Alkylation of heme by the antimalarial drug artemisinin.
The peroxide function of artemisinin has been activated by iron(II)-heme generated in situ from iron(III)-protoporphyrin-IX and glutathione, a biologically relevant reductant. In mild conditions, this reaction produced a high yield (85%) of heme derivatives alkylated at alpha-, beta-, and delta-meso positions by a C4-centered radical derived from artemisinin.
Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne 31077 Toulouse, France.
Anne
A
Robert
Yannick
Y
Coppel
Bernard
B
Meunier
D000478:Alkylation; D000962:Antimalarials / Q000737:chemistry*; D037621:Artemisinins / Q000737:chemistry*; D005978:Glutathione / Q000737:chemistry; D006418:Heme / Q000737:chemistry*; D010084:Oxidation-Reduction; D011524:Protoporphyrins / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry*
D000962:Antimalarials; D037621:Artemisinins; D011524:Protoporphyrins; D012717:Sesquiterpenes; C448299:iron protoporphyrin IX; D006418:Heme; C031327:artemisinin; D005978:Glutathione