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D1916

Sigma-Aldrich

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

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Synonym(s):
5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole, 5,6-Dichlorobenzimidazole riboside, DRB
Empirical Formula (Hill Notation):
C12H12Cl2N2O4
CAS Number:
53-85-0
Molecular Weight:
319.14
Beilstein:
39123
MDL number:
MFCD00036785
eCl@ss:
32151902
PubChem Substance ID:
24278361
NACRES:
NA.77

form

powder

Quality Level

200

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3cc(Cl)c(Cl)cc23

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

Gene Information

human ... CSNK2A1(1457) , CSNK2B(1460)

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This Item
28789144687Z4775
5,6-Dichlorobenzimidazole 1-β-D-ribofuranoside

Sigma-Aldrich

D1916

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

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

Sigma-Aldrich

287891

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

5-Bromo-4-chloro-3-indolyl β-D-ribofuranoside ≥98.0% (HPLC)

Sigma-Aldrich

44687

5-Bromo-4-chloro-3-indolyl β-D-ribofuranoside

Zebularine ≥98% (HPLC), solid

Sigma-Aldrich

Z4775

Zebularine

storage temp.

−20°C

storage temp.

10-30°C

storage temp.

−20°C

storage temp.

2-8°C

Quality Level

200

Quality Level

100

Quality Level

-

Quality Level

-

Gene Information

human ... CSNK2A1(1457), CSNK2B(1460)

Gene Information

-

Gene Information

-

Gene Information

-

Application

5,6-Dichlorobenzimidazole 1-β-D-ribofuranoside has been used:
  • as an inhibitor of RNA polymerase II in mouse melanoma cells
  • for the inhibition of cyclin D1 mRNA synthesis in human prostate epithelial cell lines
  • in the inhibition of interleukin-2 gene transcription in Jurkat cells

Biochem/physiol Actions

5,6-Dichlorobenzimidazole 1-β-D-ribofuranoside (DRB), a nucleoside analog that halts mRNA synthesis by phosphorylation of the C-terminal domain of RNA polymerase II, making it inactive. It also interferes with the DNA topoisomerase II, may modulate response to cytokines and blocks the human immunodeficiency virus (HIV) via RNA modification. It also inhibits cyclin-dependent kinases (CDKs) 7 and 9 and favors apoptosis in leukemic cells. It may serve as a therapeutic agent in treating cancer.
Inhibitor of RNA synthesis; causes premature termination of transcription. CK2 (casein kinase-2) inhibitor.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Lisa Fish et al.
Genes & development, 30(4), 386-398 (2016-02-18)
Post-transcriptional deregulation is a defining feature of metastatic cancer. While many microRNAs have been implicated as regulators of metastatic progression, less is known about the roles and mechanisms of RNA-binding proteins in this process. We identified muscleblind-like 1 (MBNL1), a
Synthesis and biological evaluation of new 5, 6-dichlorobenzimidazole nucleoside derivatives
Gosselin G, et al.
Antiviral Chemistry & Chemotherapy, 5(4), 243-256 (1994)
The cyclin-dependent kinase inhibitor 5, 6-dichloro-1-beta-D-ribofuranosylbenzimidazole induces nongenotoxic, DNA replication-independent apoptosis of normal and leukemic cells, regardless of their p53 status
Turinetto V, et al.
BMC Cancer, 9(1), 281-281 (2009)
Transcriptional regulation of interleukin-2 gene expression is impaired by copper deficiency in Jurkat human T lymphocytes
Hopkins RG and Failla ML
The Journal of Nutrition, 129(3), 596-601 (1999)
Androgen receptor-mediated growth suppression of HPr-1AR and PC3-Lenti-AR prostate epithelial cells
Kim YC, et al.
PLoS ONE, 10(9), e0138286-e0138286 (2015)
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