Synthesis of three classes of rhodacyanine dyes and evaluation of their in vitro and in vivo antimalarial activity

Selected members of three classes of rhodacyanine dyes, [0, 0]-, [1, 0]-, and [0, 0, 0]-rhodacyanines, were synthesized and their in vitro antimalarial activities against Plasmodium falciparum K1 (chloroquine-resistant strain) as well as their in vivo activities against P. berghei in mice were deter...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2006-12, Vol.14 (24), p.8550-8563
Main Authors: Pudhom, Khanitha, Kasai, Kazuki, Terauchi, Hiroki, Inoue, Hiroshi, Kaiser, Marcel, Brun, Reto, Ihara, Masataka, Takasu, Kiyosei
Format: Article
Language:English
Subjects:
Animals
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antimalarials - chemical synthesis
Antimalarials - pharmacology
Antiparasitic agents
Biological and medical sciences
Cells, Cultured
Chloroquine - adverse effects
Coloring Agents - chemical synthesis
Coloring Agents - pharmacology
DLC hypothesis
Drug Resistance
Malaria
Malaria, Falciparum - drug therapy
Malaria, Falciparum - parasitology
Male
Medical sciences
Mice
Mice, Inbred ICR
Myoblasts, Skeletal - drug effects
Pharmacology. Drug treatments
Plasmodium berghei - drug effects
Plasmodium falciparum
Plasmodium falciparum - drug effects
Pyridinium Compounds - chemical synthesis
Pyridinium Compounds - pharmacology
Rats
Rhodacyanines
Thiazoles - chemical synthesis
Thiazoles - pharmacology
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Summary:Selected members of three classes of rhodacyanine dyes, [0, 0]-, [1, 0]-, and [0, 0, 0]-rhodacyanines, were synthesized and their in vitro antimalarial activities against Plasmodium falciparum K1 (chloroquine-resistant strain) as well as their in vivo activities against P. berghei in mice were determined. The novel [0, 0, 0]-rhodacynines, 3e and 3h, possessing a benzothiazole moiety, were shown to have highly promising antimalarial activities in vivo. Moreover, the [0, 0, 0]-rhodacyanines were found to be orally bioavailable.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2006.08.035