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 (1)H 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.
authors.affiliation: Laboratory of Supramolecular Chemistry and Technology, MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede, The Netherlands.
authors.forename: Francesca
authors.initials: F
authors.lastname: Corbellini
authors.forename: Ronald M A
authors.initials: RM
authors.lastname: Knegtel
authors.forename: Peter D J
authors.initials: PD
authors.lastname: Grootenhuis
authors.forename: Mercedes
authors.initials: M
authors.lastname: Crego-Calama
authors.forename: David N
authors.initials: DN
authors.lastname: Reinhoudt
mesh_terms: D002214:Capsules / Q000737:chemistry*; D017666:Deuterium Oxide; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization; D014867:Water
chemical_list: D002214:Capsules; D014867:Water; D017666:Deuterium Oxide