Bromotubercidin

• CAT Number: I023730
• CAS Number: 21193-80-6
• Molecular Formula: C11H13BrN4O4
• Molecular Weight: 345.153
• Purity: 98%
• Synonyms: 5-Bromotubericidin; NSC103802; NSC 103802; NSC-103802
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 7H-Pyrrolo(2,3-d)pyrimidin-4-amine, 5-bromo-7-beta-D-ribofuranosyl-
• InChI: InChI=1S/C11H13BrN4O4/c12-4-1-16(10-6(4)9(13)14-3-15-10)11-8(19)7(18)5(2-17)20-11/h1,3,5,7-8,11,17-19H,2H2,(H2,13,14,15)/t5-,7-,8-,11-/m1/s1
• InChIKey: ZWTPRQXZXQEKFT-IOSLPCCCSA-N
• SMILES: NC1=C2C(N([C@H]3[C@@H]([C@@H]([C@@H](CO)O3)O)O)C=C2Br)=NC=N1

Bromotubercidin (CAT: I023730) is a reversible inhibitor of RNA synthesis, exerting its action by impeding the process of RNA biosynthesis. This compound’s interaction with the RNA synthesis machinery interferes with the normal progression of transcription, ultimately leading to a reduction in the production of RNA molecules. By targeting this essential cellular process, Bromotubercidin exhibits the ability to modulate gene expression and cellular functions reliant on proper RNA synthesis.

Reference

1: Brdar B, Reich E. Biochemical and biological properties of 5-bromotubercidin: differential effects on cellular DNA-directed and viral RNA-directed RNA synthesis. Bioorg Med Chem. 2008 Feb 1;16(3):1481-92. doi: 10.1016/j.bmc.2007.10.054. Epub 2007 Oct 22. PMID: 17977728.
2: Bergstrom DE, Brattesani AJ. Halogenation of tubercidin by N-halosuccinimides. A direct route to 5-bromotubercidin, a reversible inhibitor of RNA synthesis in eukaryotic cells. Nucleic Acids Res. 1980 Dec 20;8(24):6213-9. doi: 10.1093/nar/8.24.6213. PMID: 6162160; PMCID: PMC328083.
3: Pearson D, Shainberg A, Malamed S, Sachs H. The hypothalamo-neurohypophysial complex in organ culture: effects of metabolic inhibitors, biologic and pharmacologic agents. Endocrinology. 1975 Apr;96(4):994-1003. doi: 10.1210/endo-96-4-994. PMID: 164341.
4: Brdar B, Reich E. Selective irreversible inactivation of replicating mengovirus by nucleoside analogues: a new form of viral interference. J Virol. 1999 Aug;73(8):6444-52. doi: 10.1128/JVI.73.8.6444-6452.1999. PMID: 10400738; PMCID: PMC112725.