Nanoparticles based on lipidyl-β-cyclodextrins: synthesis, characterization, and experimental and computational biophysical studies for encapsulation of atazanavir
| Autor: | Vincent Banchet, Sébastien Buchoux, Aurélien L. Furlan, Catherine Sarazin, Yong Miao, Mathieu Létévé, Véronique Bonnet, Virginie Lambertyn, Jean Michel |
|---|---|
| Přispěvatelé: | Génie Enzymatique et Cellulaire (GEC), Université de Technologie de Compiègne (UTC)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Recherche en Nanosciences - EA 4682 (LRN), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV), Interfaces biomatériaux/tissus hôtes, Université de Reims Champagne-Ardenne (URCA)-IFR53-Institut National de la Santé et de la Recherche Médicale (INSERM) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Aqueous solution Cyclodextrin technology industry and agriculture Nanoparticle 02 engineering and technology General Chemistry [CHIM.THER]Chemical Sciences/Medicinal Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Catalysis 3. Good health 0104 chemical sciences Bioavailability Molecular dynamics chemistry Chemical engineering Amphiphile Materials Chemistry Molecule [CHIM]Chemical Sciences 0210 nano-technology Stoichiometry ComputingMilieux_MISCELLANEOUS |
| Zdroj: | New Journal of Chemistry New Journal of Chemistry, Royal Society of Chemistry, 2018, 42 (24), pp.20171-20179. ⟨10.1039/c8nj03237h⟩ |
| ISSN: | 1144-0546 1369-9261 |
| Popis: | Amphiphilic cyclodextrins were synthesized from permethylated βCD with the aim of forming nanoparticles (NPs) that would encapsulate specific molecules (e.g. drugs) which could enhance their otherwise poor bioavailability. By grafting different fatty acids, four amphiphilic CDs were obtained. The self-assembling properties of three of these compounds were evaluated demonstrating micromolar critical aggregation concentration (CAC). Additionally, the stability of these nanoparticles was studied revealing that the compounds with C18 chains could be stored at 4 °C for prolonged periods without any issue. Finally, reliable characterization of NPs made of di-oleoyl-glycerolipidyl-β-cyclodextrin (DOCD) was performed by combining DLS, cryo-transmission electron microscopy (cryo-TEM) and molecular dynamics (MD) simulations. This revealed that DOCD nano-assemblies are roughly nano-scaled, spherical objects (diameter ca. 120 nm) without internal organization or aqueous compartments. Finally, atazanavir, used as a model drug, was entrapped in NPs whilst MD simulations were used to investigate molecule entrapment. This revealed that atazanavir interacts with DOCD to form a drug-loaded NP which does not fit with the 2 : 1 stoichiometry encapsulation classically observed in the cyclodextrin cavity. |
| Databáze: | OpenAIRE |
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