Water-soluble molecular capsules: self-assembly and binding properties

Francesca Corbellini; Ronald M.A. Knegtel; Peter D.J. Grootenhuis; Mercedes Crego-Calama; David N. Reinhoudt

doi:10.1002/chem.200400849

Water-soluble molecular capsules: self-assembly and binding properties

Francesca Corbellini, Ronald M.A. Knegtel, Peter D.J. Grootenhuis, Mercedes Crego-Calama^*, David N. Reinhoudt^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

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Abstract

The self-assembly and characterization of water-soluble calix[4]arene-based molecular capsules (12) is reported. The assemblies are the result of ionic interactions between negatively charged calix[4]arenes 1 a and 1 b, functionalized at the upper rim with amino acid moieties, and a positively charged tetraamidiniumcalix[4]arene 2. The formation of the molecular capsules is studied by 1H NMR spectroscopy, ESI mass spectrometry (ESI-MS), and isothermal titration calorimetry (ITC). A molecular docking protocol was used to identify potential guest molecules for the self-assembled capsule 1 a2. Experimental guest encapsulation studies indicate that capsule 1 a2 is an effective host for both charged (N-methylquinuclidinium cation) and neutral molecules (6-amino-2-methylquinoline) in water.

Original language	English
Pages (from-to)	298-307
Number of pages	9
Journal	Chemistry : a European journal
Volume	11
Issue number	1
DOIs	https://doi.org/10.1002/chem.200400849
Publication status	Published - 2005

Keywords

Docking
Host–guest systems
Ionic interactions
Molecular capsules
Self-assembly

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title = "Water-soluble molecular capsules: self-assembly and binding properties",

abstract = "The self-assembly and characterization of water-soluble calix[4]arene-based molecular capsules (12) is reported. The assemblies are the result of ionic interactions between negatively charged calix[4]arenes 1 a and 1 b, functionalized at the upper rim with amino acid moieties, and a positively charged tetraamidiniumcalix[4]arene 2. The formation of the molecular capsules is studied by 1H NMR spectroscopy, ESI mass spectrometry (ESI-MS), and isothermal titration calorimetry (ITC). A molecular docking protocol was used to identify potential guest molecules for the self-assembled capsule 1 a2. Experimental guest encapsulation studies indicate that capsule 1 a2 is an effective host for both charged (N-methylquinuclidinium cation) and neutral molecules (6-amino-2-methylquinoline) in water.",

keywords = "Docking, Host–guest systems, Ionic interactions, Molecular capsules, Self-assembly",

author = "Francesca Corbellini and Knegtel, {Ronald M.A.} and Grootenhuis, {Peter D.J.} and Mercedes Crego-Calama and Reinhoudt, {David N.}",

year = "2005",

doi = "10.1002/chem.200400849",

language = "English",

volume = "11",

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journal = "Chemistry : a European journal",

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TY - JOUR

T1 - Water-soluble molecular capsules

T2 - self-assembly and binding properties

AU - Corbellini, Francesca

AU - Knegtel, Ronald M.A.

AU - Grootenhuis, Peter D.J.

AU - Crego-Calama, Mercedes

AU - Reinhoudt, David N.

PY - 2005

Y1 - 2005

N2 - The self-assembly and characterization of water-soluble calix[4]arene-based molecular capsules (12) is reported. The assemblies are the result of ionic interactions between negatively charged calix[4]arenes 1 a and 1 b, functionalized at the upper rim with amino acid moieties, and a positively charged tetraamidiniumcalix[4]arene 2. The formation of the molecular capsules is studied by 1H NMR spectroscopy, ESI mass spectrometry (ESI-MS), and isothermal titration calorimetry (ITC). A molecular docking protocol was used to identify potential guest molecules for the self-assembled capsule 1 a2. Experimental guest encapsulation studies indicate that capsule 1 a2 is an effective host for both charged (N-methylquinuclidinium cation) and neutral molecules (6-amino-2-methylquinoline) in water.

AB - The self-assembly and characterization of water-soluble calix[4]arene-based molecular capsules (12) is reported. The assemblies are the result of ionic interactions between negatively charged calix[4]arenes 1 a and 1 b, functionalized at the upper rim with amino acid moieties, and a positively charged tetraamidiniumcalix[4]arene 2. The formation of the molecular capsules is studied by 1H NMR spectroscopy, ESI mass spectrometry (ESI-MS), and isothermal titration calorimetry (ITC). A molecular docking protocol was used to identify potential guest molecules for the self-assembled capsule 1 a2. Experimental guest encapsulation studies indicate that capsule 1 a2 is an effective host for both charged (N-methylquinuclidinium cation) and neutral molecules (6-amino-2-methylquinoline) in water.

KW - Docking

KW - Host–guest systems

KW - Ionic interactions

KW - Molecular capsules

KW - Self-assembly

U2 - 10.1002/chem.200400849

DO - 10.1002/chem.200400849

M3 - Article

SN - 0947-6539

VL - 11

SP - 298

EP - 307

JO - Chemistry : a European journal

JF - Chemistry : a European journal

IS - 1

ER -

Water-soluble molecular capsules: self-assembly and binding properties

Abstract

Keywords

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