N-Nitrosobenzylmethylamine is activated to a DNA benzylating agent in rats

Chemical Research in Toxicology

Volumn 10, Issue 1, 1997, Pages 19-26

  Peterson, Lisa A ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 N BENZYLADENINE; 6 O ALKYLGUANINE DNA ALKYLTRANSFERASE; 6 O BENZYLGUANINE; BENZYL ALCOHOL; BENZYL DERIVATIVE; DEOXYGUANOSINE; DNA; N BENZYL N METHYLNITROSAMINE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHEMICAL CARCINOGENESIS; CONTROLLED STUDY; DNA ADDUCT; DNA METHYLATION; ESOPHAGUS CANCER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIVER; LUNG PARENCHYMA; MALE; NONHUMAN; RAT;

ANIMALS; BIOTRANSFORMATION; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIMETHYLNITROSAMINE; DNA; DNA ADDUCTS; DNA METHYLATION; ESOPHAGUS; GASTRIC MUCOSA; HYDROLYSIS; LIVER; LUNG; MALE; NITROSOUREA COMPOUNDS; RATS; RATS, INBRED F344;

EID: 0031032861     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9601014     Document Type: Article

References (45)

1. Druckey, H., Preussmann, R., Ivankovic, S., and Schmähl, D. (1967) Organotrope carcinogene wirkung bei 65 verschiedenen N-nitrosoverbindungen an BD-ratten (Organotropic carcinogenic effects of 65 different N-nitroso compounds in BD rats). Z. Krebsforsch. 69, 103-201.
2. Stinson, S. F., Squire, R. A., and Sporn, M. B. (1978) Pathology of oesophageal neoplasms and associated proliferative lesions induced in rats by N-methyl-N-benzyl-nitrosamine. J. Natl. Cancer Inst. 61, 1471-1475.
3. Sander, J., and Schweinsberg, F. (1973) Tumorinduktion bei Mäusen durch N-Methylbenzyl-nitrosamin in niedriger Dosierung (Tumor induction in mice following low doses of methylbenzylnitrosamine). Z. Krebsforsch. 79, 157-161.
4. Yang, C. S. (1980) Research on esophageal cancer in China: a review. Cancer Res. 40, 2633-2644.
5. Lu, S., Chiu, S. X., Yang, W. X., Hu, X. N., Guo, L. P., and Li, F. M. (1991) Relevance of N-nitrosamines to oesophageal cancer in China. In Relevance to Human Cancer of N-Nitroso Compounds, Tobacco Smoke and Mycotoxins (O'Neill, I. K., Chen, J., and Bartsch, H., Eds.) pp 11-17, International Agency for Research on Cancer, Lyon, France.
6. Yoo, J.-S., Guengerich, F. P., and Yang, C. S. (1988) Metabolism of N-nitrosodialkylamines by human liver microsomes. Cancer Res. 48, 1499-1504.
7. Kraft, P. L., Skipper, P. L., and Tannenbaum, S. R. (1980) In vivo metabolism and whole-blood clearance of N-nitrosomethylbenzylamine in the rat. Cancer Res. 40, 2740-2742.
8. Hodgson, R. M., Wiessler, M., and Kleihues, P. (1980) Preferential methylation of target organ DNA by the oesophageal carcinogen N-nitrosomethylbenzylamine. Carcinogenesis 1, 861-866.
9. Hodgson, R. M., Schweinsberg, F., Wiessler, M., and Kleihues, P. (1982) Mechanism of esophageal tumor induction in rats by N-nitrosomethylbenzylamine and its ring-methylated analog N-nitrosomethyl(4-methylbenzyl)amine. Cancer Res. 42, 2836-2840.
10. Ludeke, B. I., Dominé, F., Ohgaki, H., and Kleihues, P. (1992) Modulation of N-nitrosomethylbenzylamine bioactivation by diallyl sulfide in vivo. Carcinogenesis 13, 2467-2470.
11. 6-alkylguanine shows tissue specific formation in and removal from esophageal and liver DNA in rats treated with methylbenzylnitrosamine, dimethylnitrosamine, diethylnitrosamine and ethylnitrosourea. Cancer Lett. 46, 21-29.
