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D1916

Sigma-Aldrich

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

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

form

powder

Quality Level

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

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Application

5,6-Dichlorobenzimidazole 1-β-D-ribofuranoside has been used:
  • as an inhibitor of RNA polymerase II in mouse melanoma cells[1]
  • for the inhibition of cyclin D1 mRNA synthesis in human prostate epithelial cell lines[2]
  • in the inhibition of interleukin-2 gene transcription in Jurkat cells[3]

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[4] by phosphorylation of the C-terminal domain of RNA polymerase II, making it inactive.[5] It also interferes with the DNA topoisomerase II, may modulate response to cytokines and blocks the human immunodeficiency virus (HIV) via RNA modification.[6] 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.[7]
Inhibitor of RNA synthesis; causes premature termination of transcription. CK2 (casein kinase-2) inhibitor.

Features and Benefits

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Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Origin

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Product Information Sheet

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