89
3 Formation of DNA Lesions, its Prevention and Repair
111. Gu F, Stillwell WG, Wishnok JS, Shallop AJ, Jones RA, Tannenbaum SR (2002) Peroxynitrite-induced reactions of synthetic oligo 2’-deoxynucleotides and DNA containing
guanine: formation and stability of a 5-guanidino-4-nitroimidazole lesion. Biochemistry
41:7508–7518
112. Niles JC, Wishnok JS, Tannenbaum SR (2006) Peoxynitrite-induced oxidation and nitration
products of guanine and 8-oxoguanine: structures and mechanisms of product formation.
Nitric Oxide 14:109–121
113. Niles JC, Wishnok JS, Tannenbaum SR (2001) A novel nitroimidazole compound formed
during the reaction of peroxynitrite with 2’,3’,5’-tri-O-acetyl-guanosine. J Am Chem Soc
49:12147–12151
114. Neeley WL, Henderson PT, Delaney JC, Essigmann JM (2004) In vivo bypass efficiencies and mutational signatures of the guanine oxidation products 2-aminoimidazolone and
5-guanidino-4-nitroimidazole. J Biol Chem 279:43568–43573
115. Cullis PM, Malone ME, MersonDavies LA (1996) 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 118:2775–2781
116. Sarasin A, Bounacer A, Lepage F, Schlumberger M, Suarez HG (1999) Mechanisms of
mutagenesis in mammalian cells. Application to human thyroid tumours. C R Acad Sci III
322:143–149
117. Kumar A, Venkata P, Sevilla MD (2011) Hydroxyl Radical Reaction with Guanine in an
Aqueous Environment: a DFT Study. J Phys Chem B 115:15129–15137
118. Kobayashi K, Tagawa S (2003) Direct observation of guanyl radical cation deprotonation
in duplex DNA using pulse radiolysis. J Am Chem Soc 125:10213–10218
119. Rokhlenko Y, Geacintov NE, Shafirovich V (2012) Lifetimes and reaction pathways of
guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions. J Am Chem Soc 134:4955–4962
120. Luo W, Muller, JG, Burrows CJ (2001) The pH-dependent role of superoxide in riboflavincatalyzed photooxidation of 8-oxo-7,8-dihydroguanosine. Org Lett 3:2801–2804
121. Hohenberg P, Kohn W (1964) Inhomogeneous electron gas. Phys Rev 136B:864–871
122. Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev A 140:1133–1138
123. Barone V, Cossi M, Tomasi J (1997) A new definition of cavities for the computation of
solvation free energies by the polarizable continuum model. J Chem Phys 107:3210–3221
124. Cossi M, Barone V, Mennucci B, Tomasi J (1998) Ab-initio Study of Ionic Solutions by a
Polarizable Continuum Dielectric Model. Chem Phys Lett 286:253–260
125. Spencer JPE, Whiteman M, Jenner A, Halliwell B (2000) Nitrite-induced deamination and
hypochlorite-induced oxidation of DNA in intact human respiratory tract epithelial cells.
Free Radic Biol Med 28:1039–1050
126. Shafirovich V, Dourandin A, Huang W, Geacintov NE (2001) The carbonate radical is a
site-selective oxidizing agent of guanine in double-stranded oligonucleotides. J Biol Chem
276:24621–24626
127. Rokhlenko Y, Geacintov NE, Shafirovich V (2012) Lifetimes and reaction pathways of
guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions. J Am Chem Soc 134:4955–4962
128. Joffe A, Geacintov NE, Shafirovich V (2003) DNA lesions derived from the site selective
oxidation of guanine by carbonate radical anions. Chem Res Toxicol 16:1528–1538
129. Masuda M, Suzuki T, Friensen MD, Ravanat JL, Cadet J, Pignattelli B, Nishino H, Ohshima H (2001) Chlorination of guanosine and other nucleosides by hypochlorous acid and
myeloperoxidase of activated human neutrophils catalysis by nicotine and trimethylamine.
