Photosensitized Oxidation of Oxopurines by Rose Bengal

Photochemistry and Photobiology

Volumn 68, Issue 4, 1998, Pages 467-473

  Murgida, Daniel H ^a   Aramendía, Pedro F ^a   Erra Balsells, Rosa ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013429710     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1998.tb02501.x     Document Type: Article

References (35)

1. Ravanat, J. L., M. Berger, F. Benard, R. Langlois, R. Quellet, J. E. van Lier and J. Cadet (1992) Phthalocyanine and naphthalocyanine photosensitized oxidation of 2′-deoxyguanosine: distinct type I and type II products. Photochem. Photobiol. 55, 809-814.
2. Morin, B. and J. Cadet (1994) Benzophenone photosensitization of 2′-N-deoxyguanosine: characterization of the 2R and 2S diastereoisomers of 1-(2-deoxy-b-erythro-pentafuranosyl)-2-methoxy-4,5-imidazolidinedione. A model system for the investigation of photosensitized formation of DNA-protein crosslinks. Photochem. Photobiol. 60, 102-109.
3. Cadet, J., M. Berger, G. W. Buchko, P. C. Joshi, S. Raoul and J. L. Ravanat (1994) 2,2-Diamino-4-[(3,5-di-O-acetyl-2-deoxy-β-D-erythro-peritafuranosyl)amino]- 5-(2H)-oxazolone: a novel and predominant radical oxidation product of 3′,5′-di-O-acetyl-2′-deoxyguanosine. J. Am. Chem. Soc. 116, 7403-7404.
4. Morin, B. and J. Cadet (1995) Chemical aspects of the benzophenone-photosensitized formation of two lysine-2′-deoxyguanosine cross links. J. Am. Chem. Soc. 117, 12408-12415.
5. Raoul, S. and J. Cadet (1996) Photosensitized reaction of 8-oxo-7,8-dihydro-2′-deoxyguanosine: identification of 1-(2-deoxy-β-D-erythro-pentofuranosil)cyanuric acid as the major singlet oxygen oxidation product. J. Am. Chem. Soc. 118, 1892-1898.
6. Adam, W., C. R. Saha-Möller, A. Schönberger, M. Berger and J. Cadet. (1995) Formation of 7,8-dihydro-8-oxoguanine in the 1,2-dioxetane-induced oxidation of calf thymus DNA: evidence for photosensitized DNA damage by thermally generated triplet ketones in the dark. Photochem. Photobiol. 62, 231-238.
7. Adam, W., C. R. Saha-Möller and A. Schönberger (1996) Photooxidation of 8-oxo-7,8-dihydro-2′-deoxyguanosine by thermally generated triplet-excited ketones from 3-(hydroxymetlhyl)-3,4.4-trimethyl-1,2-dioxetane and comparison with type I and type II photosensitizers. J. Am. Chem. Soc. 118, 9233-9238.
8. Adam, W., C. R. Saha-Möller and A. Schönberger (1997) Type I and type II photosensitized oxidative modification of 2′-deoxyguanosine (dGuo) by triplet-excited ketones generated thermally from the 1,2-dioxetane HTMD. J. Am. Chem. Soc. 119, 719-723.
9. Sheu, C. and C. S. Foote (1993) Endoperoxide formation in a guanosine derivative. J. Am. Chem. Soc. 115, 10446-10447.
10. Sheu, C. and C. S. Foote (1995) Photosensitized oxygenation of a 7,8-dihydro-8-oxoguanosine derivative. Formation of dioxetane and hydroperoxide intermediates. J. Am. Chem. Soc. 117, 474-477.
11. Sheu, C. and C. S. Foote (1995) Reactivity towards singlet oxygen of a 7,8-dihydro-8-oxoguanosine ("8-hydroxyguanosine") formed by photooxidation of a guanosine derivative. J. Am. Chem. Soc. 117, 6439-6442.
12. Devasagayam, T. P. A., S. Steenken, M. W. Obendorf, W. A. Schulz and H. Sies (1991) Formation of 8-hydroxy(deoxy)guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen. Biochemistry 25, 3283-6289.
13. Boiteux, S., E. Gajewski, J. Laval and M. Dizdaroglu (1992) Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): excision of purine lesions in DNA produced by ionizing radiation or photosensitization. Biochemistry 31, 106-110).
