Literature DB >> 15548086

A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes.

Krishnamoorthy Sivakumar1, Fang Xie, Brandon M Cash, Su Long, Hannah N Barnhill, Qian Wang.   

Abstract

Copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of nonfluorescent 3-azidocoumarins and terminal alkynes afforded intense fluorescent 1,2,3-triazole products. The mild condition of this reaction allowed us to construct a large library of pure fluorescent coumarin dyes. Since both azide and alkyne are quite inert to biological systems, this reaction has potential in bioconjugation and bioimaging applications. [reaction: see text]

Entities:  

Year:  2004        PMID： 15548086     DOI： 10.1021/ol047955x

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  96 in total

1.  Bioorthogonal reaction pairs enable simultaneous, selective, multi-target imaging.

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Journal:  Angew Chem Int Ed Engl       Date:  2011-12-12       Impact factor: 15.336

2.  α-Azido ketones. Part 7: synthesis of 1,4-disubstituted triazoles by the "click" reaction of various terminal acetylenes with phenacyl azides or α-azidobenzo(hetera)cyclanones.

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Journal:  Mol Divers       Date:  2012-02-04       Impact factor: 2.943

3.  Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging.

Authors:  Rachel C Steinhardt; Jessica M O'Neill; Colin M Rathbun; David C McCutcheon; Miranda A Paley; Jennifer A Prescher
Journal:  Chemistry       Date:  2016-01-19       Impact factor: 5.236

4.  A FRET-based fluorogenic phosphine for live-cell imaging with the Staudinger ligation.

Authors:  Matthew J Hangauer; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions.

Authors:  Xinghai Ning; Jun Guo; Margreet A Wolfert; Geert-Jan Boons
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  A fluorogenic probe for the catalyst-free detection of azide-tagged molecules.

Authors:  Frédéric Friscourt; Christoph J Fahrni; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2012-11-02       Impact factor: 15.419

7.  Development and Characterization of FLT3-Specific Curcumin-Loaded Polymeric Micelles as a Drug Delivery System for Treating FLT3-Overexpressing Leukemic Cells.

Authors:  Singkome Tima; Siriporn Okonogi; Chadarat Ampasavate; Chad Pickens; Cory Berkland; Songyot Anuchapreeda
Journal:  J Pharm Sci       Date:  2016-10-14       Impact factor: 3.534

8.  Potato virus X as a novel platform for potential biomedical applications.

Authors:  Nicole F Steinmetz; Marianne E Mertens; Rebecca E Taurog; John E Johnson; Ulrich Commandeur; Rainer Fischer; Marianne Manchester
Journal:  Nano Lett       Date:  2010-01       Impact factor: 11.189

9.  Copper-Catalyzed Azide-Alkyne Click Chemistry for Bioconjugation.

Authors:  Stanislav I Presolski; Vu Phong Hong; M G Finn
Journal:  Curr Protoc Chem Biol       Date:  2011-12-01

10.  Discrimination of colon cancer stem cells using noncanonical amino acid.

Authors:  Xinrui Duan; Honglin Li; Hexin Chen; Qian Wang
Journal:  Chem Commun (Camb)       Date:  2012-07-30       Impact factor: 6.222
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