Enzymes involved in the bioactivation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in patas monkey lung and liver microsomes

Carcinogenesis

Volumn 18, Issue 8, 1997, Pages 1577-1584

  Smith, Theresa J ^a   Liao, Anita M ^a   Liu, Yuan ^a   Jones, Ann Butler ^b   Anderson, Lucy M ^b   Yang, Chung S ^a  

^a RUTGERS UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE; ACETYLSALICYLIC ACID; ALPHA NAPHTHOFLAVONE; CARBON MONOXIDE; COUMARIN; NORDIHYDROGUAIARETIC ACID; PHENETHYL ISOTHIOCYANATE;

ANIMAL MODEL; ARTICLE; FEMALE; IMMUNOBLOTTING; LIVER METABOLISM; LIVER MICROSOME; LUNG; METABOLISM; MICROSOME; MONKEY; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ASPIRIN; BIOTRANSFORMATION; CARBON MONOXIDE; COUMARINS; CYTOCHROME P-450 ENZYME SYSTEM; ERYTHROCEBUS PATAS; FEMALE; ISOTHIOCYANATES; LIPOXYGENASE; LUNG; MICROSOMES; MICROSOMES, LIVER; NITROSAMINES; NORDIHYDROGUAIARETIC ACID; OXYGENASES; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES;

EID: 0031418681     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/18.8.1577     Document Type: Article

References (36)

