ArticleThe Journal of organic chemistry2014
Sequential "click" - "photo-click" cross-linker for catalyst-free ligation of azide-tagged substrates.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Visible and near-infrared light-induced photoclick reactions.Nature reviews. Chemistry · 2024Review
- Clickable Polysaccharides for Biomedical Applications: A Comprehensive Review.Progress in polymer science · 2022Article
- Development of Dual Receptor Enhanced Pre-Targeting Strategy-A Novel Promising Technology for Immuno-Positron Emission Tomography Imaging.Advanced therapeutics · 2021Article
- Bioorthogonal Reactions of Triarylphosphines and Related Analogues.Chemical reviews · 2021Review
- Light-Triggered Click Chemistry.Chemical reviews · 2021Review
- Photoclick Chemistry: A Bright Idea.Chemical reviews · 2021Review
- Reversible Functionalization of Clickable Polyacrylamide Gels with Protein and Graft Copolymers.Advanced functional materials · 2020Article
- Photo-Click-Facilitated Screening Platform for the Development of Hetero-Bivalent Agents with High Potency.The Journal of organic chemistry · 2020Article
- Photo-induced and Rapid Labeling of Tetrazine-Bearing Proteins via Cyclopropenone-Caged Bicyclononynes.Angewandte Chemie (International ed. in English) · 2019Review
- Facile Quenching and Spatial Patterning of Cylooctynes via Strain-Promoted Alkyne-Azide Cycloaddition of Inorganic Azides.Bioconjugate chemistry · 2017Article
- Sequential Photochemistry of Dibenzo[a,e]dicyclopropa[c,g][8]annulene-1,6-dione: Selective Formation of Didehydrodibenzo[a,e][8]annulenes with Ultrafast SPAAC Reactivity.The Journal of organic chemistry · 2016Article
- Photo-Triggered Click Chemistry for Biological Applications.Topics in current chemistry (Cham) · 2016Review
- Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking.Chemical communications (Cambridge, England) · 2016Article
- Highly selective molybdenum ONO pincer complex initiates the living ring-opening metathesis polymerization of strained alkynes with exceptionally low polydispersity indices.Journal of the American Chemical Society · 2015Article
- Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles.PloS one · 2015Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
Heterobifunctional linker allows for selective catalyst-free ligation of two different azide-tagged substrates via strained-promoted azide-alkyne cycloaddition (SPAAC). The linker contains an azadibenzocyclooctyne (ADIBO) moiety on one end and a cyclopropenone-masked dibenzocyclooctyne (photo-DIBO) group on the other. The first azide-derivatized substrate reacts only at the ADIBO end of the linker as the photo-DIBO moiety is azide-inert. After the completion of the first SPAAC step, photo-DIBO is activated by brief exposure to 350 nm light from a fluorescent UV lamp. The unmasked DIBO group then reacts with the second azide-tagged substrate. Both click reactions are fast (k = 0.4 and 0.07 M(-1) s(-1), respectively) and produce quantitative yield of ligation in organic solvents or aqueous solutions. The utility of the new cross-linker has been demonstrated by conjugation of azide functionalized bovine serum albumin (azido-BSA) with azido-fluorescein and by the immobilization of the latter protein on azide-derivatized silica beads. The BSA-bead linker was designed to incorporate hydrolytically labile fragment, which permits release of protein under the action of dilute acid. UV activation of the second click reaction permits spatiotemporal control of the ligation process.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.