J Biol Chem 276:40486–40496
130. Badouard C, Masuda M, Nishino H, Cadet J, Favier A, Ravanat JL (2005) Detection of
chlorinated DNA and RNA nucleosides by HPLC coupled to tandem mass spectrometry
as potential biomarkers of inflammation. J Chromatogr B Analyt Technol Biomed Life Sci
827:26–31
3 Formation of DNA Lesions, its Prevention and Repair
111. Gu F, Stillwell WG, Wishnok JS, Shallop AJ, Jones RA, Tannenbaum SR (2002) Peroxynitrite-induced reactions of synthetic oligo 2’-deoxynucleotides and DNA containing
guanine: formation and stability of a 5-guanidino-4-nitroimidazole lesion. Biochemistry
41:7508–7518
112. Niles JC, Wishnok JS, Tannenbaum SR (2006) Peoxynitrite-induced oxidation and nitration
products of guanine and 8-oxoguanine: structures and mechanisms of product formation.
Nitric Oxide 14:109–121
113. Niles JC, Wishnok JS, Tannenbaum SR (2001) A novel nitroimidazole compound formed
during the reaction of peroxynitrite with 2’,3’,5’-tri-O-acetyl-guanosine. J Am Chem Soc
49:12147–12151
114. Neeley WL, Henderson PT, Delaney JC, Essigmann JM (2004) In vivo bypass efficiencies and mutational signatures of the guanine oxidation products 2-aminoimidazolone and
5-guanidino-4-nitroimidazole. J Biol Chem 279:43568–43573
115. Cullis PM, Malone ME, MersonDavies LA (1996) 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 118:2775–2781
116. Sarasin A, Bounacer A, Lepage F, Schlumberger M, Suarez HG (1999) Mechanisms of
mutagenesis in mammalian cells. Application to human thyroid tumours. C R Acad Sci III
322:143–149
117. Kumar A, Venkata P, Sevilla MD (2011) Hydroxyl Radical Reaction with Guanine in an
Aqueous Environment: a DFT Study. J Phys Chem B 115:15129–15137
118. Kobayashi K, Tagawa S (2003) Direct observation of guanyl radical cation deprotonation
in duplex DNA using pulse radiolysis. J Am Chem Soc 125:10213–10218
119. Rokhlenko Y, Geacintov NE, Shafirovich V (2012) Lifetimes and reaction pathways of
guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions. J Am Chem Soc 134:4955–4962
120. Luo W, Muller, JG, Burrows CJ (2001) The pH-dependent role of superoxide in riboflavincatalyzed photooxidation of 8-oxo-7,8-dihydroguanosine. Org Lett 3:2801–2804
121. Hohenberg P, Kohn W (1964) Inhomogeneous electron gas. Phys Rev 136B:864–871
122. Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev A 140:1133–1138
123. Barone V, Cossi M, Tomasi J (1997) A new definition of cavities for the computation of
solvation free energies by the polarizable continuum model. J Chem Phys 107:3210–3221
124. Cossi M, Barone V, Mennucci B, Tomasi J (1998) Ab-initio Study of Ionic Solutions by a
Polarizable Continuum Dielectric Model. Chem Phys Lett 286:253–260
125. Spencer JPE, Whiteman M, Jenner A, Halliwell B (2000) Nitrite-induced deamination and
hypochlorite-induced oxidation of DNA in intact human respiratory tract epithelial cells.
Free Radic Biol Med 28:1039–1050
126. Shafirovich V, Dourandin A, Huang W, Geacintov NE (2001) The carbonate radical is a
site-selective oxidizing agent of guanine in double-stranded oligonucleotides. J Biol Chem
276:24621–24626
127. Rokhlenko Y, Geacintov NE, Shafirovich V (2012) Lifetimes and reaction pathways of
guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions. J Am Chem Soc 134:4955–4962
128. Joffe A, Geacintov NE, Shafirovich V (2003) DNA lesions derived from the site selective
oxidation of guanine by carbonate radical anions. Chem Res Toxicol 16:1528–1538
129. Masuda M, Suzuki T, Friensen MD, Ravanat JL, Cadet J, Pignattelli B, Nishino H, Ohshima H (2001) Chlorination of guanosine and other nucleosides by hypochlorous acid and
myeloperoxidase of activated human neutrophils catalysis by nicotine and trimethylamine.
J Biol Chem 276:40486–40496
130. Badouard C, Masuda M, Nishino H, Cadet J, Favier A, Ravanat JL (2005) Detection of
chlorinated DNA and RNA nucleosides by HPLC coupled to tandem mass spectrometry
as potential biomarkers of inflammation. J Chromatogr B Analyt Technol Biomed Life Sci
827:26–31