61135-33-9

Basic information

• Product Name: 5-ETHYNYL-2'-DEOXYURIDINE
• Synonyms: 5-ETHYNYL-2'-DEOXYURIDINE;2’-deoxy-5-ethynyl-uridin;2’-deoxy-5-ethynyluridine;EYdU;5-Ethynyl-durd;Aids072372;Aids-072372;2'deoxyuridine, 5-ethynyl
• CAS NO: 61135-33-9
• Molecular Formula: C₁₁H₁₂N₂O₅
• Molecular Weight: 252.22
• EINECS: 500-100-4
• Mol File: 61135-33-9.mol
• Article Data: 33

Chemical Properties

• Melting Point: 199°C(lit.)
• Appearance: /
• Density: 1.55 g/cm³
• Refractive Index: 1.644
• Storage Temp.: -20°C
• Solubility: Soluble in DMSO (up to 10 mg/ml).
• PKA: 8.29±0.10(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.
• CAS DataBase Reference: 5-ETHYNYL-2'-DEOXYURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ETHYNYL-2'-DEOXYURIDINE(61135-33-9)
• EPA Substance Registry System: 5-ETHYNYL-2'-DEOXYURIDINE(61135-33-9)

Safety Data

• Hazard Codes: T
• Statements: 46-61
• Safety Statements: 53-45-24/25
• RTECS: YU7510000
• Hazardous Substances Data: 61135-33-9(Hazardous Substances Data)

Usage

Description

5-Ethynyl-2'-deoxyuridine (EdU) is a nucleoside analog that serves as a novel agent for fast and sensitive detection of DNA synthesis in vivo. It is incorporated into proliferating cells and can be detected with a fluorescent azide using click ligation. Unlike BrdU, EdU does not require sample fixation or DNA denaturation, making it a more efficient method for studying cell proliferation.
Used in Biomedical Research:
5-Ethynyl-2'-deoxyuridine is used as a probe for DNA synthesis in biomedical research for its ability to detect cell proliferation in a simpler workflow than anti-BrdU assays. It is particularly useful in studying cell proliferation in the central nervous system and can be combined with BrdU staining for double labeling of DNA synthesis.
Used in Tissue Culture and Living Organisms:
EdU is used as a toxic anti-metabolite for short-term DNA synthesis in tissue culture and living organisms where prolonged cell survival is not required. It has the potential to cause DNA instability, necrosis, and cell-cycle arrest, making it suitable for applications where temporary cell analysis is needed.
Used in Detection of Cell Proliferation:
5-Ethynyl-2'-deoxyuridine is used as a thymidine analog in the detection of cell proliferation. Its alkyne handle allows it to ligate with azide-containing fluorescent probes through a highly efficient click chemistry reaction. This feature enables the incorporation of EdU nucleoside into the DNA of cells either in culture or in animals without showing significant toxicity, offering a more straightforward method for detecting cell proliferation compared to traditional anti-BrdU assays.
For more information on Baseclick kits containing all the reagents for the assays, see: Baseclick kits
For a listing of the Baseclick kits, see: Baseclick kits

References

1) Salic and Mitchison (2008),?A chemical method for fast and sensitive detection of DNA synthesis in vivo; Proc. Natl. Acad. Sci. USA,?105?2415 2) Zeng?et al. (2010),?Evaluation of 5-ethynyl-2′-deoxyuridine staining as a sensitive and reliable method for studying cell proliferation in the adult nervous system; Brain Res.,?1319C?21

InChI: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

Upstream product

• 54-42-2 5-Iodo-2'-deoxyuridine 
• 74-86-2 acetylene 
• 59989-18-3 5-ethynyluracil 
• 50-89-5 thymidine 
• 13030-62-1 3',5'-di-O-acetyl-2'-deoxyuridine 
• 1956-30-5 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine 
• 100021-00-9 1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-ethynyluracil 
• 85267-60-3 1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-(trimethylsilylethynyl)uracil 
• 951-78-0 2'-deoxyuridine 
• 151362-01-5 1-(2-deoxy-β-D-ribofuranosyl)-5-[2-(trimethylsilyl)ethynyl]uracil 
• 78731-60-9 5-(1-Chloro-vinyl)-2,4-bis-trimethylsilanyloxy-pyrimidine 
• 61751-48-2 5-(1-chlorovinyl)-uracil 
• 117626-98-9 3'-Acetyl-2'-deoxy-5-ethynyl-5'-(4,4'-dimethoxytrityl)uridine 
• 117626-97-8 5'-O-(4,4'-dimethoxytrityl)-5-(1-phenyl-1H-1,2,3-triazol-4-yl)-2'-deoxyuridine 

