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

Volumn 11, Issue 10, 1990, Pages 1819-1823

  Morse, Mark A ^a   Eklind, Karin I ^a   Toussaint, Mary ^a   Amin, Shantu G ^a   Chung, Fung Lung ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

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

ANIMAL EXPERIMENT; ARTICLE; METABOLITE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT; URINE LEVEL;

ANIMAL; BIOTRANSFORMATION; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; GLUCURONATES; GLUCURONIDASE; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICE; MICE, INBRED A; NITROSAMINES; RATS; RATS, INBRED F344; SPECTRUM ANALYSIS, MASS; SUPPORT, U.S. GOV'T, P.H.S.; TRITIUM;

EID: 0025147275     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/11.10.1819     Document Type: Article

References (27)

1. Hoffmann, D. and Hecht, S.S. (1985) Nicotine-derived iV-nitrosamirtes 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. International Agency for Research on Cancer (1985) Evaluation of the carcinogenic risk of chemicals to humans: tobacco habits other than smoking; betel quid and areca nut chewing; and some related nitrosamines. IARC Monogr., 37, 209-224
4. Hect, S.S., Young, R. and Chen, C.B. (1980) Metabolism in the F344 rat of 4-(N-methyl-A'-nitrosamino)-1 -(3-pyridyl)-1 -butanone, a tobacco-specific carcinogen. Cancer Res., 40, 4144-4150
5. Hoffmann, D., Castonguay, A., Rivenson, A. and Hecht, S.S. (1981) Comparative carcinogenicity and metabolism of 4-(methylnitrosamino)-1 -(3-pyridyl)-l-butanone and N'-nhrosonomicotine in Syrian golden hamsters. Cancer Res., 41, 2386-2393
6. McKennis, H. Jr., Schwartz, S.L., Turnbull, L.B., Tamaki, E. and Bowman, E.R. (1964) The metabolic formation of gamma-(3-pyridyl)-gamma-hydroxybutyric acid and its possible intermediary role in the mammalian metabolism of nicotine. J. Biol. Chem., 239, 3981-3989
7. Hecht, S.S., Lin, D. and Castonguay, A. (1983) Effects of a-deuterium substitution on the mutagenicity of 4-(methylnitrosamino)-1 -(3-pyridyl)-1 -butanone (NNK) Carcinogenesis, 4, 305-310
8. Gallice, P., Monti, J.P., Crevat, A., Durand, C. and Muriasco, A. (1985) A compound from uremic plasma and from normal urine isolated by liquid chromatography and identified by nuclear magnetic resonance Clin. Chem., 31, 30-34
9. Monti, J.P., Gallic, P., Crevat, A. and Munasco, A. (1985) Identification by nuclear magnetic resonance and mass spectrometry of glucuronic acid conjugate of o-hydroxybenzoic acid in normal urine and uremic plasma. Clin. Chem., 31, 1640-1643
10. Morse, M.A., Amin, S.G., Hecht, S.S. and Chung, F.-L. (1989) Effects of aromatic isothiocyanales on tumongenicity, (Amethylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-l-(3-py-ridyl)-1 -butanone in A/J mouse lung. Cancer Res., 49, 2894-2897
11. Morse, M.A., Eklind, K I., Amin, S.G., Hecht, S.S and Chung, F.-L. (1989) Effects of alkyl chain length on the inhibition of NNK-induced lung neoplasia in A/J mice by arylalkyl isothiocyanates. Carcinogenesis, 10, 1757-1759
12. Fischer, S., Spiegelhalder, B. and Preussmann, R. (1989) Tobacco-specific nitrosamines in mainstream smoke of West German cigarettes-tar alone is not a sufficient index for the carcinogenic potential of cigarette smoke. Carcinogenesis, 10, 169-173
13. Morse, M.A., Wang, C.-X., Stoner, G.D., Mandal, S, Conran, P.B., Amin, S.G., Hecht, S.S. and Chung, F.-L. (1989) Inhibition of 4-(methylnitro-sarruno)-1 -(3-pyndyl)-1 -butanone-induced DNA adduct formation and tumongenicity in the lung of F344 rats by dietary phenethyl isothiocyanate Cancer Res., 49, 549-553
14. Suzuki, E. and Okada, M. (1980) Metabolic fate of /V-butyl-A'-f4-hydroxy-butyl nitrosamine in the rat Gann, 71, 856-862
15. Suzuki, E. and Okada, M. (1980) Metabolic fate of (VW-dibutylnitrosamine in the rat. Gann, 71, 863-870
16. Suzuki, E., Aoki, J. and Okada, M. (1981) Metabolic fate of iV-butyl-iV-(4-hydroxybutyl)nitrosamine and A.N-dibutylnitrosamine in the guinea pig, with reference to their carcinogenic effects on the unnary bladder. Gann, 72, 547-551
17. Suzuki, E. and Okada, M. (1981) Metabolic fate of iV.iV-dipropylnitrosamine and iV.A'-diamylnitrosaminc in the rat, in relation to their lack of carcinogenic effect on the urinary bladder. Gann, 72, 552-561
18. Kokkinakis, D.M., Hollenberg, P.F. and Scarpelli, D.G. (1985) Major unnary metabolites in hamsters and rats treated with A-nitroso(2-hydroxypropyl) (2-oxo-propyl)amine. Cancer Res., 45, 3586-3592
19. Wiessler, M., Rossnagel, G. and Rugewitz-BlackhoIm, B. (1984) Conjugates of N-nitroso-ien-burylmethylamine in urine. IARC Scientific Publication no. 57. IARC, Lyon, pp. 465-471
20. Wiessler, M. and Rossnagel, G. (1987) a-Glucuronides of N-nitroso-methylbenzylamine. IARC Scientific Publication no. 84 IARC, Lyon, pp. 170-172
21. Hecht, S.S., Lin, D. and Chen, C.B. (1981) Comprehensive analysis of unnary metabolites of N'-nitrosonomicotmc. Carcinogenesis, 2, 833-838
22. Belinsky, S.A., White, C M., Trushin, N and Hecht, S.S. (1989) Cell specificity in the pulmonary metabolism of tobacco-specific nitrosamines in the Fischer rat. Carcinogenesis, 10, 2269-2274
23. Bryant, M.S., Skipper, P.L., Tannenbaum, S.R. and Maclure, M. (1987) Hemoglobin adducts of 4-aminobiphenyl in smokers and nonsmokers. Cancer Res., 47, 602-608
24. Bryant, M.S., Vineis, P., Skipper, P.L. and Tannenbaum, S.R. (1988) Hemoglobin adducts of aromatic amines: Associations with smoking status and type of tobacco. Proc. Natl. Acad. Sci. USA, 85, 9788-9791
25. Machine, M., Bryant, M.S., Skipper, P.L. and Tannenbaum, S.R. (1990) Decline of the hemoglobin adduct of 4-amtnophenyl during withdrawal from smoking. Cancer Res., 50, 181-184
26. 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-pyndyl)-1 -butanol in F344 rats. Carcinogenesis, 9, 1665-1668
27. Carmella, S.G., Kagan, S.S., Kagan, M., Foiles, P.G. and Hecht, S S. (1990) Hemoglobin adducts of tobacco-specific nitrosamines in smokers and snuff-dippers. Proc. Am. Assoc. Cancer Res., 31, 100