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 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 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.
Maether
Marie-Pierre
MP
Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique, UMR 5068, Université de Toulouse, 31062 Toulouse Cedex 9, France.
Desoubzdanne
Denis
D
Izquierdo
Albert
A
Guieu
Valérie
V
Maturano
Marie
M
André-Barrès
Christiane
C
Valentin
Alexis
A
Jullian
Valérie
V
Chevalley
Séverine
S
Maynadier
Marjorie
M
Vial
Henri
H
Payrastre
Corinne
C
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D002232:Carbocyanines / Q000737:chemistry*; D045744:Cell Line, Tumor; D006801:Humans; D051379:Mice; D010963:Plasmodium falciparum / Q000187:drug effects; D013329:Structure-Activity Relationship
D000962:Antimalarials; D002232:Carbocyanines