DNA damage spectra induced by photosensitization

Photochemical and Photobiological Sciences

Volumn 11, Issue 1, 2012, Pages 98-106

  Epe, Bernd ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84255197177     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c1pp05190c     Document Type: Review

References (76)

1. S. Brendler-Schwaab A. Czich B. Epe E. Gocke B. Kaina L. Muller D. Pollet D. Utesch Photochemical genotoxicity: principles and test methods. Report of a GUM task force Mutat. Res. 2004 566 65 91 (Pubitemid 38045589)
2. J. Cadet T. Douki J. L. Ravanat Measurement of oxidatively generated base damage in cellular DNA Mutat. Res. 2011 711 3 12
3. J. Cadet E. Sage T. Douki Ultraviolet radiation-mediated damage to cellular DNA Mutat. Res. 2005 571 3 17 (Pubitemid 40313428)
4. ESCODD Measurement of DNA oxidation in human cells by chromatographic and enzymic methods Free Radical Biol. Med. 2003 34 1089 1099
5. W. L. Neeley J. M. Essigmann Mechanisms of formation, genotoxicity, and mutation of guanine oxidation products Chem. Res. Toxicol. 2006 19 491 505
6. J. Musarrat A. A. Wani Quantitative immunoanalysis of promutagenic 8-hydroxy-2′-deoxyguanosine in oxidized DNA Carcinogenesis 1994 15 2037 2043
7. Y. Nakae P. J. Stoward I. A. Bespalov R. J. Melamede S. S. Wallace A new technique for the quantitative assessment of 8-oxoguanine in nuclear DNA as a marker of oxidative stress. Application to dystrophin-deficient DMD skeletal muscles Histochem. Cell Biol. 2005 124 335 345 (Pubitemid 41624217)
8. B. Epe J. Hegler Oxidative DNA damage: endonuclease fingerprinting Methods Enzymol. 1994 234 122 131
9. A. Hartwig H. Dally R. Schlepegrell Sensitive analysis of oxidative DNA damage in mammalian cells: use of the bacterial Fpg protein in combination with alkaline unwinding Toxicol. Lett. 1996 88 85 90 (Pubitemid 26361252)
10. A. Azqueta K. B. Gutzkow G. Brunborg A. R. Collins Towards a more reliable comet assay: Optimising agarose concentration, unwinding time and electrophoresis conditions Mutat. Res. 2011 724 41 45
11. A. R. Collins The use of bacterial repair endonucleases in the comet assay Methods Mol. Biol. 2011 691 137 147
12. D. Averbeck M. Dardalhon N. Magana-Schwencke Repair of furocoumarin-plus-UVA-induced damage and mutagenic consequences in eukaryotic cells J. Photochem. Photobiol., B 1990 6 221 236
13. G. E. Pfyffer B. U. Pfyffer G. H. Towers Monoaddition of dictamnine to synthetic double-stranded polydeoxyribonucleotides in UVA and the effect of photomodified DNA on template activity Photochem. Photobiol. 1982 35 793 797
14. E. Sage T. Le Doan V. Boyer D. E. Helland L. Kittler C. Helene E. Moustacchi Oxidative DNA damage photo-induced by 3-carbethoxypsoralen and other furocoumarins. Mechanisms of photo-oxidation and recognition by repair enzymes J. Mol. Biol. 1989 209 297 314 (Pubitemid 19237387)
15. F. Bosca V. Lhiaubet-Vallet M. C. Cuquerella J. V. Castell M. A. Miranda The triplet energy of thymine in DNA J. Am. Chem. Soc. 2006 128 6318 6319 (Pubitemid 43727260)
16. A. Moysan A. Viari P. Vigny L. Voituriez J. Cadet E. Moustacchi E. Sage Formation of cyclobutane thymine dimers photosensitized by pyridopsoralens: quantitative and qualitative distribution within DNA Biochemistry 1991 30 7080 7088
17. V. Lhiaubet-Vallet M. C. Cuquerella J. V. Castell F. Bosca M. A. Miranda Triplet excited fluoroquinolones as mediators for thymine cyclobutane dimer formation in DNA J. Phys. Chem. B 2007 111 7409 7414 (Pubitemid 47152529)
18. K. S. Robinson N. J. Traynor H. Moseley J. Ferguson J. A. Woods Cyclobutane pyrimidine dimers are photosensitised by carprofen plus UVA in human HaCaT cells Toxicol. In Vitro 2010 24 1126 1132
