title: Quantitative structure-activity relationships for toxicity and genotoxicity of halogenated aliphatic compounds: wing spot test of Drosophila melanogaster.
abstract: Halogenated aliphatic compounds were evaluated for toxic and genotoxic effects in the somatic mutation and recombination test employing Drosophila melanogaster. The tested chemicals included chlorinated, brominated and iodinated; mono-, di- and tri-substituted; saturated and unsaturated alkanes: 1,2-dibromoethane, 1-bromo-2-chloroethane, 1-iodopropane, 2,3-dichloropropene, 3-bromo-1-propene, epibromohydrin, 2-iodobutane, 3-chloro-2-methylpropene, 1,2,3-trichloropropane, 1,2-dichloroethane, 1,2-dichlorobutane, 1-chloro-2-methylpropane, 1,3-dichloropropane, 1,2-dichloropropane, 2-chloroethymethylether, 1-bromo-2-methylpropane and 1-chloropentane. N-methyl-N-nitrosourea served as the positive and distilled water as the negative control. The set of chemicals for the toxicological testing was selected by the use of statistical experiment design. Group of unsaturated aliphatic hydrocarbons were generally more toxic than saturated analogues. The genotoxic effect was observed with 14 compounds in the wing spot test, while 3 substances did not show any genotoxicity by using the wing spot test at 50% lethal concentration. The highest number of wing spots was observed in genotoxicity assay with 1-bromo-2-chloroethane, 1,2-dichloroethane, 1,2-dibromoethane and 1-iodopropane. Nucleophilic superdelocalizability calculated by quantum mechanics appears to be a good parameter for prediction of both toxicity and genotoxicity effects of halogenated aliphatic compounds.
authors.affiliation: Department of Molecular Biology, Masaryk University, Kotlarska 2, 611 37 Brno, Czech Republic. chroust@sci.muni.cz
authors.forename: Karel
authors.initials: K
authors.lastname: Chroust
authors.forename: Martina
authors.initials: M
authors.lastname: Pavlová
authors.forename: Zbynek
authors.initials: Z
authors.lastname: Prokop
authors.forename: Jan
authors.initials: J
authors.lastname: Mendel
authors.forename: Katerina
authors.initials: K
authors.lastname: Bozková
authors.forename: Zdenek
authors.initials: Z
authors.lastname: Kubát
authors.forename: Veronika
authors.initials: V
authors.lastname: Zajícková
authors.forename: Jiri
authors.initials: J
authors.lastname: Damborský
mesh_terms: D000818:Animals; D004331:Drosophila melanogaster / Q000187:drug effects* / Q000235:genetics; D006846:Hydrocarbons, Halogenated / Q000737:chemistry / Q000633:toxicity*; D009152:Mutagenicity Tests / Q000379:methods; D009153:Mutagens / Q000737:chemistry / Q000633:toxicity; D009154:Mutation / Q000187:drug effects; D021281:Quantitative Structure-Activity Relationship
chemical_list: D006846:Hydrocarbons, Halogenated; D009153:Mutagens