1. Hecht, S.S., Castonguay, A., Rivenson, A., Mu, B. and Hoffmann, D. (1983) Tobacco specific nitrosamines: carcinogenicity, metabolism, and possible role in human cancer. J. Environ. Sci. Health, C1, 1-54.
2. Hecht, S.S. (1994) Metabolic activation and detoxification of tobacco-specific nitrosamines - a model for cancer prevention strategies. Drug Metab. Rev., 26, 373-390.
3. 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.
4. 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.
5. Smith, T.J., Guo, Z.-Y., Thomas, P.E., Chung, F.-L., Morse, M.A., Eklind, 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.
6. Smith, T.J., Guo, Z., Hong, J.-Y., Ning, S.M., Thomas, P.E. and Yang, C.S. (1992) Kinetics and enzyme involvement in the metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in microsomes of rat lung and nasal mucosa. Carcinogenesis, 13, 1409-1414.
7. 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 (NNK) bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Res., 53, 3276-3282.
8. Jorquera, R., Castonguay, A. and Schuller, H.M. (1993) Effect of tobacco smoke condensate on the metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by adult and fetal hamster microsomes. Drug. Metab. Dispos., 21, 318-324.
9. Hecht, S.S., Trushin, N., Reid-Quinn, C.A., Burak, E.S., Jones, A.B., Southers, J.L., Gombar, C.T., Carmella, S.G., Anderson, L.M. and Rice, J.M. (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.
10. Castonguay, A., Tjalve, H., Trushin, N., d'Argy, R. and Sperber, G. (1985) Metabolism and tissue distribution of tobacco-specific N-nitrosamines in the marmoset monkey (Callithrixjacchus). Carcinogenesis, 6, 1543-1550.
11. Smith, T.J., Guo, Z., Gonzalez, F.J., Guengerich, F.P., Stoner, G.D. and Yang, C.S. (1992) Metabolism of 4-(methylnitrosamino)-1-(3-pyridyI)-1-butanone in human lung and liver microsomes and cytochromes P-450 expressed in hepatoma cells. Cancer Res., 52, 1757-1763.
12. 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 P450, lipoxygenase, and hydroperoxides. Cancer Res., 55, 5566-5573.
13. Castonguay, A., Stoner, G.D., Schut, H.A. and Hecht, S.S. (1983) Metabolism of tobacco-specific N-nitrosamines by cultured human tissues. Proc. Natl Acad. Sci. USA, 80, 6694-6697.
14. 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.
15. 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.
16. Murphy, S.E., Carmella, S.G., Idris, A.M. and Hoffmann, D. (1994) Uptake and metabolism of carcinogenic levels of tobacco-specific nitrosamines by sudanese snuff dippers. Cancer Epidem. Biomark. Prev., 3, 423-428.
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. Guo, Z., Smith, T.J., Thomas, P.E. and Yang, C.S. (1992) Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by inducible and constitutive cytochrome P450 enzymes in rats. Arch. Biochem. Biophys., 298, 279-286.
19. Patten, C.J., Smith, T.J., Murphy, S.E., Wang, M.-H., Lee, J., Tynes, R.E., Koch, P. and Yang, C.S. (1996) Kinetic analysis of activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by heterologously expressed human P450 enzymes and the effect of P450 specific chemical inhibitors on this activation in human liver microsomes. Arch. Biochem. Biophys., 333, 127-138.
20. Crespi, C.L., Penman, B.W., Gelboin, H.V. and Gonzalez, F.J. (1991) A tobacco smoke-derived nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, is activated by multiple human cytochrome P450s including the polymorphic human cytochrome P4502D6. Carcinogenesis, 12, 1197-1201.
21. Weitberg, A. and Corvese, D. (1993) Oxygen radicals potentiate the genetic toxicity of tobacco-specific nitrosamines. Clin. Genet., 43, 88-91.
22. Kim, P.M. and Wells, P.G. (1996) Genoprotection by UDP-glucuronosyltransferases in peroxidase-dependent, reactive oxygen species-mediated micronucleus initiation by the carcinogens 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and benzo[a]pyrene. Cancer Res., 56, 1526-1532.
23. 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.
24. Lowry, O.H., Rosebrough, N.J., Farr, A.L. and Randall, R.J. (1951) Protein measurement with the Polin phenol reagent. J. Biol. Chem., 193, 265-275.
25. Yun, C.-H., Shimada, T. and Guengerich, F.P. (1991) Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol. Pharmacol., 40, 679-685.
26. Halpert, J.R., Guengerich, F.P., Bend, J.R. and Correia, M.A. (1994) Contemporary issues in toxicology. Selective inhibitors of cytochromes P450. Toxicol. Appl. Pharmacol., 125, 163-175.
27. Chang, T.K.H., Gonzalez, F.J. and Waxman, D.J. (1994) Evaluation of triacetyloleandomycin, α-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochrome P450. Arch. Biochem. Biophys., 311, 437-442.
28. Waxman, D.J., Lapenson, D.P., Aoyama, T., Gelboin, H.V., Gonzalez, F.J. and Korzekwa, K. (1991) Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s. Arch. Biochem. Biophys., 290, 160-166.
29. Yamano, S., Tatsuno, J. and Gonzalez, F.J. (1990) The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochem., 29, 1322-1329.
30. Miles, J.S., McLaren, A.W., Forrester, L.M., Glancey, M.J., Lang, M.A. and Wolf, C.R. (1990) Identification of the human liver cytochrome P-450 responsible for coumarin 7-hydroxylase activity. Biochem. J., 267, 365-371.
31. Smith, T.J., Guo, Z., Guengerich, F.P. and Yang, C.S. (1996) Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by human cytochrome P450 1A2 and its inhibition by phenethyl isothiocyanate. Carcinogenesis, 17, 809-813.
32. Sadrieh, N. and Snyderwine, E.G. (1995) Cytochromes P450 in cynomolgus monkeys mutagenically activate 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) but not 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx). Carcinogenesis, 16, 1549-1555.
33. 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.
34. 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.
35. 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 the lung of F344 rats by dietary phenethyl isothiocyanate. Cancer Res., 49, 549-553.
36. Hecht, S.S., Trushin, N., Rigotty, J., Carmella, S.G., Borukhova, A., Akerkar, S. and Rivenson, A. (1996) Complete inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced rat lung tumorigenesis and favorable modification of biomarkers by phenethyl isothiocyanate. Cancer Epidemiol. Biomark. Prev., 5, 645-652.