Chemistry - A European Journal

OMECA

Abstract

Selective and strategic modification of redox cofactors offers significant advantages for the design of molecular probes, including high compatibility and affinity. This is particularly relevant in the case of redox cofactors with innate fluorescence properties, such as flavins, and synthetic strategies toward their functionalized analogues are of high interest to modulate properties. However, the synthetic elaboration of flavins and their alloxazine isomers still suffers from limitations. We report easy access to bioinspired fluorescent alloxazines with a boron difluorocatecholate moiety and explore the impact of core aromatic substitution on their photophysical properties. Further chemical elaboration through a CuAAC (copper-catalyzed azide–alkyne cycloaddition) click chemistry strategy opens the way to easy derivatization and further addressing.

 

 

Graphical Abstract

The design of fluorescent molecules inspired by natural cofactors to monitor biological processes carries some intrinsic advantages. This is particularly relevant in the case of redox cofactors with innate fluorescence properties, such as flavins, and synthetic strategies toward their functionalized analogues are of high interest to modulate properties. This work reports easy access to bioinspired fluorescent alloxazines (flavin analogues) with a boron difluorocatecholate moiety and further chemical elaboration through a CuAAC (copper-catalyzed azide–alkyne cycloaddition) click chemistry strategy, which opens the way to easy derivatization and further addressing. This molecular approach provides a design concept that could lead to bimodal probes detectable by fluorescence and 19F NMR spectroscopy.

 

 

Reference

Engineering Alloxazines by Boron Coordination and Click Chemistry toward Small‐molecule Fluorescent Probes

Oscar Charpentier, Ambroise Mouhanna, Eleanna Nikolopoulos, Aurélie Guenet, Christophe Gourlaouen and Marine Desage-El Murr

Chemistry - A European Journal, first published: 25 July 2025 – DOI : http://dx.doi.org/10.1002/chem.202501878 
 

Contacts

Marine Desage-El Murr & Aurélie Guenet, team OMECA, Institut de Chimie de Strasbourg, UMR 7177.

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