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Chemical Compound Review

PubChem4063     5-iodo-1H-pyrimidine-2,4-dione

Synonyms: CHEMBL1173, SureCN7884, zlchem 530, PubChem21474, AG-G-10138, ...
 
 
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Disease relevance of NSC 57848

  • Lethal and mutagenic effects of 5-iodouracil on bacteriophage T4td8rII [1].
  • The 5-iodouracil 3 and the 5-ethyluracil 4 derivatives are highly selective TK-dependent inhibitors of HSV-1 and HSV-2 [2].
  • This study demonstrates the performance of four different MS-based strategies to characterize E. coli single-stranded DNA binding protein (SSB) that was UV-cross-linked to a 5-iodouracil containing DNA oligomer [3].
  • Complexes of 5-iodouracil (5IU) with Mn(II), Co(II), Cu(II), Zn(II), and Cd(II) ions have been prepared, characterized, and subjected to a screening system for evaluation of antitumor activity against Sarcoma-180 (S-180) and L 929 tumor cells [4].
  • When the synthesized compounds were examined for their activity against several viruses, including HIV-1, HSV-1, HSV-2 and HCMV, the 5-iodouracil analogue, 23, exhibited significant anti-HCMV activity [5].
 

High impact information on NSC 57848

  • Tissues were harvested and processed for gas chromatography-mass spectrometry analysis of the thymine, 5-bromouracil, and 5-iodouracil contents in hydrolyzed DNA [6].
  • A randomized RNA library substituted with the photoreactive chromophore 5-iodouracil was irradiated with monochromatic UV light in the presence of Rev. Those sequences with the ability to photocrosslink to Rev were partitioned from the rest of the RNA pool, amplified, and used for the next round of selection [7].
  • The three-dimensional structures of a binary complex with the inhibitor 5-iodouracil and two ternary complexes with NADPH and the inhibitors 5-iodouracil and uracil-4-acetic acid were determined by x-ray crystallography [8].
  • The N6-adenine DNA methyltransferases M.TaqI and M.CviBIII, which both methylate adenine within the double-stranded 5'-TCGA-3' DNA sequence, were photo-cross-linked to duplex oligodeoxyribonucleotides containing 5-iodouracil at the target position in 50-60% and almost quantitative yield, respectively [9].
  • Identification of the binding site for the extrahelical target base in N6-adenine DNA methyltransferases by photo-cross-linking with duplex oligodeoxyribonucleotides containing 5-iodouracil at the target position [9].
 

Biological context of NSC 57848

 

Associations of NSC 57848 with other chemical compounds

 

Gene context of NSC 57848

  • Inactivation of dihydropyrimidine dehydrogenase by 5-iodouracil [13].
  • 5-Iodouracil at 5.2 mM caused 212- (pH 5) and 100- (pH 7.4) FOLD INCREASES IN THE RATES OF PHOTOINACTIVATION OF THYMIDINE PHOSPHORYLASE [12].
  • To explore the structure-dependent hydrogen abstraction in antiparallel and parallel G-quartet DNA structures, the photochemical reactivity of 5-iodouracil ((I)U)-containing human telomeric DNA 22-mers was investigated under the 302 nm UV irradiation conditions [15].
  • A ssDNA oligo containing multiple 5-iodouracil residues (IdU) was cross-linked to RecA by irradiation with a XeC1 pulse laser (308 nm), and the cross-linked peptides were purified and sequenced [16].
 

Analytical, diagnostic and therapeutic context of NSC 57848

  • Since the IDU 5'-esters generated significantly higher levels of IDU in the brain, an HPLC analysis of IDU in the presence of 5'-esters and the metabolite 5-iodouracil was developed to characterize IDU uptake in the brain [17].
  • 5-Iodouracil (IUra)-substituted progeny bacteriophage T4td8 were grown under conditions such that, upon CsCl equilibrium isopycnic gradient centrifugation, progeny with density distributions about the median similar to that of unsubstituted phage are obtained [18].

