Effects of long term dietary phenethyl isothiocyanate on the microsomal metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F344 rats

Carcinogenesis

Volumn 18, Issue 9, 1997, Pages 1715-1722

  Staretz, Marianne E ^a   Koenig, LeeAnn A ^a   Hecht, Stephen S ^a,b  

^a AMERICAN HEALTH FOUNDATION   (United States)

^b 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; CARCINOGEN; PHENETHYL ISOTHIOCYANATE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DIET; HYDROXYLATION; LIVER MICROSOME METABOLISM; LUNG; LUNG CARCINOGENESIS; MALE; METABOLIC ACTIVATION; METABOLISM; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; RAT;

ANIMALS; ANTICARCINOGENIC AGENTS; DIET; GLUCURONATES; ISOTHIOCYANATES; LUNG; MALE; MICROSOMES; MICROSOMES, LIVER; NITROSAMINES; RATS; RATS, INBRED F344;

EID: 0031431664     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/18.9.1715     Document Type: Article

References (49)

1. Hecht, S.S. and Hoffmann, D. (1988) Tobacco-specific nitrosamines, an important group of carcinogens in tobacco and tobacco smoke. Carcinogenesis, 9, 875-884.
2. Hecht, S.S. and Hoffmann, D. (1989) The relevance of tobacco-specific nitrosamines to human cancer. Cancer Surv., 8, 273-294.
3. Hecht, S.S. (1996) 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.
4. Hecht, S.S. (1994) Metabolic activation and detoxification of tobacco-specific nitrosamines - a model for cancer prevention strategies. Drug Metab. Rev., 26, 373-390.
5. 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.
6. Rivenson, A., Hoffmann, D., Prokopczyk, B., Amin, S. and Hecht, S.S. (1988) Induction of lung and exocrine pancreas tumors in F344 rats by tobacco-specific and Areca-derived N-nitrosamines. Cancer Res., 48, 6912-6917.
7. Hoffmann, D., Rivenson, A., Abbi, R. and Wynder, E. (1993) A study of tobacco carcinogenesis: effect of the fat content of the diet on the carcinogenic activity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in F344 rats. Cancer Res., 53, 2758-2761.
8. 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.
9. 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.
10. Belinsky, S.A., White, C.M., Trushin, N. and Hecht, S.S. (1989) Cell specificity for the pulmonary metabolism of tobacco-specific nitrosamines in the Fischer rat. Carcinogenesis, 10, 2269-2274.
11. 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.
12. Doerr-O'Rourke, K., Trushin, N., Hecht, S.S. and Stoner, G.D. (1991) 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, 12, 1029-1034.
13. Castonguay, A., Tjälve, H., Trushin, N. and Hecht, S.S. (1984) Perinatal metabolism of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in C57B1 mice. J. Natl Cancer Inst., 72, 1117-1126.
14. Hong, J.-Y., Wang, Z.Y., Smith, T.J., Zhou, S., Shi, S., Pan, J. and Yang, C.S. (1992) Inhibitory effects of diallyl sulfide on the metabolism and tumorigenicity of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in A/J mouse lung. Carcinogenesis, 13, 901-904.
15. Murphy, S.E. and Coletta, K.A. (1993) Two types of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone hemoglobin adducts, from metabolites which migrate into or are formed in red blood cells. Cancer Res., 53, 777-783.
16. Murphy, S.E., Spina, D.A., Nunes, M.G. and Pullo, D.A. (1995) Glucuronidation of 4-(hydroxymethyl)nitrosamino-1-(3-pyridyl)-1-butanone, a metabolically activated form of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, by phenobarbital treated rats. Chem. Res. Toxicol., 8, 772-779.
17. 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.
18. Hecht, S.S., Trushin, N., Reid-Quinn, C.A. et al. (1993) Metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in the Patas monkey: pharmacokinetics and characterization of glucuronide metabolites. Carcinogenesis, 14, 229-236.
19. Staretz, M.E. and Hecht, S.S. (1995) 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.
20. Steinmetz, K.A. and Potter, J.D. (1991) Vegetables, fruit, and cancer. II. Mechanisms. Cancer Causes Control, 2, 427-442.
21. Kelloff, G.J., Boone, C.W., Crowell, J.A., Steele, V.E., Lubet, R. and Sigman, C.C. (1994) Chemopreventive drug development: perspectives and progress. Cancer Epidem., Biomark. Prev., 3, 85-98.
22. Hecht, S.S. (1995) Chemoprevention by isothiocyanates. J. Cell. Biochem., 22(Suppl.), 195-209.
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. (1989) 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.
