Selective recognition of acetylcholine over choline by a fluorescent cage

Augustin Long; Nicolas Fantozzi; Sandra Pinet; Emilie Genin; Rémi Pétuya; Didier Bégué; Vincent Robert; Jean-Pierre Dutasta; Isabelle Gosse; Alexandre Martinez

doi:10.1039/C9OB00931K

Selective recognition of acetylcholine over choline by a fluorescent cage†

Augustin Long,^a Nicolas Fantozzi,^b Sandra Pinet,^b Emilie Genin,

^b Rémi Pétuya,

^c Didier Bégué,

^c Vincent Robert,

^d Jean-Pierre Dutasta,

^e Isabelle Gosse^b and Alexandre Martinez

*^a

Author affiliations

* Corresponding authors

^a Aix Marseille Université, Centrale Marseille, CNRS, ISM2 UMR 7313, Marseille, France
E-mail: alexandre.martinez@centrale-marseille.fr

^b ISM, UMR 5255 CNRS, Bordeaux INP and Université de Bordeaux, 351 Cours de la Libération, F-33400 Talence, France

^c CNRS/Université de Pau et des Pays de l'Adour/E2S UPPA, Institut des Sciences Analytiques et de Physicochimie pour l'Environnement et les Matériaux, UMR5254, Pau, France

^d Laboratoire de Chimie Quantique Institut de Chimie, UMR CNRS 7177, Université de Strasbourg, 4, rue Blaise Pascal, F-67070 Strasbourg, France

^e Laboratoire de Chimie École Normale Supérieure de Lyon, CNRS, UCBL, 46 Allée d'Italie, F-69364 Lyon, France

Abstract

A fluorescent hemicryptophane has been synthesized and can be used as a turn on receptor of acetylcholine. A binding constant of 2.4 × 10⁴ M⁻¹ was measured for this neurotransmitter, and its selective and sensitive detection over choline and choline phosphate was achieved. NMR and DFT calculations provide insight into the interactions involved in this selective recognition process.

Organic & Biomolecular Chemistry

Selective recognition of acetylcholine over choline by a fluorescent cage†

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Selective recognition of acetylcholine over choline by a fluorescent cage

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