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Chemical Compound Review

Dihydrothymine     5-methyl-1,3-diazinane-2,4- dione

Synonyms: SureCN48294, AGN-PC-00BJBU, AG-G-71145, CHEBI:27468, HMDB00079, ...
 
 
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Disease relevance of NSC44131

  • The results showed that dihydrothymine in the template was at most a weak block to in vitro DNA synthesis catalyzed by Escherichia coli DNA polymerase I Klenow fragment (Pol I) and T4 DNA polymerase [1].
  • Whereas some compounds showed marked specificity for either TK-2 (i.e, the 5,6-dihydrothymine derivative, 26) or HSV-1 TK (i.e., the butynyl derivative, 11), some others, including the (Z)-and (E)-butenyl derivatives 10 and 12, showed significant inhibition against both enzymes [2].
 

High impact information on NSC44131

  • These proteins were tested for their efficiency to induce a single-strand break on a (32)P-labeled oligonucleotide containing either an abasic (AP) site, dihydrothymine (DHT), 7,8-dihydro-8-oxo-2'deoxyguanine, or 7, 8-dihydro-8-oxo-2'deoxyadenine at positions 1, 3, or 5 base pairs 5' or 3' to either an AP site or DHT on the labeled strand [3].
  • The S. kluyveri DHPase was capable of catalysing both dihydrouracil and dihydrothymine degradation, presumably by the same reaction mechanism as that described for mammalian DHPase [4].
  • Endonuclease III demonstrates two activities; as a glycosylase that removes saturated pyrimidine bases, such as dihydrothymine, and as an AP lyase that cleaves DNA strands at abasic sites [5].
  • Assays of the purified protein using oligonucleotide substrates unequivocally establish canonical APE activity, 3'-phosphatase and 3'-phosphodiesterase activities (in the context of a single-nucleotide gap), 3' --> 5' exonuclease activity (in the context of a nick), and nucleotide incision repair activity against 5,6-dihydrothymine [6].
  • A base damage (DHT and 8-oxoG) on the opposite strand has little or no influence on the rate of incision of an AP site by HAP1 [7].
 

Chemical compound and disease context of NSC44131

 

Biological context of NSC44131

 

Anatomical context of NSC44131

 

Associations of NSC44131 with other chemical compounds

  • A base damage (DHT, uracil, and 8-oxoG) on the opposite strand has little or no influence on the rate of excision of 8-oxoG whereas the presence of either an AP site or various types of single strand breaks has a strong inhibitory effect on the formation of a SSB due to the excision of 8-oxoG by both hOGG1 and the nuclear extract [14].
  • Ab initio theoretical study of the structures of thymine glycol and dihydrothymine [15].
  • Those from dihydro-1-methyluracil, dihydro-6-methyluracil, dihydro-1-ethyluracil and dihydro-1-methylcytosine exhibit a beta-nitrogen hyperfine coupling constant (alpha beta N) equal to or less than 2.0 G while the ones fom dihydro-orotic acid, dihydrouracil and dihydrothymine showed much larger alpha beta N values (greater than 3.3 G) [16].
 

Gene context of NSC44131

  • The ability of yeast OGG1 to excise 8-oxoG was determined when another type of damage [dihydrothymine, uracil, 8-oxoG, abasic (AP) site or various types of single-strand breaks (SSBs)] is present on the complementary strand 1, 3 or 5 bases 5' or 3' opposite to 8-oxoG [17].
  • To test this hypothesis, we have constructed model substrates containing damaged bases (5,6-dihydrothymine) or abasic sites set one, three, five and seven bases apart on opposite strands, and examined the reactivity of Escherichia coli endonuclease III towards these substrates [5].
  • In contrast, albeit some preference of UR, mNTH1 showed essentially comparable activities for all substrates including DHT [18].
 

Analytical, diagnostic and therapeutic context of NSC44131

  • By use of an ELISA assay, the antibodies produced were found to be specific for dihydrothymine [8].
  • Cell-free extracts from cells grown in the complex medium reduced the two bases to the dihydro compounds and decomposed dihydrothymine to beta-ureidoisobutyrate, as indicated by thin-layer chromatography [19].
  • Gas chromatography-mass spectrometry with high-performance liquid chromatography prepurification for monitoring the endonuclease III-mediated excision of 5-hydroxy-5,6-dihydrothymine and 5,6-dihydrothymine from gamma-irradiated DNA [20].

