A Hydrosoluble Triphenylene That Preferentially Binds Acetylcholine, Epibatidine, and Nicotine

Synthesis and binding properties of a new hydrosoluble triphenylene 1b are reported. Selective recognition of acetylcholine (ACh) against other aliphatic ammoniums is achieved by this flat receptor, which also forms complexes with epibatidine and nicotine. Ionic pairing and hydrophobic effects betwe...

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Veröffentlicht in:	Journal of organic chemistry 2009-07, Vol.74 (14), p.5059-5062
Hauptverfasser:	Givelet, Cécile, Buffeteau, Thierry, Arnaud-Neu, Françoise, Hubscher-Bruder, Véronique, Bibal, Brigitte
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetylcholine - chemistry Aliphatic compounds Ammonia - chemistry Binding Sites Bridged Bicyclo Compounds, Heterocyclic - chemistry Chemistry Cholinergic Agents - chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Magnetic Resonance Spectroscopy Molecular Structure Nicotine - chemistry Organic chemistry Preparations and properties Pyridines - chemistry Solubility Thermodynamics Water - chemistry
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Beschreibung
Zusammenfassung:	Synthesis and binding properties of a new hydrosoluble triphenylene 1b are reported. Selective recognition of acetylcholine (ACh) against other aliphatic ammoniums is achieved by this flat receptor, which also forms complexes with epibatidine and nicotine. Ionic pairing and hydrophobic effects between host 1b and ACh are studied by infrared spectroscopy.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo900683x