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

Autor(es)

Arantes, Lucas Micqueias ^[1] ; Scarelli, Camilla ^[2] ; Marsaioli, Anita Jocelyne ^[3] ; de Paula, Eneida ^[2] ; Fernandes, Sergio Antonio ^[1]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: Magnetic Resonance in Chemistry; v. 47, n. 9, p. 757-763, SEP 2009.
• Citações Web of Science: 22

Resumo

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)

• Processo FAPESP: 05/00602-4 - Interações supramoleculares entre anestésicos locais e seus carreadores (ciclodextrinas, calixarenos e lipossomas), estudada por RMN
• Beneficiário: Sergio Antonio Fernandes
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado