DNA lesions caused by ROS and RNOS: A review of interactions and reactions involving guanine

Practical Aspects of Computational Chemistry: Methods, Concepts and Applications

Volumn , Issue , 2010, Pages 415-443

  Shukla, P K ^a   Mishra, P C ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84875411533     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-90-481-2687-3_22     Document Type: Chapter

References (159)

1. S. Steenken, Purine bases, nucleosides, and nucleotides: Aqueous solution redox chemistry and transformation reactions of their radical cations and e-and OH-adducts. Chem. Rev. 89, 503-520 (1989)
2. C.J. Burrows et al., Oxidative nucleobase modifications leading to strand scission. Chem. Rev. 98, 1109-1151 (1998)
3. B. Halliwell, Oxygen and nitrogen are pro-carcinogens. Damage to DNA by reactive oxygen, chlorine and nitrogen species: measurement, mechanism and the effects of nutrition. Mutat. Res. 443, 37-52 (1999)
4. J. Cadet et al., Oxidative damage to DNA: Formation, measurement and biochemical features. Mutat. Res. 531, 5-23 (2003)
5. H. Wiseman et al., Damage to DNA by reactive oxygen and nitrogen species: Role in inflammatory disease and progression to cancer. Biochem. J. 313, 17-29 (1996)
6. M.R. Bennett, Reactive oxygen species and death: Oxidative DNA damage in atherosclerosis. Circ. Res. 88, 648-650 (2001)
7. S. Magder, Reactive oxygen species: toxic molecules or spark of life? Crit. Care 10, 208 (2006)
8. J.P.E. Spencer et al., Nitrite-induced deamination and hypochlorite-induced oxidation of DNA in intact human respiratory tract epithelial cells. Free Radic. Biol. Med. 28, 1039-1050 (2000)
9. J. Barciszewski et al., Some unusual nucleic acid bases are products of hydroxyl radical oxidation of DNA and RNA. Mol. Biol. Rep. 26, 231-238 (1999)
10. J. Cadet et al., Hydroxyl radicals and DNA base damage. Mutat. Res. 424, 9-21 (1999)
11. P.C. Dedon et al., Reactive nitrogen species in the chemical biology of inflammation. Arch. Biochem. Biophys. 423, 12-22 (2004)
12. L.J. Marnett et al., Endogenous generation of reactive oxidants and electrophiles and their reactions with DNA and protein. J. Clin. Invest. 111, 583-593 (2003)
13. T. Suzuki, DNA damage and mutation caused by vital biomolecules, water, nitric oxide and hypochlorous acid. Genes Environ. 28, 48-55 (2006)
14. Y.A. Lee et al., Mechanisms of oxidation of guanine in DNA by carbonate radical anion, a decomposition product of nitrosoperoxycarbonate. Chem. Eur. J. 13, 4571-4581 (2007)
15. Y. Wang et al., Bulky DNA lesions induced by reactive oxygen species. Chem. Res. Toxicol. 21, 276-281 (2008)
16. Y. Mishina et al., Direct reversal of DNA alkylation damage. Chem. Rev. 106, 215-232 (2006)
17. M.D. Wyatt et al., Methylating agents and DNA repair responses: Methylated bases and sorces of strand breaks. Chem. Res. Toxicol. 19, 1580-1594 (2006)
18. P.K. Shukla et al., Reactions of guanine with methyl chloride and methyl bromide: O6-methylation versus charge transfer complex formation. Int. J. Quantum Chem. 107, 1270-1283 (2007)
19. P.K. Shukla et al., Reactions of DNA bases with the anti-cancer nitrogen mustard mechlor-ethamine: A quantum chemical study. Chem. Phys. Lett. 449, 323-328 (2007)
