Alloxan-dialuric acid cycling: A complex redox mechanism

References

• Dunn JS, Sheehan HL, McLetchie NGB. Necrosis of the islets of Langerhans produced experimentally. Lancet 1943; 241: 484–487
   Google Scholar
• Munday R, Ludwig K, Lenzen S. The relationship between the physicochemical properties and the biological effects of alloxan and several N-alkyl substituted alloxan derivatives. J Endocrinol 1993; 139: 153–163
   PubMed Web of Science ®Google Scholar
• Elsner, M, Gurgul-Convey, E, Lenzen, S. Relation between triketone structure, generation of reactive oxygen species and selective toxicity of diabetogenic agent alloxan. Antioxid Redox Signal. 2008;10:691–700. doi:10.1089/ars.2007.1816.
   Google Scholar
• Czerwiñska M, Sikora A, Szajerski P, Adamus J, Marcinek A, Gebicki J, Bednarek P. Mechanistic aspects of alloxan diabetogenic activity: a key role of keto-enol inversion of dialuric acid on ionization. J Phys Chem A 2006; 110: 7272–7278
   PubMed Web of Science ®Google Scholar
• Brömme HJ, Weinandy R, Peschke E. Influence of oxygen concentration on redox cycling of alloxan and dialuric acid. Horm Metab Res 2005; 37: 729–733
   PubMed Web of Science ®Google Scholar
• Elsner M, Gurgul-Convey E, Lenzen S. Relative importance of cellular uptake and reactive oxygen species for the toxicity of alloxan and dialuric acid to insulin-producing cells. Free Radic Biol Med 2006; 41: 825–834
   PubMed Web of Science ®Google Scholar
• Kwart H, Sarasohn IM. Studies on the mechanism of the benzilic acid rearrangement; the rearrangement of alloxan (I). J Am Chem Soc 1961; 83: 909–919
   Web of Science ®Google Scholar
• Reif DW, Samokyszyn VM, Miller DM, Aust SD. Alloxan- and glutathione-dependent ferritin iron release and lipid peroxidation. Arch Biochem Biophys 1989; 269: 407–414
   PubMed Web of Science ®Google Scholar
• Brömme HJ, Eberlt H, Peschke D, Peschke E. Alloxan acts as prooxidant only under reducing conditions: influence of melatonin. Cell Mol Life Sci 1999; 55: 487–493
   PubMed Web of Science ®Google Scholar
• Houée-Levin C, Gardès-Albert M, Ferradini C, Pucheault J. Pulse radiolytic investigations of the redox system alloxan-dialuric acid: Evidence for a radical intermediate. Biochem Biophys Res Comm 1979; 91: 1196–1200
   PubMed Web of Science ®Google Scholar
• Houée-Levin C, Gardès-Albert M, Ferradini C, Pucheault J. Radiolysis study of the alloxan-dialuric acid couple. I. The reduction of alloxan by and *COO− radicals. Radiat Res 1980; 83: 270–278
   Web of Science ®Google Scholar
• Patterson JW, Lazarow A, Levey S. Alloxan and dialuric acid: their stabilities and ultraviolet absorption spectra. J Biol Chem 1949; 177: 187–196
   PubMed Web of Science ®Google Scholar
• Winterbourn CC, Cowden WB, Sutton HC. Auto-oxidation of dialuric acid, divicine and isouramil superoxide dependent and independent mechanisms. Biochem Pharmacol 1989; 38: 611–618
   PubMed Web of Science ®Google Scholar
• McElroy WJ, Waygood SJ. Kinetics of the reactions of radicals with , and Fe+2. J Chem Soc Faraday Trans 1990; 86: 2557–2564
   Google Scholar
• Rosso JA, Bertollotti SG, Braun AM, Mártire DO, Gonzalez MC. Reactions of carbon dioxide radical anion with substituted benzenes. J Phys Org Chem 2001; 14: 300–309
   Web of Science ®Google Scholar
