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D1916

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

Name: 5,6-Dichlorobenzimidazole 1-β-<SC>D</SC>-ribofuranoside
Brand: SIGMA

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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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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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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)

Exploiting native forces to capture chromosome conformation in mammalian cell nuclei.

Lilija Brant et al.

Molecular systems biology, 12(12), 891-891 (2016-12-13)

Mammalian interphase chromosomes fold into a multitude of loops to fit the confines of cell nuclei, and looping is tightly linked to regulated function. Chromosome conformation capture (3C) technology has significantly advanced our understanding of this structure-to-function relationship. However, all

Inhibition of RNA polymerase II as a trigger for the p53 response.

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

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