Metabolism of N-nitrosobenzylmethylamine by human cytochrome p-450 enzymes

Journal of Toxicology and Environmental Health - Part A

Volumn 58, Issue 7, 1999, Pages 397-411

  Morse, Mark A ^a   Lu, Jerry ^a   Stoner, Gary D ^a   Murphy, Sharon E ^b   Peterson, Lisa A ^c  

^a OHIO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; BENZOIC ACID; BENZYL ALCOHOL; CARCINOGEN; CHLORZOXAZONE; COUMARIN; COUMARIN DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 2A6; DIMETHYLNITROSAMINE DEMETHYLASE; ETHOXYRESORUFIN; ISOTHIOCYANIC ACID DERIVATIVE; MEPHENYTOIN; METHOXSALEN; N BENZYL N METHYLNITROSAMINE; NIFEDIPINE; OXYGENASE; UNCLASSIFIED DRUG;

ARTICLE; CHINA; CONTROLLED STUDY; ENZYME ACTIVITY; ESOPHAGUS CANCER; FOOD CONTAMINATION; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROXYLATION; LIVER MICROSOME; LYMPHOBLASTOID CELL LINE; METABOLISM; METABOLITE; MICROSOME; PRIORITY JOURNAL; RADIATION DETECTION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

BENZYLAMINES; CELL LINE; CYTOCHROME P-450 ENZYME SYSTEM; ESOPHAGEAL NEOPLASMS; FOOD CONTAMINATION; HUMANS; LIVER; MICROSOMES;

EID: 0033544905     PISSN: 15287394     EISSN: 10872620     Source Type: Journal    
DOI: 10.1080/009841099157133     Document Type: Article

References (29)

