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Thio- and selenosemicarbazones as antiprotozoal agents against Trypanosoma cruzi and Trichomonas vaginalis

Authors :
Alexandra Ibáñez-Escribano
Cristina Fonseca-Berzal
Mónica Martínez-Montiel
Manuel Álvarez-Márquez
María Gómez-Núñez
Manuel Lacueva-Arnedo
Teresa Espinosa-Buitrago
Tania Martín-Pérez
José Antonio Escario
Penélope Merino-Montiel
Sara Montiel-Smith
Alicia Gómez-Barrio
Óscar López
José G. Fernández-Bolaños
Source :
Journal of Enzyme Inhibition and Medicinal Chemistry, Vol 37, Iss 1, Pp 781-791 (2022)
Publication Year :
2022
Publisher :
Taylor & Francis Group, 2022.

Abstract

Herein, we report the preparation of a panel of Schiff bases analogues as antiprotozoal agents by modification of the stereoelectronic effects of the substituents on N-1 and N-4 and the nature of the chalcogen atom (S, Se). These compounds were evaluated towards Trypanosoma cruzi and Trichomonas vaginalis. Thiosemicarbazide 31 showed the best trypanocidal profile (epimastigotes), similar to benznidazole (BZ): IC50 (31)=28.72 μM (CL-B5 strain) and 33.65 μM (Y strain), IC50 (BZ)=25.31 μM (CL-B5) and 22.73 μM (Y); it lacked toxicity over mammalian cells (CC50 > 256 µM). Thiosemicarbazones 49, 51 and 63 showed remarkable trichomonacidal effects (IC50 =16.39, 14.84 and 14.89 µM) and no unspecific cytotoxicity towards Vero cells (CC50 ≥ 275 µM). Selenoisosters 74 and 75 presented a slightly enhanced activity (IC50=11.10 and 11.02 µM, respectively). Hydrogenosome membrane potential and structural changes were analysed to get more insight into the trichomonacidal mechanism.

Details

Language :
English
ISSN :
14756366 and 14756374
Volume :
37
Issue :
1
Database :
Directory of Open Access Journals
Journal :
Journal of Enzyme Inhibition and Medicinal Chemistry
Publication Type :
Academic Journal
Accession number :
edsdoj.2e3a62e95f4841cdadefb7f108d1beea
Document Type :
article
Full Text :
https://doi.org/10.1080/14756366.2022.2041629