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Chemical Compound Review:

PubChem9614 5-hydroxy-1H-pyrimidine-2,4- dione

Synonyms: SureCN48366, SureCN149516, AG-K-61288, SureCN4512381, CHEBI:29115, ...

Kreutzer, D.A. et al., Simon, P. et al., Tremblay, S. et al., Shirkey, B. et al., Kow, Y.W., et al.

Kow, Jaruga, Jaruga, Olczak, Halota, Olinski,

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Disease relevance of Isobarbituric acid

In an effort to determine the oxidized lesion(s) that gives rise to this mutation, the mutagenicity of three oxidized cytosines, 5-hydroxycytosine, 5-hydroxyuracil, and uracil glycol, were investigated in Escherichia coli [1].

High impact information on Isobarbituric acid

In the present study, we investigated the impact of the oxidative lesions 8-oxoguanine, thymine glycol and 5-hydroxyuracil on RNA polymerase II (RNA pol II) transcription using a well-defined in vitro transcription system [2].
Replication in vivo of the single-stranded genomes yielded mutation frequencies of 0.05%, 83%, and 80% for 5-hydroxycytosine, 5-hydroxyuracil, and uracil glycol, respectively [1].
Next, we report on the deamination of cytosine glycols to uracil glycols in oxidized DNA using acid hydrolysis and high performance liquid chromatography analysis with electrochemical detection to monitor 5-hydroxycytosine and 5-hydroxyuracil [3].
When cells are under oxidative stress that is induced either by oxidizing agents or by mitochondrial dysfunction, additional deamination products such as 5-hydroxymethyluracil (5-HMU) and 5-hydroxyuracil (5-OH-Ura) are formed [4].
5-Hydroxyuracil (5-OHU) in DNA, arising during endogenous DNA damage and caused by ionizing radiation, is removed by the base excision repair pathway [5].

Biological context of Isobarbituric acid

5-hydroxyuracil can form stable base pairs with all four bases in a DNA duplex [6].
Formation of isodialuric acid lesion within DNA oligomers via one-electron oxidation of 5-hydroxyuracil: characterization, stability and excision repair [7].

Anatomical context of Isobarbituric acid

Compared to OHUrd, 5-hydroxyuracil was much less cytotoxic for HT-29 cells [8].
DNA from 13 year desiccated cells did not show any higher levels of the commonly studied oxidatively modified DNA damage biomarkers 8-hydroxyguanine, 8-hydroxyadenine and 5-hydroxyuracil, compared to commercially available calf thymus DNA [9].

Associations of Isobarbituric acid with other chemical compounds

In the case of 5-hydroxyuracil and 8-hydroxyguanine, a statistically significant difference was also found between the control group and the asymptomatic HIV-positive patients [10].

Gene context of Isobarbituric acid

Ab initio base-pairing energies of uracil and 5-hydroxyuracil with standard DNA bases at the BSSE-free DFT and MP2 theory levels [11].

References

Oxidized, deaminated cytosines are a source of C --> T transitions in vivo. Kreutzer, D.A., Essigmann, J.M. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
RNA polymerase II bypass of oxidative DNA damage is regulated by transcription elongation factors. Charlet-Berguerand, N., Feuerhahn, S., Kong, S.E., Ziserman, H., Conaway, J.W., Conaway, R., Egly, J.M. EMBO J. (2006) [Pubmed]
2'-Deoxycytidine glycols, a missing link in the free radical-mediated oxidation of DNA. Tremblay, S., Douki, T., Cadet, J., Wagner, J.R. J. Biol. Chem. (1999) [Pubmed]
Repair of deaminated bases in DNA. Kow, Y.W. Free Radic. Biol. Med. (2002) [Pubmed]
NEIL1 Is the Major DNA Glycosylase that Processes 5-Hydroxyuracil in the Proximity of a DNA Single-Strand Break. Parsons, J.L., Kavli, B., Slupphaug, G., Dianov, G.L. Biochemistry (2007) [Pubmed]
5-hydroxyuracil can form stable base pairs with all four bases in a DNA duplex. Thiviyanathan, V., Somasunderam, A., Volk, D.E., Gorenstein, D.G. Chem. Commun. (Camb.) (2005) [Pubmed]
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]
Selective cytotoxicity of 5-hydroxyuridine for human colon adenocarcinoma cells. Lockshin, A., Giovanella, B.C., Mendoza, J.T., Warneke, C., Stehlin, J.S. Cancer treatment reports. (1985) [Pubmed]
Genomic DNA of Nostoc commune (Cyanobacteria) becomes covalently modified during long-term (decades) desiccation but is protected from oxidative damage and degradation. Shirkey, B., McMaster, N.J., Smith, S.C., Wright, D.J., Rodriguez, H., Jaruga, P., Birincioglu, M., Helm, R.F., Potts, M. Nucleic Acids Res. (2003) [Pubmed]
Oxidative DNA base damage in lymphocytes of HIV-infected drug users. Jaruga, P., Jaruga, B., Olczak, A., Halota, W., Olinski, R. Free Radic. Res. (1999) [Pubmed]
Ab initio base-pairing energies of uracil and 5-hydroxyuracil with standard DNA bases at the BSSE-free DFT and MP2 theory levels. Volk, D.E., Thiviyanathan, V., Somasunderam, A., Gorenstein, D.G. Org. Biomol. Chem. (2006) [Pubmed]

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