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Evaluation and Characterization of Curcumin-β-Cyclodextrin and Cyclodextrin-Based Nanosponge Inclusion Complexation.

ABSTRACT: Cyclodextrin polymers and cyclodextrin-based nanosponges have been widely investigated for increasing drug bioavailability. This study examined curcumin's complexation stability and solubilization with β-cyclodextrin and β-cyclodextrin-based nanosponge. Nanosponges were prepared through the cross-linking of β-cyclodextrin with different molar ratios of diphenyl carbonate. Phase solubility experiments were conducted to evaluate the formed complexes and evaluate the potential of using β-cyclodextrin and nanosponge in pharmaceutical formulations. Furthermore, physicochemical characterizations of the prepared complexes included PXRD, FTIR, NMR, and DSC. In addition, in vitro release studies were performed for the prepared formulations. The formation of β-cyclodextrin complexes enhanced curcumin solubility up to 2.34-fold compared to the inherent solubility, compared to a 2.95-fold increment in curcumin solubility when loaded in β-cyclodextrin-based nanosponges. Interestingly, the stability constant for curcumin nanosponges was (4972.90 M^-1), which was ten times higher than that for the β-cyclodextrin complex, where the value was 487.34 M^-1. The study results indicated a decrease in the complexation efficiency and solubilization effect with the increased cross-linker amount. This study's findings showed the potential of using cyclodextrin-based nanosponge and the importance of studying the effect of cross-linking density for the preparation of β-cyclodextrin-based nanosponges to be used for pharmaceutical formulations.

SUBMITTER: Mashaqbeh H

PROVIDER: S-EPMC8658939 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Inclusion Complexation of Organic Micropollutants with β-Cyclodextrin.

Project description:Recently, β-cyclodextrin (βCD)-based polymers with enhanced adsorption kinetics and high removal capacity of organic micropollutants (OMPs) and uptake rates have been synthesized and tested experimentally. Although the exact physical-chemical mechanisms via which these polymers capture the various types of OMPs are not yet fully understood, it is suggested that the inclusion complex formation of OMPs with βCD is very important. In this study, the inclusion complex formation of OMPs with βCD in an aqueous solution is investigated by using the well-established attach-pull-release method in force field-based molecular dynamics simulations. A representative set of OMPs is selected based on the measured occurrences in surface and ground waters and the directives published by the European Union. To characterize the formation of the inclusion complex, the binding free energies, enthalpies, and entropies are computed and compared to experimental values. It is shown that computations using the q4md-CD/GAFF/Bind3P force field combination yield binding free energies that are in reasonable agreement with the experimental results for all OMPs studied. The binding enthalpies are decomposed into the main contributing interaction types. It is shown that, for all studied OMPs, the van der Waals interactions are favorable for the inclusion complexion and the hydrogen bond formation of the guest with the solvent and βCD plays a crucial role in the binding mechanism. Our findings show that MD simulations can adequately describe the inclusion complex formation of βCD with OMPs, which is the first step toward understanding the underlying mechanisms via which the βCD-based polymers capture OMPs.

| S-EPMC7037149 | biostudies-literature

Physicochemical Characterization and Antioxidant Activity Evaluation of Idebenone/Hydroxypropyl-β-Cyclodextrin Inclusion Complex †.

Project description:Idebenone (IDE) is an antioxidant drug active at the level of the central nervous system (CNS), whose poor water solubility limits its clinical application. An IDE/2-hydroxypropyl-β-cyclodextrin (IDE/HP-β-CD) inclusion complex was investigated by combining experimental methods and theoretical approaches. Furthermore, biological in vitro/ex vivo assays were performed. Phase solubility studies showed an AL type diagram, suggesting the presence of a 1:1 complex with high solubility. Scanning electron microscopy (SEM) allowed us to detect the morphological changes upon complexation. The intermolecular interactions stabilizing the inclusion complex were experimentally characterized by exploring the complementarity of Fourier-transform infrared spectroscopy in attenuated total reflectance geometry (FTIR-ATR) with mid-infrared light, Fourier-transform near-infrared (FT-NIR) spectroscopy, and Raman spectroscopy. From the temperature evolution of the O-H stretching band of the complex, the average enthalpy ΔHHB of the hydrogen bond scheme upon inclusion was obtained. Two-dimensional (2D) rotating frame Overhauser effect spectroscopy (ROESY) analysis and computational studies involving molecular modeling and molecular dynamics (MD) simulation demonstrated the inclusion of the quinone ring of IDE inside the CD ring. In vitro/ex vivo studies evidenced that complexation produces a protective effect of IDE against the H2O2-induced damage on human glioblastoma astrocytoma (U373) cells and increases IDE permeation through the excised bovine nasal mucosa.

| S-EPMC6843366 | biostudies-literature

Computational Insights Into the Influence of Substitution Groups on the Inclusion Complexation of β-Cyclodextrin.

