Concerted action of DT-diaphorase and superoxide dismutase in preventing redox cycling of naphthoquinones: An evaluation

References

• Thomson R.H. Naturally occurring quinones. III: Recent advances. Chapman and Hall, London 1987
   Google Scholar
• Duke J.A. Handbook of medicinal herbs. CRC Press, Boca Raton 1985
   Google Scholar
• Watt J.M., Breyer-Brandwijk M.G. The medicinal and poisonous plants of Southern and Eastern AfricaSecond edn. Livingstone, Edinburgh 1962
   Google Scholar
• Hudson A.T. Antimalarial hydroxynaphthoquinones. Special Publications of the Royal Society of Chemistry 1988; 65: 266–283
   Web of Science ®Google Scholar
• Powis G. Metabolism and reactions of quinone anticancer agents. Pharmacology and Therapeutics 1987; 35: 57–162
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• O'Brien P.J. Molecular mechanisms of quinone cytotoxicity. Chemico-Biological Interactions 1991; 80: 1–41
   PubMed Web of Science ®Google Scholar
• Ahn B.-Z., Sok D.-E. Michael acceptors as a tool for anticancer drug design. Current Pharmaceutical Design 1996; 2: 247–262
   Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Lau S.S. Quinone-thioether-mediated nephrotoxicity. Drug Metabolism Reviews 1995; 27: 125–141
   PubMed Web of Science ®Google Scholar
• Comporti M. Three models of free radical-induced cell injury. Chemico-Biological Internactions 1989; 27: 1–56
   Google Scholar
• Brunmark A., Cadenas E. Redox and addition chemistry of quinoid compounds and its biological implications. Free Radical Biology and Medicine 1989; 7: 435–477
   PubMed Web of Science ®Google Scholar
• Smith M.T., Evans C.G., Thor H., Orrenius S. Oxidative stress, H. Sies. Academic Press, London 1985; 91–113, In
   Google Scholar
• Schenk G., Vetter K.J., Müller R. Polarographische Untersuchungen der Autoxidation von 1,2,4-Trioxynaphthalin. Archiv der Pharmazie 1959; 292: 62–70
   Google Scholar
• Colpa-Boonstra J.P., Slater E.C. The possible role of vitamin K in the respiratory chain. Biochimica et Biophysica Acta 1958; 27: 122–133
   PubMed Web of Science ®Google Scholar
• Munday R. Autoxidation of naphthohydroquinones: effects of metals, chelating agents, and superoxide dismutase. Free Radical Biology and Medicine 1997; 22: 689–695
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Munday R. Inhibition of naphthohydroquinone autoxidation by DT-diaphorase (NAD(P)H:[quinone acceptor] oxidoreductase). Redox Report 1997; 3: 189–196
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Munday R. Inhibition of 2,3-dimethyl-1,4-naphthohydroquinone autoxidation by copper and by superoxide dismutase. Free Radical Biology and Medicine 1999; 26: 1475–1479
   Google Scholar
• Munday R. Autoxidation of naphthohydroquinones: effects of pH, naphthoquinones and superoxide dismutase. Free Radical Research 2000; 32: 245–253
   PubMed Web of Science ®Google Scholar
• Segura-Aguilar J., Lind C. On the mechanism of the Mn3+-induced neurotoxicity of dopamine: prevention of quinone-derived oxygen toxicity by DT-diaphorase and superoxide dismutase. Chemico-Biological Interactions 1989; 72: 309–324
   PubMed Web of Science ®Google Scholar
• Ernster L. DT-diaphorase: its structure, function, regulation and role in antioxidant defence and cancer chemotherapy. Pathophysiology of lipid peroxides and related free radicals, K. Yagi. Japan Scientific Societies Press, Tokyo 1998; 149–168, In
   Google Scholar
• Fieser L.F. Convenient procedures for the preparation of antihemorrhagic compounds. Journal of Biological Chemistry 1940; 133: 391–396
   Google Scholar
• Jacobsen N., Torssell K. Radikalische Alkylierung von Chinonen: Erzeugung von Radikalen in Redoxreaktionen. Liebig's Annalen der Chemie 1972; 763: 135–147
   Google Scholar
• 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
   Web of Science ®Google Scholar
• Munday R. In vivo toxicity of thiols: relationship to rate of one-electron oxidation by oxyhaemoglobin. Methods in Enzymology 1995; 251: 117–120
   PubMed Web of Science ®Google Scholar
• Lind C., Cadenas E., Hochstein P., Ernster L. DT-diaphorase: purification, properties, and function. Methods in Enzymology 1990; 186: 287–301
   PubMed Web of Science ®Google Scholar
• Ernster L., Danielson L., Ljunggren M. DT-diaphorase I. Purification from the soluble fraction of rat-liver cytoplasm, and properties. Biochemica et Biophysica Acta 1962; 58: 171–188
   PubMed Web of Science ®Google Scholar
• McCord J.M., Fridovich I. Superoxide dismutase. An enzymic function for erythrocuprein (hemocuprein). Journal of Biological Chemistry 1969; 244: 6049–6055
   PubMed Web of Science ®Google Scholar
• Eyer P. Effects of superoxide dismutase on the autoxidation of 1,4-hydroquinone. Chemico-Biological Interactions 1991; 80: 159–176
   PubMed Web of Science ®Google Scholar
• Bandy B., Moon J.A., Davison J. 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
   PubMed Web of Science ®Google Scholar
• Munday R. Generation of superoxide radical, hydrogen peroxide and hydroxyl radical during the autoxidation of N,N,N′,N′-tetramethyl-p-phenylenediamine. Chemico-Biological Interactions 1988; 65: 133–143
   Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Munday R., Winterbourn C.C. Reduced glutathione in combination with superoxide dismutase as an important biological antioxidant defence mechanism. Biochemical Pharmacology 1989; 38: 4349–4352
   PubMed Web of Science ®Google Scholar
• Mukherjee T. One-electron reduction of juglone (5-hydroxy-1,4-naphthoquinone): a pulse radiolysis study. Radiation Physics and Chemistry 1987; 29: 455–462
   Google Scholar
• Munday R., Smith B.L., Munday C.M. Effects of butylated hydroxyanisole and dicoumarol on the toxicity of menadione to rats. Chemico-Biological Interactions 1998; 108: 155–170
   PubMed Web of Science ®Google Scholar
• Munday R., Smith B.L., Munday C.M. Effect of inducers of DT-diaphorase on the toxicity of 2-methyl and 2-hydroxy-1,4-naphthoquinone to rats. Chemico-Biological Interactions 1999; 123: 219–237
   Google Scholar
• 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
   PubMed Web of Science ®Google Scholar