title: Lycorine derivatives against Trichomonas vaginalis.
abstract: 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.
authors.affiliation: Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000 Porto Alegre, RS, Brazil.
authors.forename: Raquel B
authors.initials: RB
authors.lastname: Giordani
authors.forename: Celso O R
authors.initials: CO
authors.lastname: Junior
authors.forename: Jean P
authors.initials: JP
authors.lastname: de Andrade
authors.forename: Jaume
authors.initials: J
authors.lastname: Bastida
authors.forename: Jose A S
authors.initials: JA
authors.lastname: Zuanazzi
authors.forename: Tiana
authors.initials: T
authors.lastname: Tasca
authors.forename: Mauro V
authors.initials: MV
authors.lastname: de Almeida
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010617:Phenanthridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014246:Trichomonas vaginalis / Q000187:drug effects*
chemical_list: D047151:Amaryllidaceae Alkaloids; D000981:Antiprotozoal Agents; D010617:Phenanthridines; C015330:lycorine