In vitro DNA deamination by α-nitrosaminoaldehydes determined by GC/MS- SIM quantitation

Chemical Research in Toxicology

Volumn 13, Issue 2, 2000, Pages 72-81

  Park, Misun ^a   Loeppky, Richard N ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL DNA; NITROSAMINE;

ANIMAL TISSUE; ARTICLE; CATTLE; CONTROLLED STUDY; DEAMINATION; DNA DAMAGE; GAS CHROMATOGRAPHY; HYDROLYSIS; ION MONITORING; MASS SPECTROMETRY; MUTAGENICITY; NONHUMAN; THYMUS;

ADENINE; ALDEHYDES; ANIMALS; CATTLE; CYTOSINE; DEAMINATION; DIETHYLNITROSAMINE; DNA; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GUANINE; NITROSAMINES;

EID: 0034010202     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990126d     Document Type: Article

References (29)

1. Preussmann, R., Habs, M., Habs, H., and Schmaehl, D. (1982) Carcinogenicity of N-nitrosodiethanolamine in rats at five different dose levels. Cancer Res. 42, 5167-5171.
2. Lijinsky, W., Reuber, M. D., and Manning, W. B. (1980) Potent carcinogenicity of nitrosodiethanolamine in rats. Nature 288, 589-590.
3. Fan, T. Y., Morrison, J., Rounbehler, D. P., Ross, R., Fine, D. H., Miles, W., and Sen, N. P. (1977) N-Nitrosodiethanolamine in synthetic cutting fluids: a part-per-hundred impurity. Science 196, 70-71.
4. Fan, T. Y., Goff, U., Song, L., Fine, D. H., Arsenault, G. P., and Biemann, K. (1977) N-Nitrosodiethanolamine in cosmetics, lotions and shampoos. Food Cosmet. Toxicol. 15, 423-430.
5. Havery, D. C., and Chou, H. J. (1994) Nitrosamines in sunscreens and cosmetic products. In Nitrosamines and Related N-Nitroso Compounds: Chemistry and Biochemistry (Loeppky, R. N., and Michejda, C. J., Eds.) pp 20-33, American Chemical Society, Washington, DC.
6. Loeppky, R. N. (1999) The mechanism of bioactivation of N-nitrosodiethanolamine. Drug Metab. Rev. 31, 175-193.
7. Loeppky, R. N., Fuchs, A., Janzowski, C., Humberd, C., Goelzer, P., Schneider, H., and Eisenbrand, G. (1998) Probing the mechanism of the carcinogenic activation of N-nitrosodiethanolamine with deuterium isotope effects: In vivo induction of DNA single strand breaks and related in vitro assays. Chem. Res. Toxicol. 11, 1556-1566.
8. Preussmann, R., and Stewart, B. W. (1984) N-Nitroso carcinogens. In Chemical Carcinogenesis (Searle, C. E., Ed.) pp 643-828, American Chemical Society, Washington, DC.
9. Mochizuki, M., Anjo, T., and Okada, M. (1980) Isolation and characterization of N-alkyl-N-(hydroxymethyl)nitrosamines from N-alkyl-N-(hydroperoxymethyl) nitrosamines by deoxygenation. Tetrahedron Lett. 21, 3693-3696.
10. Yang, C. S., Yoo, J. S. H., Ishizaki, H., and Hong, J. (1990) Cytochrome P450IIE1: roles in nitrosamine metabolism and mechanisms of regulation. Drug Metab. Rev. 22, 147-159.
11. Airoldi, L., Bonfanti, M., Benfenati, E., Tavecchia, P., and Fanelli, R. (1983) Identification of an acidic metabolite of N-nitrosodiethanolamine isolated from rat urine. Biomed. Mass Spectrom. 10, 334-337.
12. Airoldi, L., Bonfanti, M., Fanelli, R., Bove, B., Benfenati, E., and Gariboldi, P. (1984) Identification of a nitrosamino aldehyde and a nitrosamino acid resulting from β-oxidation of N-nitrosodiethanolamine. Chem.-Biol. Interact. 51, 103-113.
13. Loeppky, R. N., Tomasik, W., and Kerrick, B. E. (1987) Nitroso transfer from α-nitrosamino aldehydes: Implications for carcinogenesis. Carcinogenesis 8, 941-946.
