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Characteristic profiles of the inclusion complex of omeprazole/peracylated-β-cyclodextrin formed in supercritical carbon dioxide

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Abstract

Inclusion properties of the drug omeprazole (OMP) with peracetylated-beta-cyclodextrin (PAc-β-CD) prepared by green method, following supercritical carbon-dioxide (scCO2), were characterized through thermal (TGA and DSC), crystalline (XRD), NMR spectroscopic and dissolution studies. Comparison amongst PAc-β-CD, OMP, physical binary mixture (equimolar ratio of OMP: PAc-β-CD) and the solid inclusion complex (OMP/PAc-β-CD) revealed scCO2 as a successful technique for inclusion complex formation as well, identified characteristics performances of PAc-β-CD/OMP interactions. For instance, absence of characteristic DSC or XRD peaks of either chemical in the complex was quite noticeable with the shift of proton peaks in 1H NMR spectra. The formed inclusion complex also showed an important dissolution performance of OMP for controlled release applications partly due to the hydrophobic nature of PAc-β-CD.

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References

  1. Figueiras, A., Ribeiro, L., Teresa, M.: Preparation and physic-chemical characterization of omeprazole: methyl beta cyclodextrin inclusion complex in solid state. J. Incl. Phenom. Macrocycl. Chem. 57, 173–177 (2007)

    Article  CAS  Google Scholar 

  2. Figueiras, A., Carvalho, R.A., Ribeiro, L., Torres-Labandeira, J.J., Veiga, F.J.B.: Solid state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified β-cyclodextrin. Eur. J. Pharm. Biopharm. 67, 531–539 (2007)

    Article  CAS  Google Scholar 

  3. Marzocchi, L., Moyano, J.R., Rossi, A., Munoz, P., Arias, M.J., Giordano, F.: Current status of ATPase proton pump inhibitor complexation with cyclodextrins. Biol. J. Armen. 53, 176–193 (2001)

    CAS  Google Scholar 

  4. Riedel, A., Leopold, C.S.: Degradation of omeprazole induced by enteric polymer solutions and aqueous dispersions: HPLC investigations. Drug Dev. Ind. Pharm. 31, 151–160 (2005)

    Article  CAS  Google Scholar 

  5. Anibarro, M., Gessler, K., Uson, I., Sheldrick, G.M., Harata, K., Uekama, K., Hirayama, F., Abe, Y., Saenger, W.: Effect of peracylation of α-cyclodextrin on the molecular structure and on the formation of inclusion complexes: an X-ray study. J. Am. Chem. Soc. 123, 11854–11862 (2001)

    Article  CAS  Google Scholar 

  6. Castronuovo, G., Niccoli, M.: Thermodynamics of inclusion complexes of natural and modified cyclodextrins with propranolol in aqueous solution at 298 K. Bioorg. Med. Chem. 14, 3883–3887 (2006)

    Article  CAS  Google Scholar 

  7. Yang, X., Kim, J.C.: pH-Dependent release of blue dextran from carboxymethyl-β-cyclodextrin hydrogels. J. Ind. Eng. Chem. 16, 763–766 (2010)

    Article  CAS  Google Scholar 

  8. Loftsson, T., Brewester, M.: Pharmaceutical applications of cyclodextrins, drug solubilization and stabilization. J. Pharm. Sci. 85, 1017–1025 (1996)

    Article  CAS  Google Scholar 

  9. Beckman, E.J.: Super critical and near critical CO2 in green chemical synthesis and processing. J. Supercrit. Fluids 28, 121–191 (2004)

    Article  CAS  Google Scholar 

  10. Van Hees, T., Piel, G., Evrared, B., Otte, X., Thunnus, L., Delattre, L.: Application of supercritical carbon dioxide for the preparation of a piroxicam-β-cyclodextrin inclusion compound. Pharm. Res. 16, 1864–1870 (1999)

    Article  Google Scholar 

  11. Tozuka, Y., Fujito, T., Moribe, K., Yamamoto, K.: Ibuprofen-cyclodextrin inclusion complex formation using supercritical carbon dioxide. J. Incl. Phenom. Macrocycl. Chem. 56, 33–37 (2006)

    Article  CAS  Google Scholar 

  12. Bounaceur, A., Rodier, E., Fages, J.: Maturation of ketoprofen/β cyclodextrin mixture with supercritical carbon dioxide. J. Supercrit. Fluids 41, 429–439 (2007)

    Article  CAS  Google Scholar 

  13. Al-Marzouqi, A.H., Solieman, A., Shehadi, I., Adem, A.: Influence of the preparation method on the physicochemical properties of econazole-β-cyclodextrin complexes. J. Incl. Phenom. Macrocycl. Chem. 60, 85–93 (2008)

    Article  CAS  Google Scholar 

  14. He, J., Li, W.: Preparation of borneol-methyl-β-cyclodextrin inclusion complex by supercritical carbon dioxide processing. J. Incl. Phenom. Macrocycl. Chem. 65, 249–256 (2009)

