Spectroscopic characterization of ibuprofen/2-hydroxypropyl-β-cyclodextrin inclusion complex
1998; Elsevier BV; Volume: 175; Issue: 2 Linguagem: Inglês
10.1016/s0378-5173(98)00286-5
ISSN1873-3476
AutoresIn-Joon Oh, Mi Young Lee, Yong‐Bok Lee, Sang‐Chul Shin, Ilyeong Park,
Tópico(s)Analytical Methods in Pharmaceuticals
ResumoIbuprofen has been used widely as an anti-inflammatory and anti-pyretic agent. It is slightly soluble in water. Several investigators have conducted studies to improve the dissolution rate of ibuprofen using cyclodextrin complexation. In this study, the geometry and the structural features of the ibuprofen/hydroxypropyl-β-cyclodextrin (HPβCD) inclusion complex were studied by NMR and fluorescence spectroscopy. The fluorescence intensity of ibuprofen increased as the concentration of HPβCD increased. Continuous variation plots by NMR study suggested that 1:1 stoichiometric complex was formed in solution. The spectral analysis of 1H- and 13C-NMR measurements showed that the signals of the aromatic protons of ibuprofen were shifted upfield, probably resulting from the interaction of HPβCD with aromatic ring of ibuprofen. We also postulated the optimized structure of ibuprofen/HPβCD inclusion complex through a molecular modeling program (SYBYL 6.4) and we found that the features of this postulated structure were in a good agreement with the 1H- and 13C-NMR spectra.
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