I Bind It That Way : Bioorthogonal Unmasking of Pro Fluorescent Quinone Methides

Kern, Dóra and Lövei, Allegra and Kele, Péter and Kormos, Attila (2024) I Bind It That Way : Bioorthogonal Unmasking of Pro Fluorescent Quinone Methides. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 27 (34). ISSN 1434-193X

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Abstract

Proof-of-concept studies for the bioorthogonally controlled generation of pro-fluorescent quinone-methides are presented here. The novel concept relies on a click-to-release tetrazine unit that chemically cages a pro-fluorescent quinone methide precursor. On a synthetically readily accessible model compound we demonstrate that IEDDA reaction of the tetrazine with a TCO leads to the liberation of a pro-fluorescent quinone methide, which is readily captured by nearby nucleophiles to form a fluorescent scaffold. Unlike in previous approaches to access bioorthogonally activatable fluorogenic probes, where the tetrazine unit acted as a quencher of fluorescence, the role of the tetrazine is redefined here. Such repurposed role of tetrazines is foreseen to address the limitations of tetrazine-quenched red/NIR excitable fluorogenic probes.

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