Synthesis and Antimalarial Properties of Streptocyanine Dyes

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 nitr...

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Published in:ChemMedChem 2009-08, Vol.4 (8), p.1327-1332
Main Authors: Maether, Marie-Pierre, Desoubzdanne, Denis, Izquierdo, Albert, Guieu, Valérie, Maturano, Marie, André-Barrès, Christiane, Valentin, Alexis, Jullian, Valérie, Chevalley, Séverine, Maynadier, Marjorie, Vial, Henri, Payrastre, Corinne
Format: Article
Language:English
Subjects:
Animals
Antimalarials - chemical synthesis
Antimalarials - chemistry
Antimalarials - toxicity
antiprotozoal agents
Carbocyanines - chemistry
Cell Line, Tumor
cyanine
cytotoxicity
Humans
malaria
Mice
Plasmodium falciparum
Plasmodium falciparum - drug effects
Structure-Activity Relationship
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Summary: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 IC50 value of 60 nM. 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. The synthesis, cytotoxicity, and antimalarial activity of three series of streptocyanine dyes are reported herein. In addition to the influence of the length of the polymethine chain (n=1, 2), we studied the effects of other structural modifications (nitrogen end groups R1 and R2, the para substituent of the phenyl groups R, and counter‐anions Q).
ISSN:1860-7179
1860-7187
DOI:10.1002/cmdc.200900051