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

Abstract

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.