Photosensitized DNA damage induced by NADH: Site specificity and mechanism

References

• IARC Working Group. Solar and ultraviolet radiation. IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans. IARC, Lyon 1992; 55
   Google Scholar
• Setlow RB, Grist E, Thompson K, Woodhead AD. Wavelengths effective in induction of malignant melanoma. Proc Natl Acad Sci USA 1993; 90: 6666–6670
   PubMed Web of Science ®Google Scholar
• Drobetsky EA, Turcotte J, Chateauneuf A. A role for ultraviolet A in solar mutagenesis. Proc Natl Acad Sci USA 1995; 92: 2350–2354
   PubMed Web of Science ®Google Scholar
• Runger TM. Role of UVA in the pathogenesis of melanoma and non-melanoma skin cancer. A short review. Photodermatol Photoimmunol Photomed 1999; 15: 212–216
   PubMed Web of Science ®Google Scholar
• Agar NS, Halliday GM, Barnetson RS, Ananthaswamy HN, Wheeler M, Jones AM. The basal layer in human squamous tumors harbors more UVA than UVB fingerprint mutations: A role for UVA in human skin carcinogenesis. Proc Natl Acad Sci USA 2004; 101: 4954–4959
   PubMed Web of Science ®Google Scholar
• Morris RJ. Keratinocyte stem cells: Targets for cutaneous carcinogens. J Clin Invest 2000; 106: 3–8
   PubMed Web of Science ®Google Scholar
• Ananthaswamy HN, Pierceall WE. Molecular mechanisms of ultraviolet radiation carcinogenesis. Photochem Photobiol 1990; 52: 1119–1136
   PubMed Web of Science ®Google Scholar
• Tyrrell RM, Keyse SM. New trends in photobiology. The interaction of UVA radiation with cultured cells. J Photochem Photobiol B 1990; 4: 349–361
   PubMed Web of Science ®Google Scholar
• Kunisada M, Sakumi K, Tominaga Y, Budiyanto A, Ueda M, Ichihashi M, Nakabeppu Y, Nishigori C. 8-Oxoguanine formation induced by chronic UVB exposure makes Ogg1 knockout mice susceptible to skin carcinogenesis. Cancer Res 2005; 65: 6006–6010
   PubMed Web of Science ®Google Scholar
• Ito K, Inoue S, Yamamoto K, Kawanishi S. 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
   PubMed Web of Science ®Google Scholar
• Ito K, Kawanishi S. Photoinduced hydroxylation of deoxyguanosine in DNA by pterins: Sequence specificity and mechanism. Biochemistry 1997; 36: 1774–1781
   PubMed Web of Science ®Google Scholar
• Ito K, Kawanishi S. Site-specific DNA damage induced by UVA radiation in the presence of endogenous photosensitizer. Biol Chem 1997; 378: 1307–1312
   PubMed Web of Science ®Google Scholar
• Hirakawa K, Suzuki H, Oikawa S, Kawanishi S. Sequence-specific DNA damage induced by ultraviolet A-irradiated folic acid via its photolysis product. Arch Biochem Biophys 2003; 410: 261–268
   PubMed Web of Science ®Google Scholar
• Kawanishi S, Inoue S, Sano S, Aiba H. Photodynamic guanine modification by hematoporphyrin is specific for single-stranded DNA with singlet oxygen as a mediator. J Biol Chem 1986; 261: 6090–6095
   PubMed Web of Science ®Google Scholar
• Hiraku Y, Ito H, Kawanishi S. Site-specific hydroxylation at polyguanosine in double-stranded DNA by UVA radiation with nalidixic acid. Biochem Biophys Res Commun 1998; 251: 466–470
   PubMed Web of Science ®Google Scholar
• Hiraku Y, Kawanishi S. Distinct mechanisms of guanine-specific DNA photodamage induced by nalidixic acid and fluoroquinolone antibacterials. Arch Biochem Biophys 2000; 382: 211–218
   PubMed Web of Science ®Google Scholar
• Malaisse WJ, Hutton JC, Kawazu S, Herchuelz A, Valverde I, Sener A. The stimulus-secretion coupling of glucose-induced insulin release. XXXV. The links between metabolic and cationic events. Diabetologia 1979; 16: 331–341
   PubMed Web of Science ®Google Scholar
• Czochralska B, Kawczynski W, Bartosz G, Shugar D. Oxidation of excited-state NADH and NAD dimer in aqueous medium involvement of as a mediator in the presence of oxygen. Biochim Biophys Acta 1984; 801: 403–409
   Google Scholar
• Cunningham ML, Johnson JS, Giovanazzi SM, Peak MJ. Photosensitized production of superoxide anion by monochromatic (290–405 nm) ultraviolet irradiation of NADH and NADPH coenzymes. Photochem Photobiol 1985; 42: 125–128
   PubMed Web of Science ®Google Scholar
• Oikawa S, Kawanishi S. Site-specific DNA damage induced by NADH in the presence of copper(II): Role of active oxygen species. Biochemistry 1996; 35: 4584–4590
   PubMed Web of Science ®Google Scholar
• Chumakov P. EMBL Data Library 1990; Accession Number X54156.
