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Antiretroviral drug
5-Bromouridine
Другие языки:

    5-Bromouridine

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    5-Bromouridine
    5-Bromouridine Haworth.svg
    Names
    IUPAC name
    5-Bromouridine
    Systematic IUPAC name
    1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-bromoimidazole-2,4(1H,3H)-dione
    Other names
    5-Bromouracil ribonucleoside; 1-β-Ribofuranosyl-5-bromo-uracil; 5-Bromouridin
    Identifiers
    3D model (JSmol)
    Abbreviations BrUrd
    33664
    ChEBI
    ChemSpider
    ECHA InfoCard 100.012.260
    EC Number
    • 213-486-6
    PubChem CID
    UNII
    • 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/s1
      Key: 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/s1
      Key: AGFIRQJZCNVMCW-UAKXSSHOBS
    • BrC=1C(=O)NC(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
    Properties
    C9H11BrN2O6
    Molar mass 323.099 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)
    [α]22/D −11°, c = 2 in H2O
    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).

    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

    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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