Revision as of 18:28, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 461498176 of page 5-Ethynyl-2'-deoxyuridine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 13:00, 14 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Added bibcode. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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|Name=5-Ethynyl-2'-deoxyuridine |
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|verifiedrevid = 322007341 |
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|ImageFile=5-ethynyl-2'-deoxyuridine.png |
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| Name = 5-Ethynyl-2′-deoxyuridine |
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| verifiedrevid = 477224266 |
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|ImageSize=200px |
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| ImageFile = 5-ethynyl-2'-deoxyuridine.png |
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|IUPACName=5-Ethynyl-1-pyrimidine-2,4-dione |
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| ImageSize = 200px |
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|OtherNames= 2'-Deoxy-5-ethynyluridine; 5-Ethynyl-2´-deoxyuridine |
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| IUPACName = 2′-Deoxy-5-ethynyluridine |
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|Section1= {{Chembox Identifiers |
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| SystematicName = 5-Ethynyl-1-pyrimidine-2,4(1''H'',3''H'')-dione |
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| Abbreviations=EdU |
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| OtherNames = 5-Ethynyl-2′-deoxyuridine |
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| ChemSpiderID = 414657 |
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|Section1={{Chembox Identifiers |
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| InChIKey = CDEURGJCGCHYFH-DJLDLDEBBH |
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| Abbreviations = EdU |
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| 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 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 414657 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = CDEURGJCGCHYFH-DJLDLDEBSA-N |
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| StdInChIKey = CDEURGJCGCHYFH-DJLDLDEBSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 61135-33-9 --> |
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| CASNo = 61135-33-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEMBL = 222932 |
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| UNII = G373S00W2J |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 222932 |
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| PubChem = 472172 |
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| PubChem = 472172 |
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| SMILES = C#C\C1=C\N(C(=O)NC1=O)2C(O)(CO)O2 |
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| SMILES = C#C\C1=C\N(C(=O)NC1=O)2C(O)(CO)O2 |
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| MeSHName= 5-ethynyl-2'-deoxyuridine |
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| MeSHName = 5-ethynyl-2'-deoxyuridine |
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|Section2= {{Chembox Properties |
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| C=11|H=12|N=2|O=5 |
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| C=11 | H=12 | N=2 | O=5 |
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|Section3= {{Chembox Hazards |
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'''5-Ethynyl-2′-deoxyuridine''' ('''EdU''') is a ] analogue which is incorporated into the ] 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.<ref name=":0" /> Whilst at high doses it can be cytotoxic, this molecule is now widely used to track proliferating cells in multiple biological systems. |
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EdU-labelling allows cells to be isolated without denaturing DNA, allowing researchers to determine the transcriptional profile of cells.<ref>{{cite journal | vauthors = Endaya B, Cavanagh B, Alowaidi F, Walker T, de Pennington N, Ng JM, Lam PY, Mackay-Sim A, Neuzil J, Meedeniya AC | display-authors = 6 | title = Isolating dividing neural and brain tumour cells for gene expression profiling | journal = Journal of Neuroscience Methods | volume = 257 | pages = 121–133 | date = January 2016 | pmid = 26432933 | doi = 10.1016/j.jneumeth.2015.09.020 | s2cid = 44969376 }}</ref> This approach has been used to assess transcription in neuronal cells<ref>{{cite journal | vauthors = Endaya BB, Lam PY, Meedeniya AC, Neuzil J | title = Transcriptional profiling of dividing tumor cells detects intratumor heterogeneity linked to cell proliferation in a brain tumor model | journal = Molecular Oncology | volume = 10 | issue = 1 | pages = 126–137 | date = January 2016 | pmid = 26388584 | pmc = 5528932 | doi = 10.1016/j.molonc.2015.09.001 }}</ref> and tissues<ref>{{cite journal | vauthors = Ng HX, Lee EP, Cavanagh BL, Britto JM, Tan SS | title = A method for isolating cortical interneurons sharing the same birthdays for gene expression studies | journal = Experimental Neurology | volume = 295 | pages = 36–45 | date = September 2017 | pmid = 28511841 | doi = 10.1016/j.expneurol.2017.05.006 | s2cid = 3377296 }}</ref> that have recently divided either ''in vitro'' or ''in vivo''. |
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==Detection== |
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EdU is labeled and detected with an ] molecule (most commonly ] azides) through ] ].<ref name=":0">{{cite journal | vauthors = Chehrehasa F, Meedeniya AC, Dwyer P, Abrahamsen G, Mackay-Sim A | title = EdU, a new thymidine analogue for labelling proliferating cells in the nervous system | journal = Journal of Neuroscience Methods | volume = 177 | issue = 1 | pages = 122–130 | date = February 2009 | pmid = 18996411 | doi = 10.1016/j.jneumeth.2008.10.006 | hdl-access = free | s2cid = 21427874 | hdl = 10072/25744 }}</ref><ref>{{cite journal | vauthors = Cavanagh BL, Walker T, Norazit A, Meedeniya AC | title = Thymidine analogues for tracking DNA synthesis | journal = Molecules | volume = 16 | issue = 9 | pages = 7980–7993 | date = September 2011 | pmid = 21921870 | pmc = 6264245 | doi = 10.3390/molecules16097980 | doi-access = free }}</ref> Unlike the commonly used ], EdU detection requires no heat or acid treatment. |
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== Toxicity == |
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EdU incorporated into DNA induces ] through the formation of interstrand crosslinks.<ref>{{cite journal | vauthors = Ligasová A, Strunin D, Friedecký D, Adam T, Koberna K | title = A fatal combination: a thymidylate synthase inhibitor with DNA damaging activity | journal = PLOS ONE | volume = 10 | issue = 2 | pages = e0117459 | date = 2015-02-11 | pmid = 25671308 | pmc = 4324964 | doi = 10.1371/journal.pone.0117459 | doi-access = free | bibcode = 2015PLoSO..1017459L }}</ref> These are detected by the cell during ], which is reflected by phosphorylation of histone ], arrest in the ] progression, and ].<ref>{{cite journal | vauthors = Zhao H, Halicka HD, Li J, Biela E, Berniak K, Dobrucki J, Darzynkiewicz Z | title = DNA damage signaling, impairment of cell cycle progression, and apoptosis triggered by 5-ethynyl-2'-deoxyuridine incorporated into DNA | journal = Cytometry. Part A | volume = 83 | issue = 11 | pages = 979–988 | date = November 2013 | pmid = 24115313 | pmc = 3846616 | doi = 10.1002/cyto.a.22396 }}</ref> |
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== References == |
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<!--- See http://en.wikipedia.org/Wikipedia:Footnotes on how to create references using <ref></ref> tags which will then appear here automatically --> |
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{{Reflist}} |
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== External links == |
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*{{Commonscat-inline|EdU}} |
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{{DEFAULTSORT:Ethynyl-2'-Deoxyuridine, 5-}} |
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