5-Bromouridine

• CAT Number: R017876
• CAS Number: 957-75-5
• Molecular Formula: C9H11BrN2O6
• Molecular Weight: 323.099
• Purity: ≥95%
• Synonyms: (-)-5-Bromouridine; NSC 38296
• Target: Nucleoside Antimetabolite/Analog
• Storage: -20°C
• IUPAC Name: 5-bromo-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• 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/s1
• InChIKey: AGFIRQJZCNVMCW-UAKXSSHOSA-N
• SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)Br

5-Bromouridine (CAS 957-75-5)  is a brominated analog of the nucleoside uridine. It can be incorporated into RNA and subsequently detected by antibodies against bromodeoxyuridine. 5-Bromouridine decreases the viability of HL-60 and MOLT-4 cells (LC50s = 10 and 20 μM, respectively). It induces apoptosis and halts the cell cycle at the S phase in HL-60 cells. It is photoreactive, and UV irradiation has been used to cross-link RNA containing 5-bromouridine to proteins in the study of of RNA-protein interactions. 5-Bromouridine can also be incorporated into RNA using 5-bromouridine 5’-triphosphate.

Reference

1.Tanner, N. Kyle, Michelle M. Hanna, and John Abelson. "Binding interactions between yeast tRNA ligase and a precursor transfer ribonucleic acid containing two photoreactive uridine analogs." Biochemistry 27.24 (1988): 8852-8861.
2.Li, X., et al. "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 (1994): 307-319.
3.Gott, Jonatha M., et al. "A specific, UV-induced RNA-protein crosslink using 5-bromouridine-substituted RNA." Biochemistry 30.25 (1991): 6290-6295.