Water-soluble molecular capsules: self-assembly and binding properties.
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.
Corbellini
Francesca
F
Laboratory of Supramolecular Chemistry and Technology, MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede, The Netherlands.
Knegtel
Ronald M A
RM
Grootenhuis
Peter D J
PD
Crego-Calama
Mercedes
M
Reinhoudt
David N
DN
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
D002214:Capsules; D014867:Water; D017666:Deuterium Oxide