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287891

5,6-Dichlorobenzimidazole 1-β-ᴅ-ribofuranoside

Name: 5,6-Dichlorobenzimidazole 1-β-ᴅ-ribofuranoside
Brand: MM

≥95% (HPLC), casein kinase II inhibitor, solid

Synonym(s):

5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole, 5,6-Dichlorobenzimidazole Riboside, DRB, Casein Kinase II Inhibitor VII

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₂Cl₂N₂O₄

CAS Number:

53-85-0

Molecular Weight:

319.14

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD00036785

eCl@ss:

32151902

Assay:

≥95% (HPLC)

Form:

solid

Storage condition:

OK to freeze

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Properties

Product Name

5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole, A potent, ATP-competitive, and specific inhibitor of casein kinase II (IC₅₀ = 6 µM).

Quality Segment

100

description

RTECS - DD7310000

assay

≥95% (HPLC)

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

Preparation Note

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

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c