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Synthèse et études de sondes fluorescentes pour la détection de neurotransmetteurs

Abstract : Neurodegenerative diseases like Alzheimer, Parkinson or Huntington are related to an imbalance of neurotransmitters. Nevertheless, the sources of this neuronal communication disorder are not well-understood to date, partly because of the lack of tools allowing real-time and real-space monitoring of neurotransmitters, in biological systems. Thus, it is extremely important to develop tools such as fluorescent supramolecular probes for the imaging of neurotransmitters.In a previous study carried out in our groups, fluorescent probes based on a cyclotriveratrylene skeleton, able to recognize either choline or acetylcholine (ACh) in buffer aqueous solution (pH 7.4), have been synthesized. However, these molecules do not respect all the criteria needed for the imaging of species in biological conditions. Indeed, their complexation constants are insufficient. To improve the binding affinity between probes and neurotransmitters we turned our attention to capsules built from cyclotriveratrylene core, namely hemicryptophanes (HC). HC are known to bind ammoniums guests thanks to their preorganized cavity. New fluorescent hemicryptophanes were synthesized. The synthetic pathway we developed allow us to easily modify the HC’s fluorescent moiety. Some of them show good affinities for different neurotransmitters like acetylcholine, dopamine, serotonin, good sensitivities and are soluble in buffer aqueous solution. Their synthesis as well as their fluorescence and recognition properties will be presented.
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Nicolas Fantozzi. Synthèse et études de sondes fluorescentes pour la détection de neurotransmetteurs. Chimie organique. Université de Bordeaux, 2019. Français. ⟨NNT : 2019BORD0423⟩. ⟨tel-02939507⟩

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