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Chemical Compound Review

ARABINOFURANOSYLURACIL     1-[3,4-dihydroxy-5- (hydroxymethyl)oxolan-2...

Synonyms: Uridine-5-d, Uridine 99%, TGBA01AD, ARONIS003790, SureCN2056758, ...
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Disease relevance of Arabinosyluracil

  • The specific activity of carbamoyl phosphate synthetase (glutamine-hydrolyzing), the first and rate-limiting enzyme of de novo uridine 5'-triphosphate biosynthesis, was increased in 13 transplantable hepatomas, particularly in the rapidly growing tumors (5.7- to 9.5-fold), and the rise was correlated with tumor growth rates [1].
  • The predicted amino acid sequence of a newly identified gene of the insect baculovirus Autographa californica nuclear polyhedrosis virus was similar to several uridine 5'-diphosphate (UDP)-glucuronosyl transferases and at least one UDP-glucosyl transferase [2].
  • Passage of E. coli RNA polymerase through an intrinsic transcription terminator, which encodes an RNA hairpin followed by a stretch of uridine residues, results in quick dissociation of the elongation complex [3].
  • Further studies should explore the role of oral uridine in the modulation of the toxicity of fluorouracil [4].
  • Incorporation of tritiated uridine into DNA of Ehrlich ascites tumor cells [5].

Psychiatry related information on Arabinosyluracil

  • Uridine (10 pmol) caused a mild but long-lasting increase in sleep, especially in paradoxical sleep [6].
  • When refluxed in water, the 2',3'-cyclic carbonates Ib, Id, and Ie are hydrolysed to the parent nucleosides, namely, uridine (Va; 81%), 5'-bromo-5'-deoxyuridine (Vb; 78%), and 5'-deoxyuridine (Vc; 83%) [7].
  • Oral uridine pro-drug PN401 is neuroprotective in the R6/2 and N171-82Q mouse models of Huntington's disease [8].
  • The response times for the utilization of uridine and thymidine following the removal of addition of Mg2+ are similar to those which follow removal or addition of serum [9].
  • In adult New Zealand white rabbits, the effects of food deprivation and of massive elevations of plasma uridine or thymidine concentrations on CSF and plasma nucleoside and oxypurine concentrations were studied [10].

High impact information on Arabinosyluracil

  • A common secondary folding motif for the snoRNAs and rRNA target segments predicts that site selection involves: (1) base pairing of the snoRNA with complementary rRNA elements flanking the site of modification, and (2) identification of a uridine located at a near-constant distance from the snoRNA ACA box [11].
  • The translational activation of several maternal mRNAs during Xenopus oocyte maturation is stimulated by cytoplasmic poly(A) elongation, which requires the uridine-rich cytoplasmic polyadenylation element (CPE) and the hexanucleotide AAUAAA [12].
  • RNA editing in the kinetoplastid Trypanosoma brucei results in the addition and deletion of uridine residues within several mitochondrial mRNAs [13].
  • Normal and LFS cells containing wild-type p53 arrested in G1 when challenged with the uridine biosynthesis inhibitor PALA and did not undergo PALA-selected gene amplification [14].
  • Uridine additions and deletions in the 5' ends of the COIII, MURF2, and MURF3 transcripts create new N-terminal amino acid sequences that are conserved between species, and new AUG initiation codons in several cases [15].

Chemical compound and disease context of Arabinosyluracil

  • Escherichia coli cells harboring the recombinant plasmid pMMG2 (galU) overproduced a protein that has been shown to correspond to a uridine 5'-triphosphate:glucose-1-phosphate uridylyltransferase (uridine diphosphoglucose [UDP-Glc] pyrophosphorylase) responsible for the synthesis of UDP-Glc, a key compound in the biosynthesis of polysaccharides [16].
  • In the present study we have examined the effect of hyperglycemia on the pathways of hepatic glycogenesis, estimated from liver uridine diphosphoglucose (UDPglucose) specific activities, and on peripheral (muscle) glucose metabolism in awake, unstressed control and 90% pancreatectomized, diabetic rats [17].
  • Euglycemic clamps were performed after prolonged hyperglycemia (18 mM, n = 10), or increased availability of either glucosamine (3 micromol/kg per min; n = 10) or uridine (30 micromol/kg per min; n = 4) [18].
  • Recognition of uridine diphosphate glucuronosyl transferases by LKM-3 antibodies in chronic hepatitis D [19].
  • Lymphoma cells from patients who responded had more glucocorticoid-receptor sites per cell and greater in-vitro sensitivity as measured by glucocorticoid inhibition of incorporation of leucine and uridine than did tumour cells from non-responders [20].

