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Synthesis and Antimalarial Properties of Streptocyanine Dyes
Author(s) -
Maether MariePierre,
Desoubzdanne Denis,
Izquierdo Albert,
Guieu Valérie,
Maturano Marie,
AndréBarrès Christiane,
Valentin Alexis,
Jullian Valérie,
Chevalley Séverine,
Maynadier Marjorie,
Vial Henri,
Payrastre Corinne
Publication year - 2009
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200900051
Subject(s) - plasmodium falciparum , in vitro , chemistry , stereochemistry , combinatorial chemistry , biochemistry , biology , malaria , immunology
Several streptocyanine dyes were synthesized that contain polymethine chains of varying length. Their in vitro antimalarial activities were evaluated against the virulent P. falciparum parasite. In addition to the influence of polymethine chain length, the effects of structural modifications at nitrogen end groups, para substitution of the phenyl groups, and counter‐anions were studied. The most potent antimalarial activities were found for heptacarbon chain streptocyanines, with an IC 50 value of 60 n M . Interestingly, most of the compounds were less cytotoxic toward the mammalian cells tested. The best selective toxicity profiles were found for pentacarbon chain streptocyanines, which have a good in vitro specificity index.