Detection of concomitant formation of O6-carboxymethyl- and O6- methyl-2'-deoxyguanosine in DNA exposed to nitrosated glycine derivatives using a combined immunoaffinity/HPLC method

Chemical Research in Toxicology

Volumn 12, Issue 1, 1999, Pages 106-111

  Harrison, Kathryn L ^a   Jukes, Rebekah ^a   Cooper, Donald P ^a   Shuker, David E G ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYGUANOSINE DERIVATIVE; DNA; GLYCINE DERIVATIVE;

ARTICLE; CHEMICAL MUTAGENESIS; DNA ADDUCT; DNA ALKYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNOAFFINITY CHROMATOGRAPHY; REACTION ANALYSIS;

ANIMALS; CALIBRATION; CARCINOGENS; CATTLE; CHROMATOGRAPHY, AFFINITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; DNA; DNA ADDUCTS; GLYCINE; IMMUNOSORBENTS; NITROSO COMPOUNDS; THYMUS GLAND;

EID: 0032936961     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980057n     Document Type: Article

References (41)

1. Miller, E. C. (1978) Some current perspectives on chemical carcinogenesis in humans and experimental animals: address. Cancer Res. 38, 1479-1496.
2. Saffhill, R., Margison, G. P., and O'Connor, P. J. (1985) Mechanisms of carcinogenesis induced by alkylating agents. Biochim. Biophys. Acta 823, 111-145.
3. Karran, P., and Lindahl, T. (1985) Cellular defence mechanisms against alkylating agents. Cancer Surv. 4, 585-599.
4. Shuker, D. E. G., Tannenbaum, S. R., and Wishnok, J. S. (1981) N-Nitrosobile acid conjugates. I. Synthesis, chemical reactivity and mutagenic activity J. Org. Chem. 46, 2092-2096.
5. Song Puju, Shuker, D. E. G., Bishop, W. W., Falchuk, K. R., Tannenbaum, S. R., and Thilly, W. G. (1982) Mutagenicity of N-nitrosobile acid conjugates, N-nitrosoglycocholic acid and N-nitrosotaurocholic acid. Cancer Res. 42, 2601-2604.
6. Busby, W. F., Jr., Shuker, D. E. G., Charnley, G., Newberne, P. M., Tannenbaum, S. R., and Wogan, G. N. (1985) Carcinogenicity of the nitrosated bile acid conjugates, N-nitrosoglycocholic acid and N-nitrosotaurocholic acid. Cancer Res. 45, 1367-1371.
7. Shuker, D. E. G., Howell, J. R., and Street, B. W. (1987) Formation and fate of nucleic acid and protein adducts from N-nitroso bile acid conjugates. In Relevance of N-nitroso Compounds for Human Cancer: Exposures and Mechanisms (Bartsch, H., O'Neill, I. K., and Schülte-Hermann, R., Eds.) IARC Scientific Publication 84, pp 187-190, International Agency for Research on Cancer, Lyon, France.
8. Challis, B. C. (1989) Chemistry and biology of nitrosated peptides. Cancer Surv. 8, 363-384.
9. Anderson, D., and Blowers, S. D. (1994) Limited cancer bioassay to test a potential food chemical. Lancet 344, 343-344.
10. Bulay, O., Mirvish, S. S., Garcia, H., Pelfrene, A. F., and Gold, B. (1979) Carcinogenicity test of six nitrosamides and a nitrosocyanamide administered orally to rats. J. Natl. Cancer Inst. 62, 1523-1528.
11. Maekaiva, A., Ogiu, T., Matsuoka, C., Onodera, H., Furuta, K., Tangawa, H., and Odashima, S. (1983) Induction of tumours in the small intestine and mammary gland of female Donryu rats by continuous oral administration of N-carboxymethyl-N-nitrosourea J. Cancer Res. Clin. Oncol. 106, 12-16.
12. Zurlo, J., Curphey, T. J., Hiley, R., and Longnecker, D. S. (1982) Identification of 7-carboxymethylguanine in DNA from pancreatic acinar cells exposed to azaserine. Cancer Res. 42, 1286-1288.
13. 6-(carboxymethyl)-2′-deoxyguanosine: A DNA adduct formed by nitrosated glycine derivatives. Chem. Res. Toxicol. 10, 652-659.
14. 6-methylguanine in DNA. Cancer Res. 57, 366-369.
15. Jackson, P. E., Hall, C. N., Badawi, A. F., O'Connor, P. J., Cooper, D. P., and Povey, A. C. (1996) Frequency of Ki-ras mutations and DNA alkylation in colorectal tissue from individuals living in Manchester. Mol. Carcinog. 16, 12-19.
16. 6-Methylguanine in blood leucocyte DNA: an association with the georgraphic prevalence of gastric cancer and with low levels of seum pepsinogen A, a marker of severe chronic atrophic gastritis. Carcinogenesis 15, 1815-1820.
