| Identification | Back Directory | [Name]
5-Ethynyl-2'-deoxycytidine | [CAS]
69075-47-4 | [Synonyms]
5-Ethynyl-2'-dC
-Ethynyl-2&rsquo
5-Ethynyl-2'-deoxycytidine
2'-Deoxy-5-ethynylcytidine
Cytidine, 2'-deoxy-5-ethynyl-
5-Ethynyl-2'-deoxycytidine>
5-Ethynyl-2′-deoxycytidine, (EdC)
5-Ethynyl-2'-deoxycytidine 69075-47-4
5-Ethynyl-2'-deoxycytidine, (EdC) AldrichCPR
4-Amino-5-ethynyl-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one | [Molecular Formula]
C11H13N3O4 | [MDL Number]
MFCD22417249 | [MOL File]
69075-47-4.mol | [Molecular Weight]
251.239 |
| Chemical Properties | Back Directory | [Melting point ]
191 °C (decomp)(Solv: dichloromethane (75-09-2); methanol (67-56-1)) | [Boiling point ]
475.7±55.0 °C(Predicted) | [density ]
1.54±0.1 g/cm3(Predicted) | [storage temp. ]
Store at 2-8°C, protect from light, stored under nitrogen | [solubility ]
DMF: 5 mg/ml; DMSO: 20 mg/ml; PBS (pH 7.2): 10 mg/ml | [form ]
powder to crystal | [pka]
14.03±0.60(Predicted) | [color ]
White to Light yellow to Light orange | [λmax]
292nm(H2O)(lit.) | [InChI]
1S/C11H13N3O4/c1-2-6-4-14(11(17)13-10(6)12)9-3-7(16)8(5-15)18-9/h1,4,7-9,15-16H,3,5H2,(H2,12,13,17)/t7-,8+,9+/m0/s1 | [InChIKey]
HMJSYXIPNSASJY-DJLDLDEBSA-N | [SMILES]
NC1=NC(=O)N(C=C1C#C)[C@H]2C[C@H](O)[C@@H](CO)O2 |
| Hazard Information | Back Directory | [Description]
5''-Ethynyl-2''-deoxycytidine (EdC) is a nucleoside analog that inhibits replication of the herpes simplex virus-1 (HSV-1) KOS strain (ID50 = 0.2 μg/mL). It also reduces virus-induced cytopathogenicity of HSV-1, HSV-2, and vaccinia virus strains in PRK cells (MICs = 0.2-0.4, 1-2, and 5 μg/ml, respectively). EdC is an inhibitor of thymidylate synthetase, selectively reducing DNA incorporation of [1'',2''-3H]deoxyuridine over [CH3-3H]deoxythymidine in PRK cells (ID50s = 3 and 120 μg/ml, respectively). It inhibits thymidine synthetase in and reduces proliferation of L1210 cells, an effect which is reversed by addition of deoxythymidine (ID50s = 4.4 and 1,000 μg/ml, respectively). EdC has been used to monitor DNA synthesis and cellular replication via click chemistry conjugation of the ethynyl group to an azido group of various fluorochromes. | [Uses]
5-Ethynyl-2’-deoxycytidine is an lower toxicity analog of 2’-deoxycytidine, a metabolic labeling probe for DNA synthesis. 5-Ethynyl-2’-deoxycytidine is most commonly used when thymidine analogs is undesirable. | [reaction suitability]
reaction type: click chemistry | [Synthesis]
1) 5-Iodo-2’3’5’-oxo-triacetyluridine (15 g, 30.23 mmol, 1eq) was dissolved in 200 ml of CH2Cl2:(C2H5)3N1:1 mixed solution, to which was added under the protection of N2 (PPh3)2PdCl2 (1.59 g, 2.27 mmol. 0.075eq), CuI (0.86g, 4.52mmol, 0. | [References]
[1] R. WALKER. The synthesis and properties of some antiviral nucleosides[J]. Nucleic Acids Research, 1978, 1 1. DOI: 10.1093/nar/1.suppl_1.s103
[2] E DE CLERCQ. Antiviral, antimetabolic, and cytotoxic activities of 5-substituted 2’-deoxycytidines.[J]. Molecular Pharmacology, 1982, 21 1: 217-223.
[3] FRANK SEELA. 5-Ethynyl-2’-deoxycytidine: a DNA building block with a “clickable” side chain.[J]. Acta crystallographica. Section C, Crystal structure communications, 2012, 68 Pt 10: o395-8. DOI: 10.1107/s0108270112038267 |
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