5-Ethynyl-2'-deoxyuridine

5-Ethynyl-2′-deoxyuridine (EdU) is a thymidine analogue which is incorporated into the DNA of dividing cells. EdU is used to assay DNA synthesis in cell culture and detect cells in embryonic, neonatal and adult animals which have undergone DNA synthesis. Whilst at high doses it can be cytotoxic, this molecule is now widely used to track proliferating cells in multiple biological systems.

5-Ethynyl-2′-deoxyuridine
Names
IUPAC name
2′-Deoxy-5-ethynyluridine
Systematic IUPAC name
5-Ethynyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4(1H,3H)-dione
Other names
5-Ethynyl-2′-deoxyuridine
Identifiers
3D model (JSmol)
Abbreviations EdU
ChEMBL
ChemSpider
ECHA InfoCard 100.230.902
MeSH 5-ethynyl-2'-deoxyuridine
PubChem CID
UNII
  • InChI=1S/C11H12N2O5/c1-2-6-4-13(11(17)12-10(6)16)9-3-7(15)8(5-14)18-9/h1,4,7-9,14-15H,3,5H2,(H,12,16,17)/t7-,8+,9+/m0/s1 Y
    Key: CDEURGJCGCHYFH-DJLDLDEBSA-N Y
SMILES
  • C#C\C1=C\N(C(=O)NC1=O)[C@H]2C[C@H](O)[C@@H](CO)O2
Properties
C11H12N2O5
Molar mass 252.226 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

EdU-labelling allows cells to be isolated without denaturing DNA, allowing researchers to determine the transcriptional profile of cells. This approach has been used to assess transcription in neuronal cells and tissues that have recently divided either in vitro or in vivo.

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