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Article Dans Une Revue Helvetica Chimica Acta Année : 2005

Para-Sulfonated Calixarenes Used as Synthetic Receptors for Complexing Photolabile Cholinergic Ligand

Résumé

The water‐soluble tetra‐, hexa‐ and octasulfonated calix[4]arenes, calix[6]arenes, and calix[8]arenes 1–3, respectively, were investigated as potential synthetic receptors for photolabile cholinergic ligand A, a photolytic precursor of choline. Ligand A is a bifunctional molecule carrying a photolabile 2‐nitrobenzyl group at one end and a choline moiety at the other end. Results from NMR studies have shown that calixarenes 1–3 form stable 1 : 1 complexes with A, having similar binding potential to that observed with the cholinergic enzymes acetylcholinesterase and butyrylcholinesterase. Further studies have suggested that calix[8]arene forms a ditopic complex by binding concomitantly to both the cationic choline moiety and the aromatic photolabile group of A, whereas calix[4]arene and calix[6]arene form monotopic complexes with A. The ditopic complex between calix[8]arene and A results from mutually induced fitting process, while the monotopic complexes between calix[4]arene and A can be regulated by pH: at neutral pH, calix[4]arene specifically binds the cationic choline moiety, while, at acidic pH, it complexes unselectively both the cationic choline moiety and the aromatic group of A. Our results show that para‐sulfonated calixarenes are versatile artificial receptors which bind in various ways to the bifunctional photolabile cholinergic ligand A, depending on their size, geometry, and state of protonation.

Domaines

Chimie

Dates et versions

hal-00129989 , version 1 (08-02-2007)

Identifiants

Citer

Alexandre Specht, Fabio Ziarelli, Philippe Bernard, Maurice Goeldner, Ling Peng. Para-Sulfonated Calixarenes Used as Synthetic Receptors for Complexing Photolabile Cholinergic Ligand. Helvetica Chimica Acta, 2005, 88 (10), pp.2641-2653. ⟨10.1002/hlca.200590205⟩. ⟨hal-00129989⟩
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