ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
Fluorogenic Strain-Promoted Alkyne-Diazo Cycloadditions.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 51 citations in OpenAlex.
- Photo-Triggered, Fast, and Fluorogenic Thiophene-Based Cycloalkynes for the Bioorthogonal Fluorescent Labeling of 1,3-Dipole-Tagged Molecules in No-Wash Conditions.Angewandte Chemie (International ed. in English) · 2026Article
- A Water-Soluble Fluorogenic Probe to Quantify Azide Concentrations in Biologically Relevant Environments.Biomacromolecules · 2026Article
- Azo-Povarov Cycloaddition ofThe Journal of organic chemistry · 2026Article
- Article
- Understanding the Ligand Influence in the Multistep Reaction of Diazoalkanes with Palladium Complexes Leading to Carbene-Aryl Coupling.Organometallics · 2025Article
- Balancing Brightness and Photobasicity: Modulating Excited-State Proton Transfer Pathways in Push-Pull Fluorophores for Biological Two-Photon Imaging.The journal of physical chemistry. A · 2024Article
- LiOMolecules (Basel, Switzerland) · 2023Article
- Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells.Chemical & biomedical imaging · 2023Review
- High Magnetic Anisotropy of a Square-Planar Iron-Carbene Complex.Inorganic chemistry · 2021Article
- Diazocarbonyl and Related Compounds in the Synthesis of Azoles.Molecules (Basel, Switzerland) · 2021Review
- Bioorthogonal Fluorescence Turn-On Labeling Based on Bicyclononyne-Tetrazine Cycloaddition Reactions that Form Pyridazine Products.ChemPlusChem · 2019Article
- Modern Synthetic Avenues for the Preparation of Functional Fluorophores.Angewandte Chemie (International ed. in English) · 2017Review
- Diazo Compounds: Versatile Tools for Chemical Biology.ACS chemical biology · 2016Review
- Rapid cycloaddition of a diazo group with an unstrained dipolarophile.Tetrahedron letters · 2016Article
Corrections and comments
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Authors and funding
3 authors at 3 institutions in 2 countries.
Funding
Abstract
Fluorogenic reactions, in which non- or weakly fluorescent reagents produce highly fluorescent products, are attractive for detecting a broad range of compounds in the fields of bioconjugation and material sciences. Herein, we report that a dibenzocyclooctyne derivative modified with a cyclopropenone moiety (Fl-DIBO) can undergo fast strain-promoted cycloaddition reactions under catalyst-free conditions with azides, nitrones, nitrile oxides, as well as mono- and disubstituted diazo-derivatives. Although the reaction with nitrile oxides, nitrones, and disubstituted diazo compounds gave cycloadducts with low quantum yield, monosubstituted diazo reagents produced 1H-pyrazole derivatives that exhibited an approximately 160-fold fluorescence enhancement over Fl-DIBO combined with a greater than 10,000-fold increase in brightness. Concluding from quantum chemical calculations, fluorescence quenching of 3H-pyrazoles, which are formed by reaction with disubstituted diazo-derivatives, is likely due to the presence of energetically low-lying (n,π*) states. The fluorogenic probe Fl-DIBO was successfully employed for the labeling of diazo-tagged proteins without detectable background signal. Diazo-derivatives are emerging as attractive reporters for the labeling of biomolecules, and the studies presented herein demonstrate that Fl-DIBO can be employed for visualizing such biomolecules without the need for probe washout.
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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.