85
Views
13
CrossRef citations to date
0
Altmetric
Original Article

Quinone-enhanced Ascorbate Reduction of Nitric Oxide: Role of Quinone Redox Potential

, &
Pages 1107-1112 | Received 07 Jul 2004, Published online: 07 Jul 2009

References

  • Bolton, J.L. (2002) "Quinoids, quinoid radicals, and phenoxyl radicals formed from estrogens and antiestrogens", Toxicology 177, 55–65.
  • Wardman, P. (2001) "Electron transfer and oxidative stress as key factors in the design of drugs selectively active in hypoxia", Curr. Med. Chem. 8, 739–761.
  • Monks, T.J. and Jones, D.C. (2002) "The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers", Curr. Drug Metab. 3, 425–438.
  • Roginsky, V.A., Barsukova, T.K., Bruchelt, G. and Stegmann, H.B. (1998) "Kinetics of redox interaction between substituted 1,4-benzoquinones and ascorbate under aerobic conditions: critical phenomena", Free Radic. Res. 29, 115–125.
  • 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.
  • Roginsky, V.A., Bruchelt, G. and Stegmann, H.B. (1998) "Fully reversible redox cycling of 2,6-dimethoxy-1,4-benzoquinone induced by ascorbate", Biochemistry (Mosc.) 63, 200–206.
  • Land, E.J., Cooksey, C.J. and Riley, P.A. (1990) "Reaction kinetics of 4-methoxy ortho benzoquinone in relation to its mechanism of cytotoxicity: a pulse radiolysis study", Biochem. Pharmacol. 39, 1133–1135.
  • Gutierrez, P.L. (1988) "The influence of ascorbic acid on the free-radical metabolism of xenobiotics: the example of diaziquone", Drug Metab. Rev. 19, 319–343.
  • Pethig, R., Gascoyne, P.R., McLaughlin, J.A. and Szent-Gyorgyi, A. (1983) "Ascorbate-quinone interactions: electro-chemical, free radical, and cytotoxic properties", Proc. Natl Acad. Sci. USA 80, 129–132.
  • O'Brien, P.J., Kaul, H.K. and Rauth, A.M. (1990) "Differential cytotoxicity of diaziquone toward Chinese hamster ovary cells under hypoxic and aerobic exposure conditions", Cancer Res. 50, 1516–1520.
  • Alegria, A.E., Cordones, E., Santiago, G., Marcano, Y, Sanchez, S., Gordaliza, M. and Martin-Martin, M.L. (2002) "Reductive activation of terpenylnaphthoquinones", Toxi-cology 175, 167–175.
  • Alegria, A.E., Rivera, L., Cordones, E., Castro, V. and Sanchez-Cruz, P. (2002) "Role of membrane charge and semiquinone structure on oxygen consumption rates", J. Chem. Soc., Perkin Trans. 2(11), 1823–1828.
  • Russo, G., Leopold, J.A. and Loscalzo, J. (2002) "Vasoactive substances: nitric oxide and endothelial dysfunction in atherosclerosis", Vascul. Pharmacol. 38, 259–269.
  • Palmer, R.M., Ferrige, A.G. and Moncada, S. (1987) "Nitric oxide release accounts for the biological activity of endothelium-derived relaxing factor", Nature 327, 524–526.
  • Collier, J. and Vallance, P. (1989) "Second messenger role for NO widens to nervous and immune systems", Trends Pharmacol. Sci. 10, 427–431.
  • Gross, S.S. and Wolin, US. (1995) "Nitric oxide: patho-physiological mechanisms", Annu. Rev. Physiol. 57, 737–769.
  • Wink, D.A., Feelisch, M., Fukuto, J., Chistodoulou, D., Jourd'heuil, D., Grisham, MB., Vodovotz, Y., Cook, J.A., Krishna, M., DeGraff, W.G., Kim, S., Gamson, J. and Mitchell, J.B. (1998) "The cytotoxicity of nitroxyl: possible implications for the pathophysiological role of NO", Arch. Biochem. Biophys. 351, 66–74.
  • Ohshima, H., Gilibert, I. and Bianchini, F. (1999) "Induction of DNA strand breakage and base oxidation by nitroxyl anion through hydroxyl radical production", Free Radic. Biol. Med. 26, 1305–1313.
  • Bartberger, M.D., Liu, W., Ford, E., Miranda, KM., 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. USA 99, 10958–10963.
  • 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. USA 99, 7340–7345.
  • Colton, CA., Gbadegesin, M., Wink, D.A., Miranda, KM., Espey, M.G. and Vicini, S. (2001) "Nitroxyl anion regulation of the NMDA receptor", J. Neurochem. 78, 1126–1134.
  • Paolocci, N., Saavedra, W.F., Miranda, K.M., Martignani, C., Isoda, T., Hare, J.M., Espey, M.G., Fukuto, J.M., Feelisch, M., Wink, D.A. and Kass, D.A. (2001) "Nitroxyl anion exerts redox-sensitive positive cardiac inotropy in vivo by calcitonin gene-related peptide signaling", Proc. Natl Acad. Sci. USA 98, 10463–10468.
  • Ma, XI., 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. USA 96, 14617–14622.
  • Espey, M.G., Miranda, KM., Thomas, D.D. and Wink, D.A. (2002) "Ingress and reactive chemistry of nitroxyl-derived species within human cells", Free Radic. Biol. Med. 33, 827–834.
  • 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. 24, 1–9.
