Photosensitization of thymine nucleobase by benzophenone through energy transfer, hydrogen abstraction and one-electron oxidation

Journal of Photochemistry and Photobiology B: Biology

Volumn 44, Issue 3, 1998, Pages 191-198

  Delatour, T ^a   Douki, T ^a   D'Ham, C ^a   Cadet, J ^a  

^a CEA GRENOBLE   (France)

Author keywords

Benzophenone; Photosensitization; Thymine nucleobase

Indexed keywords

BENZOPHENONE; HYDROGEN; MENADIONE; THYMIDINE;

ARTICLE; ENERGY TRANSFER; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PHOTOSENSITIZATION; PRIORITY JOURNAL;

EID: 0032584484     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(98)00142-0     Document Type: Article

References (63)

1. [1] J. Cadet, P. Vigny, The photochemistry of nucleic acids, in: H. Morrison (Ed.), Bioorganic Chemistry, vol. 1, Wiley, New York, 1990, pp. 1-272.
2. [2] J. Cadet, DNA damage caused by oxidation, deamination, ultraviolet radiation and photoexcited psoralen, in: K. Hemminki, A. Dipple, D.G.E. Shuker, F.F. Kadlubar, D. Segerbäck, H. Bartsch (Eds), DNA Adducts: Identification and Biological Significance, IARC Scientific Publications, Lyon, France, 1994, pp. 245-276.
3. [3] J.-S. Taylor, Unraveling the molecular pathway from sunlight to skin cancer, Acc. Chem. Res. 27 (1994) 76-82.
4. [4] J.-S. Taylor, DNA, sunlight and skin cancer, Pure Appl. Chem. 67 (1995) 183-190.
5. [5] J. Cadet, M. Berger, T. Douki, B. Morin, S. Raoul, J.-L. Ravanat, S. Spinelli, Effects of UV and visible radiation on DNA - final base damage, Biol. Chem. 378 (1997) 1275-1286.
6. [6] A. Rörsch, R. Barkes, J. Ijlstra, W. Berends, The effect of UV light on some components of the nucleic acids. I. Uracil, thymine, Rec. Trav. Chim. Pays Bas 77 (1958) 423-429.
7. [7] B.H. Jennings, S.-C. Pastra, J.L. Wellington, Photosensitized dimerization of thymine, Photochem. Photobiol. 11 (1970) 215-226.
8. [8] F.-T. Liu, N.C. Yang, Photochemistry of cytosine derivatives. 1. Photochemistry of thymidylyl-(3′ → 5′)-deoxycytidine, Biochemistry 17 (1978) 4865-4876.
9. [9] D.P. Hollis, S.Y. Wang, Structure of homodimers of thymine and dimethylthymine. A nuclear magnetic resonance study, J. Org. Chem. 32 (1967) 1620-1622.
10. [10] D.P. Hollis, in: S.Y. Wang (Ed.), Photochemistry and Photobiology of Nucleic Acids, vol. 1, Academic Press, New York, 1976, pp. 447-481.
11. [11] N. Camerman, A. Camerman, Photodimer of thymine in ultraviolet-irradiated DNA: proof of structure by X-ray diffraction, Science 160 (1968) 1451-1452.
12. [12] N. Camerman, S.C. Nyburg, The crystal and molecular structure of a thymine photodimer (dimer 'E'), Acta Crystallogr. B25 (1969) 388-394.
13. [13] F. Hruska, L. Voituriez, A. Grand, J. Cadet, Molecular structure of the cis-syn photodimer of d(TpT) (cyanoethyl ester), Biopolymers 25 (1986) 1399-1417.
14. [14] J. Cadet, J. Ulrich, R. Téoule, Isomerization and new specific synthesis of thymine glycol, Tetrahedron 31 (1975) 2057-2061.
15. [15] J. Cadet, R. Téoule, Oxidation of thymidine by permanganate in neutral and alkaline aqueous solutions, J. Chem. Res. (1977) 296-297.