Biological context of Arabinosyluracil

  • The number of elongating form A and B RNA polymerases in chick oviduct nuclei was estimated by measuring incorportaion of 3H-UTP into 3' termini of nascent RNA chains in the presence of heparin to inhibit initiation, and quantitation labeled uridine released from these termini after alkaline hydrolysis [21].
  • Editing of kinetoplastid mitochondrial mRNAs by uridine addition and deletion generates conserved amino acid sequences and AUG initiation codons [15].
  • The first domain is formed by the sequence 5'-CUGA following stem I and is a sharp turn identical to the uridine turn of transfer RNA, whereas the second is a non-Watson-Crick three-base-pair duplex with a divalent-ion binding site [22].
  • Kinetoplastid RNA editing alters mitochondrial RNA transcripts by addition and deletion of uridine residues, producing open reading frames that may be twice as long as the original RNA [23].
  • Phosphorothioate oligodeoxynucleotides containing the C-5 propyne analogs of uridine and cytidine bind RNA with high affinity and are potent antisense inhibitors of gene expression [24].

Anatomical context of Arabinosyluracil

  • RNA editing is a novel type of mRNA processing in the kinetoplastid mitochondrion that involves the co- or posttranscriptional addition of uridine residues within transcripts [15].
  • Stimulation of uridine uptake in 3T3 cells in associated with increased ATP affinity of uridine-phosphorylating system [25].
  • The nucleotide uridine adenosine tetraphosphate (Up(4)A) was isolated from the supernatant of stimulated human endothelium and identified by mass spectrometry [26].
  • Cotton fiber membranes synthesize sitosterol-cellodextrins (SCDs) from SG and uridine 5'-diphosphate-glucose (UDP-Glc) under conditions that also favor cellulose synthesis [27].
  • These pulses produced different results from each other and from controls when transcription in dipteran salivary gland cells was monitored with tritiated uridine in transcription autoradiography, cytological nick translation, and analysis of isolated RNA fractions [28].

Associations of Arabinosyluracil with other chemical compounds


Gene context of Arabinosyluracil


Analytical, diagnostic and therapeutic context of Arabinosyluracil

  • Apoptosis (programmed cell death) was demonstrated by increased terminal deoxynucleotide transferase-mediated biotin uridine triphosphate nick-end labeling (TUNEL) staining in posttreatment biopsy specimens from 11 patients [39].
  • Effects of oral administrations of uridine were investigated in a study of six healthy volunteer control subjects and nine patients with metastatic colorectal cancer [4].
  • Uptake of [(3)H]gemcitabine and [(14)C] uridine was measured 3 days after microinjection to determine kinetic constants [40].
  • Affinity-purified antibodies eluted from recombinant proteins recognized a 64-kD nuclear protein in Western blotting and decorated the nucleoplasm in a speckled-network fashion in immunofluorescence, colocalizing with antibodies to pre-mRNA splicing factor SC35 and uridine-rich small nuclear RNAs [41].
  • To identify nucleotides in or near the active site, we have used a circularly permuted version of the VS ribozyme capable of cleavage and ligation to incorporate a single photoactive nucleotide analog, 4-thio- uridine, immediately downstream of the scissile bond [42].


