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Lycorine Derivatives Against Trichomonas vaginalis
Author(s) -
Giordani Raquel B.,
Junior Celso O. R.,
de Andrade Jean P.,
Bastida Jaume,
Zuanazzi Jose A. S.,
Tasca Tiana,
de Almeida Mauro V.
Publication year - 2012
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/j.1747-0285.2012.01333.x
Subject(s) - lycorine , trichomonas vaginalis , amaryllidaceae , antiparasitic , in vitro , chemistry , stereochemistry , alkaloid , mechanism of action , cell culture , pharmacology , biochemistry , microbiology and biotechnology , biology , medicine , botany , genetics , pathology
Six lycorine derivatives were prepared, characterized, and evaluated for their in vitro anti‐ Trichomonas vaginalis activity. Compounds bearing an acetyl ( 2 ), lauroyl ( 3 ), benzoyl ( 4 and 5 ), and p ‐nitrobenzoyl ( 6 and 7 ) groups were synthesized. The best activity was achieved with lycorine esterified at C‐2 position with lauroyl group. Preliminary structure–activity relationship points that unprotected OH group at C‐1 and C‐2 is not necessary to the antiparasitic activity, and none of the derivative was less active than lycorine. The lycorine structural requisites required to kill this amitochondriate cell seem to be different in comparison with the derivatives most active against other parasites and tumor cell lines, both mitochondriated cells. This result is an important contribution with our ongoing studies regarding the mechanism of action of the Amaryllidaceae alkaloids on T. vaginalis cell death opening a new perspective to optimize this innovative pharmacological potential.