Metabolites of the Tobacco-specific Nitrosamine 4-(Methylnitrosamino)-l-(3-pyridyl)-l-butanone in Smokers' Urine1

Cancer Research

Volumn 53, Issue 4, 1993, Pages 721-724

  Carmella, Steven G ^a   Akerkar, Shobha ^a   Hecht, Stephen S ^a  

^a Division of Pathology and Toxicology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE; CARCINOGEN; GLUCURONIDE;

ADULT; AGED; ARTICLE; CONTROLLED STUDY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LUNG CANCER; LUNG CARCINOGENESIS; MALE; METABOLISM; METABOLITE; NORMAL HUMAN; PRIORITY JOURNAL; SMOKING; TOBACCO; URINALYSIS; URINE LEVEL;

ADULT; AGED; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; HUMAN; MALE; MASS FRAGMENTOGRAPHY; MIDDLE AGE; NITROSAMINES; SMOKING; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0027522682     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. Shopland, D. R. Eyre. H. J. and Pechacek, T. F. Smoking-attributable cancer mortality in 1991: is lung cancer now the leading cause of death among smokers in the United States? J. Natl. Cancer Inst. 83: 1142-1148. 1991.
2. Hecht, S. S. and Hoffmann. D. Tobacco-specific nitrosamines: an important group of carcinogens in tobacco and tobacco smoke. Carcinogenesis (Lond.), 9: 875-884, 1988.
3. Hecht, S. S. and Hoffmann, D. The relevance of tobacco-specific nitrosamines to human cancer. Cancer Surv. 8: 273-294, 1989.
4. Hecht. S. S. and Hoffmann, D. 4-(Methylnitrosamino)-l-(3-pyridyl)-l-butanone, a nicotine-derived N-nitrosamine, and cancer of the lung and pancreas in humans. In: J. Brugge, T. Curran, E. Harlow, and F. McCormick (eds.), The Origins of Human Cancer: A Comprehensive Review, pp. 745-755. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press, 1991.
5. Morse. M. A. Eklind, K. I. Toussaint, M. Amin, S. G. and Chung. F.-L. Characterization of a glucuronide metabolite of 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone (NNK) and its dose-dependent excretion in the urine of mice and rats. Carcinogenesis (Lond.), 11: 1819-1823, 1990.
6. Hecht, S. S. Trushin, N. Reid-Quinn, C. Burak, E. Jones. A. B. Southers, J. Gombar, C. Carmella, S. G. Anderson, L. M. and Rice, J. M. Metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone in the patas monkey: pharmacokinetics and characterization of glucuronide metabolites. Carcinogenesis (Lond.), in press, 1993.
7. Castonguay. A. Stoner, G. D. Schut, H. A. J. and Hecht, S. S. Metabolism of tobacco-specific N-nitrosamines by cultured human tissues. Proc. Natl. Acad. Sci. USA, 80: 6694-6697, 1983.
8. Smith, T. J. Guo. Z. Y. Gonzalez, F. J. Guengerich, F. P. Stoner, G. D. and Yang, C. S. Metabolism of 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone in human lung and liver microsomes and cytochromes P-450 expressed in hepatoma cells. Cancer Res. 52: 1757-1763, 1992.
9. Carmella, S. G. Kagan, S. S. Kagan, M. Foiles, P. G. Palladino, G. Quart, A. M. Quart, E. and Hecht, S. S. Mass spectrometric analysis of tobacco-specific nitrosamine hemoglobin adducts in snuff-dippers, smokers, and non-smokers. Cancer Res. 50: 5438-5445. 1990.
10. Foiles. P. G. Akerkar. S. A. Carmella, S. G. Kagan, M. Stoner, G. D. Resau, J. H. and Hecht, S. S. Mass spectrometric analysis of tobacco-specific nitrosamine DNA adducts in smokers and non-smokers. Chem. Res. Toxicol. 4: 364-368, 1991.
11. Hecht, S. S. Chen, C. B. and Hoffmann, D. Synthesis of N-nitrosamino aldehydes. Tetrahedron Lett. 8: 593-5%, 1976.
12. Hecht, S. S. Young, R. and Chen, C. B. Metabolism in the F344 rat of 4-(N-methyl-N-nitrosamino)-l-(3-pyridyl)-l-butanone, a tobacco specific carcinogen. Cancer Res. 40: 4144-4150, 1980.
13. Christensen, S. B. and Krogsgaard-Larsen, P. Preparations of deuterium labelled guvacine and isoguvacine. J. Labelled Compd. 17: 191-202, 1977.
14. Adams, J. D. Brunnemann. K. D. and Hoffmann, D. Rapid method for the analysis of tobacco-specific N-nitrosamines by gas liquid chromatography with a thermal energy analyzer. J. Chromatogr. 256: 347-351, 1983.
15. Tricker, A. R. Stickler, D. J. Chawla, J. C. and Preussmann, R. Increased urinary nitrosamine excretion in paraplegic patients. Carcinogenesis (Lond.), 12: 943-946, 1991.
16. Brunnemann, K. D. Genoble, L. and Hoffmann, D. Identification and analysis of a new tobacco-specific N-nitrosamine, 4-(methylnitrosamino)-4-(3-pyridyl)-l-butanol. Carcinogenesis (Lond.), 8: 465-469, 1987.
17. Idris, A. M. Nair, J. Friesen, M. Ohshima, H. Brouet, I. Faustman, E. M. and Bartsch, H. Carcinogenic tobacco-specific nitrosamines are present at unusually high levels in the saliva of oral snuff users in Sudan. Carcinogenesis (Lond.), 13: 1001-1005, 1992.
18. Castonguay, A. Lin, D. Stoner, G. D. Radok, P. Furuya, K. Hecht, S. S. Schut, H. A. J. and Klaunig, J. E. Comparative carcinogenicity in A/J mice and metabolism by cultured mouse peripheral lung of N’-nitrosonornicotine, 4-(methyInitrosamino)-l-(3-pyridyl)-l-butanone and their analogues. Cancer Res. 43: 1223-1229, 1983.
19. Hecht, S. S. Jordan, K. G. Choi, C.-I. and Trushin, N. Effects of deuterium substitution on the tumorigenicity of 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone and 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanol in A/J mice. Carcinogenesis (Lond.), 11: 1017-1020, 1990.
20. Rivenson, A. Hoffmann, D’ Prokopczyk, B. Amin, S. and Hecht, S. S. Induction of lung and exocrine pancreas tumors in F344 rats by tobacco-specific and areca-derived N-nitrosamines. Cancer Res. 48: 6912-6917, 1988.