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Chemical Compound Review

Hydrouracil     1,3-diazinane-2,4-dione

Synonyms: dihydrouracil, Dihydrouracile, DI-H-uracil, t6mvmvtj, SureCN29419, ...
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Disease relevance of DI-H-uracil


High impact information on DI-H-uracil

  • All of the mutations that reduce competition involve base changes that decrease homology to a eucaryotic tRNA consensus sequence in the highly conserved D and T psi regions [3].
  • RNA polymerase bypass at sites of dihydrouracil: implications for transcriptional mutagenesis [4].
  • Complexes with dihydrouracil and N-carbamyl-beta-alanine obtained for the yeast dihydropyrimidinase reveal the mode of substrate and product binding and allow conclusions about what determines substrate specificity, stereoselectivity, and the reaction direction among cyclic amidohydrolases [5].
  • Repair of dihydrouracil supported by base excision repair in mNTH1 knock-out cell extracts [6].
  • In the present study we used an in vitro repair system to investigate the mechanism for the removal of 5,6-dihydrouracil from DNA by mNTH1-deficient cell-free extracts derived from testes of mNTH1 knock-out mice [6].

Chemical compound and disease context of DI-H-uracil


Biological context of DI-H-uracil


Anatomical context of DI-H-uracil

  • The catabolism of dCyd was highest in macrophages where 25% of the added dCyd (0.5 microM, 0.5 nmol/million cells) had been converted to dihydrouracil after 30 min, and 90% after 12 h [13].
  • Cytoplasmic extracts from late passage fibroblasts also showed reduced activity with all three substrates suggesting that the residual hAPE, and activities that recognized dihydrouracil, were preferentially targeted to the nuclei [14].

Associations of DI-H-uracil with other chemical compounds


Gene context of DI-H-uracil

  • A series of dihydrouracil derivatives has been synthesized and investigated for their in vitro inhibitory activity toward human leukocyte elastase (HLE) and cathepsin G (Cath G) [20].
  • However, with DNA containing a DHU that is closely opposed to a single strand break, Ku inhibited the nicking activity of human endonuclease III as well as the amount of free double strand breaks induced by the enzyme [21].
  • Uracil to dihydrouracil ratio in plasma was evaluated as a surrogate marker for DPD deficiency, and showed values out of the range previously recorded from a reference, non-toxic population [22].
  • A. tumefacins hydantoinase was most active on 5,6-dihydrouracil and DL-5-methylhydantoin with only slight activity on DL-benzylhydantoin [23].
  • Like water, dihydrouracil does not bind to active charcoal, and its presence in the cell medium can result in an overestimation of the in situ thymidylate synthase activity [13].

Analytical, diagnostic and therapeutic context of DI-H-uracil

  • Northern blot and primer extension analyses revealed that the pydBC genes are induced by dihydrouracil and regulated under the control of sigma(54) recognized promoter at transcriptional level as a polycistronic operon [24].
  • A rapid, robust and sensitive HPLC method for analysis of uracil (U) and dihydrouracil (UH2) in plasma was developed using solid phase extraction and ultraviolet detection [25].