Project description:Cyclodextrins (CDs) and their derivatives have good prospects in soil remediation application due to their ability to enhance the stability and solubility of low water-soluble compounds by inclusion performance. To investigate the effect of different structural properties of cyclodextrin and its derivatives on the inclusion complexation, molecular dynamic (MD) simulations were performed on the inclusion complexes formed by three kinds of CDs with polycyclic aromatic hydrocarbons (PAHs). Based on neutral β-CD, the other two CDs were modified by introducing substitutional groups, including 2-hydroxypropyl and sulfonated butyl (SBE) functional groups in the ring structure, called HP-CD and SBE-CD. MD results show that PAH can merely enter into the cavity of SBE-β-CD from its wide rim. The substitutional groups significantly affect the structure of CDs, which may also cause the flipping of the glucose units. However, the substitutional groups can also enlarge the volume of the hydrophobic cavity, resulting in a tight combination with the guest molecules.

| S-EPMC8176092 | biostudies-literature

Comprehensive Characterization of Linalool-HP-β-Cyclodextrin Inclusion Complexes.

Project description:The objective of the present study is to obtain linalool- cyclodextrin (CDs) solid complexes for possible applications in the food industry. For this purpose, a detailed study of linalool complexation was carried out at different pH values, to optimize the type of CDs and reaction medium that support the highest quantity of encapsulated linalool. Once demonstrated the ability of hydroxypropyl-β-cyclodextrin (HP-β-CDs), to form inclusion complexes with linalool (KC = 921 ± 21 L mol-1) and given their greater complexation efficacy (6.788) at neutral pH, HP-β-CDs were selected to produce solid inclusion complexes by using two different energy sources, ultrasounds and microwave irradiation, subsequently spraying the solutions obtained in the Spray Dryer. To provide scientific solidity to the experimental results, the complexes obtained were characterized by using different instrumental techniques in order to confirm the inclusion of linalool in the HP-β-CDs hydrophobic cavity. The linalool solid complexes obtained were characterized by using 1H nuclear magnetic resonance (1H-NMR) and 2D nuclear magnetic resonance (ROSEY), differential scanning calorimetry, thermogravimetry and Fourier transform infrared spectrometry. Moreover, the structure of the complex obtained were also characterized by molecular modeling.

| S-EPMC7662393 | biostudies-literature

Enhanced dissolution and stability of lansoprazole by cyclodextrin inclusion complexation: preparation, characterization, and molecular modeling.

Project description:In this study, lansoprazole (LSP)/cyclodextrin (CD) inclusion complexes were prepared using a fluid bed coating technique, with ?-cyclodextrin (?-CD) and 2-hydroxypropyl-?-cyclodextrin (HPCD) as the host molecules, respectively, to simultaneously improve the dissolution and stability of LSP. The dissolution rate and stability of LSP was dramatically enhanced by inclusion complexation regardless of CD type. LSP/HPCD inclusion complex was more stable under illumination than LSP/?-CD inclusion complex. Differential scanning calorimetry and powder X-ray diffractometry proved the absence of crystallinity in both LSP/CD inclusion complexes. Fourier transform infrared spectroscopy together with molecular modeling indicated that the benzimidazole of LSP was included in the cavity of both CDs, while LSP was more deeply included in HPCD than ?-CD. The enhanced photostability was due to the inclusion of the sulfinyl moiety into the HPCD cavity. CD inclusion complexation could improve the dissolution and stability of LSP.

| S-EPMC3513431 | biostudies-literature

Inclusion Complexation between α-Cyclodextrin and Oligo(ethylene glycol) Methyl Ether Methacrylate.

Project description:The preparation of inclusion complexes based on α-cyclodextrin (α-CD) and oligo(ethylene glycol) methyl ether methacrylate (OEGMA) was investigated aiming to reveal complexation particularities and thermodynamic and kinetic aspects as a function of the oligomer architecture. Small-angle X-ray scattering and isothermal titration calorimetry measurements revealed that oligomer molecular weight controls both the kinetics and thermodynamics of inclusion. Unlike linear ethylene glycol polymers, OEGMA groups possess a methacrylate group, which seems to act as a stopper, affecting their mode of complexation. Nuclear magnetic resonance spectra and relaxation measurements support the fact that methacrylate groups lie outside the α-CD ring and that a full sequential complexation of the oligomer ethylene oxide groups is not observed. These results allied to the temperature sensitivity of these oligomers and enable possible routes for chemical modifications and design of new stimuli-responsive materials.

| S-EPMC7191851 | biostudies-literature

Methyl-β-cyclodextrin Inclusion Complex with β-Caryophyllene: Preparation, Characterization, and Improvement of Pharmacological Activities.

