title: Directly-acting mutagens formed from N-nitroso-N-(formylmethyl)alkylamines.
abstract: Directly-acting mutagens formed from N-nitroso-N-(formylmethyl)alkylamines (I) were isolated and identified as N-nitroso-N-alkyl-1-hydroxyimino-2-oxoethylamines (II). Their structures were elucidated on the basis of nuclear magnetic resonance spectra and confirmed by leading to their crystalline 2,4-dinitrophenylhydrazone. II (alkyl = ethyl and n-butyl) were strongly mutagenic to Salmonella typhimurium TA1535 and Escherichia coli WP2 hcr- without metabolic activation, while II with a tert-butyl group was not mutagenic. The formation of II from I is considered to proceed by the nitrosation of I, indicating a possible involvement of a formylmethyl metabolite in the carcinogenesis of nitrosamines with a 2-hydroxyethyl group.
authors.affiliation: Tokyo Biochemical Research Institute, Japan.
authors.forename: E
authors.initials: E
authors.lastname: Suzuki
authors.forename: M
authors.initials: M
authors.lastname: Osabe
authors.forename: M
authors.initials: M
authors.lastname: Mochizuki
authors.forename: M
authors.initials: M
authors.lastname: Okada
mesh_terms: D000818:Animals; D004926:Escherichia coli; D009682:Magnetic Resonance Spectroscopy; D009152:Mutagenicity Tests; D009153:Mutagens / Q000302:isolation & purification*; D009602:Nitrosamines / Q000378:metabolism*; D051381:Rats; D012486:Salmonella typhimurium; D013329:Structure-Activity Relationship
chemical_list: D009153:Mutagens; D009602:Nitrosamines