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New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution

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Abstract

We report results regarding the use of 1H-NMR spectroscopy in the study of the conformational behaviour and optical activity of omeprazole. Changes in the chemical shifts of chosen atoms reveal that the conformational behaviour of omeprazole is temperature and pH sensitive. Separation and identification of omeprazole enantiomers in the presence of natural and derivative cyclodextrins, such as β-cyclodextrin (βCD) and methyl-β-cyclodextrin (MβCD) are achieved using 1H-NMR spectroscopy, with information from molecular dynamics simulation. This work shows that βCD includes preferentially R-(–)-omeprazole, acting as a chiral selector. This discrimination of omeprazole enantiomers by cyclodextrins allows development of pharmaceutical formulations with a better bioavailability profile.

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Acknowledgments

This work was financially supported by PhD grants SFRH/BD/19175/2004 and SFRH/BD/17440/2004 and research grant POCI/SAU-OBS/55802/2004 from FCT (Fundação para a Ciência e a Tecnologia, Portugal). The authors would like to thank Belmac Laboratory, S.A. (Madrid, Spain) for kindly donating omeprazole and Roquette (Lestrem, France) for their support providing β CD and M β CD.

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Authors and Affiliations

  1. Laboratory of Pharmaceutical Technology, Faculty of Pharmacy, University of Coimbra, Coimbra, Portugal

    A. Figueiras & J. F. Veiga

  2. Department of Chemistry, Faculty of Sciences and Technology, University of Coimbra, Coimbra, Portugal

    J. M. G. Sarraguça & A. A. C. C. Pais

  3. NMR Spectroscopy Center, Department of Biochemistry, Faculty of Sciences and Technology, University of Coimbra, Coimbra, Portugal

    R. A. Carvalho

  4. Department of Biochemistry, University of Coimbra, Apartado 3126, 3001-401, Coimbra, Portugal

    R. A. Carvalho

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  1. A. Figueiras
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  2. J. M. G. Sarraguça
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  3. A. A. C. C. Pais
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  4. J. F. Veiga
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  5. R. A. Carvalho
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Correspondence to R. A. Carvalho.

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Figueiras, A., Sarraguça, J.M.G., Pais, A.A.C.C. et al. New insight into the discrimination between omeprazole enantiomers by cyclodextrins in aqueous solution. J Incl Phenom Macrocycl Chem 62, 345–351 (2008). https://doi.org/10.1007/s10847-008-9477-6

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  • DOI: https://doi.org/10.1007/s10847-008-9477-6

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