Rigid tetrazine fluorophore conjugates with fluorogenic properties in the inverse electron demand Diels-Alder reaction

• Verfasst von: Wieczorek, Achim [VerfasserIn]
• Verfasst von: Buckup, Tiago [VerfasserIn]
• Verfasst von: Wombacher, Richard [VerfasserIn]
• Titel: Rigid tetrazine fluorophore conjugates with fluorogenic properties in the inverse electron demand Diels-Alder reaction
• Verf.angabe: Achim Wieczorek, Tiago Buckup and Richard Wombacher
• E-Jahr: 2014
• Jahr: 23 April 2014
• Umfang: 9 S.
• Fussnoten: Gesehen am 30.09.2020
• Titel Quelle: Enthalten in: Organic & biomolecular chemistry
• Ort Quelle: Cambridge : Royal Society of Chemistry, 2003
• Jahr Quelle: 2014
• Band/Heft Quelle: 12(2014), 24, Seite 4177-4185
• ISSN Quelle: 1477-0539
• DOI: doi:10.1039/C4OB00245H
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1734031581

Abstract

1,2,4,5-Tetrazine fluorophore derivatives with structurally rigid molecular designs were synthesized using Sonogashira and Stille cross-coupling as well as copper-catalyzed azide-alkyne cycloaddition. The synthesized bichromophoric systems exhibit low fluorescence quantum yields due to quenching by the tetrazine. The extent of fluorescence quenching observed for those systems was shown to depend on the distance between the fluorophore and the tetrazine. The decreased fluorescence is “turned on” by conversion of the tetrazine in the inverse electron demand Diels-Alder cycloaddition. Time resolved spectroscopy indicated resonance energy transfer between BODIPY and the tetrazine as the underlying quenching mechanism. The synthesized conjugates were successfully applied in protein labeling experiments.