Premium
Synthesis, activity, and docking studies of eugenol‐based glucosides as new agents against Candida sp.
Author(s) -
Hipólito Taciane Maíra Magalhães,
Bastos Guilherme Tadeu Lemos,
Barbosa Thúlio Wliandon Lemos,
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
Publication year - 2018
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.13318
Subject(s) - docking (animal) , eugenol , chemistry , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , medicine , veterinary medicine
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 ( MIC 50 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.