19. D. Roca-Sanjuan G. Olaso-Gonzalez I. Gonzalez-Ramirez L. Serrano-Andres M. Merchan Molecular basis of DNA photodimerization: intrinsic production of cyclobutane cytosine dimers J. Am. Chem. Soc. 2008 130 10768 10779
20. S. Mouret C. Philippe J. Gracia-Chantegrel A. Banyasz S. Karpati D. Markovitsi T. Douki UVA-induced cyclobutane pyrimidine dimers in DNA: a direct photochemical mechanism? Org. Biomol. Chem. 2010 8 1706 1711
21. D. Markovitsi T. Gustavsson A. Banyasz Absorption of UV radiation by DNA: spatial and temporal features Mutat. Res. 2010 704 21 28
22. B. Epe H. Henzl W. Adam C. R. Saha-Moller Endonuclease-sensitive DNA modifications induced by acetone and acetophenone as photosensitizers Nucleic Acids Res. 1993 21 863 869 (Pubitemid 23152993)
23. W. Mu Q. Han Z. Luo Y. Wang Production of cis-syn thymine-thymine cyclobutane dimer oligonucleotide in the presence of acetone photosensitizer Anal. Biochem. 2006 353 117 123 (Pubitemid 43668932)
24. S. Steenken S. V. Jovanovic How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution J. Am. Chem. Soc. 1997 119 617 618 (Pubitemid 27086555)
25. K. Ito S. Inoue K. Yamamoto S. Kawanishi 8-Hydroxydeoxyguanosine formation at the 5′ site of 5′-GG-3′ sequences in double-stranded DNA by UV radiation with riboflavin J. Biol. Chem. 1993 268 13221 13227 (Pubitemid 23307740)
26. I. Saito M. Takayama H. Sugiyama K. Nakatani Photoinduced DNA Cleavage Via Electron-Transfer-Demonstration That Guanine Residues Located 5′ to Guanine Are the Most Electron-Donating Sites J. Am. Chem. Soc. 1995 117 6406 6407
27. H. Sugiyama I. Saito Theoretical studies of GC-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. 1996 118 7063 7068 (Pubitemid 26261111)
28. J. Cadet T. Douki J. L. Ravanat Oxidatively generated damage to the guanine moiety of DNA: mechanistic aspects and formation in cells Acc. Chem. Res. 2008 41 1075 1083
29. M. L. Wood M. Dizdaroglu E. Gajewski J. M. Essigmann Mechanistic studies of ionizing radiation and oxidative mutagenesis: genetic effects of a single 8-hydroxyguanine (7-hydro-8-oxoguanine) residue inserted at a unique site in a viral genome Biochemistry 1990 29 7024 7032 (Pubitemid 20241148)
30. K. C. Cheng D. S. Cahill H. Kasai S. Nishimura L. A. Loeb 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G - T and A - C substitutions J. Biol. Chem. 1992 267 166 172
31. M. Moriya Single-stranded shuttle phagemid for mutagenesis studies in mammalian cells: 8-oxoguanine in DNA induces targeted G.C->T.A transversions in simian kidney cells Proc. Natl. Acad. Sci. U. S. A. 1993 90 1122 1126 (Pubitemid 23053963)
32. D. Ballmaier B. Epe Oxidative DNA damage induced by potassium bromate under cell-free conditions and in mammalian cells Carcinogenesis 1995 16 335 342
33. B. Matter D. Malejka-Giganti A. S. Csallany N. Tretyakova Quantitative analysis of the oxidative DNA lesion, 2,2-diamino-4-(2-deoxy-beta-D-erythro- pentofuranosyl)amino]-5(2H)-oxazolon e (oxazolone), in vitro and in vivo by isotope dilution-capillary HPLC-ESI-MS/MS Nucleic Acids Res. 2006 34 5449 5460 (Pubitemid 44742433)
34. M. Dizdaroglu G. Kirkali P. Jaruga Formamidopyrimidines in DNA: mechanisms of formation, repair, and biological effects Free Radical Biol. Med. 2008 45 1610 1621
35. I. Schulz H. C. Mahler S. Boiteux B. Epe Oxidative DNA base damage induced by singlet oxygen and photosensitization: recognition by repair endonucleases and mutagenicity Mutat. Res. 2000 461 145 156
36. K. Kino I. Saito H. Sugiyama Product analysis of GG-specific photooxidation of DNA via electron transfer: 2-aminoimidazolone as a major guanine oxidation product J. Am. Chem. Soc. 1998 120 7373 7374 (Pubitemid 28389374)
37. K. Kino H. Sugiyama Possible cause of G-C->C-G transversion mutation by guanine oxidation product, imidazolone Chem. Biol. 2001 8 369 378 (Pubitemid 32449300)
