title: About the mutagenicity of chlorine-substituted furanones and halopropenals. A QSAR study using molecular orbital indices.
abstract: Electron affinities, frontier molecular orbital energies and electron densities at individual carbon atoms were calculated for 11 chlorofuranones including the strong mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) and for 5 halopropenals by semi-empirical AM1 and ab initio STO-3G methods. Significant correlations were found between Ames TA100 mutagenicity and the following AM1 electronic parameters of chlorofuranones: electron affinity (r = 0.9556). LUMO energy (r = 0.9332) and frontier electron density of LUMO at the alpha-carbon (r = 0.8882). In halopropenals only LUMO electron density at the beta-carbon correlates well with mutagenicity. The observed correlations suggest a reaction mechanism in which chlorofuranones and halopropenals act as electron acceptors in the interaction with DNA.
authors.affiliation: Department of Chemistry, University of Kuopio, Finland.
authors.forename: K
authors.initials: K
authors.lastname: Tuppurainen
authors.forename: S
authors.initials: S
authors.lastname: Lötjönen
authors.forename: R
authors.initials: R
authors.lastname: Laatikainen
authors.forename: T
authors.initials: T
authors.lastname: Vartiainen
authors.forename: U
authors.initials: U
authors.lastname: Maran
authors.forename: M
authors.initials: M
authors.lastname: Strandberg
authors.forename: T
authors.initials: T
authors.lastname: Tamm
mesh_terms: D000447:Aldehydes / Q000737:chemistry / Q000633:toxicity*; D000475:Alkenes / Q000737:chemistry / Q000633:toxicity*; D002713:Chlorine / Q000737:chemistry*; D005663:Furans / Q000737:chemistry / Q000633:toxicity*; D006219:Halogens / Q000737:chemistry / Q000633:toxicity; D015394:Molecular Structure; D009152:Mutagenicity Tests; D009153:Mutagens / Q000737:chemistry / Q000633:toxicity*; D012486:Salmonella typhimurium / Q000235:genetics
chemical_list: D000447:Aldehydes; D000475:Alkenes; D005663:Furans; D006219:Halogens; D009153:Mutagens; D002713:Chlorine