Human phenol sulfotransferases hP-PST and hM-PST activate propane 2-nitronate to a genotoxicant

Carcinogenesis

Volumn 21, Issue 2, 2000, Pages 295-299

  Kreis, Patricia ^a   Brandner, Stefanie ^a   Coughtrie, Michael W H ^b   Pabel, Ulrike ^c   Meinl, Walter ^c   Glatt, Hansruedi ^c   Andrae, Ulrich ^a  

^a INSTITUTE OF EPIDEMIOLOGY   (Germany)

^b UNIVERSITY OF DUNDEE   (United Kingdom)

^c GERMAN INSTITUTE OF HUMAN NUTRITION   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROPROPANE; 8 AMINOGUANOSINE; 8 HYDROXYDEOXYGUANOSINE; ARYL SULFOTRANSFERASE; CARCINOGEN; HYDROXYSTEROID SULFOTRANSFERASE; MONOAMINE; NITROSO DERIVATIVE; OXIME DERIVATIVE; PHENOL; PROPANE; SOLVENT;

ARTICLE; CELL LINE; CONTROLLED STUDY; DNA MODIFICATION; DNA REPAIR; DNA SYNTHESIS; ENZYME ACTIVITY; GENOTOXICITY; HUMAN; HUMAN CELL; LIVER CARCINOGENESIS; METABOLISM; NONHUMAN; PRIORITY JOURNAL; RAT;

EID: 0033974994     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/21.2.295     Document Type: Article

References (37)

