI: 10.1002/chem.202300571
Abstrakt: 1,2-benzisothiazol-3(2H)-one derivatives are highly active against a broad spectrum of fungi as well as Gram positive and Gram negative bacteria. For this reason they are extensively used, for example, as additives in detergents, leather products, paper coatings, and antifouling paintings. In this paper experimental findings are reported proving that the sulfur atom of benzisothiazolinones have a remarkable tendency to form short and directional chalcogen bondings on the extension of the covalent N-S bond and, to a lesser extent, of the C-S bond. Analyses of the Cambridge Structural Database confirm the interaction as a primary recognition motif of these systems. The electrophilicity of sulfur is crucial in the chemical reactions initiating the cascade of events resulting in the biopharmacological activities of benzisothiazolinones. The reported results suggest that the electrophility of sulfur may play a role also at earlier stages than the reactive ones, namely it may pin the compounds at the active site of target enzymes via chalcogen bondings that preorganize the system in the conformation required for the bonds formation/cleavage determining the biopharmacological activity.
(© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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