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Title: Glucosyl-1,2,3-triazoles derived from eugenol and analogues : synthesis, anti-Candida activity, and molecular modeling studies in CYP-51.
Authors: Magalhães, Lorena Severiano de
Reis, Adriana Cotta Cardoso
Nakao, Izadora Amaral
Péret, Vinícius Augusto Campos
Reis, Rúbia Castro Fernandes Melo
Silva, Naiara Chaves
Dias, Amanda Latércia Tranches
Carvalho, Diogo Teixeira
Dias, Danielle Ferreira
Brandão, Geraldo Célio
Braga, Saulo Fehelberg Pinto
Souza, Thiago Belarmino de
Keywords: Molecular docking
Molecular dynamics
Issue Date: 2021
Citation: MAGALHÃES, L. S. de et al. Glucosyl-1,2,3-triazoles derived from eugenol and analogues: synthesis, anti-Candida activity, and molecular modeling studies in CYP-51. Chemical Biology & Drug Design, v. 98, p. 903-913, 2021. Disponível em: <>. Acesso em: 11 out. 2022.
Abstract: This work describes the synthesis, anti-Candida, and molecular modeling stud- ies of eighteen new glucosyl-1,2,3-triazoles derived from eugenol and corre- lated phenols. The new compounds were characterized by combined Fourier Transform Infrared, 1 H and 13C nuclear magnetic resonance and spectroscopy of high-resolution mass spectrometry. The synthesized compounds did not show significant cytotoxicity against healthy fibroblast human cells (MCR-5) providing interesting selectivity indexes (SI) to active compounds. Considering the antifun- gal activity, nine compounds showed anti-Candida potential and the peracety- lated triazoles 17 and 18 were the most promising ones. Eugenol derivative 17 was active against three species of Candida at 26.1–52.1 μM. This compound was four times more potent than fluconazole against Candida krusei and less toxic (SI > 6.6) against the MCR-5 cells than fluconazole (SI > 3.3) considering this strain. Dihydroeugenol derivative 18 showed similar activity to 17 and was four times more potent and less toxic than fluconazole against C. krusei. The deacety- lated glucosides and non-glucosylated corresponding derivatives did not show considerable antifungal action, suggesting that the acetyl groups are essential for their anti-Candida activity. Molecular docking coupled with molecular dynam- ics showed that 14α-lanosterol demethylase is a feasible molecular target, since 17 and 18 could bind to this enzyme once deacetylated in vivo, thereby acting as prodrugs. Also, these studies demonstrated the importance of hydrophobic sub- stituents at the phenyl ring.
ISSN: 1747-0285
Appears in Collections:DEFAR - Artigos publicados em periódicos

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