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Title: Elucidation of the natural artemisinin decomposition route upon iron interaction: A fine electronic redistribution promotes reactivity
Authors: Wichit Nosoongnoen
Jaturong Pratuangdejkul
Korbtham Sathirakul
Alexandre Jacob
Marc Conti
Sylvain Loric
Jean Marie Launay
Philippe Manivet
Hopital Lariboisiere AP-HP
Universite Paris Descartes
Mahidol University
Hopital de Bicetre
Hopital Henri Mondor
Keywords: Chemistry;Physics and Astronomy
Issue Date: 22-Aug-2008
Citation: Physical Chemistry Chemical Physics. Vol.10, No.33 (2008), 5083-5093
Abstract: The conformational analysis of artemisinin by molecular dynamics and quantum chemistry calculations revealed the existence of seven energy minima with specific interconversion pathways. Among the seven conformers, only Atm1, 2 and 5 were able to undergo bond rearrangements upon Fe2+interaction. These rearrangements were due to a peculiar puckering of the trioxane ring that brings its three oxygen atoms in an ideal geometrical position for interacting with Fe2+ions, promoting an electronic redistribution in the molecule. A rapid molecule rearrangement led to a stable energy minimum structure with an additional ring that is similar to a plant metabolite. Our results suggest an alternative pathway for generating toxic radical chemical species for the malaria parasite, where artemisinin is not toxic by itself but rather is an intermediate for molecular partners that generate radical structures deleterious for the parasite proteins, after electron transfers from the Fe2+/artemisinin complex. © the Owner Societies.
ISSN: 14639076
Appears in Collections:Scopus 2006-2010

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