Reactions between Hydroxyl-Radical-Induced 7,8-Dihydro-8-oxo-2′-deoxyguanosine Precursor and the Spin Trap α-Phenyl-N-tert-Butylnitrone

Journal of Radiation Research

Volumn 38, Issue 1, 1997, Pages 15-25

  Ohshima, Hideki ^a   Ono, Akira ^c   Matsuda, Akira ^b   Sawamura, Sadashi ^b   Kuwabara, Mikinori ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

7,8 Dihydro 8 oxo 2 deoxyguanosine; Hydroxyl radicals; Ionizing radiation; Spin trapping; Phenyl N tert butylnitrone

Indexed keywords

BIOMOLECULES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICAL REACTIONS; FREE RADICALS; PROTON TRANSFER; SODIUM COMPOUNDS; SOLUTIONS;

7,8-DIHYDRO-8-OXO-2′-DEOXYGUANOSINE; 8-OXODG; ESR SPECTRUM; HYDROXYL RADICALS; OH -; RADICAL SCAVENGERS; SPIN TRAP; SPIN TRAPPING; X-IRRADIATION; Α-PHENYL-N-TERT-BUTYLNITRONE;

IONIZING RADIATION;

LETHRINIDAE;

8 OXO 7 HYDRODEOXYGUANOSINE; 8-OXO-7-HYDRODEOXYGUANOSINE; DEOXYGUANOSINE; DRUG DERIVATIVE; HYDROXYL RADICAL; N TERT BUTYL ALPHA PHENYLNITRONE; NITROGEN OXIDE; PHENYL-N-TERT-BUTYLNITRONE; SCAVENGER;

ARTICLE; CHEMISTRY; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; RADIATION EXPOSURE; SPIN LABELING;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICAL SCAVENGERS; HYDROXYL RADICAL; NITROGEN OXIDES; SPIN LABELS;

EID: 0031091130     PISSN: 04493060     EISSN: None     Source Type: Journal    
DOI: 10.1269/jrr.38.15     Document Type: Article

References (31)

