Introduction：Basic information about CAS 478182-28-4|R-1479, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | R-1479 |
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| CAS Number | 478182-28-4 | Molecular Weight | 284.229 |
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| Density | / | Boiling Point | / |
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| Molecular Formula | C9H12N6O5 | Melting Point | / |
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| MSDS | / | Flash Point | / |
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Names
| Name | 4-amino-1-[(2R,3R,4S,5R)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one |
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| Synonym | More Synonyms |
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R-1479 BiologicalActivity
| Description | R-1479 is a specific inhibitor of HCV replication in the HCV subgenomic replicon system (IC50=1.28 μM). |
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| Related Catalog | Signaling Pathways >>Anti-infection >>HCVResearch Areas >>Infection |
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| Target | IC50: 1.28 μM (HCV replication)[1] |
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| In Vitro | R-1479 (R1479) inhibits HCV RNA replication with a mean IC50 value of 1.28 μM when measured as dose-dependent reduction of Renillaluciferase activity after a 72 h incubation of proliferating replicon cells. R-1479 shows no effect on cell viability or proliferation of HCV replicon or Huh-7 cells at concentrations up to 2 mM[1]. The most potent and non-cytotoxic derivative is R-1479 with an IC50 of 1.28 μM in the HCV replicon system. The triphosphate of R-1479 is prepared and shown to be an inhibitor of RNA synthesis mediated by NS5B (IC50=320 nM), the RNA polymerase encoded by HCV. R-1479 displays good activity in the replicon assay with no measurable cytotoxic or cytostatic effect[2]. |
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| Kinase Assay | The membrane-associated, native HCV replicase complex is isolated from 2209-23 HCV replicon cells and a derived cell line carrying HCV replicon RNA with a S282T mutation in the NS5B coding sequence. The in vitro replicase assay contain 10 μL of cytoplasmic membrane fraction, 50 mM HEPES (pH 7.5), 10 mM KCl, 10 mM dithiothreitol, 5 mM MgCl2, 20 μg/mL actinomycin D, 1 mM ATP, 1 mM GTP, 1 mM UTP, 30 μCi of [α-33P]CTP (3000 Ci/mmol, 10 mCi/mL), 1 unit/μL SUPERase•In, 10 mM creatine phosphate, and 200 μg/mL creatine phosphokinase in a final volume of 25 μL. Inhibition by nucleotide analogs is determined[1]. |
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| Cell Assay | The effect of R-1479 on the incorporation of tritiated thymidine into cellular DNA is measured using the [3H]thymidine incorporation scintillation proximity assay system. MTT and WST-1 assay systems are used to measure cell viability. The ATP bioluminescence assay kit HSII is used to measure intracellular ATP levels[1]. |
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| References | [1]. Klumpp K, et al. The novel nucleoside analog R1479 (4'-azidocytidine) is a potent inhibitor of NS5B-dependent RNA synthesis and hepatitis C virus replication in cell culture. J Biol Chem. 2006 Feb 17;281(7):3793-9. [2]. Smith DB, et al. Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: the discovery of R1479. Bioorg Med Chem Lett. 2007 May 1;17(9):2570-6. |
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Chemical & Physical Properties
| Molecular Formula | C9H12N6O5 |
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| Molecular Weight | 284.229 |
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| Exact Mass | 284.086914 |
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| PSA | 181.57000 |
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| LogP | -0.20 |
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| InChIKey | ODLGMSQBFONGNG-JVZYCSMKSA-N |
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| SMILES | [N-]=[N+]=NC1(CO)OC(n2ccc(N)nc2=O)C(O)C1O |
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| Storage condition | -20°C |
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Synonyms
| 4-amino-1-[(2R,3R,4S,5R)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one (non-preferred name) |
| R-1479||4'-Azidocytidine|R1479 |
| CS-0362 |
| 4'-azidocytidine |
| 4'azidocytidine |
| R1479 |
| 4-Amino-1-[(2R,3R,4S,5R)-5-azido-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone |
| R-1479 |