38. M. Hariharan S. C. Karunakaran D. Ramaiah I. Schulz B. Epe Photoinduced DNA damage efficiency and cytotoxicity of novel viologen linked pyrene conjugates Chem. Commun. 2010 46 2064 2066
39. M. M. Gonzalez M. Pellon-Maison M. A. Ales-Gandolfo M. R. Gonzalez-Baro R. Erra-Balsells F. M. Cabrerizo Photosensitized cleavage of plasmidic DNA by norharmane, a naturally occurring beta-carboline Org. Biomol. Chem. 2010 8 2543 2552
40. C. S. Foote Definition of type I and type II photosensitized oxidation Photochem. Photobiol. 1991 54 659
41. F. Bergeron F. Auvre J. P. Radicella J. L. Ravanat HO* radicals induce an unexpected high proportion of tandem base lesions refractory to repair by DNA glycosylases Proc. Natl. Acad. Sci. U. S. A. 2010 107 5528 5533
42. J. Cadet T. Douki D. Gasparutto J. L. Ravanat Oxidative damage to DNA: formation, measurement and biochemical features Mutat. Res. 2003 531 5 23 (Pubitemid 37456721)
43. J. P. Pouget S. Frelon J. L. Ravanat I. Testard F. Odin J. Cadet Formation of modified DNA bases in cells exposed either to gamma radiation or to high-LET particles Radiat. Res. 2002 157 589 595 (Pubitemid 34492566)
44. K. W. Kohn L. C. Erickson R. A. Ewig C. A. Friedman Fractionation of DNA from mammalian cells by alkaline elution Biochemistry 1976 15 4629 4637
45. M. Häring H. Rudiger B. Demple S. Boiteux B. Epe Recognition of oxidized abasic sites by repair endonucleases Nucleic Acids Res. 1994 22 2010 2015 (Pubitemid 24192898)
46. B. Epe D. Ballmaier W. Adam G. N. Grimm C. R. Saha-Moller Photolysis of N-hydroxpyridinethiones: a new source of hydroxyl radicals for the direct damage of cell-free and cellular DNA Nucleic Acids Res. 1996 24 1625 1631 (Pubitemid 26137918)
47. B. Epe M. Haring D. Ramaiah H. Stopper M. M. Abou-Elzahab W. Adam C. R. Saha-Moller DNA damage induced by furocoumarin hydroperoxides plus UV (360 nm) Carcinogenesis 1993 14 2271 2276 (Pubitemid 23335181)
48. H. C. Mahler I. Schulz W. Adam G. N. Grimm C. R. Saha-Moller B. Epe tert-Butoxyl radicals generate mainly 7,8-dihydro-8-oxoguanine in DNA Mutat. Res. 2001 461 289 299
49. Y. Ye J. G. Muller W. Luo C. L Mayne A. J. Shallop R. A. Jones C. J. Burrows Formation of 13C-, 15N-, and 18O-labeled guanidinohydantoin from guanosine oxidation with singlet oxygen. Implications for structure and mechanism J. Am. Chem. Soc. 2003 125 13926 13927 (Pubitemid 37420875)
50. J. E. McCallum C. Y. Kuniyoshi C. S. Foote Characterization of 5-hydroxy-8-oxo-7,8-dihydroguanosine in the photosensitized oxidation of 8-oxo-7,8-dihydroguanosine and its rearrangement to spiroiminodihydantoin J. Am. Chem. Soc. 2004 126 16777 16782 (Pubitemid 40073591)
51. J. L. Ravanat P. Di Mascio G. R. Martinez M. H. Medeiros J. Cadet Singlet oxygen induces oxidation of cellular DNA J. Biol. Chem. 2000 275 40601 40604 (Pubitemid 32064699)
52. J. L. Ravanat S. Sauvaigo S. Caillat G. R. Martinez M. H. Medeiros P. Di Mascio A. Favier J. Cadet Singlet oxygen-mediated damage to cellular DNA determined by the comet assay associated with DNA repair enzymes Biol. Chem. 2004 385 17 20 (Pubitemid 38240290)
53. E. Muller S. Boiteux R. P. Cunningham B. Epe Enzymatic recognition of DNA modifications induced by singlet oxygen and photosensitizers Nucleic Acids Res. 1990 18 5969 5973
54. O. Will E. Gocke I. Eckert I. Schulz M. Pflaum H. C. Mahler B. Epe Oxidative DNA damage and mutations induced by a polar photosensitizer, Ro19-8022 Mutat Res. 1999 435 89 101 (Pubitemid 29474950)
55. M. E. Serrentino A. Catalfo A. R. Angelin G. de Guidi E. Sage Photosensitization induced by the antibacterial fluoroquinolone Rufloxacin leads to mutagenesis in yeast Mutat Res. 2010 692 34 41
56. E. Gocke Review of the genotoxic properties of chlorpromazine and related phenothiazines Mutat Res. 1996 366 9 21 (Pubitemid 26371137)
