Host-guest Inclusion Research Articles

Supramolecular engineering of cell membrane vesicles for cancer immunotherapy

The clinical translation of nanomedicines has been strongly hampered by the limitations of delivery vehicles, promoting scientists to search for novel nanocarriers. Although cell membrane-based delivery systems have attracted extensive attention, further functionalizations are urgently desired to augment their theranostic functions. We propose a cell-friendly supramolecular strategy to engineer cell membranes utilizing cyclodextrin-based host–guest molecular recognitions to fix the defects arising from chemical and genetic modifications. In this study, the supramolecular cell membrane vesicles (SCMVs) specifically accumulate in tumors, benefiting from tumor-homing capability and the enhanced permeability and retention effect. SCMVs co-delivering indocyanine green and an indoleamine 2,3-dioxygenase inhibitor effectively ablate tumors combining photodynamic therapy and immunotherapy. Driven by host–guest inclusion complexation, SCMVs successfully encapsulate resiquimod to repolarize tumor-associated macrophages into M1 phenotype, synergizing with immune checkpoint blockade therapy. This supramolecular engineering methodology based on noncovalent interactions presents a generalizable and cell-friendly tactic to develop living cell–originated nanomaterials for precise cancer therapy.

Hyaluronic Acid-Enwrapped Polyoxometalate Complex for Synergistic Near Infrared-II Photothermal/Chemo-Therapy and Chemodynamic Therapy.

To enhance the efficacy of tumor therapy, the collection of functional components into a targeting system shows advantages over most homogeneous materials in inducing apoptosis of cancer cells. The security and targeting of therapeutic agents also require the effect combination of additional components. However, the construction of multifunctional composites in a simple system with intelligent cooperative responsiveness remains a challenge. Herein, a reduced polyanionic cluster (rP2W18) bearing the absorption at the near infrared (NIR) II region is used as a core carrier to bind the positively charged doxorubicin hydrochloride (DOX) through ionic interaction. To reduce the physiological toxicity, hyaluronic acid grafting β-cyclodextrin side chains is used to cover the ionic complex through host-guest inclusion to DOX. When the nanocomposite is activated by local laser exposure, the final three-component therapeutic agent is demonstrated to present targeted photothermal conversion capability and chemodynamic activity together with chemotherapy. With the controlled release of DOX under the stimulation of mild acidity in the tumor region and photothermal effect, the exposed rP2W18 is aroused by hydrogen peroxide overexpressed in a tumor microenvironment to produce toxic reactive oxygen species, 1O2. This work presents an opportunity for the development of a nanocomposite in NIR-II photothermal/chemo-therapy and chemodynamic synergistic therapy.

Color‐tunable room temperature phosphorescence mediated by host–guest chemistry and stimuli‐responsive polymer matrices

AbstractColor‐tunable room temperature phosphorescence (RTP) luminescent materials with stimuli‐responsive properties are highly desirable for practical applications, but the fundamental design principles still need further exploitation. Herein, we report on the extended red‐shifted multicolor RTP afterglow from blue to orange, including white light, offered by a series of newly designed supramolecular polymers based on 1‐([2‐methylallyl]oxy)pyrene phosphor‐containing guest polymers and β‐cyclodextrin (β‐CD)/γ‐CD host molecules. RTP enhancement is efficiently realized, attributing to the strong restriction on the dimeric pyrene units by the host–guest inclusion complexation of CDs and the multiple interactions amongst polymer matrices and phosphorescent moieties. Interestingly, a more comprehensive blue‐shifted color tuning range is also enabled upon introducing pH‐sensitive fragments due to the self‐assembly of the ternary polymers aided by ionic bonding. Notably, optimized intelligent multicolor RTP systems induced by altered external stimuli, including concentration, irradiation, and pH, are established, showing great potential in developing stimuli‐responsive luminescent materials for practical applications. In addition, theoretical calculations are conducted to elucidate diverse emission mechanisms of pyrene units in different assembly states.