• Choure SC, Bamatraf MMM, Rao BSM, Das R, Mohan H, Mittal JP. Hydroxylation of chlorotoluenes and cresols: a pulse radiolysis, laser flash photolysis, and product analysis study. J Phys Chem A 1997; 101: 9837–9845
   Web of Science ®Google Scholar
• Dohrmann JK, Livingston R, Zeldes H. Paramagnetic resonance study of liquids during photolysis. XII. Alloxan, parabanic acid and related compounds. J Am Chem Soc 1971; 93: 3343–3349
   Web of Science ®Google Scholar
• Bielski BHJ, Cabelli DE, Arudi RL, Ross AB. Reactivity of HO2/O2− radicals in aqueous solution. J Phys Chem Ref Data 1985; 14: 1041–1100
   Web of Science ®Google Scholar
• Bielski BHJ, Cabelli DE. Superoxide and hydroxyl radical chemistry in aqueous solution. Active oxygen in chemistry, CS Foote, JS Valentine, A Greenberg, JF Liebman. Chapman and Hall, London 1995; 66–104
   Google Scholar
• Wardman P. Reduction potentials of one-electron couples involving free radicals in aqueous solution. J Phys Chem Ref Data 1989; 18: 1637–1755
   Web of Science ®Google Scholar
• Houée-Levin C, Gardes-Albert M, Ferrandini C, Pucheault J. Radiolysis study of the alloxan-dialuric acid couple. II. The autooxidation of dialuric acid. Radiat Res 1981; 88: 20–28
   PubMed Web of Science ®Google Scholar
• Houée C, Gardès M, Pucheault J, Ferradini C. Radical chemistry of alloxan-dialuric acid: role of superoxide radical. Bull Euro Physiopath Resp 1981; 17(suppl)43–48
   PubMedGoogle Scholar
• Rosso JA, Allegretti P, Mártire DO, Gonzalez MC. Reaction of sulphate and phosphate radicals with α, α, α-trifluorotoluene. J Chem Soc Perkin Trans 1999; 2: 205–210
   Google Scholar
• Kalyanaraman B, Korytowski W, Pilas B, Sarna T, Land EJ, Truscott TG. Reaction between ortho-semiquinones and oxygen: pulse radiolysis, electron spin resonance, and oxygen uptake studies. Arch Biochem Biophys 1988; 266: 277–284
   PubMed Web of Science ®Google Scholar
• Patel KB, Willson RL. Semiquinone free radicals and oxygen pulse radiolysis study of one electron transfer equilibria. J Chem Soc Faraday Trans I 1973; 69: 814–821
   Google Scholar
• Roginsky VA, Pisarenko LM, Bors W, Michel C. The kinetics and thermodynamics of quinine-semiquinone-hydroquinone systems under physiological conditions. J Chem Soc Perkin Trans 1999; 2: 871–876
   Google Scholar
• Brömme HJ, Weinandy R, Peschke D, Peschke E. Simultaneous quantitative determination of alloxan, GSH and GSSG by HPLC. Estimation of the frequency of redox cycling between alloxan and dialuric acid. Horm Metab Res 2001; 33: 106–109
   PubMed Web of Science ®Google Scholar
• Winterbourn CC, Munday R. Glutathione-mediated redox cycling of alloxan. Biochem Pharm 1989; 28: 271–277
   Google Scholar
• Madej E, Wardman P. The oxidizing power of the glutathione thiyl radical as measured by its electrode potential at physiological pH. Arch Biochem Biophys 2007; 462: 94–102
   PubMed Web of Science ®Google Scholar
• Shen D, Dalton TP, Nebert DW, Shertzer HG. Glutathione redox state regulates mitochondrial reactive oxygen production. J Biol Chem 2005; 280: 25305–25312
   PubMed Web of Science ®Google Scholar
• Neta P, Huie RE, Ross AB. Rate constants for reactions of inorganic radicals in aqueous solution. J Phys Chem Ref Data 1988; 17: 1027–1284
   Web of Science ®Google Scholar
• David Gara PM, Bucharsky E, Wörner M, Braun AM, Mártire DO, Gonzalez MC. Trichloroacetic acid dehalogenation by reductive radicals. Inorg Chim Acta 2007; 360: 1209–1216
   Web of Science ®Google Scholar