Comparative Study of the Inclusion Complexation of Pizotifen and Ketotifen with Native and Modified Cyclodextrins
| Autor: | Adnan A. Badwan, Mohammad B. Zughul, Musa I. El-Barghouthi, Mahmoud M. Al Omari, J. Eric D. Davies |
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| Rok vydání: | 2007 |
| Předmět: |
chemistry.chemical_classification
Ketotifen Cyclodextrin Enthalpy Biophysics Biochemistry Medicinal chemistry Hydrophobic effect chemistry.chemical_compound chemistry Ionic strength medicine Proton NMR Thiophene Organic chemistry Physical and Theoretical Chemistry Solubility Molecular Biology medicine.drug |
| Zdroj: | Journal of Solution Chemistry. 37:249-264 |
| ISSN: | 1572-8927 0095-9782 |
| DOI: | 10.1007/s10953-007-9234-2 |
| Popis: | The interaction of two benzocycloheptanes namely, pizotifen (Pizo) and ketotifen (Keto), with cyclodextrins (CDs: α-, β-, γ-, and HP-β-CDs) has been investigated by several techniques including phase solubility, X-ray powder diffractometry, 1H-nuclear magnetic resonance and molecular mechanical modeling. The effects of CD type, pH, ionic strength and temperature on complex stability were also explored. The complex formation constant (K11) values for the Pizo/CD system follows the decreasing order β-CD > γ-CD > HP-β-CD > α-CD. However, for the Keto/CD system it follows the decreasing order γ-CD > β-CD > HP-β-CD > α-CD. The tendency of Pizo and Keto to complex with β-CD is driven to the extent of 70% by the hydrophobic effect. Complex formation of Keto and Pizo was substantially driven by entropy (>100 J⋅mol−1⋅K−1) but slightly retarded by enthalpy (3–8 kJ⋅mol−1). 1H-NMR and MM+ studies indicate multimodal inclusion of the methylpiperadine, thiophene and phenyl moieties into the β-CD cavity. |
| Databáze: | OpenAIRE |
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