Functional supramolecular micelles driven by the amphiphilic complex of biotin-acyclic cucurbituril and cannabidiol for cell-targeted drug delivery

Precise delivery of hydrophobic drugs has always been a great challenge for drug delivery systems. To overcome this problem, we designed and synthesized a novel supramolecular host biotin-acyclic cucurbituril (ACBB) at the first time, and we have developed a host–guest amphiphilic complex based on ACBB and amantadine-conjugated cannabinoids (AD-CBD) that self-assembles to form functionalized supramolecular micelles (FSMs) for cell-targeted drug delivery. The 1:1 stoichiometric ratio of the amphiphilic complex and its possible host–guest inclusion behaviors are obtained by fluorescence titration, nuclear magnetic resonance (NMR), Fourier transform-infrared spectroscopy (FT-IR) and thermal analysis (TGA and DSC). Using transmission electron microscope (TEM) and dynamic light scattering (DLS), we have observed that the shape of FSMs was spherical and size was 137–192 nm. In addition, MTT test results show that FSMs have good antitumor activity, taking MCF-7 as an example, the in vitro half-maximal inhibitory concentration (IC50) values of FSMs were 1.53 μM and 5.02 μM, which were better than 30.83 μM of cisplatin. Confocal laser scanning microscopy (CLSM) results showed that FSMs loaded with Rhodamine B can specifically aggregate on the surface of tumor cells and the targeting ability has been directly verified. Flow cytometry results showed that FSMs could promote tumor cell apoptosis. All results indicated that FSMs had high bioavailability, stability, accurate targeting and excellent delivery efficiency, which had great application potential in the field of drug delivery.

Enhanced Antioxidant, Antiviral, and Anticancer Activities of the Extract of Fermented Egyptian Rice Bran Complexed with Hydroxypropyl-β-cyclodextrin.

Egyptian rice bran was fermented with baker’s yeast, and released phenolics were extracted with aqueous methanol to give fermented rice bran extract (FRBE). The analysis of the FRBE with ultra-performance liquid chromatography–electrospray ionization–tandem mass spectrometry revealed 21 compounds, mainly phenolic acids and flavonoids. The FRBE was then complexed with (2-hydroxypropyl)-β-cyclodextrin (HPβCD) via noncovalent host–guest inclusion complexation using the thin-film hydration technique to improve the hydrophilicity and bioactivity of the FRBE. The formation of the inclusion complex was confirmed using HPLC, 1H NMR, FT-IR, and a phase solubility study. In addition, the biological activities of the complex were investigated. The FRBE/HPβCD inclusion complex had more pronounced antioxidant, antiviral, and anticancer activities compared to free FRBE. These findings warrant the future investigation of potential medical applications of FRBE.

A β-Cyclodextrin-Albumin Conjugate for Enhancing Therapeutic Efficacy of Cytotoxic Drugs.

Enhancing the selectivity of anticancer drugs currently used in the clinic is of great interest in order to propose more efficient chemotherapies with fewer side effects for patients. In this context, we developed a β-cyclodextrin trimer that binds to circulating albumin to form the corresponding bioconjugate in the bloodstream. This latter can then entrap doxorubicin following its i.v. administration via the formation of a host-guest inclusion complex and deliver the drug in tumors. In this study, we demonstrate that the β-cyclodextrin trimer improves the therapeutic efficacy of doxorubicin for the treatment of a subcutaneous murine Lewis lung carcinoma (LLC) implanted in C57BL/6 mice. This outcome is associated with an increased deposition of doxorubicin in malignant tissues when used in combination with the β-cyclodextrin trimer compared to the administration of the drug alone.

Theoretical Studies on the Role of Guest in α-CL-20/Guest Crystals

The contradiction between energy and safety of explosives is better balanced by the host–guest inclusion strategy. To deeply analyze the role of small guest molecules in the host–guest system, we first investigated the intermolecular contacts of host and guest molecules through Hirshfeld surfaces, 2-D fingerprint plots and electrostatic interaction energy. We then examined the strength and nature of the intermolecular interactions between CL-20 and various small molecules in detail, using state-of-the-art quantum chemistry calculations and elaborate wavefunction analyses. Finally, we studied the effect of the small molecules on the properties of CL-20, using density functional theory (DFT). The results showed that the spatial arrangement of host and guest molecules and the interaction between host and guest molecules, such as repulsion or attraction, may depend on the properties of the guest molecules, such as polarity, oxidation, hydrogen content, etc. The insertion of H2O2, H2O, N2O, and CO2 had significant influence on the electrostatic potential (ESP), van der Waals (vdW) potential and chemical bonding of CL-20. The intermolecular interactions, electric density and crystal orbital Hamilton population (COHP) clarified and quantified the stabilization effect of different small molecules on CL-20. The insertion of the guest molecules improved the stability of CL-20 to different extents, of which H2O2 worked best.

