Premium
Amphiphilic p‐tert ‐butylthiacalix[4]arenes containing quaternary ammonium groups: from small molecules toward water‐soluble nanoscale associates
Author(s) -
Andreyko Elena A.,
Padnya Pavel L.,
Stoikov Ivan I.
Publication year - 2015
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3433
Subject(s) - chemistry , supramolecular chemistry , amphiphile , calixarene , aromatic amino acids , molecule , tryptophan , amino acid , polymer chemistry , stereochemistry , organic chemistry , biochemistry , copolymer , polymer
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 1 H‐ 1 H 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.