287891

5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole

A potent, ATP-competitive, and specific inhibitor of casein kinase II (IC₅₀ = 6 µM).

• Synonym(s): 5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole, 5,6-Dichlorobenzimidazole Riboside, DRB, Casein Kinase II Inhibitor VII
• Empirical Formula (Hill Notation): C₁₂H₁₂Cl₂N₂O₄
• CAS Number: 53-85-0
• Molecular Weight: 319.14
• MDL number: MFCD00036785
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• description: RTECS - DD7310000
• Assay: ≥98% (TLC)
• form: solid
• potency: 6 μM IC₅₀
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: DMSO: 3 mg/mL; ethanol: 3 mg/mL
• shipped in: ambient
• storage temp.: 10-30°C
• SMILES string: Clc1cc2[n](cnc2cc1Cl)[C@@H]3O[C@@H]([C@H]([C@H]3O)O)CO
• InChI: 1S/C12H12Cl2N2O4/c13-5-1-7-8(2-6(5)14)16(4-15-7)12-11(19)10(18)9(3-17)20-12/h1-2,4,9-12,17-19H,3H2/t9-,10-,11-,12-/m1/s1
• InChI key: XHSQDZXAVJRBMX-DDHJBXDOSA-N

Description

General description

A potent, ATP-competitive, and specific inhibitor of casein kinase II (IC₅₀ = 6 µM). Reported to inhibit insulin-stimulated nuclear and cytosolic p70S6 kinase in CHO cells. Accentuates premature termination of transcription. Has been used to inhibit RNA polymerase II transcription which may be dependent on casein kinase II. Inhibits germinal vesicle breakdown in bovine oocytes. Induces G₁/S cell cycle arrest.

Accentuates premature termination of transcription close to the promoter. Useful for isolation of RNA sequences near promoter sites that are responsible for mRNA formation. Useful for reversible superinduction of human fibroblast cultures. Potent, ATP-competivie and specific inhibitor of casein kinase II (IC₅₀ = 6 µM). Has been used to inhibit RNA polymerase II transcription, which may be dependent on casein kinase II. Inhibits germinal vesicle breakdown in bovine oocytes.

Biochem/physiol Actions

Cell permeable: no

Primary Target
casein kinase II

Product competes with ATP.

Reversible: no

Warning

Toxicity: Standard Handling (A)

Preparation Note

May require warming (47°C) to achieve complete dissolution.

Reconstitution

Room temperature (+20°C). Following reconstitution, aliquot and freeze (-20°C) for long term storage or refrigerate (4°C) for short term storage. Ethanol stock solutions are stable for up to 6 weeks at 4°C or for up to 3 months at -20°C.

Other Notes

Kim., S.J., and Kahn, C.R. 1997. Biochem. Biophys. Res. Commun. 234, 681.
Farin, C.E., and Yang, L. 1994. Mol. Reprod. Dev.37, 284.
Giardina, C., and Lis, J.T. 1993. J. Biol. Chem. 268, 23806.
Zandomeni, R., et al. 1986. J. Biol. Chem.261, 3414.
Mittleman, B., et al. 1983. J. Mol. Biol. 165, 461.
Zandomeni, R., et al. 1983. J. Mol. Biol. 167, 561.
Zandomeni, R., et al. 1982. Proc. Natl. Acad. Sci. USA79, 3167.
Stewart, M.W., et al. 1977. J. Gen. Virol.37, 221.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable