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
Abbreviations	EdU
ChEMBL	ChEMBL222932
ChemSpider	414657
Jmol interactive 3D	Image
MeSH	5-ethynyl-2'-deoxyuridine
PubChem	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 Key: CDEURGJCGCHYFH-DJLDLDEBSA-N 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).
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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

1. 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. doi:10.1016/j.jneumeth.2008.10.006. PMID 18996411.
2. Cavanagh, Brenton; Walker, T; Norazit, A; Meedeniya, A. C. (15 September 2011). "Thymidine analogues for tracking DNA synthesis.". Molecules 16 (9): 7980–93. doi:10.3390/molecules16097980. PMID 21921870.