Ethynyl deoxyuridine

An acetylenic side chain in 5-ethynyl-2 -deoxyuridine or its O-acetyl derivative is converted by this method into a new pyridazine ring (86JOC950). Intramolecular cycloaddition of 1,2,4,5-tetrazines with acetylenic side chain has been used to prepare various condensed heterocyclic rings (32) (85TL4355 86TL2747 87CZ16 88JOC1415). 

Fig. 8 CuAAC reaction for in vivo labeling of DNA and RNA. a Schematic representation for in vivo fluorescent labeling of DNA and RNA molecules using metaboUcally incorporated EdU (or EU) and CuAAC reaction, b Detection of vims infection using the ceU-selective incorporation of dF-EdU and CuAAC reaction [102-104]. CuAAC copper(I)-catalyzed azide-aUcyne cycloaddition, EdU 5-ethynyl-2-deoxyuridine, EU 5-ethynyluridine, dF-EdU 2 -deoxy-2, 2 -difluoro-5-ethynyluridine...

The utilization of metabolic probes is a key strategy for the decryption of intracellular life processes. Luedtke and co-workers developed a vinyl-decorated deoxyuridine ll(VdU) that was able to be incorporated by endogenous enzymes into DNA synthesis and visualized by fluorescent tetrazine conjugates [55]. Additionally, VdU displayed lowered cytotoxicity and caused less DNA damage and cell cycle arrest compared to other clickable metabolic nucleic probes such as 5-ethynyl-2 -deoxyuridine (Fig. 3). 

Fig. 4 Metabolic DNA labeling using alkyne- or alkene-modified nucleosides. A 5-Ethynyl-2 -deoxyuridine (EdU) [153], (2 S)-2 -deoxy-2 -fluoro-5-ethynyluridine (F-ara-EdU) [160] and 5-vinyl-2 -deoxyuridine (VdU) [167], B Labeling strategy cells are incubated with the alkyne-modified nucleoside EdU, which is incorporated into the cellular genome in proliferating cells. Subsequently, the cells are fixed, permeabilized and components for the Cu -mediated azide alkyne cUck reaction with flumescent azides are added. Detection can be carried out by flow cytometry or fluorescence microscopy...

Alkyne-modilied libraries containing 5-ethynyl-2 -deoxyuridine [12] (EdU, Fig. 4A) instead of thymidine are prepared. Functionalization of the library is achieved by copper-catalyzed click reaction with azide containing compounds. As a proof of principle, 3-(2-azidoethyl)indole was used and successful selection was performed against cycle 3 GFP [175]. The amplification step after selection is carried out in the presence of EdU to restore an enriched alkyne-modified library for subsequent rounds of selection. At this point, correct amplification of the functionalized template strand by DNA polymerases is stiU a requirement for successful selection, and can restrict the size of the azide-modified compounds used. 

Zeng C, Pan F, Jones LA, Lim MM, Griffin EA, Sheline Yl, Mintun MA, Holtzman DM, Mach RH (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 1319 21-32. doi 10.1016. brainres.2009.12.092... 

Diermeier-Daucher S, Clarke ST, HiU D, Vollmann-Zwerenz A, Bradford JA, Brockhoff G (2009) Cell type specific appUcabilify of 5-ethynyl-2 -deoxyuridine (EdU) for dynamic proliferation assessment in flow cytometry. Cytometry Part A J Int Soc Anal Cytol 75(6) 535-546. doi 10.1002/ cyto.a.20712... 

Aminouridine, 5-vinyl-2 -deoxyuridine, 5-ethynyl-2 -deoxyuridine, 5-nitro-l-05-D-riburonosyl)uracil, uridine 5 -methylphosphate. ... 

C11H12N2O5, 5-Ethynyl-2 -deoxyuridine, 44B, 422 CliHi3CI2N3O3, 2-(4-0-Acetyl-2,3-dideoxy-p-L-glycero-pent-2-enopyranosyl)-5,6-dichlorobenzotria2ole, 39B, 335 C11HHCIN3O5, 3,N -Ethenocytidine hydrochloride, 42B, 344 5-Vinyl-2 -deoxyuridine, 44B, 422 p-5-Acetyl-2 -deoxyuridine, 46B, 463 a-5-Acetyl-2 -deoxyuridine, 43B, 578 2 ,3 -0-Methoxymethyleneuridine, 43B, 579... 

Synthesis of [2-]4C]-iabeiied 2,2-anhydrouridine (264) 2-deoxyuridine derivatives (265) and 5-ethynyl- and 5-ethyl-2-deoxyuridine (266)... 

Standard procedures have been employed in the preparation of various 5-substituted 2 -deoxyuridines, > - including the 5-ethynyl and 5-methyl derivatives, 5-cyclopropyluridine, the 5-(fluoroalkyloxymethyl)uridines (408), and the pyridine nucleosides (409) and (410). The pyridine nucleosides... 

Starting from 5-iododeoxyuridine, Hurley and Tor synthesized 1,10-phenanthroline-labeled nucleosides, containing a [(bipy)2M(3-ethynyl-l,10-phenanthroline)] (M=Ru, Os) moiety covalently attached to the 5 position of the 2 -deoxyuridine (Scheme 5). Both complexes exhibited a fully reversible electrochemistry with 1/2=0.993 V for Ru + + and 0.560 V for (vs. Ag/Ag+, in... 

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