Photoinduced electron transfer cleavage of oxetane adducts of uracil and cytosine

Photochemical and Photobiological Sciences

Volumn 1, Issue 9, 2002, Pages 632-635

  Joseph, Arul ^a   Falvey, Daniel E ^a  

^a UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOSINE; ETHER DERIVATIVE; OXETANE; URACIL; ANION; BENZOPHENONE; CYTOSINE DERIVATIVE; OXETANE DERIVATIVE; PYRIMIDINE DERIVATIVE; TETRAMETHYLBENZIDINE; URACIL DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; ELECTRON TRANSPORT; LIGHT; RADIATION EXPOSURE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DEGRADATION KINETICS; DNA ADDUCT; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR STABILITY; NEODYMIUM LASER; PHOTOCHEMICAL QUENCHING; PHOTOLYSIS; PHOTOSENSITIZATION; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

CYTOSINE; ELECTRON TRANSPORT; ETHERS, CYCLIC; LIGHT; MOLECULAR CONFORMATION; URACIL;

EID: 0036768845     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b201740g     Document Type: Article

References (27)

1. H. Görner Photochemistry of DNA and related biomolecules: quantum yields and consequences of photoionization J. Photochem. Photobiol., B 1994 26 117-139.
2. 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. 1997 378 1275-1286.
3. J.-S. Taylor DNA, Sunlight and skin cancer Pure Appl. Chem. 1995 67 183-190.
4. H. E. Johns M. L. Pearson J. C. LeBlanc C. W. Helleiner The ultraviolet photochemistry of thymidyl-(3′→5′)-thymidine J. Mol. Biol. 1964 9 503-524.
5. R. E. Rycyna J. L. Alderfer UV irradiation of nucleic acids: formation, structure, purification and solution conformational analysis of the ‘6–4 lesion’ of dTpdT Nucleic Acids Res. 1985 13 5949-5963.
6. J.-S. Taylor M. P. Cohrs DNA, Light, and dewar pyrimidones: the structure and biological significance of TpT3 J. Am. Chem. Soc. 1987 109 2834-2835.
7. J. E. Cleaver F. Cortés D. Karentz L. H. Lutze W. F. Morgan A. N. Player L. Vuksanovic D. L. Mitchell The relative biological importance of cyclobutane and (6–4) pyrimidine-pyrimidone dimer photoproducts in human cells: evidence from a xeroderma pigmentosum revertant Photochem. Photobiol. 1988 48 41-49.
8. N. Jiang J.-S. Taylor In vivo evidence that UV-induced C→T mutations at dipyrimidine sites could result from the replicative bypass of cis-syn cyclobutane dimers or their deamination products Biochemistry 1993 32 472-481.
9. A. Gentil F. LePage A. Margot C. W. Lawrence A. Borden A. Sarasin Mutagenicity of a unique thymine-thymine dimer or thymine-thymine pyrimidine-pyrimidone (6–4) photoproduct in mammalian cells Nucleic Acids Res. 1996 24 1837-1840.
10. M. Tachiya Effect of the dielectric saturation on the rates of electron transfer in polar solvents Chem. Phys. Lett. 1989 159 505-510.
11. T. Todo H. Takemori H. Ryo M. Ihara T. Matsunaga O. Nikaido K. Sato T. Nomura A new photoreactivating enzyme that specifically repairs ultraviolet light-induced (6–4)photoproducts Nature 1993 361 371-374.
12. T. Todo H. Ryo K. Yamamoto H. Toh T. Inui H. Ayaki T. Nomura M. Ikenaga Similarity among the drosophila (6–4) photolyase, a human photolyase homolog, and the DNA photolyase–blue light photoreceptor family Science (Washington, D. C.) 1996 272 109-112.
13. T. Todo S.-T. Kim K. Hitomi E. Otoshi T. Inui H. Morioka H. Kobayashi E. Ohtsuka H. Toh M. Ikenaga Flavin adenine dinucleotide as a chromophore of the xenopus(6–4) photolyase Nucleic Acids Res. 1997 25 764-768.
14. T. Todo H. Ryo A. Borden C. Lawrence K. Sakaguchi H. Hirata T. Nomura Non-mutagenic repair of (6–4) photoproducts by (6–4) photolyase purified from drosophila melanogaster. Mutat. Res. 1997 385 83-93.
15. D. J. Kieber N. V. Blough Determination of carbon-centered radicals in aqueous solution by liquid chromatography with fluorescence detection Anal. Chem. 1990 62 2275-2283.
16. S.-T. Kim K. Malhotra C. A. Smith J.-S. Taylor A. Sancar characterization of (6–4) photoproduct DNA photolyase J. Biol. Chem. 1994 269 8535-8540.
17. S.-T. Kim K. Malhotra J.-S. Taylor A. Sancar Purification and partial characterization of (6–4) photoproduct DNA photolyase from Xenopus laevis. Photochem. Photobiol. 1996 63 292-295.
18. X. Zhao J. Liu D. S. Hsu S. Zhao J.-S. Taylor A. Sancar Reaction mechanism of (6–4) photolyase J. Biol. Chem. 1997 272 32580-32590.
19. G. Prakash D. E. Falvey Model Studies of the (6–4)-photoproduct photolyase: Synthesis and photosensitized splitting of a thymine 5,6-oxetane J. Am. Chem. Soc. 1995 117 11375-11376.
20. A. Joseph G. Prakash D. E. Falvey Model studies of the (6–4) photoproduct photolyase enzyme: laser flash photolysis studies confirm radical ion intermediates in the repair of thymine oxetane adducts J. Am. Chem. Soc. 2000 122 11219-11225.
21. K. Hitomi H. Nakamura S.-T. Kim T. Mizukoshi T. Ishikawa S. Iwai T. Todo Role of two histidines in the (6–4) photolyase reaction J. Biol. Chem. 2001 276 10103-10109.
22. G. G. Gurzadyan H. Görner Depopulation of highly excited singlet states of DNA model compounds: quantum yields of 193 and 245 nm photoproducts of pyrimidine monomers and dinucleoside monophosphates Photochem. Photobiol. 1996 63 143-153.
23. T. Douki J. Cadet Individual Determination of the Yield of the Main UV-Induced Dimeric Pyrimidine Photoproducts in DNA Suggests a High Mutagenicity of CC Photolesions Biochemistry 2001 40 2495-2501.
24. Yields were corrected for conversion of oxetane and were determined in triplicate T. Shida, Electronic Absorption Spectra of Radical Ions, 1988, Amsterdam, Elsevier, p. 446.
25. M. Yamaji T. Kiyota S. Kimura H. Shizuka Laser flash-photolysis studies on the interaction between triplet benzophenone and naphtholate anions – electron-transfer or triplet energy-transfer Chem. Phys. Lett. 1995 237 419-424.
26. A. Demeter B. László T. Bérces Kinetics of ketyl radical reactions occurring in the photoreduction of benzophenone by isopropyl alcohol Ber. Bunsen-Ges. Phys. Chem. 1988 92 1478-1485.
27. K. S. Peters A. Cashin P. Timbers Picosecond dynamics of nonadiabatic proton transfer: a kinetic study of proton transfer within the contact radical ion pair of substituted benzophenones/N, N-dimethylaniline J. Am. Chem. Soc. 2000 122 107-113.