Induction of DNA strand breakage and base oxidation by nitroxyl anion through hydroxyl radical production

Free Radical Biology and Medicine

Volumn 26, Issue 9-10, 1999, Pages 1305-1313

  Ohshima, Hiroshi ^a   Gilibert, Isabelle ^a   Bianchini, Franca ^a  

^a INTERNATIONAL AGENCY FOR RESEARCH ON CANCER   (France)

Author keywords

8 Oxo 2' deoxyguanosine; Angeli's salt; Free radicals; Hydroxyl radical; Malondialdehyde; Nitric oxide; Nitroxyl; Peroxynitrite; Strand breakage

Indexed keywords

ANTIOXIDANT; CATALASE; CHELATING AGENT; SCAVENGER; SUPEROXIDE DISMUTASE;

ARTICLE; CONTROLLED STUDY; DEGENERATIVE DISEASE; DNA DETERMINATION; DNA STRAND BREAKAGE; INFLAMMATION; OXIDATION; PRIORITY JOURNAL; SCAVENGING SYSTEM;

ANIMALS; ANTIOXIDANTS; CATALASE; CATTLE; CHELATING AGENTS; DEOXYRIBOSE; DNA; DNA DAMAGE; FREE RADICAL SCAVENGERS; FREE RADICALS; HYDROXYL RADICAL; MALONDIALDEHYDE; NITRIC OXIDE; NITRIC OXIDE DONORS; NITROGEN OXIDES; OXIDATION-REDUCTION; PLASMIDS; SUPEROXIDE DISMUTASE; THIOBARBITURIC ACID REACTIVE SUBSTANCES;

LETHRINIDAE;

EID: 0032984822     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(98)00327-X     Document Type: Article

References (33)

