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Carcinogenesis

Metabolic Activation of N-Hydroxy Arylamines and N-Hydroxy Heterocyclic Amines by Human Sulfotransferase(s)

H-C. Chou, N. P. Lang and F. F. Kadlubar
H-C. Chou
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N. P. Lang
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F. F. Kadlubar
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DOI:  Published February 1995
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Abstract

Several N-hydroxy metabolites of carcinogenic arylamines and heterocyclic amines were examined as substrates for bioactivation by human liver sulfotransferases (STs). Among the N-hydroxy derivatives studied, N-hydroxy-2-acetylaminofluorene, N-hydroxy-2-aminofluorene, N-hydroxy-4,4′-methylene-bis(2-chloroaniline), N-hydroxy-2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, and N-hydroxy-2-amino-6-methyldipyrido[1,2-a:3′,2′-d]imidazole were each metabolically activated by 3′-phosphoadenosine-5′-phosphosulfate-dependent human liver STs. No ST-mediated DNA binding of N-hydroxy-2-amino-3-methylimidazo[4,5-f]quinoline or N-hydroxy-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline was detected under our assay conditions. In the 12 human hepatic cytosols studied, the extent of 3′-phosphoadenosine-5′-phosphosulfate-dependent DNA binding of the N-hydroxy derivatives were all significantly correlated with levels of thermostable phenol ST (TS-PST) activity but not with thermolabile phenol ST or dehydroepiandrosterone ST activities. The propensity of these N-hydroxy arylamines and N-hydroxy heterocyclic amines to serve as selective substrates for human TS-PST was further confirmed by inhibition with 2,6-dichloro-4-nitrophenol and by thermostability studies.

N-hydroxy-2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and N-hydroxy-4,4′-methylene-bis(2-chloroaniline) were also used as substrates to study ST-dependent metabolic activation in other human tissue preparations. 3′-phosphoadenosine-5′-phosphosulfate-dependent DNA binding activity was detected in human liver and colon cytosols but not in pancreas, larynx, or urinary bladder epithelial cytosols. Since the TS-PST appears to be expressed polymorphically in human populations, the finding that human TS-PST is capable of metabolically activating N-hydroxy metabolites of several carcinogenic arylamines and heterocyclic amines suggests that TS-PST may have an important role in determining interindividual susceptibility to these environmental and dietary carcinogens.

Footnotes

  • ↵2 To whom requests for reprints should be addressed.

  • Received July 14, 1994.
  • Accepted November 30, 1994.
  • ©1995 American Association for Cancer Research.
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February 1995
Volume 55, Issue 3
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Metabolic Activation of N-Hydroxy Arylamines and N-Hydroxy Heterocyclic Amines by Human Sulfotransferase(s)
H-C. Chou, N. P. Lang and F. F. Kadlubar
Cancer Res February 1 1995 (55) (3) 525-529;

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Metabolic Activation of N-Hydroxy Arylamines and N-Hydroxy Heterocyclic Amines by Human Sulfotransferase(s)
H-C. Chou, N. P. Lang and F. F. Kadlubar
Cancer Res February 1 1995 (55) (3) 525-529;
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