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Strain-Promoted Cycloaddition of Cyclopropenes with o-Quinones: A Rapid Click Reaction.

ABSTRACT: Novel click reactions are of continued interest in fields as diverse as bio-conjugation, polymer science and surface chemistry. Qualification as a proper "click" reaction requires stringent criteria, including fast kinetics and high conversion, to be met. Herein, we report a novel strain-promoted cycloaddition between cyclopropenes and o-quinones in solution and on a surface. We demonstrate the "click character" of the reaction in solution and on surfaces for both monolayer and polymer brush functionalization.

SUBMITTER: Gahtory D

PROVIDER: S-EPMC6099469 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Strain-Promoted Cycloaddition of Cyclopropenes with o-Quinones: A Rapid Click Reaction.

Gahtory Digvijay D Sen Rickdeb R Kuzmyn Andriy R AR Escorihuela Jorge J Zuilhof Han H

Angewandte Chemie (International ed. in English) 20180417 32

Novel click reactions are of continued interest in fields as diverse as bio-conjugation, polymer science and surface chemistry. Qualification as a proper "click" reaction requires stringent criteria, including fast kinetics and high conversion, to be met. Herein, we report a novel strain-promoted cycloaddition between cyclopropenes and o-quinones in solution and on a surface. We demonstrate the "click character" of the reaction in solution and on surfaces for both monolayer and polymer brush fun ...[more]

PMID: 29542846

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F-18 Labeled RGD Probes Based on Bioorthogonal Strain-Promoted Click Reaction for PET Imaging.

Project description:A series of fluorine-substituted monomeric and dimeric cRGD peptide derivatives, such as cRGD-ADIBOT-F (ADIBOT = azadibenzocyclooctatriazole), di-cRGD-ADIBOT-F, cRGD-PEG5-ADIBOT-F, and di-cRGD-PEG5-ADIBOT-F, were prepared by strain-promoted alkyne azide cycloaddition (SPAAC) reaction of the corresponding aza-dibenzocyclooctyne (ADIBO) substituted peptides with a fluorinated azide 3. Among these cRGD derivatives, di-cRGD-PEG5-ADIBOT-F had the highest binding affinity in a competitive binding assay compared to other derivatives and even the original cRGDyk. On the basis of the in vitro study results, di-cRGD-PEG5-ADIBOT-(18)F was prepared from a SPAAC reaction with (18)F-labeled azide and subsequent chemo-orthogonal scavenger-assisted separation without high performance liquid chromatography (HPLC) purification in 92% decay-corrected radiochemical yield (dcRCY) with high specific activity for further in vivo positron emission tomography (PET) imaging study. In vivo PET imaging study and biodistribution data showed that this radiotracer allowed successful visualization of tumors with good tumor-to-background contrast and significantly higher tumor uptake compared to other major organs.

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Rapid and Complete Surface Modification with Strain-Promoted Oxidation-Controlled Cyclooctyne-1,2-Quinone Cycloaddition (SPOCQ).

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Strain-Promoted Catalyst-Free Click Chemistry for Rapid Construction of (64)Cu-Labeled PET Imaging Probes.

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Project description: Not available

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Origin of Orthogonality of Strain-Promoted Click Reactions.

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Artificial Membrane Fusion Triggered by Strain-Promoted Alkyne-Azide Cycloaddition.

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Bioorthogonal prodrug activation driven by a strain-promoted 1,3-dipolar cycloaddition.

Project description:Due to the formation of hydrolysis-susceptible adducts, the 1,3-dipolar cycloaddition between an azide and strained trans-cyclooctene (TCO) has been disregarded in the field of bioorthogonal chemistry. We report a method which uses the instability of the adducts to our advantage in a prodrug activation strategy. The reaction of trans-cyclooctenol (TCO-OH) with a model prodrug resulted in a rapid 1,3-dipolar cycloaddition with second-order rates of 0.017 M-1 s-1 and 0.027 M-1 s-1 for the equatorial and axial isomers, respectively, resulting in release of the active compound. 1H NMR studies showed that activation proceeded via a triazoline and imine, both of which are rapidly hydrolyzed to release the model drug. Cytotoxicity of a doxorubicin prodrug was restored in vitro upon activation with TCO-OH, while with cis-cyclooctenol (CCO-OH) no activation was observed. The data also demonstrates the potential of this reaction in organic synthesis as a mild orthogonal protecting group strategy for amino and hydroxyl groups.

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Rapid conjugation of nanoparticles, proteins and siRNAs to microbubbles by strain-promoted click chemistry for ultrasound imaging and drug delivery.

Project description:A new strategy using catalyst-free strain-promoted alkyne-azide cycloaddition (SPAAC) "click" chemistry for the ligation of anti-cancer drug-loaded nanoparticles, functionalized proteins, and siRNA conjugated micelles to microbubbles (MB) was established. The results showed fast ligation within 5 min without sacrificing microbubble size and density. The ultrasound test showed good imaging abilities of the microbubbles after functionalization. This microbubble-therapeutic SPAAC "click" conjugation developed in the current study involves no toxic catalyst or initiator, has ultra-fast reaction speed, and is versatile for the ligation of various anti-cancer or therapeutic agents to microbubbles. These advantages render the SPAAC click strategy promising for broad applications in ultrasound-guided imaging and therapeutic delivery.

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