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Article Dans Une Revue New Journal of Chemistry Année : 2020

A new fluorescent hemicryptophane for acetylcholine recognition with an unusual recognition mode

Jean-Pierre Dutasta
Laure Guy
Emilie Genin
  • Fonction : Auteur

Résumé

A new off-on fluorescent hemicryptophane probe for acetylcholine has been designed. This hemicryptophane, made fluorescent via an extension of the conjugation of its cyclotriveratrylene C3-symmetry part, exhibits improved fluorescence properties compared with fluorescent hemicryptophanes previously described. Indeed, both the excitation and emission wavelengths are red-shifted and the quantum yield is increased. Moreover, this hemicryptophane is able to bind acetylcholine with a high association constant of 3.2 × 104 M-1. This recognition process is accompanied by an increase in the brightness of the capsule. Surprisingly, contrary to what is commonly observed with cyclotriveratrylene-based hosts, the quaternary ammonium of the guest interacts with the tris(2-aminoethyl)amine south part of the hemicryptophane instead of the cyclotriveratrylene north part. This unusual binding mode is supported by both proton NMR experiments and density functional theory calculations.
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Dates et versions

hal-02920449 , version 1 (23-03-2021)

Identifiants

Citer

Nicolas Fantozzi, Rémi Pétuya, Alberto Insuasty, Augustin Long, Sara Lefevre, et al.. A new fluorescent hemicryptophane for acetylcholine recognition with an unusual recognition mode. New Journal of Chemistry, 2020, 44 (27), pp.11853-11860. ⟨10.1039/d0nj02794d⟩. ⟨hal-02920449⟩
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