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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

DRB

Cayman Chemical Item Number 10010302

Benzimidazole; NSC 401575 (CAS 53-85-0)

DRB (CAS 53-85-0)

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Description

DRB is a nucleoside analog that inhibits several carboxyl-terminal domain (CTD) kinases including casein kinase II (IC50 = 4-10 µM)1, cyclin-dependent kinase 7 (CDK7) (IC50 = ~20 µM)2,3, CDK8 (IC50 = ~20 µM)3, and CDK9 (IC50 = 3 µM).4 Through inhibition of certain CTD kinases, DRB inhibits an elongation step during RNA polymerase II transcription5,6, which can trigger p53-dependent apoptosis of human colon adenocarcinoma cells without inducing genotoxic stress to healthy cells.7 DRB can also inhibit HIV transcription (IC50 = ~4 µM) by targeting elongation enhanced by the HIV-encoded transactivator Tat.8

1 Zandomeni, R.O. Kinetics of inhibition by 5,6-dichloro-1-β-D-ribofuranosylbenzimidazole on calf thymus casein kinase II. Biochem J 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. J Biol Chem 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. J Antimicrob Chemother 50 779-792 (2002).

5 Zandomeni, R., Zandomeni, M.C., Shugar, D., et al. Casein kinase type II is involved in the inhibition by 5,6-dichloro-1-β-D-ribofuranosylbenzimidazole of specific RNA polymerase II transcription. J Biol Chem 261(7) 3414-3419 (1986).

6 Yamaguchi, Y., Wada, T., and Handa, H. Interplay between positive and negative elongation factors: drawing a new view of DRB. Genes Cells 3 9-15 (1998).

7 te Poele, R.H., Okorokov, A.L., and Joel, S.P. RNA synthesis block by 5,6-dichloro-1-β-D-ribofuranosylbenzimidazole (DRB) triggers p53-dependent apoptosis in human colon carcinoma cells. Oncogene 18 5765-5772 (1999).

8 Marciniak, R.A., and Sharp, P.A. HIV-1 tat protein promotes formation of more-processive elongation complexes. EMBO J 10(13) 4189-4196 (1991).

Synonyms
  • Benzimidazole
  • NSC 401575
Formal Name 5,​6-​dichloro-​1-​β-​D-​ribofuranosyl-​1H-​benzimidazole
CAS Number 53-85-0
Molecular Formula C12H12Cl2N2O4
Formula Weight 319.1
Formulation A crystalline solid
Purity ≥98%
λmax 214 nm
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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OC[C@H]​1O[C@H]​([C@H]​(O)​[C@@H]​1O)​n1cnc2cc(Cl)​c(Cl)​cc12

Background Reading

Zandomeni, R.O. Kinetics of inhibition by 5,6-dichloro-1-β-D-ribofuranosylbenzimidazole on calf thymus casein kinase II. Biochem J 262 469-473 (1989).

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).

Yamaguchi, Y., Wada, T., and Handa, H. Interplay between positive and negative elongation factors: drawing a new view of DRB. Genes Cells 3 9-15 (1998).

Marciniak, R.A., and Sharp, P.A. HIV-1 tat protein promotes formation of more-processive elongation complexes. EMBO J 10(13) 4189-4196 (1991).

Schang, L.M. Cyclin-dependent kinases as cellular targets for antiviral drugs. J Antimicrob Chemother 50 779-792 (2002).

te Poele, R.H., Okorokov, A.L., and Joel, S.P. RNA synthesis block by 5,6-dichloro-1-β-D-ribofuranosylbenzimidazole (DRB) triggers p53-dependent apoptosis in human colon carcinoma cells. Oncogene 18 5765-5772 (1999).

Nam, K.A., Kim, S., Heo, Y.H., et al. Resveratrol analog, 3,5,2',4'-tetramethoxy-trans-stilbene, potentiates the inhibition of cell growth and induces apoptosis in human cancer cells. Arch Pharm Res 24(5) 441-445 (2001).

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. J Biol Chem 270(41) 23922-23925 (1995).

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Size Price Quantity Subtotal
10 mg $24.00 $0.00
50 mg $108.00 $0.00
100 mg $192.00 $0.00
250 mg $420.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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