5'-Ethynyl-2'-deoxycytidine

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.Formal Name: 2'-deoxy-5-ethynyl-cytidine. CAS Number: 69075-47-4. Synonyms: Click Tag(TM) 5'-Ethynyl-2'-deoxycytidine, EdC, 2'-deoxy-5-Ethynylcytidine. Molecular Formula: C11H13N3O4. Formula Weight: 251.2. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 5 mg/ml, DMSO: 20 mg/ml, PBS (pH 7.2): 10 mg/ml. lambdamax: 212, 233, 292 nm. SMILES: NC(C(C#C)=C1)=NC(N1[C@H]2C[C@H](O)[C@@H](CO)O2)=O. InChi Code: 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. InChi Key: HMJSYXIPNSASJY-DJLDLDEBSA-N.