title: Potent mutagenicity in the Ames test of 2-cyano-4-nitroaniline and 2,6-dicyano-4-nitroaniline, components of disperse dyes.
abstract: Genotoxicity data on commercial azo dyes and their components remain sparse, despite their widespread use. We have tested the mutagenicity of 2-cyano-4-nitroaniline (CNNA) and 2,6-dicyano-4-nitroaniline (CNCNNA), components of azo dyes such as Disperse Blue 165 and Disperse Red 73, in Ames test strains. Both compounds are extraordinarily potent frameshift mutagens, with much greater activity than structurally similar dihalonitroanilines and halodinitroanilines. Analysis of the responses of strains over-expressing or deficient in bioactivation enzymes shows that bacterial nitroreductase and acetyl CoA: arylamine N-acetyltransferase are important mediators of the mutagenicity of CNNA and CNCNNA.
authors.affiliation: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada.
authors.forename: P David
authors.initials: PD
authors.lastname: Josephy
authors.affiliation: Department of Chemistry, University of Agriculture, Faisalabad, Pakistan.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Zahid
authors.affiliation: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada.
authors.forename: Joban
authors.initials: J
authors.lastname: Dhanoa
authors.affiliation: State of Sao Paulo University "Julio De Mesquita Filho" (UNESP), Araraquara, Sao Paulo State, Brazil.
authors.forename: Giovanna Brondino Duarte
authors.initials: GB
authors.lastname: de Souza
authors.affiliation: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada.
authors.forename: Hilary
authors.initials: H
authors.lastname: Groom
authors.affiliation: Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada.
authors.forename: Meghan
authors.initials: M
authors.lastname: Lambie
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry / Q000633:toxicity*; D004305:Dose-Response Relationship, Drug; D009152:Mutagenicity Tests; D009153:Mutagens / Q000737:chemistry / Q000633:toxicity*; D012475:Salmonella / Q000187:drug effects* / Q000235:genetics*
chemical_list: D000814:Aniline Compounds; D009153:Mutagens; C019498:4-nitroaniline
keywords: Ames test; cyanoaromatics; disperse dyes; nitroanilines