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Bioorthogonal Fluorescence Turn‐On Labeling Based on Bicyclononyne−Tetrazine Cycloaddition Reactions that Form Pyridazine Products
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Bioorthogonal Fluorescence Turn‐On Labeling Based on Bicyclononyne−Tetrazine Cycloaddition Reactions that Form Pyridazine Products
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Bioorthogonal Fluorescence Turn‐On Labeling Based on Bicyclononyne−Tetrazine Cycloaddition Reactions that Form Pyridazine Products
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Journal Article
Bioorthogonal Fluorescence Turn‐On Labeling Based on Bicyclononyne−Tetrazine Cycloaddition Reactions that Form Pyridazine Products
2019
Overview
Fluorogenic bioorthogonal reactions enable visualization of biomolecules with excellent signal‐to‐noise ratio. A bicyclononyne−tetrazine ligation that produces fluorescent pyridazine products has been developed. In stark contrast to previous approaches, the formation of the dye is an inherent result of the chemical reaction and no additional fluorophores are needed in the reagents. The crucial structural elements that determine dye formation are electron‐donating groups present in the starting tetrazine unit. The newly formed pyridazine fluorophores show interesting photophysical properties the fluorescence intensity increase in the reaction can reach an excellent 900‐fold. Model imaging experiments demonstrate the application potential of this new fluorogenic bioorthogonal reaction. Turning on: A bicyclononyne dienophile reacts with 1,2,4,5‐tetrazines bearing electron‐donating groups to form fluorescent pyridazine products in an inverse electron‐demand Diels‐Alder reaction (iEDDA). The fluorescence turn‐on properties are preserved in biological systems and can be applied to bioimaging. In combination with the fluorogenic trans‐cyclooctene−tetrazine cycloaddition reaction, the reaction enables one‐step two‐color labeling using a single tetrazine as the activator.
Publisher
John Wiley and Sons Inc