17. Hall, C. N., Badawi, A. F., O'Connor, P. J., and Saffhill, R. (1991) The detection of alkylation damage in the DNA of human gastrointestinal tissues. Br. J. Cancer 64, 59-63.
18. 6-Methyldeoxyguanosine in oesophageal DNA among individuals at high risk of oesophageal cancer. Int. J. Cancer 36, 661-665.
19. 6-Methylguanine-DNA transmethylase activity in extracts of human gastric mucosa. Carcinogenesis 5, 943-947.
20. Challis, B. C., Milligan, J. R., and Mitchell, R. (1990) Synthesis of N-nitrosopeptides. J. Chem. Soc., Perkin Trans, 1, 3103-3107.
21. Harvbrant, O., and Wachtmeister, C. A. (1968) Synthesis of mesyloxyacetic acid and some derivatives. Acta Chem. Scand. 22, 2043-2044.
22. Müller, E. (1908) Über pseudo diazoessigsäure (On pseudo diazoacetic acid). Chem. Ber. 41, 3116-3139.
23. Kreevoy, M. M., and Konasewich, D. E. (1970) The mechanism of hydrolysis of diazoacetate ion. J. Phys. Chem. 74, 4464-4472.
24. 6-methyldeoxyguanosine in DNA of cells alkylated in vitro and in vivo. Carcinogenesis 4, 1605-1609.
25. Chapeau, M. C., and Marnett, L. J. (1991) Enzymatic synthesis of purine deoxynucleoside adducts. Chem. Res. Toxicol. 4, 636-638.
26. Beranek, D. T., Weis, C. C., and Swenson, D. H. (1980) A comprehensive quantitative analysis of methylated and ethylated DNA using high-pressure liquid chromatography. Carcinogenesis 1, 595-606.
27. Wild, C. P. (1990) Antibodies to DNA alkylation adducts as analytical tools in chemical carcinogenesis. Mutat. Res. 233, 219-233.
28. 6-methylguanine in human DNA. Carcinogenesis 16, 1665-1669.
29. Osterman-Golkar, S., Ehrenberg, L., and Wachtmeister, C. A. (1970) Reaction kinetics and biological action in barley of monofunctional methanesulfonic esters. Radiat. Bot. 10, 303-327.
30. Yoshikawa, K., Uchino, H., Yamamoto, M., Yamanda, T., Tanimura, A., and Kondo, S. (1979) Effect of N-carboxyinethyl-N-nitrosourea on viability and mutagenic response of repair-deficient strains of Escherichia coli. Gann 70, 705-708.
31. Takahashi, K., Kohda, K., O'Hara, T., Sekiguchi, M., and Kawazoe, Y. (1988) Structural requirement for the induction of the adaptive response in Escherichia coli among N-(subsituted alkyl)-N-nitrosoureas. Mutat. Res. 202, 193-201.
32. Preussmann, R., and Stewart, B. W. (1984) N-Nitroso carcinogens. In Chemical Carcinogens (Searle, C. E., Ed.) ACS Monograph 182, Vol. 2, pp 643-828, American Chemical Society, Washington, DC.
33. Druckrey, H., Preussmann, R., Ivankovic, S., and Schmahl, D. (1967) Organotrope carcinogene wirkungen bei 65 verschiedene N-nitroso-verbindungen an BD-ratten (Organotropic carcinogenesis by 65 different N-nitrosocompounds in BD rats). Z. Krebsforsch. 69, 103-201.
34. Herron, D. C., and Shank, R. C. (1980) Methylated purines in human liver DNA after probable dimethylnitrosamine poisoning. Cancer Res. 40, 3116-3117.
35. Xu, G. P., and Reed, P. L. (1993) N-Nitroso compounds in fresh gastric juice and their relation to intragastric pH and nitrite employing an improved analytical method. Carcinogenesis 14, 2547-2551.
36. Bingham, S., Pignatelli, B., Pollock, J., Ellul, A., Mallaveille, C., Gross, G., Runswick, S., Cummings, J. H., and O'Neill, I. K. (1996) Does increased formation of endogenous N-nitroso compounds in the human colon explain the association between red meat and colon cancer? Carcinogenesis 17, 515-523.
37. Shephard, S. E., and Lutz, W. K. (1989) Nitrosation of dietary precursors. Cancer Surv. 8, 401-421.
38. Mirvish, S. S. (1995) Role of N-nitroso compounds (NOC) and N-nitrosation in etiology of gastric, esophageal, nasopharyngeal and bladder cancer and contribution to cancer of known exposures to NOC. Cancer Lett. 93, 17-48.
39. Dayal, B., Bhojawala, J., Rapole, K. R., Pramanik, B. N., Ertel, N. H., Shefer, S., and Salen, G. (1996) Chemical synthesis, structural analysis, and decomposition of N-nitroso bile acid conjugates. Bioorg. Med. Chem. 14, 885-890.
40. Dayal, B., and Ertel, N. H. (1997) Studies on N-nitroso bile acid amides in relation to their possible role in gastrointestinal cancer. Lipids 32, 1331-1340.
41. 6-alkylguanine-DNA alkyltransferase deficient cells. Carcinogenesis 18, 1561-1567.