CAS 53-85-0|5,6-Dichlorobenzimidazole riboside
| Common Name | 5,6-Dichlorobenzimidazole riboside | ||
|---|---|---|---|
| CAS Number | 53-85-0 | Molecular Weight | 319.141 |
| Density | 1.8±0.1 g/cm3 | Boiling Point | 606.2±65.0 °C at 760 mmHg |
| Molecular Formula | C12H12Cl2N2O4 | Melting Point | 222-224ºC |
| MSDS | ChineseUSA | Flash Point | 320.4±34.3 °C |
Names
| Name | 5,6-Dichloropurine-1-β-D-ribofuanosyl-H-benzimidazole |
|---|---|
| Synonym | More Synonyms |
5,6-Dichlorobenzimidazole riboside BiologicalActivity
| 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 >>CancerSignaling 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 |
| InChIKey | XHSQDZXAVJRBMX-DDHJBXDOSA-N |
| SMILES | OCC1OC(n2cnc3cc(Cl)c(Cl)cc32)C(O)C1O |
| 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. |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATAMUTATION 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
- 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 |
Articles70
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| GSK-3β Phosphorylation of Cytoplasmic Dynein Reduces Ndel1 Binding to Intermediate Chains and Alters Dynein Motility. Traffic 16 , 941-61, (2015) Glycogen synthase kinase 3 (GSK-3) has been linked to regulation of kinesin-dependent axonal transport in squid and flies, and to indirect regulation of cytoplasmic dynein. We have now found evidence ... | |
| Upregulation of CYP1B1 expression by inflammatory cytokines is mediated by the p38 MAP kinase signal transduction pathway. Carcinogenesis 35(11) , 2534-43, (2014) Cytochrome P450 1B1 (CYP1B1) is an enzyme that has a unique tumor-specific pattern of expression and is capable of bioactivating a wide range of carcinogenic compounds. We have reported previously tha... |
Synonyms
| 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 |
