[Deep eutectic solvents synergistic with carboxymethyl -ß-cyclodextrin on the improvement of chiral separation of metoprolol by capillary electrophoresis].

The physical and chemical properties of chiral drugs are very similar. However, their pharmacological and toxicological effects vary significantly. For example, one enantiomer may have favorable properties whereas the other may be ineffective or even have toxic side effects. Hence, exploring innovative strategies to improve enantiomeric resolution is of great importance. Metoprolol (MET) is a ß-receptor blocker used to treat hypertension, stable angina pectoris, and supraventricular tachyarrhythmia. Establishing chiral separation and analysis methods of MET enantiomers is important for enhancing the quality of chiral drugs. Capillary electrophoresis (CE) has the advantages of a small sample size, simple operation, high separation efficiency, and many alternative modes; therefore it is widely used in the field of chiral drug separation. The chiral selectors commonly used for CE-based chiral separation include cyclodextrin (CD) and its derivatives, polysaccharides, proteins, and macrocyclic antibiotics. CD is one of the most commonly used and effective chiral selectors for CE. The relatively hydrophobic structure inside the cavity and the relatively hydrophilic structure outside the cavity of CD enable it and chiral molecules to form inclusion compounds with different binding constants, thus achieving chiral separation. However, the use of CD alone as a chiral selector does not always yield satisfactory separation results. Hence, the addition of other additives, such as ionic liquids and deep eutectic solvents (DESs) to assist CD-based chiral separation systems has received extensive attention. Previous studies on the enantiomeric separation of MET by CE have focused on the addition of CD and its derivatives alone for separation. Few studies have been conducted on the synergistic addition of auxiliary additives to CD to improve the enantiomeric resolution of MET. In this study, three DESs, namely, choline chloride-D-glucose, choline chloride-D-fructose, and lactate-D-glucose, were used for the CE-based chiral separation of MET for the first time, and the synergistic effect of the DESs on the separation of MET enantiomers by CD-based capillary zone electrophoresis was speculated. For this purpose, an uncoated fused silica capillary with inner diameter of 50 µm, total length of 50 cm and effective length of 41.5 cm was used as the separation column. First, the effects of CD type, CD concentration, buffer pH, and buffer concentration on MET separation were investigated, and the optimal conditions (15 mmol/L carboxymethyl-ß-cyclodextrin (CM-ß-CD), pH=3.0, and 40 mmol/L phosphate buffer) were obtained. Other CE conditions were as follows: UV detection at 230 nm, applied voltage of 25 kV. All operations were carried out at 20 ℃. Next, three types of DESs were prepared as auxiliary additives via a mixed-heating method. The DESs were mixed in a 50 mL round-bottomed flask at a certain molar ratio and then heated in a water bath at 80 ℃ for 3 h until a clear and transparent liquid was obtained. The effects of different DESs and their mass fraction on chiral separation were subsequently studied. The optimal choline chloride-D-fructose mass fraction was ultimately determined to be 1.5%. The resolution of MET increased from 1.30 without DES to 2.61 with 1.5% choline chloride-D-fructose, thereby achieving baseline separation. Finally, the separation effect and mechanism were speculated. The MET chiral separation method established in this study is of great significance for improving the quality of chiral compounds and ensuring the safety and effectiveness of clinical drugs. Furthermore, it may be useful in the research and development of CE-based chiral separation techniques using CD derivatives with DESs.

Comparative Analysis of the Structure and Pharmacological Properties of Some Piperidines and Host-Guest Complexes of ß-Cyclodextrin.

Pain and anesthesia are a problem for all physicians. Scientists from different countries are constantly searching for new anesthetic agents and methods of general anesthesia. In anesthesiology, the role and importance of local anesthesia always remain topical. In the present work, a comparative analysis of the results of pharmacological studies on models of the conduction and terminal anesthesia, as well as acute toxicity studies of the inclusion complex of 1-methyl-4-ethynyl-4-hydroxypiperidine (MEP) with ß-cyclodextrin, was carried out. A virtual screening and comparative analysis of pharmacological activity were also performed on a number of the prepared piperidine derivatives and their host-guest complexes of ß-cyclodextrin to identify the structure-activity relationship. Various programs were used to study biological activity in silico. For comparative analysis of chemical and pharmacological properties, data from previous works were used. For some piperidine derivatives, new dosage forms were prepared as beta-cyclodextrin host-guest complexes. Some compounds were recognized as promising local anesthetics. Pharmacological studies have shown that KFCD-7 is more active than reference drugs in terms of local anesthetic activity and acute toxicity but is less active than host-guest complexes, based on other piperidines. This fact is in good agreement with the predicted results of biological activity.

Encapsulation of Fennel and Basil Essential Oils in ß-Cyclodextrin for Novel Biopesticide Formulation.

ß-cyclodextrin (ß-CD) is a good host for the encapsulation of fennel and basil essential oils (FEO and BEO, respectively) and the formation of inclusion complexes (ICs) using the co-precipitation method. According to the results of the GC/MS analysis conducted in this study, monoterpenes and monoterpenoids were the dominant chemical groups in total FEO, while in BEO, these two groups occurred along with sesquiterpenes and sesquiterpenoids. The presence of dominant compounds from both EOs was validated using the FT-IR spectra of ICs, which indicated successful complexation. Analyses conducted using SPME/GC-MS showed the continuous emission of volatiles over 24 h from both ICs. Under SEM, particles of both ICs appeared to have a rectangular or rhomboid morphology and few aggregates. The insecticidal properties of EOs and ICs with ß-CD were tested on the Colorado potato beetle (CPB) as a model pest. The inclusion complex of ß-CD with FEO altered the developmental dynamic and body mass of the CPB. The initial increase in the proteolytic activity of CPB larvae fed with potato plants sprayed with ICs was not maintained for long, and the proteolytic efficacy of treated larvae remained in line with that of the control larvae. Future investigations will focus on manipulating the volume of EOs used and the treatment duration for optimal efficacy and potential application.

