8-Chloroadenine: A novel product formed from hypochlorous acid-induced damage to calf thymus DNA

Biomarkers

Volumn 4, Issue 4, 1999, Pages 303-310

  Whiteman, Matthew ^a   Jenner, Andrew ^a   Halliwell, Barry ^a,b  

^a UNIVERSITY OF LONDON   (United Kingdom)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

8 chloroadenine; Hypochlorous acid; Inflammation; Oxidative DNA damage; Reactive chlorine species

Indexed keywords

8 CHLOROADENINE; BIOLOGICAL MARKER; DNA; HYDROGEN PEROXIDE; HYPOCHLOROUS ACID; MYELOPEROXIDASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERICIDAL ACTIVITY; CHLORINATION; CYTOTOXICITY; DIAGNOSTIC VALUE; DNA DAMAGE; DNA DRUG COMPLEX; GAS CHROMATOGRAPHY; INFLAMMATION; PROTEIN MODIFICATION;

EID: 0032856568     PISSN: 1354750X     EISSN: None     Source Type: Journal    
DOI: 10.1080/135475099230831     Document Type: Article

References (28)

1. ALBRICH, J. M., MCCARTHY, C. A. and HURST, J. K. 1981, Biological reactivity of hypochlorous acid: implications for microbicidal mechanisms of leukocytic myeloperoxidase. Procedings of the National Academy of Sciences USA, 78, 210-214.
2. ARUOMA, O. I., HALLIWELL, B., HOEY, B. M. and BUTLER, J. 1989, The antioxidant action of N-acetylcysteine - its reaction with hydrogen peroxide, hydroxyl radical, Superoxide and hypochlorous acid. Free Radicals in Biology and Medicine, 6, 593-597.
3. BARETTE, W. C., HANNUM, D. M., WHEELER, W. D. and HURST, J. K. 1989, General mechanism for the bacterial toxicity of hypochlorous acid: abolition of ATP production. Biochemistry, 28, 9172-9178.
4. BLAKE, D. R., MERRY, P., UNSWORTH, J., KIDD, B. L., OUTHWAITE, J. M., BALLARD, R., MORRIS, C. J., GRAY, L. and LUNEC, J. 1989, Hypoxia-reperfusion injury in the inflamed human joint. Lancet, i, 289-293.
5. CARR, A., VANDERBERG, J. J. M. and WINTERBOURN, C. 1996, Chlorination of cholesterol in cell membranes by hypochlorous acid. Archives of Biochemistry and Biophysics, 332, 63-69.
6. FOLKES, L. K., CANDEIAS, L. P. and WARDMAN, P. 1995, Kinetics and mechanisms of hypochlorous acid reactions. Archives of Biochemistry and Biophysics, 323, 120-126.
7. FOOTE, C. S., GOYNE, T. E. and LEHRER, R. I. 1983, Assessment of chlorination by human neutrophils. Nature (London), 301, 715-716.
8. GOULD, J. P., RICHARDS, J. T. and MILES, M. G. 1984a, The kinetics and primary products of uracil chlorination. Water Research, 18, 205-212.
9. GOULD, J. P., RICHARDS, J. T. and MILES, M. G. 1984b, The formation of stable organic chloramines during the aqueous chlorination of cytosine and 5-methylcytosine. Water Research, 18, 991-999.
10. HALLIWELL, B. 1995, Oxygen radicals, nitric oxide and human inflammatory joint disease. Annals of Rheumatic Disorders, 54, 505-510.
11. HALLIWELL, B., WASIL, M. and GROOTVELD, M. 1987, Biologically-significant scavenging of the myeloperoxidase-derived oxidant hypochlorous acid by ascorbic acid. Implications for antioxidant protection in the inflamed joint. FEBS Letters, 213, 15-18.
12. HAZEN, S.L. and HEINICKE, J. W. 1997, 3-chlorotyrosine, a specific marker for myeloperoxidase catalysed oxidation, is markedly elevated in human atherosclerotic tissue. Journal of Clinical Investigation, 99, 2075-2081.
