5-Ethynyl-2'-deoxyuridine

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
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;
UNII	G373S00W2J ;
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 ;
	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. EdU is used to assay DNA synthesis in cell culture and detect cells in embryonic, neonatal and adult animals which have undergone DNA synthesis.^[1] Whilst at high doses it can be cytotoxic, this molecule is now widely used to track proliferating cells in multiple biological systems.

EdU-labelling allows cells to be isolated without denaturing DNA, allowing researchers to determine the transcriptional profile of cells.^[2] This approach has been used to assess transcription in neuronal cells^[3] and tissues^[4] that have recently divided either in vitro or in vivo.

^ Cite error: The named reference :0 was invoked but never defined (see the help page).
^ Endaya B, Cavanagh B, Alowaidi F, Walker T, de Pennington N, Ng JM, et al. (January 2016). "Isolating dividing neural and brain tumour cells for gene expression profiling". Journal of Neuroscience Methods. 257: 121–133. doi:10.1016/j.jneumeth.2015.09.020. PMID 26432933. S2CID 44969376.
^ Endaya BB, Lam PY, Meedeniya AC, Neuzil J (January 2016). "Transcriptional profiling of dividing tumor cells detects intratumor heterogeneity linked to cell proliferation in a brain tumor model". Molecular Oncology. 10 (1): 126–137. doi:10.1016/j.molonc.2015.09.001. PMC 5528932. PMID 26388584.
^ Ng HX, Lee EP, Cavanagh BL, Britto JM, Tan SS (September 2017). "A method for isolating cortical interneurons sharing the same birthdays for gene expression studies". Experimental Neurology. 295: 36–45. doi:10.1016/j.expneurol.2017.05.006. PMID 28511841. S2CID 3377296.

[:0-1] Cite error: The named reference :0 was invoked but never defined (see the help page).

[2] Endaya B, Cavanagh B, Alowaidi F, Walker T, de Pennington N, Ng JM, et al. (January 2016). "Isolating dividing neural and brain tumour cells for gene expression profiling". Journal of Neuroscience Methods. 257: 121–133. doi:10.1016/j.jneumeth.2015.09.020. PMID 26432933. S2CID 44969376.

[3] Endaya BB, Lam PY, Meedeniya AC, Neuzil J (January 2016). "Transcriptional profiling of dividing tumor cells detects intratumor heterogeneity linked to cell proliferation in a brain tumor model". Molecular Oncology. 10 (1): 126–137. doi:10.1016/j.molonc.2015.09.001. PMC 5528932. PMID 26388584.

[4] Ng HX, Lee EP, Cavanagh BL, Britto JM, Tan SS (September 2017). "A method for isolating cortical interneurons sharing the same birthdays for gene expression studies". Experimental Neurology. 295: 36–45. doi:10.1016/j.expneurol.2017.05.006. PMID 28511841. S2CID 3377296.

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