Encapsulation Mechanism of Oxyresveratrol by β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin and Computational Analysis

Abstract

In this study, the encapsulation mechanism of oxyresveratrol and β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) was studied. As this research shows, oxyresveratrol and two cyclodextrins (CDs) were able to form inclusion complexes in a 1:1 stoichiometry. However, the interaction with HP-β-CD was more efficient, showing up as higher encapsulation constant (KF) (35,864.72 ± 3415.89 M−1). The KF values exhibited a strong dependence on temperature and pH, which decreased as they increased. From the thermodynamic parameters (ΔH0, ΔS0, and ΔG0) of the oxyresveratrol loaded β-CD (oxyresveratrol-β-CD) and HP-β-CD (oxyresveratrol-HP-β-CD), it could be seen that the complexation process was spontaneous and exothermic, and the main driving forces between oxyrsveratrol and CDs were hydrogen bonding and van der waals force. Besides, molecular docking combined with 1H-NMR were used to explain the most possible mode of interactions between oxyresveratrol and CDs.

Nepafenac-Loaded Cyclodextrin/Polymer Nanoaggregates: A New Approach to Eye Drop Formulation

“…In γCD, there are six protons: the H-3 and H-5 protons are located inside the cavity, whereas the others (H-1, H-2, H-4 and H-6) are located on the exterior of the CD molecule (Figure 6). In the case of HPβCD, there is an additional methyl group [64]. In order to confirm the formation of the inclusion complex of nepafenac with γ- and HPβ-CD, a one-dimensional 1 H NMR study was performed (see Supplementary Information, Figure S2).…”

“…As shown in Table 5, changes in Δδ for the H-3 (−0.034) and H-5 (−0.1329) proton of HPβCD were upfield, indicating the formation of an inclusion complex. Also, Δδ* of the H-5 proton was higher than Δδ* of the H-3 proton, suggesting partial inclusion of nepafenac in the HPβCD cavity [64,65].…”

Inclusion complex of clausenidin with hydroxypropyl-β-cyclodextrin: Improved physicochemical properties and anti-colon cancer activity

“…Establishment of H-bonds between host and guest molecules played a key role in stabilizing the inclusion complex. It is evident that molecular docking studies are routinely used to explain the complexation mechanism of host and guest molecules ( He et al, 2017 , Mady and Aly, 2017 , Geng et al, 2019 )…”

Risperidone/Randomly Methylated β-Cyclodextrin Inclusion Complex—Compatibility Study with Pharmaceutical Excipients

“…This particular structure of CDs confers them multiple applications in the pharmaceutical field, food, cosmetics, textile, and chemistry industry based on their property of forming guest–host inclusion complexes [ 6 , 7 , 8 , 9 , 10 ]. The inclusion complexation leads to an increase in the solubility of insoluble drug substances, including the antiviral drug remdesivir [ 11 ] to improve the chemical stability, the biological activity, and the bioavailability of guest molecules, to prevent drug–excipient or drug–drug interactions, to reduce/eliminate the unpleasant taste or odors and also ocular and gastrointestinal irritation [ 10 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. Therefore, the encapsulation of the drug in the CD cavity results in a remarkable improvement of physicochemical, biopharmaceutical properties, and therapeutic potential of the guest [ 23 , 24 , 25 ].…”