1. Wink D.A., Feelisch M., Fukuto J., Chistodoulou D., Jourd'heuil D., Grisham M.B., Vodovotz Y., Cook J.A., Krishna M., DeGraff W.G., Kim S., Gamson J., Mitchell J.B. The cytotoxicity of nitroxyl possible implications for the pathophysiological role of NO . Arch. Biochem. Biophys. 351:1998;66-74.
2. Fukuto J.M., Hobbs A.J., Ignarro L.J. Conversion of nitroxyl (HNO) to nitric oxide (NO) in biological systems the role of physiological oxidants and relevance to the biological activity of HNO . Biochem. Biophys. Res. Commun. 196:1993;707-713.
3. VanUffelen B.E., Van der Zee J., de Koster B.M., VanSteveninck J., Elferink J.G.R. Intracellular but not extracellular conversion of nitroxyl anion into nitric oxide leads to stimulation of human neutrophil migration. Biochem. J. 330:1998;719-722.
4. Wink D.A., Feelisch M. Formation and detection of nitroxyl and nitrous oxide, In Feelisch, M . Stamler J. Methods in nitric oxide research. 1996;403-412 Wiley, New York.
5. Stamler J.S., Singel D.J., Loscalzo J. Biochemistry of nitric oxide and its redox-activated forms. Science. 258:1992;1898-1902.
6. Koppenol W.H. Thermodynamics of reactions involving nitrogen-oxygen compounds. Methods Enzymol. 268:1996;7-12.
7. Hobbs A.J., Fukuto J.M., Ignarro L.J. Formation of free nitric oxide from L-arginine by nitric oxide synthase direct enhancement of generation by superoxide dismutase . Proc. Natl Acad. Sci. USA. 91:1994;10992-10996.
8. Schmidt H.H., Hofmann H., Schindler U., Shutenko Z.S., Cunningham D.D., Feelisch M. No ·NO from NO synthase. Proc. Natl Acad. Sci. USA. 93:1996;14492-14497.
9. Arnelle D.R., Stamler J.S. NO+, NO, and NO- donation by S-nitrosothiols implications for regulation of physiological functions by S-nitrosylation and acceleration of disulfide formation . Arch. Biochem. Biophys. 318:1995;279-285.
10. Hogg N., Singh R.J., Kalyanaraman B. The role of glutathione in the transport and catabolism of nitric oxide. FEBS Lett. 382:1996;223-228.
11. Wong P.S.Y., Hyun J., Fukuto J.M., Shirota F.N., DeMaster E.G., Shoeman D.W., Nagasawa H.T. Reaction between S-nitrosothiols and thiols generation of nitroxyl (HNO) and subsequent chemistry . Biochemistry. 37:1998;5362-5371.
12. Gow A.J., Stamler J.S. Reactions between nitric oxide and haemoglobin under physiological conditions. Nature. 391:1998;169-173.
13. Sharpe M.A., Cooper C.E. Reactions of nitric oxide with mitochondrial cytochrome c a novel mechanism for the formation of nitroxyl anion and peroxynitrite . Biochem. J. 332:1998;9-19.
14. Ohshima, H.; Yoshie, Y.; Auriol, S.; Gilibert, I. Anti-oxidant and pro-oxidant actions of flavonoids: effects on DNA damage induced by nitric oxide, peroxynitrite and nitroxyl anion. Free Radic. Biol. Med.25, 1057-1065; 1998.
15. 15NO that trioxodinitrate(II) decomposes into nitrosyl hydride and nitrite in neutral aqueous solution. Inorg. Chem. 24:1985;4285-4288.
16. Fukuto J.M., Hszieh R., Gulati P., Chiang K.T., Nagasawa H.T. N,O-diacylated-N-hydroxyarylsulfonamides: nitroxyl precursors with potent smooth muscle relaxant properties. Biochem. Biophys. Res. Commun. 187:1992;1367-1373.
17. Zamora R., Grzesiok A., Weber H., Feelisch M. Oxidative release of nitric oxide accounts for guanylyl cyclase stimulating, vasodilator and anti-platelet activity of Piloty's acid a comparison with Angeli's salt . Biochem. J. 312:1995;333-339.
18. Yoshie Y., Ohshima H. Nitric oxide synergistically enhances DNA strand breakage induced by polyhydroxyaromatic compounds, but inhibits that induced by the Fenton-reaction. Arch. Biochem. Biophys. 342:1997;13-21.
19. Yoshie Y., Ohshima H. Synergistic induction of DNA strand breakage by catechol-estrogen and nitric oxide implications for hormonal carcinogenesis . Free Radic. Biol. Med. 24:1998;341-348.
20. Yoshie Y., Ohshima H. Synergistic induction of DNA strand breakage caused by nitric oxide together with catecholamine implications for neurodegenerative disease . Chem. Res. Toxicol. 10:1997;1015-1022.
21. Epe B., Hegler J. Oxidative DNA damage: endonuclease fingerprinting. Methods Enzymol. 234:1994;122-131.
22. Epe B., Ballmaier D., Roussyn I., Briviba K., Sies H. DNA damage by peroxynitrite characterized with DNA repair enzymes. Nucleic Acids Res. 24:1996;4105-4110.
23. Hogg N., Darley Usmar V.M., Wilson M.T., Moncada S. Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide. Biochem. J. 281:1992;419-424.
24. Draper H.H., Squires E.J., Mahmoodi H., Wu J., Agarwal S., Hadley M.A. Comparative evaluation of thiobarbituric acid methods for the determination of malondialdehyde in biological materials. Free Radic. Biol. Med. 15:1993;353-363.
25. Yamaguchi R., Hirano T., Asami S., Chung M.H., Sugita A., Kasai H. Increased 8-hydroxyguanine levels in DNA and its repair activity in rat kidney after administration of a renal carcinogen, ferric nitrilotriacetate. Carcinogenesis. 17:1996;2419-2422.
26. Murphy M.E., Sies H. Reversible conversion of nitroxyl anion to nitric oxide by superoxide dismutase. Proc. Natl Acad. Sci. USA. 88:1991;10860-10864.
27. Huie R.E., Padmaja S. The reaction of NO with superoxide. Free Radic. Res. Commun. 18:1993;195-199.
28. Seddon W.A., Fletcher J.W., Sopchyshyn F.C. Pulse radiolysis of nitric oxide in aqueous solution. Can. J. Chem. 51:1998;1123-1130.
29. 2 to form peroxonitrite . Inorg. Chem. 25:1986;2676-2677.
30. Szabo C., Ohshima H. DNA damage induced by peroxynitrite subsequent biological effects . Nitric Oxide Biol. Chem. 1:1997;373-385.
31. Salgo M.G., Stone K., Squadrito G.L., Battista J.R., Pryor W.A. Peroxynitrite causes DNA nicks in plasmid pBR322. Biochem. Biophys. Res. Commun. 210:1995;1025-1030.
32. Di Mascio P., Bechara E.J., Medeiros M.H., Briviba K., Sies H. Singlet molecular oxygen production in the reaction of peroxynitrite with hydrogen peroxide. FEBS Lett. 355:1994;287-289.
33. Devasagayam T.P., Steenken S., Obendorf M.S., Schulz W.A., Sies H. Formation of 8-hydroxy(deoxy)guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen. Biochemistry. 30:1991;6283-6289.