20. S. Shahin et al., Mitochondrial and nuclear DNA damage induced by sulphur mustard in keratinocytes. Chem. Biol. Interact. 138, 231-245 (2001)
21. J. Simons, How do low energy (0.1-2 eV) electrons cause DNA strand breaks. Acc. Chem. Res 39, 772-779 (2006)
22. J. Gu et al., Electron attachment-induced DNA single strand breaks: C3-O3 sigma-bond breaking of pyrimidine nucleotides predominates. J. Am. Chem. Soc. 128, 9322-9323 (2006)
23. Z. Li et al., Low energy electron induced DNA damage: effects of terminal phosphate and base moieties on the distribution of damage. J. Am. Chem. Soc. 130, 5612-5613 (2008)
24. Y. Zheng et al., DNA damage induced by low energy electrons: Electron transfer and diffraction. Phys. Rev. Lett. 96, 208101 (2006)
25. M.R. Osborne et al., Alkylation of DNA by the nitrogen mustard bis(2-chloroethyl) methyl-amine. Chem. Res. Toxicol. 8, 316-320 (1995)
26. D. Mu et al., Recognition and repair of compound DNA lesions (base damage and mismatch) by human mismatch repair and excision repair systems. Mol. Cell. Biol. 17, 760-769 (1997)
27. A.P. Grollman et al., Mutagenesis by 8-oxoguanine: an enemy within. Trends Genet. 9, 246-249 (1993)
28. 6-methylguanine and the cytotoxicity of methylating agents. Mutat. Res. 462, 71-82 (2000)
29. W.L. Neeley et al., Mechanisms of formation, genotoxicity, and mutation of guanine oxidation products. Chem. Res. Toxicol. 19, 491-505 (2006)
30. K.C. Cheng et al., 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G!T and A!T substitutions. J. Biol. Chem. 267, 166-172 (1992)
31. E.L. Loechler et al., In vivo mutagenesis by O6-methylguanine built into a unique site in a viral genome. Proc. Natl. Acad. Sci. U.S.A. 81, 6271-6275 (1984)
32. A.K. Singh et al., Mismatch base pairing of the mutagen 8-oxoguanine and its derivatives with adenine: A theoretical search for possible antimutagenic agents. Int. J. Quantum Chem. 102, 343-351 (2005)
33. G. Forde et al., Theoretical ab initio study of the effects of methylation on structure and stability of G:C Watson-Crick base pair. J. Biomol. Struct. Dyn. 20, 811-818 (2003)
34. B. Halliwell et al., Role of free radicals and catalytic metal ions in human disease: An overview. Methods Enzymol. 186, 1-85 (1990)
35. M.S. Cooke et al., Oxidative DNA damage: mechanisms, mutation, and disease. FASEB J. 17, 1195-1214 (2003)
36. G. Waris et al., Reactive oxygen species: Role in the development of cancer and various chronic conditions. J. Carcinog. 5, 14 (2006)
37. J. Tuo et al., Importance of guanine nitration and hydroxylation in DNA in vitro and in vivo. Free Radic. Biol. Med. 29, 147-155 (2000)
38. S.D. Bruner et al., Structural basis for recognition and repair of the endogenous mutagen 8-oxoguanine in DNA. Nature 403, 859 (2000)
39. M. Aslam et al., Reactive oxygen and nitrogen species in Alzheimer's disease. Curr. Alzheimer Res. 1, 111-119 (2004)
40. T. Finkel et al., Oxidants, oxidative stress and the biology of aging. Nature 408, 239-247 (2000)
41. J.E. Klaunig et al., The role of oxidative stress in carcinogenesis. Annu. Rev. Pharmacol. Toxicol. 44, 239-267 (2004)
42. R. Olinski et al., Oxidative DNA damage: Assessment of the role in carcinogenesis, atherosclerosis, and acquired immunodeficiency syndrome. Free Radic. Biol. Med. 33, 192-200 (2002)
