Novel lactide derivatives of p-tert-butylthiacalix[4]arene: Directed synthesis and molecular recognition of catecholamines

Three stereoisomeric forms of p-tert-butylthiacalix[4]arene (cone, partial cone, and 1,3-alternate conformations) have been proposed as macrocyclic scaffold to obtain dendrimer-like compounds. Modification of the macrocycle with fragments containing both amide and lactide groups made it possible to obtain original analogs of dendrimers with symmetric and asymmetric structures. These compounds are capable of binding catechol-amines (dopamine, epinephrine, and norepinephrine). The influence of the macrocyclic platform conformation of the compounds obtained on the efficiency and selectivity of their complexation with catecholamines was established by UV-visible, fluorescence and NMR spectroscopy. It was found that the 1,3-alternate conformation of the macrocycle core was the most favorable for binding all the guests. In case of the cone conformation, selectivity of binding of epinephrine and norepinephrine was observed. Location of catecholamines in the resulting complexes against the macrocyclic platform affected the efficiency of interaction of the synthesized thiacalixarenes with guests. (C) 2020 Elsevier B.V. All rights reserved.

Automated summary

The study focuses on utilizing p-tert-butylthiacalix[4]arene as a macrocyclic scaffold to design and synthesize dendrimer-like compounds. By modifying the macrocycle with fragments containing amide and lactide groups, original analogs of dendrimers with symmetric and asymmetric structures can be obtained. The 1,3-alternate conformation is found to be most favorable for binding catechol-amines, while the cone conformation shows selectivity in binding epinephrine and norepinephrine.