12. van Benthem, J., Wild. C. P., Vermeulen, E., den Engelse, L., and Scherer, E. (1991) Immunocytochemical localization of DNA adducts induced by a single dose of N-nitroso-N-methylbenzylamine in target and non-target tissues of tumor formation in the rat. Carcinogenesis 12, 1831-1837.
13. Barch, D. H., Jacoby, R. F., Brasitus, T. A., Radosevich, J. A., Carney, W. P., and Iannaccone, P. M. (1991) Incidence of Harvey ras oncogene point mutations and their expression in methylbenzylnitrosamine-induced esophageal tumorigenesis. Carcinogenesis 12, 2373-2377.
14. Wang, Y., You, M., Reynolds, S. H., Stoner, G. D., and Anderson, M. W. (1990) Mutational activation of the cellular Harvey ras oncogene in rat esophageal papillomas induced by methylbenzylnitrosamine. Cancer Res. 50, 1591-1595.
15. Lozano, J.-C., Nakazawa, H., Cros, M.-P., Cabrai, R., and Yamasaki, H. (1994) G → A mutations in p53 and Ha-ras genes in esophageal papillomas induced by N-nitrosomethylbenzylamine in two strains of rats. Mol.Carcinog. 9, 33-39.
16. 6-substituted guanine-induced mutagenesis of ras oncogenes. Proc. Natl. Acad. Sci. U.S.A. 86, 8650-8654.
17. Labuc, G. E., and Archer, M. C. (1982) Esophageal and hepatic microsomal metabolism of N-nitrosomethylbenzylamine and N-nitrosodimethylamine in the rat. Cancer Res. 42, 3181-3186.
18. Kawanishi, T., Ohno, Y., Takahashi, A., Takanaka, A., Kasuya, Y., and Omori, Y. (1985) Relation between hepatic microsomal metabolism of N-nitrosamines and cytochrome P-450 species. Biochem. Pharmacol. 34, 919-924.
19. Kawanishi, T., Ohno, Y., Takahashi, A., Takanaka, A., Kasuya, Y., and Omori, Y. (1985) Substrate concentration dependency of N-nitrosodimethylamine and N-nitrosomethylbenzylamine metabolism in rat liver. Carcinogenesis 6, 823-828.
20. Lee, M., Ishizaki, H., Brady, J. F., and Yang, C. S. (1989) Substrate specificity and alkyl group selectivity in the metabolism of N-nitrosodialkylamines. Cancer Res. 49, 1470-1474.
21. Farrelly, J. G., and Stewart, M. L. (1982) The metabolism of a series of methylalkylnitrosamines. Carcinogenesis 3, 1299-1302.
22. Ivankovic, S. (1978) Carcinogene wirkung von N-benzyl-N-nitrosoharnstoff (BzNH) an BD-ratten (Carcinogenic effects of N-benzyl-N-nitrosourea in BD rats). Z. Krebsforsch. 91, 63-68.
23. Lin, D. X., Malaveille, C., Park, S. S., Gelboin, H. V., and Bartsch, H. (1990) Contribution of DNA methylation and benzylation to N-nitroso-N-benzylmethylamine-induced mutagenesis in bacteria: effects of rat liver cytochrome P450 isozymes and glutathione transferases. Carcinogenesis 11, 1653-1658.
24. Kohda, K. H., Anjo, T., Nochizuki, M., Kawazoe, Y., and Okada, M. (1982) Mutagenicity of α-acetoxy derivatives of N-methyl-N-benzylnitrosamine and N,N-dibenzylnitrosamine in V79 cells: A comparison between methylating and benzylating mutagens. Gann 73, 517-521.
25. Wiessler, M., Romuruen, K., and Pool, B. L. (1983) Biological activity of benzylating N-nitroso compounds. Models of activated N-nitrosomethylbenzylamine. Carcinogenesis 4, 867-871.
26. Moschel, R. C., Hudgins, W. R., and Dipple, A. (1980) Aralkylation of guanosine by the carcinogen N-nitroso-N-benzylurea. J. Org. Chem. 45, 533-535.
