Formation of DNA adducts and oxidative base damage by copper mediated oxidation of dopamine and 6-hydroxydopamine

Experimental Neurology

Volumn 146, Issue 2, 1997, Pages 570-574

  Lévay, György ^a,b   Ye, Qiuping ^b   Bodell, William J ^b  

^a EGIS PHARMACEUTICALS LTD   (Hungary)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; COPPER; DOPAMINE; OXIDOPAMINE; PEROXIDE;

ARTICLE; DNA ADDUCT; DNA DAMAGE; DOPAMINERGIC NERVE CELL; NERVE CELL NECROSIS; NERVE DEGENERATION; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PARKINSON DISEASE; PRIORITY JOURNAL;

EID: 0031214246     PISSN: 00144886     EISSN: None     Source Type: Journal    
DOI: 10.1006/exnr.1997.6560     Document Type: Article

References (44)

1. 1. Ames, B. N., M. K. Shigenaga, and T. M. Hagen. 1993. Oxidants, antioxidants, and the degenerative diseases of aging. Proc. Natl. Acad. Sci. USA 90: 7915-7922.
2. 2. Archibald, F. S., and C. Tyree. 1987. Manganese poisoning and the attack of trivalent manganese upon catecholamines. Arch. Biochem. Biophys. 256: 638-650.
3. 3. Aronovitch, J., D. Godinger, and G. Czapski. 1991. Hydrogen peroxide dependent oxidative degradation of DNA by copper epinephrine. Free Radicals Res. Commun. 12-13: 499-508.
4. 4. Aruoma, O. I., B. Halliwell, E. Gajewski, and M. Dizdaroglu. 1991. Copper ion dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochem J. 273: 601-604.
5. 32P-postlabelling of DNA adducts induced by a Fenton-type oxygen radical generating system. Carcinogenesis 13: 1127-1135.
6. 32P-postlabeling. Mutat. Res. 291: 147-159.
7. 7. Chevion, M. 1988. A site specific mechanism for free radical induced biological damage: The essential role of redox-active transition metals. Free Radicals Biol. Med. 5: 27-37.
8. 8. Cohen, G., and R. E. Heikkila. 1974. The generation of hydrogen peroxide, superoxide radical, and hydroxyl radical by 6-hydroxydopamine, dialuric acid, and related cytotoxic agents. J. Biol. Chem. 249: 2447-2452.
9. 9. Dexter, D. T., F. R. Wells, A. J. Lees, F. Agid, Y. Agid, P. Jenner, and C. D. Marsden. 1989. Increased nigral iron content and alterations in other metal ions occurring in brain in Parkinson's disease. J. Neurochem. 52: 1830-1836.
10. 10. Dexter, D. T., A. Carayon, F. Javoy-Agid, Y. Agid, F. R. Wells, S. E. Daniel, A. J. Lees, P. Jenner, and C. D. Marsden. 1991. Alterations in the levels of iron, ferritin and other trace metals in Parkinson's disease and other neurodegenerative diseases affecting the basal ganglia. Brain 114: 1953-1975.
11. 11. Dizdaroglu, M., G. Rao, B. Halliwell, and E. Gajewski. 1991. Damage to DNA bases in mammalian chromatin by hydrogen peroxide in the presence of ferric and cupric ions. Arch. Biochem. Biophys. 285: 317-324.
12. 12. Dizdaroglu, M. 1992. Oxidative damage to DNA in mammalian chromatin. Mutat. Res. 275: 331-342.
13. 13. Donaldson, J., F. S. LaBella, and D. Gesser. 1980. Enhanced autoxidation of dopamine as a possible basis of manganese neurotoxicity. Neurotoxicology 2: 53-64.
14. 14. Fahn, S., and G. Cohen. 1992. The oxidant stress hypothesis in Parkinson's disease: Evidence supporting it. Ann. Neurol. 32: 804-812.
15. 15. Floyd, R. A. 1990. The role of 8-hydroxyguanine in carcinogenesis. Carcinogenesis 11: 1447-1450.
16. 16. Gillette, J. R., D. Watland, and G. Kalnitsky. 1954. The catalysis of the oxidation of some hydroxybenzene derivatives by various metallic ions. Biochim. Biophys. Acta 15: 526-532.
17. 17. Gillette, J. R., D. Watland, and G. Kalnitsky. 1955. Some properties of the manganese and copper catalyzed oxidation of catechol and some other ortho-dihydroxybenzene derivatives. Biochim. Biophys. Acta 16: 51-57.
18. 18. Graham, D. G., S. M. Tiffany, W. R. Bell, Jr., and W. F. Gutknecht. 1978. Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6-hydroxydopamine and related compounds toward C1300 neuroblastoma cells in vitro. Mol. Pharmacol. 14: 644-653.
19. 19. Gurney M. E., H. Pu, A. Y. Chiu, M. C. Dal Canto, C. Y. Polchow, D. D. Alexander, J. Caliendo, A. Hentati, Y. W. Kwon, H-X. Deng, W. Chen, P. Zhai, R. L. Sufit, and T. Siddique. 1994. Motor neuron degeneration in mice that express a human Cu,Zn, Superoxide dismutase mutation. Science 264: 1772-1775.
20. 20. Halliwell, B. 1992. Reactive oxygen species and the central nervous system. J. Neurochem. 59: 1609-1623.
