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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

Key Documents

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Product Name

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

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

Quality Level

200

Gene Information

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

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Biochem/physiol Actions

Inhibitor of RNA synthesis; causes premature termination of transcription. CK2 (casein kinase-2) inhibitor.
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.

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

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
109M4056V
13181127
059M4126V
078M4045V
068M4041V

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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)
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)
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
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