5-Ethynyl-2'-deoxycytidine

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CAS:69075-47-4
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5-Ethynyl-2'-deoxycytidine Basic information
Product Name:5-Ethynyl-2'-deoxycytidine
Synonyms:5-Ethynyl-2′-deoxycytidine, (EdC);Cytidine, 2'-deoxy-5-ethynyl-;2'-Deoxy-5-ethynylcytidine;5-Ethynyl-2'-deoxycytidine, (EdC) AldrichCPR;5-Ethynyl-2'-deoxycytidine;5-Ethynyl-2'-dC;4-Amino-5-ethynyl-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;-Ethynyl-2&rsquo
CAS:69075-47-4
MF:C11H13N3O4
MW:251.24
EINECS:
Product Categories:Carbohydrates & Derivatives, Heterocycles, Nucleotides, Bases & Related Reagents
Mol File:69075-47-4.mol
5-Ethynyl-2'-deoxycytidine Structure
5-Ethynyl-2'-deoxycytidine Chemical Properties
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
pka14.03±0.60(Predicted)
form powder to crystal
color White to Light yellow to Light orange
λmax292nm(H2O)(lit.)
Safety Information
WGK Germany 3
HS Code 2934.99.4400
MSDS Information
5-Ethynyl-2'-deoxycytidine Usage And Synthesis
Description5''-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.
Uses5-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.
UsesA relatively nontoxic 2′-deoxycytidine analog for metabolic labeling of newly synthesized DNA in vivo. Especially suitable if the use of thymidine analogs is undesirable.
reaction suitabilityreaction type: click chemistry
5-Ethynyl-2'-deoxycytidine Preparation Products And Raw materials
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