Activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b] pyridine by cDNA-expressed human and rat arylsulfotransferases

Jpn J Cancer Res. 1994 Dec;85(12):1220-8. doi: 10.1111/j.1349-7006.1994.tb02933.x.

Abstract

Sulfation plays an obligatory role in the activation of N-hydroxy derivatives of carcinogenic arylamine (amide)s and heterocyclic amines. We found that the hepatic sulfotransferase-mediated covalent binding of 3H-labeled 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b] pyridine (N-OH-PhIP) to calf thymus DNA was 3.3 and 12.9 times higher with human cytosol preparation than with male and female rat cytosol preparations, respectively, in the presence of 3'-phosphoadenosine 5'-phosphosulfate. To assess the activating capacities of individual phenol-sulfating sulfotransferases, five different forms, human ST1A2 and ST1A3 and rat ST1A1, ST1B1 and ST1C1, were expressed in heterologous cells. All five sulfotransferases mediated the activation of N-OH-PhIP to DNA-bound products. The extents of the binding, however, differed considerably among these forms. Human ST1A2 and ST1A3 mediated the activation of N-OH-PhIP at 5.2- and 6.2-fold higher rates than did rat ST1C1, a main N-hydroxy-2-acetylaminofluorene-activating sulfotransferase, in rat liver. Extents of the binding of N-OH-PhIP in human hepatic cytosols of different individuals were positively correlated with the contents of immunoreactive ST1A2/3. These results suggest a potential role of human liver sulfotransferases in N-OH-PhIP activation. In contrast, the low sulfotransferase-mediated activation of N-OH-PhIP in rat liver is consistent with the lack of PhIP hepatocarcinogenicity in this species.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Arylsulfotransferase / chemistry
  • Arylsulfotransferase / metabolism*
  • Biotransformation
  • Carcinogens / metabolism*
  • Carcinogens / toxicity
  • Cells, Cultured
  • Chlorocebus aethiops
  • Cytosol / enzymology
  • DNA / metabolism
  • Escherichia coli
  • Female
  • Humans
  • Imidazoles / metabolism*
  • Imidazoles / toxicity
  • Liver / enzymology*
  • Male
  • Molecular Sequence Data
  • Phosphoadenosine Phosphosulfate / metabolism
  • Rats
  • Species Specificity

Substances

  • Carcinogens
  • Imidazoles
  • Phosphoadenosine Phosphosulfate
  • DNA
  • 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
  • Arylsulfotransferase