Tumorigenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol enantiomers and metabolites in the A/J mouse

Carcinogenesis

Volumn 20, Issue 8, 1999, Pages 1577-1582

  Upadhyaya, Pramod ^a   Kenney, Patrick M J ^a   Hochalter, J Bradley ^a   Wang, Mingyao ^a   Hecht, Stephen S ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANOL; 4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE;

ANIMAL EXPERIMENT; ARTICLE; CARCINOGENICITY; CONTROLLED STUDY; ENANTIOMER; FEMALE; GLUCURONIDATION; LUNG TUMOR; METABOLISM; METABOLITE; MICROSOME; MOUSE; NONHUMAN; PRIORITY JOURNAL; URINARY EXCRETION; URINE;

ADENOCARCINOMA; ADENOMA; ANIMALS; CARCINOGENICITY TESTS; CARCINOGENS; DISEASE PROGRESSION; FEMALE; GLUCURONATES; LUNG; LUNG NEOPLASMS; MICE; MICE, INBRED A; MICROSOMES; MICROSOMES, LIVER; NITROSAMINES; SPECIFIC PATHOGEN-FREE ORGANISMS;

EID: 0032842586     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/20.8.1577     Document Type: Article

References (40)

1. Hoffmann, D. and Hecht, S.S. (1985) Nicotine-derived N-nitrosamines and tobacco related cancer: current status and future directions. Cancer Res., 45, 935-944.
2. Hecht, S.S. and Hoffmann, D. (1988) Tobacco-specific nitrosamines, an important group of carcinogens in tobacco and tobacco smoke. Carcinogenesis, 9, 875-884.
3. Hecht, S.S. and Hoffmann, D. (1989) The relevance of tobacco-specific nitrosamines to human cancer. Cancer Surv., 8, 273-294.
4. Hecht, S.S. (1998) Biochemistry, biology and carcinogenicity of tobacco-specific N-nitrosamines. Chem. Res. Toxicol., 11, 559-603.
5. Spiegelhalder, B. and Bartsch, H. (1996) Tobacco-specific nitrosamines. Eur. J. Cancer Prev., 5, 33-38.
6. Magee, P.N. (1989) The experimental basis for the role of nitroso compounds in human cancer. Cancer Surv., 8, 207-239.
7. Magee, P.N. (1996) Nitrosamines and human cancer: introduction and overview. Eur. J. Cancer Prev., 5, 7-10.
8. Bartsch, H. and Spiegelhalder, B. (1996) Environmental exposure to N-nitroso compounds (NNOC) and precursors: an overview. Eur. J. Cancer Prev., 5, 11-18.
9. Preston-Martin, S. and Correa, P. (1989) Epidemiological evidence for the role of nitroso compounds in human cancer. Cancer Surv., 8, 459-473.
10. Carmella, S.G., Akerkar, S. and Hecht, S.S. (1993) Metabolites of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers' urine. Cancer Res., 53, 721-724.
11. Carmella, S.G., Akerkar, S., Richie, J.P.Jr and Hecht, S.S. (1995) Intraindividual and interindividual differences in metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in smokers' urine. Cancer Epidemiol. Biomarkers Prev., 4, 635-642.
12. Richie, J.P., Carmella, S.G., Muscat, J.E., Scott, D.G., Akerkar, S.A. and Hecht, S.S. (1997) Differences in the urinary metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in black and white smokers. Cancer Epidemiol. Biomarkers Prev., 6, 783-790.
13. Hecht, S.S., Carmella, S.G., Murphy, S.E., Akerkar, S., Brunnemann, K.D. and Hoffmann, D. (1993) A tobacco-specific lung carcinogen in the urine of men exposed to cigarette smoke. N. Engl. J. Med., 329, 1543-1546.
14. Parsons, W.D., Carmella, S.G., Akerkar, S., Bonilla, L.E. and Hecht, S.S. (1998) A metabolite of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in the urine of hospital workers exposed to environmental tobacco smoke. Cancer Epidemiol. Biomarkers Prev., 7, 257-260.
15. Kresty, L.A., Carmella, S.G., Borukhova, A., Akerkar, S.A., Gopalakrishnan, R., Harris, R.E., Stoner, G.D. and Hecht, S.S. (1996) Metabolites of a tobacco-specific nitrosamine, 4-(methylnitrosamino)-1 -(3-pyridyl)-1-butanone (NNK), in the urine of smokeless tobacco users: relationship of urinary biomarkers and oral leukoplakia. Cancer Epidemiol. Biomarkers Prev., 5, 521-525.
16. Lackmann, G.M., Salzberger, U., Tollner, U., Chen, M., Carmella, S.G. and Hecht, S.S. (1999) Metabolites of a tobacco-specific carcinogen in the urine of newborns. J. Natl Cancer Inst., 91, 459-465.
17. Meger, M., Meger-Kossien, I., Dietrich, M., Tricker, A.R., Scherer, G. and Adlkofer, F. (1996) Metabolites of 4-(N-methylnitrosamino)-1-(3-pyridyl)-1-butanone in the urine of smokers. Eur. J. Cancer Prev., 5 (suppl. 1), 121-124.
18. Carmella, S.G., Borukhova, A., Akerkar, S.A. and Hecht, S.S. (1997) Analysis of human urine for pyridine-N-oxide metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco-specific lung carcinogen. Cancer Epidemiol. Biomarkers Prev., 6, 113-120.
19. Peterson, L.A., Ng, D.K., Stearns, R.A. and Hecht, S.S. (1994) Formation of NADP(H) analogs of tobacco specific nitrosamines in rat liver and pancreatic microsomes. Chem. Res. Toxicol., 7, 599-608.
