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Study of the interaction between modified cyclodextrin and octopriox : potential applications in drug delivery

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Abstract

Host–guest interactions between the antifungal agent Octopirox® (Oc) and modified β-cyclodextrin-derivatives were studied using 1H- and 2D-ROESY NMR spectroscopy, Job-Plot and isothermal titration calorimetry (ITC). In addition to β-cyclodextrin (β-CD) a number of derivatives, namely randomly methacrylated β-cyclodextrin (RM-β-CD), mono-methacrylated β-cyclodextrin (MM-β-CD), randomly methylated β-cyclodextrin (RAMEB), hydroxypropyl-β-cyclodextrin (HP-β-CD) and randomly methacrylated hydroxypropyl-β-cyclodextrin (RM-HP-β-CD) were used. NMR data suggests the formation of highly ordered complexes, while ITC measurements allowed the identification of their stoichiometries and the thermodynamic data. To evaluate the possibility of retarded drug release from complexes prepared from polymeric materials like artificial nails, the complexes were polymerized with comonomers and subjected to aqueous extraction followed by quantification of Oc release by means of UV-spectroscopy.

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Authors and Affiliations

  1. Institute for Organic and Macromolecular Chemistry II, Heinrich-Heine-University Düsseldorf, Universitätsstraße 1, 40225, Düsseldorf, Germany

    C. Dollendorf, M. Maier & H. Ritter

  2. Medical Faculty, Centre of Dentistry, Department of Operative and Preventive Dentistry and Endodontics, Heinrich-Heine-University Düsseldorf, Moorenstraße 5, 40225, Düsseldorf, Germany

    R. Janda

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  1. C. Dollendorf
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  2. M. Maier
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  4. H. Ritter
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Correspondence to H. Ritter.

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Dollendorf, C., Maier, M., Janda, R. et al. Study of the interaction between modified cyclodextrin and octopriox : potential applications in drug delivery. J Incl Phenom Macrocycl Chem 77, 351–361 (2013). https://doi.org/10.1007/s10847-012-0254-1

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