5-Ethynyl-2'-deoxyuridine

5-Ethynyl-2'-deoxyuridine
Names

IUPAC name 5-Ethynyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Other names 2'-Deoxy-5-ethynyluridine; 5-Ethynyl-2´-deoxyuridine
Identifiers
CAS Number	61135-33-9^N
3D model (JSmol)	Interactive image
Abbreviations	EdU
ChemSpider	414657^Y
ECHA InfoCard	100.230.902
MeSH	5-ethynyl-2'-deoxyuridine
PubChem CID	472172
InChI 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 InChI=1/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 Key: CDEURGJCGCHYFH-DJLDLDEBBH
SMILES C#C\C1=C\N(C(=O)NC1=O)[C@H]2C[C@H](O)[C@@H](CO)O2
Properties
Chemical formula	C₁₁H₁₂N₂O₅
Molar mass	252.23 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

5-Ethynyl-2´-deoxyuridine (EdU) is a thymidine analogue which is incorporated into the DNA of dividing cells and is used to assay DNA synthesis in cell culture. At high doses it can be cytotoxic.

Detection

EdU is detected with a fluorescent azide which forms a covalent bond using click chemistry.^[1]^[2] Unlike the commonly used bromodeoxyuridine, EdU detection requires no heat or acid treatment.

References

↑ Chehrehasa, F; Meedeniya, AC; Dwyer, P; Abrahamsen, G; Mackay-Sim, A (February 2009). "EdU, a new thymidine analogue for labelling proliferating cells in the nervous system". J. Neurosci. Methods. 177 (1): 122–30. PMID 18996411. doi:10.1016/j.jneumeth.2008.10.006.
↑ Cavanagh, Brenton; Walker, T; Norazit, A; Meedeniya, A. C. (15 September 2011). "Thymidine analogues for tracking DNA synthesis.". Molecules. 16 (9): 7980–93. PMID 21921870. doi:10.3390/molecules16097980.

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