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900584

Sigma-Aldrich

5-Ethynyl-2′-deoxyuridine

95%

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Synonym(s):
EdU
Empirical Formula (Hill Notation):
C11H12N2O5
CAS Number:
Molecular Weight:
252.22
UNSPSC Code:
12352208
NACRES:
NA.22

Quality Level

Assay

95%

form

powder

mp

206 °C

storage temp.

−20°C

SMILES string

OC[C@@H]1[C@@H](O)C[C@H](N2C(NC(C(C#C)=C2)=O)=O)O1

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

InChI key

CDEURGJCGCHYFH-DJLDLDEBSA-N

General description

5-Ethynyl-2′-deoxyuridine (EdU) is a thymidine analogue that can be incorporated into cellular DNA for cell proliferation studies. The incorporated nucleoside analogue can be detected by a copper-catalyzed click reaction with a fluorescent azide.

Application

5-Ethynyl-2′-deoxyuridine (EdU) is used for:
  • Labeling newly synthesized DNA during replication
  • Cell proliferating assay studies
  • Cell cycle analysis
For information on Baseclick kits containing all the reagents for the assays see: Baseclick kits

For a listing of the Baseclick kits see: Baseclick kits

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Muta. 1B - Repr. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Detection of S-phase cell cycle progression using 5-ethynyl-2?-deoxyuridine incorporation with click chemistry, an alternative to using 5-bromo-2?-deoxyuridine antibodies
SB Buck
Biotechniques, 44, 927-929 (2008)
Quantification of cell cycle kinetics by EdU (5-ethynyl-2?-deoxyuridine)-coupled-fluorescence-intensity analysis
PD Pereira
Oncotarget, 8, 40514-40514 (2017)
Timothy J Mead et al.
Methods in molecular biology (Clifton, N.J.), 1130, 233-243 (2014-02-01)
Assessing cell proliferation in situ is an important phenotyping component of skeletal tissues from development to adult stages and disease. Various methods exist including immunostaining for proteins and protein modifications associated with specific steps of the cell cycle, but the
Site-directed spin-labeling of nucleic acids by click chemistry: detection of abasic sites in duplex DNA by EPR spectroscopy.
Jakobsen A, et al.
Journal of the American Chemical Society, 132(30), 10424-10428 (2010)
Synthesis, susceptibility to enzymatic phosphorylation, cytotoxicity and in vitro antiviral activity of lipophilic pyrimidine nucleoside/carborane conjugates.
Bialek-Pietras M, et al.
Journal of Organometallic Chemistry, 865, 166-172 (2018)

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