Singlet oxygen oxidation of 2′-deoxyguanosine. Formation and mechanistic insights

Tetrahedron

Volumn 62, Issue 46, 2006, Pages 10709-10715

  Ravanat, Jean Luc ^a   Martinez, Glaucia R ^b,c   Medeiros, Marisa H G ^c   Di Mascio, Paolo ^c   Cadet, Jean ^a  

^a LCIB   (France)

^b FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

8 Oxo 7,8 dihydroguanine; Cycloaddition; Dioxetane; Endoperoxide; Singlet oxygen; Spiroiminodihydantoin

Indexed keywords

DEOXYGUANOSINE; DNA; NUCLEOSIDE; OXYGEN;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

EID: 33749427025     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.097     Document Type: Article

References (41)

1. Cadet J., Sage E., and Douki T. Mutat. Res. 571 (2005) 3
2. Prat F., Houk N., and Foote C.S. J. Am. Chem. Soc. 119 (1997) 3951
3. Lee P.C.C., and Rodgers M.A.J. Photochem. Photobiol. 45 (1987) 79
4. Sheu C., and Foote C.S. J. Am. Chem. Soc. 117 (1995) 6439
5. Sheu C., Kang P., Khan S., and Foote C.S. J. Am. Chem. Soc. 124 (2002) 3905
6. Simon M.I., and Van Vunakis H. J. Mol. Biol. 4 (1962) 488
7. Simon M.I., and Van Vunakis H. Arch. Biochem. Biophys. 105 (1964) 197
8. Waskell L.A., Sastry K.S., and Gordon M.P. Biochim. Biophys. Acta 129 (1966) 42
9. Simon M.I., and Van Vunakis H. Biochim. Biophys. Acta 129 (1966) 49
10. Hallett P.R., Hallett B.P., and Snipes W. Biophys. J. 10 (1970) 305
11. Rosenthal I., and Pitts Jr. J.N. Biophys. J. 11 (1971) 963
12. Saito I., Inoue K., and Matsuura T. Photochem. Photobiol. 21 (1975) 27
13. Cadet J., and Téoule R. Photochem. Photobiol. 28 (1978) 661
14. Cadet J., Balland A., Voituriez L., Hahn B.-S., and Wang S.Y. In: Rodgers M.A.J., and Powers E.L. (Eds). Oxygen and Oxy-Radicals in Chemistry and Biology (1981), Academic, New York, NY 610
15. Ravanat J.-L., Berger M., Benard F., Langlois R., Ouellet R., van Lier J.E., and Cadet J. Photochem. Photobiol. 55 (1992) 809
16. Buchko G.W., Cadet J., Berger M., and Ravanat J.-L. Nucleic Acids Res. 20 (1992) 4847
17. Ravanat J.-L., and Cadet J. Chem. Res. Toxicol. 8 (1995) 379
18. Niles J.C., Wishnok J.S., and Tannenbaum S.R. Org. Lett. 3 (2001) 963
19. Luo W., Muller J.G., Rachlin E.M., and Burrows C.J. Org. Lett. 2 (2000) 613
20. Luo W., Muller J.G., and Burrows C.J. Org. Lett. 3 (2001) 2801
21. Luo W., Muller J.G., Rachlin E.M., and Burrows C.J. Chem. Res. Toxicol. 14 (2001) 927
22. Adam W., Arnold M.A., Grune M., Nau W.M., Pischel U., and Saha-Möller C.R. Org. Lett. 4 (2002) 537
23. Jia L., Shafirovich V., Shapiro R., Geacintov N.E., and Broyde S. Biochemistry 44 (2005) 6043
24. Jia L., Shafirovich V., Shapiro R., Geacintov N.E., and Broyde S. Biochemistry 44 (2005) 13342
25. Karwowski, B.; Dupeyrat, F.; Bardet, M.; Ravanat, J.-L.; Krajewski, P.; Cadet, J. Chem. Res. Toxicol., in press.
26. Martinez G.R., Ravanat J.-L., Medeiros M.H.G., Cadet J., and Di Mascio P. J. Am. Chem. Soc. 122 (2000) 10212
27. Regulus P., Spessotto S., Gateau M., Cadet J., Favier A., and Ravanat J.-L. Rapid Commun. Mass Spectrom. 16 (2004) 2223
28. Ravanat J.-L., Remaud G., and Cadet J. Arch. Biochem. Biophys. 374 (2000) 118
29. Martinez G.R., Medeiros M.H.G., Ravanat J.-L., Cadet J., and Di Mascio P. Biol. Chem. 383 (2002) 607
30. Ye Y., Muller J.G., Luo W., Mayne C.L., Shalopp A.J., Jones R.A., and Burrows C.J. J. Am. Chem. Soc. 125 (2003) 13926
31. McCallum J.E.B., Kuniyoshi C.Y., and Foote C.S. J. Am. Chem. Soc. 126 (2004) 16777
32. Sheu C., and Foote C.S. J. Am. Chem. Soc. 117 (1995) 474
33. Raoul S., and Cadet J. J. Am. Chem. Soc. 118 (1996) 1892
34. Cadet J., Berger M., Buchko G.W., Joshi P.C., Raoul S., and Ravanat J.-L. J. Am. Chem. Soc. 116 (1994) 7403
35. Kang P., and Foote C.S. J. Am. Chem. Soc. 124 (2002) 4865
36. Cadet J., Douki T., Gasparutto D., and Ravanat J.-L. Mutat. Res. 531 (2003) 5
37. Douki T., Ravanat J.-L., Angelov D., Wagner J.R., and Cadet J. Top. Curr. Chem. 236 (2004) 1
38. Ravanat J.-L., Saint-Pierre C., Di Mascio P., Martinez G.R., Medeiros M.H.G., and Cadet J. Helv. Chim. Acta 84 (2001) 3702
39. Boiteux S., Gajewski E., Laval J., and Dizdaroglu M. Biochemistry 31 (1992) 106
40. Buchko G.W., Wagner J.R., Cadet J., Raoul S., and Weinfeld M. Biochim. Biophys. Acta 1263 (1995) 17
41. Ravanat J.-L., Di Mascio P., Martinez G.R., Medeiros M.H.G., and Cadet J. J. Biol. Chem. 275 (2000) 40601