43. A. Parihar et al., Oxidative stress and anti-oxidative mobilization in burn injury. Burns 34, 6-17 (2008)
44. J.S. Beckman et al., Apparent hydroxyl radical production by peroxynitrite: Implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. USA 87, 1620-1624 (1990)
45. P.C. Dedon, The chemical toxicology of 2-Deoxyribose oxidation in DNA. Chem. Res. Toxicol. 21, 206-219 (2008)
46. B. Halliwell et al., Measuring reactive species and oxidative damage in vivo and in cell culture: How should you do it and what do the results mean. British J. Phramacol. 142, 231-255 (2004)
47. V. Shafirovich et al., Photochemically catalyzed generation of site-specific 8-nitroguanine of long-lived neutral guanine radicals with nitrogen dioxide. Chem. Res. Toxicol. 15, 591-597 (2002)
48. M. Dong et al., Development of enzymatic probes of oxidative and nitrosative DNA damage caused by reactive nitrogen species. Mutat. Res. 594, 120-134 (2006)
49. J.C. Niles et al., Peroxynitrite-induced oxidation and nitration products of guanine and 8-oxoguanine: Structures and mechanisms of product formation. Nitric Oxide 14, 109-121 (2006)
50. R. Misiaszek et al., Oxidative DNA damage associated with combination of guanine and superoxide radicals and repair of mechanisms via radical trapping. J. Biol. Chem. 279, 32106-32115 (2004)
51. 2 molecule with guanine: A quantum computational study. J. Phys. Chem. B 109, 14205-14218 (2005)
52. N.R. Jena et al., Formation of 8-nitroguanine and 8-oxoguanine due to reactions of peroxynitrite with guanine. J. Comput. Chem. 28, 1321-1335 (2007)
53. 3 as a reactive oxygen species: formation of 8-oxoguanine from its reaction with guanine. J. Phys. Chem. B 111, 4603-4615 (2007)
54. 2 in the mutagenesis caused by reactions of ONOO-with guanine. J. Phys. Chem. B 112, 4779-44789 (2008)
55. J. Cadet et al., Assessment of oxidative base damage to isolated and cellular DNA by HPLC-MS/MS measurement. Free Radic. Biol. Med. 33, 441-449 (2002)
56. J.-L. Ravanat et al., Singlet oxygen oxidation of 2'-deoxyguanosine. Formation and mechanistic insights. Tetrahedron 62, 10709-10715 (2006)
57. Y.H. Jang et al., First principle calculations of the tautomers and pKa values of 8-oxoguanine: Implications for mutagenicity and repair. Chem. Res. Toxicol. 15, 1023-1035 (2002)
58. V.I. Bruskov et al., Heat-induced formation of reactive oxygen species and 8-oxoguanine, a biomarker of damage to DNA. Nucleic Acids Res. 30, 1354-1363 (2002)
59. X. Cheng et al., Dynamic behavior of DNA base pairs containing 8-oxoguanine. J. Am. Chem. Soc. 127, 13906-13918 (2005)
60. R. Saffhill et al., Mechanisms of carcinogenesis induced by alkylating agents. Biochim. Biophys. Acta 823, 111-145 (1985)
61. D.T. Beranek, Distribution of methyl and ethyl adducts following alkylation with monofunctional alkylating agents. Mutat. Res. 231, 11-30 (1990)
62. S.A. Kyrtopoulos et al., DNA adducts in humans after exposure to methylating agents. Mutat. Res. 405, 135-143 (1998)
63. K.S. Ekanayake et al., Activation barriers for DNA alkylation by carcinogenic methane diazonium ions. J. Comput. Chem. 27, 277-286 (2006)
64. G.K. Forde et al., Comprehensive study of the effects of methylation on tautomeric equilibria of nucleic acid bases. J. Phys. Chem. B 110, 15564-15571 (2006)