1. Autrup, H., and Stoner, G. D. 1982. Metabolism of N-nitrosamines by cultured human and rat esophagus. Cancer Res. 42:1307-1311.
2. Camus, A. M., Geneste, O., Honkakoski, P., Bereziat, J. C., Henderson, C. J., Wolf, C. R., Bartsch, H., and Lang, M. A. 1993. High variability of nitrosamine metabolism among individuals: Role of cytochromes P450 2A6 and 2E1 in the dealkylation of N-nitrosodimethylamine and N-nitrosodi-ethylamine i n mice and humans. Mol. Carcinogen. 7:268-275.
3. Daniel, E. M., and Stoner, G. D. 1991. The effects of ellagic acid and 13-cis-retinoic acid on N-nitrosobenzylmethylamine-induced esophageal tumorigenesis i n rats. Cancer Lett. 56:117-124.
4. Gopalakrishnan, R., Morse, M. A., Lu, J., Weghorst, C. M., Sabourin, C. L. K., Stoner, G. D., and Murphy, S. E. 1999. Expression of cytochrome P450 2A3 in rat esophagus: Relevance to N-nitrosobenzylmethylamine. Carcinogenesis 20:885-891.
5. Guengerich, F. P. 1989. Analysis and characterization of enzymes. In Principles and methods of toxicology, 2nd ed., ed. W. Hayes, pp. 777-814. New York: Raven Press Ltd.
6. Hakkola, J., Pasanen, M., Purkunen, R., Saarikoski, S., Pelkonen, O., Maenpaa, J., Rane, A., and Raunio, H. 1994. Expression of xenobiotic-metabolizing cytochrome P450 forms in human adult and fetal liver. Biochem. Pharmacol. 48:59-64.
7. Ji, C., and Li, M. 1991. Studies of pickled vegetables and cause of esophageal cancer in Linxian. II. Determination of nitrosamines and their precursors. Chung-Kuo I Hsueh Ko Hsueh Yuan Pao Acta Acad. Med. Sin. 13:320-232.
8. Mandal, S., and Stoner, G. D. 1990. Inhibition of N-nitrosobenzylmethylamine-induced esophageal tumorigenesis i n rats by ellagic acid. Carcinogenesis 11:55-61.
9. Morse, M. A., and Lu, J. 1998. An HPLC method for measurement of cytochrome P450-mediated metabolism of 7-ethoxy-4-trifluoromethylcoumarin. J. Chromatogr. 708:290-293.
10. Morse, M. A., LaGreca, S. D., Amin, S. G., and Chung, F.-L. 1990. Effects of indole-3-carbinol on lung tumorigenesis and DNA methylation induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), and on the metabolism and disposition of NNK in A/J Mice. Cancer Res. 50:2613-2617.
11. Morse, M. A., Eklind, K. I., Hecht, S. S., Jordan, K. G., Choi, C.-I., Desai, D. H., Amin, S. G., and Chung, F.-L. 1991. Structure-activity relationships for inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) lung tumorigenesis by arylalkyl isothiocyanates in A/J mice. Cancer Res. 51 :1846-1850.
12. Morse, M. A., Zu, H., Galati, A. J., Schmidt, C. J., and Stoner, G. D. 1993. Dose-related inhibition by dietary phenethyl i sothiocyanate of esophageal tumorigenesis and DNA methylation i nduced by N-nitrosobenzylmethylamine i n rats. Cancer Lett. 72:103-110.
13. Nesnow, S., Beck, S., Rosenblum, S., Lasley, J., Tiano, H. F., Hosokawa, M., Crespi, C. L., and Langenbach, R. 1994. N-Nitrosodiethylamine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone induced morphological transformation of C3H/10T1/2CL8 cells expressing human cytochrome P4502A6. Mutat. Res. 324:93-102.
14. Patten, C. J., Ishizaki, H., Aoyama, T., Lee, M., Ning, S. M., Hunag, W., Gonzales, F. J., and Yang, C. S. 1992. Catalytic properties of the human cytochrome P450 2E1 produced by cDNA expression in mammalian cells. Arch. Biochem. Biophys. 299:163-171.
15. Patten, C. J., Smith, T. J., Friesen, M. J., Tynes, R. E., Yang, C. S., and Murphy, S. E. 1997. Evidence for cytochrome P450 2A6 and 3A4 as major catalysts for N'-nitrosonornicotine a-hydroxylation by human liver microsomes. Carcinogenesis 18:1623-1630.
16. Peter, R., Bocker, R., Beanue, P. H., Iwasaki, M., Guengerich, F. P., and Yang, C. S. 1990. Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chem. Res. Toxicol. 3:566-573.
17. Peterson, L. A. 1997. N-Nitrosobenzylmethylamine i s activated to a DNA benzylating agent in rats. Chem. Res. Toxicol. 10:19-26.
18. Rosenberg, D. W., Roque, H., and Kappas, A. 1990. A fluorometric method for measuring ethoxy-coumarin O-deethylase activity by reversed-phase HPLC. Anal. Biochem. 191:354-358.
19. Singer, G. M., Chuna, J., Roman, J., Min-Hsin, L., and Lijinsky, W. 1986. Nitrosamines and nitros-amine precursors in foods from Linxian, China, a high incidence area for esophageal cancer. Carcinogenesis 7:733-736.
20. Smith, T. J., Liao, A., Wang, L.-D., Yang, G., Starcic, S., Philbert, M. A., and Yang, C. S. 1998. Characterization of xenobiotic-metabolizing enzymes and nitrosamine metabolism in the human esophagus. Carcinogenesis 19:667-672.
21. Stoner, G. D., Morrissey, D. T., Heur, Y.-H., Daniel, E. M., Galati, A. J., and Wagner, S. W. 1991. Inhibitory effects of phenethyl i sothiocyanate on N-nitrosobenzylmethylamine carcinogenesis in the rat esophagus. Cancer Res. 51 :2063-2068.
22. Stoner, G. D., Siglin, J. C., Morse, M. A., Desai, D. H., Amin, S. G., Kresty, L. A., Toburen, A. L., Heffner, E. M., and Francis, D. J. 1995. Enhancement of esophageal carcinogenesis in male F344 rats by dietary phenylhexyl i sothiocyanate. Carcinogenesis 16:2473-2476.
23. Su, T., Sheng, J. J., Lipinskas, T. W., and Ding, X. 1996. Expression of CYP2A genes in rodent and human nasal mucosa. Drug Metab. Dispos. 24:884-890.
24. Tanaka, M., Kato, K., Sudo, K., Hakusui, H., Ohkubo, T., Sugawara, K., Kaneko, S., Otani, K., Chiba, K., and Ishizaki, T. 1996. Simple and selective assay of 4-hydroxymephenytoin i n human urine using solid-phase extraction and high-performance liquid chromatography with electrochemical detection and its preliminary application to phenotyping test. J. Chromatogr. B Biomed. Appl. 676: 87-94.
25. Tiano, H. F., Wang, R. L., Hosokawa, M., Crespi, C., Tindall, K. R., and Langenbach, R. 1994. Human CYP2A6 activation of 4-(methylnitrosamino)-1-(3-pyidyl)-1-butanone (NNK): mutational specificity i n the gpt gene of AS52 cells. Carcinogenesis 15:2859-2866.
26. Wargovich, M. J., Woods, C., Eng, V. W. S., Stephens, L. C., and Gray, K. 1988. Chemoprevention of N-nitrosobenzylmethylamine-induced esophageal cancer in rats by the naturally occurring thioether, diallyl sulfide. Cancer Res. 48:6872-6875.
27. Wilkinson, J. T., Morse, M. A., Kresty, L. A., and Stoner, G. D. 1995. Effect of alkyl chain length on inhibition of N-nitrosobenzylmethylamine-induced esophageal tumorigenesis and DNA methylation by isothiocyanates. Carcinogenesis 16:1011-1015.
28. Yamazaki, H., Inui, Y., Yun, C. H., Guengerich, F. P., and Shimada, T. 1992. Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines i n human liver microsomes. Carcinogenesis 13:1789-1794.
29. Yang, C. S., Smith, T. J., Hong, J.-Y., and Zhou, S. 1994. Kinetics and enzymes involved in the metabolism of nitrosamines. In Nitrosamines and related N-nitroso compounds: Chemistry and biochemistry, Vol. 553, eds. R. N. Loeppky and C. J. Michejda, pp. 169-178. Washington, D.C.: ACS Symposium Series.