Formamidopyrimidines as major products in the low- and high-intensity UV irradiation of guanine derivatives

Journal of Photochemistry and Photobiology B: Biology

Volumn 73, Issue 3, 2004, Pages 167-175

  Crespo Hernández, Carlos E ^a,b   Arce, Rafael ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

Base release; Fapy products; Guanine monomers; Quantum yield of formation

Indexed keywords

DEOXYGUANOSINE; GUANINE DERIVATIVE; PYRIMIDINE DERIVATIVE; RIBONUCLEOSIDE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; PHOTOLYSIS; PRIORITY JOURNAL; QUANTUM YIELD; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRAVIOLET RADIATION; ULTRAVIOLET SPECTROPHOTOMETRY;

DNA; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, RADIATION; GUANINE; OXYGEN; PYRIMIDINES; RADIATION DOSAGE; SOLUTIONS; ULTRAVIOLET RAYS; WATER;

EID: 1142311532     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2003.11.006     Document Type: Article

References (34)

1. Douki T. Angelov D. Cadet J. UV laser photolysis of DNA: effect of duplex stability on charge-transfer efficiency J. Am. Chem. Soc. 123 2001 11360-11366
2. Yoshioka Y. Kitagawa Y. Takano Y. Yamaguchi K. Nakamura T. Saito I. Experimental and theoretical studies on the selectivity of GGG triplets toward one-electron oxidation in B-form DNA J. Am. Chem. Soc. 121 1999 8712-8719
3. Wan C. Fiebig T. Kelley S.O. Treadway C.R. Barton J.K. Zewail A.H. Femtosecond dynamics of DNA-mediated electron transfer Proc. Natl. Acad. Sci. USA 96 1999 6014-6019
4. Saito I. Nakamura T. Nakatani K. Yoshioka Y. Yamaguchi K. Sagiyama H. Mapping of the hot spots for DNA damage by one-electron oxidation: efficacy of GG doublets and GGG triplets in long-range hole migration J. Am. Chem. Soc. 120 1998 12686-12687
5. Cadet J. Vigny P. The photochemistry of nucleic acids In: Morrison H. (Ed.), Bioorganic Photochemistry vol. 1 1990 1-272 Wiley New York
6. Nikogosyan D.N. Two quantum UV photochemistry of nucleic acids: comparison with conventional low intensity UV photochemistry and radiation chemistry Int. J. Radiat. Biol. 57 1990 233-299
7. Cullis P.H. Malone M.E. Davies L.A.M. Guanine radical cations are precursors of 7, 8-dihydro-8-oxo-2-deoxyguanosine but are not precursors of immediate strand breaks in DNA J. Am. Chem. Soc. 118 1996 2775-2781
8. Angelov D. Spassky A. Berger M. Cadet J. 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 J. Am. Chem. Soc. 119 1997 11373-11380
9. Crespo-Hernández C.E. Flores S. Torres C. Negrón-Encarnación I. Arce R. Photochemical and photophysical studies of guanine derivatives: intermediates contributing to its photodestruction mechanism in aqueous solution and the participation of the electron adduct Photochem. Photobiol. 71 2000 534-543
10. Crespo-Hernández C.E. Martínez L. González-Sierra A.E. Robles-Irizarry L. Díaz-Vázquez A. Arce R. The 254 nm low intensity and 266 nm laser photochemistry of adenosine. Effect of pH and concentration on the reactive precursors of the principal products, adenine and FapyAde J. Photochem. Photobiol. A: Chem. 152 2002 123-133
11. Crespo-Hernández C.E. Arce R. Photoionization of DNA and RNA bases, nucleosides and nucleotides through a combination of one- and two-photon pathways upon 266 nm nanosecond laser excitation Photochem. Photobiol. 76 2002 259-267
12. Papadantonakis G.A. Stevenson K.L. LeBreton P.R. Evidence of temperature dependent activation barriers for near-threshold aqueous photoionization of 2′-deoxyguanosine and tryptophan Chem. Phys. Lett. 346 2001 97-102
13. Crespo-Hernández C.E. Arce R. Near threshold photo-oxidation of dinucleotides containing purines upon 266 nm nanosecond laser excitation. The role of base stacking, conformation and sequence J. Phys. Chem. B 107 2003 1062-1070
