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D1916

Sigma-Aldrich

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

≥98% (HPLC), powder, RNA synthesis inhibitor

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H12Cl2N2O4
CAS Number:
53-85-0
Molecular Weight:
319.14
Beilstein:
39123
MDL number:
MFCD00036785
UNSPSC Code:
12352200
eCl@ss:
32151902
PubChem Substance ID:
24278361
NACRES:
NA.77

product name

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

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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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Rates of in situ transcription and splicing in large human genes
Singh J and Padgett RA
Nature Structural and Molecular Biology, 16(11), 1128-1128 (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)
NELF, a multisubunit complex containing RD, cooperates with DSIF to repress RNA polymerase II elongation
Yamaguchi Y, et al.
Cell, 97(1), 41-51 (1999)
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