5-Bromouridine
 | |
| Names | |
|---|---|
| IUPAC name
5-Bromouridine | |
| Other names
5-Bromouracil ribonucleoside; 1-β-Ribofuranosyl-5-bromo-uracil; 5-Bromouridin | |
| Identifiers | |
| 957-75-5 | |
| 3D model (Jmol) | Interactive image |
| Abbreviations | BrUrd |
| ChemSpider | 82616 |
| ECHA InfoCard | 100.012.260 |
| PubChem | 91494 |
| |
| |
| Properties | |
| C9H11BrN2O6 | |
| Molar mass | 323.10 g·mol−1 |
| Appearance | Crystalline, white solid |
| Density | 2.043 g/cm3 |
| Melting point | 180 to 182 °C (356 to 360 °F; 453 to 455 K) (decomposes) |
| Chiral rotation ([α]D) |
[α]22/D −11°, c = 2 in H2O[1] |
| Hazards | |
| 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 [77 °F], 100 kPa). | |
| Infobox references | |
5-Bromouridine (BrUrd) is a uridine derivative with a bromo substituent at the fifth carbon.[2] 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.[3]
Uses
Antiviral activity
5-Bromouridine possesses anti-viral activity and inhibits the activity of viruses such as human immunodeficiency virus. It induces cell death and suppression the reproduction of cells[4]
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.[5]
Splicing of pre-mRNA
5-Bromouridine was also used to study in vitro slicing 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.[6]
See also
References
- ↑ 5-bromouridine in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2012)
- ↑ CSID:82616, http://www.chemspider.com/Chemical-Structure.82616.html (accessed 22:51, Oct 19, 2012)
- ↑ "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>
- ↑ Li, X; Patel, R; Melamed, MR; Darzynkiewicz, Z (1994). "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". Cell proliferation. 27 (6): 307–19. doi:10.1111/j.1365-2184.1994.tb01428.x. PMID 10465019.
- ↑ 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. PMID 22369889.
- ↑ 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. PMID 8072491.
External links
- CID {{{1}}} from PubChem
- 5-bromouridine in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2012)