Identification of the main oxidation products of 8-methoxy-2′- deoxyguanosine by singlet molecular oxygen

Free Radical Biology and Medicine

Volumn 38, Issue 11, 2005, Pages 1491-1500

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

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b CEA GRENOBLE   (France)

^c FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

Author keywords

8 Oxo 7,8 dihydro 2 deoxyguanosine; 18O Labeled endoperoxide; DNA damage; Free radicals; Mass spectrometry; Singlet molecular oxygen

Indexed keywords

2,2,4 TRIAMINO 5(2H) OXAZOLONE; 2,5 DIAMINO 4H IMIDAZOL 4 ONE; 8 METHOXY 2' DEOXYGUANOSINE; ALLANTOIN; DEOXYGUANOSINE DERIVATIVE; DEOXYRIBONUCLEOSIDE; ENDOPEROXIDE; HYDANTOIN DERIVATIVE; IMIDAZOLE DERIVATIVE; NAPHTHALENE DERIVATIVE; NUCLEOSIDE; OLIGONUCLEOTIDE; OXAZOLONE; SINGLET OXYGEN; UNCLASSIFIED DRUG; UREA;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LYSIS; OXIDATION; PRIORITY JOURNAL; SUBSTITUTION REACTION; TANDEM MASS SPECTROMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; DNA; GUANOSINE; HEAT; MASS SPECTROMETRY; MODELS, CHEMICAL; NUCLEOSIDES; OLIGONUCLEOTIDES; OXYGEN; PURINES; SINGLET OXYGEN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPIRO COMPOUNDS; TIME FACTORS; ULTRAVIOLET RAYS; UREA;

EID: 18844380262     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2005.02.008     Document Type: Article

References (27)