13. HAZEN, S. L., Hsu, F. F., MUELLER, D. M., CROWLEY, J. R. and HEINICKE, J. W. 1996, Human neutrophils employ chlorine gas as an oxidant during phagocytosis. Journal of Clinical Investigation, 98, 1283-1289.
14. HOYANO, Y., BACON., V., SUMMONS, R. E., PEREIRA, B., HALPERN, B. and DUFFIELD, A. M. 1973, Chlorination studies IV: The reaction of aqueous hypochlorous acid with pyrimidine and purine bases. Biochemical and Biophysical Research Communications, 53, 1195-1199.
15. ITOH, N., YOSHIKAZU, I. and YAMADA, H. 1987, Haloperoxidase-catalyzed halogenation of nitrogen containing aromatic heterocyclics represented by nucleic bases. Biochemistry, 26, 282-289.
16. KALYANARAMAN, B. and SOHLE, P. C. 1985, Generation of free radicals from foreign compounds by neutrophil-derived oxidants. Journal of Clinical Investigation, 75,1618-1622.
17. KOPPENOL, W. H. 1994, Thermodynamic considerations on the formation of reactive species from hypochlorite, Superoxide and nitrogen monoxide - could nitrosyl chloride be produced by neutrophils and macrophages. FEBS Letters, 347, 5-8.
18. MORRIS, J. C. 1966, The acid ionization constant of hypochlorous acid from 5 to 35 degrees. Journal of Physical Chemistry, 70, 3798-3805.
19. PATTON, W., BACON, V., DUFFIELD, A. M., HALPERN, B., HOYANO, Y., PEREIRA, W. and LEDERBERG, J. 1972, Chlorination studies I: The reaction of aqueous hypochlorous acid with cytosine. Biochemical and Biophysical Research Communications, 48, 880-884.
20. PERO, R. W., SHENG, Y., OLSSON, A., BRYNGELSSON, C. and LUND-PERO, M. 1996, Hypochlorous acid/N-chloramines are naturally produced DNA repair inhibitors. Carcinogenesis, 17, 13-18.
21. PRUTZ, W. A. 1996, Hypochlorous acid interactions with thiols, nucleotides, DNA and other biological substrates. Archives of Biochemistry and Biophysics, 332, 110-120.
22. SCHRAUFSTATTER, I. U., BROWNE, K., HARRIS, A., HYSLOP, P. A., JACKSON, J. H, QUEHENBERGER, O. and COCHRANE, C. G. 1990, Mechanisms of hypochlorite injury of target cells. Journal of Clinical Investigation, 85, 554-562.
23. SPENCER, J. P. E., JENNER, A., ARUOMA, O. I., EVANS, P. J., KAUR, H., DEXTER, D. T., JENNER, P., LEES, A. J., MARSDEN, D. C. and HALLIWELL, B. 1994, Intense oxidative DNA damage promoted by L-DOPA and its metabolites. Implications for neurodegenerative disease. FEBS Letters, 353, 246-250.
24. VAN RENSBERG, C. E. J., VAN STADEN, A. M. and ANDERSON, R. 1991, Inactivation of poly(ADP-ribose) polymerase by hypochlorous acid. Free Radicals in Biology and Medicine, 1, 285-291.
25. VAN RENSBERG, C. E. J., VAN STADEN, A. M., ANDERSON, R. and VAN RENSBERG, E. J. 1992, Hypochlorous acid potentiates hydrogen peroxide-mediated DNA-strand breaks in human mononuclear leucocytes. Mutation Research, 265, 255-261.
26. WEISS, S. J., KLEIN, P., SLIVKA, A. and WEISS, M. 1992, Chlorination of taurine by human neutrophils. Evidence for hypochlorous acid generation. Journal of Clinical Investigation, 70, 1341-1349.
27. WHITEMAN, M., JENNER, A. and HALLIWELL, B. 1997, Hypochlorous acid-induced base modifications in isolated calf thymus DNA. Chemical Research in Toxicology, 10, 1240-1246.
28. WlNTERBOURN, C. C. 1985, Comparative reactivities of various biological compounds with myeloperoxidase-hydrogen peroxide-chloride, and similarity of the oxidant hypochlorite. Biochemica et Biophysica Acta, 840, 204-210.