27. Su, C. M., Brash, D. E., Chang, M. J. W., Hart, R. W., and D'Ambrosio, S. M. (1983) Induction of single-strand breaks plus alkali-labile bonds by N-nitrosoureas in rat tissues in vivo: ethylnitrosourea versus benzylnitrosourea. Mutat. Res. 108, 1-12.
28. 6-benzylguanine provides a means to evaluate the role of this protein in protection against carcinogenic and therapeutic alkylating agents. Proc. Natl. Acad. Sci. U.S.A. 87, 5368-5372.
29. 6-substituted 2′-deoxyguanosine residues at the first, second, or both positions of codon 12. Chem. Res. Toxicol. 1, 391-397.
30. 6-methylguanine. Cancer Res. 53, 2780-2785.
31. Hendrickson, J. B., Bergeron, R., and Sternbach, D. D. (1975) New "Gabriel" synthesis of amines. Tetrahedron 31, 2517-2521.
32. Gupta, R. C. (1984) Nonrandom binding of the carcinogen N-hydroxy-2-acetylaminofluorene to repetitive sequences of rat liver DNA in vivo. Proc. Natl. Acad. Sci. U.S.A. 81, 6943-6947.
33. Swann, P. F., and Magee, P. N. (1968) Nitrosamine-induced carcinogenesis. The alkylation of nucleic acids of the rat by N-methyl-N-nitrosourea, dimethylnitrosamine, dimethylsulphate, and methyl methanesulphonate. Biochem. J. 110, 39-47.
34. Hecht, S. S., Spratt, T. E., and Trushin, N. (1988) Evidence for 4-(3-pyridyl)-4-oxobutylation of DNA in F344 rats treated with the tobacco specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N′-nitrosonornicotine. Carcinogenesis 9, 161-165.
35. Moschel, R. C., Hudgins, W. R., and Dipple, A. (1984) Substituent-induced effects on the stability of benzylated guanosines: Model systems for the factors influencing the stability of carcinogen-modified nucleic acids. J. Org. Chem. 49, 363-372.
36. Hecht, S. S., Trushin, N., Castonguay, A., and Rivenson, A. (1986) Comparative tumorigenicity and DNA methylation in F344 rats by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N-nitrosodimethylamine. Cancer Res. 46, 498-502.
37. 6-methylguanine levels and histopathological changes in the rat esophagus and liver following single and repeated adminstration of N-nitrosomethylbenzylamine. Carcinogenesis 17, 1135-1140.
38. 6-benzylguanine. Biochemistry 32, 11998-12006.
39. Kraft, P. L., and Tannenbaum, S. R. (1980) Distribution of N-nitrosomethylbenzylamine evaluated by whole-body radioautography and densitometry. Cancer Res. 40, 1921-1927.
40. Moschel, R. C., Hudgins, W. R., and Dipple, A. (1986) Reactivity effects on site selectivity in nucleoside aralkylation: A model for the factors influencing the sites of carcinogen-nucleic acid interactions. J. Org. Chem. 51, 4180-4185.
41. Moschel, R. C., Hudgins, W. R., and Dipple, A. (1979) Selectivity in nucleoside alkylation and aralkylation in relation to chemical carcinogenesis. J. Org. Chem. 44, 3324-3328.
42. Dipple, A. (1995) DNA adducts of chemical carcinogenesis. Carcinogenesis 16, 437-441.
43. McGarrity, J. F., and Smyth, T. (1980) Hydrolysis of diazomethane: kinetics and mechanism. J. Am. Chem. Soc. 102, 7303-7308.
44. Finneman, J. I., and Fishbein, J. C. (1995) Mechanisms of benzyl group transfer in the decay of (E)-arylmethanediazoates and aryldiazomethanes in aqueous solutions. J. Am. Chem. Soc. 117, 4228-4239.
45. Chiang, Y., and Kresge, A. J. (1985) Mechanism of hydration of simple olefins in aqueous solution, cis-and trans-cyclooctene. J. Am. Chem. Soc. 107, 6363-6367.