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Chemical Compound Review

bromouridine     5-bromo-1-[(2R,3R,4S,5R)-3,4- dihydroxy-5...

Synonyms: SureCN41201, AG-K-90498, CHEMBL2206658, CHEBI:20553, ANW-40745, ...
 
 
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Disease relevance of NSC 38296

  • In the course of these investigations, it was found that Escherichia coli Ile-tRNA synthetase catalyzes cleavage of the glycosidic bond of 5-bromouridine [1].
  • An analogue of the replicase translational operator of bacteriophage R17, that contains a 5-bromouridine at position -5 (RNA 1), complexes with a dimer of the coat protein and photocrosslinks to the coat protein in high yield upon excitation at 308 nm with a xenon chloride excimer laser [2].
  • 5-Bromouridine (BrUrd) and several analogues of this antimetabolite exhibit antiviral activity and are potent inhibitors of the human immunodeficiency virus [3].
 

High impact information on NSC 38296

 

Biological context of NSC 38296

 

Anatomical context of NSC 38296

 

Gene context of NSC 38296

  • In vivo incorporation of 5-bromouridine, a marker of RNA synthesis, is also lower in olfactory neurons than in basal and supporting cells [11].
 

Analytical, diagnostic and therapeutic context of NSC 38296

  • Laser scanning confocal microscopy (LSCM) showed that P131 and P191 colocalized with neosynthesized 5-bromouridine 5'-triphosphate-labeled RNA and double-stranded RNA, demonstrating that they belong to the replication complex [12].
  • Nuclear RNA synthesis can be analysed by flow cytometry of cells labelled with 5-bromouridine (BrUrd) and stained with anti-bromodeoxyuridine (BrdUrd) antibody and FITC-conjugated secondary antibody [13].
  • Nascent RNA was labeled by incorporation of 5-bromouridine 5'-triphosphate, followed by pre-embedment or postembedment immunogold labeling and electron microscopy using ultrasmall gold-conjugated antibodies and silver enhancement [14].

References

  1. Aminoacyl-tRNA synthetase-catalyzed cleavage of the glycosidic bond of 5-halogenated uridines. Koontz, S.W., Schimmel, P.R. J. Biol. Chem. (1979) [Pubmed]
  2. An RNA-protein contact determined by 5-bromouridine substitution, photocrosslinking and sequencing. Willis, M.C., LeCuyer, K.A., Meisenheimer, K.M., Uhlenbeck, O.C., Koch, T.H. Nucleic Acids Res. (1994) [Pubmed]
  3. The cell cycle effects and induction of apoptosis by 5-bromouridine in cultures of human leukaemic MOLT-4 and HL-60 cell lines and mitogen-stimulated normal lymphocytes. Li, X., Patel, R., Melamed, M.R., Darzynkiewicz, Z. Cell Prolif. (1994) [Pubmed]
  4. Inhibition of pre-mRNA splicing by 5-fluoro-, 5-chloro-, and 5-bromouridine. Sierakowska, H., Shukla, R.R., Dominski, Z., Kole, R. J. Biol. Chem. (1989) [Pubmed]
  5. Prevention by nicotinamide of desensitization to thyrotropin stimulation in cultured human thyroid cells. Filetti, S., Takai, N.A., Rapoport, B. J. Biol. Chem. (1981) [Pubmed]
  6. Peanut clump virus RNA-1-encoded P15 regulates viral RNA accumulation but is not abundant at viral RNA replication sites. Dunoyer, P., Herzog, E., Hemmer, O., Ritzenthaler, C., Fritsch, C. J. Virol. (2001) [Pubmed]
  7. A specific, UV-induced RNA-protein cross-link using 5-bromouridine-substituted RNA. Gott, J.M., Willis, M.C., Koch, T.H., Uhlenbeck, O.C. Biochemistry (1991) [Pubmed]
  8. Electric field-mediated BrUTP uptake by mouse oocytes, eggs, and embryos. Waksmundzka, M., Debey, P. Mol. Reprod. Dev. (2001) [Pubmed]
  9. Reactions of 5-bromo substituted pyrimidine nucleosides with aqueous alkalies: kinetics and mechanisms. Käppi, R., Lönnberg, H. Acta Chem. Scand., B, Org. Chem. Biochem. (1986) [Pubmed]
  10. Non-isotopic detection of nucleolar transcription in pre-implantation mouse embryos. Koberna, K., Landa, V., Kanka, J., Pliss, A., Eltsov, M., Stanĕk, D., Raska, I. Reprod. Nutr. Dev. (1998) [Pubmed]
  11. Cell death in the olfactory epithelium. Magrassi, L., Graziadei, P.P. Anat. Embryol. (1995) [Pubmed]
  12. Intracellular localization of the peanut clump virus replication complex in tobacco BY-2 protoplasts containing green fluorescent protein-labeled endoplasmic reticulum or Golgi apparatus. Dunoyer, P., Ritzenthaler, C., Hemmer, O., Michler, P., Fritsch, C. J. Virol. (2002) [Pubmed]
  13. Flow cytometric measurement of RNA synthesis using bromouridine labelling and bromodeoxyuridine antibodies. Jensen, P.O., Larsen, J., Christiansen, J., Larsen, J.K. Cytometry. (1993) [Pubmed]
  14. Ultrastructural localization of active genes in nuclei of A431 cells. Wansink, D.G., Sibon, O.C., Cremers, F.F., van Driel, R., de Jong, L. J. Cell. Biochem. (1996) [Pubmed]
 
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