Theoretical investigation on the molecular inclusion process of urease inhibitors into p-sulfonic acid calix[4,6]arenes

• Published in: Chemical physics letters Vol. 692; pp. 117 - 123
• Main Authors: Reis, Sayron, Liberto, Natália Aparecido, Fernandes, Sergio Antônio, de Fátima, A., De Almeida, Wagner B., Guimarães, Luciana, Nascimento, Clebio S.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 16-01-2018
• Subjects: Biginelli adducts; Calixarenes; DFT calculations; Inclusion complexes; Urease inhibitors; Urease inhibitors; Inclusion complexes; Calixarenes; DFT calculations; Biginelli adducts
• ISSN: 0009-2614; 1873-4448
• DOI: 10.1016/j.cplett.2017.12.023

[Display omitted]
•DFT theoretical analysis of the inclusion process involving two urease inhibitors into the p-sulfonic acid calix[4,6]arenes.•The formation of hydrogen bonds between two hosts molecules play a major role on the inclusion complex stabilization.•The formation of 2:1 complexes is considerably more stable than 1:1 M ratio.
The present paper reports results from a theoretical analysis of the host/guest inclusion process involving two Biginelli adducts urease inhibitors into the p-sulfonic acid calix[4,6]arenes. Structure and stabilization energies, were calculated, in aqueous phase, and in 1:1 and 2:1 M ratios, by DFT/B97D calculations. As main result we found the BGA-1@p-SAC[6] complex as the most stable specie in 2:1 stoichiometry. For this complex, the BGA-1 molecule remains trapped inside the p-SAC[6] tubular dimer with the guest totally encapsulated. Besides, the formation of hydrogen bonds between two p-SAC[6] hosts play a major role on the inclusion complex stabilization.