88
N. R. Jena et al.
92. Hah SS, Kim HM, Sumbad RA, Henderson PT (2005) Hydantoin derivative formation
from oxidation of 7,8-dihydro-8-oxo-2’-deoxyguanosine (8-oxodG) and incorporation of
14C-labeled 8-oxodG into the DNA of human breast cancer cells. Bioorg Med Chem Lett
15:3627–3631
93. Vialas C, Pratviel G, Claporols C, Meunier B (1998) Efficient oxidation of 2’-deoxyguanosine by Mn-TMPyP/KHSO5 to imidazolone without formation of 8-oxodG. J Am Chem
Soc 120:11548–11553
94. Crean C, Geacintov NE, Shafirovich V (2008) Pathways of arachidonic acid peroxyl radical
reactions and product formation with guanine radicals. Chem Res Toxicol 21:358–373
95. Vialas C, Claparols C, Pratviel G () Meunier B (200) Guanine oxidation in double-stranded
DNAby Mn-TMPyP/KHSO5: 5,8-dihydroxy-7,8-dihydroguanine residue as a key precursor of imidazolone and parabanic acid derivatives. J Am Chem Soc 122:2157–2167
96. Niles JC, Wishnok JS, Tannenbaum SR (2001) Spiroiminohydantoin is the major product
of 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols, and
guanosine photooxidation by methylene blue. Org Lett 3:763–766
97. Luo WC, Muller JC, Rachlin E, Burrows CJ (2000) Characterization of spiroiminohydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine. Org Lett
2:613–617
98. Raoul S, Cadet J (1996) Photosensitized reaction of 8-oxo-7,8-dihydro-2’-deoxyguanosine.
identification of 1-(2-deoxy-beta-D-erythro-penofuransoyl)cyanuric acid as the major singlet oxygen oxidation product. J Am Chem Soc 118:1892–1898
99. Sheu C, Foote CS (1995) Photosensitized oxygenation of a 7,8-dihydro-8-oxoguanosine
derivative. Formation of dioxetane and hydroperoxide intermediates. J Am Chem Soc
117:474–477
100. Duarte V, Gasparutto D, Yamaguchi LF, Ravanat JL, Martinez GR, Medeiros MHG, Di
Mascio P, Cadet J (2000) Oxaluric acid as the major product of singlet oxygen mediated
oxidation of 8-oxo-7,8-dihydroguanine in DNA. J Am Chem Soc 122:12622–12628
101. Niles JC, Wishnok JS, Tannenbaum SR (2000) A novel nitration product formed during the
reaction of peroxynitrite with 2’,3’,5’-tri-O-acetyl-7,8-dihydro-8-oxoguanosine. Chem Res
Toxicol 13:390–396
102. Niles JC, Burney S, Singh SP, Wishnok JS, Tannenbaum SR (1999) Peroxynitrite reaction
products of 3’,5’-di-O-acetyl-8-oxo-7,8-dihydro-2’-deoxyuanosine. Proc Natl Acad Sci U
S A 96:11729–11734
103. Tretyakova NY, Niles JC, Burney S, Wishnok JS, Tannenbaum SR (1999) Peroxynitriteinduced reactions of synthetic oligonucleotides containing 8-oxoguanine. Chem Res Toxicol 12:459–466
104. Ravanat JL, Saint-Pierre C, Cadet J (2003) One-electron oxidation of the guanine moiety of
2’-deoxyguanosine: influence of 8-oxo-7,8-dihydro-2’-deoxyguanosine. J Am Chem Soc
125:2030–2031
105. Jena NR, Mishra PC (2006) Addition and hydrogen abstraction reactions of an OH radical
with 8-oxoguanine. Chem Phys Lett 422:417–423
106. Bashir S, Harris G, Denman MA, Blake DR, Winyard PG (1993) Oxidative DNA damage
and cellular sensitivity to oxidative stress in human autoimmune diseases. Ann Rheum Dis
52:659–666
107. Jena, NR, Mishra PC (2013) Is FapyG mutagenic: evidence from the DFT study. Chemphyschem 14:3263–3270.
108. Akaike T, Okamoto S, Sawa T, Yoshitake J, Tamura F, Ichimori K, Miyazaki K, Sasamoto
K, Maeda H (2003) 8-Nitroguanosine formation in viral pneumonia and its implication for
pathogenesis. Proc Natl Acad Sci U S A 100:685–690
109. Tuo J, Liu L, Poulsen HE, Weimann A, Svendsen O, Loft S (2000) Importance of guanine
nitration and hydroxylation in DNA in vitro and in vivo. Free Radic Biol Med 29:147–155
