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Antimalarial acridines: synthesis, in vitro activity against P. falciparum and interaction with hematin.

Abstract：

:A series of acridine derivatives were synthesised and their in vitro antimalarial activity was evaluated against one chloroquine-susceptible strain (3D7) and three chloroquine-resistant strains (W2, Bre1 and FCR3) of Plasmodium falciparum. Structure-activity relationship showed that two positives charges as well as 6-chloro and 2-methoxy substituents on the acridine ring were required to exert a good antimalarial activity. The best compounds possessing these features inhibited the growth of the chloroquine-susceptible strain with an IC(50)0.07 microM, close to that of chloroquine itself, and that of the three chloroquine-resistant strains better than chloroquine with IC(50)0.3 microM. These acridine derivatives inhibited the formation of beta-hematin, suggesting that, like CQ, they act on the haem crystallization process. Finally, in vitro cytotoxicity was also evaluated upon human KB cells, which showed that one of them 9-(6-ammonioethylamino)-6-chloro-2-methoxyacridinium dichloride 1 displayed a promising antimalarial activity in vitro with a quite good selectivity index versus mammalian cell on the CQ-susceptible strain and promising selectivity on other strains.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Guetzoyan L,Yu XM,Ramiandrasoa F,Pethe S,Rogier C,Pradines B,Cresteil T,Perrée-Fauvet M,Mahy JP

doi

10.1016/j.bmc.2009.10.005

subject

Has Abstract

pub_date

2009-12-01 00:00:00

pages

8032-9

issue

23

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(09)00924-9

journal_volume

17

pub_type

杂志文章

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