Quinone-enhanced reduction of nitric oxide by xanthine/xanthine oxidase

Chemical Research in Toxicology

Volumn 22, Issue 5, 2009, Pages 818-823

  Sanchez Cruz, Pedro ^a   Alegría, Antonio E ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; NITRIC OXIDE; PHOSPHATE; QUINONE DERIVATIVE; XANTHINE; XANTHINE OXIDASE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION REDUCTION REACTION; PH; SYNTHESIS;

KINETICS; NITRIC OXIDE; NITROUS OXIDE; OXIDATION-REDUCTION; PHENANTHRENES; QUINONES; XANTHINE OXIDASE;

EID: 67649989667     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx800392j     Document Type: Article

References (54)

1. Boyle, R. G., and Travers, S. (2006) Hypoxia: targeting the tumour. Anticancer Agents Med. Chem. 6, 281-286.
2. O'Brien, P. J. (1991) Molecular mechanisms of quinone cytotoxicity. Chem.-Biol. Interact. 80, 1-41.
3. Tudor, G., Gutierrez, P., Aguilera-Gutierrez, A., and Sausville, E. A. (2003) Cytotoxicity and apoptosis of benzoquinones: Redox cycling, cytochrome c release, and BAD protein expression. Biochem. Pharmacol. 65, 1061-1075.
4. Tani, N., Yabuki, M., Komuro, S., and Kanamaru, H. (2001) Characterization of the enzymes involved in the in vitro metabolism of amrubicin hydrochloride. Free Radical Res. 35, 145-158.
5. Iyanagi, T., and Yamazaki, I. (1970) One-electron reduction in biochemical systems. V. Difference in the mechanism of quinone reduction by NADH dehydrogenase and the NAD(P)H dehydrogenase (DT-diaphorase). Biochim. Biophys. Acta 216, 282-294.
6. Alegria, A. E., and Santiago, G. (1997) Adriamycin and daunomycin semiquinone membrane/buffer partition constants using the spin-broadening technique. Arch. Biochem. Biophys. 346, 91-95.
7. Schreiber, J., Mottley, C., Sinha, B. K., Kalyanaraman, B., and Mason, R. P. (1987) One-electron reduction of daunomycin, daunomycinone and 7-deoxydaunomycinone by xanthine/xanthine oxidase system: Detection of semiquinone free radicals by electron spin resonance. J. Am. Chem. Soc. 109, 348-351.
8. Roginsky, V. A., Barsukova, T. K., and Stegmann, H. B. (1999) Kinetics of redox interaction between substituted quinones and ascorbate under aerobic conditions. Chem.-Biol. Interact. 121, 177-197.
9. Dessy, C., Moniotte, S., Ghisdal, P., Havaux, X., Noirhomme, P., and Balligand, J. L. (2004) Endothelial beta3-adrenoceptors mediate vasorelaxation of human coronary microarteries through nitric oxide and endothelium-dependent hyperpolarization. Circulation 110, 948-954.
10. Gomes, M. Z., Raisman-Vozari, R., and Del Bel, E. A. (2008) A nitric oxide synthase inhibitor decreases 6-hydroxydopamine effects on tyrosine hydroxylase and neuronal nitric oxide synthase in the rat nigrostriatal pathway. Brain Res. 1203, 160-169.
11. Lancaster, J. R., Jr. (1994) Simulation of the diffusion and reaction of endogenously produced nitric oxide. Proc. Natl. Acad. Sci. U.S.A. 91, 8137-8141.
12. Paolocci, N., Jackson, M. I., Lopez, B. E., Miranda, K., Tocchetti, C. G., Wink, D. A., Hobbs, A. J., and Fukuto, J. M. (2007) The pharmacology of nitroxyl (HNO) and its therapeutic potential: Not just the Janus face of NO. Pharmacol. Ther. 113, 442-458.
13. Bartberger, M. D., Liu, W., Ford, E., Miranda, K. M., Switzer, C., Fukuto, J. M., Farmer, P. J., Wink, D. A., and Houk, K. N. (2002) The reduction potential of nitric oxide (NO) and its importance to NO biochemistry. Proc. Natl. Acad. Sci. U.S.A. 99, 10958-10963.
14. Shafirovich, V., and Lymar, S. V. (2002) Nitroxyl and its anion in aqueous solutions: spin states, protic equilibria, and reactivities toward oxygen and nitric oxide. Proc. Natl. Acad. Sci. U.S.A. 99, 7340-7345.
15. Ma, X. L., Gao, F., Liu, G. L., Lopez, B. L., Christopher, T. A., Fukuto, J. M., Wink, D. A., and Feelisch, M. (1999) Opposite effects of nitric oxide and nitroxyl on postischemic myocardial injury. Proc. Natl. Acad. Sci. U.S.A. 96, 14617-14622.
16. Pagliaro, P., Mancardi, D., Rastaldo, R., Penna, C., Gattullo, D., Miranda, K. M., Feelisch, M., Wink, D. A., Kass, D. A., and Paolocci, N. (2003) Nitroxyl affords thiol-sensitive myocardial protective effects akin to early preconditioning. Free Radical Biol. Med. 34, 33-43.
