Evidence for an important role of DNA pyridyloxobutylation in rat lung carcinogenesis by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone: Effects of dose and phenethyl isothiocyanate

Cancer Research

Volumn 57, Issue 2, 1997, Pages 259-266

  Staretz, Marianne E ^a   Foiles, Peter G ^a,b   Miglietta, Lisa M ^a,b   Hecht, Stephen S ^a,c  

^a AMERICAN HEALTH FOUNDATION   (United States)

^b Alteon Inc   (United States)

^c UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE; PHENETHYL ISOTHIOCYANATE;

ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CHEMICAL CARCINOGENESIS; CLARA CELL; CONTROLLED STUDY; DIET; DNA ADDUCT; LUNG CANCER; LUNG CARCINOGENESIS; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; SMOKING;

ANIMALS; ANTICARCINOGENIC AGENTS; CARCINOGENS; DEOXYGUANOSINE; DNA ADDUCTS; DOSE-RESPONSE RELATIONSHIP, DRUG; ISOTHIOCYANATES; LUNG; LUNG NEOPLASMS; MALE; NEOPLASMS, EXPERIMENTAL; NITROSAMINES; RATS; RATS, INBRED F344;

EID: 0031023711     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. 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
2. Hoffmann, D., and Hecht, S. S. Nicotine-derived N-nitrosamines and tobacco-related cancer: current status and future directions. Cancer Res., 45: 935-444, 1985.
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. Recent studies on mechanisms of bioactivation and detoxification of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a tobacco-specific lung carcinogen. CRC Crit. Rev. Toxicol., 26: 163-181, 1996.
5. Hecht, S. S. Metabolic activation and detoxification of tobacco-specific nitrosamines: a model for cancer prevention strategies. Drug Metab. Rev., 26: 373-390, 1994.
6. 6-methylguanine built into a unique site in a viral genome. Proc. Natl. Acad. Sci. USA. 81: 6271-6275, 1984.
7. Hecht, S. S., Jordan, K. G., Choi, C-I., and Trushin, N. Effects of deuterium substitution on the tumorigenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-(3-pyridyl)-1-butanol in A/J mice. Carcinogenesis (Lond.), 11: 1017-1020, 1990.
8. 6-Methylguanine is a critical determinant of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone tumorigenesis in A/J mouse lung. Cancer Res., 51: 5557-5564, 1991.
9. Belinsky, S. A., Devereux, T. R., Maronpot, R. R., Stoner, G. D., and Anderson, M. W. The relationship between the formation of promutagenic adducts and the activation of the K-ras proto-oncogene in lung tumors from A/J mice treated with nitrosamines. Cancer Res., 49: 5305-5311, 1989.
10. 6-methylguanine formation in Clara cells and induction of pulmonary neoplasia in the rat by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res., 50: 3772-3780, 1990.
11. Hecht, S. S., Peterson, L. A., and Spratt, T. E. Tobacco-specific nitrosamines. In: K. Hemminki, A. Dipple, D. E. G. Shuker, F. F. Kadlubar, D. Segerbäck, and H. Bartsch (eds.), DNA Adducts: Identification and Biological Significance IARC Scientific Publications. Vol. 125. pp. 91-106. Lyon, France: IARC, 1994.
12. Breeze, R. J., and Wheeldon, E. B. The cells of the pulmonary airways. Am. Rev. Resp. Disease. 116: 705-777, 1977.
13. Devereux, T. R., Domin, B. A., and Philpot, R. M. Xenobiotic metabolism by isolated pulmonary bronchiolar and alveolar cells. In: T. E. Gram (ed.), Metabolic Activation and Toxicity of Chemical Agents to Lung Tissue and Cells, pp. 25-40. New York: Pergamon Press, 1993.
14. Bond, J. Metabolism of xenobiotics by the respiratory tract. In: D. E. Gardner, J. D. Crapo, and R. O. McClellan (eds.), Toxicology of the Lung, Ed. 2, pp. 187-215. New York: Raven Press, Ltd., 1993.
15. Belinsky, S. A., White, C. M., Devereux, T. R., Swenberg, J. A., and Anderson, M. W. Cell-selective alkylation of DNA in rat lung following low dose exposure to the tobacco specific carcinogen 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res., 47: 1143-1148, 1987.
16. 6methylguanine in rat pulmonary cells. Carcinogenesis (Lond.), 9: 2053-2058, 1988.
17. Devereux, T. R., Anderson, M. W., and Belinsky, S. A. Factors regulating activation and DNA alkylation by 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone and nitrosodimethylamine in rat lung and isolated lung cells, and their relationship to carcinogenicity. Cancer Res., 48: 4215-4221, 1988.
