ChemicalBook > CAS DataBase List > DRB

DRB

Product Name
DRB
CAS No.
53-85-0
Chemical Name
DRB
Synonyms
DRB;DBR;NSC 401575;DRB USP/EP/BP;DRB (Benzimidazole);dichlororibofuranosylbenzimidazole;5,6-DICHLOROBENZIMIDAZOLE RIBOSIDE;Dichlorobenzimidazoleribofuranoside;5,6-dichloro-1-β-D-ribobenzimidazole;5,6-dichlorobenzimidazoleriboside(drb)
CBNumber
CB0367110
Molecular Formula
C12H12Cl2N2O4
Formula Weight
319.14
MOL File
53-85-0.mol
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DRB Property

Melting point:
222-224°C
Boiling point:
606.2±65.0 °C(Predicted)
Density 
1.5917 (rough estimate)
refractive index 
1.6200 (estimate)
storage temp. 
-20°C
solubility 
Soluble in DMSO (up to 20 mg/ml)
pka
13.23±0.70(Predicted)
form 
White solid
color 
White
Water Solubility 
Soluble in DMSO to 75mMSoluble in dimethyl sulfoxide, hot ethanol, dimethyl formamide, (1:2) dimethyl formamide:Phosphate buffer saline, water, methanol and pyridine. Slightly soluble in aqueous buffers.
λmax
296nm(lit.)
BRN 
39123
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKey
XHSQDZXAVJRBMX-AYLPWXGPSA-N
CAS DataBase Reference
53-85-0
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Safety

Safety Statements 
24/25
WGK Germany 
3
RTECS 
DD7310000
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D1916
Product name
5,6-Dichlorobenzimidazole 1-β-D-ribofuranoside
Packaging
10mg
Price
$66.2
Updated
2024/03/01
Sigma-Aldrich
Product number
287891
Product name
5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole
Packaging
50mg
Price
$172
Updated
2024/03/01
TCI Chemical
Product number
D4292
Product name
5,6-Dichlorobenzimidazole 1-beta-D-Ribofuranoside
Purity
>98.0%(HPLC)(N)
Packaging
1g
Price
$988
Updated
2024/03/01
TCI Chemical
Product number
D4292
Product name
5,6-Dichlorobenzimidazole 1-beta-D-Ribofuranoside
Purity
>98.0%(HPLC)(N)
Packaging
100mg
Price
$168
Updated
2024/03/01
Alfa Aesar
Product number
J64870
Product name
5,6-Dichlorobenzimidazole riboside, 98%
Packaging
50mg
Price
$174
Updated
2024/03/01
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DRB Chemical Properties,Usage,Production

Description

DRB (53-85-0) is a classic inhibitor of transcription by RNA polymerase II.?A relatively selective inhibitor of Cdk9 (IC50=3 μM), the kinase of the positive transcription elongation factor b (P-TEF-b) required for processive transcription elongation by RNA polymerase II.1,2?Also inhibits casein kinase II, IC50=4-10 μM.?3?Suppresses the SIRT1/CK2α pathway and enhances the radiosensitivity of human cancer cells.4?Kinase-independent activities of Cdk9 such as glucocorticoid receptor modulation are not inhibited by DRB.5

Chemical Properties

White Solid

Uses

Inhibits casein kinase II and blocks RNA synthesis. An adenosine analog.5,6-Dichlorobenzimidazole riboside is used as an inhibitor of RNA Polymerase II. It is nucleoside analogue and used in research to study the mechanisms of cellular regulation. Further, it inhibits some protein kinases.

Uses

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

Uses

DRB is an inhibitor of RNA synthesis (causes premature termination of transcription).

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.

References

1) Baumli?et al.?(2010),?Halogen bonds form the basis for selective P-TEFb inhibition by DRB; Chem. Biol.,?17?931 2) Yamaguchi?et al.?(1998),?Interplay between positive and negative elongation factors: drawing a new view of DRB; Genes Cells,?3?9 3) Zandomeni (1989), Kinetics of inhibition by 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole; Biochem.J., 262 469 4) Wang?et al.?(2014),?Inhibition of P-TEFb by DRB suppresses SIRT1/CK2α pathway and enhances radiosensitivity of human cancer cells; Anticancer Res.,?34?6981 5) Zhu?et al.?(2014),?A kinase-independent activity of Cdk9 modulates glucocorticoid receptor-mediated gene induction; Biochemistry,?53?1753

DRB Preparation Products And Raw materials

Raw materials

Preparation Products

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DRB Suppliers

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53-85-0, DRBRelated Search:

