87
3 Formation of DNA Lesions, its Prevention and Repair
71. Steenken S (1989) Purine bases, nucleosides, nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and e
-
and OH adducts. Chem Rev
89:503–520
72. Reynisson J, Steenken S (2002) DFT calculations on the electrophilic reaction with water of
the guanine and adenine radical cations: a model for the situation in DNA. Phys Chem Chem
Phys 4:527–532
73. Yadav A, Mishra PC (2011) Quantum theoretical study of mechanism of the reaction between
guanine radical cation and carbonate radical anion: formation of 8-oxoguanine. Int J Quantum Chem 112:2000–2008
74. Agnihotri N, Mishra PC (2011) Reactivities of radicals of adenine and guanine towards reactive oxygen species and reactive nitrogen oxide species: OH
•
and NO 2
•
. Chem Phys Lett
503:305–309
75. Kasai H, Yamaizumi Z, Berger M, Cadet J (1992) Photosensitized formation of 7,8-dihydro8-oxo-2’-deoxyguanosine (8-hydroxy-2’-deoxyguanosine) in DNA by riboflavin: a non-singlet oxygen mediated reaction. J Am Chem Soc 114:9692–9694
76. Jena NR (2012) DNA damage by reactive species: mechanisms, mutation and repair. J Biosci
3:503–517
77. Munk BH, Burrows CJ, Schlegel HB (2007) Exploration of mechanisms for the transformation of 8-hydroxy guanine radical to FAPyG by density functional theory. Chem Res Toxicol
20:432–444
78. Jena NR, Mishra PC (2012) Formation of ring-opened and rearranged products of guanine:
mechanisms and biological significance. Free Radic Biol Med 53:81–94
79. Chatgilialoglu C, Neill PO (2001) Free radicals associated with DNA damage. Exp Gerontol
36:1459–1471
80. Tudek B (2003) Imidazole ring-opened DNA purines and their biological significance. J Biochem Mol Biol 36:12–19
81. Dizdaroglu M, Kirkali G, Jaruga P (2008) Formamidopyrimidines in DNA: mechanisms of
formation, repair and biological effects. Free Radic Biol Med 45:1610–1620
82. Gates KS (2009) An overview of chemical processes that damage cellular DNA: spontaneous
hydrolysis, alkylation and reactions with radicals. Chem Res Toxicol 22:1747–1760
83. Douki T, Spinelli S, Ravanat JL, Cadet J (1999) Hydroxyl radical-induced degradation of
2’-deoxyguanosine under reducing conditions. J Chem Soc Perkin Trans 2:1875–1880
84. Cui L, Ye WJ, Prestwich EG, Wishnok JS, Taghizadeh K, Dedon PC, Tannenbaum SR (2013)
Comparative analysis of four oxidized guanine lesions from reactions of DNA with peroxynitrite, singlet oxygen, and gamma-radiation. Chem Res Toxicol 26:195–202
85. Raoul S, Berger M, Buchko GW, Joshi PC, Morin B, Weinfeld M, Cadet J (1996) H-1, C-13
and N-15 nuclear magnetic resonance analysis and chemical features of two main radical
oxidation products of 2’-deoxyguanosine: oxazolone and imidazolone nucleosides. J Chem
Soc Perkin Trans 2:371–381
86. Epe B (1996) DNA damage profiles induced by oxidizing agents. Rev Physiol Biochem
Pharmacol 127:223–249
87. Breen AP, Murphy JA (1995) Reactions of oxyl radicals with DNA. Free Radic Biol Med
18:1033–1077
88. Matter B, Malejka-Giganti D, Csallany AS, Tretyakova N (2006) Quantitative analysis of the
oxidative DNA lesion, 2,2-Diamino-43,5-di-O-acetyl-2-deoxy-b-D-erthro-sepentofuranosyl)
amino]-5-(2H)-oxazolone (oxazolone) in vitro and in vivo by isotope dilution-capillary
HPLC-ESI-MS/MS. Nucleic Acids Res 34:5499–5460
89. Luo WC, Muller JG, Rachlin EM, Burrows CJ (2001) Characterization of hydantoin products
from one-electron oxidation of 8-oxo-7,8-dihydroguanosine in a nucleoside model. Chem
Res Toxicol 14:927–938
90. Neeley WL, Essigmann JM (2006) Mechanisms of formation, genotoxicity and mutation of
guanine oxidation products. Chem Res Toxicol 19:491–505
91. Matter B, Malejka-Giganti D, Csallany AS, Treyakova N (2006) Quantitative analysis of the
oxidative DNA lesion, 2,2-diamino-4-(2-deoxy-β-d-erythro-pentofuranosyl)amino]-5(2H)oxazolone (oxazolone), in vitro and in vivo by isotope dilution-capillary HPLC-ESI-MS/MS.
