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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Proparacaine complexation with beta-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied H-1-NMR approaches

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Author(s):
Arantes, Lucas Micqueias [1] ; Scarelli, Camilla [2] ; Marsaioli, Anita Jocelyne [3] ; de Paula, Eneida [2] ; Fernandes, Sergio Antonio [1]
Total Authors: 5
Affiliation:
[1] Univ Fed Vicosa, Dept Quim, GQSB, BR-36570000 Vicosa, MG - Brazil
[2] Univ Estadual Campinas, Inst Biol, Dept Bioquim, BR-13081970 Campinas, SP - Brazil
[3] Univ Estadual Campinas, Inst Quim, Dept Quim Organ, BR-13081970 Campinas, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Magnetic Resonance in Chemistry; v. 47, n. 9, p. 757-763, SEP 2009.
Web of Science Citations: 22
Abstract

This study focused on the use of NMR techniques as a tool for the investigation of complex formation between proparacaine and cyclodextrins (CDs) or p-sulfonic acid calix{[}6]arene. The pH dependence of the complexation of proparacaine with beta-CD and p-sulfonic acid calix{[}6]arene was studied and binding constants were determined by (1)H NMR spectroscopy {[}diffusion-ordered spectroscopy (DOSY)] for the charged and uncharged forms of the local anesthetic in beta-CD and p-sulfonic acid calix{[}6]arene. The stoichiometries of the complexes was determined and rotating frame Overhauser enhancement spectroscopy (ROESY) 1D experiments revealed details of the molecular insertion of proparacaine into the beta-CD and p-sulfonic acid calix{[}6]arene cavities. The results unambiguously demonstrate that pH is an important factor for the development of supramolecular architectures based on beta-CD and p-sulfonic acid calix{[}6]arene as the host molecules. Such host-guest complexes were investigated in view of their potential use as new therapeutic formulations, designed to increase the bioavailability and/or to decrease the systemic toxicity of proparacaine in anesthesia procedures. Copyright (C) 2009 John Wiley \& Sons, Ltd. (AU)

FAPESP's process: 05/00602-4 - Supramolecular interactions between local anesthetics and their transport (cyclodextrins, calixarenes and liposomes) by NMR study
Grantee:Sergio Antonio Fernandes
Support Opportunities: Scholarships in Brazil - Post-Doctoral