  1. HU protein of Escherichia coli has a role in the repair of closely opposed lesions in DNA. Hashimoto, M., Imhoff, B., Ali, M.M., Kow, Y.W. J. Biol. Chem. (2003) [Pubmed]
  2. A series of 5-(5,6)-dihydrouracil substituted 8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 4-fluorobenzylamide inhibitors of HIV-1 integrase and viral replication in cells. Embrey, M.W., Wai, J.S., Funk, T.W., Homnick, C.F., Perlow, D.S., Young, S.D., Vacca, J.P., Hazuda, D.J., Felock, P.J., Stillmock, K.A., Witmer, M.V., Moyer, G., Schleif, W.A., Gabryelski, L.J., Jin, L., Chen, I.W., Ellis, J.D., Wong, B.K., Lin, J.H., Leonard, Y.M., Tsou, N.N., Zhuang, L. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  3. The promoter sequence of a yeast tRNAtyr gene. Allison, D.S., Goh, S.H., Hall, B.D. Cell (1983) [Pubmed]
  4. RNA polymerase bypass at sites of dihydrouracil: implications for transcriptional mutagenesis. Liu, J., Zhou, W., Doetsch, P.W. Mol. Cell. Biol. (1995) [Pubmed]
  5. The Crystal Structures of Dihydropyrimidinases Reaffirm the Close Relationship between Cyclic Amidohydrolases and Explain Their Substrate Specificity. Lohkamp, B., Andersen, B., Piskur, J., Dobritzsch, D. J. Biol. Chem. (2006) [Pubmed]
  6. Repair of dihydrouracil supported by base excision repair in mNTH1 knock-out cell extracts. Elder, R.H., Dianov, G.L. J. Biol. Chem. (2002) [Pubmed]
  7. Covalent cross-linking of tRNAGly1 to the ribosomal P site via the dihydrouridine loop. Chen, J.K., Krauss, J.H., Hixson, S.S., Zimmermann, R.A. Biochim. Biophys. Acta (1985) [Pubmed]
  8. Role of enzymatically catalyzed 5-iodo-5,6-dihydrouracil ring hydrolysis on the dehalogenation of 5-iodouracil. Kim, B.D., Keenen, S., Bodnar, J.K., Sander, E.G. J. Biol. Chem. (1976) [Pubmed]
  9. Acid-base catalytic mechanism of dihydropyrimidinase from pH studies. Jahnke, K., Podschun, B., Schnackerz, K.D., Kautz, J., Cook, P.F. Biochemistry (1993) [Pubmed]
  10. Catalytic Mechanism of Escherichia coli Endonuclease VIII: Roles of the Intercalation Loop and the Zinc Finger. Kropachev, K.Y., Zharkov, D.O., Grollman, A.P. Biochemistry (2006) [Pubmed]
  11. Circadian rhythm of orotate phosphoribosyltransferase, pyrimidine nucleoside phosphorylases and dihydrouracil dehydrogenase in mouse liver. Possible relevance to chemotherapy with 5-fluoropyrimidines. Naguib, F.N., Soong, S.J., el Kouni, M.H. Biochem. Pharmacol. (1993) [Pubmed]
  12. Population and family studies of dihydropyrimidinuria: prevalence, inheritance mode, and risk of fluorouracil toxicity. Sumi, S., Imaeda, M., Kidouchi, K., Ohba, S., Hamajima, N., Kodama, K., Togari, H., Wada, Y. Am. J. Med. Genet. (1998) [Pubmed]
  13. Catabolism of deoxycytidine in human peripheral blood mononuclear cells and its interference with the determination of in situ thymidylate synthase activity. Arnér, E.S., Eriksson, S. Anal. Biochem. (1993) [Pubmed]
  14. Decline of nuclear and mitochondrial oxidative base excision repair activity in late passage human diploid fibroblasts. Shen, G.P., Galick, H., Inoue, M., Wallace, S.S. DNA Repair (Amst.) (2003) [Pubmed]
  15. Possible prediction of adverse reactions to pyrimidine chemotherapy from urinary pyrimidine levels and a case of asymptomatic adult dihydropyrimidinuria. Hayashi, K., Kidouchi, K., Sumi, S., Mizokami, M., Orito, E., Kumada, K., Ueda, R., Wada, Y. Clin. Cancer Res. (1996) [Pubmed]
  16. Transient conformational states of aminoacyl-tRNA during ribosome binding catalyzed by elongation factor Tu. Rodnina, M.V., Fricke, R., Wintermeyer, W. Biochemistry (1994) [Pubmed]
  17. Porcine recombinant dihydropyrimidine dehydrogenase: comparison of the spectroscopic and catalytic properties of the wild-type and C671A mutant enzymes. Rosenbaum, K., Jahnke, K., Curti, B., Hagen, W.R., Schnackerz, K.D., Vanoni, M.A. Biochemistry (1998) [Pubmed]
  18. A new class of contrast agents for MRI based on proton chemical exchange dependent saturation transfer (CEST). Ward, K.M., Aletras, A.H., Balaban, R.S. J. Magn. Reson. (2000) [Pubmed]
  19. Simple liquid chromatographic method for the determination of uracil and dihydrouracil plasma levels: a potential pretreatment predictor of 5-fluorouracil toxicity. Garg, M.B., Sevester, J.C., Sakoff, J.A., Ackland, S.P. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2002) [Pubmed]
  20. Mechanism-based inhibition of human leukocyte elastase and cathepsin G by substituted dihydrouracils. Groutas, W.C., Huang, H., Epp, J.B., Venkataraman, R., McClenahan, J.J., Tagusagawa, F. Biochim. Biophys. Acta (1994) [Pubmed]
  21. A possible role of Ku in mediating sequential repair of closely opposed lesions. Hashimoto, M., Donald, C.D., Yannone, S.M., Chen, D.J., Roy, R., Kow, Y.W. J. Biol. Chem. (2001) [Pubmed]
  22. Toxic death-case after capecitabine + oxaliplatin (XELOX) administration: probable implication of dihydropyrimidine deshydrogenase deficiency. Ciccolini, J., Mercier, C., Dahan, L., Evrard, A., Boyer, J.C., Richard, K., Dales, J.P., Durand, A., Milano, G., Seitz, J.F., Lacarelle, B. Cancer Chemother. Pharmacol. (2006) [Pubmed]
  23. Properties of D-hydantoinase from Agrobacterium tumefaciens and its use for the preparation of N-carbamyl D-amino acids. Durham, D.R., Weber, J.E. Biochem. Biophys. Res. Commun. (1995) [Pubmed]
  24. A gene cluster involved in pyrimidine reductive catabolism from Brevibacillus agri NCHU1002. Kao, C.H., Hsu, W.H. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  25. High-performance liquid chromatographic assay with UV detection for measurement of dihydrouracil/uracil ratio in plasma. Déporte, R., Amiand, M., Moreau, A., Charbonnel, C., Campion, L. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2006) [Pubmed]
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