Nitration of 2′-deoxyguanosine by a NO/O2 gas mixture: Identification and characterization of N2-nitro-2′ -deoxyguanosine

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3173-3176

  Yamada, Masaki ^a,c   Suzuki, Toshinori ^a,d   Kanaori, Kenji ^b   Tajima, Kunihiko ^b   Sakamoto, Shunji ^b   Kodaki, Tsutomu ^b   Makino, Keisuke ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

^c SHIMADZU CORPORATION   (Japan)

^d MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXYXANTHOSINE; 8 NITROGUANINE; 8 NITROXANTHINE; DEOXYGUANOSINE DERIVATIVE; GUANINE DERIVATIVE; N 2 NITRO 2' DEOXYGUANOSINE; NITRIC OXIDE; OXYGEN; UNCLASSIFIED DRUG; XANTHINE DERIVATIVE; XANTHOSINE; 8-NITROGUANINE; 8-NITROXANTHINE; DEOXYGUANOSINE; DRUG DERIVATIVE; GUANINE; NITRATE; NUCLEOSIDE; XANTHINE;

ARTICLE; GAS; NITRATION; PH; PROTEIN ANALYSIS; SPECTROMETRY; CHEMICAL STRUCTURE; CHEMISTRY;

DEOXYGUANOSINE; GUANINE; MOLECULAR STRUCTURE; NITRATES; NITRIC OXIDE; NUCLEOSIDES; OXYGEN; XANTHINE; XANTHINES;

EID: 0141744753     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0300468     Document Type: Article

References (32)

1. Moncada, S.; Palmer, R. M. J.; Higgs, E. A. Pharmacol. Rev. 1991, 43, 109-142.
2. Weinberger, B.; Laskin, D. L.; Heck, D. E.; Laskin, J. D. Toxicol. Sci. 2001, 59, 5-16.
3. Finlayson-Pitts, B. J.; Pitts, J. N., Jr. Chemistry of the Upper and Lower Atmosphere: Theory, Experiments, and Applications; Academic Press: San Diego, 2000.
4. Ohshima, H.; Bartsch, H. Mutat. Res. 1994, 305, 253-264.
5. Wink, D. A.; Kasprzak, 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.; Keefer, L. K. Science 1991, 254, 1001-1003.
6. Nguyen, T.; Brunson, D.; Crespi, C. L.; Penman, J. S.; Tannenbaum, S. R. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3030-3034.
7. Caulfield, J. L.; Wishnok, J. S.; Tannenbaum, S. R. J. Biol. Chem. 1998, 273, 12689-12695.
8. Suzuki, T.; Yamaoka, R.; Nishi, M.; Ide, H.; Makino, K. J. Am. Chem. Soc. 1996, 118, 2515-2516.
9. Yermilov, V.; Rubio, J.; Becchi, M.; Friesen, M. D.; Pignatelli, B.; Ohshima, H. Carcinogenesis 1995, 16, 2045-2050.
10. Chen, H.-J. C.; Chen, Y.-M.; Wang, T.-F.; Wang, K.-S.; Shiea, J. Chem. Res. Toxicol. 2001, 14, 536-546.
11. Byun J.; Henderson, J. P.; Mueller, D. M.; Heinecke, J. W. Biochemistry 1999, 38, 2590-2600.
12. Suzuki, T., Yamada, M., Kanaori, K., Tajima, K., Morii, T. and Makino, K. Nucleic Acids Symp. Ser. 1999, 42, 155-156.
13. 2 (99.5%, Kyoto Teisan) at a Y-type connector. The mixed gas was run through a Teflonlined tube (5.0 x 200 mm) and bubbled into the dGuo solution by a glass frit (4.0 x 200 mm, pore size 20-30 μm, Kinoshita Rika, Tokyo, Japan).
14. HPLC Conditions. RP-HPLC analyses were performed using an octadecylsilane column (ULTORON VX-ODS, 6.0 x 150 mm, particle size 5 μm, Shinwa Chemical Industry, Kyoto, Japan) eluted with 100 mM triethylammonium acetate buffer (pH 7.0) containing acetonitrile. The acetonitrile concentration was increased from 0 to 20% for 20 min in a linear gradient mode. The flow rate was 1.5 mL/min.
15. 2-Xan was synthesized from Xan by the treatment with nitric acid (see ref 10). The samples synthesized were purified by RP-HPLC.
16. 6, 311.0740).
17. Fridman, A. L.; Ivshin, V. P.; Novikov, S. S. Russ. Chem. Rev. 1969, 38, 640-654.
18. Unterhalt, B. In Methoden der Organischen Chemie, Band E16a; Klamann, D., Ed.; Georg Thieme Verlag: Stuttgart, 1990; pp 1147-1181.
19. Politzer, P.; Sukumar, N.; Jayasuriya, K.; Rnaganathan, S. J. Am. Chem. Soc. 1988, 110, 3425-3430.
20. -1 by the comparison of the integration of H1′ proton signal and the RP-HPLC peak area detected at 260 nm with those for dGuo. Gua, Xan, and dOxo were separated and quantified using another HPLC eluent of 100 mM ammonium formate (pH 6.3) with acetonitrile, while 100 mM triethylammonium acetate (pH 7.0) was used as the eluent buffer for the nitrated products and dXao.
21. Sodum, R. S.; Fiala, E. S. Chem. Res. Toxicol. 2001, 14, 438-450.
22. Yermilov, V.; Rubio, J.; Ohshima, H. FEBS Lett. 1995, 376, 536-546.
23. Bhatia, S.; Hall, J. H., Jr. J. Phys. Chem. 1980, 84, 3255-3259.
24. McKee, M. L. J. Am. Chem. Soc. 1995, 117, 1629-1637.
25. Goldstein, S.; Czapski, G. J. Am. Chem. Soc. 1995, 117, 12078-12084.
26. Goldstein, S.; Czapski, G. J. Am. Chem. Soc. 1996, 118, 3419-3425.
27. Shafirovich, V.; Cadet, J.; Gasparutto, D.; Dourandin, A.; Geacintov, N. E. Chem. Res. Toxicol. 2001, 14, 233-241.
28. Spencer, J. P. E.; Whitemen, M.; Jenner, A.; Halliwell, B. Free Radical Biol. Med. 2000, 28, 1039-1050.
29. Malhotra, R.; Ross, D. S. In Nitration: Recent Laboratory and Industrial Development; ACS Symposium Series 623; American Chemical Society: Washington, DC, 1996; pp 32-41.
30. Steeken, S. Chem. Rev. 1989, 89, 503-520.
31. Wängberg, I.; Etzkorn, T.; Barnes, I.; Platt, U.; Becker, K. H. J. Phys. Chem. A 1997, 101, 9694-9698.
32. Millar, R. W.; Colclough, M. E.; Desai, H.; Golding, P.; Honey, P. J.; Paul, N. C.; Sanderson, A. J.; Stewart, M. J. In Nitration: Recent Laboratory and Industrial Development; ACS Symposium Series 623; American Chemical Society: Washington, DC, 1996; pp 104-121.