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;
3D model (JSmol)	Interactive image;
Abbreviations	EdU
ChEMBL	ChEMBL222932;
ChemSpider	414657;
ECHA InfoCard	100.230.902
MeSH	5-ethynyl-2'-deoxyuridine
PubChem CID	472172;
CompTox Dashboard (EPA)	DTXSID20976652 ;
	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	252.226 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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. doi:10.1016/j.jneumeth.2008.10.006. PMID 18996411.
^ 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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[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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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