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Title: Synthesis, activity, and docking studies of eugenol-based glucosides as new agents against Candida sp.
Authors: Hipolito, Taciane Maira Magalhães
Bastos, Guilherme Tadeu Lemos
Barbosa, Thulio Wliandon Lemos
Souza, Thiago Belarmino de
Coelho, Luiz Felipe Leomil
Dias, Amanda Latercia Tranches
Rodríguez, Ihosvany Camps
Santos, Marcelo Henrique dos
Dias, Danielle Ferreira
Franco, Lucas Lopardi
Carvalho, Diogo Teixeira
Keywords: Antifungals
Molecular docking
Issue Date: 2018
Citation: HIPOLITO, T. M. M. et al. Synthesis, activity, and docking studies of eugenol-based glucosides as new agents against Candida sp. Chemical Biology & Drug Design, v. 92, n. 2, p. 1514-1524, ago. 2018. Disponível em: <>. Acesso em: 7 mar. 2019.
Abstract: Seventeen new synthetic derivatives of eugenol (6, 8–15 and 8′‐15′) were planned following literature reports on antifungal activities of nitroeugenol and eugenol glucoside. The anti‐Candida activity of these compounds was investigated by in vitro assay, and the cytotoxicity evaluation was performed with the most active compounds. The peracetylated glucosides presented better biological results than their hydroxylated analogues. The glucoside 11, a 4‐nitrobenzamide, showed the best potency (MIC50 range 11.0–151.84 μm), the wider spectrum of action, and overall the best selectivity indexes, especially against C. tropicalis (~30) and C. krusei (~15). To investigate its possible mechanism of action, glucoside 11 was subjected to molecular docking studies with Candida sp. enzymes involved in ergosterol biosynthesis. Results have shown that the peracetyl glucosyl moiety and the 4‐nitrobenzamide group in 11 are effectively involved in its high affinity with the active site of squalene epoxidase.
ISSN: 1747-0285
Appears in Collections:DEFAR - Artigos publicados em periódicos

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