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Journal of Drug Delivery
Volume 2014, Article ID 575719, 10 pages
http://dx.doi.org/10.1155/2014/575719
Research Article

Interaction Study of an Amorphous Solid Dispersion of Cyclosporin A in Poly-Alpha-Cyclodextrin with Model Membranes by 1H-, 2H-, 31P-NMR and Electron Spin Resonance

1IRBA, RNI-Biophysics Laboratory, 24, avenue des Maquis du Grésivaudan, BP 82, 38702 La Tronche Cedex, France
2Galenic Pharmaceutical Laboratory, LAGEP UMR CNRS 5007, UFR Medicine and Pharmacy, 22 boulevard Gambetta, 76183 Rouen, France

Received 4 December 2013; Revised 21 March 2014; Accepted 31 March 2014; Published 5 May 2014

Academic Editor: Juan M. Irache

Copyright © 2014 Jean-Claude Debouzy et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. G. A. Knoll and R. C. Bell, “Tacrolimus versus cyclosporin for immunosuppression in renal transplantation: meta-analysis of randomised trials,” British Medical Journal, vol. 318, no. 7191, pp. 1104–1107, 1999. View at Google Scholar · View at Scopus
  2. D. J. G. White and R. Y. Calne, “The use of cyclosporin A immunosuppression in organ grafting,” Immunological Reviews, vol. 65, no. 1, pp. 115–131, 1982. View at Google Scholar · View at Scopus
  3. S. Joudieh, M. Lahiani-Skiba, P. Bon, O. Ba, J. M. Le Breton, and M. Skiba, “Nimesulide apparent solubility enhancement with natural cyclodextrins and their polymers,” Letters in Drug Design and Discovery, vol. 5, no. 6, pp. 406–415, 2008. View at Publisher · View at Google Scholar · View at Scopus
  4. T. Boukhris, M. Lahiani-Skiba, F. Bounoure, and M. Skiba, “New approach for pre-formulation of an oral cyclosporine,” Digest Journal of Nanomaterials and Biostructures, vol. 7, no. 1, pp. 155–164, 2012. View at Google Scholar · View at Scopus
  5. C. Sommerer, O. Hergesell, A.-M. Nahm et al., “Cyclosporin A toxicity of the renal allograft—a late complication and potentially reversible,” Nephron, vol. 92, no. 2, pp. 339–345, 2002. View at Google Scholar · View at Scopus
  6. L. Stuhne-Sekalec and N. Z. Stanacev, “Interaction of cyclosporin A with 1,2-dimyristoyl-sn-glycero-3-phosphocholine unilamellar vesicles studied by electron spin resonance,” Chemistry and Physics of Lipids, vol. 48, no. 1-2, pp. 1–6, 1988. View at Google Scholar · View at Scopus
  7. M. P. Lambros and Y. E. Rahman, “Effects of cyclosporin A on model lipid membranes,” Chemistry and Physics of Lipids, vol. 131, no. 1, pp. 63–69, 2004. View at Publisher · View at Google Scholar · View at Scopus
  8. T. S. Wiedmann, T. Trouard, S. C. Shekar, M. Polikandritou, and Y.-E. Rahman, “Interaction of cyclosporin A with dipalmitoylphosphatidylcholine,” Biochimica et Biophysica Acta: Biomembranes, vol. 1023, no. 1, pp. 12–18, 1990. View at Publisher · View at Google Scholar · View at Scopus
  9. M. Roux, J.-M. Neumann, M. Bloom, and P. F. Devaux, “2H and 31P NMR study of pentalysine interaction with headgroup deuterated phosphatidylcholine and phosphatidylserine,” European Biophysics Journal, vol. 16, no. 5, pp. 267–273, 1988. View at Publisher · View at Google Scholar · View at Scopus
  10. J.-C. Debouzy, J.-M. Neumann, M. Herve, D. Daveloose, J. Viret, and R. Apitz-Castro, “Interaction of antiaggregant molecule ajoene with membranes. An ESR and 1H, 2H, 31P-NMR study,” European Biophysics Journal, vol. 17, no. 4, pp. 211–216, 1989. View at Google Scholar · View at Scopus
  11. J.-P. Douliez, A. Léonard, and E. J. Dufourc, “Conformational order of DMPC sn-1 versus sn-2 chains and membrane thickness: an approach to molecular protrusion by solid state 2H-NMR and neutron diffraction,” Journal of Physical Chemistry, vol. 100, no. 47, pp. 18450–18457, 1996. View at Google Scholar · View at Scopus
  12. O. Heintz, P. Bossanne, F. Fauvelle, and J.-C. Debouzy, “Interaction between 4-hydroxynonenane with membrane system. 1H, 31P, 2H NMR study,” Annales Pharmaceutiques Francaises, vol. 53, no. 1, pp. 24–28, 1995. View at Google Scholar · View at Scopus
  13. J. K. Sanders, B. K. Hunter, and C. Griesinger, “Modern NMR spectroscopy,” Angewandte Chemie, vol. 33, no. 19, pp. 1992–1993, 1994. View at Publisher · View at Google Scholar
  14. M. Skiba, “Method for synthesizing calixarene and/or cyclodextrin copolymers, terpolymers and tetrapolymers, and uses thereof,” Patent PCT/FR2010/000876, 2010.
  15. M. Skiba and M. Lahiani-Skiba, “Novel method for preparation of cyclodextrin polymers: physico-chemical characterization and cytotoxicity,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 75, no. 3-4, pp. 341–349, 2013. View at Publisher · View at Google Scholar
