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Merck

D1916

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
UNSPSC Code:
12352200
eCl@ss:
32151902
PubChem Substance ID:
24278361
NACRES:
NA.77
Beilstein/REAXYS Number:
39123
MDL number:
MFCD00036785
Form:
powder
Quality level:
200

Key Documents

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Product Name

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

Quality Level

200

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

form

powder

storage temp.

−20°C

Gene Information

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

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000420472
0000420472
0000420473
0000420473
0000394398

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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
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)
M Ljungman et al.
Oncogene, 18(3), 583-592 (1999-02-16)
The mechanisms by which the p53 response is triggered following exposure to DNA-damaging agents have not yet been clearly elucidated. We and others have previously suggested that blockage of RNA polymerase II may be the trigger for induction of the
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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We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

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Product Information Sheet - D1916

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