Proparacaine complexation with β-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied 1 H-NMR approaches
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 β-CD and p-sulfonic acid calix[6]arene was studied and bindin...
| Autores: | , , , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 2009 |
| País: | Brasil |
| Recursos: | Universidade Federal de Viçosa (UFV) |
| Repositório: | LOCUS Repositório Institucional da UFV |
| Idioma: | inglês |
| OAI Identifier: | oai:locus.ufv.br:123456789/14554 |
| Acesso em linha: | http://dx.doi.org/10.1002/mrc.2460 http://www.locus.ufv.br/handle/123456789/14554 |
| Access Level: | Acceso aberto |
| Palavra-chave: | Proparacaine Cyclodextrin Calixarenes NMR |
| 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 β-CD and p-sulfonic acid calix[6]arene was studied and binding constants were determined by 1H NMR spectroscopy [diffusion-ordered spectroscopy (DOSY)] for the charged and uncharged forms of the local anesthetic in β-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 β-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 β-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. |
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