Efficient nitroso group transfer from N-nitrosoindoles to nucleotides and 2'-deoxyguanosine at physiological pH. A new pathway for N- nitrosocompounds to exert genotoxicity

Journal of Biological Chemistry

Volumn 274, Issue 26, 1999, Pages 18319-18326

  Lucas, Lynda T ^a   Gatehouse, David ^b   Shuker, David E G ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYGUANOSINE; INDOLE DERIVATIVE; NITROSO DERIVATIVE; NUCLEOTIDE; PURINE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DEAMINATION; DNA ALKYLATION; GENOTOXICITY; MUTAGENICITY; PH; PRIORITY JOURNAL; PURIFICATION;

ACETONITRILES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; HYDROGEN-ION CONCENTRATION; INDOLES; MASS SPECTROMETRY; MODELS, CHEMICAL; NITROSO COMPOUNDS; NUCLEOTIDES;

EID: 0033603420     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.274.26.18319     Document Type: Article

References (29)

1. Bartsch, H. (1991) in Relevance to Human Cancer of N-Nitroso Compounds, Tobacco Smoke and Mycotoxins (O'Neill, I. K., Chen, J., and Bartsch, H., eds) pp. 1-8, International Agency for Research on Cancer (IARC), Lyon
2. Wakabayashi, K., Nagao, M., and Sugimura, T. (1989) Cancer Surv. 8, 385-399
3. Wakabayashi, K., Nagao, M., Tahira, T., Saito, H., Katayama, M., Marumo, S., and Sugimura, T. (1985) Proc. Jpn. Acad. Sci. Ser. B 61, 190-192
4. Wakabayashi, K., Nagao, M., Ochiai, M., Fujita, Y., Tahira, T., Nakayasu, M., Ohgaki, H., Takayama, S., and Sugimura, T. (1987) in Relevance of N-Nitroso Compounds to Human Cancer: Exposures and Mechanisms (Bartsch, H., O'Neill, I. K., and Schulte-Hermann, R., eds) pp. 287-291, International Agency for Research on Cancer (IARC), Lyon
5. Yamashita, K., Wakabayashi, K., Kitagawa, Y., Nagao, M., and Sugimura, T. (1988) Carcinogenesis 9, 1905-1907
6. Furihata, C., Sato, Y., Yamakoshi, A., Takimoto, M., and Mateushima, T. (1987) Jpn. J. Cancer Res. (Gann) 78, 432-435
7. Wakabayashi, K., Nagao, M., Ochiai, M., Tahira, T., Yamaizuma, Z., and Sugimura, T. (1985) Mutat. Res. 143, 17-21
8. Wakabayashi, K., Nagao, M., Tahira, T., Yamaizuma, Z., Katayami, M., Marumo, S., and Sugimura, T. (1986) Mutagenesis 1, 423-426
9. Ohta, T., Isa, M., Suzuki, Y., Yamahata, N., Suzuki, S., and Kurechi, T. (1981) Biochem. Biophys. Res. Commun. 100, 52-57
10. Gatehouse, D., and Wedd, D. (1983) Mutat. Res. 124, 35-51
11. Valin, N., Haybron, D., Groves, L., and Mower, H. F. (1985) Mutat. Res. 158, 159-168
12. Ochiai, M., Wakabayashi, K., Sugimura, T., and Nagao, M. (1986) Mutat. Res. 172, 189-197
13. Suzuki, T., Yamaoka, R., Nishi, M., Ide, H., and Makino, K. (1996) J. Am. Chem. Soc. 118, 2515-2516
14. Suzuki, T., Kanaori, K., and Makino, K. (1997) Nucleic Acids Symp. Ser. 37, 313-314
15. Furniss, B. S., Hannorford, A. J., Smith, P. W. G., and Tatchell, A. R. (1989) Vogel's Textbook of Practical Organic Chemistry, Fifth Ed., p. 1216, Longmans, London
16. Glaser, R., and Son, M.-S. (1996) J. Am. Chem. Soc. 118, 10942-10943
17. Crookes, M. J., and Williams, D. L. H. (1998) Chem. Soc. Chem. Commun. 571-572
18. Furniss, B. S., Hannorford, A. J., Smith, P. W. G., and Tatchell, A. R. (1989) Vogel's Textbook of Practical Organic Chemistry, Fifth Ed., pp. 413-414, Longmans, London
19. Suzuki, T., Yoshida, M., Yamada, M., Ide, H., Kobayashi, M., Kanaori, K., Tajima, K., and Makino, K. (1998) Biochemistry 37, 11592-11598
20. Suzuki, T., Matsumura, Y., Ide, H., Kanaori, K., Tajima, K., and Makino, K. (1997) Biochemistry 38, 8013-8019
21. Shimada, N., Yagisawa, N., Naganawa, H., Takita, T., Hamada, M., Takeuchi, T., and Umezawa, H. (1981) J. Antibiot. 34, 1216-1218
22. Nakamura, H., Yagisawa, N., Shimada, N., Takita, T., Umezawa, H., and Iitaka, Y. (1981) J. Antibiot. 34, 1219-1221
23. Kircher, J. J., Sigurdsson, S. Th., and Hopkins, P. B. (1992) J. Am. Chem. Soc. 114, 4021-4027
24. Venitt, S., Crofton-Sleigh, C., Ooi, S. L., and Bonnett, R. (1980) Carcinogenesis 1, 523-532
25. Bonnett, R., and Holleyhead, R. (1974) J. Chem. Soc. Perkin I, 962-964
26. Meyer, T. A., Williams, D. L. H., Bonnett, R., and Ooi, S. L. (1982) J. Chem. Soc. Perkin II, 1383-1387
27. Castro, A., Iglesias, E., Leis, J. R., Pena, M. E., Tato, J. V., and Williams, D. L. H. (1986) J. Chem. Soc. Perkin II, 1165-1168
28. Loeb, L. A., and Preston, B. D. (1986) Annu. Rev. Genet. 20, 201-230
29. Wink, D. A., Kaaprzak, K. S., Maragos, C. M., Elespuru, R. K., Misra, M., Dunams, T. M., Cebula, T. A., Koch, W. H., Andrews, A. W., Allen, J. S., and Reefer, L. K. (1991) Science 254, 1001-1003