183
Views
35
CrossRef citations to date
0
Altmetric
Original Article

Autoxidation of naphthohydroquinones: Effects of pH, naphthoquinones and superoxide dismutase

Pages 245-253 | Received 20 Apr 1999, Published online: 07 Jul 2009

References

  • Thomson R.H. Naturally Occurring Quinones. III: Recent Advances. Chapman and Hall, London 1987
  • Schuetzle D. Sampling of vehicle emissions for chemical analysis and biological testing. Environmental Health Perspectives 1983; 47: 65–80
  • Prior W.A. Cigarette smoke radicals and the role of free radicals in chemical carcinogenicity. Environmental Health Perspectives 1997; 105(Suppl. 4)875–882
  • Andaya A.A., Di Giulio R.T. Acute toxicities and hematological effects of two substituted naphthoquinones in channel catfish. Archives of Environmental Contamination and Toxicology 1987; 16: 233–238
  • Bayona J.M., Casellas M., Fernández P., Solanas A.M., Albaigés J. Sources and seasonal variability of mutagenic agents in the Barcelona city aerosol. Chemosphere 1994; 29: 441–450
  • Duke J.A. Handbook of Medicinal Herbs. CRC Press, Boca Raton 1985
  • Watt J.M., Breyer-Brandwijk M.G. The Medicinal and Poisonous Plants of Southern and Eastern AfricaSecond Edition. Livingstone, Edinburgh 1962
  • O'Brien P.J. Molecular mechanisms of quinone cytotoxicity. Chemico-Biological Interactions 1991; 80: 1–41
  • Workman P. Enzyme-directed bioreductive drug development revisited: a commentary on recent progress and future prospects with emphasis on quinone anticancer agents and quinone metabolising enzymes, particularly DT-diaphorase. Oncology Research 1994; 6: 461–475
  • Morrison R.K., Brown D.E., Oleson J.J., Cooney D.A. Oral toxicology studies with lapachol. Toxicology and Applied Pharmacology 1970; 17: 1–11
  • Munday R., Smith B.L., Fowke E.A. Haemolytic activity and nephrotoxicity of 2-hydroxy-1,4-naphthoquinone in rats. Journal of Applied Toxicology 1991; 11: 85–90
  • Munday R., Fowke E.A., Smith B.L., Munday C.M. Comparative toxicity of alkyl-1,4-naphthoquinones in rats: relationship to free radical production in vitro. Free Radical Biology and Medicine 1994; 16: 725–731
  • Munday R., Smith B.L., Munday C.M. Toxicity of 2,3-dialkyl-1,4-naphthoquinones in rats: comparison with cytotoxicity in vitro. Free Radical Biology and Medicine 1995; 19: 759–765
  • Margolin K.A., Akman S.A., Leong L.A., Morgan R.J., Somlo G., Raschko J.W., Ahn C., Doroshow J.H. Phase I study of mitomycin c and menadione in advanced solid tumors. Cancer Chemotherapy and Pharmacology 1995; 36: 293–298
  • Lau S.S. Quinone-thioether-mediated nephrotoxicity. Drug Metabolism Reviews 1995; 27: 125–141
  • Bhuyan D.K., Huang X.R., Kuriakose G., Garner W.H., Bhuyan K.C. Menadione-induced oxidative stress accelerates onset of Emory mouse cataract in vivo. Current Eye Research 1997; 16: 519–526
  • Wells P.G., Wilson B., Lubek B.M. In vivo murine studies on the biochemical mechanism of naphthalene cataract. Toxicology and Applied Pharmacology 1989; 99: 466–473
  • Cavalieri E.L., Stack D.E., Devanesan P.D., Todorovic R., Dwivedy I., Higginbotham S., Johansson S.L., Patil K.D., Gross M.L., Gooden J.K., Ramanathan R., Cerny R.L., Rogan E.G. Molecular origin of cancer: catechol estrogen-3,4-quinones as endogenous tumor initiators. Proceedings of the National Academy of Sciences USA 1997; 94: 10937–10942
  • Flowers L., Ohnishi S.T., Penning T.M. DNA strand scission by polycylic hydrocarbon o-quinones: role of reactive oxygen species, Cu(II)/Cu(I) redox cycling, and o-semiquinone anion radicals. Biochemistry 1997; 36: 8640–8648
  • Bock K.W., Lilienblum W., Fischer G., Schirmer G., Bock-Hennig B.S. The role of conjugation reactions in detoxication. Archives of Toxicology 1987; 60: 22–29
  • Losito R., Owen C.A., Flock E.V. Metabolism of [14C] menadione. Biochemistry 1967; 6: 62–68
  • Ernster L. DT diaphorase: a historical review. Chemica Scripta 1987; 27A: 1–13