  • Earley, S. and Walker, B.R. (2003) "Increased nitric oxide production following chronic hypoxia contributes to attenu-ated systemic vasoconstriction", Am. J. Physiol. Heart Circ. Physiol. 284, H1655—H1661.
  • Chen, HI., Hu, CT., Wu, C.Y. and Wang, D. (1997) "Nitric oxide in systemic and pulmonary hypertension", J. Biomed. Sci. 4, 244–248.
  • Anse11, M.F., Nash, B.W. and Wilson, D.A. (1963) "Preparation of p-benzoquinones", J. Chem. Soc., 3028–3036.
  • 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.
  • Bensetiti, Z., lliuta, I., Larachi, F. and Grandjean, B.P.A. (1999) "Solubility of nitrous oxide in amine solutions", Ind. Eng. Chem. Res. 38, 328–332.
  • Poderoso, J.J., Carreras, MC., Schopfer, F., Lisdero, Riobo, NA., Giulivi, C., Boveris, AD., Boveris, A. and Cadenas, E. (1999) "The reaction of nitric oxide with ubiquinol: kinetic properties and biological significance", Free Radic. Biol. Med. 26, 925–935.
  • Roginsky, V.A., Pisarenko, L.M., Bors, W. and Michel, C. (1999) "The kinetics and thermodynamics of quinone-semiquinone-hydroquinone systems under physio-logical conditions", J. Chem. Soc., Perkin Trans. 2, 871–876.
  • Singh, R.J., Hogg, N. and Kalyanaraman, B. (1995) "Inter-action of nitric oxide with photoexcited rose bengal: evidence for one-electron reduction of nitric oxide to nitroxyl anion", Arch. Biochem. Biophys. 324, 367–373.
  • Yoo, J. and Fukuto, J.M. (1995) "Oxidation of N-hydroxy-guanidine by nitric oxide and the possible generation of vasoactive species", Biochem. Pharmacol. 50, 1995–2000.
  • Nagasawa, H.T., Kawle, SE, 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.
  • Turk, T. and Hollocher, T.C. (1992) "Oxidation of dithioth-reitol during turnover of nitric oxide reductase: evidence for generation of nitroxyl with the enzyme from Paracoccus denitrificans", Biochem. Biophys. Res. Commun. 183, 983–988.
  • Fukuto, J.M., Wallace, G.C., Hszieh, R. and Chaudhuri, G. (1992) "Chemical oxidation of N-hydroxyguanidine com-pounds. Release of nitric oxide, nitroxyl and possible relationship to the mechanism of biological nitric oxide generation", Biochem. Pharmacol. 43, 607–613.
  • Garber, E.A. and Hollocher, T.C. (1982) "Positional isotopic equivalence of nitrogen in N20 produced by the denitrifying bacterium Pseudomonas stutzeri. Indirect evidence for a nitroxyl pathway", J. Biol. Chem. 257, 4705–4708.
  • Fukuto, J.M., Hszieh, R., Gulati, P., Chiang, K.T. and Nagasawa, H.T. (1992) "N,0-diacylated-N-hydroxyarylsulfon-amides: nitroxyl precursors with potent smooth muscle relaxant properties", Biochem. Biophys. Res. Commun. 187, 1367–1373.
  • Wink, D.A. and Feelisch, M. (1996) "Formation and detection of nitroxyl and nitrous oxide", In: Feelisch, M. and Stamler, J.S., eds, Methods in Nitric Oxide Research (Wiley, London), pp 403–412.
  • Murphy, MT. and Sies, H. (1991) "Reversible conversion of nitroxyl anion to nitric oxide by superoxide dismutase", Proc. Natl Acad. Sci. USA 88, 10860–10864.
  • Sharpe, M.A. and Cooper, CT. (1998) "Reactions of nitric oxide with mitochondrial cytochrome c: a novel mechanism for the formation of nitroxyl anion and peroxynitrite", Biochem. J. 332 (Pt 1), 9–19.
  • Niketic, V, Stojanovic, S., Nikolic, A., Spasic, M. and Michelson, AM. (1999) "Exposure of Mn and FeSODs, but not Cu/ZnSOD, to NO leads to nitrosonium and nitroxyl ions generation which cause enzyme modification and inacti-vation: an in vitro study", Free Radic. Biol. Med. 27, 992–996.
  • Steenken, S. and Neta, E (1979) "Electron-transfer rates and equilibria between substituted phenoxide ions and phenoxyl radicals", J. Phys. Chem. 83, 1134–1137.
  • Buettner, G.R. (1993) "The pecking order of free radicals and antioxidants: lipid peroxidation, alpha-tocopherol, and ascorbate", Arch. Biochem. Biophys. 300, 535–543.
  • 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.
  • 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", Fur. J. Immunol. 33, 1508–1518.
  • Grisham, MB., Pavlick K.P., Laroux, ES., Hoffman, J., Bharwani, S. and Wolf, RT. (2002) "Nitric oxide and chronic gut inflammation: controversies in inflammatory bowel disease", J. Investig. Med. 50, 272–283.
  • Lawson, R.C., Ferrer, A., Flores, W. and Alegria, A.E. (1999) "Sonochemistry of quinones in argon-saturated aqueous solutions: enhanced cytochrome c reduction", Chem. Res. Toxicol. 12, 850–854.
  • Wardman, E (1989) "Reduction potentials of one-electron couples involving free radicals in aqueous solution", J. Phys. Chem. Ref. Data 18, 1637–1755.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.