16. 13C NMR study of the radiation-induced degradation products of 2′-deoxythymidine derivatives: N-(2-deoxy-β-D-erythropentofuranosyl)-formamide, Can. J. Chem. 59 (1981) 3313-3318.
17. [17] L.R. Subbaram, J. Subbaram, E.J. Behrman, The reaction of oxoosmium(VI) pyridine complexes with thymine glycols, J. Org. Chem. 38 (1973) 1499-1504.
18. [18] C. Decarroz, J.R. Wagner, J.E. van Lier, C. Murali Krishna, P. Riesz, J. Cadet, Sensitized photo-oxidation of thymidine by 2-methyl-1,4-naphthoquinone. Characterization of the stable photoproducts, Int. J. Radiat. Biol. 50 (1986) 491-505.
19. [19] C. Bienvenu, J.R. Wagner, J. Cadet, Photosensitized oxidation of 5-methyl-2′-deoxycytidine by 2-methyl-1,4-naphthoquinone: characterization of 5-(hydroxymethyl)-2′-deoxycytidine and stable methyl group oxidation products, J. Am. Chem. Soc. 118 (1996) 11406-11411.
20. [20] C. Bienvenu, J. Cadet, Synthesis and kinetic study of the deamination of the cis diastereosiomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2′-deoxycytidine, J. Org. Chem. 61 (1996) 2632-2637.
21. [21] J. Cadet, R. Téoule, Radiolyse gamma de la thymidine en solution aqueuse aérée. III. Aspects quantitatifs et mécanisme, Bull. Soc. Chim. Fr. 4 (1975) 891-895.
22. [22] J. Cadet, M. Berger, G.W. Buchko, P.C. Joshi, S. Raoul, J.-L. Ravanat, 2,2-Diamino-4-[(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino]-5-(2H)-oxazolone: a novel and predominant radical oxidation product of 3′,5′-di-O-acetyl-2′-deoxyguanosine, J. Am. Chem. Soc. 116 (1994) 7403-7404.
23. [23] L.P. Candeias, S. Steenken, Structure and acid-base properties of one-electron-oxidized deoxyguanosine, guanosine, and 1-methylguanosine, J. Am. Chem. Soc. 111 (1989) 1094-1099.
24. [24] A.J.S.C. Vieira, S. Steenken, Pattern of OH radical reaction with adenine and its nucleosides and nucleotides. Characterization of two types of isomerie OH adduct and their unimolecular transformation reactions, J. Am. Chem. Soc. 112 (1990) 6986-6994.
25. [25] P. O'Neill, Pulse radiolytic study of the interaction of thiols and ascorbate with OH adducts of dGMP and dG: implications for DNA repair processes, Radiat. Res. 96 (1983) 198-210.
26. [26] P. O'Neill, P.W. Chapman, Potential repair of free radical adducts of dGMP and dG by a series of reductants. A pulse radiolytic study, Int. J. Radiat. Biol. 47 (1985) 71-80.
27. [27] C. Murali Krishna, C. Decarroz, J.R. Wagner, J. Cadet, P. Riesz, Menadione sensitized photooxidation of nucleic acid and protein constituents. An ESR and spin-trapping study, Photochem. Photobiol. 46 (1987) 175-182.
28. [28] R. Brossmer, D. Ziegler, Zur Darstellung heterozyklischer Aldehyde, Tetrahedron Lett. 43 (1966) 5253-5256.
29. [29] M.J. Lustig, J. Cadet, R.J. Boorstein, G.W. Teebor, Synthesis of the diastereoisomers of thymidine glycol, determination of concentrations and rates of interconversion of their cis-trans epimers at equilibrium and demonstration of differential alkali lability within DNA, Nucleic Acids Res. 20 (1992) 4839-4845.