Downstream Products

• 117626-97-8 5'-O-(4,4'-dimethoxytrityl)-5-(1-phenyl-1H-1,2,3-triazol-4-yl)-2'-deoxyuridine 
• 15176-29-1 edoxudine 
• 55520-67-7 5-vinyl-2'-deoxyuridine 
• 59090-41-4 5-acetyl-1-(2-deoxy-β-D-erythro-pentofuranosyl)uracil 
• 287980-23-8 5-vinyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine 
• 117626-80-9 Sodium; {[(2R,3S,5R)-5-(2,4-dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetate 
• 1374418-30-0 C₃₅H₂₉N₃O₅ 
• 1374418-24-2 C₃₃H₂₅N₃O₅ 
• 1374418-26-4 C₃₈H₃₅N₃O₅ 
• 1374418-27-5 C₃₉H₃₅N₃O₅ 
• 1374418-28-6 C₃₇H₃₃N₃O₅ 
• 1374418-29-7 C₃₇H₃₃N₃O₅ 

Relevant articles and documents

Phosphorylated 5-ethynyl-2′-deoxyuridine for advanced DNA labeling

The representative DNA-labeling agent 5-ethynyl-2′-deoxyuridine (EdU) was chemically modified to improve its function. Chemical monophosphorylation was expected to enhance the efficiency of the substrate in DNA polymerization by circumventing the enzymati

Synthesis of tricarbonyl rhenium and technetium complexes of a 5′-carboxamide 5-ethyl-2′-deoxyuridine for selective inhibition of herpes simplex virus thymidine kinase 1

Herpes simplex virus thymidine kinase type 1 (HSV1-TK) is frequently used as reporter protein in gene therapy. Our aim is to produce single photon emitting reporter probe based on technetium-99m. The synthesis of organometallic technetium and rhenium comp

Tropolone-Conjugated DNA: Fluorescence Enhancement in the Duplex

Tropolone (2-hydroxycyclohepta-2,4,6-triene-1-one and tautomer) is a non-benzenoid bioactive natural chromophore with pH-dependent fluorescence character and extraordinary metal binding affinities, especially with transition-metal ions Cu2+/Zn

Thermodynamic Reaction Control of Nucleoside Phosphorolysis

Nucleoside analogs represent a class of important drugs for cancer and antiviral treatments. Nucleoside phosphorylases (NPases) catalyze the phosphorolysis of nucleosides and are widely employed for the synthesis of pentose-1-phosphates and nucleoside analogs, which are difficult to access via conventional synthetic methods. However, for the vast majority of nucleosides, it has been observed that either no or incomplete conversion of the starting materials is achieved in NPase-catalyzed reactions. For some substrates, it has been shown that these reactions are reversible equilibrium reactions that adhere to the law of mass action. In this contribution, we broadly demonstrate that nucleoside phosphorolysis is a thermodynamically controlled endothermic reaction that proceeds to a reaction equilibrium dictated by the substrate-specific equilibrium constant of phosphorolysis, irrespective of the type or amount of NPase used, as shown by several examples. Furthermore, we explored the temperature-dependency of nucleoside phosphorolysis equilibrium states and provide the apparent transformed reaction enthalpy and apparent transformed reaction entropy for 24 nucleosides, confirming that these conversions are thermodynamically controlled endothermic reactions. This data allows calculation of the Gibbs free energy and, consequently, the equilibrium constant of phosphorolysis at any given reaction temperature. Overall, our investigations revealed that pyrimidine nucleosides are generally more susceptible to phosphorolysis than purine nucleosides. The data disclosed in this work allow the accurate prediction of phosphorolysis or transglycosylation yields for a range of pyrimidine and purine nucleosides and thus serve to empower further research in the field of nucleoside biocatalysis. (Figure presented.).