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

• Published in: Journal of physical organic chemistry Vol. 28; no. 8; pp. 527 - 535
• Main Authors: Andreyko, Elena A., Padnya, Pavel L., Stoikov, Ivan I.
• Format: Journal Article
• Language: English
• Published: Bognor Regis Blackwell Publishing Ltd 01-08-2015; Wiley Subscription Services, Inc
• Subjects: associates; molecular recognition; proteins; supramolecular chemistry; synthetic receptors; thiacalixarenes
• ISSN: 0894-3230; 1099-1395
• DOI: 10.1002/poc.3433

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.
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 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.