17. Norris, A. J., Sartippour, M. R., Lu, M., Park, T., Rao, J. Y., Jackson, M. I., Fukuto, J. M., and Brooks, M. N. (2008) Nitroxyl inhibits breast tumor growth and angiogenesis. Int. J. Cancer 122, 1905-1910.
18. Fukuto, J. M., Jackson, M. I., Kaludercic, N., and Paolocci, N. (2008) Examining nitroxyl in biological systems. Methods Enzymol. 440, 411-431.
19. Alegria, A. E., Sanchez, S., and Quintana, I. (2004) Quinone-enhanced ascorbate reduction of nitric oxide: Role of quinone redox potential. Free Radical Res. 38, 1107-1112.
20. Clarkson, R. B., Norby, S. W., Smirnov, A., Boyer, S., Vahidi, N., Nims, R. W., and Wink, D. A. (1995) Direct measurement of the accumulation and mitochondrial conversion of nitric oxide within Chinese hamster ovary cells using an intracellular electron paramagnetic resonance technique. Biochim. Biophys. Acta 1243, 496-502.
21. Zhao, X. J., Sampath, V., and Caughey, W. S. (1995) Cytochrome c oxidase catalysis of the reduction of nitric oxide to nitrous oxide. Biochem. Biophys. Res. Commun. 212, 1054-1060.
22. Sharpe, M. A., and Cooper, C. E. (1998) Reactions of nitric oxide with mitochondrial cytochrome c: A novel mechanism for the formation of nitroxyl anion and peroxynitrite. Biochem. J. 332 (Part 1), 9-19.
23. Poderoso, J. J., Carreras, M. C., Schopfer, F., Lisdero, C. L., Riobo, N. A., Giulivi, C., Boveris, A. D., Boveris, A., and Cadenas, E. (1999) The reaction of nitric oxide with ubiquinol: Kinetic properties and biological significance. Free Radical Biol. Med. 26, 925-935.
24. Niketic, V., Stojanovic, S., Nikolic, A., Spasic, M., and Michelson, A. M. (1999) Exposure of Mn and FeSODs, but not Cu/ZnSOD, to NO leads to nitrosonium and nitroxyl ions generation which cause enzyme modification and inactivation: An in vitro study. Free Radical Biol. Med. 27, 992-996.
25. Saleem, M., and Ohshima, H. (2004) Xanthine oxidase converts nitric oxide to nitroxyl that inactivates the enzyme. Biochem. Biophys. Res. Commun. 315, 455-462.
26. Ohshima, H., Gilibert, I., and Bianchini, F. (1999) Induction of DNA strand breakage and base oxidation by nitroxyl anion through hydroxyl radical production. Free Radical Biol. Med. 26, 1305-1313.
27. Osman, A. M., and van Noort, P. C. (2003) Evidence for redox cycling of lawsone (2-hydroxy-1,4-naphthoquinone) in the presence of the hypoxanthine/xanthine oxidase system. J. Appl. Toxicol. 23, 209-212.
28. Alegria, A. E., Cordones, E., Santiago, G., Marcano, Y., Sanchez, S., Gordaliza, M., and Martin-Martin, M. L. (2002) Reductive activation of terpenylnaphthoquinones. Toxicology 175, 167-175.
29. Monteiro, H. P., Vile, G. F., and Winterbourn, C. C. (1989) Release of iron from ferritin by semiquinone, anthracycline, bipyridyl, and nitroaromatic radicals. Free Radical Biol. Med. 6, 587-591.
30. Serrano, J., Encinas, J. M., Fernandez, A. P., Rodrigo, J., and Martinez, A. (2006) Effects of acute hypobaric hypoxia on the nitric oxide system of the rat cerebral cortex: Protective role of nitric oxide inhibitors. Neuroscience 142, 799-808.
31. Yamamoto, Y., Henrich, M., Snipes, R. L., and Kummer, W. (2003) Altered production of nitric oxide and reactive oxygen species in rat nodose ganglion neurons during acute hypoxia. Brain Res. 961, 1-9.
32. White, C. R., Darley-Usmar, V., Berrington, W. R., McAdams, M., Gore, J. Z., Thompson, J. A., Parks, D. A., Tarpey, M. M., and Freeman, B. A. (1996) Circulating plasma xanthine oxidase contributes to vascular dysfunction in hypercholesterolemic rabbits. Proc. Natl. Acad. Sci. U.S.A. 93, 8745-8749.
33. Chekulayeva, L., Shevchuk, I., Chekulayev, V., and Oginskaya, E. (2007) Influence of heating on the activity of xanthine oxidase in tumor cells subjected to the phototoxic action of hematoporphyrin derivative. Neoplasma 54, 229-234.
34. Pritsos, C. A. (2000) Cellular distribution, metabolism and regulation of the xanthine oxidoreductase enzyme system. Chem.-Biol. Interact. 129, 195-208.