Host-guest inclusion complexes of hydroxytyrosol with cyclodextrins: Development of a potential functional ingredient for food application.

Hydroxytyrosol (HT), a potent phenolic phytochemical, exerts positive health effects due to its antioxidant properties. However, it is highly reactive to oxygen, light, and heat and presents high instability. Alpha- and beta-cyclodextrin (α-CD, β-CD) have structures that allow them to encapsulate a variety of hydrophobic molecules. The aim of this study was to examine the outcomes of the inclusion of HT into α-CD and β-CD. Aqueous solutions of HT and either α-CD or β-CD were prepared and freeze-drying was applied for the encapsulation, in 1:1 and 2:1 molar ratios. The produced solid complexes were studied and characterized using NMR spectroscopy, differential scanning calorimetry (DSC) and attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR). Encapsulation efficiency (EE%), stability, and in vitro release of the encapsulated complexes under simulated digestion conditions were also evaluated. In both DSC thermograms and FTIR spectra of the inclusion complexes, absence of the characteristic peaks of HT and shifts of the CDs peaks were observed, showing an interaction between the molecules. NMR suggested a stronger complex formed between β-CD and HT. The EE% of β-CD/HT (1:1 and 2:1) complexes and α-CD/HT (1:1) complex was found to be higher (83%, 76%, 78%, respectively), compared to α-CD/HT (2:1) (51%). Data obtained support the encapsulation of HT in both CDs, revealing a potential interaction between them and an improvement in HT's thermal stability. Regarding the in vitro release study, both CD complexes had similar behavior and a controlled release of HT in the intestinal site was observed. PRACTICAL APPLICATION: The encapsulation of hydroxytyrosol in cyclodextrins resulted in white amorphous food-grade powders with no aroma and taste. Incorporation of these powders in foods could lead to an increase in their antioxidant content and offer an additional nutritional value.

Discrete, Cationic Palladium(II)-Oxo Clusters via f-Metal Ion Incorporation and their Macrocyclic Host-Guest Interactions with Sulfonatocalixarenes.

We report on the discovery of the first two examples of cationic palladium(II)‐oxo clusters (POCs) containing f‐metal ions, [PdII 6O12M8{(CH3)2AsO2}16(H2O)8]4+ (M=CeIV, ThIV), and their physicochemical characterization in the solid state, in solution and in the gas phase. The molecular structure of the two novel POCs comprises an octahedral {Pd6O12}12− core that is capped by eight MIV ions, resulting in a cationic, cubic assembly {Pd6O12MIV 8}20+, which is coordinated by a total of 16 terminal dimethylarsinate and eight water ligands, resulting in the mixed PdII‐CeIV/ThIV oxo‐clusters [PdII 6O12M8{(CH3)2AsO2}16(H2O)8]4+ (M=Ce, Pd6Ce8 ; Th, Pd6Th8 ). We have also studied the formation of host‐guest inclusion complexes of Pd6Ce8 and Pd6Th8 with anionic 4‐sulfocalix[n]arenes (n=4, 6, 8), resulting in the first examples of discrete, enthalpically‐driven supramolecular assemblies between large metal‐oxo clusters and calixarene‐based macrocycles. The POCs were also found to be useful as pre‐catalysts for electrocatalytic CO2‐reduction and HCOOH‐oxidation.

Host-Guest Inclusion Complexes of Natural Products and Nanosystems: Applications in the Development of Repellents.

Repellents are compounds that prevent direct contact between the hosts and the arthropods that are vectors of diseases. Several studies have described the repellent activities of natural compounds obtained from essential oils. In addition, these chemical constituents have been pointed out as alternatives to conventional synthetic repellents due to their interesting residual protection and low toxicity to the environment. However, these compounds have been reported with short shelf life, in part, due to their volatile nature. Nanoencapsulation provides protection, stability, conservation, and controlled release for several compounds. Here, we review the most commonly used polymeric/lipid nanosystems applied in the encapsulation of small organic molecules obtained from essential oils that possess repellent activity, and we also explore the theoretical aspects related to the intermolecular interactions, thermal stability, and controlled release of the nanoencapsulated bioactive compounds.

Michler's Ketone: β-Cyclodextrin Host-Guest Inclusion Complex for Enhancing the Ultraviolet Protection Factor of Poplin Cotton Fabric.

