Identification of the major serum albumin adduct formed by 4-aminobiphenyl in vivo in rats

Cancer Res. 1985 Oct;45(10):5122-7.

Abstract

Serum albumin was isolated from rats at 27 h after administration of the carcinogen [2,2'-3H]-4-aminobiphenyl. Pronase digestion of the purified albumin yielded a mixture of radiolabeled materials which was resolved into 5 major components by reverse-phase liquid chromatography. From detailed UV, 1H-NMR, and mass spectral analyses, four of these were determined to be 4-aminobiphenyl, 4'-hydroxy-4-acetylaminobiphenyl, and two other metabolites, all of which are presumed to be non-covalently associated with the serum albumin. The fifth component, however, resulted from covalent bond formation and was identified as a tetrapeptide containing 3-tryptophanyl-4-acetylaminobiphenyl, the amino acid sequence of which was H2N-ala-trp-ala-val. Since rat serum albumin contains only a single tryptophan residue in a hydrophobic drug binding site, its high selectivity for carcinogen binding suggests a unique role for this protein in the detoxification and/or transport of ultimate carcinogenic metabolites.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acids / analysis
  • Aminobiphenyl Compounds / metabolism*
  • Aminobiphenyl Compounds / toxicity
  • Animals
  • Carcinogens / metabolism*
  • Magnetic Resonance Spectroscopy
  • Male
  • Rats
  • Rats, Inbred Strains
  • Serum Albumin / metabolism*

Substances

  • Amino Acids
  • Aminobiphenyl Compounds
  • Carcinogens
  • Serum Albumin
  • 4-biphenylamine