110. Halliwell B (2007) Oxidative stress and cancer: have we moved forward? Biochem J
401:1–11
N. R. Jena et al.
92. Hah SS, Kim HM, Sumbad RA, Henderson PT (2005) Hydantoin derivative formation
from oxidation of 7,8-dihydro-8-oxo-2’-deoxyguanosine (8-oxodG) and incorporation of
14C-labeled 8-oxodG into the DNA of human breast cancer cells. Bioorg Med Chem Lett
15:3627–3631
93. Vialas C, Pratviel G, Claporols C, Meunier B (1998) Efficient oxidation of 2’-deoxyguanosine by Mn-TMPyP/KHSO5 to imidazolone without formation of 8-oxodG. J Am Chem
Soc 120:11548–11553
94. Crean C, Geacintov NE, Shafirovich V (2008) Pathways of arachidonic acid peroxyl radical
reactions and product formation with guanine radicals. Chem Res Toxicol 21:358–373
95. Vialas C, Claparols C, Pratviel G () Meunier B (200) Guanine oxidation in double-stranded
DNAby Mn-TMPyP/KHSO5: 5,8-dihydroxy-7,8-dihydroguanine residue as a key precursor of imidazolone and parabanic acid derivatives. J Am Chem Soc 122:2157–2167
96. Niles JC, Wishnok JS, Tannenbaum SR (2001) Spiroiminohydantoin is the major product
of 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols, and
guanosine photooxidation by methylene blue. Org Lett 3:763–766
97. Luo WC, Muller JC, Rachlin E, Burrows CJ (2000) Characterization of spiroiminohydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine. Org Lett
2:613–617
98. Raoul S, Cadet J (1996) Photosensitized reaction of 8-oxo-7,8-dihydro-2’-deoxyguanosine.
identification of 1-(2-deoxy-beta-D-erythro-penofuransoyl)cyanuric acid as the major singlet oxygen oxidation product. J Am Chem Soc 118:1892–1898
99. Sheu C, Foote CS (1995) Photosensitized oxygenation of a 7,8-dihydro-8-oxoguanosine
derivative. Formation of dioxetane and hydroperoxide intermediates. J Am Chem Soc
117:474–477
100. Duarte V, Gasparutto D, Yamaguchi LF, Ravanat JL, Martinez GR, Medeiros MHG, Di
Mascio P, Cadet J (2000) Oxaluric acid as the major product of singlet oxygen mediated
oxidation of 8-oxo-7,8-dihydroguanine in DNA. J Am Chem Soc 122:12622–12628
101. Niles JC, Wishnok JS, Tannenbaum SR (2000) A novel nitration product formed during the
reaction of peroxynitrite with 2’,3’,5’-tri-O-acetyl-7,8-dihydro-8-oxoguanosine. Chem Res
Toxicol 13:390–396
102. Niles JC, Burney S, Singh SP, Wishnok JS, Tannenbaum SR (1999) Peroxynitrite reaction
products of 3’,5’-di-O-acetyl-8-oxo-7,8-dihydro-2’-deoxyuanosine. Proc Natl Acad Sci U
S A 96:11729–11734
103. Tretyakova NY, Niles JC, Burney S, Wishnok JS, Tannenbaum SR (1999) Peroxynitriteinduced reactions of synthetic oligonucleotides containing 8-oxoguanine. Chem Res Toxicol 12:459–466
104. Ravanat JL, Saint-Pierre C, Cadet J (2003) One-electron oxidation of the guanine moiety of
2’-deoxyguanosine: influence of 8-oxo-7,8-dihydro-2’-deoxyguanosine. J Am Chem Soc
125:2030–2031
105. Jena NR, Mishra PC (2006) Addition and hydrogen abstraction reactions of an OH radical
with 8-oxoguanine. Chem Phys Lett 422:417–423
106. Bashir S, Harris G, Denman MA, Blake DR, Winyard PG (1993) Oxidative DNA damage
and cellular sensitivity to oxidative stress in human autoimmune diseases. Ann Rheum Dis
52:659–666
107. Jena, NR, Mishra PC (2013) Is FapyG mutagenic: evidence from the DFT study. Chemphyschem 14:3263–3270.
108. Akaike T, Okamoto S, Sawa T, Yoshitake J, Tamura F, Ichimori K, Miyazaki K, Sasamoto
K, Maeda H (2003) 8-Nitroguanosine formation in viral pneumonia and its implication for
pathogenesis. Proc Natl Acad Sci U S A 100:685–690
109. Tuo J, Liu L, Poulsen HE, Weimann A, Svendsen O, Loft S (2000) Importance of guanine
nitration and hydroxylation in DNA in vitro and in vivo. Free Radic Biol Med 29:147–155
110. Halliwell B (2007) Oxidative stress and cancer: have we moved forward? Biochem J
401:1–11