Michler's ketone (4,4' bis(N,N-dimethylamino)benzophenone) mk is a potential ultraviolet radiation (UVR) absorber in various materials. In this study, we have tested the UVR filtering ability of mk on cotton fabric. The beta-cyclodextrin (β-CD) inclusion complex of mk enhances ultraviolet protection factor (UPF) drastically. The impact of β-CD on the UVR filtering of mk are demonstrated by investigating the guest (mk:absorbers)-host (β-CD:enhancer) inclusion complex. Spectral and molecular docking analysis of mk:β-CD complex infers the vertical insertion of the guest molecule by positioning -C=O group of mk at the center of the host molecule with the exclusion of the terminal atoms of guest molecule outside the β-CD cavity. Thus, the host; β-CD renders an inflexible fit to the guest:mk. The inflexible fit of mk into the β-CD cavity enhances the UVR dissipation when it is incorporated on the poplin cotton fabric. With UPF = 46 mk:β-CD complex is proposed as a potential UVR absorber suitable for manufacturing sun protective textiles. The holding of mk by β-CD enhances the UVR dissipation and hence facilitates the native red-shifted emission and non-radiative relaxation by the formation of twisted intramolecular charge transfer in mk.

From normal crosslinking to core–shell structure: Improved performance of β-cyclodextrin based adsorbent toward efficient separation of acetophenone and 1-phenylethanol

To efficiently separate acetophenone (AP) and 1-phenyethanol (PE) from petrochemical by-product, we herein report a novel feasible strategy to fabricate β-cyclodextrin (β-CD) based core–shell microsphere, which retains the cage-type crystal structure of β-CD and superior affinity to AP over PE. Using triphenylmethane-4,4′,4′'-triisocyanate (TTI) as monomer, the polymeric TTI shell can grow in-situ on the surface of β-CD particles, giving the core–shell structured CD@PTTI. The unique β-CD core and polymeric TTI shell structure was verified by a series of characterization methods. CD@PTTI-3 exhibits both high AP uptake (ca. 2.07 mmol·g−1) and AP/PE selectivity (ca. 7.2), outperforming the conventional TTI cross-linked amorphous β-CD polymer (TTI-CDP). The adsorption behavior of CD@PTTI-3 on AP and PE single-component solutions was investigated by batch adsorption experiments. Based on the experimental and theoretical results, a mechanism of competitive adsorption of AP and PE on CD@PTTI-3 involving host–guest inclusion, hydrogen bonding and π-π stacking is proposed. Furthermore, intense competition between AP and PE on CD@PTTI-3 was observed in column breakthrough experiments, and CD@PTTI-3 could purify AP from 77.16% to 93.6% by a single adsorption–desorption process.

Cyclodextrin-Based Nanosponges: Overview and Opportunities.

Nanosponges are solid cross-linked polymeric nano-sized porous structures. This broad concept involves, among others, metal organic frameworks and hydrogels. The focus of this manuscript is on cyclodextrin-based nanosponges. Cyclodextrins are cyclic oligomers of glucose derived from starch. The combined external hydrophilicity with the internal hydrophobic surface constitute a unique “microenvironment”, that confers cyclodextrins the peculiar ability to form inclusion host‒guest complexes with many hydrophobic substances. These complexes may impart beneficial modifications of the properties of guest molecules such as solubility enhancement and stabilization of labile guests. These properties complemented with the possibility of using different crosslinkers and high polymeric surface, make these sponges highly suitable for a large range of applications. Despite that, in the last 2 decades, cyclodextrin-based nanosponges have been developed for pharmaceutical and biomedical applications, taking advantage of the nontoxicity of cyclodextrins towards humans. This paper provides a critical and timely compilation of the contributions involving cyclodextrins nanosponges for those areas, but also paves the way for other important applications, including water and soil remediation and catalysis.

