| Identification | Back Directory | [Name]
DRB | [CAS]
53-85-0 | [Synonyms]
DRB
DBR
NSC 401575
DRB (Benzimidazole)
5,6-DICHLOROBENZIMIDAZOLE RIBOSIDE
dichlororibofuranosylbenzimidazole
Dichlorobenzimidazoleribofuranoside
5,6-dichlorobenzimidazoleriboside(drb)
5,6-DICHLOROBENZIMIDAZOLE RIBOSIDE 98%
5,6-DICHLOROBENZIMIDAZOLE RIBOSIDE (DRB)98%
5,6-Dichloro-1-b-D-ribofuranosylbenzimidazole
5,6-dichloro-1-β-d-ribofuranosylbenzimidazole
1-β-D-Ribofuranosyl-5,6-dichlorobenziMidazole
5,6-dichlorobenzimidazole 1-β-d-ribofuranoside
5,6-Dichlorobenzimidazole-1-b-D-ribofuranoside
5,6-DICHLORO-BETA-D-RIBOFURANOSYL-BENZIMIDAZOLE
5,6-DICHLORO-1-BETA-D-RIBOFURANOSYLBENZIMIDAZOLE
5,6-dichloro-1-beta-d-ribofuranosyl-benzimidazol
5,6-DICHLOROBENZIMIDAZOLE-1-BETA-D-RIBOFURANOSIDE
DBR,5,6-Dichlorobenzimidazole1-b-D-ribofuranoside
4,5-dichloro-2-(3-methylbenzyl)pyridazin-3(2h)-one
DBR, 5,6-Dichlorobenzimidazole 1--D-ribofuranoside
5,6-Dichlorobenzimidazole-1-β-D-ribofuranoside ,98%
5,6-Dichloropurine-1--D-ribofuanosyl-H-benzimidazole
5,6-Dichloropurine-1-b-D-ribofuanosyl-H-benzimidazole
5,6-DICHLOROPURINE-1-BETA-D-RIBOFURANOSYL-H-BENZIMIDAZOLE
5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole, 5,6-Dichlorobenzimidazole riboside, DRB | [Molecular Formula]
C12H12Cl2N2O4 | [MDL Number]
MFCD00036785 | [MOL File]
53-85-0.mol | [Molecular Weight]
319.14 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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) | [form ]
White solid | [pka]
13.23±0.70(Predicted) | [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 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
An inhibitor of RNA synthesis (causes premature termination of transcription) | [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 | [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. | [in vivo]
5,6-Dichlorobenzimidazole riboside (2.0-3.0 mg/0.25 mL water, ?intraperitoneally injected twice a day for 5 days) does not inhibit the multiplication of the PR8 strain of influenza virus in mice[7].
| [storage]
Store at -20°C | [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 |
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