    Article  CAS  Google Scholar 

  15. Lee, M.Y., Ganapathy, H.S., Lim, K.T.: Controlled drug release applications of the inclusion complex of peracetylated-b-cyclodextrin and water-soluble drugs formed in supercritical carbon dioxide. J. Phy. Chem. Solids 71, 630–633 (2010)

    Article  CAS  Google Scholar 

  16. Filardo, G., Di Blasi, M., Galia, A., Ponchel, A., Bricout, H., Sayede, A.D., Monflier, E.: Peracetylated-β-cyclodextrin as solubilizer of arylphosphines in supercritical carbon dioxide. J. Supercrit. Fluids 36, 173–181 (2006)

    Article  CAS  Google Scholar 

  17. Potluri, V.K., Hamilton, A.D., Karanikas, C.F., Bane, S.E., Xu, J., Beckman, E.J., Enick, R.M.: The high CO2-solubility of per-acetylated α-, β-, and γ-cyclodextrin. Fluid Phase Equilib. 211, 211–217 (2003)

    Article  CAS  Google Scholar 

  18. Hwang, H.S., Heo, J.Y., Jeong, Y.T., Jin, S.-H., Cho, D., Chang, T., Lim, K.T.: Preparation and properties of semifluorinated block copolymers of 2-(dimethylamino)ethyl methacrylate and fluorooctyl methacrylates. Polymer 44, 5153–5158 (2003)

    Article  CAS  Google Scholar 

  19. Veiga, M.D., Merino, M., Fernandez, D., Lozano, R.: Characterization of some cyclodextrin derivatives by thermal analysis. J. Therm. Anal. Calorim. 68, 511–516 (2002)

    Article  CAS  Google Scholar 

  20. Herchuelz, A., Carreer-Bruhwyler, F., Crommen, J., Chiam, P., Hubert, P., Messim, R., Dubois, C., Famaui, F.P., Gecjy, J.: Clinical pharmacokinetics of once-daily molsidomine: from immediate-release to prolonged-release once-daily formulations. Am. J. Drug Deliv. 2, 131–141 (2004)

    Article  CAS  Google Scholar 

  21. Schneider, H., Hacket, F., Rudiger, V., Ikeda, H.: NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 98, 1755–1786 (1998)

    Article  CAS  Google Scholar 

  22. Braga, S.S., Ribeiro-Claro, P., Pillinger, M., Gonçalves, I.S., Fernandes, A.C., Pereira, F., Romão, C.C., Correia, P.B., Teixeira-Dias, J.J.C.: Interactions of omeprazole and precursors with β-cyclodextrin host molecules. J. Incl. Phenom. Macrocycl. Chem. 47, 47–52 (2003)

    Article  CAS  Google Scholar 

  23. Brändström, A., Lindberg, P., Bergman, N.A., Alminger, T., Anker, K., Junggren, U., Lamm, B., Nordberg, P., Erickson, M., Grundevik, I., Hagin, I., Hoffmann, K., Johnsson, S., Larsson, S., Löfberg, I., Ohlson, K., Persson, B., Skänberg, I., Tekenbergs-Hjelte, L.: Chemical reactions of omeprazole and omeprazole analogues I. A survey of the chemical transformations of omeprazole and its analogues. Acta Chem. Scand. 43, 536–548 (1989)

    Article  Google Scholar 

  24. Nozawa, Y., Kishimoto, H.: Complex formation in amorphous powder mixture of β-cyclodextrin with medicinal drug by roll mixing procedures. J. Soc. Powder Technol. 29, 460–464 (1992)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This study was financially supported by Pukyong National University in the 2009 Post-Doc Program. This work was supported by Mid-career Researcher Program through NRF grant funded by the MEST (No. R01-2008-000-21056-0) and the second stage of BK 21 program.

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Authors and Affiliations

  1. Department of Imaging System Engineering, Pukyong National University, Busan, 608-739, Korea

    Tamanna Sultana, Jae Mok Jung & Kwon Taek Lim

  2. Department of Applied Chemistry and Chemical Engineering, University of Dhaka, Dhaka, 1000, Bangladesh

    Tamanna Sultana

  3. Division of Chemical Engineering, Pukyong National University, Busan, 608-739, Korea

    Seong-Soo Hong & Won-Ki Lee

  4. Polymer Chemistry Laboratory, College of Engineering, Kyungil University, Gyeongsan, Gyeongsangbuk-Do, 712-701, Korea

    Yeong-Soon Gal

  5. Korea Basic Science Institute, Busan Center, Busan, 618-230, Republic of Korea

    Hyun Gyu Kim

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  1. Tamanna Sultana
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  2. Jae Mok Jung
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  3. Seong-Soo Hong
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  7. Kwon Taek Lim
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Correspondence to Kwon Taek Lim.

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Sultana, T., Jung, J.M., Hong, SS. et al. Characteristic profiles of the inclusion complex of omeprazole/peracylated-β-cyclodextrin formed in supercritical carbon dioxide. J Incl Phenom Macrocycl Chem 72, 207–212 (2012). https://doi.org/10.1007/s10847-011-9966-x

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