1. J.-L. Ravanat, P. Di Mascio, G.R. Martinez, M.H.G. Medeiros, and J. Cadet Singlet oxygen induces oxidation of cellular DNA J. Biol. Chem. 275 2000 40601 40604
2. J.-L. Ravanat, C. Saint-Pierre, P. Di Mascio, G.R. Martinez, M.H.G. Medeiros, and J. Cadet Damage to isolated DNA mediated by singlet oxygen Helv. Chim. Acta 84 2001 3702 3709
3. J.L. Ravanat, and J. Cadet Reaction of singlet oxygen with 2′-deoxyguanosine and DNA-isolation and characterization of the main oxidation products Chem. Res. Toxicol. 8 1995 379 388
4. J.C. Niles, J.S. Wishnok, and S.R. Tannenbaum Spiroiminodihydantoin is the major product of 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photooxidation by methylene blue Org. Lett. 3 2001 963 966
5. 18O]-labeled singlet oxygen for oxidative DNA damage studies Trends Photochem. Photobiol. 9 2002 25 39
6. 18O-labeled guanidinohydantoin from guanosine oxidation with singlet oxygen: implications for structure and mechanism J. Am. Chem. Soc. 125 2003 13926 13927
7. C. Sheu, and C.S. Foote Photosensitized oxygenation of a 7,8-dihydro-8-oxoguanosine derivative: formation of dioxetane and hydroperoxide intermediates J. Am. Chem. Soc. 117 1995 474 477
8. C. Sheu, and C.S. Foote Reactivity toward singlet oxygen of a 7,8-dihydro-8-oxoguanosine ("8-hydroxyguanosine") formed by photooxidation of a guanosine derivative J. Am. Chem. Soc. 117 1995 6439 6442
9. W. Adam, C.R. Saha-Möller, and A. Schönberger Photooxidation of 8-oxo-7,8-dihydro-2′-deoxyguanosine by thermally generated triplet-excited ketones from 3-(hydroxymethyl)-3,4,4-trimethyl-1,2-dioxetane and comparison with type I and type II photosensitizers J. Am. Chem. Soc. 118 1996 9233 9238
10. S. Raoul, and J. Cadet Photosensitized reaction of 8-oxo-7,8-dihydro- 2′-deoxyguanosine: identification of 1-(2-deoxy-β-d-erythro- pentofuranosyl)cyanuric acid as the major singlet oxygen oxidation product J. Am. Chem. Soc. 118 1996 1892 1898
11. R.P. Hickerson, F. Prat, J.G. Muller, C.S. Foote, and C.J. Burrows Sequence and stacking dependence of 8-oxoguanine oxidation: comparison of one-electron vs singlet oxygen mechanisms J. Am. Chem. Soc. 121 1999 9423 9428
12. J.C. Niles, S. Burney, S.P. Singh, J.S. Wishnok, and S.R. Tannenbaum Peroxynitrite reaction products of 3′,5′-di-O-acetyl-8-oxo-7,8- dihydro-2′-deoxyguanosine Proc. Natl. Acad. Sci. USA 96 1999 11729 11734
13. V. Duarte, J.G. Muller, and C.J. Burrows Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8- oxoguanine Nucleic Acids Res. 27 1999 496 502
14. M.D. Leipold, J.G. Muller, C.J. Burrows, and S.S. David Removal of hydantoin products of 8-oxoguanine oxidation by the Escherichia coli DNA repair enzyme, FPG Biochemistry 39 2000 14984 14992
15. W. Luo, J.G. Muller, E.M. Rachlin, and C.J. Burrows Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine Org. Lett. 2 2000 613 616
16. W. Luo, J.G. Muller, E.M. Rachlin, and C.J. Burrows Characterization of hydantoin products from one-electron of 8-oxo-7,8-dihydroguanosine in a nucleoside model Chem. Res. Toxicol. 14 2001 927 938
17. V. Duarte, D. Gasparutto, L.F. Yamaguchi, J.-L. Ravanat, G.R. Martinez, M.H.G. Medeiros, P. Di Mascio, and J. Cadet Oxaluric acid as the major product of singlet oxygen-mediated oxidation of 8-oxo-7,8-dihydroguanine in DNA J. Am. Chem. Soc. 122 2000 12622 12628
18. 18O]-Labeled singlet oxygen as a tool for mechanistic studies of 8-oxo-7,8-dihydroguanine oxidative damage: detection of spiroiminodihydantoin, imidazolone and oxazolone derivatives Biol. Chem. 383 2002 607 617
19. H. Ikeda, and I. Saito 8-Methoxydeoxyguanosine as an effective precursor of 2-aminoimidazolone, a major guanine oxidation product in one-electron oxidation of DNA J. Am. Chem. Soc. 121 1999 10836 10837
20. W. Luo, J.G. Muller, and C.J. Burrows The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine Org. Lett. 3 2001 2801 2804
21. 18O-labeled singlet oxygen for mechanistic studies J. Am. Chem. Soc. 122 2000 10212 10213
22. C. Pierlot, J.M. Aubry, K. Briviba, H. Sies, and P. Di Mascio Naphthalene endoperoxides as generators of singlet oxygen in biological media Methods Enzymol. 319 2000 3 20
23. C. Vialas, G. Pratviel, C. Claparols, and B. Meunier Efficient oxidation of 2′-deoxyguanosine by Mn-TMPyP/KHSO5 to imidazolone dIz without formation of 8-oxo-dG J. Am. Chem. Soc. 120 1998 11548 11553
24. K. Kohda, H. Tsunomoto, Y. Minoura, K. Tanabe, and S. Shibutani Synthesis, miscoding specificity, and thermodynamic stability of oligodeoxynucleotide containing 8-methyl-2′-deoxyguanosine Chem. Res. Toxicol. 9 1996 1278 1284
25. D. Gasparutto, M. Ait-Abbas, M. Jaquinod, S. Boiteux, and J. Cadet Repair and coding properties of 5-hydroxy-5-methylhydantoin nucleosides inserted into DNA oligomers Chem. Res. Toxicol. 13 2000 575 584
26. -) molecular oxygen in aqueous solution J. Am. Chem. Soc. 126 2004 3056 3057
27. M.E. Hosford, J.G. Muller, and C.J. Burrows Spermine participates in oxidative damage of guanosine and 8-oxoguanosine leading to deoxyribosylurea formation J. Am. Chem. Soc. 126 2004 9540 9541