Reference : Molecular Modeling Study of Beta- and Gamma-Cyclodextrin Complexes with Miconazole
Scientific journals : Article
Human health sciences : Pharmacy, pharmacology & toxicology
Physical, chemical, mathematical & earth Sciences : Chemistry
http://hdl.handle.net/2268/18561
Molecular Modeling Study of Beta- and Gamma-Cyclodextrin Complexes with Miconazole
English
Piel, Géraldine mailto [Université de Liège - ULg > Département de pharmacie > Pharmacie galénique et magistrale >]
Dive, Georges mailto [Université de Liège - ULg > > Centre d'ingénierie des protéines >]
Evrard, Brigitte mailto [Université de Liège - ULg > Département de pharmacie > Pharmacie galénique >]
Van Hees, Thierry mailto [Université de Liège - ULg > Département de pharmacie > Pharmacie clinique]
Henry de Hassonville, Sandrine [ > > ]
Delattre, Luc mailto [Université de Liège - ULg > Département de pharmacie > Département de pharmacie >]
Jun-2001
European Journal of Pharmaceutical Sciences
Elsevier
13
3
271-9
Yes (verified by ORBi)
International
0928-0987
[en] Miconazole ; Cyclodextrins ; Molecular modeling ; Complex structure ; AM1 calculations
[en] Different authors have demonstrated the inclusion of miconazole in cyclodextrins (CD). Miconazole can be included in the CD cavity both in the neutral and in the ionized form. The present study tries to understand which fragment of the miconazole molecule is involved in the inclusion. Austin Model 1 approximate molecular orbital calculations have been performed on several complexes between beta-cyclodextrin (betaCD) or gamma-cyclodextrin (gammaCD) and miconazole in the ionized and the non-ionized forms of the two R and S enantiomers in three different orientations. We observed that betaCD is a good vehicle to transport miconazole which can be very easily released. The complexation energy between miconazole and betaCD is not very high but the entropic factor has a great incidence on the stability of the formed complex. The inclusion of the dichlorobenzene-CH(2)-O- and of the imidazole part of the S isomer gives rise to the most probable complex in acidic conditions (ionized miconazole). Nevertheless, the inclusion should be considered as a dynamic process in which different parts of the molecule could be alternatively included in betaCD. The present work demonstrates the high capability of deformation of betaCD which could easily accommodate several types of ligand. By opposite, the cycle extension in gammaCD leads to a more rigid vehicle with regards to miconazole.
Researchers ; Professionals
http://hdl.handle.net/2268/18561

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