   Google Scholar
• Yamashita N, Murata M, Inoue S, Hiraku Y, Yoshinaga T, Kawanishi S. Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II). Mutat Res 1998; 397: 191–201
   PubMed Web of Science ®Google Scholar
• Ito K, Yamamoto K, Kawanishi S. Manganese-mediated oxidative damage of cellular and isolated DNA by isoniazid and related hydrazines: Non-Fenton-type hydroxyl radical formation. Biochemistry 1992; 31: 11606–11613
   PubMed Web of Science ®Google Scholar
• Capon DJ, Chen EY, Levinson AD, Seeburg PH, Goeddel DV. Complete nucleotide sequences of the T24 human bladder carcinoma oncogene and its normal homologue. Nature 1983; 302: 33–37
   PubMed Web of Science ®Google Scholar
• Maxam AM, Gilbert W. Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol 1980; 65: 499–560
   PubMedGoogle Scholar
• Kasai H, Crain PF, Kuchino Y, Nishimura S, Ootsuyama A, Tanooka H. Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis 1986; 7: 1849–1851
   PubMed Web of Science ®Google Scholar
• Land EJ, Swallow AJ. One-electron reactions in biochemical systems as studied by pulse radiolysis. IV. Oxidation of dihydronicotinamide-adenine dinucleotide. Biochim Biophys Acta 1971; 234: 34–42
   PubMed Web of Science ®Google Scholar
• Czochralska B, Lindqvist L. Biphotonic one-electron oxidation of NADH on laser excitation at 353 nm. Chem Phys Lett 1983; 101: 297–299
   Web of Science ®Google Scholar
• Yamamoto K, Kawanishi S. Hydroxyl free radical is not the main active species in site-specific DNA damage induced by copper (II) ion and hydrogen peroxide. J Biol Chem 1989; 264: 15435–15440
   PubMed Web of Science ®Google Scholar
• Boiteux S, Gajewski E, Laval J, Dizdaroglu M. Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): Excision of purine lesions in DNA produced by ionizing radiation or photosensitization. Biochemistry 1992; 31: 106–110
   PubMed Web of Science ®Google Scholar
• Spassky A, Angelov D. Influence of the local helical conformation on the guanine modifications generated from one-electron DNA oxidation. Biochemistry 1997; 36: 6571–6576
   PubMed Web of Science ®Google Scholar
• Duarte V, Gasparutto D, Jaquinod M, Cadet J. In vitro DNA synthesis opposite oxazolone and repair of this DNA damage using modified oligonucleotides. Nucleic Acids Res 2000; 28: 1555–1563
   PubMed Web of Science ®Google Scholar
• Burrows CJ, Muller JG, Kornyushyna O, Luo W, Duarte V, Leipold MD, David SS. Structure and potential mutagenicity of new hydantoin products from guanosine and 8-oxo-7,8-dihydroguanine oxidation by transition metals. Environ Health Perspect 2002; 110(Suppl 5)713–717
   PubMed Web of Science ®Google Scholar
• Tretyakova NY, Wishnok JS, Tannenbaum SR. Peroxynitrite-induced secondary oxidative lesions at guanine nucleobases: Chemical stability and recognition by the Fpg DNA repair enzyme. Chem Res Toxicol 2000; 13: 658–664
   PubMed Web of Science ®Google Scholar