24. Hecht, S.S., Trushin, N., Rigotty, J., Carmella, S.G., Borukhava, A. and Akerkar, S. (1996) Complete inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone induced rat lung tumorigenesis and favorable modification of biomarkers by phenethyl isothiocyanate. Cancer Epidem., Biomark. Prev., 5, 645-652.
25. Morse, M.A., Eklind, K.I., Amin, S.G. and Chung, F.L. (1992) Effect of frequency of isothiocyanate administration on inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced pulmonary adenoma formation in A/J mice. Cancer Lett., 62, 77-81.
26. 6-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung. Cancer Res., 49, 2894-2897.
27. Yang, C.S., Smith, T.J. and Hong, J.-Y. (1994) Cytochrome P-450 enzymes as targets for chemoprevention against chemical carcinogenesis and toxicity: opportunities and limitations. Cancer Res., 54, 1982s-1986s.
28. Smith, T.J., Guo, Z.Y., Thomas, P.E., Chung, F.L., Morse, M.A., Elkind, K. and Yang, C.S. (1990) Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mouse lung microsomes and its inhibition by isothiocyanates Cancer Res., 50, 6817-6822.
29. Guo, Z., Smith, T.J., Thomas, P.E. and Yang, C.S. (1991) 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.
30. Guo, Z., Smith, T.J., Wang, E., Sadrieh, N., Ma, Q., Thomas, P.E. and Yang, C.S. (1992) Effects of phenethyl isothiocyanate, a carcinogenesis inhibitor, on xenobiotic-metabolizing enzymes and nitrosamine metabolism in rats. Carcinogenesis, 13, 2205-2210.
31. Guo, Z., Smith, T.J., Wang, E., Eklind, K.I., Chung, F.-L. and Yang, C.S. (1993) 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, 14, 1167-1173.
32. Smith, T.J., Guo, Z., Li, C., Ning, S.M., Thomas, P.E. and Yang, C.S. (1993) Mechanisms of inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Res., 53, 3276-3282.
33. Staretz, M.E., Foiles, P.G., Miglietta, L.M. and Hecht, S.S. (1997) 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 Res., 57, 259-266.
34. Zhang, Y. and Talalay, P. (1994) Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanism. Cancer Res., 54(Suppl.), 1976s-1981s.
35. 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.
36. Hecht, S.S., Chen, C.B., Dong, M., Ornaf, R.M., Hoffmann, D. and Tso, T.C. (1977) Studies on non-volatile nitrosamines in tobacco. Beitr. Tabakforsch., 9, 1-6.
37. 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.
38. Castonguay, A., Stoner, G.D., Schut, H.A.J. and Hecht, S.S. (1983) Metabolism of tobacco-specific N-nitrosamines by cultured human tissues. Proc. Natl Acad. Sci. USA, 80, 6694-6697.
39. Chen, C.B., Hecht, S.S. and Hoffmann, D. (1978) Metabolic α-hydroxylation of the tobacco specific carcinogen, N′-nitrosonornicotine. Cancer Res., 38, 3639-3645.
40. 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.
41. Guengerich, F.P. (1982) Microsomal enzymes involved in toxicology -analysis and separation. In Hates, A.W. (ed.) Principles and Methods of Toxicology. Raven Press, New York, pp. 609-634.
42. 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.
43. Peterson, L.A., Mathew, R. and Hecht, S.S. (1991) Quantitation of metabolic α-hydroxylation of the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res., 51, 5495-5500.
44. Wheatley, D.N., Inglis, M.S., Foster, M.A. and Rimington, J.E. (1987) Hydration, volume changes and nuclear magnetic resonance proton relaxation times of HeLA S-3 cells in M-phase and the subsequent cell cycle. J. Cell Sci., 88, 13-23.
45. Hoffman, D., Kumar, A.M., Spitzer, A. and Gupta, R.K. (1986) NMR measurement of intracellular water volume in kidney proximal tubules. Biochim. Biophys. Acta, 889, 355-360.
46. Smith, T.J., Stoner, G.D. and Yang, C.S. (1995) Activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung microsomes by cytochromes P540, lipoxygenase, and hydroperoxides. Cancer Res., 55, 5566-5573.
47. Guo, Z., Smith, T.J., Thomas, P.E. and Yang, C.S. (1992) Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by inducible and constitutive cytochrome P450 enzymes in rats. Arch. Biochem. Biophys., 298, 279-286.
48. 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.
49. Liu, L., Alaoui-Jamali, M.A., El Alami, N. and Castonguay, A. (1990) Metabolism and DNA single strand breaks induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and its analogues in primary culture of rat hepatocytes. Cancer Res., 50, 1810-1816.