Radicals derived from histone hydroperoxides damage nucleobases in RNA and DNA

Chemical Research in Toxicology

Volumn 13, Issue 7, 2000, Pages 665-672

  Luxford, Catherine ^a   Dean, Roger T ^a   Davies, Michael J ^a  

^a HEART RESEARCH INSTITUTE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

HISTONE; HYDROXYL RADICAL; NUCLEIC ACID BASE;

ARTICLE; CROSS LINKING; DNA DAMAGE; ELECTRON SPIN RESONANCE; GAMMA RADIATION; MUTAGENESIS; OXIDATIVE STRESS; PROTEIN DEGRADATION; RADIATION DOSE; RADIATION EXPOSURE;

ANIMALS; CATTLE; DEOXYGUANOSINE; DNA; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, RADIATION; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HISTONES; NUCLEIC ACIDS; OXIDATION-REDUCTION; PEROXIDES;

EID: 0033928033     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx000053u     Document Type: Article

References (51)

1. von Sonntag, C. (1987) The chemical basis of radiation biology, pp 1-515, Taylor and Francis, London.
2. Davies, M. J., and Dean, R. T. (1997) Radical-mediated protein oxidation: from chemistry to medicine, pp 1-443, Oxford University Press, Oxford.
3. Halliwell, B., and Gutteridge, J. M. C. (1999) Free Radicals in Biology and Medicine, 3rd ed., pp 1-936, Oxford University Press, Oxford.
4. Dean, R. T., Fu, S., Stocker, R., and Davies, M. J. (1997) The biochemistry and pathology of radical-mediated protein oxidation. Biochem. J. 324, 1-18.
5. Davies, M. J., Fu, S., Wang, H., and Dean, R. T. (1999) Stable markers of oxidant damage to proteins and their application in the study of human disease. Free Radical Biol. Med. 27, 1151-1163.
6. Sohal, R. S., and Weindruch, R. (1996) Oxidative stress, caloric restriction, and aging. Science 273, 59-63.
7. Stadtman, E. R., and Berlett, B. S. (1998) Reactive oxygen-mediated protein oxidation in aging and disease. Drug Metab. Rev. 30, 225-243.
8. Simpson, J. A., Narita, S., Gieseg, S., Gebicki, S., Gebicki, J. M., and Dean, R. T. (1992) Long-lived reactive species on free-radical-damaged proteins. Biochem. J. 282, 621-624.
9. Gieseg, S. P., Simpson, J. A., Charlton, T. S., Duncan, M. W., and Dean, R. T. (1993) Protein-bound 3,4-dihydroxyphenylalanine is a major reductant formed during hydroxyl radical damage to proteins. Biochemistry 32, 4780-4786.
10. Gebicki, S., and Gebicki, J. M. (1993) Formation of peroxides in amino acids and proteins exposed to oxygen free radicals. Biochem. J. 289, 743-749.
11. Morin, B., Davies, M. J., and Dean, R. T. (1998) The protein oxidation product 3,4-dihydroxyphenylalanine (DOPA) mediates oxidative DNA damage. Biochem. J. 330, 1059-1067.
12. Gebicki, J. M. (1997) Protein hydroperoxides as new reactive oxygen species. Redox Rep. 3, 99-110.
13. Luxford, C., Morin, B., Dean, R. T., and Davies, M. J. (1999) Histone H1- and other protein- and amino acid-hydroperoxides can give rise to free radicals which oxidise DNA. Biochem. J. 344, 125-134.
14. Davies, M. J., Fu, S., and Dean, R. T. (1995) Protein hydroperoxides can give rise to reactive free radicals. Biochem. J. 305, 643-649.
15. Davies, M. J. (1996) Protein and peptide alkoxyl radicals can give rise to C-terminal decarboxylation and backbone cleavage. Arch. Biochem. Biophys. 336, 163-172.
16. Neuzil, J., Gebicki, J. M., and Stocker, R. (1993) Radical-induced chain oxidation of proteins and its inhibition by chain-breaking antioxidants. Biochem. J. 293, 601-606.
17. Fu, S., Gebicki, S., Jessup, W., Gebicki, J. M., and Dean, R. T. (1995) Biological fate of amino acid, peptide and protein hydroperoxides. Biochem. J. 311, 821-827.
18. Gebicki, S., Dean, R. T., and Gebicki, J. M. (1996) in Oxidative Stress and Redox Regulation: Cellular Signaling, AIDS, Cancer and Other Diseases, p 139, Institute Pasteur, Paris.
19. Gebicki, S., and Gebicki, J. M. (1999) Crosslinking of DNA and proteins induced by protein hydroperoxides. Biochem. J. 338, 629-636.
20. Robinson, M. G., Weiss, J. J., and Wheeler, C. M. (1966) Irradiation of deoxyribonucleohistone solutions. I. Amino acid destruction. Biochim. Biophys. Acta 124, 176-180.
21. Robinson, M. G., Weiss, J. J., and Wheeler, C. M. (1966) Irradiation of deoxyribonucleohistone solutions. II. Labilization of the DNA-histone linkage. Biochim. Biophys. Acta 124, 181-186.
22. Mee, L. K., and Adelstein, S. J. (1981) Predominance of core histones in formation of DNA-protein crosslinks in γ-irradiated chromatin. Proc. Natl. Acad. Sci. U.S.A. 78, 2194-2198.
23. Elia, M. C., and Bradley, M. O. (1992) Influence of chromatin structure on the induction of DNA double strand breaks by ionizing radiation. Cancer Res. 52, 1580-1586.
24. Xue, L. Y., Friedman, L. R., Oleinick, N. L., and Chiu, S. M. (1994) Induction of DNA damage in γ-irradiated nuclei stripped of nuclear protein classes: differential modulation of double-strand break and DNA-protein crosslink formation. Int. J. Radiat. Biol. 66, 11-21.