35. Buettner, G. R. (1988) In the absence of catalytic metals ascorbate does not autoxidize at pH 7: Ascorbate as a test for catalytic metals. J. Biochem. Biophys. Methods 16, 27-40.
36. Bensetiti, Z., Iliuta, I., Larachi, F., and Grandjean, B. P. A. (1999) Solubility of nitrous oxide in amine solutions. Ind. Eng. Chem. Res. 38, 328-332.
37. Sawyer, D. T. and Roberts, J. L. (1974) Experimental Electrochemistry for Chemists, Wiley and Sons, New York.
38. Li, H., Samouilov, A., Liu, X., and Zweier, J. L. (2004) Characterization of the effects of oxygen on xanthine oxidase-mediated nitric oxide formation. J. Biol. Chem. 279, 16939-16946.
39. Singh, R. J., Hogg, N., Joseph, J., and Kalyanaraman, B. (1995) Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane. Possible use for site-directed nitric oxide production. FEBS Lett. 360, 47-51.
40. Yoo, J., and Fukuto, J. M. (1995) Oxidation of N-hydroxyguanidine by nitric oxide and the possible generation of vasoactive species. Biochem. Pharmacol. 50, 1995-2000.
41. Nagasawa, H. T., Kawle, S. P., Elberling, J. A., DeMaster, E. G., and Fukuto, J. M. (1995) Prodrugs of nitroxyl as potential aldehyde dehydrogenase inhibitors vis-a-vis vascular smooth muscle relaxants. J. Med. Chem. 38, 1865-1871.
42. Turk, T., and Hollocher, T. C. (1992) Oxidation of dithiothreitol during turnover of nitric oxide reductase: Evidence for generation of nitroxyl with the enzyme from Paracoccus denitrificans. Biochem. Biophys. Res. Commun. 183, 983-988.
43. Fukuto, J. M., Wallace, G. C., Hszieh, R., and Chaudhuri, G. (1992) Chemical oxidation of N-hydroxyguanidine compounds. Release of nitric oxide, nitroxyl and possible relationship to the mechanism of biological nitric oxide generation. Biochem. Pharmacol. 43, 607-613.
44. Garber, E. A., and Hollocher, T. C. (1982) Positional isotopic equivalence of nitrogen in N2O produced by the denitrifying bacterium Pseudomonas stutzeri. Indirect evidence for a nitroxyl pathway. J. Biol. Chem. 257, 4705-4708.
45. Fukuto, J. M., Hszieh, R., Gulati, P., Chiang, K. T., and Nagasawa, H. T. (1992) N,O-Diacylated-N-hydroxyarylsulfonamides: Nitroxyl precursors with potent smooth muscle relaxant properties. Biochem. Biophys. Res. Commun. 187, 1367-1373.
46. Wink, D. A., and Feelisch, M. (1996) Formation and detection of nitroxyl and nitrous oxide. In Methods in Nitric Oxide Research (Feelisch, M., and Stamler, J. S., Eds.) pp 403-412, John Wiley & Sons Ltd., London.
47. Miranda, K. M., Paolocci, N., Katori, T., Thomas, D. D., Ford, E., Bartberger, M. D., Espey, M. G., Kass, D. A., Feelisch, M., Fukuto, J. M., and Wink, D. A. (2003) A biochemical rationale for the discrete behavior of nitroxyl and nitric oxide in the cardiovascular system. Proc. Natl. Acad. Sci. U.S.A. 100, 9196-9201.
48. Fridovich, I. (1970) Quantitative aspects of the production of superoxide anion radical by milk xanthine oxidase. J. Biol. Chem. 245, 4053-4057.
49. Burton, K. (1957) Free energy data of biological interest. Ergeb. Physiol. Biol. Chem. Exp. Pharmakol. 49, 275-285.
50. Buettner, G. R. (1993) The pecking order of free radicals and antioxidants: lipid peroxidation, alpha-tocopherol, and ascorbate. Arch. Biochem. Biophys. 300, 535-543.
51. Wardman, P. (1989) Reduction potentials of one-electron couples involving free radicals in aqueous solution. J. Phys. Chem. Ref. Data 18, 1637-1755.
52. Wahl, S. M., McCartney-Francis, N., Chan, J., Dionne, R., Ta, L., and Orenstein, J. M. (2003) Nitric oxide in experimental joint inflammation. Benefit or detriment? Cells Tissues Organs 174, 26-33.
53. Datta, N., Mukherjee, S., Das, L., and Das, P. K. (2003) Targeting of immunostimulatory DNA cures experimental visceral leishmaniasis through nitric oxide up-regulation and T cell activation. Eur. J. Immunol. 33, 1508-1518.
54. Grisham, M. B., Pavlick, K. P., Laroux, F. S., Hoffman, J., Bharwani, S., and Wolf, R. E. (2002) Nitric oxide and chronic gut inflammation: controversies in inflammatory bowel disease. J. Invest. Med. 50, 272-283.