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D1916 Sigma-Aldrich

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

Synonym: 5,6-Dichlorobenzimidazole riboside, 5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole, DRB

  • CAS Number 53-85-0

  • Empirical Formula (Hill Notation) C12H12Cl2N2O4

  • Molecular Weight 319.14

  •  Beilstein/REAXYS Number 39123

  •  MDL number MFCD00036785

  •  eCl@ss 32151902

  •  PubChem Substance ID 24278361

  •  NACRES NA.77

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Properties

Related Categories Antitumor Agents, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cancer Research, Cell Biology,
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)

Description

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

Packaging

10 mg in poly bottle

50 mg in glass bottle

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.

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
DD7310000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Discover Bioactive Small Molecules for Gene Regulation

The loss of regulation of gene expression is a key component to many human disease states, including neurodegenerative disorders, autoimmune conditions and, most prominently, cancers. Regulation of g...
Keywords: Acetylations, Epigenetics, Gene expression, Genomics, Methylations, PAGE, Post translational modifications, Transcription

Peer-Reviewed Papers
15

References

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