N-Ethylbenzimidazole DRB Cibanone Black DRB 6-CHLORO-1H-BENZIMIDAZOLE 1-METHYLBENZIMIDAZOLE 5,6-DICHLOROBENZIMIDAZOLE 5,6-DICHLORO-1-BETA-D-RIBOFURANOSYLBENZIMIDAZOLE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT (S)-3-AMINO-1,2-DIHYDROXYPROPANE HYDROCHLORIDE 1-HYDROXYMETHYLBENZIMIDAZOLE BASIONIC(TM) AC 75 1H-Benzimidazole,1-propyl-(9CI) N-ETHYL-5,6-DICHLOROBENZIMIDAZOLE HLA-DRB1 5,6-DICHLOROBENZIMIDAZOLE SP-5,6-DCI-CBIMPS BoLA-DRB3 antigen HLA-DRB5 HLA DRB4*01033

  • 5,6-DICHLOROPURINE-1-BETA-D-RIBOFURANOSYL-H-BENZIMIDAZOLE
  • 5,6-DICHLORO-1-BETA-D-RIBOFURANOSYLBENZIMIDAZOLE
  • 5,6-dichloro-1-beta-d-ribofuranosyl-benzimidazol
  • 5,6-dichlorobenzimidazoleriboside(drb)
  • Dichlorobenzimidazoleribofuranoside
  • dichlororibofuranosylbenzimidazole
  • 5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole - CAS 53-85-0 - Calbiochem
  • 5,6-Dichloro-1-b-D-ribofuranosylbenzimidazole
  • 5,6-Dichloropurine-1-b-D-ribofuanosyl-H-benzimidazole
  • DBR,5,6-Dichlorobenzimidazole1-b-D-ribofuranoside
  • 5,6-dichloro-1-β-d-ribofuranosylbenzimidazole
  • 5,6-dichlorobenzimidazole 1-β-d-ribofuranoside
  • 5,6-Dichlorobenzimidazole-1-b-D-ribofuranoside
  • 5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole, 5,6-Dichlorobenzimidazole riboside, DRB
  • 5,6-DICHLOROBENZIMIDAZOLE RIBOSIDE 98%
  • 5,6-DICHLOROBENZIMIDAZOLE RIBOSIDE (DRB)98%
  • 5,6-Dichloropurine-1--D-ribofuanosyl-H-benzimidazole
  • DBR, 5,6-Dichlorobenzimidazole 1--D-ribofuranoside
  • 5,6-Dichlorobenzimidazole-1-β-D-ribofuranoside ,98%
  • 1-β-D-Ribofuranosyl-5,6-dichlorobenziMidazole
  • NSC 401575
  • 4,5-dichloro-2-(3-methylbenzyl)pyridazin-3(2h)-one
  • 5,6-DICHLOROBENZIMIDAZOLE-1-BETA-D-RIBOFURANOSIDE
  • 5,6-DICHLOROBENZIMIDAZOLE RIBOSIDE
  • 5,6-DICHLORO-BETA-D-RIBOFURANOSYL-BENZIMIDAZOLE
  • DRB (Benzimidazole)
  • DRB
  • DBR
  • 5,6-Dichlororibofuranosylbenzimidazole
  • 5,6-Dichlorobenzimidazole1-β-D-Ribofuranoside&gt
  • 5,6-Dichloro-1-(beta-D-ribofuranosyl)-1H-benzimidazole
  • 1H-Benzimidazole, 5,6-dichloro-1-β-D-ribofuranosyl-
  • 5,6-Dichloropurine-1-β-D-ribofuanosyl-H-benzimidazole
  • DRB USP/EP/BP
  • (2R,3R,4S,5R)-2-(5,6-Dichloro-1H-benzo[d]imidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
  • 5,6-DICHLOROBENIMIDAZOLE-1-B-D- RIBOFURANOSIDE
  • 5,6-Dichlorobenzimidazole 1-β-D-Ribofuranoside
  • 5,6-Dichlorobenzimidazole riboside,DRB,inhibit,Inhibitor,CDK,Cyclin dependent kinase
  • 5,6-Dichlorobenzimidazole riboside(DBR)
  • 1H-Benzimidazole,5,6-dichloro-1-b-D-ribofuranosyl-
  • 5,6-dichloro-1-β-D-ribobenzimidazole
  • ,6-Dichlorobenzimidazole 1-β-D-Ribofuranoside
  • 53-85-0
  • C12H12Cl2N2O4
  • DNA-RNA Transcription Regulators
  • Gene Regulation and Expression
  • Monosaccharides
  • Specialty Synthesis
  • BioChemical
  • Cell Biology
  • Carbohydrate Synthesis
  • Cell Signaling and Neuroscience
  • Bases & Related Reagents
  • Inhibitors
  • Nucleotides