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5-Ethynyl-2'-deoxyuridine (Synonyms: 5-EdU, EdU, 2'-deoxy-5-Ethynyluridine)

Catalog No.GC42504

5-ethynyl-2′-deoxyuridine (EdU), as a thymidine analoghas, a terminal alkyne group replacing a methyl group at the 5 position of the pyrimidine ring and can be readily incorporated into DNA during synthesis[1].

Products are for research use only. Not for human use. We do not sell to patients.

5-Ethynyl-2'-deoxyuridine Chemical Structure

Cas No.: 61135-33-9

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10mM (in 1mL DMSO)
$29.00
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50mg
$26.00
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100mg
$46.00
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250mg
$91.00
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500mg
$147.00
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Protocol

Cell experiment [1]:

Cell lines

HeLa cells

Preparation Method

HeLa cells were incubated with either 10 µM EdU or 10 µM EdC for 4 h. Then, the detection of EdU and DNA using DAPI was performed.

Reaction Conditions

10 µM; 4h

Applications

The result shown approximately 75% of the cells contained a signal corresponding to the localization of incorporated EdU.

Animal experiment [2]:

Animal models

bird

Preparation Method

In order to label mitotically active supporting cells, a single, subcutaneous injection of EdU (50 mg/kg) in sterile, phosphate buffered saline (PBS, pH 7.4) was administered to each bird 72h after the gentamicin injection.

Dosage form

50 mg/kg; s.c.

Applications

When EdU is injected at 72h and allowed to incorporate for 4h, some of the supporting cells that first entered S phase around 65h are labeled with EdU at the end of their S phase. They are able to reach the mitotic phase and some even divide during this time.

References:

LigasovÁ A, et al. Dr Jekyll and Mr Hyde: a strange case of 5-ethynyl-2'-deoxyuridine and 5-ethynyl-2'-deoxycytidine. Open Biol. 2016 Jan;6(1):150172.
Kaiser CL, et al. 5-Ethynyl-2'-deoxyuridine labeling detects proliferating cells in the regenerating avian cochlea. Laryngoscope. 2009 Sep;119(9):1770-5.

Background

5-ethynyl-2′-deoxyuridine (EdU), as a thymidine analoghas, a terminal alkyne group replacing a methyl group at the 5 position of the pyrimidine ring and can be readily incorporated into DNA during synthesis[1]. EdU is a inhibitor of the cell growth of human breast cancer cells (MCF-7 and MDA-MP-231) with the IC50 of 0.4 μM for MCF-7 cells and 4.4 μM for MDA-MB-231 cells[2].

In vitro, 10 μMEdU induced gamma-H2AX foci for 51D1 and KO40 in CHO cells for DNA damage responses[3]. In vitro experiment it shown that A549 cells were treated with 20 μM EdU for 6 h increased the level of expression of γH2AX and ATM-S1981P by 88% and 116%, respectively[4].

In vivo efficacy test it shown that femalJKe mice were administrated 10, 20, 50, 100 or 200 mg/kg EdU intraperitoneally, there is an increase in the number of EdU positive cells in the DG slightlyin a dose-dependent manner[5]In vivo, few EdU-positive cells were observed in Wistar and GK rats at a dose of 5 mg/kg and 25 mg/kg EdU intraperitoneally. Prominent EdU-positive cells were observed in Wistar and GK rats at a dose of 100 mg/kg and 200 mg/kg, respectively[6]In vivo, use of 5-Ethynyl-2'-deoxyuridine (EdU) incorporation to in vivo monitor T lymphocyte proliferation by flow cytometry with an adoptive transfer model. The result shown that the percentage of EdU-positive cells increased in a dose-dependent manner, and the saturated dose of EdU was 20mg/kg. Intraperitoneal and intravenous injection had no differences in lymphocyte proliferation detection with EdU in vivo[7].

References:

[1] Kaiser CL, et al. 5-Ethynyl-2'-deoxyuridine labeling detects proliferating cells in the regenerating avian cochlea. Laryngoscope. 2009 Sep;119(9):1770-5.

[2] Meneni S, et al. (2007) 5-Alkynyl-2′-deoxyuridines: chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells. Bioorg Med Chem 15: 3082–3088.

[3] Haskins JS, et al. Evaluating the Genotoxic and Cytotoxic Effects of Thymidine Analogs, 5-Ethynyl-2'-Deoxyuridine and 5-Bromo-2'-Deoxyurdine to Mammalian Cells. Int J Mol Sci. 2020 Sep 10;21(18):6631.

[4] Zhao H, et al. DNA damage signaling, impairment of cell cycle progression, and apoptosis triggered by 5-ethynyl-2'-deoxyuridine incorporated into DNA. Cytometry A. 2013 Nov;83(11):979-88.

[5] Zeng C, et al. Evaluation of 5-ethynyl-2'-deoxyuridine staining as a sensitive and reliable method for studying cell proliferation in the adult nervous system. Brain Res. 2010 Mar 10;1319:21-32.

[6] Guo J, Li D, et al. Detecting DNA synthesis of neointimal formation after catheter balloon injury in GK and in Wistar rats: using 5-ethynyl-2'-deoxyuridine. Cardiovasc Diabetol. 2012 Dec 13;11:150.

[7] Sun X, Zhang C, et al. Flow cytometric analysis of T lymphocyte proliferation in vivo by EdU incorporation. Int Immunopharmacol. 2016 Dec;41:56-65.

Chemical Properties

Cas No. 61135-33-9 SDF
Synonyms 5-EdU, EdU, 2'-deoxy-5-Ethynyluridine
Canonical SMILES O=C(NC(C(C#C)=C1)=O)N1[C@H]2C[C@H](O)[C@@H](CO)O2
Formula C11H12N2O5 M.Wt 252.2
Solubility DMF: 20 mg/mL,DMSO: 20 mg/mL; Water: 8 mg/mL (31.72 mM; ultrasonic and warming and heat to 37°C) Storage 4°C, protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 3.9651 mL 19.8255 mL 39.6511 mL
5 mM 0.793 mL 3.9651 mL 7.9302 mL
10 mM 0.3965 mL 1.9826 mL 3.9651 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 34 reference(s) in Google Scholar.)

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