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  2. A baculovirus blocks insect molting by producing ecdysteroid UDP-glucosyl transferase. O'Reilly, D.R., Miller, L.K. Science (1989) [Pubmed]
  3. Shortening of RNA:DNA hybrid in the elongation complex of RNA polymerase is a prerequisite for transcription termination. Komissarova, N., Becker, J., Solter, S., Kireeva, M., Kashlev, M. Mol. Cell (2002) [Pubmed]
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  5. Incorporation of tritiated uridine into DNA of Ehrlich ascites tumor cells. Yost, B.K., Rosenberg, M.J., Nishioka, D.J. J. Natl. Cancer Inst. (1976) [Pubmed]
  6. Differential sleep-promoting effects of five sleep substances nocturnally infused in unrestrained rats. Inoué, S., Honda, K., Komoda, Y., Uchizono, K., Ueno, R., Hayaishi, O. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
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  8. Oral uridine pro-drug PN401 is neuroprotective in the R6/2 and N171-82Q mouse models of Huntington's disease. Saydoff, J.A., Garcia, R.A., Browne, S.E., Liu, L., Sheng, J., Brenneman, D., Hu, Z., Cardin, S., Gonzalez, A., von Borstel, R.W., Gregorio, J., Burr, H., Beal, M.F. Neurobiol. Dis. (2006) [Pubmed]
  9. Magnesium deprivation reproduces the coordinate effects of serum removal or cortisol addition on transport and metabolism in chick embryo fibroblasts. Rubin, H. J. Cell. Physiol. (1976) [Pubmed]
  10. Nucleoside and oxypurine homeostasis in adult rabbit cerebrospinal fluid and plasma. Eells, J.T., Spector, R., Huntoon, S. J. Neurochem. (1984) [Pubmed]
  11. Small nucleolar RNAs direct site-specific synthesis of pseudouridine in ribosomal RNA. Ni, J., Tien, A.L., Fournier, M.J. Cell (1997) [Pubmed]
  12. CPEB is a specificity factor that mediates cytoplasmic polyadenylation during Xenopus oocyte maturation. Hake, L.E., Richter, J.D. Cell (1994) [Pubmed]
  13. Kinetoplastid RNA editing: in vitro formation of cytochrome b gRNA-mRNA chimeras from synthetic substrate RNAs. Harris, M.E., Hajduk, S.L. Cell (1992) [Pubmed]
  14. Wild-type p53 restores cell cycle control and inhibits gene amplification in cells with mutant p53 alleles. Yin, Y., Tainsky, M.A., Bischoff, F.Z., Strong, L.C., Wahl, G.M. Cell (1992) [Pubmed]
  15. Editing of kinetoplastid mitochondrial mRNAs by uridine addition and deletion generates conserved amino acid sequences and AUG initiation codons. Shaw, J.M., Feagin, J.E., Stuart, K., Simpson, L. Cell (1988) [Pubmed]
  16. Characterization of the galU gene of Streptococcus pneumoniae encoding a uridine diphosphoglucose pyrophosphorylase: a gene essential for capsular polysaccharide biosynthesis. Mollerach, M., López, R., García, E. J. Exp. Med. (1998) [Pubmed]
  17. Predominant role of gluconeogenesis in the hepatic glycogen repletion of diabetic rats. Giaccari, A., Rossetti, L. J. Clin. Invest. (1992) [Pubmed]
  18. Role of the glucosamine pathway in fat-induced insulin resistance. Hawkins, M., Barzilai, N., Liu, R., Hu, M., Chen, W., Rossetti, L. J. Clin. Invest. (1997) [Pubmed]
  19. Recognition of uridine diphosphate glucuronosyl transferases by LKM-3 antibodies in chronic hepatitis D. Philipp, T., Durazzo, M., Trautwein, C., Alex, B., Straub, P., Lamb, J.G., Johnson, E.F., Tukey, R.H., Manns, M.P. Lancet (1994) [Pubmed]
  20. In-vitro glucocorticoid studies for predicting response to glucocorticoid therapy in adults with malignant lymphoma. Bloomfield, C.D., Smith, K.A., Peterson, B.A., Hildebrandt, L., Zaleskas, J., Gajl-Peczalska, K.J., Frizzera, G., Munck, A. Lancet (1980) [Pubmed]
  21. Quantitation of elongating form A and B RNA polymerases in chick oviduct nuclei and effects of estradiol. Cox, R.F. Cell (1976) [Pubmed]
  22. Three-dimensional structure of a hammerhead ribozyme. Pley, H.W., Flaherty, K.M., McKay, D.B. Nature (1994) [Pubmed]
  23. RNA editing as a source of genetic variation. Landweber, L.F., Gilbert, W. Nature (1993) [Pubmed]
