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 (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

Different sources of media describe the Uses of 61135-33-9 differently. You can refer to the following data:
1. 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.
2. 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 kitsFor 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 
• 1066-54-2 trimethylsilylacetylene 
• 69075-43-0 5-Ethynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine 
• 151362-01-5 1-(2-deoxy-β-D-ribofuranosyl)-5-[2-(trimethylsilyl)ethynyl]uracil 
• 74-86-2 acetylene 
• 951-78-0 2'-deoxyuridine 
• 85267-60-3 1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-(trimethylsilylethynyl)uracil 
• 100021-00-9 1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-ethynyluracil 
• 1956-30-5 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine 
• 13030-62-1 3',5'-di-O-acetyl-2'-deoxyuridine 
• 59989-18-3 5-ethynyluracil 
• 50-89-5 thymidine 
• 78731-60-9 5-(1-Chloro-vinyl)-2,4-bis-trimethylsilanyloxy-pyrimidine 
• 61751-48-2 5-(1-chlorovinyl)-uracil 

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 
• 1002760-28-2 3-(2'-deoxy-β-D-ribofuranosyl)-6-(4-hydroxyphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2(3H)-one 
• 1159683-93-8 C₂₀H₂₀N₂O₅ 
• 1159683-94-9 C₂₁H₂₂N₂O₅ 
• 1159683-96-1 C₂₁H₂₂N₂O₅ 
• 1159683-97-2 C₂₂H₂₄N₂O₅ 
• 1159683-99-4 C₂₂H₂₄N₂O₅ 
• 1159683-91-6 C₂₀H₂₀N₂O₅ 
• 1050649-04-1 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridine 

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.).