Photosensitized DNA damage induced by NADH: Site specificity and mechanism

Free Radical Research

Volumn 41, Issue 4, 2007, Pages 461-468

  Ito, Kimiko ^a   Hiraku, Yusuke ^b   Kawanishi, Shosuke ^b,c  

^a Tsu City College   (Japan)

^b MIE UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^c SUZUKA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

Author keywords

8 oxo 7,8 dihydro 2 deoxyguanosine; DNA damage; Hydrogen peroxide; NADH; UVA

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; BATHOCUPROINE; CATALASE; CHELATING AGENT; COPPER; DNA FORMAMIDOPYRIMIDINE GLYCOSYLASE; DNA FRAGMENT; GUANINE; HYDROGEN PEROXIDE; PHOSPHORUS 32; PIPERIDINE; PROTEIN P53; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; RIBOFLAVIN; THYMINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DNA CLEAVAGE; DNA DAMAGE; DNA MODIFICATION; ELECTRON TRANSPORT; HUMAN; HUMAN CELL; NUCLEIC ACID ANALYSIS; OXIDATION REDUCTION REACTION; PATHOPHYSIOLOGY; PHOTOSENSITIZATION; RADIATION CARCINOGENESIS; RADIATION EXPOSURE; RADIATION HAZARD; RADIATION PROTECTION; SKIN CANCER; TUMOR SUPPRESSOR GENE; ULTRAVIOLET RADIATION;

ANIMALS; CATTLE; DEOXYGUANOSINE; DNA DAMAGE; DNA FRAGMENTATION; DNA-FORMAMIDOPYRIMIDINE GLYCOSYLASE; GENES, P53; HUMANS; HYDROGEN PEROXIDE; LIGHT; NAD; PHOTOSENSITIZING AGENTS; RIBOFLAVIN; TUMOR SUPPRESSOR PROTEIN P53; ULTRAVIOLET RAYS;

EID: 33947527538     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760601145240     Document Type: Article

References (46)

1. IARC Working Group (1992) Solar and ultraviolet radiation. IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans, 55, IARC, Lyon
2. Setlow, RB, Grist, E., Thompson, K. and Woodhead, AD (1993) Wavelengths effective in induction of malignant melanoma. Proc Natl Acad Sci USA, 90, pp. 6666-6670.
3. Drobetsky, EA, Turcotte, J. and Chateauneuf, A. (1995) A role for ultraviolet A in solar mutagenesis. Proc Natl Acad Sci USA, 92, pp. 2350-2354.
4. Runger, TM (1999) Role of UVA in the pathogenesis of melanoma and non-melanoma skin cancer. A short review. Photodermatol Photoimmunol Photomed, 15, pp. 212-216.
5. Agar, NS, Halliday, GM, Barnetson, RS, Ananthaswamy, HN, Wheeler, M. and Jones, AM (2004) 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, 101, pp. 4954-4959.
6. Morris, RJ (2000) Keratinocyte stem cells: Targets for cutaneous carcinogens. J Clin Invest, 106, pp. 3-8.
7. Ananthaswamy, HN and Pierceall, WE (1990) Molecular mechanisms of ultraviolet radiation carcinogenesis. Photochem Photobiol, 52, pp. 1119-1136.
8. Tyrrell, RM and Keyse, SM (1990) New trends in photobiology. The interaction of UVA radiation with cultured cells. J Photochem Photobiol B, 4, pp. 349-361.
9. Kunisada, M., Sakumi, K., Tominaga, Y., Budiyanto, A., Ueda, M., Ichihashi, M., Nakabeppu, Y. and Nishigori, C. (2005) 8-Oxoguanine formation induced by chronic UVB exposure makes Ogg1 knockout mice susceptible to skin carcinogenesis. Cancer Res, 65, pp. 6006-6010.
10. Ito, K., Inoue, S., Yamamoto, K. and Kawanishi, S. (1993) 8-Hydroxydeoxyguanosine formation at the 5′ site of 5′-GG-3′ sequences in double-stranded DNA by UV radiation with riboflavin. J Biol Chem, 268, pp. 13221-13227.
11. Ito, K. and Kawanishi, S. (1997) Photoinduced hydroxylation of deoxyguanosine in DNA by pterins: Sequence specificity and mechanism. Biochemistry, 36, pp. 1774-1781.
12. Ito, K. and Kawanishi, S. (1997) Site-specific DNA damage induced by UVA radiation in the presence of endogenous photosensitizer. Biol Chem, 378, pp. 1307-1312.
13. Hirakawa, K., Suzuki, H., Oikawa, S. and Kawanishi, S. (2003) Sequence-specific DNA damage induced by ultraviolet A-irradiated folic acid via its photolysis product. Arch Biochem Biophys, 410, pp. 261-268.
14. Kawanishi, S., Inoue, S., Sano, S. and Aiba, H. (1986) Photodynamic guanine modification by hematoporphyrin is specific for single-stranded DNA with singlet oxygen as a mediator. J Biol Chem, 261, pp. 6090-6095.
15. Hiraku, Y., Ito, H. and Kawanishi, S. (1998) Site-specific hydroxylation at polyguanosine in double-stranded DNA by UVA radiation with nalidixic acid. Biochem Biophys Res Commun, 251, pp. 466-470.
16. Hiraku, Y. and Kawanishi, S. (2000) Distinct mechanisms of guanine-specific DNA photodamage induced by nalidixic acid and fluoroquinolone antibacterials. Arch Biochem Biophys, 382, pp. 211-218.
17. Malaisse, WJ, Hutton, JC, Kawazu, S., Herchuelz, A., Valverde, I. and Sener, A. (1979) The stimulus-secretion coupling of glucose-induced insulin release. XXXV. The links between metabolic and cationic events. Diabetologia, 16, pp. 331-341.
18. Czochralska, B., Kawczynski, W., Bartosz, G. and Shugar, D. (1984) Oxidation of excited-state NADH and NAD dimer in aqueous medium involvement of as a mediator in the presence of oxygen. Biochim Biophys Acta, 801, pp. 403-409.
19. Cunningham, ML, Johnson, JS, Giovanazzi, SM and Peak, MJ (1985) Photosensitized production of superoxide anion by monochromatic (290-405 nm) ultraviolet irradiation of NADH and NADPH coenzymes. Photochem Photobiol, 42, pp. 125-128.
20. Oikawa, S. and Kawanishi, S. (1996) Site-specific DNA damage induced by NADH in the presence of copper(II): Role of active oxygen species. Biochemistry, 35, pp. 4584-4590.
21. Yamashita, N., Murata, M., Inoue, S., Hiraku, Y., Yoshinaga, T. and Kawanishi, S. (1998) Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II). Mutat Res, 397, pp. 191-201.
22. Ito, K., Yamamoto, K. and Kawanishi, S. (1992) Manganese-mediated oxidative damage of cellular and isolated DNA by isoniazid and related hydrazines: Non-Fenton-type hydroxyl radical formation. Biochemistry, 31, pp. 11606-11613.
23. Capon, DJ, Chen, EY, Levinson, AD, Seeburg, PH and Goeddel, DV (1983) Complete nucleotide sequences of the T24 human bladder carcinoma oncogene and its normal homologue. Nature, 302, pp. 33-37.
