title: Topological study of the late steps of the artemisinin decomposition process: modeling the outcome of the experimentally obtained products.
abstract: By using 6,7,8-trioxabicyclo[3.2.2]nonane as the artemisinin model and dihydrated Fe(OH)(2) as the heme model, we report a theoretical study of the late steps of the artemisinin decomposition process. The study offers two viewpoints: first, the energetic and geometric parameters are obtained and analyzed, and hence, different reaction paths have been studied. The second point of view uses the electron localization function (ELF) and the atoms in molecules (AIM) methodology, to conduct a complete topological study of such steps. The MO analysis together with the spin density description has also been used. The obtained results agree nicely with the experimental data, and a new mechanistic proposal that explains the experimentally determined outcome of deoxiartemisinin has been postulated.
authors.affiliation: Departament de Química Física i Analítica, Universitat Jaume I, Avda. Sos Baynat s/n, 12071 Castelló, Spain.
authors.forename: Pamela
authors.initials: P
authors.lastname: Moles
authors.forename: Mónica
authors.initials: M
authors.lastname: Oliva
authors.forename: Vicent S
authors.initials: VS
authors.lastname: Safont
mesh_terms: D000473:Alkanes / Q000737:chemistry* / Q000378:metabolism; D037621:Artemisinins / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry* / Q000378:metabolism; D003198:Computer Simulation; D004583:Electrons; D005296:Ferrous Compounds / Q000737:chemistry* / Q000378:metabolism; D006418:Heme / Q000378:metabolism; D006420:Hemeproteins / Q000378:metabolism; D006454:Hemoglobins / Q000378:metabolism; D008956:Models, Chemical; D008958:Models, Molecular; D008962:Models, Theoretical; D018716:Molecular Mimicry; D010084:Oxidation-Reduction; D010961:Plasmodium / Q000187:drug effects / Q000378:metabolism; D017382:Reactive Oxygen Species; D013816:Thermodynamics
chemical_list: C558706:6,7,8-trioxabicyclo(3.2.2)nonane; D000473:Alkanes; D037621:Artemisinins; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005296:Ferrous Compounds; D006420:Hemeproteins; D006454:Hemoglobins; D017382:Reactive Oxygen Species; C020753:hemozoin; D006418:Heme; C055261:deoxyartemisinin; C031327:artemisinin; C034236:ferrous oxide; C017573:nonane