Concurrent elimination and stepwise recovery of Pb(II) and bisphenol A from water using β–cyclodextrin modified magnetic cellulose: adsorption performance and mechanism investigation

Coexistence of heavy metals and endocrine disrupting compounds in polluted water with competitive adsorption behavior necessitates design of tailored adsorbents. In this work, β-cyclodextrin modified magnetic rice husk-derived cellulose (β-CD@MRHC) which can provide independent functional sites for effectively binding the above two types of contaminants was synthesized and used for Pb(II) and BPA elimination in both unit and multivariate systems. Characterizations results confirmed successful β-CD grafting and Fe3O4 loading, and the β-CD@MRHC had excellent magnetic property for its effectively recovery from water, which was not affected by the adsorption of pollutants. The β-CD@MRHC possessed superior adsorption performance with maximal Pb(II)/BPA uptake of 266.2 or 412.8 mg/g, severally, and the adsorption equilibrium was fleetly reached in 30 and 7.5 min. Moreover, the β-CD@MRHC could accomplish synergetic Pb(II) and BPA elimination through averting their competitive behaviors owing to diverse capture mechanisms for Pb(II) (ion exchange, complexation and electrostatic attraction) and BPA (hydrogen bonding and host-guest inclusion). Furthermore, after three cycles of step-wise desorption, the binding of Pb(II) as well as BPA byβ-CD@MRHC dropped slightly in dualistic condition. In summary, β-CD@MRHC was a promising tailored adsorbent to practical application for simultaneously removing heavy metals and organic matters from wastewater with high-performance magnetic recovery.

Host‐Fueled Transient Supramolecular Hydrogels

AbstractInspired by the dissipative assembly in biological systems, transient hydrogels based on supramolecular interactions have been developed that are under thermodynamic nonequilibrium states. Host–guest interactions possess excellent properties including high selectivity and adjustable association constants, which are beneficial for controlling the properties and behaviors of transient colloidal materials. In this work, a host‐fueled transient supramolecular hydrogel system is reported. The hydrogels based on host–guest interactions are formed by addition of a chemical fuel, α‐cyclodextrin (α‐CD), to the aqueous solutions containing Pluronic F127 and α‐amylase. Meanwhile, as the host molecule of α‐CD consumes, the hydrogel networks start to collapse. The lifetime of the transient supramolecular hydrogels can be precisely controlled by adjusting the temperature and hydrogel composition, and repeated sol‐to‐gel‐to‐sol transitions can be realized by refueling the system with α‐CD. This study provides a new approach to regulate the nonequilibrium host–guest inclusion system by fueling it with host molecules.

Mini Review on Synthesis and Characterization Methods for Ternary Inclusion Complexes of Cyclodextrins with Drugs

Drug dependence and tolerance has become a major issue related to human health and significantly affects people living in the world today. Cyclodextrins (CDs), a family of cyclic oligosaccharides, have been widely used in the field of pharmaceutical sciences to formulate host-guest inclusion complexes with desired pharmaceutical drugs in order to improve their bioavailability and absorption by the human body. To further enhance the properties of CD-drug binary inclusion complexes, the formulation of ternary CD-drug inclusion complexes with an additive (for example polymers, organic acids, amino acids, and co-solvents) as the ternary component have been vastly explored by researchers worldwide. This review article offers a brief but comprehensive overview on various applicable synthesis and characterization methods employed by researchers for the formulation of ternary inclusion complexes of cyclodextrins with pharmaceutical drugs.

Host-guest inclusion complexes of sulfabenzamide with β- and methyl-β-cyclodextrins: Characterization, antioxidant activity and DFT calculation

The inclusion complexation behavior, characterization and binding ability of sulfabenzamide (SBZ) with β-cyclodextrin (β-CD) and methyl-β-cyclodextrin (Mβ-CD) have been investigated both in solution and solid state by different experimental techniques. Sulfabenzamide drug having poor water solubility and slow dissolution. In order to improve its water solubility and thus dissolution, cyclodextrin complexation technique was followed. The spectral shifts revealed that part of aniline ring of SBZ is entrapped in the CD cavity. The association constants were determined by Benesi-Hildebrand plots and spectroscopic studies. The phase solubility studies were carried using two different types of cyclodextrins viz., β, methyl-β cyclodextrins. The phase solubility profiles with all the two cyclodextrins were classified as AL-type, indicating the formation of 1:1 stoichiometric inclusion complexes. Inclusion complexes exhibited higher rates of dissolution than the corresponding physical mixtures and pure drug. Characterization of inclusion complexes was done by solubility studies, in vitro dissolution studies, FTIR, 1HNMR, XRD and SEM studies. We investigated the interaction of the host–guest Mβ-CD/SBZ complex by means of molecular dynamics simulation using a density functional based tight-binding code (DFT).

