Bioorthogonal Fluorescence Turn‐On Labeling Based on Bicyclononyne−Tetrazine Cycloaddition Reactions that Form Pyridazine Products

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Abstract: 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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Bioorthogonal Fluorescence Turn‐On Labeling Based on Bicyclononyne−Tetrazine Cycloaddition Reactions that Form Pyridazine Products ; volume:84 ; number:5 ; year:2019 ; pages:493-497 ; extent:5
ChemPlusChem ; 84, Heft 5 (2019), 493-497 (gesamt 5)

Creator: Siegl, Sebastian J.
Galeta, Juraj
Dzijak, Rastislav
Dračínský, Martin
Vrabel, Milan

DOI: 10.1002/cplu.201900176

URN: urn:nbn:de:101:1-2022081405420607367963

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:36 AM CEST

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Siegl, Sebastian J.
Galeta, Juraj
Dzijak, Rastislav
Dračínský, Martin
Vrabel, Milan

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Bioorthogonal Fluorescence Turn‐On Labeling Based on Bicyclononyne−Tetrazine Cycloaddition Reactions that Form Pyridazine Products

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