title: Mutagenic activity of the methyl and phenyl derivatives of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoxaline (IQx) in the Ames test.
abstract: The mutagenic activity of 15 different mono-, di-, tri-, and tetramethyl derivatives of the food mutagen IQx (2-amino-3-methylimidazo[4,5-f]quinoxaline), one diphenyl derivative of IQx and two phenyl derivatives of 5-MeIQx (2-amino-3,5-dimethylimidazo[4,5-f]quinoxaline) were studied in the Ames test with Salmonella typhimurium TA98 and enzymatic activation (S9). The number and positioning of the methyl groups strongly affected the mutagenic activity. The phenylated compounds showed weak mutagenic potency. It seems that both resonance stabilization of the nitrenium ion and steric effects are important in determining mutagenic potency.
authors.affiliation: Graduate Research Laboratory, Stabekk College, Bekkestua, Norway.
authors.forename: R
authors.initials: R
authors.lastname: Vikse
authors.forename: A
authors.initials: A
authors.lastname: Knapstad
authors.forename: L
authors.initials: L
authors.lastname: Klungsøyr
authors.forename: S
authors.initials: S
authors.lastname: Grivas
mesh_terms: D000818:Animals; D001711:Biotransformation; D004305:Dose-Response Relationship, Drug; D005502:Food; D066298:In Vitro Techniques; D007536:Isomerism; D008862:Microsomes, Liver / Q000378:metabolism; D016296:Mutagenesis / Q000187:drug effects*; D009152:Mutagenicity Tests; D009153:Mutagens; D011804:Quinolines / Q000737:chemistry; D011810:Quinoxalines / Q000633:toxicity*; D051381:Rats; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D009153:Mutagens; D011804:Quinolines; D011810:Quinoxalines; C029216:2-amino-3-methylimidazo(4,5-f)quinoline