Modification of DNA bases by photosensitized one-electron oxidation

International Journal of Radiation Biology

Volumn 75, Issue 5, 1999, Pages 571-581

  Douki, T ^a   Cadet, J ^a  

^a INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE; DEOXYRIBONUCLEOSIDE; DNA; DNA BASE; GUANINE; GUANINE DERIVATIVE; HYDROXYL RADICAL; IMIDAZOLE DERIVATIVE; MENADIONE; OXAZOLONE; PYRIMIDINE; RIBOFLAVIN;

ARTICLE; CHEMICAL STRUCTURE; DNA DAMAGE; DNA DEGRADATION; DNA DETERMINATION; DNA MODIFICATION; DNA SEQUENCE; ELECTRON TRANSPORT; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION; OXIDATION REDUCTION POTENTIAL; PHOTOSENSITIZATION; PRIORITY JOURNAL; ULTRAVIOLET A RADIATION;

BENZOPHENONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; GAMMA RAYS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GUANINE; OXIDATION-REDUCTION; PHOTOSENSITIZING AGENTS; RIBOFLAVIN; VITAMIN K;

EID: 0032980386     PISSN: 09553002     EISSN: None     Source Type: Journal    
DOI: 10.1080/095530099140212     Document Type: Article

References (53)

1. ADAM, W., SAHAMOLLER, C. R. and SCHONBERGER, A., 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. Journal of the American Chemical Society, 119, 719-723.
2. AMES, B. A., GOLD, L. S. and WILLET, W. C., 1995, The causes and prevention of cancer. Proceedings of the National Academy of Sciences, U S A, 92, 5258-5265.
3. ANGELOV, D., SPASSKY, A., BERGER, M. and CADET, J., 1997, High-intensity UV laser photolysis of DNA and purine 2′-deoxyribonucleosides: formation of 8-oxopurine damage and oligonucleotide strand cleavage as revealed by HPLC and gel electrophoresis studies. Journal of the American Chemical Society, 119, 11373-11380.
4. BREEN, A. P. and MURPHY, J. A., 1995, Reactions of oxyl radicals with DNA. Free Radical Biology and Medicine, 18, 1033-1077.
5. BREIMER, L. H. and LINDAHL, T., 1985, Thymine lesions produced by ionizing radiation in double-stranded DNA. Biochemistry, 24, 4018-4022.
6. CADET, J., BERGER, M., BUCHKO, G. W., JOSHI, P. C., RAOUL, S. and RAVANAT, J.-L., 1994, 2,2-Diamino-4-[(3,5-di-O-acetyl-2-deoxy-b-D-erythro-pentofuranosyl)amino]-5-(2H)-oxazolone: a novel and predominant radical oxidation product of 3′,5′-di-O-acetyl-2′-deoxyguanosine. Journal of the American Chemical Society, 116, 7403-7404.
7. CADET, J., BERGER, M., DOUKI, T. and RAVANAT, J.-L., 1997a, Oxidative damage to DNA: formation, measurement and biological significance. Reviews in Physiological and Biochemical Pharmacology, 131, 1-87.
8. CADET, J., DOUKI, T. and RAVANAT, J.-L., 1997b, Artifacts associated with the measurement of oxidized DNA bases. Environmental Health Perspectives, 105, 1034-1039.
9. CADET, J. and TEOULE, R., 1978, Comparative study of oxidation of nucleic acid components by hydroxyl radicals, singlet oxygen and Superoxide anion radicals. Photochemistry and Photobiology, 28, 661-667.
10. CANDEIAS, L. P. and STEENKEN, S., 1992, Electron transfer in di(deoxy)nucleoside phosphates in aqueous solution: rapid migration of oxidative damage (via adenine) to guanine. Journal of the American Chemical Society, 115, 2437-2440.
11. CHARLIER, M. and HÉLÈNE, C., 1972, Photochemical reactions of aromatic ketones with nucleic acids and their components-III. Chain breakage and thymine dimerization in benzophenone photosensitized DNA. Photochemistry and Photobiology, 51, 527-536.
12. COLSON, A. O. and SEVILLA, M. D., 1995, Elucidation of primary radiation damage in DNA through application of ab initio molecular orbital theory. International Journal of Radiation Biology, 67, 621-645.
13. CULLIS, P. M., MALONE, M. E. and MERSON-DAVIES, L. A., 1996, Guanine radical cations are precursors of 7,8-dihydro-8-oxo-2′-deoxyguanosine but are not precursors of immediate strand breaks. Journal of the American Chemical Society, 118, 2775-2781.
14. DECARROZ, C., WAGNER, J. R. and CADET, J., 1987, Specific deprotonation reactions of the pyrimidine radical cation resulting from the menadione mediated photosensitization of 2′-deoxycytidine. Free Radical Research Communications, 2, 295-301.