1. Lewis, T.R., Ulrich, C.E. and Busey, W.M. (1979) Subchronic inhalation toxicity of nitromethane and 2-nitropropane. J. Environ. Pathol. Toxicol., 2, 233-249.
2. Fiala, E.S., Czerniak, R., Castonguay, A., Conaway, C.C. and Rivenson, A. (1987) Assay of 1-nitropropane, 2-nitropropane, 1-azoxypropane and 2-azoxypropane for carcinogenicity by gavage in Sprague-Dawley rats. Cancinogenesis, 8, 1947-1949.
3. Sodum, R.S., Sohn, O.S., Nie, G. and Fiala, E.S. (1994) Activation of the liver carcinogen 2-nitropropane by aryl sulfotransferase. Chem. Res. Toxicol., 7, 344-351.
4. Fiala, E.S., Conaway, C.C. and Mathis, J.E. (1989) Oxidative DNA and RNA damage in the livers of Sprague-Dawley rats treated with the hepatocarcinogen 2-nitropropane. Cancer Res., 49, 5518-5522.
5. Sodum, R.S., Nie, G. and Fiala, E.S. (1993) 8-Aminoguanine: a base modification produced in rat liver nucleic acids by the hepatocarcinogen 2-nitropropane. Chem. Res. Toxicol., 6, 269-276.
6. 2-Amination of guanine to 2-hydrazinohypoxanthine, a novel in vivo nucleic acid modification produced by the hepatocarcinogen 2-nitropropane. Chem. Res. Toxicol., 11, 1453-1459.
7. Sodum, R.S. and Fiala, E.S. (1997) Amination of tyrosine in liver cytosol protein of male F344 rats treated with 2-nitropropane, 2-nitrobutane. 3-nitropentane, or acetoxime. Chem. Res. Toxicol., 10, 1420-1426.
8. Andrae, U., Homfeldt, H., Vogl. L., Lichtmannegger, J. and Summer, K.-H. (1988) 2-Nitropropane induces DNA repair synthesis in rat hepatocytes in vitro and in vivo. Carcinogenesis, 9, 811-815.
9. Guo, N., Conaway, C.C., Hussain, N.S. and Fiala, E.S. (1990) Sex and organ differences in oxidative DNA and RNA damage due to treatment of Sprague-Dawley rats with acetoxime or 2-nitropropane. Carcinogenesis, 11, 1659-1662.
10. Andrae, U., Kreis, P., Coughtrie, M.W.H., Pabel, U., Meinl, W., Bartsch, I. and Glatt, H.R. (1999) Activation of propane 2-nitronate to a genotoxicant in V79-derived cell lines engineered for the expression of rat hepatic sulfotransferases. Mutat. Res., 439, 191-197.
11. Wiebel, F.J., Singh, J., Schindler, E. and Summer, K.-H. (1980) UDP-Glucuronosyl-, phenol sulfo-, and glutathione-S-transferase activities of mammalian cells in permanent culture. Toxicology, 17, 123-126.
12. Wiebel, F.J., Kiefer, F., Krupski, G. and Schuller, H.M. (1986) Expression of glutathione S-transferase and phenol sulfotransferase, but not of UDP-glucuronosyltransferase, in the human lung tumor cell lines NCI-H322 and NCI-H358, Biochem. Pharmacol., 35, 1337-1343.
13. Davies, J.E., Mynett, K., Gescher, A. and Chipman, J.K. (1993) DNA modification and repair by 2-nitropropane is extensive in hepatocytes of rats compared to those of human and mice. Mutat. Res., 287, 157-164.
14. Glatt, H.R., Pauly, K., Piée-Staffa, A., Seidel, A., Hornhardt, S. and Czich, A. (1994) Activation of promutagens by endogenous and heterologous sulfotransferases expressed in continuous cell cultures. Toxicol. Lett., 72, 13-21.
15. Roscher, E., Ziegler-Skylakakis, K. and Andrae, U. (1990) Involvement of different pathways in the genotoxicity of nitropropanes in cultured mammalian cells. Mutagenesis, 5, 375-380.
16. Glatt, H.R., Gemperlein, I., Setiabudi, F., Platt, K.-L. and Oesch, F. (1990) Expression of xenobiotic-metabolising enzymes in propagatable cell cultures and induction of micronuclei by 13 compounds. Mutagenesis, 5, 241-249.
17. Forbes, K.J., Hagen, M., Glatt, H.R., Hume, R. and Coughtrie, M.W.H. (1995) Human fetal adrenal hydroxysteroid sulphotransferase: cDNA cloning, stable expression in V79 cells and functional characterisation of the expressed enzyme. Mol. Cell. Endocrinol., 112, 53-60.
18. Jones, A.L., Hagen, M., Coughtrie, M.W.H., Roberts, R.C. and Glatt, H.R. (1995) Human platelet phenolsulfotransferases: cDNA cloning, stable expression in V79 cells and identification of a novel allelic variant of the phenol-sulfating form. Biochem. Biophys. Res. Commun., 208, 855-862.
19. Raftogianis, R.B., Wood, T.C., Otterness, D.M., van Loon, J.A. and Weinshilboum, R.M. (1997) Phenol sulfotransferase pharmacogenetics in humans: association of common SULTIAI alleles with TS PST phenotype. Biochem. Biophys. Res. Commun., 239, 298-304.
20. Czich, A., Bartsch, I., Dogra, S., Hornhardt, S. and Glatt, H.R. (1994) Stable heterologous expression of hydroxysteroid sulfotransferase in Chinese hamster V79 cells and their use for toxicological investigations. Chem. Biol. Interact., 92, 119-128.
21. Pettijohn, D.E. and Hanawalt, P.C. (1964) Evidence for repair replication of ultraviolet-damaged DNA in bacteria. J. Mol. Biol. 9, 395-410.
22. Andrae, U. (1984) Evidence for the involvement of cytochrome P-450-dependent monooxygenase(s) in the formation of genotoxic metabolites from N-hydroxyurea. Biochem. Biophys. Res. Commun., 118, 409-415.
23. Smith, C.A. and Hanawalt, P.C. (1976) Repair replication in human cells. Simplified determination utilizing hydroxyurea. Biochim. Biophys. Acta. 432, 336-347.
24. Topinka, J., Andrae, U., Schwarz, L.R. and Wolff, T. (1993) Cyproterone acetate generates DNA adducts in rat liver and in primary rat hepatocyte cultures. Carcinogenesis, 14, 423-427.
25. Gupta, R.C. (1984) Non-random binding of the carcinogen N-hydroxy-2-acetylaminofluorene to repetitive sequences of rat liver DNA in vivo. Proc. Natl Acad. Sci. USA, 81, 6943-6947.
26. Kreis, P., Degen, G.H. and Andrae, U. (1998) Sulfotransferase-mediated genotoxicity of propane 2-nitronate in cultured ovine seminal vesicle cells. Mutat. Res., 413, 69-81
27. Fiala, E.S., Nie, G., Sodum, R., Conaway, C.C. and Sohn, O.S. (1993) 2-Nitropropane-induced liver DNA and RNA base modifications: differences between Sprague-Dawley rats and New Zealand White rabbits. Cancer Lett., 74, 9-14.
28. Dunn, R.T. and Klaassen, C.D. (1998) Tissue-specific expression of rat sulfotransferase messenger RNAs. Drug Metab. Dispos., 26, 598-604.
29. Sundaram, R.S., Szumlanski, C., Otterness, D., Van Loon, J.A. and Weinshilboum, R.D. (1989) Human intestinal phenol sulfotransferase: assay conditions, activity levels and partial purification of the thermolabile form. Drug Metab. Dispos., 17, 255-264.
30. Pacifici, G.M., Eligi, M. and Giuliani, L. (1993) (+) and (-) terbutaline are sulphated at a higher rate in human intestine than in liver. Eur. J. Clin. Pharmacol., 45, 483-487.
31. Falany, J.L., Azziz, R. and Falany, C.N. (1998) Identification and characterization of cytosolic sulfotransferases in normal human endometrium. Chem. Biol. Interact., 109, 329-339.
32. Teubner, W., Pabel, U., Meinl, W., Coughtrie, M.W.H., Falany, C.N., Kretzschmar, M., Seidel, A. and Glatt, H.R. (1998) Characterisation of sulfotransferases in human colon mucosa and their expression in Salmonella typhimurium for the study of the activation of promutagens. Naunyn Schmiedebergs Arch. Pharmacol., 357, R135.
33. Goldstein, D.S., Swoboda, K.J., Miles, J.M., Coppack, S.W., Aneman, A., Holmes, C., Lamensdorf, I. and Eisenhofer, G. (1999) Sources and physiological significance of plasma dopamine sulfate. J. Clin. Endocrinol. Metab., 84, 2523-2531.
34. World Health Organization (1992) Environmental Health Criteria 138: 2-Nitropropane. International Programme on Chemical Safety, World Health Organization, Geneva.
35. Scott, E.W. (1943) The metabolism of monoparaffins. III. The concentration of nitroethane, nitrite and nitrate in the blood of rabbits during exposure by inhalation and oral administration. J. Ind. Hyg. Toxicol., 25, 20-25.
36. Dequidt, J., Vasseur, P. and Potencier, J. (1972) Etude toxicologique experimentale de quelques nitroparffines: I. Etude du 2-nitropropane. Bull. Soc. Pharm. Lille, 1972, 83-89.
37. Fiala, E.S., Sohn, O.S., Li, H., El-Bayoumy, K. and Sodum, R.S. (1997) Inhibition of 2-nitropropane-induced rat liver DNA and RNA damage by benzyl selenocyanate. Carcinogenesis, 18, 1809-1815.