Peroxidase-activated carcinogenic azo dye Sudan I (Solvent Yellow 14) binds to guanosine in transfer ribonucleic acid

Gen Physiol Biophys. 1995 Feb;14(1):39-49.

Abstract

Peroxidase in the presence of hydrogen peroxide catalyzes in vitro the activation of the carcinogenic azo dye Sudan I (1-phenylazo-2-hydroxynaphthalen) to tRNA-, homopolyribonucleotide- and 5'-monophosphate nucleoside-bound products. tRNA, poly G and guanosine 5'-monophosphate modified by activated Sudan I become colored and have an absorption maximum of approx. 480 nm. Cochromatographic analysis of adducts obtained by a reaction with tRNA and guanosine 5'-monophosphate on a thin layer of cellulose showed that the major Sudan I-tRNA adduct was formed by a reaction of activated Sudan I with guanosine in tRNA. The radical mechanism of the binding of the Sudan I molecule, containing the whole azo aromatic system, to nucleic acids is discussed.

MeSH terms

  • Animals
  • Binding Sites
  • Carcinogens / metabolism*
  • Coloring Agents / metabolism*
  • Guanosine / metabolism*
  • Guanosine Monophosphate / metabolism
  • In Vitro Techniques
  • Naphthols / metabolism*
  • Nucleotides / metabolism
  • Peroxidase / metabolism
  • Polyribonucleotides / metabolism
  • RNA, Transfer / metabolism*
  • Rats

Substances

  • Carcinogens
  • Coloring Agents
  • Naphthols
  • Nucleotides
  • Polyribonucleotides
  • Guanosine
  • 1-phenylazo-2-naphthol
  • Guanosine Monophosphate
  • RNA, Transfer
  • Peroxidase