1. Fraga, C. G., Shigenaga, M. K., Park, J. W., Degan, P. and Ames, B. N. (1990) Oxidative damage to DNA during aging: 8-hydroxy-2′-deoxyguanosine in rat organ DNA and urine. Proc. Natl. Acad. Sci. USA 87: 4533-4537.
2. Sai, K., Takagi, A., Umemura, T., Hasegawa, R. and Kurokawa, Y. (1992) Changes of 8-hydroxydeoxyguanosine levels in rat organ DNA during the aging process. J. Environ. Pathol. Toxicol. Oncol. 11: 139-143.
3. Cattley, R. C. and Glover, S. E. (1993) Elevated 8-hydroxydeoxyguanosine in hepatic DNA of rats following exposure to peroxisome proliferators: relationship to carcinogenesis and nuclear localization. Carcinogenesis 14: 2495-2499.
4. Kasai, H. and Nishimura, S. (1984) Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res. 12: 2137-2145.
5. Kasai, H. and Nishimura, S. (1984) DNA damage induced by asbestos in the presence of hydrogen peroxide. Gann 75: 841-844.
6. Kasai, H., Tanooka, H. and Nishimura, S. (1984) Formation of 8-hydroxyguanine residues in DNA by X-irradiation. Gann 75: 1037-1039.
7. Dizdaroglu, M. (1985) Formation of an 8-hydroxyguanine moiety in deoxyribonucleic acid on γ-irradiation in aqueous solution. Biochemistry 24: 4476-4481.
8. Kasprzak, K. S. and Hernandez, L. (1989) Enhancement of hydroxylation and deglycosylation of 2′-deoxyguanosine by carcinogenic nickel compounds. Cancer Res. 49: 5964-5968.
9. Sharma, M., Box, H. C. and Paul, C. R. (1990) Detection and quantitation of 8-hydroxydeoxyguanosine 5′-monophosphate in X-irradiated calf thymus DNA by fluorescence postlabeling. Biochem. Biophys. Res. Comm. 167: 419-424.
10. Kuwabara, M., Inanami, O. and Sato, F. (1986) OH-induced free radicals in purine nucleosides and their homopolymers: e.s.r. and spin-trapping with 2-methyl-2-nitrosopropane. Int. J. Radiat. Biol. 49: 829-844.
11. Hiraoka, W., Kuwabara, M. and Sato, F. (1989) OH-induced free radicals in purine nucleoside monophosphates: e.s.r. and spin-trapping. Int. J. Radiat. Biol. 55: 51-58.
12. Ohshima, H., Iida, Y., Matsuda, A. and Kuwabara, M. (1996) Damage induced by hydroxyl radicals generated in the hydration layer of γ-iirradiated frozen aqueous solution of DNA. J. Radiat. Res. 37: 199-207.
13. Matsuda, A., Shinozaki, M., Suzuki, M., Watanabe, K. and Miyasaka, T. (1986) A convenient method for the selective acylation of guanine nucleosides. Synthesis 385-386.
14. Lin, T. S., Cheng, J. C., Ishiguro, K. and Sartorelli, A. C. (1985) 8-Substituted guanosine and 2′-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells. J. Med. Chem. 28: 1194-1198.
15. Henglein, A., Schnable, W. and Wendenburg, J. (1969) Ein Föhrung in die Strahlenchemie mit Praktischen Anleitungen, Verlag Chemie GmbH, Weinheim.
16. Kuwabara, M., Hiraoka, W., Sawamura, S. and Katayama, M. (1991) Reactions and rate constants between hydrated electrons and the monomer and dimer of 2-methyl-2-nitrosopropane determined by the pulse radiolysis method. J. Am. Chem. Soc. 113: 3995-3997.
17. Kuwabara, M., Miyake, S., Jin, T. and Sawamura, S. (1995) Reactions and rate constants between hydroxyl radicals and the dimer and monomer of spin trap 2-methyl-2-nitrosopropane determined by the pulse radiolysis method. J. Phys. Chem. 99: 14078-14082.
18. Park, J. W., Cundy, K. C. and Ames, B. N. (1989) Detection of DNA adducts by high-performance liquid chromatography with electrochemical detection. Carcinogenesis 10: 827-832.
19. Kagiya, T., Wada, T. and Nishimoto, S. (1984) Molecular mechanism of radiosensitization by nitro compounds. In "Modification of radiosensitivity in cancer treatment" Ed. Sugahara, T. pp. 85-108, Academic Press, Inc.
20. Janzen, E. G., Nutter, D. E., Jr., Davis, E. R., Blackburn, B. J. and McCay, P., B. (1978) On spin trapping hydroxyl and hydroperoxyl radicals. Can. J. Chem. 56: 2237-2242.
21. Buettner G. R. (1987) Spin trapping: ESR parameters of spin adducts. Free Rad. Biol. Med. 3: 259-303.
22. Sargent, F. P. and Gardy, E. M. (1976) Spin trapping of radicals formed during radiolysis of aqueous solutions. Direct electron spin resonance obserbations. Can. J. Chem. 54: 275-2279.
23. Anber, M., Bambenek, M. and Ross, A. B. (1973) Selected specific rates of reactions of transients from water in aqueous solution. I. hydrated electron. NSRDS-NBS 43.
24. la Verne, J. A. and Pimblott, S. M. (1993) Yields of hydroxyl radical and hydrated electron scavenging reactions in aqueous solutions of biological interest. Radiat. Res. 135: 16-23.
25. Simic, M. G. (1986) Free radical mechanism of DNA base damage. Mechanisms of DNA Damage and Repair. Edited by: Simic, M. G., Grossman, L and Upton, A. C. (Plenum Press, New York), pp. 39-49.
26. Devasagayam, T. P. A., Steenken, S., Obendorf, M. S. W., Schulz, W. A. and Sies, H. (1941) Formation of 8-hydroxy(deoxy)guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen. Biochemistry 30: 6283-6289.
27. Ravanat, J. L., Berger, M., Bénard, J. F., Langlois, R., Ouellet, R., van Lier, J. E. and Cadet, J. (1992) Phthalocyanine and naphthalocyanine photosensitized oxidation of 2′-deoxy-guanosine: distinct type I and type II products. Photochem. Photobiol. 55: 809-814.
28. Téoule, R. (1987) Radiation-induced DNA damage and its repair. Int. J. Radiat. Biol. 51: 573-589.
29. 10. Biochemistry 32: 10559-10606.
30. Inanami, O., Sato, F. and Kuwabara, M. (1993) The spin trap 2-methyl-2-nitrosopropane enhances hydroxyl-radical-induced degradation in historic H1 and inhibits hydroxyl-radical-induced intermolecular cross-links in histone H2B. Mol. Biol. (Life Sci. Adv.) 12: 133-144.
31. -) in an aqueous solution. J. Phys. Chem. Ref. Data 17: 513-886.