C4798-100mg | DRB [53-85-0] Clinisciences

Background

5, 6-dichloro-1-β-D-ribofuranosylbenzimidazole (DRB) is a transcriptional elongation inhibitor.

Cyclin-dependent kinases (CDKs) belong to a family of protein kinases involved in regulating the cell cycle, transcription, mRNA processing, and the differentiation of nerve cells.[1] They are expressed in all known eukaryotes. With cyclin, CDK shows kinase activity. CDKs are serine-threonine kinases [1].

DRB inhibited the activity of several carboxyl-terminal domain (CTD) kinases including casein kinase II, Cdk7, Cdk8, and Cdk9 with the IC50 of 4-10 μM, ~20 μM, ~20 μM, and 3 μM) [2-5]. In HeLa cells, DRB (75 μM) inhibited 60-75% of nuclear heterogeneous RNA (hnRNA) synthesis. DRB (75 μM) reduced the appearance of labeled cytoplasmic poly(A)-containing messenger RNA (mRNA) by approximately 95%. DRB inhibited the initiation of hnRNA chains, but did not directly interfere with labeling of poly(A) [6]. DRB inhibited influenza virus multiplication in the chorioallantoic membrane in vitro [7]. DRB inhibited a HeLa protein kinase whihc phosphorylated an RNA polymerase II-derived peptide [8]. DRB can also inhibit HIV transcription (IC50 = ~4 μM) by targeting elongation enhanced by the HIV-encoded transactivator Tat.

References:
[1]. Zandomeni, R.O. Kinetics of inhibition by 5,6-dichloro-1-β-D-ribofuranosylbenzimidazole on calf thymus casein kinase II. Biochemistry Journal 262, 469-473 (1989).
[2]. Yankulov, K.,Yamashita, K.,Roy, R., et al. The transcriptional elongation inhibitor 5,6-dichloro-1-β-D-ribofuranosylbenzimidazole inhibits transcription factor IIH-associated protein kinase. The Journal of Biological Chemisty 270(41), 23922-23925 (1995).
[3]. Rickert, P.,Corden, J.L., and Lees, E. Cyclin C/CDK8 and cyclin H/CDK7/p36 are biochemically distinct CTD kinases. Oncogene 18, 1093-1102 (1999).
[4]. Schang, L.M. Cyclin-dependent kinases as cellular targets for antiviral drugs. Journal of Antimicrobial Chemotherapy 50, 779-792 (2002).
[5] Sehgal P B, Darnell J E, Tamm I. The inhibition of DRB (5, 6-dichloro-1-β-d-ribofuranosylbenzimidazole) of hnRNA and mRNA production in HeLa cells[J]. Cell, 1976, 9(3): 473-480.
[6] Tamm I, Tyrrell D A J. Influenza virus multiplication in the chorioallantoic membrane in vitro: kinetic aspects of inhibition by 5, 6-dichloro-1-β-D-ribofuranosylbenzimidazole[J]. The Journal of experimental medicine, 1954, 100(6): 541.
[7] Stevens A, Maupin M K. 5, 6-Dichloro-1-β-d-ribofuranosylbenzimidazole inhibits a HeLa protein kinase that phosphorylates an RNA polymerase II-derived peptide[J]. Biochemical and biophysical research communications, 1989, 159(2): 508-515.

Product Citation

1. Chi Hin Wong, Chi Han Li, et al. "The Establishment of CDK9/ RNA PolII/H3K4me3/DNA Methylation Feedback Promotes HOTAIR Expression by RNA Elongation Enhancement in Cancer." bioRxiv. 2019 October 21.

Chemical Properties

Storage	Store at -20°C
M.Wt	319.1
Cas No.	53-85-0
Formula	C₁₂H₁₂Cl₂N₂O₄
Synonyms	NSC 401575,Benzimidazole
Solubility	insoluble in EtOH; insoluble in H2O; ≥12.6 mg/mL in DMSO
Chemical Name	5,6-dichloro-1-β-D-ribofuranosyl-1H-benzimidazole
SDF	Download SDF
Canonical SMILES	O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N2C=NC3=C2C=C(Cl)C(Cl)=C3
Shipping Condition	Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips	We do not recommend long-term storage for the solution, please use it up soon.

Quality Control

Purity = 99.92%

Chemical structure

DRB [53-85-0]

Referentie C4798-100mg

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