Selenoneine-inspired selenohydantoins with glutathione peroxidase-like activity.

Autor: Alhasan R; Université de Lorraine, CITHEFOR, F-54000 Nancy, France; Division of Bioorganic Chemistry, School of Pharmacy, Saarland University, 66123 Saarbruecken, Germany., Martins GM; Department of Chemistry, Federal University of Sao Carlos, UFSCar, 13565-905 São Carlos, SP, Brazil; Institute of Exact Sciences, Department of Chemistry, Federal University of Minas Gerais, UFMG, 31270-901 Belo Horizonte, MG, Brazil., de Castro PP; Department of Chemistry, Federal University of Sao Carlos, UFSCar, 13565-905 São Carlos, SP, Brazil., Saleem RSZ; Department of Chemistry and Chemical Engineering, SBA School of Sciences and Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan., Zaiter A; Université de Lorraine, LCP-A2MC, F-57000 Metz, France., Fries-Raeth I; Université de Lorraine, CITHEFOR, F-54000 Nancy, France., Kleinclauss A; Université de Lorraine, CITHEFOR, F-54000 Nancy, France., Perrin-Sarrado C; Université de Lorraine, CITHEFOR, F-54000 Nancy, France., Chaimbault P; Université de Lorraine, LCP-A2MC, F-57000 Metz, France., da Silva Júnior EN; Institute of Exact Sciences, Department of Chemistry, Federal University of Minas Gerais, UFMG, 31270-901 Belo Horizonte, MG, Brazil. Electronic address: eufranio@ufmg.br., Gaucher C; Université de Lorraine, CITHEFOR, F-54000 Nancy, France; Université de Lorraine, CNRS, IMoPA, F-54000 Nancy, France. Electronic address: caroline.gaucher@univ-lorraine.fr., Jacob C; Division of Bioorganic Chemistry, School of Pharmacy, Saarland University, 66123 Saarbruecken, Germany.
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry [Bioorg Med Chem] 2023 Oct 30; Vol. 94, pp. 117479. Date of Electronic Publication: 2023 Sep 20.
DOI: 10.1016/j.bmc.2023.117479
Abstrakt: Chronic diseases such as cystic fibrosis, inflammatory bowel diseases, rheumatoid arthritis, and cardiovascular illness have been linked to a decrease in selenium levels and an increase in oxidative stress. Selenium is an essential trace element that exhibits antioxidant properties, with selenocysteine enzymes like glutathione peroxidase being particularly effective at reducing peroxides. In this study, a series of synthetic organoselenium compounds were synthesized and evaluated for their potential antioxidant activities. The new selenohydantoin molecules were inspired by selenoneine and synthesized using straightforward methods. Their antioxidant potential was evaluated and proven using classical radical scavenging and metal-reducing methods. The selenohydantoin derivatives exhibited glutathione peroxidase-like activity, reducing hydroperoxides. Theoretical calculations using Density Functional Theory (DFT) revealed the selenone isomer to be the only one occurring in solution, with selenolate as a possible tautomeric form in the presence of a basic species. Cytocompatibility assays indicated that the selenohydantoin derivatives were non-toxic to primary human aortic smooth muscle cells, paving the way for further biological evaluations of their antioxidant activity. The results suggest that selenohydantoin derivatives with trifluoro-methyl (-CF 3 ) and chlorine (-Cl) substituents have significant activities and could be potential candidates for further biological trials. These compounds may contribute to the development of effective therapies for chronic diseases such cardiovascular diseases.
Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2023 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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