65. A.C. Povey et al., Elevated levels of the pro-carcinogenic adduct, O6-methylguanine, in normal DNA from the cancer prone regions of the large bowel. Gut 47, 362-365 (2000)
66. G.P. Margison et al., O6-alkylguanine-DNA alkyltransferase: Role in carcinogenesis and chemotherapy. Bioessays 24, 255-266 (2002)
67. H.J. Helbock et al., 8-Hydroxydeoxyguanosine and 8-hydroxyguanine as biomarkers of oxidative DNA damag. Methods Enzymol. 300, 155-166 (1999)
68. S. Shibutani et al., Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature 349, 431-434 (1991)
69. H. Maki et al., MutT protein specifically hydrolyses a potent mutagenic substrate for DNA synthesis. Nature 355, 273-275 (1992)
70. T.K. Hazra et al., Repair of hydantoins, one electron oxidation product of 8-oxoguanine by DNA glycosylases of Escherichia coli. Nucleic Acids Res. 29, 1967-1974 (2001)
71. O.M. Panasenko et al., Oxidative modification and nitration of human low-density lipopro-teins by the reaction of hypochlorous acid with nitrite. Arch. Biochem. Biophys. 343, 254-259 (1997)
72. A.C. Carr et al., The nitric oxide congener nitrite inhibits myeloperoxidase/H2O2/Cl-mediated modification of low density lipoprotein. J. Biol. Chem. 276, 1822-1828 (2001)
73. F. Yamakura et al., Modification of tryptophan and tryptophan residues in proteins by reactive nitrogen species. Nitric Oxide 14, 152-161 (2006)
74. M. Whiteman et al., Lack of tyrosine nitration by hypochlorous acid in the presence of physiological concentration of nitrite. J. Biol. Chem. 278, 8380-8384 (2003)
75. A.S. Ptolemy et al., Strategies for comprehensive analysis of amino acid biomarkers of oxidative stress. Amino Acids 33, 3-18 (2007)
76. N.R. Jena et al., Reaction of hypochlorous acid with imidazole: Formation of 2-chloro-and 2-oxoimidazoles. J. Comput. Chem. 29, 98-107 (2008)
77. O. Augusto et al., Nitrogen dioxide and carbonate radical anion: Two emerging radicals in biology. Free Radic. Biol. Med. 32, 841-859 (2002)
78. 2Cl with imidazole: A model study for the corresponding reactions of guanine. J. Phys. Chem. B 112, 7925-7936 (2008)
79. M.G. Bonini et al., Production of the carbonate radical anion during xanthine oxidase turnover in the presence of bicarbonate. J. Biol. Chem. 279, 51836-51843 (2004)
80. J.F. Turrens, Mitochondrial formation of reactive oxygen species. J. Physiol. 552, 335-344 (2003)
81. Y. Xia et al., Superoxide and peroxynitrite generation from inducible nitric oxide synthase in macrophages. Proc. Natl Acad. Sci. USA 94, 6954-6958 (1997)
82. J.F. Torrens et al., Ubisemiquinone is the electron donor for superoxide formation by complex III of heart mito. Arch. Biochem. Biophys. 237, 408-414 (1985)
83. G.L. Squadrito et al., Oxidative chemistry of nitric oxide: The roles of superoxide, perox-ynitrite, and carbon dioxide. Free Radic. Biol. Med. 25, 392-403 (1998)
84. J. Carlsson et al., Hydrogen peroxide and superoxide radical formation in anaerobic broth media exposed to atmospheric oxygen. Appl. Environ. Microbiol. 36, 223-229 (1978)
85. W.A. Pryor et al., The chemistry of peroxynitrite: A product from the reaction of nitric oxide with superoxide. Am. J. Physiol. 268, L699-L722 (1995)