20. Staretz, M.E., Koenig, L. and Hecht, S.S. (1997) Effects of long term phenethyl isothiocyanate treatment on microsomal metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F344 rats. Carcinogenesis, 18, 1715-1722.
21. Hecht, S.S. and Trushin, N. (1988) DNA and hemoglobin alkylation by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and its major metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F344 rats. Carcinogenesis, 9, 1665-1668.
22. Hecht, S.S., Spratt, T.E. and Trushin, N. (1997) Absolute configuration of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) formed metabolically from 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Carcinogenesis, 18, 1851-1854.
23. Hecht, S.S., Young, R. and Chen, C.B. (1980) Metabolism in the F344 rat of 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco specific carcinogen. Cancer Res., 40, 4144-4150.
24. Hecht, S.S., Lin, D. and Castonguay, A. (1983) Effects of α-deuterium substitution on the mutagenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Carcinogenesis, 4, 305-310.
25. Castonguay, A., Tjälve, H., Trushin, N. and Hecht, S.S. (1984) Perinatal metabolism of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-bulanone inC57B1 mice. J. Natl Cancer Inst., 72, 1117-1126.
26. Loozen, H.J.J., Godefroi, E.F. and Besters, J.S.M.M. (1975) A novel and efficient route to 5-arylated γ-lactones. J. Org. Chem., 40, 892-894.
27. Spratt, T.E., Peterson, L.A., Confer, W.L. and Hecht, S.S. (1990) Solvolysis of model compounds for α-hydroxylation of N′-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone: evidence for a cyclic oxonium ion intermediate in the alkylation of nucleophiles. Chem. Res. Toxicol., 3, 350-356.
28. McKennis, H., Schwartz, S.L., Turnbull, L.B., Tamaki, E. and Bowman, E.R. (1964) The metabolic formation of γ-(3-pyridyl)-γ-hydroxybutyric acid and its possible intermediary role in the mammalian metabolism of nicotine. J. Biol. Chem., 239, 3981-3989.
29. Trushin, N. and Hecht, S.S. (1999) Stereoselective metabolism of nicotine and tobacco-specific N-nitrosamines to 4-hydroxy-4-(3-pyridyl)butanoic acid in rats. Chem. Res. Toxicol., 12, 164-171.
30. Hecht, S.S., Hatsukami, D.K., Bonilla, L.E. and Hochalter, J.B. (1999) Quantitation of 4-oxo-4-(3-pyridyl)butanoic acid and enantiomers of 4-hydroxy-4-(3-pyridyl)butanoic acid in human urine: a substantial pathway of nicotine metabolism. Chem. Res. Toxicol., 12, 172-179.
31. Guengerich, F.P. (1982) Microsomal enzymes involved in toxicology -analysis and separation. In Hayes, A.W. (ed.) Principles and Methods of Toxicology. Raven Press, New York, NY, pp. 609-634.
32. Flammang, T.J., Yamazoe, Y., Benson, R.W., Roberts, D.W., Potter, D.W., Chu, D.Z., Lang, N.P. and Kadlubar, F.F. (1989) Arachidonic acid-dependent peroxidative activation of carcinogenic arylamines by extrahepatic human tissue microsomes. Cancer Res., 49, 1977-1982.
33. Adams, J.D., LaVoie, E.J., O'Mara-Adams, K.J., Hoffmann, D., Carey, K.D. and Marshall, M.V. (1985) Pharmacokinetics of N′-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in laboratory animals. Cancer Lett., 28, 195-201.
34. Castonguay, A., Lin, D., Stoner, G.D., Radok, P., Furuya, K., Hecht, S.S., Schut, H.A.J. and Klaunig, J.E. (1983) Comparative carcinogenicity in A/J mice and metabolism by cultured mouse peripheral lung of N′-nitrosonornicotine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and their analogues. Cancer Res., 43, 1223-1229.
35. Hecht, S.S., Jordan, K.G., Choi, C.-I. and Trushin, N. (1990) Effects of deuterium substitution on the tumorigenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in A/J mice. Carcinogenesis, 11, 1017-1020.
36. Hoffmann, D., Djordjevic, M.V., Rivenson, A., Desai, D. and Amin, S. (1993) Relative potencies of tobacco-specific N-nitrosamines as inducers of lung tumors in A/J mice. Cancer Lett., 71, 25-30.
37. 2-tetrahydropyranyl adducts. Chem. Res. Toxicol., 8, 607-616.
38. Morse, M.A., Eklind, K.I., Toussaint, M., Amin, S.G. and Chung, F.-L. (1990) Characterization of a glucuronide metabolite of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and its dose-dependent excretion in the urine of mice and rats. Carcinogenesis, 11, 1819-1823.
39. Adams, J.D., LaVoie, E.J. and Hoffmann, D. (1985) On the pharmacokinetics of tobacco-specific N-nitrosamines in Fischer rats. Carcinogenesis, 6, 509-511.
40. Atawodi, S.E., Michelsen, K. and Richter, E. (1994) Metabolism of a glucuronide conjugate of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in rats. Arch. Toxicol., 69, 14-17.