15. DECARROZ, C., WAGNER, J. R., VAN LIER J. E., MURALI, K. C., RIESZ, P. and CADET, J., 1986, Sensitized photo-oxidation of thymidine by 2-methyl-1,4-naphtoquinone. Characterization of stable products. International Journal of Radiation Biology, 50, 491-505.
16. DEFLORA, S., IZZOTTI, A., RANDERATH, K., RANDERATH, E., BARTSCH, H., NAIR, J., BALANSKY, R., VANSCHOOTEN, F., DEGAN, P., FRONZA, G., WALSH, D. and LEWTAS, J., 1996, DNA adducts and chronic degenerative diseases. Pathogenetic relevance and implications in preventive medicine. Mutation Research, 366, 197-238.
17. DELATOUR, T., DOUKI, T., D'HAM, C. and CADET, J., 1998, Photosensitization of thymine nucleobase by benzophenone through energy transfer, hydrogen abstraction and one-electron oxidation. Journal of Photochemistry and Photobiology B: Biology, 44, 191-198.
18. DIZDAROGLU, M. and GAJEWSKI, E., 1990, Selected-ion mass spectrometry: assays of oxidative DNA damage. Methods in Enzymology, 186, 530-544.
19. DOUKI, T. and CADET, J., 1996, Peroxynitrite mediated oxidation of purine bases of nucleosides and isolated DNA. Free Radical Research, 24, 369-380.
20. DOUKI, T., DELATOUR, T., BIANCHINI, F. and CADET, J., 1996b, Observation and prevention of an artefactual formation of oxidized DNA bases and nucleosides in the GC-EIMS method. Carcinogenesis, 17, 347-352.
21. DOUKI, T., DELATOUR, T., PAGANON, F. and CADET, J., 1996a, Measurement of oxidative damage at pyrimidine bases in γ-irradiated DNA. Chemical Research in Toxicology, 9, 1145-1151.
22. DOUKI, T., MARTINI, R., RAVANAT, J.-L., TURESKY, R. J. and CADET, J., 1997, Measurement of 2,6-diamino-4-hydroxy-5 formamidopyrimidine and 8-oxo-7,8-dihydroguanine in isolated DNA exposed to gamma radiation in aqueous solution. Carcinogenesis, 18, 2385-2391.
23. EPE, B., PFLAUM, M. and BOITEUX, S., 1993, DNA damage induced by photosensitizers in cellular and cell-free systems. Mutation Research, 299, 135-145.
24. FLOYD, R. A., WEST, M. S., ENEFF, K. L. and SCHNEIDER, J. E., 1989, Methylene blue plus light mediates 8-hydroxyguanine formation in DNA. Archives of Biochemistry and Biophysics, 273, 106-111.
25. FLOYD, R. A., WEST, M. S., ENEFF, K. L. and SCHNEIDER, J. E., 1990, Mediation of 8-hydroxy-guanine formation in DNA by thiazin dyes plus light. Free Radical Biology and Medicine, 8, 327-330.
26. GREENSTOCK, C. L. and JOHNS, H. E., 1968, Photosensitized dimerization of pyrimidines. Biochemical and Biophysical Research Communications, 30, 21-27.
27. GUT, I. G., WOOD, P. D. and REDMOND, R. W., 1996, Interaction of triplet photosensitizers with nucleotides and DNA in aqueous solution at room temperature. Journal of the American Chemical Society, 118, 2366-2373.
28. HALL, D. B., HOLMLIN, R. E. and BARTON, J. K., 1996, Oxidative DNA damage through long range electron transfer. Nature, 382, 731-735.
29. HÉLÈNE, C. and CHARLIER, M., 1971, Photosensitized reactions in nucleic acids. Photosensitized formation and splitting of pyrimidine dimers. Biochimie, 53, 1175-1180.
30. KASAI, H., LIDA, A., YAMAIZUMI, Z., NISHIMUR, S. and TANOOKA, H., 1990, 5-Formyldeoxyuridine: a new type of DNA damage induced by ionizing radiation and its mutagenicity to Salmonella strain TA102. Mutation Research, 243, 249-253.
31. KASAI, H., TANOOKA, H. and NISHIMURA, S., 1984, Formation of 8-hydroxyguanine residues in DNA by X irradiation. Gann, 75, 1037-1039.
32. KASAI, H., YAMAIZUMI, Z., BERGER, M. and CADET, J., 1992, Photosensitized formation of 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-hydroxy-2′-deoxyguanosine) in DNA by riboflavin: a non singlet oxygen mediated reaction. Journal of the American Chemical Society 114, 9692-9094.
33. KINO, K., SAITO, I. and SUGIYAMA, H., 1990, Product analysis of GG-specific photooxidation of DNA via electron transfer: 2-aminoimidazolone as a major guanine oxidation product. Journal of the American Chemical Society, 120, 7373-7374.
34. LEWIS, F. D., WU, T. F., ZHANG, Y. F., LETSINGER, R. L., GREENFIELD, S. R. and WASIELEWSKI, M. R., 1997, Distance-dependent electron transfer in DNA hairpins. Science, 277, 673-676.