86. R. Misiaszek et al., Combination reactions of superoxide with 8-oxoG radicals in DNA: kinetics and enol products. J. Biol. Chem. 280, 6293-6300 (2005)
87. 2. Chem.-Biol. Intteract 80, 239-260 (1992)
88. D.B. Min et al., Chemistry and reaction of singlet oxygen in foods. Compr. Rev. Food Sci. Food Safety 1, 58-72 (2002)
89. F. Wilkinson et al., Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 22, 113-262 (1993)
90. P.F. Santos et al., Singlet oxygen generation ability of squarylium cyanine dyes. J. Photochem. Phtobiol. A 160, 159-161 (2003)
91. E. Skovsen et al., Two-photon singlet oxygen microscopy: The challenges of working with single cells. Photochem. Photobiol. 73, 1187-1197 (2006)
92. P.C. Mishra et al., Interaction of singlet oxygen and superoxide radical anion with guanine and formation of its mutagenic modification 8-oxoguanine. Int. J. Quantum Chem. 102, 282-301 (2005)
93. J.M. McCord et al., Superoxide dismutase. An enzymatic function for erythrocuprein (hemocuprein). J. Biol. Chem 244, 6049-6055 (1969)
94. I. Fridovich, Superoxide radical and superoxide dismutases. Annu. Rev. Biochem. 64, 97-112 (1995)
95. H.G.D. Niekus et al., Superoxide dismutase and hydrogen peroxide formation in campylobacter sptorum subspecies bubulus. Arch. Microbiol. 119, 37-42 (1978)
96. R. Kevin et al., Mechanism of superoxide and hydrogen peroxide formation by fumarate reductases, succinate dehydrogenase, aspartate oxidase. J. Biol. Chem. 277, 42563-42571 (2002)
97. L. Brambilla et al., Mitochondrial formation of hydrogen peroxide is casually linked to the antimycin A-mediated prevention of tert- butylhydroperoxide-induced U937 cell death. FEBS Lett. 431, 245-249 (1998)
98. 2 by peroxisomes. Free Radic. Biol. Med. 42, 1119-1129 (2007)
99. B.M. Babior, Phagocytes and oxidative stress. Am. J. Med. 109, 33-44 (2000)
100. E. Graf et al., Iron-catalyzed hydroxyl radical formation. Stringent requirement for free iron coordination site. J. Biol. Chem 259, 3620-3624 (1984)
101. H. Fickl et al., Vanadium promotes hydroxyl radical formation by activated human neutrophils. Free Radic. Biol. Med. 40, 146-155 (2006)
102. J.P. Kehrer, The Haber-Weiss reaction and mechanisms of toxicity. Toxicology 149, 43-50 (2000)
103. L.P. Candeias et al., Reaction of HO-with guanine derivatives in aqueous solution: Formation of two different redox active OH-adduct radicals and their unimolecular transformation reactions. Properties of G(-H). Chem. Eur. J 6, 475-484 (2000)
104. N.R. Jena et al., Addition and hydrogen abstraction reactions of an OH-radical with 8-oxoguanine. Chem. Phys. Lett. 422, 417-423 (2006)
105. Y.J. Ji et al., Theoretical study of the OH-reaction with cytosine. J. Mol. Struct.: THEOCHEM 723, 123-129 (2005)
106. J. Llano et al., Mechanism of hydroxyl radical addition to imidazole and subsequent water elimination. J. Phys. Chem. B 103, 5598-5607 (1999)
107. W. Hiraoka et al., Free-radical reactions induced by OH-radical attack on cytosine-related compounds: a study by a method combining ESR, spin trapping and HPLC. Nucleic Acids Res. 18, 1217-1223 (1990)
108. Y. Wu et al., On the Mechanisms of OH-Radical Induced DNA-Base Damage: A Comparative Quantum Chemical and Car-Parrinello Molecular Dynamics Study. J. Phys. Chem. A 108, 2922-2929 (2004)