References

  1. Lethal and mutagenic effects of 5-iodouracil on bacteriophage T4td8rII. Byrd, D.M., Prusoff, W.H. Antimicrob. Agents Chemother. (1977) [Pubmed]
  2. Synthesis, biological evaluation, and structure analysis of a series of new 1,5-anhydrohexitol nucleosides. Verheggen, I., Van Aerschot, A., Van Meervelt, L., Rozenski, J., Wiebe, L., Snoeck, R., Andrei, G., Balzarini, J., Claes, P., De Clercq, E. J. Med. Chem. (1995) [Pubmed]
  3. Mass spectrometric analysis of a UV-cross-linked protein-DNA complex: tryptophans 54 and 88 of E. coli SSB cross-link to DNA. Steen, H., Petersen, J., Mann, M., Jensen, O.N. Protein Sci. (2001) [Pubmed]
  4. Synthesis, characterization, and antitumor activity of 5-iodouracil complexes. Singh, U.P., Singh, B.N., Ghose, A.K., Singh, R.K., Sodhi, A. J. Inorg. Biochem. (1991) [Pubmed]
  5. Synthesis of novel 2'-methyl carbovir analogues as potent antiviral agents. Hong, J.H. Arch. Pharm. Res. (2007) [Pubmed]
  6. Biochemical modulation of 5-bromo-2'-deoxyuridine and 5-iodo-2'-deoxyuridine incorporation into DNA in VX2 tumor-bearing rabbits. Stetson, P.L., Normolle, D.P., Knol, J.A., Johnson, N.J., Yang, Z.M., Sakmar, E., Prieskorn, D., Terrio, P., Knutsen, C.A., Ensminger, W.D. J. Natl. Cancer Inst. (1991) [Pubmed]
  7. Using in vitro selection to direct the covalent attachment of human immunodeficiency virus type 1 Rev protein to high-affinity RNA ligands. Jensen, K.B., Atkinson, B.L., Willis, M.C., Koch, T.H., Gold, L. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  8. Crystal structure of the productive ternary complex of dihydropyrimidine dehydrogenase with NADPH and 5-iodouracil. Implications for mechanism of inhibition and electron transfer. Dobritzsch, D., Ricagno, S., Schneider, G., Schnackerz, K.D., Lindqvist, Y. J. Biol. Chem. (2002) [Pubmed]
  9. Identification of the binding site for the extrahelical target base in N6-adenine DNA methyltransferases by photo-cross-linking with duplex oligodeoxyribonucleotides containing 5-iodouracil at the target position. Holz, B., Dank, N., Eickhoff, J.E., Lipps, G., Krauss, G., Weinhold, E. J. Biol. Chem. (1999) [Pubmed]
  10. Noninvasive in vivo percutaneous absorption measurements using X-ray fluorescence. Robertson, J.D., Ferguson, E., Jay, M., Stalker, D.J. Pharm. Res. (1992) [Pubmed]
  11. Mechanism-based inactivation of dihydropyrimidine dehydrogenase by 5-ethynyluracil. Porter, D.J., Chestnut, W.G., Merrill, B.M., Spector, T. J. Biol. Chem. (1992) [Pubmed]
  12. Purification of thymidine phosphorylase from Escherichia coli and its photoinactivation in the presence of thymine, thymidine, and some halogenated analogs. Voytek, P. J. Biol. Chem. (1975) [Pubmed]
  13. Inactivation of dihydropyrimidine dehydrogenase by 5-iodouracil. Porter, D.J., Chestnut, W.G., Taylor, L.C., Merrill, B.M., Spector, T. J. Biol. Chem. (1991) [Pubmed]
  14. Chemical effects of iodine-125 decay in aqueous solution of 5-iodouracil. Ring fragmentation as a consequence of the Auger effect. Deutzmann, R., Stöcklin, G. Radiat. Res. (1981) [Pubmed]
  15. Highly efficient photochemical 2'-deoxyribonolactone formation at the diagonal loop of a 5-iodouracil-containing antiparallel G-quartet. Xu, Y., Sugiyama, H. J. Am. Chem. Soc. (2004) [Pubmed]
  16. Differential proximity probing of two DNA binding sites in the Escherichia coli recA protein using photo-cross-linking methods. Wang, Y., Adzuma, K. Biochemistry (1996) [Pubmed]
  17. Enhanced delivery of 5-iodo-2'-deoxyuridine to the brain parenchyma. Ghosh, M.K., Mitra, A.K. Pharm. Res. (1992) [Pubmed]
  18. The effect of 5-iodouracil on the growth and biosynthetic processes of bacteriophage T4td8 in the absence of light. Byrd, D.M., Prusoff, W.H. Chem. Biol. Interact. (1976) [Pubmed]
 
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