References

  1. Processing of DNA base damage by DNA polymerases. Dihydrothymine and beta-ureidoisobutyric acid as models for instructive and noninstructive lesions. Ide, H., Petrullo, L.A., Hatahet, Z., Wallace, S.S. J. Biol. Chem. (1991) [Pubmed]
  2. Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase. Hernández, A.I., Balzarini, J., Karlsson, A., Camarasa, M.J., Pérez-Pérez, M.J. J. Med. Chem. (2002) [Pubmed]
  3. Clustered DNA damage, influence on damage excision by XRS5 nuclear extracts and Escherichia coli Nth and Fpg proteins. David-Cordonnier, M.H., Laval, J., O'Neill, P. J. Biol. Chem. (2000) [Pubmed]
  4. PYD2 encodes 5,6-dihydropyrimidine amidohydrolase, which participates in a novel fungal catabolic pathway. Gojkovic, Z., Jahnke, K., Schnackerz, K.D., Piskur, J. J. Mol. Biol. (2000) [Pubmed]
  5. The action of Escherichia coli endonuclease III on multiply damaged sites in DNA. Chaudhry, M.A., Weinfeld, M. J. Mol. Biol. (1995) [Pubmed]
  6. Contributions of an endonuclease IV homologue to DNA repair in the African swine fever virus. Lamarche, B.J., Tsai, M.D. Biochemistry (2006) [Pubmed]
  7. Efficiency of incision of an AP site within clustered DNA damage by the major human AP endonuclease. David-Cordonnier, M.H., Cunniffe, S.M., Hickson, I.D., O'Neill, P. Biochemistry (2002) [Pubmed]
  8. Characterization of antibodies to dihydrothymine, a radiolysis product of DNA. Hubbard, K., Ide, H., Erlanger, B.F., Wallace, S.S. Biochemistry (1989) [Pubmed]
  9. Excision of 5,6-dihydroxy-5,6-dihydrothymine, 5,6-dihydrothymine, and 5-hydroxycytosine from defined sequence oligonucleotides by Escherichia coli endonuclease III and Fpg proteins: kinetic and mechanistic aspects. D'Ham, C., Romieu, A., Jaquinod, M., Gasparutto, D., Cadet, J. Biochemistry (1999) [Pubmed]
  10. Thymine ring saturation and fragmentation products: lesion bypass, misinsertion and implications for mutagenesis. Evans, J., Maccabee, M., Hatahet, Z., Courcelle, J., Bockrath, R., Ide, H., Wallace, S. Mutat. Res. (1993) [Pubmed]
  11. Absence of pyrimidine salvage and prevention of thymineless radiosensitization in Escherichia coli thyA cells fed dihydrothymine or thymine glycol. Claycamp, H.G., Smith, S.T. Radiat. Res. (1988) [Pubmed]
  12. Purification and characterization of an ATP-dependent amidohydrolase, N-methylhydantoin amidohydrolase, from Pseudomonas putida 77. Ogawa, J., Kim, J.M., Nirdnoy, W., Amano, Y., Yamada, H., Shimizu, S. Eur. J. Biochem. (1995) [Pubmed]
  13. Identification and tissue-specific expression of a NADH-dependent activity of dihydropyrimidine dehydrogenase in man. Van Kuilenburg, A.B., Van Lenthe, H., Van Gennip, A.H. Anticancer Res. (1996) [Pubmed]
  14. Efficiency of excision of 8-oxo-guanine within DNA clustered damage by XRS5 nuclear extracts and purified human OGG1 protein. David-Cordonnier, M.H., Boiteux, S., O'Neill, P. Biochemistry (2001) [Pubmed]
  15. Ab initio theoretical study of the structures of thymine glycol and dihydrothymine. Miaskiewicz, K., Miller, J., Osman, R. Int. J. Radiat. Biol. (1993) [Pubmed]
  16. E.s.r. and spin-trapping studies of dihydropyrimidines. gamma-Radiolysis in the polycrystalline state and U.V. photolysis in aqueous solution. Mossoba, M.M., Rosenthal, I., Riesz, P. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. (1981) [Pubmed]
  17. Excision of 8-oxoguanine within clustered damage by the yeast OGG1 protein. David-Cordonnier, M.H., Boiteux, S., O'Neill, P. Nucleic Acids Res. (2001) [Pubmed]
  18. Comparison of substrate specificities of Escherichia coli endonuclease III and its mouse homologue (mNTH1) using defined oligonucleotide substrates. Asagoshi, K., Odawara, H., Nakano, H., Miyano, T., Terato, H., Ohyama, Y., Seki, S., Ide, H. Biochemistry (2000) [Pubmed]
  19. Degradation of pyrimidine bases in Clostridium sticklandii. Schäfer, R., Schwartz, A.C. Arch. Microbiol. (1980) [Pubmed]
  20. Gas chromatography-mass spectrometry with high-performance liquid chromatography prepurification for monitoring the endonuclease III-mediated excision of 5-hydroxy-5,6-dihydrothymine and 5,6-dihydrothymine from gamma-irradiated DNA. D'Ham, C., Ravanat, J.L., Cadet, J. J. Chromatogr. B Biomed. Sci. Appl. (1998) [Pubmed]
 
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