14. Loeppky, R. N., Tomasik, W., Denkel, E., and Eisenbrand, G. (1987) α-Nitrosaminoaldehydes: Highly reactive metabolites. IARC Sci. Publ. 84, 94-99.
15. Loeppky, R. N., Tomasik, W., Kovacs, D. A., Outram, J. R., and Byington, K. H. (1984) Alternative bioactivation routes for β-hydroxynitrosamines. Biochemical and chemical model studies. In N-Nitroso Compounds: Occurrence, Biological Effects and Relevance to Human. Cancer (Bartsch, H., O'Neill, I., and Von Borstel, R. C., Eds.) pp 429-436, International Agency for Research on Cancer, Lyon, France.
16. Chung, F. L., and Hecht, S. S. (1985) Formation of the cyclic 1,-N2-glyoxal-deoxyguanosine adduct upon reaction of N-nitroso-2-hydroxymorpholine with deoxyguanosine. Carcinogenesis 6, 1671-1673.
17. Farrelly, J. G., Stewart, M. L., and Lijinsky, W. (1984) The metabolism of nitrosodi-n-propylamine, nitrosodiallylamine and nitrosodiethanolamine. Carcinogenesis 5, 1015-1019.
18. Farrelly, J. G., Thomas, B. J., and Lijinsky, W. (1987) Metabolism and cellular interactions of N-nitrosodiethanolamine. IARC Sci. Publ. 84, 87-90.
19. Loeppky, R. N., Lee, M. P., and Mueller, S. (1993) DNA modification by α-nitrosamino aldehydes. In The Chemistry of DNA Adducts (Hemminki, K., and Bartsch, H., Eds.) pp 429-432, International Agency for Research on Cancer, Lyon, France.
20. Loeppky, R. N., Cui, W., Goelzer, P., and Ye, Q. (1999) Glyoxalguanine DNA adducts: Detection, stability and formation from nitrosamines. IARC Sci. Publ. 150, 155-168.
21. Dess, D. B., and Martin, J. C. (1991) A useful 12-1-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-1-5 species. J. Am. Chem. Soc. 113, 7277-7287.
22. Nguyen, T., Brusnson, D., Crespi, C. L., Penman, B. W., Wishnok, J. S., and Tannenbaum, S. R. (1992) DNA damage and mutation in human cells exposed to nitric oxide in vitro. Proc. Natl. Acad. Sci. U.S.A. 89, 3030-3034.
23. Gehrke, C. W., McCune, R. A., Gama-Sousa, M., Erlich, M., and Kuo, K. (1984) Quantitative reversed-phase high-performance liquid chromatography of major and modified nucleosides in DNA. J. Chromatogr. 301, 199-219.
24. Dess, D. B., and Martin, J. C. (1983) Readily accessible 12-1-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem. 48, 4255-4256.
25. Shapiro, R., and Pohl, S. H. (1968) Reaction of ribonucleosides with nitrous acid. Side products and kinetics. Biochemistry 7, 448-455.
26. Loeppky, R. N., Yu, L., Gu, F., and Ye, Q. (1996) DNA Guanine Adducts from 3-methyl-1,2,3-oxadiazolinium ions. J. Am. Chem. Soc. 118, 10995-11005.
27. Wink, D. A., Kasprzak, K. S., Margos, C. M., Elespuru, P. K., Misra, M., Dunams, T. M., Cebula, T. A., Koch, W. H., Andrews, A. W., Allen, J. S., and Keefer, L. K. (1991) DNA Deaminating ability and genotoxicity of nitric oxide and its progenitors. Science 254, 1001-1003.
28. Scherer, G., Ludeke, B., Kleihues, P., Loeppky, R. N., and Eisenbrand, G. (1991) Mutagenicity, DNA damage and DNA adduct formation by N-nitroso-2-hydroxyalkylamine and corresponding aldehydes. IARC Sci. Publ. 105, 339-342.
29. Hecht, S. S., Lijinsky, W., Kovatch, R. M., Chung, F. L., and Saavedra, J. E. (1989) Comparative tumorigenicity of N-nitroso-2-hydroxymorpholine, N-nitrosodiethanolamine, and N-nitrosomorpholine in A/J mice and F344 rats. Carcinogenesis 10, 1475-1477.