30. [30] C.B. Reese, The chemical synthesis of oligo-and poly-nucleotides by the phosphotriester approach, Tetrahedron 34 (1978) 3143-3179.
31. [31] S.A. Narang, DNA synthesis, Tetrahedron 39 (1983) 3-22.
32. [32] J.B. Chattopadhyaya, C.B. Reese, Some observations relating to phosphorylation methods in oligonucleotide synthesis, Tetrahedron Lett. 52 (1979) 5059-5062.
33. [33] K. Miyoshi, K. Itakura, Solid-phase synthesis of polynucleotides. V. Synthesis of oligodeoxyribonucleotides by the phosphomonotriazolide method, Nucleic Acids Res., Symp. Ser. 7 (1980) 281-291.
34. [34] V.A. Efimov, S.V. Reverdatto, O.G. Chakhnakhcheva, Arylsulfonyl chlorides in the presence of N-methylimidazole as efficient condensing raegents in phosphotriester oligonucleotide synthesis, Tetrahedron Lett. (1982) 961-964.
35. [35] T. Douki, T. Delatour, F. Paganon, J. Cadet, Measurement of oxidative damage at pyrimidine bases in γ-irradiated DNA, Chem. Res. Toxicol. 9 (1996) 1145-1151.
36. 6,5′-cyclo-5,6-dihydro-2′-deoxyuridine. Novel deoxyuridine photoproducts, J. Am. Chem. Soc. 100 (1978) 6715-6720.
37. [37] J.G. Buchanan, Detection of deoxyribonucleosides on paper chromatograms, Nature 168 (1951) 1091-1092.
38. [38] D.M. Reddy, C.R. Iden, Analysis of modified deoxynucleosides by electrospray ionization mass spectrometry, Nucleosides Nucleotides 12 (1993) 815-826.
39. [39] B.R. Baker, T.J. Shwan, D.V. Santi, Non-classical antimetabolites. Inhibition by nucleoside derivatives, J. Med. Chem. 9 (1966) 66-75.
40. [40] G.I. Birnbaum, R. Deslauriers, T.-S. Lin, G.-T. Shiau, W.H. Prusoff, A novel intramolecular hydrogen bond in the crystal structure of 5-hydroxymethyl-2′-deoxyuridine, an antiviral and antineoplastic nucleoside. Conformational analysis of the deoxyribose ring, J. Am. Chem. Soc. 102 (1980) 4236-4241.
41. [41] J. Cadet, L. Voituriez, F.E. Hruska, L.-S. Kan, F.A.A. de Leeuw, C. Altona, Characterization of thymidine ultraviolet photoproducts. Cyclobutane dimers and 5,6-dihydrothymidines, Can. J. Chem. 63 (1985) 2861-2868.
42. [42] M. Hamberg, L.-Y. Zhang, Quantitative determination of 8-hydroxyguanine and guanine by isotope dilution mass spectrometry, Anal. Biochem. 229 (1995) 336-344.
43. [43] J.-L. Ravanat, R.J. Turesky, E. Gremaud, L.J. Trudel, R.H. Stalder, Determination of 8-oxoguanine in DNA by gas chromatogaphy-mass spectrometry and HPLC-electrochemical detection: overestimation of the background level of the oxidized base by the gas chromatography-mass spectrometry assay, Chem. Res. Toxicol. 8 (1995) 1039-1045.
44. [44] T. Douki, T. Delatour, F. Bianchini, J. Cadet, Observation and prevention of an artefactual formation of oxidized DNA bases and nucleosides in the GC-EIMS method, Carcinogenesis 17 (1996) 347-353.
45. [45] C. Hélène, M. Charlier, Photosensitized reactions in nucleic acids. Photosensitized formation and splitting of pyrimidine dimers, Biochimie 53 (1971) 1175-1180.
