Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/86621
Type: Artigo de periódico
Title: Benzocaine Complexation With P-sulfonic Acid Calix[n]arene: Experimental (1h-nmr) And Theoretical Approaches
Author: Arantes L.M.
Varejao E.V.V.
Pelizzaro-Rocha K.J.
Cereda C.M.S.
De Paula E.
Lourenco M.P.
Duarte H.A.
Fernandes S.A.
Abstract: The aim of this work was to study the interaction between the local anesthetic benzocaine and p-sulfonic acid calix[n]arenes using NMR and theoretical calculations and to assess the effects of complexation on cytotoxicity of benzocaine. The architectures of the complexes were proposed according to 1H NMR data (Job plot, binding constants, and ROESY) indicating details on the insertion of benzocaine in the cavity of the calix[n]arenes. The proposed inclusion compounds were optimized using the PM3 semiempirical method, and the electronic plus nuclear repulsion energy contributions were performed at the DFT level using the PBE exchange/correlation functional and the 6-311G(d) basis set. The remarkable agreement between experimental and theoretical approaches adds support to their use in the structural characterization of the inclusion complexes. In vitro cytotoxic tests showed that complexation intensifies the intrinsic toxicity of benzocaine, possibly by increasing the water solubility of the anesthetic and favoring its partitioning inside of biomembranes. The architetures of inclusion complexes between benzocaine and p-sulfonic acid calix[n]arenes were characterized by means of experimental 1H NMR spectroscopy and theoretical calculations. In vitro cytotoxic tests showed that complexation intensifies the intrinsic toxicity of benzocaine, possibly by favoring its partitioning inside of biomembranes. © 2013 John Wiley & Sons A/S.
Editor: Blackwell Publishing Ltd
Rights: fechado
Identifier DOI: 10.1111/cbdd.12267
Address: http://www.scopus.com/inward/record.url?eid=2-s2.0-84899479432&partnerID=40&md5=ac139bbadbb016b3086f038afe65dbbf
Date Issue: 2014
Appears in Collections:Unicamp - Artigos e Outros Documentos

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