21. 21. Hastings, T. G. 1995. Enzymatic oxidation of dopamine: The role of prostaglandin H synthase. J. Neurochem. 64: 919-924.
22. 22. Kalyanaraman, B., and R. C. Sealy. 1982. Electron spin resonance-spin stabilization in enzymatic systems: Detection of semiquinones produced during peroxidatic oxidation of catechols and catecholamines. Biochem. Biophys. Res. Commun. 106: 1119-1225.
23. 23. Kasai, H., and S. Nishimura. 1984. Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res. 12: 2137-2145.
24. 24. Lévay, G., and W. J. Bodell. 1993. Detection of dopamine-DNA adducts: Potential role in Parkinson's disease. Carcinogenesis 14: 1241-1245.
25. 25. Li, Y., and M. A. Trush. 1993. DNA damage resulting from the oxidation of hydroquinone by copper: Role for a Cu(II)/Cu(I) redox cycle and reactive oxygen generation. Carcinogenesis 14: 1303-1311.
26. 26. Li, Y., and M. A. Trush. 1994. Reactive oxygen-dependent DNA damage resulting from the oxidation of phenolic compounds by a copper-redox cycle mechanism. Cancer Res. (Suppl.) 54: 1895s-1898s.
27. 27. Lloyd, R. V. 1995. Mechanism of the manganese-catalyzed autoxidation of dopamine. Chem. Res. Toxicol. 8: 111-116.
28. 28. Makrigiorgos, G. M., E. Bump, C. Huang, J. Baranowska-Kortylewicz, and A. I. Kassis. 1995. A fluorimetric method for the detection of copper-mediated hydroxyl free radicals in the immediate proximity of DNA. Free Radicals Biol. Med. 18: 669-678.
29. 29. Mattammal, M. B., R. Strong, V. E. White, and F-F. Hsu. 1994. Characterization of peroxidative oxidation products of dopamine by mass spectrometry. J. Chromatogr. (B) 658: 21-30.
30. 30. Mattammal, M. B., R. Strong, V. M. Lakshmi, H. D. Chung, and A. H. Stephenson. 1995. Prostaglandin H synthetase-mediated metabolism of dopamine: Implication for Parkinson's disease. J. Neurochem. 64: 1645-1654.
31. 31. Nappi, A. J., and E. Vass. 1994. The effects of glutathione and ascorbic acid on the oxidations of 6-hydroxydopa and 6-hydroxydopamine. Biochim. Biophys. Acta 1201: 498-504.
32. 32P-postlabeling of DNA reacted with p-benzoquinone. Carcinogenesis 11: 1469-1472.
33. 32P-postlabeling of DNA reacted with p-benzoquinone. Chem. Res. Toxicol. 4: 199-202.
34. 34. Prütz, W. A. 1993. Cu(II)-induced oxidation of catechols, ascorbate and o-phenylenediamine is promoted by DNA. Z. Naturforsch. 48C: 872-878.
35. 35. Rahman, A. Shahabudddin, S. M. Hadi, J. H. Parish, and K. Ainley. 1989. Strand scission in DNA induced by quercetin and Cu(II): role of Cu(I) and oxygen free radicals. Carcinogenesis 10: 1833-1839.
36. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 7: 1543-1551.
37. 37. Riederer, P., E. Sofic, W-D. Rausch, B. Schmidt, G. P. Reynolds, K. Jellinger, and M. B. H. Youdim. 1989. Transition metals, ferritin, glutathione, and ascorbic acid in Parkinsonian brains. J. Neurochem. 52: 515-520.
38. 38. Sanchez-Ramos, J. R., E. Overik, and B. N. Ames. 1994. A marker of oxyradical-mediated DNA damage (8-hydroxy-2′deoxyguanosine) is increased in nigro-striatum of Parkinson's disease brain. Neurodegeneration 3: 197-204.
39. 39. Shatkin, A. J. 1969. Colorimetric reactions for DNA, RNA and protein determinations. In Fundamental Techniques in Virology (K. Habel and N. P. Salz, Eds.), pp. 231-236. Academic Press, New York.
40. 40. Simonian, N. A., and J. T. Coyle. 1996. Oxidative stress in neurodegenerative diseases. Annu. Rev. Pharmacol. Toxicol. 36: 83-106.
41. 41. Spencer, J. P. E., A. Jenner, O. I. Aruoma, P. J. Evans, H. Kaur, D. T. Dexter, P. Jenner, A. J. Lees, D. C. Marsden, and B. Halliwell. 1994. Intense oxidative DNA damage promoted by L-DOPA and its metabolites: Implications for neurodegenerative disease. FEBS Lett. 353: 246-250.
42. 42. Yamamoto, K., and S. Kawanishi. 1989. Hydroxyl free radical is not the main active species in site-specific DNA damage induced by copper (II) and hydrogen peroxide. J. Biol. Chem. 264: 15435-15440.
43. 43. Youdim, M. B. H., D. Ben-Shachar, and P. Riederer. 1996. The possible role of iron in the etiopathology of Parkinson's disease. Movement Disorders 8: 1-12.
44. 44. Zecca, L., R. Pietra, C. Goj, C. Mecacci, D. Radice, and E. Sabbioni. 1994. Iron and other metals in neuromelanin, substantia nigra and putamen of human brain. J. Neurochem. 62: 1097-1101.