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Chemical Compound Review

SureCN48171     5,6-dihydroxy-1H-pyrimidine- 2,4-dione

Synonyms: LS-135720, BRN 0135130, AC1L28PK, 102636-37-3, Isodialuric acid, ...
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Disease relevance of Isodialuric acid


High impact information on Isodialuric acid

  • The toxic action of alloxan on animal cells, particularly the beta cells of pancreas, may be caused by rapid oxidation of cellular NADPH and generation of cytotoxic dialuric acid catalyzed by the thioredoxin system [4].
  • After a second attack by another .OH, the BA radical is transformed into dialuric acid (DA), which autoxidizes via the alloxan radical (.ALX) to ALX [5].
  • Alloxan and its reduced derivative, dialuric acid, act as a redox couple, driven by reduced glutathione (GSH) or L-cysteine, generating in vitro in the presence of oxygen, both superoxide radical and hydrogen peroxide [6].
  • The peroxidation of membrane phospholipids induced in vitro by ascorbic acid or by dialuric acid (hydroxybarbituric acid) does not occur in the absence of traces of metal ions [7].
  • The oxidation of these substrates by Br2 led to a similar profile of intermediate and stable products indicating that the dialuric and isodialuric acid derivatives of dCyd largely undergo deamination before they transform into 5-oh-dHyd [8].

Chemical compound and disease context of Isodialuric acid


Biological context of Isodialuric acid


Anatomical context of Isodialuric acid


Associations of Isodialuric acid with other chemical compounds


Gene context of Isodialuric acid


Analytical, diagnostic and therapeutic context of Isodialuric acid


  1. Relative importance of cellular uptake and reactive oxygen species for the toxicity of alloxan and dialuric acid to insulin-producing cells. Elsner, M., Gurgul-Convey, E., Lenzen, S. Free Radic. Biol. Med. (2006) [Pubmed]
  2. Relative activity of alpha-tocopherol and gamma-tocopherol in preventing oxidative red cell hemolysis. Bieri, J.G., Evarts, R.P., Gart, J.J. J. Nutr. (1976) [Pubmed]
  3. A novel activity of E. coli uracil DNA N-glycosylase excision of isodialuric acid (5,6-dihydroxyuracil), a major product of oxidative DNA damage, from DNA. Zastawny, T.H., Doetsch, P.W., Dizdaroglu, M. FEBS Lett. (1995) [Pubmed]
  4. Enzymatic reduction of alloxan by thioredoxin and NADPH-thioredoxin reductase. Holmgren, A., Lyckeborg, C. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  5. Transformation of barbituric acid into alloxan by hydroxyl radicals: interaction with melatonin and with other hydroxyl radical scavengers. Brömme, H.J., Mörke, W., Peschke, E. J. Pineal Res. (2002) [Pubmed]
  6. Alloxan acts as a prooxidant only under reducing conditions: influence of melatonin. Brömme, H.J., Ebelt, H., Peschke, D., Peschke, E. Cell. Mol. Life Sci. (1999) [Pubmed]
  7. Inhibition of the iron-catalysed formation of hydroxyl radicals from superoxide and of lipid peroxidation by desferrioxamine. Gutteridge, J.M., Richmond, R., Halliwell, B. Biochem. J. (1979) [Pubmed]
  8. Oxidation of 5-hydroxypyrimidine nucleosides to 5-hydroxyhydantoin and its alpha-hydroxy-ketone isomer. Rivière, J., Klarskov, K., Wagner, J.R. Chem. Res. Toxicol. (2005) [Pubmed]
  9. Effect of dietary vitamin E and vitamin C on respiration and swelling of guinea pig liver mitochondria. Chen, L.H., Chang, M.L. J. Nutr. (1978) [Pubmed]
  10. Transfer of alpha-tocopherol from plasma to erythrocytes in vitamin E-deficient rats. Nakamura, T., Masugi, F. International journal for vitamin and nutrition research. Internationale Zeitschrift für Vitamin- und Ernährungsforschung. Journal international de vitaminologie et de nutrition. (1979) [Pubmed]
  11. Changes of alpha-tocopherol levels in red blood cells and plasma with respect to hemolysis induced by dialuric acid in vitamin E-deficient rats. Mino, M., Kitagawa, M., Nakagawa, S. J. Nutr. Sci. Vitaminol. (1981) [Pubmed]
  12. Glutathione-mediated redox cycling of alloxan. Mechanisms of superoxide dismutase inhibition and of metal-catalyzed OH. formation. Winterbourn, C.C., Munday, R. Biochem. Pharmacol. (1989) [Pubmed]
  13. The desolvation and oxidation of crystals of dialuric acid monohydrate. Clay, R.J., Knevel, A.M., Byrn, S.R. Journal of pharmaceutical sciences. (1982) [Pubmed]
  14. Formation of isodialuric acid lesion within DNA oligomers via one-electron oxidation of 5-hydroxyuracil: characterization, stability and excision repair. Simon, P., Gasparutto, D., Gambarelli, S., Saint-Pierre, C., Favier, A., Cadet, J. Nucleic Acids Res. (2006) [Pubmed]
  15. Relative antioxidant effectiveness of alpha-tocopherol and gamma-tocopherol in iron-loaded rats. Dillard, C.J., Gavino, V.C., Tappel, A.L. J. Nutr. (1983) [Pubmed]
  16. Inhibition of aconitase by alloxan and the differential modes of protection of glucose, 3-O-methylglucose, and mannoheptulose. Lenzen, S., Mirzaie-Petri, M. Naunyn Schmiedebergs Arch. Pharmacol. (1992) [Pubmed]
  17. Release of iron from ferritin by divicine, isouramil, acid-hydrolyzed vicine, and dialuric acid and initiation of lipid peroxidation. Monteiro, H.P., Winterbourn, C.C. Arch. Biochem. Biophys. (1989) [Pubmed]
  18. Comparison of four erythrocyte fragility tests as indicators of vitamin E status in adult dogs. Pillai, S.R., Steiss, J.E., Traber, M.G., Kayden, H.J., Wright, J.C. J. Comp. Pathol. (1992) [Pubmed]
  19. Simultaneous quantitative determination of alloxan, GSH and GSSG by HPlc. Estimation of the frequency of redox cycling between alloxan and dialuric acid. Brömme, H.J., Weinandy, R., Peschke, D., Peschke, E. Horm. Metab. Res. (2001) [Pubmed]
  20. In vitro effects of alloxan-vanadium combination on lipid peroxidation and on antioxidant enzyme activity. Alexandrova, A., Kirkova, M., Russanov, E. Gen. Pharmacol. (1998) [Pubmed]
  21. Observations on the mechanism of the oxygen/dialuric acid-induced hemolysis of vitamin e-deficient rat red blood cells and the protective roles of catalase and superoxide dismutase. Fee, J.A., Bergamini, R., Briggs, R.G. Arch. Biochem. Biophys. (1975) [Pubmed]
  22. Therapeutic efficacy of vitamin E and selenium in treating hemolytic anemia of owl monkeys (Aotus trivirgatus). Sehgal, P.K., Bronson, R.T., Brady, P.S., McIntyre, K.W., Elliott, M.W. Lab. Anim. Sci. (1980) [Pubmed]
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