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Grafting β-Cyclodextrins to Silicone, Formulation of Emulsions and Encapsulation of Antifungal Drug

  • Conference paper
Silicon Based Polymers

Abstract

Emulsions of silicone polymers having β-cyclodextrin units as lateral chains have been prepared and used for the encapsulation of the antifungal drug griseofulvin. Such technology enables the formulation of active substances that are not soluble in water as dosage forms for topical administration.

Chemical grafting of monoallyl derivative of β-cyclodextrins to poly(methylhydrosiloxane) polymer or to poly(methylhydrosiloxane-co-dimethylsiloxane) copolymer through hydrosilylation reaction was investigated. Grafting of β-cyclodextrins to the Si-H units was limited by steric hindrance of the bulky cyclic D-heptaglucopyranoside. Therefore the kinetics of the grafting reaction slowed down dramatically as the conversion increased. The way to achieve high grafting rates was to run the grafting reaction for a very long time. The full conversion of the poly(methylhydrosiloxane) homopolymer could not be reached.

The grafted silicone polymers have been emulsified by the “spontaneous emulsification” method. The emulsification took advantage of the very low solubility of the polymers in water. Stable emulsions with sizes ranging between 200 and 500 nm have been produced.

The emulsions of β-cyclodextrins grafted on silicone could encapsulate the antifungal substance griseofulvin inside the β-cyclodextrin cavity by formation of inclusion complex. The encapsulation rate was limited to the 1:1 stoichiometry of the complex. Supplementary amount of griseofulvin slowly precipitated as crystalline particles in the aqueous phase.

There are several benefits of using a silicone polymer with grafted β–cyclodextrin units. The silicone backbone is biocompatible and adherent to the skin. Grafted β-cyclodextrin units enable the incorporation of griseofulvin in silicone oil. Lastly, the encapsulation of griseofulvin as inclusion complexes during the “spontaneous emulsification” process is quite easy. Let us recall that the formation of an inclusion complex of griseofulvin and the water-soluble β-cyclodextrin is a very difficult task owing to the low solubility of griseofulvin in water.

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Author information

Authors and Affiliations

  1. Laboratoire d’Automatique et de Génie des Procédés (LAGEP), UMR 5007 CNRS – Université Claude Bernard Lyon 1, University of Lyon, 69622, Villeurbanne, France

    Ahlem Noomen, Alexandra Penciu & Yves Chevalier

  2. Laboratoire de Physico-Chimie des Matériaux Solides, Faculté des Sciences de Tunis, Manar II, 2092, Tunis, Tunisia

    Ahlem Noomen, Souhaira Hbaieb, Noureddine Amdouni & Rafik Kalfat

  3. University of Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), UMR 5246 CNRS – Université Claude Bernard Lyon 1, 69622, Villeurbanne, France

    Ahlem Noomen

  4. Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), UMR 5246 CNRS – Université Claude Bernard Lyon 1, 69622, Villeurbanne, France

    Hélène Parrot-Lopez

  5. University of Lyon, Institut National de Recherche et d’Analyse Physico-chimique, Púle Technologique Sidi-Thabet, 2020, Sidi-Thabet, Tunisia

    Rafik Kalfat

Authors
  1. Ahlem Noomen
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  2. Alexandra Penciu
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  3. Souhaira Hbaieb
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  4. Hélène Parrot-Lopez
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  5. Noureddine Amdouni
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  6. Yves Chevalier
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  7. Rafik Kalfat
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Editors and Affiliations

  1. Ecole Nationale Supérieure de Chimie de Montpellier, UMR 5253 - Institut Charles Gerhardt, Ingénierie et Architectures Macromoléculaires, 8 rue de l’Ecole Normale, 34296, Montpellier CX 05, France

    François Ganachaud

  2. Institut de Chimie et des Matériaux, Paris-Est (ICMPE) SPC-CNRS, 2 à 8 rue Henri Dunant, 94320, Thiais, France

    Sylvie Boileau

  3. Université Montpellier II, Institut Charles Gerhardt, Chimie Moléculaire et organisation du solide, place Eugène Bataillon, 34095, Montpellier CX 05, France

    Bruno Boury

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Noomen, A. et al. (2008). Grafting β-Cyclodextrins to Silicone, Formulation of Emulsions and Encapsulation of Antifungal Drug. In: Ganachaud, F., Boileau, S., Boury, B. (eds) Silicon Based Polymers. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-8528-4_12

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