18. Hecht, S. S., Lin, D., Castonguay, A., and Rivenson, A. Effects of α-deuterium substitution on the tumorigenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in F344 rats. Carcinogenesis (Lond.), 8: 291-294, 1987.
19. Hecht, S. S., Lin, D., and Castonguay, A. Effects of α-deuterium substitution on the mutagenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Carcinogenesis (Lond.), 4: 305-310, 1983.
20. Foiles, P. G., Peterson, L. A., Miglietta, L. M., and Ronai, Z. Analysis of mutagenic activity and ability to induce replication of polyoma DNA sequences by different model compounds of the carcinogenic tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Mutat. Res., 279: 91-101, 1992.
21. 6-methylguanine. Cancer Res., 53: 2780-2785, 1993.
22. Hecht, S. S. Chemoprevention by isothiocyanates. J. Cell. Biochem. Suppl., 22: 195-209, 1995.
23. Morse, M. A., Wang, C-X., Stoner, G. D., Mandal, S., Conran, P. B., Amin, S. G., Hecht, S. S., and Chung, F-L. Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA adduct formation and tumorigenicity in lung of F344 rats by dietary phenethyl isothiocyanate. Cancer Res., 49: 549-553, 1989.
24. Smith, T. J., Guo, Z., Thomas, P. E., Chung, F-L., Morse, M. A., Eklind, K., and Yang, C. S. Metabolism of 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone in mouse lung microsomes and its inhibition by isothiocyanates. Cancer Res., 50: 6817-6822, 1990.
25. Guo, Z., Smith, T. J., Thomas, P. E., and Yang, C. S. Metabolic activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone as measured by DNA alkylation in vitro and its inhibition by isothiocyanates. Cancer Res., 51: 4798-4803, 1991.
26. Guo, Z., Smith, T. J., Wang, E., Eklind, K. I., Chung, F-L., and Yang, C. S. Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis (Lond.), 14: 1167-1173, 1993.
27. Doerr-O'Rourke, K., Trushin, N., Hecht, S. S., and Stoner, G. D. Effect of phenethyl isothiocyanate on the metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by cultured rat lung tissue. Carcinogenesis (Lond.), 12: 1029-1034, 1991.
28. Staretz, M. E., and Hecht, S. S. Effects of phenethyl isothiocyanate on the tissue distribution of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and metabolites in F344 rats. Cancer Res., 55: 5580-5588, 1995.
29. 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 nonsmokers. Chem. Res. Toxicol., 4: 364-368, 1991.
30. Hecht, S. S., Trushin, N., Castonguay, A., and Rivenson, A. Comparative tumorigenicity and DNA methylation in F344 rats by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N-nitrosodimethylamine. Cancer Res., 46: 498-502, 1986.
31. 6-methyldeoxyguanosine in human placental DNA. Cancer Res., 48: 4184-4188, 1988.
32. Crain, P. F. Preparation and enzymatic hydrolysis of DNA and RNA for mass spectrometry. In: J. A. McCloskey (ed.), Methods in Enzymology, Vol. 193, pp. 782-790. San Diego, CA: Academic Press, 1990.
33. Smith, T. J., Guo, Z., Thomas, P. E., and Yang, C. S. Kinetics and enzyme involvement in the metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by rat lung and nasal mucosa. Carcinogenesis (Lond.), 13: 1409-1414, 1992.
34. Belinsky, S. A., White, C. M., Trushin, N., and Hecht, S. S. Cell specificity for the pulmonary metabolism of tobacco-specific nitrosamines in the Fischer rat. Carcinogenesis (Lond.), 10: 2269-2274, 1989.
35. Murphy, S. E., Palomino, A., Hecht, S. S., and Hoffmann, D. Dose-response study of DNA and hemoglobin adduct formation by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in F344 rats. Cancer Res., 50: 5446-5452, 1990.
36. Crystal, R. G. Alveolar macrophages. In: R. G. Crystal and J. B. West (eds.), The Lung, pp. 527-538. New York: Raven Press, 1991.
37. Takemura, R., and Werb, Z. Secretory products of macrophages and their physiological functions. Am. J. Physiol., 246: C1-C9, 1984.
38. Schoenfeld, W., Schluter, B., Hilger, R., and Konig, W. Leukotriene generation and metabolism in isolated human lung macrophages. Immunology, 65: 529-536, 1988.
39. Smith, T. J., Stoner, G. D., and Yang, C. S. Activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung microsomes by cytochromes P450, lipoxygenase, and hydroperoxides. Cancer Res., 55: 5566-5573, 1995.
40. DeFlora, S., Izzotti, A., D'Agostini, F., Rossi, G. A., and Balansky, R. M. Pulmonary alveolar macrophages in molecular epidemiology and chemoprevention of cancer. Environ. Health Perspect., 99: 249-252, 1993.