Hemicryptophanes with Improved Fluorescent Properties for the Selective Recognition of Acetylcholine over Choline

Augustin Long (1) , Elise Antonetti (1) , Alberto Insuasty (1) , Sandra Pinet (2) , Isabelle Gosse (2) , Vincent Robert (3) , Jean-Pierre Dutasta (4) , Alexandre Martinez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 ISM - Institut des Sciences Moléculaires
3 Laboratoire de Chimie Quantique
4 LC - Laboratoire de Chimie - UMR5182

The synthesis of two new fluorescent hemicryptophanes is reported. They were found to be efficient and selective receptors for acetylcholine over choline. When compared to other hemicryptophane hosts previously reported for the selective recognition of acetylcholine, they display improved fluorescent properties: their maximum emission wavelengths are red-shifted and the quantum yields are higher. NMR titration experiments and density functional theory (DFT) calculations support the results obtained from fluorescence spectroscopy and give insights into the interactions involved in the host/guest complexes and into the selectivity for acetylcholine over choline.

Domaines: Chimie

Augustin Long, Elise Antonetti, Alberto Insuasty, Sandra Pinet, Isabelle Gosse, et al.. Hemicryptophanes with Improved Fluorescent Properties for the Selective Recognition of Acetylcholine over Choline. Journal of Organic Chemistry, 2020, 85 (10), pp.6400-6407. ⟨10.1021/acs.joc.0c00217⟩. ⟨hal-03180306⟩