Ce(IV)-mediated formation of benzenediazonium ion from a non-aminoazo dye, 1-phenylazo-2-hydroxy-naphthalene (Sudan I) and its binding to DNA

Abstract

Ce(IV) ions in acidic medium convert a carcinogenic non-aminoazo dye, 1-phenylazo-2-hydroxy-naphthalene (Sudan I) into an ultimate carcinogen, which binds to calf thymus DNA. The principal product of Sudan I oxidation by the Ce(IV) system is the benzenediazonium ion. A minor product is the dihydroxyderivative of Sudan I, 1-(4-hydroxyphenylazo)-2,6-dihydroxynaphthalene. Other minor coloured products (yellow and brown) were not identified. The principal product (the benzenediazonium ion) is responsible for the carcinogenicity of Sudan I, as it covalently binds to DNA. Ce(IV) ions in acidic medium represent a suitable model system, which imitates the activation route of carcinogenic azo dyes.