Supramolecular Complexes of Plant Neurotoxin Veratridine with Cyclodextrins and Their Antidote-like Effect on Neuro-2a Cell Viability.

Veratridine (VTD) is a plant neurotoxin that acts by blocking the voltage-gated sodium channels (VGSC) of cell membranes. Symptoms of VTD intoxication include intense nausea, hypotension, arrhythmia, and loss of consciousness. The treatment for the intoxication is mainly focused on treating the symptoms, meaning there is no specific antidote against VTD. In this pursuit, we were interested in studying the molecular interactions of VTD with cyclodextrins (CDs). CDs are supramolecular macrocycles with the ability to form host–guest inclusion complexes (ICs) inside their hydrophobic cavity. Since VTD is a lipid-soluble alkaloid, we hypothesized that it could form stable inclusion complexes with different types of CDs, resulting in changes to its physicochemical properties. In this investigation, we studied the interaction of VTD with β-CD, γ-CD and sulfobutyl ether β-CD (SBCD) by isothermal titration calorimetry (ITC) and nuclear magnetic resonance (NMR) spectroscopy. Docking and molecular dynamics studies confirmed the most stable configuration for the inclusion complexes. Finally, with an interest in understanding the effects of the VTD/CD molecular interactions, we performed cell-based assays (CBAs) on Neuro-2a cells. Our findings reveal that the use of different amounts of CDs has an antidote-like concentration-dependent effect on the cells, significantly increasing cell viability and thus opening opportunities for novel research on applications of CDs and VTD.

β-Cyclodextrin functionalized magnetic nanoparticles for the removal of pharmaceutical residues in drinking water

Trace amounts of pharmaceuticals and personal care products (PPCPs) are found in our water systems, and they are known to have adverse effects on wildlife and human at the ng/L to μg/L range, below the detection limit of most water analytical instruments. Methacrylate acid (MAA)-ethyl acrylate (EA) colloidal scaffolds were prepared via emulsion polymerization and used as templates for the in-situ co-precipitation of Fe2+ to produce stable functional magnetic nanoparticles (MNPs) (<500 nm) decorated with β-cyclodextrin (β-CD) (FMNP). Emulsion polymerization with the controlled addition of monomer mixtures allowed for good size control, and silica coating was introduced to prevent the oxidation of FMNP. The superparamagnetic FMNP with high saturation magnetization (33 emu/g) could be readily separated from water using a high gradient magnetic separator (HGMS). Procaine hydrochloride (PrHy) was used as a model pharmaceutical residue to evaluate the performance of the FMNP, and 53.65 mg PrHy/g FMNP was absorbed using 600 ppm FMNP. A fast (30 min) adsorption kinetic follows the Pseudo-first-order kinetic model that described the physical adsorption through a 1 to 1 host–guest inclusion mechanism. And the adsorption behavior followed the Freundlich isotherm with a linear adsorption performance. The proposed system is scalable and adaptable to existing water treatment processes, and it can be used for the detection of low concentration pharmaceuticals via a pre-concentrating strategy.

Adsorption Properties and Host-guest Effects of Porous Cyclodextrin Polymers for Dye Molecules in Water

Cyclodextrin can form host-guest inclusion complexes with a variety of organic pollutants and has unique advantages in removing complex dye molecules from water. In this study, a porous cyclodextrin polymer (P-CDP) was prepared using a rigid crosslinking agent, and the structure of the P-CDP was characterized by FT-IR, XPS, SEM, BET, and other technologies. The P-CDP was studied using isothermal adsorption and kinetic adsorption experiments. The inclusion adsorption performance and host-guest effect of the P-CDP for dye molecules in water were studied using competitive experiments. The characterization results showed that the P-CDP had strong thermal stability. It had a microporous structure with a specific surface area of 108.745 m2·g-1. The Langmuir model and the pseudo-second-order kinetic model had a higher fitting degree for the adsorption process. The results of the competition experiments showed that the electrostatic effect was stronger than the host-guest effect in the adsorption process. Pollutants whose molecular configurations were highly matched with the cyclodextrin cavity could form inclusion complexes with high molecular stability. Contaminants with strong hydrophobicity were more likely to be encapsulated in the cyclodextrin cavity. After the P-CDP adsorbed the dyes, the removal efficiency after the fifth cycle of elution and regeneration remained above 80%. This study showed that P-CDP has potential application value in the treatment of dye wastewater.