14. Simon, M. I. and H. Van Vunakis (1964) The dye-sensitized photooxidation of purine and pyrimidine derivatives. Arch. Biochem. Biophys. 105, 197-206.
15. Clennan, E. L. (1991) Synthetic and mechanistic aspects of 1,3-diene photooxidation. Tetrahedron 47, 1343-1382.
16. Murgida, D. H., P. F. Aramendía and R. Erra-Balsells (1998) Benzophenone photosensitized reactions of xanthinic compounds. A mechanistic study. Photochem. Photobiol. 67, 487-494.
17. Murgida, D. H., G. M. Bilmes and R. Erra-Balsells (1994) Photoacoustic determination of energy content and quantum yield of formation of transient states. J. Phys. 4, C7-417-420.
18. Murgida, D. H., G. M. Bilmes and R. Erra-Balsells (1996) New photocalorimetric references for UV excitation. Chem. Phys. Lett. 250, 198-202.
19. Murgida, D. H., G. M. Bilmes and R. Erra-Balsells (1996) A photophysical study of purines and theophylline by using laser induced photoacoustic spectroscopy. Photochem. Photobiol. 64, 777-784.
20. Acs, A., R. Schmidt and H. D. Brauer (1983) Mesodiphenylhelianthrene. The most reactive singlet oxygen acceptor. Photochem. Photobiol. 38, 527-531.
21. Brauer H. D., R. Schmidt, G. Gauglitz and S. Hubig (1983) Chemical actinometry in the visible (475-610 nm) by mesodiphenylhelianthrene. Photochem. Photobiol. 37, 595-598.
22. Autodesk (1996) Hyperchem release 5.0 for windows. Autodesk, Ontario, Canada.
23. Wilkinson, F., W. P. Helman and A. B. Ross (1995) Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J. Phys. Chem. Ref. Data 24, 663-1021.
24. Lambert, C. R. and I. E. Kochevar (1996) Does rose bengal triplet generate superoxide anion? J. Am. Chem. Soc. 118, 3297-3298.
25. Wintgens, V., J. C. Scaiano, S. M. Linden and D. C. Neckers (1989) Transient phenomena in the laser flash photolysis of the rose bengal C-2′ ethyl ester C-6 sodium salt. J. Org. Chem. 54, 5242-5246.
26. Lambert, C., T. Sarna and T. G. Truscott (1990) Rose bengal radicals and their reactivity. J. Chem. Soc. Faraday Trans. 86, 3879-3882.
27. Stiel, H., K. Teuchner, A. Paul, D. Leupold and I. E. Kochevar (1996) Quantitative comparision of excited state properties and intensity-dependent photosensitization by rose bengal. J. Photochem. Photobiol. B Biol. 33, 245-254.
28. Murov, S. L., I. Carmichael and G. L. Hug (1993) Handbook of Photochemistry. Marcel Dekker, New York.
29. Gorman, A. A. and M. A. J. Rodgers (1989) Singlet oxygen. In Handbook of Organic Photochemistry, Vol. II (Edited by J. C. Scaiano), Chapter 10. CRC Press, Boca Raton, FL.
30. Reichardt, C. (1979) Solvent Effects in Organic Chemistry. Verlag Chemie, Weinheim.
31. Marcus, Y. (1993) The properties of organic liquids that are relevant to their use as solvating solvents. Chem. Soc. Rev., pp. 409-416.
32. Wilkinson, F., W. Phillip Helman and A. B. Ross (1993) Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 22, 113-262.
33. Manring, L. E., R. C. Kanner and C. S. Foote (1983) Chemistry of singlet oxygen. 43. Quenching by conjugated olefins. J. Am. Chem. Soc. 105, 4707-4710.
34. Manring, L. E. and C. S. Foote (1983) Chemistry of singlet oxygen. 44. Mechanism of photooxidation of 2,5-dimethylhexa-2,4-diene. J. Am. Chem. Soc. 105, 4710-4717.
35. Liang, J. L., C. L. Gu, M. L. Kacher and C. S. Foote (1983) Chemistry of singlet oxygen. 45. Mechanism of the photooxidation of sulfides. J. Am. Chem. Soc. 105, 4717-4721.