Project description:β-Caryophyllene (BCP) is a sesquiterpene that shows high potential in pharmacological applications. However, these have been drastically limited by the respective volatility and poor water solubility. The present study investigates the formation of inclusion complexes between BCP and methyl-β-cyclodextrin (MβCD) and shows that these complexes promote a significant improvement of the anti-inflammatory, gastric protection, and antioxidant activities relative to neat BCP. It is shown that the solubility of BCP is significantly increased through complexation in phase solubility studies. Inclusion complexes with MβCD in solid state were prepared by three different methods, kneading, rotary evaporation, and lyophilization, with the latter confirmed by differential scanning calorimetry, Fourier transformed infrared spectroscopy, scanning electron microscopy, 1H NMR spectroscopy, and molecular dynamics studies. This study provides for the first time a full characterization of inclusion complexes between BCP and MβCD and highlights the impact of complex formation upon pharmacological activity.

| S-EPMC6044968 | biostudies-literature

Inclusion Complexes of Lycopene and β-Cyclodextrin: Preparation, Characterization, Stability and Antioxidant Activity.

Project description:In this study, the inclusion complexes of lycopene with β-cyclodextrin (β-CD) were prepared by the precipitation method. Then the inclusion complexes were characterized by the scanning electron microscopy (SEM), ultraviolet-visible spectroscopy (UV), microscopic observation, liquid chromatography, differential scanning calorimetry (DSC) and phase-solubility study. Moreover, the stability and antioxidant activity were tested. The results showed that lycopene was embedded into the cavity of β-CD with a 1:1 stoichiometry. Moreover, the thermal and irradiant stabilities of lycopene were all significantly increased by the formation of lycopene/β-CD inclusion complexes. Antioxidant properties of lycopene and its inclusion complexes were evaluated on the basis of measuring the scavenging activity for 1,1-diphenyl-2-picrylhydrazyl (DPPH), hydroxyl and superoxide anion radicals. The results showed that the scavenging activity of DPPH radicals was obviously increased by the formation of the inclusion complex with β-cyclodextrin at concentrations of 5-30 μg/mL, however, some significant positive effects on the scavenging activity of hydroxyl and superoxide anion radicals were not observed and the reasons are worth further study.

| S-EPMC6719067 | biostudies-literature

Electrospun crosslinked poly-cyclodextrin nanofibers: Highly efficient molecular filtration thru host-guest inclusion complexation.

Project description:Water pollution is a serious concern for public health and environment in today's world; hence, there exists a strong demand to develop cost-effective, sustainable and eco-friendly membranes. Here, we produce a highly efficient molecular filter membrane based on bio-renewable material; cyclic oligosaccaharides known as cyclodextrins (CD). Crosslinked insoluble poly-CD nanofibers are produced by using electrospinning technique in the absence of any additional polymeric carrier. Poly-CD nanofibrous membrane exhibit significant affinity to a common class of organic pollutant (i.e. methylene blue (MB)). Remarkably, the electrospun poly-CD nanofibrous web can outdistance the commonly used filter material (i.e. activated carbon) in terms of removal capacity. The flexible and free-standing poly-CD nanofibrous membrane depicted outstanding filtration performance. We estimate of above 90% removal efficiency for highly concentrated solutions of MB pollutant (40?mg/L) under extremely high flux (3840 Lm-2h-1). Essentially, these poly-CD nanofibrous webs demonstrate quite rapid uptake of MB from liquid environment. Overall, bio-based flexible electrospun poly-CD nanofibrous membrane represents a highly efficient molecular filter for wastewater treatment.

| S-EPMC5547107 | biostudies-other

Stability of the Inclusion Complexes of Dodecanoic Acid with α-Cyclodextrin, β-Cyclodextrin and 2-HP-β-Cyclodextrin.

Project description:In the presented work, the stability of the formation of inclusion complexes of dodecanoic acid (lauric acid) with three cyclodextrins, α-cyclodextrin, β-cyclodextrin and 2-HP-β-cyclodextrin, was analyzed from the point of view of the size of the cavity in cyclodextrins, their molar mass and the structure of the studied fatty acid. The measurements were made in a wide temperature range of 283.15-318.15K. The conductometric method was used for these studies. The results obtained allowed us to determine the value of the theoretical limiting molar conductivity (Λm0) of the studied complexes, the values of the inclusion complex formation constants (Kf) and the values of thermodynamic functions (ΔG0, ΔH0 and ΔS0) describing the complexation process in the studied temperature range.

| S-EPMC10095696 | biostudies-literature

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