Spectroscopic characterisation of the inclusion complexes between the antifungal drugs naftifine and terbinafine and cyclodextrins |
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Authors: | M. Uzqueda G. González-Gaitano D. Wouessidjewe A. Zornoza M. Sánchez C. Martín |
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Affiliation: | 1. Department of Chemistry and Soil Sciences (Physical Chemistry) , University of Navarra , C/Irunlarrea s/n 31080, Pamplona, Navarra, Spain;2. Pharmacotechnie, DPM-UMR 5063 UJF/CNRS , Université Joseph Fourier – Grenoble I , 5 av. de Verdun, 38243, Meylan Cedex, France |
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Abstract: | The complexation of naftifine (NF) and terbinafine (TB) with cyclodextrins (CDs) has been investigated by UV/visible and 1H NMR spectroscopy, ROESY techniques and also ESI-MS. Both drugs form 1:1 inclusion complexes with all the CDs tested except with α-CD, as deduced from the Benesi–Hildebrand plots and confirmed by ESI-MS and NMR spectroscopy (Job plot method). The K 11 values for NF decrease in the order β-CD > methylated β-CD > 2-hydroxypropyl-β-CD >γ-CD. The determination of the enthalpy and entropy provides information about the main driving forces in the process. The stability constants of the complexes NF–β-CD, TB–β-CD and TB–γ-CD determined by 1H NMR spectroscopy are in agreement with the values obtained by UV. For TB–β-CD, the value is higher, due to the fact that the length of the TB aliphatic chain allows a deeper inclusion of the naphthalene group inside the corresponding β-CD molecule, according to the 2D ROESY experiments. |
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Keywords: | terbinafine naftifine cyclodextrins inclusion complex characterisation |
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