14. Papadantonakis G.A. Tranter R. Brezinsky K. Yang Y. van Breemen R.B. LeBreton P.R. Low-energy, low-yield photoionization, and production of 8-oxo-2′-deoxyguanosine and guanine from 2′-deoxyguanosine J. Phys. Chem. B 106 2002 7704-7712
15. Sugiyama H. Saito I. Theoretical studies of GG-specific photocleavage of DNA via electron transfer: significant lowering of ionization potential and 5′-localization of HOMO of stacked GG bases in B-form DNA J. Am. Chem. Soc. 118 1996 7063-7068
16. Hutter M. Clark T. On the enhanced stability of the guanine-cytosine base-pair radical cation J. Am. Chem. Soc. 118 1996 7574-7577
17. Crespo-Hernández C.E. Arce R. Mechanism of formation of guanine as one of the major products in the 254 nm photolysis of guanine derivatives: concentration and pH effects Photochem. Photobiol. 71 2000 544-550
18. Doetsch P.W. Zastawny T.H. Martin A.M. Dizdaroglu M. Monomeric base damage products from adenine, guanine, and thymine induced by exposure of DNA to ultraviolet radiation Biochemistry 34 1995 737-742
19. Mori T. Dizdaroglu M. Ionizing radiation causes greater DNA base damage in radiation-sensitive mutant M10 cells than in parent mouse lymphoma L5178Y cells Radiat. Res. 140 1994 85-90
20. Boiteux S. Gajewski E. Laval J. Dizdaroglu M. 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 1992 106-110
21. Malins D.C. Haimanot R. 4,6-diamino-5-formamidopyrimidine, 8-hydroxyguanine and 8-hydroxyadenine in DNA from neoplastic liver of English sole exposed to carcinogens Biochem. Biophys. Res. Comm. 173 1990 614-619
22. Burgdorf L.T. Carell T. Synthesis, stability, and conformation of the formamidopyridine G DNA Lesion Chem. Eur. J. 8 2002 293-301
23. Delaney M.O. Wiederholf C.J. Greenberg M.M. FapydA induces nucleotide misincorporation translesionally by a DNA polymerase Angew. Chem. Int. Ed. 41 2002 771-773
24. Ravanat J.L. Duretz B. Guiller A. Douki T. Cadet J. Isotope dilution high-performance liquid chromatography-electrospray tandem mass spectrometry assay for the measurement of 8-oxo-7,8-dihydro-2′-deoxyguanosine in biological samples J. Chromatogr. B 715 1998 349-356
25. Frelon S. Douki T. Ravanat J.-L. Tornabene C. Cadet J. High performance liquid chromatography-tandem mass spectrometry measurement of radiation-induced base damage to isolated and cellular DNA Chem. Res. Toxicol. 13 2000 1002-1010
26. Douki T. Court M. Cadet J. Electrospray-mass spectrometry characterization and measurement of far-UV-induced thymine photoproducts J. Photochem. Photobiol. B: Biol. 54 2000 145-154
27. Hems G. Effect of ionizing radiation on aqueous solution of guanylic acid and guanosine Nature 151 1958 1721-1722
28. Berger M. Cadet J. Isolation and characterization of the radiation-induced degradation products of 2′-deoxyguanosine in oxygen free aqueous solutions Z. Naturforsch. 40b 1985 1519-1531
29. Raoul S. Bardet M. Cadet J. γ-Irradiation of 2′ deoxyadenosine in oxygen-free aqueous solutions: identification and conformational features of formidopyrimidine nucleoside derivatives Chem. Res. Toxicol. 8 1995 924-933
30. Ravanat J.-L. Douki T. Cadet J. Direct and indirect effects of UV radiation on DNA and its components J. Photochem. Photobiol. B: Biol. 63 2001 88-102
31. Bishop S.M. Malone M. Phillips D. Parker A.W. Symons M.C.R. Singlet oxygen sensitization of excited state DNA J. Chem. Soc. Chem. Commun. 1994 871-872
32. Mohammad T. Morrison H. Evidence for the photosensitized formation of singlet oxygen by UVB irradiation of 2′-deoxyguanosine 5′-monophosphate J. Am. Chem. Soc. 118 1996 1221-1222
33. - and OH adducts Chem. Rev. 89 1989 503-520
34. Arce R. Martínez L. Danielsen E. The photochemistry of adenosine: intermediates contributing to its photodegradation mechanism in aqueous solution at 298 K and characterization of the major product Photochem. Photobiol. 58 1993 318-328