109. P. Schyaman et al., Hydroxyl radical-thymine adduct induced DNA damage. Chem. Phys. Lett. 458, 186-189 (2008)
110. S. Sun et al., Radical-mediated cytosine and S-methylcytosine hydrolytic deamination reactions. Int. J. Quantum Chem. 106, 1878-1894 (2006)
111. A. Grand et al., H atom and OH-radical reactions with 5-methylcytosine. J. Phys. Chem. A 111, 8968-8972 (2007)
112. B.G. Eatock et al., Ab intio SCF MO calculation on the reaction of hydroxyl radical with cytosine. Can. J. Chem. 64, 914-919 (1986)
113. C.S. Foote et al., Assessment of chlorination by human neutrophills. Nature 301, 715-716 (1983)
114. M. Masuda et al., Chlorination of guanosine and other nucleosides by hypochlorous acid and myeloperoxidase of activated human neutrophils. J. Biol. Chem. 276, 40486-40496 (2001)
115. J. Marcinkiewicz et al., Antimicrobial and cytotoxic activity of hypochlorous acid: Interactions with taurine and nitrite. Inflamm. Res. 49, 280-289 (2000)
116. M. Whiteman et al., Hypochlorous acid-induced DNA base modification: Potentiation by nitrite: Biomarkers of DNA damage by reactive oxygen species. Biochem. Biophys. Res. Commun. 257, 572-576 (1999)
117. P.T. Nyffeller et al., Dihydrogen trioxide (HOOOH) is generated during the thermal reaction between hydrogen peroxide and ozone. Angew. Chem. Int. Ed. 43, 4656-4659 (2004)
118. B. Plesnicar, Progress in the chemistry of dihydrogen trioxide (HOOOH). Acta Chim. Slov. 52, 1-12 (2005)
119. P. Wentworth et al., Antibody catalysis of the oxidation of water. Science 273, 1806-1811 (2001)
120. B.H.J. Bielski et al., Absorption spectra and kinetics of hydrogen sesquioxide and the perhydroxyl radical. J. Phys. Chem. 72, 3836-3841 (1968)
121. 2. Chem. Phys. Lett. 33, 479-482 (1975)
122. 3. Science 295, 482-483 (2002)
123. K. Suma et al., The rotational spectrum and structure of HOOOH. J. Am. Chem. Soc. 127, 14998-14999 (2005)
124. X. Xu et al., The gas phase reaction of singlet oxygen with water: A water-catalyzed mechanism. Proc. Natl. Acad. Sci. USA 99, 3376-3381 (2002)
125. D.J. Mckay et al., How long can you make an oxygen chain. J. Am. Chem. Soc. 120, 1003-1013(1999)
126. F.B. Jensen, Nitric oxide formation from the reaction of nitrite with carp and rabit hemoglobin at intermediate oxygen saturations. FEBS J. 275, 3375-3387 (2008)
127. H. Ischiropoulos, Biological tyrosine nitration: A pathophysiological function of nitric oxide and reactive oxygen species. Arch. Biochem. Biophys. 356, 1-11 (1998)
128. J.P. Kiss, Role of nitric oxide in the regulation of monoaminergic neurotransmission. Brain Res. Bullet. 52, 459-466 (2000)
129. 2-catalyzed one-electron oxidations by peroxynitrite: Properties of the reactive intermediate. Inorg. Chem. 37, 294-301 (1998)
130. R.M. Uppu et al., Acceleration of peroxynitrite oxidations by carbon dioxide. Arch. Biochem. Biophys. 327, 335-343 (1996)
131. A. Denicola et al., Peroxynitrite reaction with carbon dioxide/bicarbonate: Kinetics and influence on peroxynitrite-mediated oxidations. Arch. Biochem. Biophys. 333, 49-58 (1996)
132. 2: Evidence for carbonate radical production. J. Am. Chem. Soc. 120, 3458-3463 (1998)
133. 2: Energetics, reactive species, and biological implications. Chem. Res. Toxicol. 15, 885-895 (2002)