57. T. A. Ciulla G. A. Epling I. E. Kochevar Photoaddition of chlorpromazine to guanosine-5′-monophosphate Photochem. Photobiol. 1986 43 607 613
58. A. W. Girotti Photosensitized oxidation of membrane lipids: reaction pathways, cytotoxic effects, and cytoprotective mechanisms J. Photochem. Photobiol., B 2001 63 103 113 (Pubitemid 33040728)
59. L. J. Marnett Oxyradicals and DNA damage Carcinogenesis 2000 21 361 370 (Pubitemid 30137921)
60. H. Bartsch J. Nair Ultrasensitive and specific detection methods for exocylic DNA adducts: markers for lipid peroxidation and oxidative stress Toxicology 2000 153 105 114
61. I. G. Minko I. D. Kozekov T. M. Harris C. J. Rizzo R. S. Lloyd M. P. Stone Chemistry and biology of DNA containing 1,N(2)-deoxyguanosine adducts of the alpha,beta-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal Chem. Res. Toxicol. 2009 22 759 778
62. G. P. Voulgaridou I. Anestopoulos R. Franco M. I. Panayiotidis A. Pappa DNA damage induced by endogenous aldehydes: Current state of knowledge Mutat. Res. 2011 711 13 27
63. C. Kielbassa L. Roza B. Epe Wavelength dependence of oxidative DNA damage induced by UV and visible light Carcinogenesis 1997 18 811 816 (Pubitemid 28132472)
64. J. P. Pouget T. Douki M. J. Richard J. Cadet DNA damage induced in cells by gamma and UVA radiation as measured by HPLC/GC-MS and HPLC-EC and Comet assay Chem. Res. Toxicol. 2000 13 541 549 (Pubitemid 30491114)
65. T. Douki A. Reynaud-Angelin J. Cadet E. Sage Bipyrimidine photoproducts rather than oxidative lesions are the main type of DNA damage involved in the genotoxic effect of solar UVA radiation Biochemistry 2003 42 9221 9226 (Pubitemid 36935432)
66. S. Courdavault C. Baudouin M. Charveron A. Favier J. Cadet T. Douki Larger yield of cyclobutane dimers than 8-oxo-7,8-dihydroguanine in the DNA of UVA-irradiated human skin cells Mutat. Res. 2004 556 135 142 (Pubitemid 39371186)
67. M. Pflaum C. Kielbassa M. Garmyn B. Epe Oxidative DNA damage induced by visible light in mammalian cells: extent, inhibition by antioxidants and genotoxic effects Mutat. Res. 1998 408 137 146 (Pubitemid 28345142)
68. G. T. Wondrak M. K. Jacobson E. L. Jacobson Endogenous UVA-photosensitizers: mediators of skin photodamage and novel targets for skin photoprotection Photochem. Photobiol. Sci. 2006 5 215 237 (Pubitemid 43228050)
69. B. Epe Role of endogenous oxidative DNA damage in carcinogenesis: what can we learn from repair-deficient mice? Biol. Chem. 2002 383 467 475 (Pubitemid 34506284)
70. S. Hoffmann-Dörr R. Greinert B. Volkmer B. Epe Visible light (>395 nm) causes micronuclei formation in mammalian cells without generation of cyclobutane pyrimidine dimers Mutat. Res. 2005 572 142 149 (Pubitemid 40403661)
71. M. A. Bachelor G. T. Bowden UVA-mediated activation of signaling pathways involved in skin tumor promotion and progression Semin. Cancer Biol. 2004 14 131 138 (Pubitemid 38234755)
72. S. Boiteux M. Guillet Abasic sites in DNA: repair and biological consequences in Saccharomyces cerevisiae DNA Repair 2004 3 1 12 (Pubitemid 38021990)
73. S. Bjelland E. Seeberg Mutagenicity, toxicity and repair of DNA base damage induced by oxidation Mutat. Res. 2003 531 37 80 (Pubitemid 37456723)
74. H. E. Krokan R. Standal G. Slupphaug DNA glycosylases in the base excision repair of DNA Biochem. J. 1997 325 Pt 1 1 16 (Pubitemid 27322679)
75. M. Dizdaroglu Base-excision repair of oxidative DNA damage by DNA glycosylases Mutat. Res. 2005 591 45 59 (Pubitemid 41654839)
76. W. Eiberger B. Volkmer R. Amouroux C. Dherin J. P. Radicella B. Epe Oxidative stress impairs the repair of oxidative DNA base modifications in human skin fibroblasts and melanoma cells DNA Repair 2008 7 912 921