5-ETHYNYL-2'-DEOXYURIDINE Chemical Properties

Melting point:

199°C(lit.)

Density 

1.55±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in DMSO (up to 10 mg/ml).

pka

8.29±0.10(Predicted)

form 

powder

color 

White or off-white

Appearance

light beige to light brown solid

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.

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

InChIKey

CDEURGJCGCHYFH-DJLDLDEBSA-N

SMILES

OC[C@H]1O[C@@H](N2C=C(C#C)C(=O)NC2=O)C[C@@H]1O

CAS DataBase Reference

61135-33-9

Safety Information

Hazard Codes 

T

Risk Statements 

46-61

Safety Statements 

53-45-24/25

RTECS 

YU7510000

HS Code 

29349990

5-ETHYNYL-2'-DEOXYURIDINE Usage And Synthesis

Description

5-Ethynyl-2′-deoxyuridine (61135-33-9) is a novel agent for fast and sensitive detection of DNA synthesis?in vivo.1 5-EdU is incorporated into proliferating cells followed by detection with a fluorescent azide using click ligation.1 In contrast to the use of BrdU, the new method does not require sample fixation or DNA denaturation. 5-Ethynyl-2′-deoxyuridine may be used for studying cell proliferation in the central nervous system and may be combined with BrdU staining in a novel protocol allowing for double labeling of DNA synthesis.2

Uses

5-Ethynyl-2’deoxyuridine is a extensively used nucleoside analog used as a probe for DNA synthesis. However, 5-Ethynyl-2’deoxyuridine is a toxic anti-metabolite, which potentially causes DNA instabi liy, necrosis and cell-cycle arrest, therefore it is often used for short-term DNA synthesis in tissue culture and living organisms where prolonged cell survival is not required.

Uses

5-Ethynyl-2′-deoxyuridine (EdU) is a thymidine analog that can be incorporated into replicating DNA for detection of cell proliferation. It has an alkyne handle that can ligate with azide-containing fluorescent probes through a highly efficient click chemistry reaction. EdU nucleoside can be incorporated into the DNA of cells either in culture or in animals without showing significant toxicity. The assay offers a simpler workflow for detecting cell proliferation than anti-BrdU assays.

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

storage

Store at -20°C

References

[1] ADRIAN SALIC  Timothy J M. A chemical method for fast and sensitive detection of DNA synthesis in vivo.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2008, 105 7: 2415-2420. DOI:10.1073/pnas.0712168105
[2] CHENBO ZENG . Evaluation of 5-ethynyl-2′-deoxyuridine staining as a sensitive and reliable method for studying cell proliferation in the adult nervous system[J]. Brain Research, 2010, 1319: Pages 21-32. DOI:10.1016/j.brainres.2009.12.092

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