2,2-Diamino-4-[(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)anrino]-5-(2H)-oxazolone: A Novel and Predominant Radical Oxidation Product of 3',5'-Di-O-acetyl-2'-deoxyguanosine

Journal of the American Chemical Society

Volumn 116, Issue 16, 1994, Pages 7403-7404

  Cadet, Jean ^a   Berger, Maurice ^a   Raoul, Sébastien ^a   Buchko, Garry W ^b   Joshi, Prakash C ^c   Ravanat, Jean Luc ^d  

^a CEA GRENOBLE   (France)

^b SIMON FRASER UNIVERSITY   (Canada)

^c CSIR INDIAN INSTITUTE OF TOXICOLOGY RESEARCH   (India)

^d NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2,2 DIAMINO 4 [(3,5 DI O ACETYL 2 DEOXY BETA D ERYTHROPENTOFURANOSYL)AMINO] 5(2H) OXAZOLONE; DEOXYGUANOSINE DERIVATIVE; DNA BASE; OXAZOLONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DNA SEQUENCE; DRUG SYNTHESIS; HYDRATION; NUCLEOTIDE METABOLISM; OXIDATION; PHOTOSENSITIVITY;

EID: 0027934952     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00095a052     Document Type: Article

References (35)

1. For recent reviews, see: (a) Cadet, J.; Vigny, P. In Bioorganic Photochemistry, Morrison H., Ed.; Wiley: New York, 1990, Vol. 1, pp 1-272.
2. Dizdaroglu, M. Free Rad. Biol. Med. 1991, 10, 225-242.
3. Angelov, D.; Berger, M.; Cadet, J.; Getoff, N.; Keskinova, E.; Solar, S. Rad. Phys. Chem. 1991, 37, 717-727.
4. Cadet, J. In DNA Adducts: Identification, and Biological Significance; Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., Bartsch, H., Eds.; IARC Publications: Lyon, Vol. 125. in cress.
5. For reviews see, for example: (a) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor & Francis: London, 1987.
6. Steenken, S. Chem. Rev. 1989, 89, 503-520.
7. Téoule, R.; Cadet, J. Mol. Biol. Biochem. Biophys. 1978, 27, 171-203.
8. Decarroz, C.; Wagner, J. R.; van Lier, J. E.; Murali Krishna, C.; Riesz, P.; Cadet, J. Int. J. Radiat. Biol. 1986, 50, 491-505.
9. Cadet, J.; Berger, M.; Decarroz, C.; Mouret, J.-F.; van Lier, J. E.; Wagner, R. J. J. Chim. Phys. 1991, 88, 1021-1042.
10. Decarroz, C.; Wagner, J. R.; Cadet, J. Free Rad. Res. Commun. 1987, 2, 295-301.
11. Wagner, J. R.; van Lier, J. E.; Decarroz, C.; Berger, M.; Cadet, J. Methods Enzvmol. 1990, 186. 502-511.
12. Cadet, J.; Berger, M. Int. J. Radiat. Biol. 1985, 47, 127-143.
13. Berger, M.; de Hazen, M.; Nejjari, A.; Fournier, J.; Guignard, J.; Pezerat, H.; Cadet, J. Carcinogenesis 1993, 14, 41-46.
14. Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 699-704.
15. Kasai, H.; Yamaizumi, Z.; Berger, M.; Cadet, J. J. Am. Chem. Soc. 1992, 114, 9692-9694.
16. Cadet, J.; Decarroz, C.; Wang, S. Y.; Midden, W. R. Isr. J. Chem. 1983, 23, 420-429.
17. Buchko, G. W.; Cadet, J. Can. J. Chem. 1992, 70, 1827-1832.
18. 2), 117.5 (NH), 1.91.0 (N=C). It should be added that a brown coloration was observed for 10 after spraying the silica gel TLC plates with the hydroxylamineiron(III) chloride dyeing reagent which is used for the detection of lactones (Whittaker, V. P.; Wijesundera, S. Biochem. J. 1952, 51, 348-353). (b) However, as suggested by a reviewer we cannot rule out the possibility of the occurrence of an equilibrium between the orthocarbonate 10 and its ring open tautomer which exhibits a free carboxylic acid group.
19. O'Neill, P. Radial. Res. 1983, 96, 198-210.
20. O'Neill, P.; Chapman, P. W. Int. J. Radiat. Biol. 1985, 47, 71-80.
21. Candeias,L. P.; Steenken, S. J. Am. Chem. Soc. 1989, 111, 1094-1099.
22. Bachler, V.; Hildenbrand, K. Rod. Phys. Chem. 1992, 40, 59-68.
23. O'Neill, P.; Davies, S. E. Int. J. Radiat. Biol. 1987, 52, 577-587.
24. Simic, M. G.; Jovanovic, S. V.; Al-Sheikhly Free Rad. Res. Commun. 1989, 6, 113-115.
25. Schulte-Frohlinde, D.; Simic, M. G.; Görner, H. Photochem. Photobiol. 1990, 52, 1137-1151.
26. Mouret, J.-F.; Berger, M.; Anselmino, C.; Polverelli, M.; Cadet, J. J. Chim. Phys. 1991, 85, 1053-1061.
27. Jovanovic, S. V.; Simic, M. G. Biochtm. Biophys. Acta 1989, 1008, 39-44.
28. Similarly, the 2R and 25 diastereomer of 1-(2-deoxy-β-D-erythro-pentofuranosyl)-2-methoxy-4,5-imidazolidinedione were generated upon ben-zophenone photosensitization of 2'-deoxyguanosine in methanol-water solutions (Cadet, J.; Buchko, G. W.; Berger, M.; Morin, B.; Ravanat, J.-L. Photochem. Photobiol. 1993, 57, 82s). This constitutes a relevant model system for investigating the radiation-induced and photosensitized formation of DNA-protein cross-links.
29. Buchko,G. W.; Cadet, J.; Ravanat, J.-L.; Labataille, P. Int. J. Radiat. Biol. 1993, 63, 669-676.
30. Croke, D. T.; Blau, W.; OhUigin, C.; Kelly, J. M.; McConnell, D. J. Photochem. Photobiol. 1988, 47, 527-536.
31. Sage, E.; Le Doan, T.; Boyer, V.; Helland, D. E.; Kittler, L.; Hélène, C.; Moustacchi, E. J. Mol. Biol. 1989, 209, 297-314.
32. Rokita, S. E.; Prusiewicz, S.; Romero-Fredes, L. J. Am. Chem. Soc. 1990, 112, 3616-3621.
33. Chen, X.; Burrows, C. J.; Rokita, S. E. J. Am. Chem. Soc. 114, 322-325.
34. Dunn, D. A.; Lin, V. H.; Kochevar, I. Biochemistry 1992, 31, 11620-11625.
35. Leteurtre, F.; Fesen, M.; Kohlhagen, G.; Kohn, K. W.; Pommier, Y. Biochemistry 1993, 32, 8955-8962.