5-Ethynyl-2'-deoxyuridine

Base Information

• Chemical Name: 5-Ethynyl-2'-deoxyuridine
• CAS No.: 61135-33-9
• Molecular Formula: C11H12N2O5
• Molecular Weight: 252.227
• Hs Code.: 29349990
• European Community (EC) Number: 804-162-0
• UNII: G373S00W2J
• DSSTox Substance ID: DTXSID20976652
• Nikkaji Number: J59.519E
• Wikipedia: 5-Ethynyl-2%27-deoxyuridine,5-Ethynyl-2'-deoxyuridine
• Wikidata: Q4639590
• ChEMBL ID: CHEMBL222932
• Mol file: 61135-33-9.mol

Synonyms:2'-deoxy-5-ethynyluridine;5-ethynyl-2'-deoxyuridine

Chemical Property of 5-Ethynyl-2'-deoxyuridine

Chemical Property:

• Melting Point: 199°C(lit.)
• Refractive Index: 1.644
• PKA: 8.29±0.10(Predicted)
• PSA: 104.55000
• Density: 1.55 g/cm³
• LogP: -1.84140
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 10 mg/ml).
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 252.07462149
• Heavy Atom Count: 18
• Complexity: 463

Purity/Quality:

98%min ^*data from raw suppliers

5-Ethynyl-2’-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 46-61
• Safety Statements: 53-45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
• Isomeric SMILES: C#CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O
• 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. 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

Technology Process of 5-Ethynyl-2'-deoxyuridine

There total 30 articles about 5-Ethynyl-2'-deoxyuridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

1-(2-deoxy-β-D-ribofuranosyl)-5-[2-(trimethylsilyl)ethynyl]uracil (151362-01-5) → 2'-deoxy-5-ethynyluridine (61135-33-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In methanol; for 0.5h;

DOI:10.1021/jo00076a019

Reference yield: 79.0%

5-Ethynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine (69075-43-0) → 2'-deoxy-5-ethynyluridine (61135-33-9)

Guidance literature:

With sodium methylate; In methanol; at 60 ℃; for 4h;

DOI:10.1016/j.jorganchem.2006.10.011

Reference yield: 75.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + trimethylsilylacetylene (1066-54-2) → 2'-deoxy-5-ethynyluridine (61135-33-9)

Guidance literature:

5-Iodo-2'-deoxyuridine; trimethylsilylacetylene; With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

With potassium carbonate; In methanol; Inert atmosphere;

DOI:10.1002/cbic.201800822

upstream raw materials:

5-ethynyltrimethylsilyl-3',5'-di-O-p-toluyl-2'-deoxyuridine

5-(1-chlorovinyl)-2'-deoxy-3',5'-di-O-(p-toluoyl)uridine

1-(2-deoxy-β-D-ribofuranosyl)-5-[2-(trimethylsilyl)ethynyl]uracil

5-Iodo-2'-deoxyuridine

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-5-(1-phenyl-1H-1,2,3-triazol-4-yl)-2'-deoxyuridine

edoxudine

5-vinyl-2'-deoxyuridine

5-acetyl-1-(2-deoxy-β-D-erythro-pentofuranosyl)uracil

Refernces

• 1、 Slaví?ková, Michaela,Janou?ková, Martina,?imonová, Anna,Cahová, Hana,Kambová, Milada,?anderová, Hana,Krásny, Libor,Hocek, Michal. "Turning Off Transcription with Bacterial RNA Polymerase through CuAAC Click Reactions of DNA Containing 5-Ethynyluracil". . p. 8311 - 8314. Retrieved 2018.
• 2、 Cristofoli, Walter A.,Wiebe, Leonard I.,De Clercq, Erik,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan,Knaus, Edward E.. "5-Alkynyl analogs of arabinouridine and 2′-deoxyuridine: Cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells". . p. 2851 - 2857. Retrieved 2007.
• 3、 Zhao, Xuan,Zhao, Long,Xiao, Qiuyun,Xiong, Hai. "Intermolecular hydrogen-bond interaction to promote thermoreversible 2'-deoxyuridine-based AIE-organogels". supporting information. p. 1363 - 1367. Retrieved 2020/10/27.