Article (Scientific journals)
Molecular Modeling Study of Beta- and Gamma-Cyclodextrin Complexes with Miconazole
Piel, Géraldine; Dive, Georges; Evrard, Brigitte et al.
2001In European Journal of Pharmaceutical Sciences, 13 (3), p. 271-9
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Keywords :
Miconazole; Cyclodextrins; Molecular modeling; Complex structure; AM1 calculations
Abstract :
[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.
Disciplines :
Chemistry
Pharmacy, pharmacology & toxicology
Author, co-author :
Piel, Géraldine ;  Université de Liège - ULiège > Département de pharmacie > Pharmacie galénique et magistrale
Dive, Georges ;  Université de Liège - ULiège > Centre d'ingénierie des protéines
Evrard, Brigitte  ;  Université de Liège - ULiège > Département de pharmacie > Pharmacie galénique
Van Hees, Thierry ;  Université de Liège - ULiège > Département de pharmacie > Pharmacie clinique
Henry de Hassonville, Sandrine
Delattre, Luc ;  Université de Liège - ULiège > Département de pharmacie > Département de pharmacie
Language :
English
Title :
Molecular Modeling Study of Beta- and Gamma-Cyclodextrin Complexes with Miconazole
Publication date :
June 2001
Journal title :
European Journal of Pharmaceutical Sciences
ISSN :
0928-0987
eISSN :
1879-0720
Publisher :
Elsevier
Volume :
13
Issue :
3
Pages :
271-9
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 12 August 2009

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