Selective recognition of quaternary ammonium ions and zwitterions by using a biomimetic bis-calix[6]arene-based receptor

Steven Moerkerke, Volodymyr Malytskyi, Lionel Marcélis, Johan Wouters, Ivan Jabin

Research output: Contribution to journalArticle

Abstract

Artificial receptors able to recognize efficiently chemical species bearing a quaternary ammonium group have potential applications in the fields of biological and environmental analyses. A possible biomimetic strategy for the elaboration of such receptors consists of associating in close proximity a polyaromatic cavity with a polar binding site. Herein, we show that bis-calix[6]arene 1 behaves as a heteroditopic receptor that can bind biologically relevant quaternary ammonium ions and zwitterions. This host can selectively extract carbamylcholine G3 from water, opening the way for the sensing of this acetylcholine agonist. In some cases, a kinetic selectivity is observed for the shorter guests whereas kinetically stable host-guest complexes can be detected under conditions where they are thermodynamically disfavoured. These results can be rationalized by the unique mode of entrance and escape of the guests into bis-calix[6]arene 1. All these binding properties strongly differ from those reported for related calixarene-based receptors.

Original languageEnglish
Pages (from-to)8967-8974
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number42
DOIs
Publication statusPublished - 2017

Fingerprint

Biomimetics
zwitterions
biomimetics
Ammonium Compounds
Bearings (structural)
Calixarenes
Artificial Receptors
Ions
Cholinergic Agonists
Carbachol
ions
Binding Sites
acetylcholine
Kinetics
Water
entrances
escape
proximity
selectivity
cavities

Keywords

  • Journal Article

Cite this

Moerkerke, Steven ; Malytskyi, Volodymyr ; Marcélis, Lionel ; Wouters, Johan ; Jabin, Ivan. / Selective recognition of quaternary ammonium ions and zwitterions by using a biomimetic bis-calix[6]arene-based receptor. In: Organic and Biomolecular Chemistry. 2017 ; Vol. 15, No. 42. pp. 8967-8974.
@article{0b6faf642cef4d8cb6d44720990d792f,
title = "Selective recognition of quaternary ammonium ions and zwitterions by using a biomimetic bis-calix[6]arene-based receptor",
abstract = "Artificial receptors able to recognize efficiently chemical species bearing a quaternary ammonium group have potential applications in the fields of biological and environmental analyses. A possible biomimetic strategy for the elaboration of such receptors consists of associating in close proximity a polyaromatic cavity with a polar binding site. Herein, we show that bis-calix[6]arene 1 behaves as a heteroditopic receptor that can bind biologically relevant quaternary ammonium ions and zwitterions. This host can selectively extract carbamylcholine G3 from water, opening the way for the sensing of this acetylcholine agonist. In some cases, a kinetic selectivity is observed for the shorter guests whereas kinetically stable host-guest complexes can be detected under conditions where they are thermodynamically disfavoured. These results can be rationalized by the unique mode of entrance and escape of the guests into bis-calix[6]arene 1. All these binding properties strongly differ from those reported for related calixarene-based receptors.",
keywords = "Journal Article",
author = "Steven Moerkerke and Volodymyr Malytskyi and Lionel Marc{\'e}lis and Johan Wouters and Ivan Jabin",
year = "2017",
doi = "10.1039/c7ob02031g",
language = "English",
volume = "15",
pages = "8967--8974",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "42",

}

Selective recognition of quaternary ammonium ions and zwitterions by using a biomimetic bis-calix[6]arene-based receptor. / Moerkerke, Steven; Malytskyi, Volodymyr; Marcélis, Lionel; Wouters, Johan; Jabin, Ivan.

In: Organic and Biomolecular Chemistry, Vol. 15, No. 42, 2017, p. 8967-8974.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Selective recognition of quaternary ammonium ions and zwitterions by using a biomimetic bis-calix[6]arene-based receptor

AU - Moerkerke, Steven

AU - Malytskyi, Volodymyr

AU - Marcélis, Lionel

AU - Wouters, Johan

AU - Jabin, Ivan

PY - 2017

Y1 - 2017

N2 - Artificial receptors able to recognize efficiently chemical species bearing a quaternary ammonium group have potential applications in the fields of biological and environmental analyses. A possible biomimetic strategy for the elaboration of such receptors consists of associating in close proximity a polyaromatic cavity with a polar binding site. Herein, we show that bis-calix[6]arene 1 behaves as a heteroditopic receptor that can bind biologically relevant quaternary ammonium ions and zwitterions. This host can selectively extract carbamylcholine G3 from water, opening the way for the sensing of this acetylcholine agonist. In some cases, a kinetic selectivity is observed for the shorter guests whereas kinetically stable host-guest complexes can be detected under conditions where they are thermodynamically disfavoured. These results can be rationalized by the unique mode of entrance and escape of the guests into bis-calix[6]arene 1. All these binding properties strongly differ from those reported for related calixarene-based receptors.

AB - Artificial receptors able to recognize efficiently chemical species bearing a quaternary ammonium group have potential applications in the fields of biological and environmental analyses. A possible biomimetic strategy for the elaboration of such receptors consists of associating in close proximity a polyaromatic cavity with a polar binding site. Herein, we show that bis-calix[6]arene 1 behaves as a heteroditopic receptor that can bind biologically relevant quaternary ammonium ions and zwitterions. This host can selectively extract carbamylcholine G3 from water, opening the way for the sensing of this acetylcholine agonist. In some cases, a kinetic selectivity is observed for the shorter guests whereas kinetically stable host-guest complexes can be detected under conditions where they are thermodynamically disfavoured. These results can be rationalized by the unique mode of entrance and escape of the guests into bis-calix[6]arene 1. All these binding properties strongly differ from those reported for related calixarene-based receptors.

KW - Journal Article

UR - http://www.scopus.com/inward/record.url?scp=85032721630&partnerID=8YFLogxK

U2 - 10.1039/c7ob02031g

DO - 10.1039/c7ob02031g

M3 - Article

C2 - 29043359

VL - 15

SP - 8967

EP - 8974

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 42

ER -