On the encapsulation of Olsalazine by β-cyclodextrin: A DFT-based computational and spectroscopic investigations
| Autor: | Amina S. Aljaber, Abdulilah Dawoud Bani-Yaseen |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
ONIOM
Supramolecular chemistry 02 engineering and technology Molecular Dynamics Simulation 010402 general chemistry DFT 01 natural sciences Analytical Chemistry Molecular dynamics Computational chemistry Computational methods Molecular orbital Instrumentation Spectroscopy chemistry.chemical_classification Cyclodextrin Chemistry Hydrogen bond beta-Cyclodextrins Intermolecular force β-Cyclodextrin Olsalazine 021001 nanoscience & nanotechnology Binding constant UV–vis spectroscopy Atomic and Molecular Physics and Optics 0104 chemical sciences Aminosalicylic Acids Inclusion complexes Encapsulation TD-DFT 0210 nano-technology |
| Zdroj: | Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 214:531-536 |
| ISSN: | 1386-1425 |
| DOI: | 10.1016/j.saa.2019.02.030 |
| Popis: | In this work, the supramolecular host-guest interaction of the prodrug Olsalazine (OLZ) and β-Cyclodextrin (β-CD) was examined experimentally and computationally. Experimentally, employing the UV–Vis spectroscopic method in aqueous media at various pH's, results obtained using the Benesi-Hilderbrand approach demonstrated that OLZ can form supramolecular inclusion complex with β-CD with stoichiometric ratio of 1:1. Furthermore, these results revealed that the formation of OLZ: β-CD complexes exhibited insignificant pH dependency in the range 5–8 with an average binding constant (Kb) of approximately 1 × 103 M−1. Computationally, geometry optimization of 1:1 OLZ: β-CD complexes was performed employing the ONIOM (DFT((ωB97XB)/6–31 + G(d)),SQM(PM3)) approach. Obtained results demonstrated that OLZ: β-CD complex is stabilized by the formation of intermolecular hydrogen bonds with an average length of approximately 1.8 A. Additionally, the stability of OLZ: β-CD complex was demonstrated employing ADMP molecular dynamic simulations over a timeframe of 500 fs. The molecularity of the supramolecular host-guest interaction between OLZ and β-CD is presented and interpreted in the essence of TD-DFT and molecular orbitals analyses. |
| Databáze: | OpenAIRE |
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