Food Biophysics

, Volume 6, Issue 2, pp 267–273

A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

  • Vincenza Crupi
  • Graziano Guella
  • Domenico Majolino
  • Ines Mancini
  • Barbara Rossi
  • Rosanna Stancanelli
  • Valentina Venuti
  • Paolo Verrocchio
  • Gabriele Viliani
SPECIAL ISSUE ARTICLE

DOI: 10.1007/s11483-011-9211-6

Cite this article as:
Crupi, V., Guella, G., Majolino, D. et al. Food Biophysics (2011) 6: 267. doi:10.1007/s11483-011-9211-6

Abstract

The effects of chiral discrimination in inclusion complexes formed by native β-cyclodextrin and its substituted form (namely methyl-β-cyclodextrin) with racemate or pure enantiomers of the non-steroidal anti-inflammatory drug ibuprofen have been investigated in water. Stability constants and complexation efficiency have been determined for these host–guest systems with a 1:1 molar ratio from phase solubility profiles, showing that in aqueous solution, methylated cyclodextrin is a better complex agent than native cyclodextrin, with more enhanced effects for the (R)-enantiomer. These results have been validated using NMR technique. In particular, 1H NMR spectra in D2O show a splitting of the signals for the methyl group and the aromatic protons close to the asymmetric centre of the racemate ibuprofen included in cyclodextrin cavity.

Keywords

IbuprofenPhase solubilityCyclodextrinsInclusion complexChiral discrimination

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Vincenza Crupi
    • 1
  • Graziano Guella
    • 2
  • Domenico Majolino
    • 1
  • Ines Mancini
    • 2
  • Barbara Rossi
    • 2
    • 3
  • Rosanna Stancanelli
    • 4
  • Valentina Venuti
    • 1
  • Paolo Verrocchio
    • 2
  • Gabriele Viliani
    • 2
  1. 1.Dipartimento di FisicaUniversità di MessinaMessinaItaly
  2. 2.Dipartimento di FisicaUniversità di TrentoPovoItaly
  3. 3.Fondazione Bruno KesslerPovoItaly
  4. 4.Dipartimento Farmaco-ChimicoUniversità di MessinaMessinaItaly