  24. Antisense gene inhibition by oligonucleotides containing C-5 propyne pyrimidines. Wagner, R.W., Matteucci, M.D., Lewis, J.G., Gutierrez, A.J., Moulds, C., Froehler, B.C. Science (1993) [Pubmed]
  25. Stimulation of uridine uptake in 3T3 cells in associated with increased ATP affinity of uridine-phosphorylating system. Goldenberg, G.J., Stein, W.D. Nature (1978) [Pubmed]
  26. Uridine adenosine tetraphosphate: a novel endothelium- derived vasoconstrictive factor. Jankowski, V., Tölle, M., Vanholder, R., Schönfelder, G., van der Giet, M., Henning, L., Schlüter, H., Paul, M., Zidek, W., Jankowski, J. Nat. Med. (2005) [Pubmed]
  27. Sitosterol-beta-glucoside as primer for cellulose synthesis in plants. Peng, L., Kawagoe, Y., Hogan, P., Delmer, D. Science (2002) [Pubmed]
  28. Pulsing electromagnetic fields induce cellular transcription. Goodman, R., Bassett, C.A., Henderson, A.S. Science (1983) [Pubmed]
  29. Chimeric gRNA-mRNA molecules with oligo(U) tails covalently linked at sites of RNA editing suggest that U addition occurs by transesterification. Blum, B., Sturm, N.R., Simpson, A.M., Simpson, L. Cell (1991) [Pubmed]
  30. RNA editing by cytidine insertion in mitochondria of Physarum polycephalum. Mahendran, R., Spottswood, M.R., Miller, D.L. Nature (1991) [Pubmed]
  31. Regulation of carbamoyl phosphate synthetase by MAP kinase. Graves, L.M., Guy, H.I., Kozlowski, P., Huang, M., Lazarowski, E., Pope, R.M., Collins, M.A., Dahlstrand, E.N., Earp, H.S., Evans, D.R. Nature (2000) [Pubmed]
  32. Pyrimidine salvage in Giardia lamblia. Aldritt, S.M., Tien, P., Wang, C.C. J. Exp. Med. (1985) [Pubmed]
  33. Carrier-mediated translocation of uridine diphosphate glucose into the lumen of endoplasmic reticulum-derived vesicles from rat liver. Vanstapel, F., Blanckaert, N. J. Clin. Invest. (1988) [Pubmed]
  34. Drosophila UNR is required for translational repression of male-specific lethal 2 mRNA during regulation of X-chromosome dosage compensation. Abaza, I., Coll, O., Patalano, S., Gebauer, F. Genes Dev. (2006) [Pubmed]
  35. A novel role for a U5 snRNP protein in 3' splice site selection. Umen, J.G., Guthrie, C. Genes Dev. (1995) [Pubmed]
  36. Targeted deletion of both thymidine phosphorylase and uridine phosphorylase and consequent disorders in mice. Haraguchi, M., Tsujimoto, H., Fukushima, M., Higuchi, I., Kuribayashi, H., Utsumi, H., Nakayama, A., Hashizume, Y., Hirato, J., Yoshida, H., Hara, H., Hamano, S., Kawaguchi, H., Furukawa, T., Miyazono, K., Ishikawa, F., Toyoshima, H., Kaname, T., Komatsu, M., Chen, Z.S., Gotanda, T., Tachiwada, T., Sumizawa, T., Miyadera, K., Osame, M., Yoshida, H., Noda, T., Yamada, Y., Akiyama, S. Mol. Cell. Biol. (2002) [Pubmed]
  37. HuR, a RNA stability factor, is expressed in malignant brain tumors and binds to adenine- and uridine-rich elements within the 3' untranslated regions of cytokine and angiogenic factor mRNAs. Nabors, L.B., Gillespie, G.Y., Harkins, L., King, P.H. Cancer Res. (2001) [Pubmed]
  38. Parenchymal cell apoptosis as a signal for sinusoidal sequestration and transendothelial migration of neutrophils in murine models of endotoxin and Fas-antibody-induced liver injury. Lawson, J.A., Fisher, M.A., Simmons, C.A., Farhood, A., Jaeschke, H. Hepatology (1998) [Pubmed]
  39. Adenovirus-mediated p53 gene transfer in advanced non-small-cell lung cancer. Swisher, S.G., Roth, J.A., Nemunaitis, J., Lawrence, D.D., Kemp, B.L., Carrasco, C.H., Connors, D.G., El-Naggar, A.K., Fossella, F., Glisson, B.S., Hong, W.K., Khuri, F.R., Kurie, J.M., Lee, J.J., Lee, J.S., Mack, M., Merritt, J.A., Nguyen, D.M., Nesbitt, J.C., Perez-Soler, R., Pisters, K.M., Putnam, J.B., Richli, W.R., Savin, M., Schrump, D.S., Shin, D.M., Shulkin, A., Walsh, G.L., Wait, J., Weill, D., Waugh, M.K. J. Natl. Cancer Inst. (1999) [Pubmed]
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  42. 4-thio-U cross-linking identifies the active site of the VS ribozyme. Hiley, S.L., Sood, V.D., Fan, J., Collins, R.A. EMBO J. (2002) [Pubmed]
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