46. [46] M. Charlier, C. Hélène, W.L. Carrier, Photochemical reactions of aromatic ketones with nucleic acids and their components. I. Purine and pyrimidine bases and nucleosides, Photochem. Photobiol. 15 (1972) 71-87.
47. [47] M. Charlier, C. Hélène, W.L. Carrier, Photochemical reactions of aromatic ketones with nucleic acids and their components. III. Chain breakage and thymine dimerization in benzophenone photosensitized DNA, Photochem. Photobiol. 15 (1972) 527-536.
48. [48] G. Ciamician, P. Silber, Chemische Lichtwirkungen, Ber. Dtsch. chem. Ges. 33 (1900) 2911-2912.
49. [49] H.L.J. Bäckström, Der Kettenmechanismus bei der Autoxydation von Aldehyden, Z. Physik. Chem. Abt. B 25 (1934) 99-121.
50. [50] G.O. Schenck, Aufgaben und Möglichkeiten der präparativen Strahlenchemie, Angew. Chem. 69 (1957) 579-599.
51. [51] G.O. Schenck, H.-D. Becker, K.-H. Schulte-Elte, C.H. Krauch, Mit Benzophenon photosensibilisierte Autoxydation von sek. Alkoholen und Äthern Darstellung von α-Hydroperoxyden, Chem. Ber. 96 (1963) 509-516.
52. [52] J.A. Bell, H. Linschitz, Decay kinetics of the 1-naphthaldehyde and benzophenone triplet state in benzene, J. Am. Chem. Soc. 85 (1963) 528-532.
53. [53] I.G. Gut, P.D. Wood, R.W. Redmond, Interaction of triplet photosensitizers with nucleotides and DNA in aqueous solution at room temperature, J. Am. Chem. Soc. 118 (1996) 2366-2373.
54. [54] J.R. Wagner, J.E. van Lier, C. Decarroz, M. Berger, J. Cadet, Photodynamic methods for oxy radical-induced DNA damage, Methods Enzymol. 186 (1990) 502-511.
55. [55] G. Porter, F. Wilkinson, Primary photochemical processes in aromatic molecules. Part 5 - Flash photolysis of benzophenone in solution, Trans. Faraday Soc. 57 (1961) 1686-1691.
56. [56] H. Nohl, W. Jordan, R.J. Youngman, Quinones in biology: functions in electron transfer and oxygen activation, Free Radical Biol. Med. 2 (1986) 211-279.
57. [57] P.S. Rao, E. Hayon, One-electron redox reactions of free radicals in solution rate of electron transfer processes to quinones, Biochim. Biophys. Acta 292 (1973) 516-533.
58. [58] G.J. Fisher, E.J. Land, Photosensitization of pyrimidines by 2-methylnaphthoquinone in water: a laser flash photolysis study, Photochem. Photobiol. 37 (1983) 27-32.
59. [59] J.-C. Ronfard-Haret, R.V. Bensasson, E. Amouyal, Assignment of transient species observed on laser flash photolysis of p-benzoquinone and methylated p-benzoquinones in aqueous solution, J. Chem. Soc. Faraday Trans. 1 76 (1980) 2432-2436.
60. [60] J.R. Wagner, J.E. van Lier, L.J. Johnston, Quinone senitized electron transfer photooxidation of nucleic acids: chemistry of thymine and thymidine radical cations in aqueous solution, Photochem. Photobiol. 52 (1990) 333-343.
61. [61] A. Kuboyama, The phosphoresence spectra of 1,4-naphthoquinone and its alkyl derivatives in solutions at 77 K, Bull. Chem. Soc. Jpn. 51 (1978) 2771-2775.
62. [62] A.A. Lamola, M. Guéron, T. Yamane, J. Eisinger, R.G. Shulman, Triplet state of DNA, J. Chem. Phys. 47 (1967) 2210-2217.
63. [63] C.L. Greenstock, H.E. Johns, Photosensitized dimerization of pyrimidines, Biochem. Biophys. Res. Commun. 30 (1968) 21-27.