Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone
| Autor: | J. I. N. Oliveira, Ariana Zoppi, Arnóbio Antônio da Silva-Júnior, Matheus F. Fernandes-Pedrosa, Arthur S. A. de Medeiros, Marcela Raquel Longhi, Euzébio Guimarães Barbosa |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
CYCLODEXTRINS
Polymers and Plastics Supramolecular chemistry 02 engineering and technology INGENIERÍAS Y TECNOLOGÍAS Molecular Dynamics Simulation Triamcinolone 010402 general chemistry Ring (chemistry) 01 natural sciences Molecular mechanics Molecular dynamics purl.org/becyt/ford/2.10 [https] Carbohydrate Conformation Materials Chemistry medicine Organic chemistry Solubility Conformational isomerism TERNARY COMPLEXES Nanotecnología Drug Carriers Chemistry beta-Cyclodextrins Organic Chemistry 021001 nanoscience & nanotechnology Nano-materiales Combinatorial chemistry TRIAMCINOLONE 0104 chemical sciences OLIGOSACCHARIDES purl.org/becyt/ford/2 [https] Triethanolamine Solvents SUPRAMOLECULAR AGGREGATES Thermodynamics CO-SOLVENTS 0210 nano-technology Ternary operation medicine.drug |
| Zdroj: | CONICET Digital (CONICET) Consejo Nacional de Investigaciones Científicas y Técnicas instacron:CONICET |
| Popis: | A second compound is generally associated with oligosaccharides as a strategy to maximize the solubilizing effect for nonpolar compounds. This study elucidated the role and the mechanism whereby liquid compounds interact in these supramolecular aggregates in the solubilization of triamcinolone. Three different oligosaccharides (beta-cyclodextrin, 2-hydroxipropil-beta-cyclodextrin, and randomly methylated beta-cyclodextrin) and two potent co-solvents (triethanolamine and N-methyl pyrrolidone) were carefully evaluated by using three distinct experimental approaches. Incredibly stable complexes were formed with cyclodextrins (CDs). The structure of the complexes was elucidated by magnetic resonance spectra 2D-ROESY. The interactions of the protons of ring “A” of the drug with H3 and H5 protons of the CD cavity observed in the binary complexes remained in both ternary complexes. Unlike the observed ternary associations with triethanolamine, N-methyl pyrrolidone competed with the triamcinolone CD cavity and considerably decreased the stability of the complex and the solubility of the drug. The molecular dynamics (MD) and quantum mechanics:molecular mechanics (QM:MM) calculations supported that triethanolamine stabilized the drug-CD interactions for the conformer identified in the 2D-ROESY experiments, improving the quality and uniformity of the formed complex. The role played by the co-solvent in the ternary complexes depends on its specific ability to interact with the CD cavity in the presence of the drug, which can be predicted in theoretical studies to select the best candidate. Fil: Medeiros, Arthur S. A. de. Universidade Federal do Rio Grande do Norte; Brasil Fil: Zoppi, Ariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina Fil: Barbosa, Euzébio G.. Universidade Federal do Rio Grande do Norte; Brasil Fil: Oliveira, Jonas I. N.. Universidade Federal do Rio Grande do Norte; Brasil Fil: Fernandes Pedrosa, Matheus F.. Universidade Federal do Rio Grande do Norte; Brasil Fil: Longhi, Marcela Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina Fil: Silva Júnior, Arnóbio A. da. Universidade Federal do Rio Grande do Norte; Brasil |
| Databáze: | OpenAIRE |
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