Fluorogenic click reaction

Droumaguet, Céline Le; Wang, Chao; Wang, Qian

doi:10.1039/b901975h

Cited by 289 publications

(176 citation statements)

References 52 publications

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“…[47] An excellent recent review by Meldal and Tornoe describes CuAAC in great detail. [48] The design of the recent development of fluorogenic CuAAC reactions as well as their applications has been highlighted by Wang et al [49] [a] S. G. Agalave, Dr. S. R. Maujan, Dr. V. S. Pore Organic Chemistry Division National Chemical Laboratory Dr. Homi Bhabha Road, Pashan, Pune (India) Fax: (+ 91) 20-25902629 E-mail: vs.pore@ncl.res.in…”

Section: Reviews On Click Chemistrymentioning

confidence: 99%

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,167

508

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The copper(I)-catalyzed 1,2,3-triazole-forming reaction between azides and terminal alkynes has become the gold standard of click chemistry due to its reliability, specificity, and biocompatibility. Applications of click chemistry are increasingly found in all aspects of drug discovery; they range from lead finding through combinatorial chemistry and target-templated in vitro chemistry, to proteomics and DNA research by using bioconjugation reactions. The triazole products are more than just passive linkers; they readily associate with biological targets, through hydrogen-bonding and dipole interactions. The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.

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Section: Reviews On Click Chemistrymentioning

confidence: 99%

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Agalave

Maujan

Pore

2011

Chemistry An Asian Journal

1,167

508

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“…The most sensitive method for determination of reaction rate constants of cyclooctynes is by means of a reaction with a fluorogenic azide substrate [35]. By definition, a fluorogenic SPAAC process involves a reaction between a nonfluorescent alkyne and azide, allowing the ligation of two biomolecules to afford a highly fluorescent triazole product.…”

Section: Tools To Quantify Spaac Reaction Ratesmentioning

confidence: 99%

Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides

Dommerholt

Rutjes

Delft

2016

Cycloadditions in Bioorthogonal Chemistry

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A nearly forgotten reaction discovered more than 60 years ago-the cycloaddition of a cyclic alkyne and an organic azide, leading to an aromatic triazole-enjoys a remarkable popularity. Originally discovered out of pure chemical curiosity, and dusted off early this century as an efficient and clean bioconjugation tool, the usefulness of cyclooctyne-azide cycloaddition is now adopted in a wide range of fields of chemical science and beyond. Its ease of operation, broad solvent compatibility, 100 % atom efficiency, and the high stability of the resulting triazole product, just to name a few aspects, have catapulted this so-called strain-promoted azide-alkyne cycloaddition (SPAAC) right into the top-shelf of the toolbox of chemical biologists, material scientists, biotechnologists, medicinal chemists, and more. In this chapter, a brief historic overview of cycloalkynes is provided first, along with the main synthetic strategies to prepare cycloalkynes and their chemical reactivities. Core aspects of the strain-promoted reaction of cycloalkynes with azides are covered, as well as tools to achieve further reaction acceleration by means of modulation of cycloalkyne structure, nature of azide, and choice of solvent.

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“…This reaction has been extensively used in materials development [6][7][8][9], polymer synthesis [10,11], dendrimer synthesis [12][13][14][15][16] and drug discovery [17][18][19]. CuAAC reaction serves as a great tool for bioconjugation applications [20][21][22][23][24][25][26][27][28][29], mainly due to (i) facile synthesis and easy incorporation of alkyne and azide moieties into biomolecular frameworks, (ii) compatibility to other functionalities yielding highly specific products, (iii) compatibility to water which is crucial for biomolecular systems, (iv) mild reaction conditions which will help maintaining the properties of biomolecules, and (v) stability of the resulting triazole ring to the hydrolytic cleavage, oxidation and reduction [2,3,9].…”

Section: Introductionmentioning

confidence: 99%

Crosslinking of viral nanoparticles with “clickable” fluorescent crosslinkers at the interface

et al. 2010

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Cu (I) catalyzed alkyne-azide cycloaddition (CuAAC) reaction, a typical "click" reaction, is one of the modular synthetic approaches which has been broadly used in various organic syntheses, medicinal chemistry, materials development and bioconjugation applications. We have for the first time synthesized two dialkyne derivatized fluorescent crosslinkers which could be applied to crosslink two biomolecules using CuAAC reaction. Turnip yellow mosaic virus, a plant virus with unique structural and chemical properties, was used as a prototypical scaffold to form a 2D single layer at the interface of two immiscible liquids and crosslinked with these two linkers by the CuAAC reaction. Upon crosslinking, the fluorescence of both linkers diminished, likely due to the distortion of the polymethylene backbone, which therefore could be used to indicate the completion of the reaction.

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Fluorogenic click reaction

Cited by 289 publications

References 52 publications

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Click Chemistry: 1,2,3‐Triazoles as Pharmacophores

Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides

Crosslinking of viral nanoparticles with “clickable” fluorescent crosslinkers at the interface

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