  16. F. Djedaini and B. Perly, “Nuclear magnetic resonance of cyclodextrins, derivatives and inclusion compounds,” in New Trends in Cyclodextrin and Derivatives, pp. 217–246, 1991. View at Google Scholar
  17. P. Job, “Etude spectrographique de la formation de complexes en solution et de leur stabilité,” Comptes Rendus de l’Académie des Sciences, vol. 180, pp. 918–930, 1925. View at Google Scholar
  18. T. Loftsson, M. E. Brewster, and M. Másson, “Role of cyclodextrins in improving oral drug delivery,” American Journal of Drug Delivery, vol. 2, no. 4, pp. 261–275, 2004. View at Publisher · View at Google Scholar · View at Scopus
  19. J. C. Debouzy, A. Gadelle, J. Y. Pailler et al., “In vitro cellular toxicity and in vivo lethality studies of alkylated α-anhydro cyclodextrins,” S.T.P. Pharma Sciences, vol. 13, no. 3, pp. 209–214, 2003. View at Google Scholar · View at Scopus
  20. E. J. Dufourc, J.-F. Faucon, and G. Fourche, “Reversible disc-to-vesicle transition of melittin-DPPC complexes triggered by the phospholipid acyl chain melting,” FEBS Letters, vol. 201, no. 2, pp. 205–209, 1986. View at Google Scholar · View at Scopus
  21. J. Seelig and A. Seelig, “Lipid conformation in model membranes and biological membranes,” Quarterly Reviews of Biophysics, vol. 13, no. 1, pp. 19–61, 1980. View at Google Scholar · View at Scopus
  22. L. J. Burnett and B. H. Muller, “Deuteron quadrupole coupling constants in three solid deuterated paraffin hydrocarbons: C2D6, C4D10, C6D14,” The Journal of Chemical Physics, vol. 55, no. 12, pp. 5829–5831, 1971. View at Google Scholar · View at Scopus
  23. A. Górnicki and A. Gutsze, “In vitro effects of ozone on human erythrocyte membranes: an EPR study,” Acta Biochimica Polonica, vol. 47, no. 4, pp. 963–971, 2000. View at Google Scholar · View at Scopus
  24. V. M. S. Gil and N. C. Oliveira, “On the use of the method of continuous variations,” Journal of Chemical Education, vol. 67, no. 6, pp. 473–478, 1990. View at Google Scholar · View at Scopus
  25. C. Baudin, C. Pean, B. Pellizzari et al., “2-O-substituted-3,6-per-anhydro-α-cyclodextrin as potential biocompatible agents for the selective complexation of heavy metal ions with special attention to lead,” Journal of Inclusion Phenomena, vol. 38, no. 1–4, pp. 287–296, 2000. View at Google Scholar · View at Scopus
  26. D. G. Gorenstein, Phosphorous-31 NMR: Principles and Applications, Elsevier, 1984.
  27. T. Boukhris, M. Lahiani-Skiba, and M. Skiba, “Novel oral formulation of cyclosporine-spray-dried dispersion using cyclodextrin copolymers,” Digest Journal of Nanomaterials and Biostructures, vol. 7, no. 1, pp. 143–154, 2012. View at Google Scholar · View at Scopus
  28. T. Higuchi and K. A. Connors, “Phase-solubility techniques,” Advances in Analytical Chemistry and Instrumentation, vol. 4, no. 2, pp. 117–212, 1965. View at Google Scholar
  29. F. Fava and V. F. Ciccotosto, “Effects of randomly methylated-β-cyclodextrins (RAMEB) on the bioavailability and aerobic biodegradation of polychlorinated biphenyls in three pristine soils spiked with a transformer oil,” Applied Microbiology and Biotechnology, vol. 58, no. 3, pp. 393–399, 2002. View at Publisher · View at Google Scholar · View at Scopus
  30. R. C. Petter, J. S. Salek, C. T. Sikorski, G. Kumaravel, and F.-T. Lin, “Cooperative binding by aggregated mono-6-(alkylamino)-β-cyclodextrins,” Journal of the American Chemical Society, vol. 112, no. 10, pp. 3860–3868, 1990. View at Google Scholar · View at Scopus
  31. C. Enguehard-Gueiffier, F. Fauvelle, J.-C. Debouzy et al., “2,3-Diarylimidazo[1,2-a]pyridines as potential inhibitors of UV-induced keratinocytes apoptosis: synthesis, pharmacological properties and interactions with model membranes and oligonucleotides by NMR,” European Journal of Pharmaceutical Sciences, vol. 24, no. 2-3, pp. 219–227, 2005. View at Publisher · View at Google Scholar · View at Scopus
  32. T. J. O'Leary, P. D. Ross, M. R. Lieber, and I. W. Levin, “Effects of cyclosporine A on biomembranes. Vibrational spectrospcopic, calorimetric and hemolysis studies,” Biophysical Journal, vol. 49, no. 4, pp. 795–801, 1986. View at Google Scholar · View at Scopus
  33. H. R. Loosli, H. Kessler, and H. Oschkinat, “The conformation of cyclosporin A in the crystal and in solution,” Helvetica Chimica Acta, vol. 68, no. 3, pp. 682–704, 1985. View at Google Scholar · View at Scopus
  34. U. Schote, P. Ganz, A. Fahr, and J. Seelig, “Interactions of cyclosporines with lipid membranes as studied by solid-state nuclear magnetic resonance spectroscopy and high-sensitivity titration calorimetry,” Journal of Pharmaceutical Sciences, vol. 91, no. 3, pp. 856–867, 2002. View at Publisher · View at Google Scholar · View at Scopus