53-85-0

Basic information

• Product Name: DRB
• Synonyms: 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-b-D-ribofuranosylbenzimidazole;5,6-Dichloropurine-1-b-D-ribofuanosyl-H-benzimidazole
• CAS NO: 53-85-0
• Molecular Formula: C₁₂H₁₂Cl₂N₂O₄
• Molecular Weight: 319.14
• Product Categories: Bases & Related Reagents;Inhibitors;Nucleotides
• Mol File: 53-85-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 222-224°C
• Boiling Point: 606.2 °C at 760 mmHg
• Flash Point: 320.4 °C
• Appearance: White to off-white crystalline solid.
• Density: 1.5917 (rough estimate)
• Vapor Pressure: 1.51E-15mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO (up to 20 mg/ml)
• PKA: 13.23±0.70(Predicted)
• Water Solubility: Soluble in DMSO to 75mMSoluble in dimethyl sulfoxide, hot ethanol, dimethyl formamide, (1:2) dimethyl formamide:Phosphate buffer
• 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.
• BRN: 39123
• CAS DataBase Reference: DRB(CAS DataBase Reference)
• NIST Chemistry Reference: DRB(53-85-0)
• EPA Substance Registry System: DRB(53-85-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: DD7310000
• Hazardous Substances Data: 53-85-0(Hazardous Substances Data)

Usage

Description

5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole, also known as DRB, is a nucleoside analogue that acts as a classic inhibitor of transcription by RNA polymerase II. It is a relatively selective inhibitor of Cdk9, the kinase of the positive transcription elongation factor b (P-TEF-b) required for processive transcription elongation by RNA polymerase II. DRB also inhibits casein kinase II and suppresses the SIRT1/CK2α pathway, enhancing the radiosensitivity of human cancer cells. However, it does not inhibit kinase-independent activities of Cdk9, such as glucocorticoid receptor modulation.

Uses

Used in Research Applications:
5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used as an inhibitor of RNA polymerase II in various research applications. It helps in studying the mechanisms of cellular regulation and the role of RNA polymerase II in transcription.
Used in Cancer Research:
In cancer research, 5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used as an inhibitor of RNA synthesis, causing premature termination of transcription. This property makes it useful in investigating the effects of RNA synthesis inhibition on cancer cells and their growth.
Used in Mouse Melanoma Cells:
5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used as an inhibitor of RNA polymerase II in mouse melanoma cells, aiding in the study of melanoma cell behavior and the development of potential therapeutic strategies.
Used in Human Prostate Epithelial Cell Lines:
In human prostate epithelial cell lines, 5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used for the inhibition of cyclin D1 mRNA synthesis. This application helps researchers understand the role of cyclin D1 in prostate cancer progression and the potential of DRB as a therapeutic agent.
Used in Jurkat Cells:
5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used in Jurkat cells for the inhibition of interleukin-2 gene transcription. This application is valuable for studying the regulation of immune response genes and the potential impact of DRB on immune cell function.

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

InChI:InChI=1/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

Upstream product

• 142356-77-2 C₁₂H₁₂Cl₂N₂O₄S 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 142356-78-3 5,6-dichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole-2-thione 
• 142356-77-2 5,6-dichloro-2-mercapto-1-(β-D-ribofuranosyl)-benzimidazole 
• 19462-98-7 5,6-dichloro-2,3-dihydro-1H-1,3-benzodiazole-2-thione 
• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 6478-73-5 5,6-dichlorobenzimidazole 
• 105499-44-3 2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride 
• 118-00-3 G 
• 155520-55-1 5,6-dichloro-2-(methylthio)-1-β-D-ribofuranosylbenzimidazole 
• 137016-56-9 5,6-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)benzimidazole 
• 108126-17-6 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5,6-dichloro-1H-benzo[d]imidazol-1-yl)tetrahydrofuran-3,4-diyl diacetate 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 

Downstream Products

• 137016-65-0 1-(3-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 2'-<2-(4-nitrophenyl)ethyl triethylammonium phosphate> 
• 137016-70-7 1-(2-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 3'-<2-(4-nitrophenyl)ethyl triethylammonium phosphate> 
• 137016-55-8 1-(2-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 3'-<2,5-dichlorophenyl pyridinium phosphate> 
• 137016-67-2 1-(3-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 2'-<2,5-dichlorophenyl pyridinium phosphate> 
• 137016-82-1 1-(2-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazolyl-(2'-P-<2-(4-nitrophenyl)ethyl>>->5')-5,6-dichloro 1-(2,3-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)benzimidazole 
• 137016-76-3 1-(3-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazolyl-(2'-P-<2-(4-nitrophenyl)ethyl>>->5')-5,6-dichloro 1-(2,3-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)benzimidazole 
• 137016-77-4 1-(3-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazolyl-(2'-P-(2,5-dichlorophenyl)>->5')-5,6-dichloro 1-(2,3-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)benzimidazole 
• 137016-83-2 1-(2-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazolyl-<2'-P-(2,5-dichlorophenyl)>->5'>-5,6-dichloro 1-(2,3-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)benzimidazole 
• 137016-68-3 1-(2-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 3'-<2,5-dichlorophenyl 2-(4-nitrophenyl)ethyl phosphate> 
• 137016-62-7 1-(3-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 2'-<2,5-dichlorophenyl 2-(4-nitrophenyl)ethyl phosphate> 
• 137016-63-8 1-(3-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 2'-<2,5-dichlorophenyl 2-(4-nitrophenyl)ethyl phosphate> 
• 137016-60-5 5,6-dichloro-1-(2,3-di-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)benzimidazole 
• 137016-58-1 1-(2-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 
• 137016-59-2 1-(3-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 

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