53-85-0 Usage
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
Different sources of media describe the Uses of 53-85-0 differently. You can refer to the following data:
1. DRB is an inhibitor of RNA synthesis (causes premature termination of transcription).
2. 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.
3. 5,6-Dichlorobenzimidazole 1-β-D-ribofuranoside has been used:as an inhibitor of RNA polymerase II in mouse melanoma cellsfor the inhibition of cyclin D1 mRNA synthesis in human prostate epithelial cell linesin 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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 53-85-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 3 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 53-85:
(4*5)+(3*3)+(2*8)+(1*5)=50
50 % 10 = 0
So 53-85-0 is a valid CAS Registry Number.
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
53-85-0Relevant articles and documents
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Kissman et al.
, p. 1185,1187 (1957)
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ADENOSINE ANALOG AND ITS USE IN REGULATING THE CIRCADIAN CLOCK
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Paragraph 0132; 0133, (2018/08/12)
Provided are a kind of nucleoside analogue compounds, and compositions comprising these compounds and pentostatin, their use for modulating circadian rhythm, preferably, for shifting circadian phase, and methods for modulating circadian rhythm, preferably, for shifting circadian phase via these compounds or the compositions.
Benzimidazoles in the reaction of enzymatic transglycosylation
Mikhailopulo,Kazimierczuk,Zinchenko,Barai,Romanova,Eroshevskaya
, p. 477 - 480 (2007/10/02)
Substrate activity of a broad spectrum of derivatives of benzimidazole in the reaction of enzymatic ribo- and 2-deoxyribosylation catalyzed by purine nucleoside phosphorylase of whole cells of E. coli BMT-1D/1A has been studied Guanosine or 2'-deoxyguanosine were used as glycosyl donors.