  • Lind C., Cadenas E., Hochstein P., Ernster L. DT-diaphorase: purification, properties, and function. Methods in Enzymology 1990; 186: 287–301
  • Cadenas E. Antioxidant and prooxidant functions of DT-diaphorase in quinone metabolism. Biochemical Pharmacology 1995; 49: 127–140
  • Brunmark A., Cadenas E. Redox and addition chemistry of quinoid compounds and its biological implications. Free Radical Biology and Medicine 1989; 7: 435–477
  • Munday R. Inhibition of naphthohydroquinone autoxidation by DT-diaphorase (NAD(P)H: [quinone acceptor] oxidoreductase). Redox Report 1997; 3: 189–196
  • Munday R. Autoxidation of naphthohydroquinones: effects of metals, chelating agents, and superoxide dismutase. Free Radical Biology and Medicine 1997; 22: 689–695
  • Ishii T., Fridovich I. Dual effects of superoxide dismutase on the autoxidation of 1,4-naphthohydroquinone. Free Radical Biology and Medicine 1990; 8: 21–24
  • Munday R., Smith B.L., Munday C.M. Effects of butylated hyroxyanisole and dicoumarol on the toxicity of menadione to rats. Chemico-Biological Interactions 1998; 108: 155–170
  • Munday R., Smith B.L., Munday C.M. Effects of butylated hydroxyanisole on the toxicity of 2-hydroxy-1,4-naphthoquinone to rats. Chemico-Biological Interactions 1999; 117: 241–256
  • Cadenas E., Mira D., Brunmark A., Lind C., Segura-Aguilar J., Ernster L. Effects of superoxide dismutase on the autoxidation of various hydroquinones — a possible role of superoxide dismutase as a superoxide: semiquinone oxidoreductase. Free Radical Biology and Medicine 1998; 5: 71–79
  • Klapper M.H., Hackett D.P. The oxidatic activity of horseradish peroxidase. 1. Oxidation of hydro- and naphthohydroquinones. Journal of Biological Chemistry 1963; 238: 3736–3742
  • Lind C., Hochstein P., Ernster L. DT-Diaphorase as a quinone reductase: a cellular control device against semiquinone and superoxide radical formation. Archives of Biochemistry and Biophysics 1982; 216: 178–185
  • James T.H., Weissberger A. Oxidation processes. XI. The autoxidation of durohydroquinone. Journal of the American Chemical Society 1938; 60: 98–104
  • Eyer P. Effects of superoxide dismutase on the autoxidation of 1,4-hydroquinone. Chemico-Biological Interactions 1991; 80: 159–176
  • Öllinger K., Buffinton G.D., Ernster L., Cadenas E. Effect of superoxide dismutase on the autoxidation of substituted hydro- and semi-naphthoquinones. Chemico-Biological Interactions 1990; 73: 53–76
  • Öllinger K., Llopis J., Cadenas E. Study of the redox properties of naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) and its glutathionyl conjugate in biological reactions: one and two-electron enzymatic reduction. Archives of Biochemistry and Biophysics 1989; 275: 514–530
  • Buffinton G.D., Öllinger K., Brunmark A., Cadenas E. DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl conjugates. Biochemical Journal 1989; 257: 561–571
  • Llopis J., Ernster L., Cadenas E. Effect of glutathione on the redox transitions of naphthohydroquinone derivatives during DT-diaphorase catalysis. Free Radical Research Communications 1990; 8: 271–285
  • Öllinger K., Brunmark A. Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes. Journal of Biological Chemistry 1991; 266: 21496–21503
  • Giulivi C., Cadenas E. One- and two-electron reduction of 2-methyl-1,4-naphthoquinone bioreductive alkylating agents: kinetic studies, free radical production, thiol oxidation and DNA-strand-break formation. Biochemical Journal 1994; 301: 21–30
  • Bandy B., Moon J.A., Davison I. Multiple actions of superoxide dismutase: why can it both inhibit and stimulate reduction of oxygen by hydroquinones?. Free Radical Biology and Medicine 1990; 9: 143–148
  • Li Y., Kuppusamy P., Zweier J.L., Trush M.A. Role of Cu/Zn-superoxide dismutase in xenobiotic activation. 1. Chemical reactions involved in the Cu/Zn-superoxide dismutase-accelerated oxidation of the benzene metabolite 1,4-hydroquinone. Molecular Pharmacology 1996; 49: 404–411
