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- Title
Synthesis, activity, and docking studies of eugenol‐based glucosides as new agents against Candida sp.
- Authors
Hipólito, Taciane Maíra Magalhães; Bastos, Guilherme Tadeu Lemos; Barbosa, Thúlio Wliandon Lemos; De Souza, Thiago Belarmino; Coelho, Luiz Felipe Leomil; Dias, Amanda Latércia Tranches; Rodríguez, Ihosvany Camps; Dos Santos, Marcelo Henrique; Dias, Danielle Ferreira; Franco, Lucas Lopardi; Carvalho, Diogo Teixeira
- 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 μ m), 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.
- Subjects
EUGENOL; GLUCOSIDES; ANTIFUNGAL agents; CANDIDIASIS treatment; CELL-mediated cytotoxicity; HYDROXYLATION; THERAPEUTICS
- Publication
Chemical Biology & Drug Design, 2018, Vol 92, Issue 2, p1514
- ISSN
1747-0277
- Publication type
Article
- DOI
10.1111/cbdd.13318