Nucleic Acids Res 34:5449–5460
3 Formation of DNA Lesions, its Prevention and Repair
71. Steenken S (1989) Purine bases, nucleosides, nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and e
-
and OH adducts. Chem Rev
89:503–520
72. Reynisson J, Steenken S (2002) DFT calculations on the electrophilic reaction with water of
the guanine and adenine radical cations: a model for the situation in DNA. Phys Chem Chem
Phys 4:527–532
73. Yadav A, Mishra PC (2011) Quantum theoretical study of mechanism of the reaction between
guanine radical cation and carbonate radical anion: formation of 8-oxoguanine. Int J Quantum Chem 112:2000–2008
74. Agnihotri N, Mishra PC (2011) Reactivities of radicals of adenine and guanine towards reactive oxygen species and reactive nitrogen oxide species: OH
•
and NO 2
•
. Chem Phys Lett
503:305–309
75. Kasai H, Yamaizumi Z, Berger M, Cadet J (1992) Photosensitized formation of 7,8-dihydro8-oxo-2’-deoxyguanosine (8-hydroxy-2’-deoxyguanosine) in DNA by riboflavin: a non-singlet oxygen mediated reaction. J Am Chem Soc 114:9692–9694
76. Jena NR (2012) DNA damage by reactive species: mechanisms, mutation and repair. J Biosci
3:503–517
77. Munk BH, Burrows CJ, Schlegel HB (2007) Exploration of mechanisms for the transformation of 8-hydroxy guanine radical to FAPyG by density functional theory. Chem Res Toxicol
20:432–444
78. Jena NR, Mishra PC (2012) Formation of ring-opened and rearranged products of guanine:
mechanisms and biological significance. Free Radic Biol Med 53:81–94
79. Chatgilialoglu C, Neill PO (2001) Free radicals associated with DNA damage. Exp Gerontol
36:1459–1471
80. Tudek B (2003) Imidazole ring-opened DNA purines and their biological significance. J Biochem Mol Biol 36:12–19
81. Dizdaroglu M, Kirkali G, Jaruga P (2008) Formamidopyrimidines in DNA: mechanisms of
formation, repair and biological effects. Free Radic Biol Med 45:1610–1620
82. Gates KS (2009) An overview of chemical processes that damage cellular DNA: spontaneous
hydrolysis, alkylation and reactions with radicals. Chem Res Toxicol 22:1747–1760
83. Douki T, Spinelli S, Ravanat JL, Cadet J (1999) Hydroxyl radical-induced degradation of
2’-deoxyguanosine under reducing conditions. J Chem Soc Perkin Trans 2:1875–1880
84. Cui L, Ye WJ, Prestwich EG, Wishnok JS, Taghizadeh K, Dedon PC, Tannenbaum SR (2013)
Comparative analysis of four oxidized guanine lesions from reactions of DNA with peroxynitrite, singlet oxygen, and gamma-radiation. Chem Res Toxicol 26:195–202
85. Raoul S, Berger M, Buchko GW, Joshi PC, Morin B, Weinfeld M, Cadet J (1996) H-1, C-13
and N-15 nuclear magnetic resonance analysis and chemical features of two main radical
oxidation products of 2’-deoxyguanosine: oxazolone and imidazolone nucleosides. J Chem
Soc Perkin Trans 2:371–381
86. Epe B (1996) DNA damage profiles induced by oxidizing agents. Rev Physiol Biochem
Pharmacol 127:223–249
87. Breen AP, Murphy JA (1995) Reactions of oxyl radicals with DNA. Free Radic Biol Med
18:1033–1077
88. Matter B, Malejka-Giganti D, Csallany AS, Tretyakova N (2006) Quantitative analysis of the
oxidative DNA lesion, 2,2-Diamino-43,5-di-O-acetyl-2-deoxy-b-D-erthro-sepentofuranosyl)
amino]-5-(2H)-oxazolone (oxazolone) in vitro and in vivo by isotope dilution-capillary
HPLC-ESI-MS/MS. Nucleic Acids Res 34:5499–5460
89. Luo WC, Muller JG, Rachlin EM, Burrows CJ (2001) Characterization of hydantoin products
from one-electron oxidation of 8-oxo-7,8-dihydroguanosine in a nucleoside model. Chem
Res Toxicol 14:927–938
90. Neeley WL, Essigmann JM (2006) Mechanisms of formation, genotoxicity and mutation of
guanine oxidation products. Chem Res Toxicol 19:491–505
91. Matter B, Malejka-Giganti D, Csallany AS, Treyakova N (2006) Quantitative analysis of the
oxidative DNA lesion, 2,2-diamino-4-(2-deoxy-β-d-erythro-pentofuranosyl)amino]-5(2H)oxazolone (oxazolone), in vitro and in vivo by isotope dilution-capillary HPLC-ESI-MS/MS.
Nucleic Acids Res 34:5449–5460