35. LINDAHL, T., 1993, Instability and decay of the primary structure of DNA, Nature, 362, 709-715.
36. MELVIN, T., BOTCHWAY, S., PARKER, A. W. and O'NEIL, L. P., 1993, Migration of photoinduced oxidative damage in models for DNA. Journal of the Chemical Society - Chemical Communications, 653-654.
37. MELVIN, T., CUNNIFFE, S., PAPWORTH, D., ROLDANARJONA, T. and O'NEILL, P., 1997, Irradiation of DNA with 193 nm light yields formamidopyrimidine-DNA glycosylase (Fpg) protein-sensitive lesions. Photochemistry and Photobiology, 65, 660-665.
38. MORI, T., TANO, K., TAKIMOTO, K. and UTSUMI, H., 1998, Formation of 8-hydroxyguanine and 2,6-diamino-4-hydroxy-5-formamidopyrimidine in DNA by riboflavin mediated photosensitization. Biochemical and Biophysical Research Communications, 242, 98-101.
39. PIETTE, J., CALBERG-BACQ, C. M. and VAN DE VORST, A., 1981, Alteration of guanine residues during proflavine mediated photosensitization of DNA. Photochemistry and Photobiology, 33, 325-333.
40. PORTER, G. and WILKINSON, F., 1961, Primary photochemical processes in aromatic molecules. Journal of the Chemical Society Transactions of the Faraday Society, 58, 1686-1694.
41. RAOUL, S. and CADET, J., 1996, Photosensitized reaction of 8-oxo-7,8-dihydro-2′-deoxyguanosine: identification of 1-(2-deoxy-b-D-erythro-pentofuranosyl)cyanuric acid as the major singlet oxygen oxidation product. Journal of the American Chemical Society, 118, 1892-1898.
42. RAVANAT, J.-L., BERGER, M., BENARD, F., LANGLOIS, R., OUELLET, R., VAN LIER, J. E. and CADET, J., 1992, Phtahlocyanine and naphtalocyanine photosensitized oxidation of 2′-deoxyguanosine: distinct type I and type II products. Photochemistry and Photobiology, 55, 809-814.
43. RAVANAT, J.-L, and CADET, J., 1995, Reaction of singlet oxygen with 2′-deoxyguanosine and DNA. Isolation and characterization of the main oxidation products. Chemical Research in Toxicology, 8, 379-388.
44. RAVANAT, J.-L., TURESKY, R. J., GREMAUD, E., TRUDEL, L. J. and STADLER, R. H., 1995, Determination of 8-Oxoguanine in DNA by gas chromatography-mass spectrometry and HPLC-electrochemical detection: overestimation of the background level of the oxidized base by the gas chromatography-mass spectrometry assay. Chemical Research in Toxicology, 8, 1039-1045.
45. RILEY, P. A., 1994, Free radicals in biology: oxidative stress and the effects of ionizing radiation. International Journal of Radiation Biology, 65, 27-33.
46. SAITO, I., TAKAYAMA, M., SUGIYAMA, H. and NAKATANI, K., 1995, Photoinduced DNA cleavage via electron transfer: demonstration that guanine residues located 5′ to guanine are the most electron-donating sites. Journal of the American Chemical Society, 117, 6406-6407.
47. SCHENCK, G. O., BECKER, H.-D., SCHULTE-ELTE, K.-H. and KRAUCH, C. H., 1963, Mit Benzophenon photosensibilisierte Autoxydation von sek. Alkoholen und Äthern darstellung von a-Hydroperoxyden. Chemische Berichte, 96, 509-516.
48. SHEU, C. and FOOTE, C. S., 1995a, Photosensitized oxygenation of 1 7,8-dihydro-8-oxoguanosine derivative. Formation of a dioxetane and hydroperoxide intermediates. Journal of the American Chemical Society, 117, 474-477.
49. SHEU, C. and FOOTE, G. S., 1995b, Reactivity toward singlet oxygen of a 7,8-dihydro-8-oxo-guanosine ('8-hydroxyguanosine') formed by photooxidation of a guanosine derivative. Journal of the American Chemical Society, 117, 6439-6442.
50. STEENKEN, S., 1989, Purine bases, nucleosides, and nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and c-and OH adducts, Chemical Reviews, 89, 503-520.
51. SWARTS, S. G., SMITH, G. S., MIAO, L. and WHEELER, K. T., 1996, Effects of formic acid hydrolysis on the quantitative analysis of radiation-induced DNA base damage product assayed by gas chromatography/mass spectrometry. Radiation and Environmental Biophysics, 35, 41-53.
52. TOYOKUNI, S., 1996, Iron-induced carcinogenesis: the role of redox regulation. Free Radical Biology and Medicine, 20, 553-566.
53. WARD, J. F., 1995, Radiation mutagenesis: the initial DNA lesions responsible. Radiation Research, 142, 362-368.