Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion Complexes
Rutin is a natural flavonoid that carries out a variety of biological activities, but its application in medicine and food is limited by its water solubility. One of the classical methods used to enhance drug solubility is encapsulation with cyclodextrins. In this paper, the encapsulation of differe...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-01-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/3/955 |
| _version_ | 1827759849967976448 |
|---|---|
| author | Chaokang Chang Meng Song Mingxing Ma Jihong Song Fengyi Cao Qi Qin |
| author_facet | Chaokang Chang Meng Song Mingxing Ma Jihong Song Fengyi Cao Qi Qin |
| author_sort | Chaokang Chang |
| collection | DOAJ |
| description | Rutin is a natural flavonoid that carries out a variety of biological activities, but its application in medicine and food is limited by its water solubility. One of the classical methods used to enhance drug solubility is encapsulation with cyclodextrins. In this paper, the encapsulation of different cyclodextrins with rutin was investigated using a combination of experimental and simulation methods. Three inclusions of rutin/beta-cyclodextrin (β-CD), rutin/2-hydroxypropyl beta-cyclodextrin (HP-β-CD) and rutin/2,6-dimethyl beta-cyclodextrin (DM-β-CD) were prepared by the freeze-drying method, and the inclusions were analyzed using Fourier infrared spectroscopy (FTIR), X-ray diffraction analysis (XRD), differential scanning calorimetry (DSC) and ultraviolet–visible spectroscopy (UV) to characterize and demonstrate the formation of the inclusion complexes. Phase solubility studies showed that rutin formed a 1:1 stoichiometric inclusion complex and significantly increased its solubility. β-CD, HP-β-CD, DM-β-CD, rutin and the three inclusion complexes were modeled by using MS2018 and AutoDock 4.0, and molecular dynamics simulations were performed to calculate the solubility parameters, binding energies, mean square displacement (MSD), hydrogen bonding and radial distribution functions (RDF) after the equilibration of the systems. The results of simulation and experiment showed that rutin/DM-β-CD had the best encapsulation effect among the three cyclodextrin inclusion complexes. |
| first_indexed | 2024-03-11T09:34:25Z |
| format | Article |
| id | doaj.art-6600d86a40a0436ea25552801c0f3251 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T09:34:25Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-6600d86a40a0436ea25552801c0f32512023-11-16T17:25:43ZengMDPI AGMolecules1420-30492023-01-0128395510.3390/molecules28030955Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion ComplexesChaokang Chang0Meng Song1Mingxing Ma2Jihong Song3Fengyi Cao4Qi Qin5School of Materials and Chemical Engineering, Zhongyuan University of Technology, Zhengzhou 450007, ChinaSchool of Materials and Chemical Engineering, Zhongyuan University of Technology, Zhengzhou 450007, ChinaSchool of Materials and Chemical Engineering, Zhongyuan University of Technology, Zhengzhou 450007, ChinaSchool of Materials and Chemical Engineering, Zhongyuan University of Technology, Zhengzhou 450007, ChinaSchool of Materials and Chemical Engineering, Zhongyuan University of Technology, Zhengzhou 450007, ChinaSchool of Materials and Chemical Engineering, Zhongyuan University of Technology, Zhengzhou 450007, ChinaRutin is a natural flavonoid that carries out a variety of biological activities, but its application in medicine and food is limited by its water solubility. One of the classical methods used to enhance drug solubility is encapsulation with cyclodextrins. In this paper, the encapsulation of different cyclodextrins with rutin was investigated using a combination of experimental and simulation methods. Three inclusions of rutin/beta-cyclodextrin (β-CD), rutin/2-hydroxypropyl beta-cyclodextrin (HP-β-CD) and rutin/2,6-dimethyl beta-cyclodextrin (DM-β-CD) were prepared by the freeze-drying method, and the inclusions were analyzed using Fourier infrared spectroscopy (FTIR), X-ray diffraction analysis (XRD), differential scanning calorimetry (DSC) and ultraviolet–visible spectroscopy (UV) to characterize and demonstrate the formation of the inclusion complexes. Phase solubility studies showed that rutin formed a 1:1 stoichiometric inclusion complex and significantly increased its solubility. β-CD, HP-β-CD, DM-β-CD, rutin and the three inclusion complexes were modeled by using MS2018 and AutoDock 4.0, and molecular dynamics simulations were performed to calculate the solubility parameters, binding energies, mean square displacement (MSD), hydrogen bonding and radial distribution functions (RDF) after the equilibration of the systems. The results of simulation and experiment showed that rutin/DM-β-CD had the best encapsulation effect among the three cyclodextrin inclusion complexes.https://www.mdpi.com/1420-3049/28/3/955rutincyclodextrincomplexmolecular dockingmolecular dynamics simulation |
| spellingShingle | Chaokang Chang Meng Song Mingxing Ma Jihong Song Fengyi Cao Qi Qin Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion Complexes Molecules rutin cyclodextrin complex molecular docking molecular dynamics simulation |
| title | Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion Complexes |
| title_full | Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion Complexes |
| title_fullStr | Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion Complexes |
| title_full_unstemmed | Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion Complexes |
| title_short | Preparation, Characterization and Molecular Dynamics Simulation of Rutin–Cyclodextrin Inclusion Complexes |
| title_sort | preparation characterization and molecular dynamics simulation of rutin cyclodextrin inclusion complexes |
| topic | rutin cyclodextrin complex molecular docking molecular dynamics simulation |
| url | https://www.mdpi.com/1420-3049/28/3/955 |
| work_keys_str_mv | AT chaokangchang preparationcharacterizationandmoleculardynamicssimulationofrutincyclodextrininclusioncomplexes AT mengsong preparationcharacterizationandmoleculardynamicssimulationofrutincyclodextrininclusioncomplexes AT mingxingma preparationcharacterizationandmoleculardynamicssimulationofrutincyclodextrininclusioncomplexes AT jihongsong preparationcharacterizationandmoleculardynamicssimulationofrutincyclodextrininclusioncomplexes AT fengyicao preparationcharacterizationandmoleculardynamicssimulationofrutincyclodextrininclusioncomplexes AT qiqin preparationcharacterizationandmoleculardynamicssimulationofrutincyclodextrininclusioncomplexes |