  • Fieser L.F. Convenient procedures for the preparation of antihemorrhagic compounds. Journal of Biological Chemistry 1940; 133: 391–396
  • Jacobsen N., Torssell K. Radikalische Alkylierung von Chinonen: Erzeugung von Radikalen in Redoxreaktionen. Liebig's Annalen der Chemie 1972; 763: 135–147
  • Fieser L.F., Campbell W.P., Fry E.M., Gates M.D. Naphthoquinones of the vitamin K1 type of structure. Journal of the American Chemical Society 1939; 61: 3216–3223
  • Fieser L.F. The alkylation of hydroxynapthoquinone. I. Ortho-esters. Journal of the American Chemical Society 1926; 48: 2922–2937
  • Fieser L.F., Brown R.H. Synthesis of naphthoquinones for studies of the inhibition of enzyme systems. Journal of the American Chemical Society 1949; 71: 3609–3614
  • Fieser L.F. Naphthoquinone antimalarials. III. Diene synthesis of 1,4-naphthoquinones. Journal of the American Chemical Society 1948; 70: 3165–3174
  • Fieser L.F., Hartwell J.L. The reaction of hydrazoic acid with the naphthoquinones. Journal of the American Chemical Society 1935; 57: 1482–1484
  • Kehrmann P. Ueber Chinonimide und Aminochinone. Berichte der deutschen chemischen Gesellschaft 1894; 27: 3337–3347
  • Byrde R.J.W., Woodcock D. Fungicidal activity and chemical constitution. II. Compounds related to 2,3-dichloro-1,4-naphthoquinone. Annals of Applied Biology 1953; 40: 675–687
  • Friedmann E., Marrian D.H., Simon-Reuss I. Halogen derivatives of the 1,4-naphthoquinone group and the maleic acid series in their action on the mitosis of chick fibroblasts. Biochimica et Biophysica Acta 1952; 8: 680–686
  • Willstätter R., Schuler L. Über Bildung indigoider Verbindungen aus halogenierten Naphtholen. Berichte der deutschen chemischen Gesellschaft 1928; 61: 362–372
  • Willstätter R., Wheeler A.S. Über die Isomerie der Hydro-juglone. Berichte der deutschen chemischen Gesellschaft 1914; 47: 2796–2801
  • Wardman P. Reduction potentials of one-electron couples involving free radicals in aqueous solution. Journal of Physical Chemistry Reference Data 1989; 18: 1636–1755
  • Butler J., Hoey B.M. The apparent inhibition of superoxide dismutase activity by quinones. Journal of Free Radical Biology and Medicine 1986; 2: 77–81
  • Meisel D. Free energy correlation of rate constants for electron transfer between organic systems in aqueous solutions. Chemical Physics Letters 1975; 34: 263–266
  • Tatsumi H., Nakase H., Kano K., Ikeda T. Mechanistic study of the autoxidation of reduced flavin and quinone compounds. Journal of Electroanalytical Chemistry 1998; 443: 236–242
  • Winterbourn C.C., Cowden W.B., Sutton H.C. Auto-oxidation of dialuric acid, divicine and isouramil. Superoxide dependent and independent mechanisms. Biochemical Pharmacology 1989; 38: 611–618
  • Clark W.M. Oxidation-Reduction Potentials of Organic Systems. Williams & Wilkins, Baltimore 1960
  • Fieser L.F., Fieser M. The tautomerism of the aminonaphthoquinones. Journal of the American Chemical Society 1934; 56: 1565–1578
  • Bishop C.A., Tong L.K.J. Equilibria of substituted semiquinones at high pH. Journal of the American Chemical Society 1965; 87: 501–505
  • Prakash G., Hodnett E.M. Discriminant analysis and structure-activity relationships. 1. Naphthoquinones. Journal of Medicinal Chemistry 1978; 21: 369–374
  • Driebergen R.J., den Hartigh J., Holthuis J.J.M., Hulshoff A., van Oort W.J., Kelder S.J.P., Verboom W., Reinhoudt D.N., Bos M., van der Linden W.E. Electrochemistry of potentially bioreductive alkylating quinones. Part 1. Electrochemical properties of relatively simple quinones, as model compounds of mitomycintype antitumouragents. Analytica Chimica Acta 1990; 233: 251–268
  • Swallow A.J. Physical chemistry of semiquinones. Function of Quinones in Energy Conserving Systems, B.L. Trumpower. Academic Press, New York 1982; 59–72

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.