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 antiinflammatory 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.

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

Guella, Graziano;Mancini, Ines;Verrocchio, Paolo;Viliani, Gabriele
2011

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 antiinflammatory 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.
V., Crupi; Guella, Graziano; D., Majolino; Mancini, Ines; B., Rossi; R., Stancanelli; V., Venuti; Verrocchio, Paolo; Viliani, Gabriele
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11572/92568
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