:5-Bromouridine
{{Educational assignment}}
{{Chembox
| ImageFile = 5-Bromouridine Haworth.svg
| ImageSize =
| ImageAlt =
| IUPACName = 5-Bromouridine
| SystematicName = 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-bromoimidazole-2,4(1H,3H)-dione
| OtherNames = 5-Bromouracil ribonucleoside; 1-β-Ribofuranosyl-5-bromo-uracil; 5-Bromouridin
|Section1={{Chembox Identifiers
| Abbreviations = BrUrd
| CASNo = 957-75-5
| Beilstein = 33664
| ChEBI = 20553
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KEY8PG1BRC
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 91494
| ChemSpiderID = 82616
| EC_number = 213-486-6
| 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/s1
| InChIKey = AGFIRQJZCNVMCW-UAKXSSHOBS
| StdInChI = 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/s1
| StdInChIKey = AGFIRQJZCNVMCW-UAKXSSHOSA-N
| SMILES = BrC=1C(=O)NC(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO}}
|Section2={{Chembox Properties
| C=9 | H=11 | Br=1 | N=2 | O=6
| Appearance = Crystalline, white solid
| Density = 2.043 g/cm3
| MeltingPtC = 180 to 182
| MeltingPt_notes = (decomposes)
| BoilingPt =
| SpecRotation = [α]22/D −11°, c = 2 in H2O{{nist |name=5-bromouridine |id=C957755 |accessdate=2012 |mask=3EFF |units=SI}}
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx), Hydrogen
bromide gas}}
}}
5-Bromouridine (abbreviated BrUrd, 5BrU, br5Urd or rarely the one letter code B){{Cite journal | author = IUPAC-IUB Commission on Biochemical Nomenclature | doi = 10.1021/bi00822a023 | title = Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents | journal = Biochemistry | volume = 9 | issue = 20 | pages = 4022–4027 | year = 1970 }} is a uridine derivative with a bromo substituent at the fifth carbon.CSID:82616, http://www.chemspider.com/Chemical-Structure.82616.html (accessed 22:51, Oct 19, 2012) 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."5-bromouridine (CHEBI:20553)." EBI.ac.uk. European Bioinformatics Institute, 30 Nov. 2010. Web. 26 Oct. 2012.
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.{{cite journal |pmid=22369889 |year=2012 |last1=Tani |first1=H |last2=Mizutani |first2=R |last3=Salam |first3=KA |last4=Tano |first4=K |last5=Ijiri |first5=K |last6=Wakamatsu |first6=A |last7=Isogai |first7=T |last8=Suzuki |first8=Y |last9=Akimitsu |first9=N |title=Genome-wide determination of RNA stability reveals hundreds of short-lived noncoding transcripts in mammals |volume=22 |issue=5 |pages=947–56 |journal=Genome Research |doi=10.1101/gr.130559.111 |pmc=3337439}}
=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.{{cite journal |pmid=8072491 |year=1994 |last1=Wansink |first1=DG |last2=Nelissen |first2=RL |last3=De Jong |first3=L |title=In vitro splicing of pre-mRNA containing bromouridine |volume=19 |issue=2 |pages=109–13 |journal=Molecular Biology Reports |doi=10.1007/BF00997156 |hdl=11245/1.105890|s2cid=10367635 |url=http://dare.uva.nl/personal/pure/en/publications/in-vitro-splicing-of-premrna-containing-bromouridine(4a6fe695-ad7c-4344-896a-8d6837c63505).html |url-access=subscription }}
=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.{{Cite book | pmid = 18770724| year = 2001| last1 = Larsen| first1 = J. K.| last2 = Jensen| first2 = P. Ø.| title = Flow cytometric analysis of RNA synthesis by detection of bromouridine incorporation| journal = Current Protocols in Cytometry| volume = 12|issue=7.12| pages = 7.12.1–7.12.11| last3 = Larsen| first3 = J| doi = 10.1002/0471142956.cy0712s12| isbn = 978-0471142959| s2cid = 39703414}}
See also
References
{{Reflist|2}}
External links
- {{nist |name=5-bromouridine |id=C957755 |accessdate=2012 |mask=3EFF |units=SI}}
{{DEFAULTSORT:Bromouridine, 5-}}