title: A plausible mechanism for the mutagenic activity (Salmonella typhimurium TA100) of MX compounds: a formation of CG-CG(+)-CG radical cation by one-electron reduction.
abstract: Combining our previous QSAR work with recent high-level quantum mechanical calculations, a plausible mechanism for the mutagenic activity of halogenated furanones (so called MX compounds) in Salmonella typhimurium TA100 tester strain is proposed. The mechanism involves one-electron reduction as a key step and it seems reasonable to suggest that the mutagenicity of these direct-acting compounds may be a purely thermodynamic phenomenon, rather than the result of site-specific binding or adduct formation. Overall, the proposed model is consistent with the most experimental findings.
authors.affiliation: Department of Chemistry, University of Kuopio, Finland.
authors.forename: K
authors.initials: K
authors.lastname: Tuppurainen
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D004583:Electrons; D005663:Furans / Q000633:toxicity*; D008962:Models, Theoretical; D008969:Molecular Sequence Data; D016296:Mutagenesis / Q000502:physiology*; D009153:Mutagens / Q000633:toxicity*; D012486:Salmonella typhimurium / Q000235:genetics; D013329:Structure-Activity Relationship; D013816:Thermodynamics
chemical_list: D005663:Furans; D009153:Mutagens; C054121:3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone