A1 Journal article (refereed)
Binding motif of ebselen in solution : chalcogen and hydrogen bonds team up (2020)

Daolio, A., Scilabra, P., Di Pietro, M. E., Resnati, C., Rissanen, K., & Resnati, G. (2020). Binding motif of ebselen in solution : chalcogen and hydrogen bonds team up. New Journal of Chemistry, 44(47), 20697-20703. https://doi.org/10.1039/d0nj04647g

JYU authors or editors

Publication details

All authors or editors: Daolio, Andrea; Scilabra, Patrick; Di Pietro, Maria Enrica; Resnati, Chiara; Rissanen, Kari; Resnati, Giuseppe

Journal or series: New Journal of Chemistry

ISSN: 1144-0546

eISSN: 1369-9261

Publication year: 2020

Publication date: 21/12/2020

Volume: 44

Issue number: 47

Pages range: 20697-20703

Publisher: Royal Society of Chemistry

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/d0nj04647g

Publication open access: Not open

Publication channel open access: 

Abstract

Ebselen (2-phenyl-1,2-benzoselenazol-3(2H)one), a glutathione peroxidase mimic, is active against several RNA viruses, among others the retrovirus responsible for the COVID-19 pandemic. In this paper Se-77 and H-1 NMR studies of ebselen are reported and they identify the chalcogen bond (ChB) and hydrogen bond (HB) that are central in the landscape of interactions formed by the compound in solution. The selenium atom and the hydrogen atom at the C7 carbon act as ChB and HB donors and the O and N atoms of neutral molecules function as acceptors. The ChB and HB give rise to a bifurcated supramolecular synthon, which fastens the interaction acceptor opposite to the N-Se covalent bond of the selenazole ring. It is known that the biologically important reaction of ebselen with cysteine thiol groups is favoured when selenium acts as a chalcogen bond donor.

Keywords: organic compounds; amino acids; selenium; chemical bonds; antimicrobial compounds; viruses

Free keywords: amino acids; atoms; Selenium; Selenium compounds; viruses

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2020

JUFO rating: 1