25. Dijkwel, P. A., and Wenink, P. W. (1986) Structural integrity of the nuclear matrix: differential effects of thiol agents and metal chelators. J. Cell Sci. 84, 53-67.
26. Jessup, W., Dean, R. T., and Gebicki, J. M. (1994) Iodometric determination of hydroperoxides in lipids and proteins. Methods Enzymol. 233, 289-303.
27. Wolff, S. P. (1994) Ferrous ion oxidation in the presence of ferric ion indicator xylenol orange for measurement of hydroperoxides. Methods Enzymol. 233, 182-189.
28. Gay, C., Collins, J., and Gebicki, J. M. (1999) Hydroperoxide assay with the ferric-xylenol orange complex. Anal. Biochem. 273, 149-155.
29. Duling, D. R. (1994) Simulation of multiple isotropic spin trap EPR spectra. J. Magn. Reson. 104B, 105-110.
30. I) and monoperoxyphthalic acid and its anion. J. Chem. Soc., Perkin Trans. 2, 629-634.
31. Hanna, P. M., Chamulitrat, W., and Mason, R. P. (1992) When are metal ion-dependent hydroxyl and alkoxyl radical adducts of 5,5-dimethyl-1-pyrroline N-oxide artifacts? Arch. Biochem. Biophys. 296, 640-644.
32. Hazlewood, C., and Davies, M. J. (1995) EPR spin trapping studies of the reaction of radicals derived from hydroperoxide tumour-promoters with nucleic acids and their components. J. Chem. Soc., Perkin Trans. 2, 895-901.
33. Ho, W. F., Gilbert, B. C., and Davies, M. J. (1997) EPR spin trapping studies of the reaction of the hydroxyl and other electrophilic radicals with uridine and related compounds. Isotopic substitution to refine analyses and aid quantification. J. Chem. Soc., Perkin Trans. 2, 2533-2538.
34. DeLange, R. J., and Smith, E. L. (1972) The structure of histones. Ace. Chem. Res. 5, 368-373.
35. Wolffe, A. (1992) Chromatin: Structure and Function, Academic Press, London.
36. Morin, B., Bubb, W. A., Davies, M. J., Dean, R. T., and Fu, S. (1998) 3-Hydroxylysine, a potential marker for studying radical-induced protein oxidation. Chem. Res. Toxicol. 11, 1265-1273.
37. Dizdaroglu, M., and Gajewski, E. (1989) Structure and mechanism of hydroxyl radical-induced formation of a DNA-protein cross-link involving thymine and lysine in nucleohistone. Cancer Res. 49, 3463-3467.
38. Mandel, R., Kolomijtseva, G., and Brahms, J. G. (1979) DNA-protein interactions in nucleosomes and in chromatin. Structural studies of chromatin stabilized by ultraviolet-light induced crosslinking. Eur. J. Biochem. 96, 257-265.
39. Saito, I., Sugiyama, H., and Matsuura, T. (1982) Mechanism of DNA-histone crosslinks in UV-irradiated nuclei. Nucleic Acids Symp. Ser. 11, 225-228.
40. Cadet, J., D'Ham, C., Douki, T., Pouget, J. P., Ravanat, J. L., and Sauvaigo, S. (1998) Facts and artifacts in the measurement of oxidative base damage to DNA. Free Radical Res. 29, 541-550.
41. Augusto, O., Netto, L. E., and Gomes, L. F. (1992) DNA alkylation by carbon-centered radicals. Braz. J. Med. Biol. Res. 25, 1171-1183.
42. Augusto, O. (1993) Alkylation and cleavage of DNA by carbon-centered radical metabolites. Free Radical Biol. Med. 15, 329-336.
43. Harkin, L. A., Butler, L. M., and Burcham, P. C. (1997) Role of G → T transversions in the mutagenicity of alkylperoxyl radicals: induction of alkali-labile sites in bacteriophage M13mp19. Chem. Res. Toxicol. 10, 575-581.
44. Valentine, M. R., Rodriguez, H., and Termini, J. (1998) Mutagenesis by peroxyl radical is dominated by transversions at deoxy-guanosine: evidence for the lack of involvement of 8-oxo-dG and/ or abasic site formation. Biochemistry 37, 7030-7038.
45. Kawanishi, S., Oikawa, S., Murata, M., Tsukitome, H., and Saito, I. (1999) Site-specific oxidation at GG and GGG sequences in double-stranded DNA by benzoyl peroxide as a tumour promoter. Biochemistry 38, 16733-16739.
46. Steenken, S., and Jovanovic, S. V. (1997) How easily oxidizable is DNA: one-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J. Am. Chem. Soc. 119, 617-618.
47. Luger, K., Mader, A. W., Richmond, R. K., Sargent, D. F., and Richmond, T. J. (1997) Crystal structure of the nucleosome core particle at 2.8 A resolution. Nature 389, 251-260.
48. Symons, M. C. R. (1997) Electron movement through proteins and DNA. Free Radical Biol. Med. 22, 1271-1276.
49. Lebkowski, J. S., and Laemmli, U. K. (1982) Non-histone proteins and long-range organization of HeLa interphase DNA. J. Mol. Biol. 156, 325-344.
50. Chiu, S. M., Xue, L. Y., Friedman, L. R., and Oleinick, N. L. (1993) Copper ion-mediated sensitization of nuclear matrix attachment sites to ionizing radiation. Biochemistry 32, 6214-6219.
51. Chiu, S., Xue, L., Friedman, L. R., and Oleinick, N. L. (1995) Differential dependence on chromatin structure for copper and iron ion induction of DNA double-strand breaks. Biochemistry 34, 2653-2661.