5,6-Dichlorobenzimidazole riboside

Names

[ CAS No. ]:
53-85-0

[ Name ]:
5,6-Dichlorobenzimidazole riboside

[Synonym ]:
1H-Benzimidazole, 5,6-dichloro-1-β-D-ribofuranosyl-
1H-Benzimidazole, 5,6-dichloro-1-β-D-ribofuranosyl- (9CI)
Benzimidazole, 5,6-dichloro-1-β-D-ribofuranosyl-
5,6-Dichloro-1-(β-D-ribofuranosyl)benzimidazole
5,6-Dichloro-1-(β-D-ribofuranosyl)-1H-benzimidazole
DRB
5,6-Dichlorobenzimidazole riboside
5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole
MFCD00036785
5,6-Dichlorobenzimidazole 1-β-D-Ribofuranoside

Biological Activity

[Description]:

5,6-Dichlorobenzimidazole riboside is a nucleoside analog that inhibits several carboxyl-terminal domain (CTD) kinases including casein kinase II and CDKs[1][2][3][4]. 5,6-Dichlorobenzimidazole riboside trigger p53-dependent apoptosis of human colon adenocarcinoma cells without inducing genotoxic stress to healthy cells[5].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> CDK

[References]

[1]. Zandomeni RO. Kinetics of inhibition by 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole on calf thymus casein kinase II. Biochem J. 1989 Sep 1;262(2):469-73.

[2]. Yankulov K, et al. The transcriptional elongation inhibitor 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole inhibits transcription factor IIH-associated protein kinase. J Biol Chem. 1995 Oct 13;270(41):23922-5.

[3]. Rickert P, et al. Cyclin C/CDK8 and cyclin H/CDK7/p36 are biochemically distinct CTD kinases. Oncogene. 1999 Jan 28;18(4):1093-102.

[4]. Schang LM. Cyclin-dependent kinases as cellular targets for antiviral drugs. J Antimicrob Chemother. 2002 Dec;50(6):779-92.

[5]. te Poele RH, et al. RNA synthesis block by 5, 6-dichloro-1-beta-D-ribofuranosylbenzimidazole (DRB) triggers p53-dependent apoptosis in human colon carcinoma cells. Oncogene. 1999 Oct 14;18(42):5765-72.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
606.2±65.0 °C at 760 mmHg

[ Melting Point ]:
222-224ºC

[ Molecular Formula ]:
C₁₂H₁₂Cl₂N₂O₄

[ Molecular Weight ]:
319.141

[ Flash Point ]:
320.4±34.3 °C

[ Exact Mass ]:
318.017426

[ PSA ]:
87.74000

[ LogP ]:
2.05

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.750

[ Storage condition ]:
−20°C

[ 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.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DD7310000

CHEMICAL NAME :: Benzimidazole, 5,6-dichloro-1-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 53-85-0

BEILSTEIN REFERENCE NO. :: 0039123

LAST UPDATED :: 199806

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H12-Cl2-N2-O4

MOLECULAR WEIGHT :: 319.16

WISWESSER LINE NOTATION :: T56 BN DNJ GG HG B- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Human HeLa cell

DOSE/DURATION :: 40 umol/L

REFERENCE :: PNASA6 Proceedings of the National Academy of Sciences of the United States of America. (National Academy of Sciences, Printing & Pub. Office, 2101 Constitution Ave., Washington, DC 20418) V.1- 1915- Volume(issue)/page/year: 79,2569,1982

Safety Information

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DD7310000

[ HS Code ]:
29349990

Precursor & DownStream

Precursor

DownStream

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