• Dherin C, Gasparutto D, O'Connor TR, Cadet J, Boiteux S. Excision by the human methylpurine DNA N-glycosylase of cyanuric acid, a stable and mutagenic oxidation product of 8-oxo-7,8-dihydroguanine. Int J Radiat Biol 2004; 80: 21–27
   PubMed Web of Science ®Google Scholar
• Prat F, Houk KN, Foote CS. Effect of guanine stacking on the oxidation of 8-oxoguanine in B-DNA. J Am Chem Soc 1998; 120: 845–846
   Web of Science ®Google Scholar
• Ravanat JL, Saint-Pierre C, Cadet J. One-electron oxidation of the guanine moiety of 2′-deoxyguanosine: Influence of 8-oxo-7,8-dihydro-2′-deoxyguanosine. J Am Chem Soc 2003; 125: 2030–2031
   PubMed Web of Science ®Google Scholar
• Kino K, Saito I, Sugiyama H. 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
   Web of Science ®Google Scholar
• Dizdaroglu M, Rao G, Halliwell B, Gajewski E. Damage to the DNA bases in mammalian chromatin by hydrogen peroxide in the presence of ferric and cupric ions. Arch Biochem Biophys 1991; 285: 317–324
   PubMed Web of Science ®Google Scholar
• Evans MD, Dizdaroglu M, Cooke MS. Oxidative DNA damage and disease: Induction, repair and significance. Mutat Res 2004; 567: 1–61
   PubMed Web of Science ®Google Scholar
• Higurashi M, Ohtsuki T, Inase A, Kusumoto R, Masutani C, Hanaoka F, Iwai S. Identification and characterization of an intermediate in the alkali degradation of (6–4) photoproduct-containing DNA. J Biol Chem 2003; 278: 51968–51973
   PubMed Web of Science ®Google Scholar
• Ono A, Okamoto T, Inada M, Nara H, Matsuda A. Nucleosides and nucleotides. 131. Synthesis and properties of oligonucleotides containing 5-formyl-2′-deoxyuridine. Chem Pharm Bull (Tokyo) 1994; 42: 2231–2237
   PubMed Web of Science ®Google Scholar
• Simon P, Gasparutto D, Gambarelli S, Saint-Pierre C, Favier A, Cadet J. Formation of isodialuric acid lesion within DNA oligomers via one-electron oxidation of 5-hydroxyuracil: Characterization, stability and excision repair. Nucleic Acids Res 2006; 34: 3660–3669
   PubMed Web of Science ®Google Scholar
• Peak JG, Peak MJ. Induction of slowly developing alkali-labile sites in human P3 cell DNA by UVA and blue- and green-light photons: Action spectrum. Photochem Photobiol 1995; 61: 484–487
   PubMed Web of Science ®Google Scholar
• Hockberger PE, Skimina TA, Centonze VE, Lavin C, Chu S, Dadras S, Reddy JK, White JG. Activation of flavin-containing oxidases underlies light-induced production of H2O2 in mammalian cells. Proc Natl Acad Sci USA 1999; 96: 6255–6260
   PubMed Web of Science ®Google Scholar
• Sakurai H, Yasui H, Yamada Y, Nishimura H, Shigemoto M. Detection of reactive oxygen species in the skin of live mice and rats exposed to UVA light: A research review on chemiluminescence and trials for UVA protection. Photochem Photobiol Sci 2005; 4: 715–720
   PubMed Web of Science ®Google Scholar
• Besaratinia A, Synold TW, Chen HH, Chang C, Xi B, Riggs AD, Pfeifer GP. DNA lesions induced by UVA1 and B radiation in human cells: Comparative analyses in the overall genome and in the p53 tumor suppressor gene. Proc Natl Acad Sci USA 2005; 102: 10058–10063
   PubMed Web of Science ®Google Scholar