Synthesis and characterization of a new cyclodextrin derivative with improved properties to design oral dosage forms
| Autor: | María D. Vasconi, Lucila Isabel Hinrichsen, Maria Celina Lamas, Ana Victoria Codina, Josefina Priotti, Ariel D. Quiroga, Darío Leonardi, Agustina García |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
CYCLODEXTRINS
Farmacología y Farmacia CIENCIAS MÉDICAS Y DE LA SALUD Otras Ciencias Biológicas Administration Oral Pharmaceutical Science 02 engineering and technology SYNTHESIS Albendazole 030226 pharmacology & pharmacy Dosage form Ciencias Biológicas 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Differential scanning calorimetry Animals Solubility Dissolution Trichinella spiralis Anthelmintics chemistry.chemical_classification PHYSICOCHEMICAL CHARACTERIZATION Calorimetry Differential Scanning Molecular Structure Cyclodextrin beta-Cyclodextrins Nuclear magnetic resonance spectroscopy 021001 nanoscience & nanotechnology Medicina Básica chemistry Stability constants of complexes Drug Design Microscopy Electron Scanning ALBENDAZOLE 0210 nano-technology POORLY WATER-SOLUBLE DRUG Derivative (chemistry) CIENCIAS NATURALES Y EXACTAS Nuclear chemistry |
| DOI: | 10.1007/s13346-018-0591-8 |
| Popis: | This work aimed to synthesize a novel β-cyclodextrin derivative, itaconyl-β-cyclodextrin to evaluate whether albendazole inclusion complexes with the new β-cyclodextrin derivative-improved albendazole dissolution efficiency and its anthelminthic activity. The new derivative was thoroughly evaluated and characterized, and an average degree of substitution of 1.4 per cyclodextrin molecule was observed. Albendazole:itaconyl-β-cyclodextrin complexes were prepared by spray drying procedures and investigated using phase solubility diagrams, dissolution efficiency, X-ray diffraction, differential scanning calorimetry, Fourier transform infrared, scanning electronic microscopy, mass spectrometry, and nuclear magnetic resonance spectroscopy. Phase solubility diagrams and mass spectrometry studies showed that the inclusion complex was formed in an equimolar ratio. Stability constant values were 602 M −1 in water, and 149 M −1 in HCl 0.1 N. Nuclear magnetic resonance experiments of the inclusion complex showed correlation signals between the aromatic and propyl protons of albendazole and the itaconyl-β-cyclodextrin inner protons. The studies indicated solid structure changes of albendazole included in itaconyl-β-cyclodextrin. The maximum drug release was reached at 15 min, and the inclusion complex solubility was 88-fold higher than that of the pure drug. The in vitro anthelmintic activity assay showed that the complex was significantly more effective than pure albendazole. Fil: García, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Priotti, Josefina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Codina, Ana Victoria. Universidad Nacional de Rosario. Facultad de Ciencias Medicas. Instituto de Genetica Experimental; Argentina Fil: Vasconi, María Delia. Universidad Nacional de Rosario. Facultad de Ciencias Medicas. Instituto de Genetica Experimental; Argentina Fil: Quiroga, Ariel Dario. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Fisiología Experimental. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Fisiología Experimental; Argentina Fil: Hinrichsen, Lucila Isabel. Universidad Nacional de Rosario. Facultad de Ciencias Medicas. Instituto de Genetica Experimental; Argentina Fil: Leonardi, Darío. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina Fil: Lamas, Maria Celina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|