A nucleoside analog
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5'-Ethynyl-2'-deoxycytidine

Item No. 11581

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2'-deoxy-5-ethynyl-cytidine
CAS Number
69075-47-4
Synonyms
  • Click Tag™ 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(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product 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).1 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).2 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.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Walker, R.T., Barr, P.J., De Clereq, E., et al. The synthesis and properties of some antiviral nucleosides. Nucleic Acids Res. 1(Supp. 1), s103-s108 (1978).

    2. De Clercq, E., Balzarini, J., Descamps, J., et al. Antiviral, antimetabolic, and cytotoxic activities of 5-substituted 2'-deoxycytidines. Mol. Pharmacol. 21(1), 217-223 (1982).

    3. Seela, F., Mei, H., Xiong, H., et al. 5-Ethynyl-2'-deoxycytidine: A DNA building block with a “clickable” side chain. Acta. Crystallogr. C. 68(Pt 10), o395-398 (2012).