Amphiphilic p-tert -butylthiacalix[4]arenes containing quaternary ammonium groups: from small molecules toward water-soluble nanoscale associates

The formation of supramolecular associates based on water-soluble p-tert-butylthiacalix[4]arenes with amino acids has been studied. It was shown that amphiphilic p-tert-butylthiacalix[4]arenes preferably formed supramolecular associates with aromatic α-amino acids (tyrosine and tryptophan). Increasing size of the substituents of p-tert-butylthiacalix[4]arenes led to increase molecular weight of supramolecular associates based on the macrocycles and “guest” molecules. The spatial structures of p-tert-butylthiacalix[4]arenes and their associates with phenylalanine were studied by two-dimensional 1H-1H nuclear Overhauser effect NMR spectroscopy. The ability of aggregates based on p-tert-butylthiacalix[4]arenes and amino acids to effectively interact with bovine serum albumin with the formation of 7- to 8-nm nanoparticles was shown. Copyright © 2015 John Wiley & Sons, Ltd.