24. Maxam, AM and Gilbert, W. (1980) Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol, 65, pp. 499-560.
25. Kasai, H., Crain, PF, Kuchino, Y., Nishimura, S., Ootsuyama, A. and Tanooka, H. (1986) Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis, 7, pp. 1849-1851.
26. Land, EJ and Swallow, AJ (1971) One-electron reactions in biochemical systems as studied by pulse radiolysis. IV. Oxidation of dihydronicotinamide-adenine dinucleotide. Biochim Biophys Acta, 234, pp. 34-42.
27. Czochralska, B. and Lindqvist, L. (1983) Biphotonic one-electron oxidation of NADH on laser excitation at 353 nm. Chem Phys Lett, 101, pp. 297-299.
28. Yamamoto, K. and Kawanishi, S. (1989) 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, 264, pp. 15435-15440.
29. Boiteux, S., Gajewski, E., Laval, J. and Dizdaroglu, M. (1992) Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): Excision of purine lesions in DNA produced by ionizing radiation or photosensitization. Biochemistry, 31, pp. 106-110.
30. Spassky, A. and Angelov, D. (1997) Influence of the local helical conformation on the guanine modifications generated from one-electron DNA oxidation. Biochemistry, 36, pp. 6571-6576.
31. Duarte, V., Gasparutto, D., Jaquinod, M. and Cadet, J. (2000) In vitro DNA synthesis opposite oxazolone and repair of this DNA damage using modified oligonucleotides. Nucleic Acids Res, 28, pp. 1555-1563.
32. Burrows, CJ, Muller, JG, Kornyushyna, O., Luo, W., Duarte, V., Leipold, MD and David, SS (2002) Structure and potential mutagenicity of new hydantoin products from guanosine and 8-oxo-7,8-dihydroguanine oxidation by transition metals. Environ Health Perspect, 110, pp. 713-717.
33. Tretyakova, NY, Wishnok, JS and Tannenbaum, SR (2000) Peroxynitrite-induced secondary oxidative lesions at guanine nucleobases: Chemical stability and recognition by the Fpg DNA repair enzyme. Chem Res Toxicol, 13, pp. 658-664.
34. Dherin, C., Gasparutto, D., O'Connor, TR, Cadet, J. and Boiteux, S. (2004) 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, 80, pp. 21-27.
35. Prat, F., Houk, KN and Foote, CS (1998) Effect of guanine stacking on the oxidation of 8-oxoguanine in B-DNA. J Am Chem Soc, 120, pp. 845-846.
36. Ravanat, JL, Saint-Pierre, C. and 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, pp. 2030-2031.
37. Kino, K., Saito, I. and Sugiyama, H. (1998) Product analysis of GG-specific photooxidation of DNA via electron transfer: 2-Aminoimidazolone as a major guanine oxidation product. J Am Chem Soc, 120, pp. 7373-7374.
38. Dizdaroglu, M., Rao, G., Halliwell, B. and Gajewski, E. (1991) Damage to the DNA bases in mammalian chromatin by hydrogen peroxide in the presence of ferric and cupric ions. Arch Biochem Biophys, 285, pp. 317-324.
39. Evans, MD, Dizdaroglu, M. and Cooke, MS (2004) Oxidative DNA damage and disease: Induction, repair and significance. Mutat Res, 567, pp. 1-61.
40. Higurashi, M., Ohtsuki, T., Inase, A., Kusumoto, R., Masutani, C., Hanaoka, F. and Iwai, S. (2003) Identification and characterization of an intermediate in the alkali degradation of (6-4) photoproduct-containing DNA. J Biol Chem, 278, pp. 51968-51973.
41. Ono, A., Okamoto, T., Inada, M., Nara, H. and Matsuda, A. (1994) Nucleosides and nucleotides. 131. Synthesis and properties of oligonucleotides containing 5-formyl-2′-deoxyuridine. Chem Pharm Bull (Tokyo), 42, pp. 2231-2237.
42. Simon, P., Gasparutto, D., Gambarelli, S., Saint-Pierre, C., Favier, A. and Cadet, J. (2006) Formation of isodialuric acid lesion within DNA oligomers via one-electron oxidation of 5-hydroxyuracil: Characterization, stability and excision repair. Nucleic Acids Res, 34, pp. 3660-3669.
43. Peak, JG and Peak, MJ (1995) Induction of slowly developing alkali-labile sites in human P3 cell DNA by UVA and blue- and green-light photons: Action spectrum. Photochem Photobiol, 61, pp. 484-487.
44. 2 in mammalian cells. Proc Natl Acad Sci USA, 96, pp. 6255-6260.
45. Sakurai, H., Yasui, H., Yamada, Y., Nishimura, H. and Shigemoto, M. (2005) 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, 4, pp. 715-720.
46. Besaratinia, A., Synold, TW, Chen, HH, Chang, C., Riggs, AD and Pfeifer, GP (2005) 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, 102, pp. 10058-10063.