A new way to carcinogenicity of azo dyes: the benzenediazonium ion formed from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene(Sudan I) by microsomal enzymes binds to deoxyguanosine residues of DNA

Cancer Lett. 1988 Jun 30;40(3):327-33. doi: 10.1016/0304-3835(88)90092-4.

Abstract

1-Phenylazo-2-hydroxynaphthalene (Sudan I) activated by pre-incubation with microsomal enzymes of rat livers covalently binds to DNA from calf thymus. Benzenediazonium ion formed from Sudan I by activation with microsomal enzymes is the principal active metabolite, which binds to DNA. Enzymatic hydrolysis of modified (14C-labelled) DNA, followed by separation of deoxynucleosides on a Sephadex G-10 column revealed that deoxyguanosine is the principal target for the binding of activated Sudan I. The high-performance liquid chromatographic (HPLC) analysis indicate that probably more than one radioactive adduct of activated Sudan I with deoxyguanosine is formed.

MeSH terms

  • Animals
  • Biotransformation
  • Carcinogens*
  • Chromatography, High Pressure Liquid
  • Coloring Agents*
  • DNA / metabolism
  • Deoxyguanosine / metabolism*
  • Diazonium Compounds / metabolism*
  • Male
  • Microsomes, Liver / metabolism*
  • Naphthols / metabolism*
  • Rats
  • Rats, Inbred Strains

Substances

  • Carcinogens
  • Coloring Agents
  • Diazonium Compounds
  • Naphthols
  • benzenediazonium
  • 1-phenylazo-2-naphthol
  • DNA
  • Deoxyguanosine