134. M.G. Bonini et al., Direct EPR detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide. J. Biol. Chem. 274, 10802-10806 (1999)
135. M.C. Gonzalez et al., QM-MM investigation of the reaction of peroxynitrite with carbon dioxide in water. J. Chem. Theory Comput. 3, 1405-1411 (2007)
136. S. Steenken et al., How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J. Am. Chem. Soc. 119, 617-618 (1997)
137. C. Richter et al., Normal oxidative damage to mitochondrial and nuclear DNA is extensive. Proc. Natl. Acad. Sci. USA 85, 6465-6467 (1988)
138. M.K. Shigenaga et al., Urinary 8-hydroxy-2-deoxyguanosine as a biological marker of in vivo oxidative DNA damage. Proc. Natl. Acad. Sci. USA 86, 9697-9701 (1989)
139. D.C. Malins et al., Major alterations in the nucleotide structure of DNA in cancer of the female breast. Cancer Res. 51, 30-32 (1991)
140. S.J. Culp et al., Structural and conformational analyses of 8-hydroxy-2-deoxyguanosine. Chem. Res. Toxicol. 2, 416-422 (1989)
141. D. Venkateswarlu et al., Tautomeric equilibria in 8-oxopurines: Implications for mutagenic-ity. J. Comput.-Aid. Mol. Design 12, 373-382 (1998)
142. L.G. Brieba et al., Structural basis for the dual coding potential of 8-oxoguanosine by a high-fidelity DNA polymerase. EMBO J. 23, 3452-3461 (2004)
143. N. Suzuki et al., Miscoding Events during DNA Synthesis Past the Nitration-Damaged Base 8-Nitroguanine. Biochemistry 44, 9238-9245 (2005)
144. K.J. Laidler, Chemical Kinetics, third edn. (Pearson Education (Singapore) Pte. Ltd, Delhi, India, 2004)
145. I.N. Levine, Quantum Chemistry, fourth edn. (Prentice-Hall, Inc, Englewood Cliffs, N.J., USA, 1994)
146. S. Olivella et al., Mechanisms for the reaction of hydroxyl radicals with acrolein: A theoretical study. J. Chem. Theory Comput. 4, 941-950 (2008)
147. 3 + N of importance in boron nitride chemistry. Chem. Phys. Lett. 413, 151-156 (2005)
148. 3 molecule. J. Mol. Struct. (THEOCHEM) 531, 283-299 (2000)
149. A.D. Becke, Density-functional thermochemistry. III. The role of exact exchange, J. Chem. Phys. 98, 5648 (1993)
150. C. Lee et al., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785-789 (1988)
151. M.J. Frisch et al., A direct MP2 gradient method. Chem. Phys. Lett. 166, 275-280 (1990)
152. M.J. Frisch et al., Semi-direct algorithms for the MP2 energy and gradient. Chem. Phys. Lett. 166, 281-289 (1990)
153. B. Mennucci et al., Continuum solvation models: A new approach to the problem of solute's charge distribution and cavity boundaries. J. Chem. Phys. 106, 5151 (1997)
154. C. Gonzalez et al., An improved algorithm for reaction path following. J. Chem. Phys. 90, 2154 (1989)
155. J. Koller et al., Mechanism of the participation of water in the decomposition of hydrogen trioxide (HOOOH). A theoretical study. J. Am. Chem. Soc. 118, 2470-2472 (1996)
156. J.A. Kerr, Bond dissociation energies by kinetics methods. Chem. Rev. 66, 465-500 (1966)
157. 2. J. Electron Spectrosc. 97, 131-146 (1998)
158. V. Gogonea, Potential energy surface of the reaction of imidazole with peroxynitrite: density functional theory study. Int. J. Quantum Chem. 104, 342-353 (2005)
159. C. Crean et al., Oxidation of guanine and 8-oxo-7, 8-dihydroguanine by carbonate radical anions: Insight from oxygen-18 labeling experiments. Angew. Chem. Int. Ed. 44, 5057-5060 (2005)