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5-Bromouridine

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5-Bromouridine
Names
IUPAC name 5-Bromouridine
Systematic IUPAC name 1--5-bromoimidazole-2,4(1H,3H)-dione
Other names 5-Bromouracil ribonucleoside; 1-β-Ribofuranosyl-5-bromo-uracil; 5-Bromouridin
Identifiers
CAS Number
3D model (JSmol)
Abbreviations BrUrd
Beilstein Reference 33664
ChEBI
ChemSpider
ECHA InfoCard 100.012.260 Edit this at Wikidata
EC Number
  • 213-486-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H11BrN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1Key: AGFIRQJZCNVMCW-UAKXSSHOSA-N
  • InChI=1/C9H11BrN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1Key: AGFIRQJZCNVMCW-UAKXSSHOBS
SMILES
  • BrC=1C(=O)NC(=O)N(C=1)2O((O)2O)CO
Properties
Chemical formula C9H11BrN2O6
Molar mass 323.099 g·mol
Appearance Crystalline, white solid
Density 2.043 g/cm
Melting point 180 to 182 °C (356 to 360 °F; 453 to 455 K) (decomposes)
Chiral rotation (D) 22/D −11°, c = 2 in H2O
Hazards
Autoignition
temperature 		Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx), Hydrogen

bromide gas

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

5-Bromouridine (abbreviated BrUrd, 5BrU, br5Urd or rarely the one letter code B) is a uridine derivative with a bromo substituent at the fifth carbon. BrUrd is incorporated into RNA and can be detected immunocytochemically and analysed by cytometry. It causes DNA damage through base substitution and increases the number of mutations.

Uses

Detecting half-Life activity

5-Bromouridine has also been used to detect the half-life of RNA molecules. In a method called 5'-bromo-uridine immunoprecipitation chase-deep sequencing analysis (BRIC-seq), 5'-bromouridine is used to label RNA and enable the measurement of RNA levels over time. This method was used in Tani et al.'s study determining RNA half-lives to investigate the function of non-coding RNAs.

Splicing of pre-mRNA

5-Bromouridine was also used to study in vitro splicing of pre-mRNA in a study by Wansink. 5-Bromoruridine 5'-triphosphate (BruUTP) was used to label pre-mRNA and investigate the efficiency of splicing. They found that splicing is inhibited if uridines in RNA transcript were replaced by BrU, which suggested that Us were critical for the splicing reaction.

Detection of RNA synthesis in individual cells

Incorporation of 5-bromouridine by individual cells was detected immunocytochemically using antibodies against BrdU followed by flow cytometry.

See also

References

  1. 5-bromouridine in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2012)
  2. IUPAC-IUB Commission on Biochemical Nomenclature (1970). "Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents". Biochemistry. 9 (20): 4022–4027. doi:10.1021/bi00822a023.
  3. CSID:82616, http://www.chemspider.com/Chemical-Structure.82616.html (accessed 22:51, Oct 19, 2012)
  4. "5-bromouridine (CHEBI:20553)." EBI.ac.uk. European Bioinformatics Institute, 30 Nov. 2010. Web. 26 Oct. 2012.<http://www.ebi.ac.uk/chebi/advancedSearchFT.do;jsessionid=29B3462C81CE2E1F80223B50A927F832?chebiId=20553&structureSearchMethod=substructure>
  5. Tani, H; Mizutani, R; Salam, KA; Tano, K; Ijiri, K; Wakamatsu, A; Isogai, T; Suzuki, Y; Akimitsu, N (2012). "Genome-wide determination of RNA stability reveals hundreds of short-lived noncoding transcripts in mammals". Genome Research. 22 (5): 947–56. doi:10.1101/gr.130559.111. PMC 3337439. PMID 22369889.
  6. Wansink, DG; Nelissen, RL; De Jong, L (1994). "In vitro splicing of pre-mRNA containing bromouridine". Molecular Biology Reports. 19 (2): 109–13. doi:10.1007/BF00997156. hdl:11245/1.105890. PMID 8072491. S2CID 10367635.
  7. Larsen, J. K.; Jensen, P. Ø.; Larsen, J (2001). Flow cytometric analysis of RNA synthesis by detection of bromouridine incorporation. Vol. 12. pp. 7.12.1–7.12.11. doi:10.1002/0471142956.cy0712s12. ISBN 978-0471142959. PMID 18770724. S2CID 39703414. {{cite book}}: |journal= ignored (help)

External links

  • 5-bromouridine in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2012)
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