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 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.
Pudhom
Khanitha
K
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Kasai
Kazuki
K
Terauchi
Hiroki
H
Inoue
Hiroshi
H
Kaiser
Marcel
M
Brun
Reto
R
Ihara
Masataka
M
Takasu
Kiyosei
K
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology; D002478:Cells, Cultured; D002738:Chloroquine / Q000009:adverse effects; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004351:Drug Resistance; D016778:Malaria, Falciparum / Q000188:drug therapy* / Q000469:parasitology; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D032448:Myoblasts, Skeletal / Q000187:drug effects; D010962:Plasmodium berghei / Q000187:drug effects*; D010963:Plasmodium falciparum / Q000187:drug effects*; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D000962:Antimalarials; D004396:Coloring Agents; D011726:Pyridinium Compounds; D013844:Thiazoles; C481079:rhodacyanine; D002738:Chloroquine