title: Synthesis of ferroquine enantiomers: first investigation of effects of metallocenic chirality upon antimalarial activity and cytotoxicity.
abstract: Ferroquine (FQ) is a new antimalarial agent with a high blood schizotoncidal activity. Previous studies on this compound were done with racemate mixtures. As FQ possesses planar chirality, pure enantiomers were obtained by enzymatic resolution in order to compare their antimalarial activities and cytotoxicities. (+)-FQ and (-)-FQ were equally active in vitro, at nanomolar concentrations. Both enantiomers were slightly less active than the racemate in vivo; cytotoxicities were similar. Actually, the racemate represents the optimal formulation. To the best of our knowledge, this is the first investigation of biological activities of compounds with metallocenic chirality.
authors: INSERM U 42, 369 rue Jules Guesde BP 39, 59651 Villeneuve d'Ascq Cedex, France. laurence.delhaes@pasteur-lille.fr
authors: Laurence
authors: L
authors: Delhaes
authors: Christophe
authors: C
authors: Biot
authors: Laurence
authors: L
authors: Berry
authors: Philippe
authors: P
authors: Delcourt
authors: Lucien A
authors: LA
authors: Maciejewski
authors: Daniel
authors: D
authors: Camus
authors: Jacques S
authors: JS
authors: Brocard
authors: Daniel
authors: D
authors: Dive
mesh_terms: D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D002455:Cell Division / Q000187:drug effects; D002738:Chloroquine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D005260:Female; D005290:Ferric Compounds / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D066298:In Vitro Techniques; D008288:Malaria / Q000188:drug therapy; D051379:Mice; D010963:Plasmodium falciparum / Q000187:drug effects*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: C111773:7-chloro-4-((2-(N,N-dimethylaminomethyl))-N-methylferrocenylamino)quinoline; D000962:Antimalarials; D005290:Ferric Compounds; D002738:Chloroquine