Synthesis, characterization, molecular modeling, binding energies of ß-cyclodextrin-inclusion complexes of quercetin: Modification of photo physical behavior upon ß-CD complexation.

We prepared a naturally occurring flavanoid namely quercetin from tea leaves and analyzed by Absorption, Emission, FT-IR, 1H, 13C nmr spectra and ESI-MS analysis. The inclusion behavior of quercetin in cyclodextrins like α-, ß-, γ-, per-6-ABCD and mono-6-ABCD cavities were supported such as UV-vis., Emission, FT-IR and ICD spectra and energy minimization studies. From the absorption and emission results, the type of complexes formed were found to depend on stoichiometry of Host:Guest. FT-IR data of CD complexes of quercetin supported inclusion complex formation of the substrate with α-, ß- and γ-CDs. The inclusion of host-guest complexation of quercetin with α-, ß-, γ-CDs, per-6-ABCD and mono-6-ABCDs provides very valuable information about the CD:quercetin complexes, the study also shows that ß-CD complexation improves water solubility, chemical stability and bioavailability of quercetin. Besides, phase solubility studies also supported the formation of 1:1 drug-CD soluble complexes. All these spectral results provide insight into the binding behavior of substrate into CD cavity in the order per-6-ABCD > Mono-6-ABCD > γ-CD > ß-CD > α-CD. The proposed model also finds strong support from the fact with excess CD this exciton coupling disappears indicates the formation of only 1:1 complex.

Application of sodium sulfobutylether-ß-cyclodextrin based on encapsulation.

Sodium Sulfobutylether-ß-cyclodextrin (SBE-ß-CD) is a derivative of ß-cyclodextrin, characterized by its stereo structure, which closely resembles a truncated cone with a hydrophobic internal cavity. The solubility of insoluble substances within the hydrophobic cavity is significantly enhanced, reducing contact between the guest and the environment. Consequently, SBE-ß-CD is frequently employed as a co-solvent and stabilizer. As the research progresses, it has been observed that the inclusion of SBE-ß-CD is reversible and competitive. Besides, some inclusion complexes undergo distinct physicochemical property alterations compared to the guests. Additionally, certain guests exhibit varying inclusions with SBE-ß-CD at different concentrations. These features have contributed to the expanding applications. SBE-ß-CD finds widespread application in pharmaceutics as a protective agent and pKa regulator, in pharmaceutical analysis as a chiral substance separator, and in biomedical engineering for encapsulating dyes and modifying sensors. The article will elaborate in detail on the physicochemical properties of SBE-ß-CD, encapsulation principles, and factors influencing the formation of inclusion complexes. Furthermore, the review focuses on the application of SBE-ß-CD through encapsulation in pharmaceutics, pharmaceutical analysis, and biomedical engineering. Finally, the prospects and potential applications of SBE-ß-CD are discussed.

Influence of degree of substitution on the hydroxypropyl-ß-cyclodextrin complexation with rifampicin in water solution: a molecular simulation.

CONTEXT: Hydroxypropyl-ß-cyclodextrin (HPßCD) is one of the derivatized cyclodextrins most widely used as an excipient in the pharmaceutical industry, for its capacity to improve certain drugs properties. Different configurations of HPßCD are possible depending on the number and location of the 2-hydroxypropyl groups substituted on the glucose rings. Rifampicin has become the most commonly clinically used antibiotic against tuberculosis in recent years, despite its low solubility and variable bioavailability. Different techniques and materials have been proposed to enhance the properties of rifampicin: cyclodextrin complexation is one of them. The van der Waals term was the main contribution to the interaction energy, which then decisively conditioned the complex configurations. The size of rifampicin did not allow the whole molecule to fit into the host. Moreover, interaction energy was much greater when the guest was located near each rim of HPßCD, where rifampicin was partially included in the cavity and formed inclusion complexes. The piperazine tail of rifampicin was included inside the host in minimum energy structures and the guest was situated near the primary rim of HPßCD in most cases, although the complex configurations depended on the degree of substitution. METHODS: A molecular mechanics simulation based on the GROMOS 53A6 force field was applied in this work to study the inclusion complexes formed by twelve configurations of HPßCD, with different degrees of substitution and rifampicin in water solution. We determined the penetration potential, the complex structures with minimum energies, the possibility of forming inclusion complexes other than those of minimum energies and potential energy surfaces.

The soybean lecithin-cyclodextrin-vitamin E complex nanoparticles stabilized Pickering emulsions for the delivery of ß-carotene: Physicochemical properties and in vitro digestion.

In this work, soybean lecithin (LC) was used to modify ß-cyclodextrin (ß-CD) with hydrophobic fat chains to become amphiphilic (LC-CD), and vitamin E (VE) was encapsulated in former modified ß-CD complexes (LC-CD-VE), the new Pickering emulsions stabilized by LC-CD-VE and LC-CD complexes for the delivery of ß-carotene (BC) were created. The surface tension, contact angle, zeta potential, and particle size were used to assess the changes in complexes nanoparticles at various pH values. Furthermore, LC-CD-VE has more promise as Pickering emulsion stabilizer than LC-CD because of the smaller particle size (271.11 nm), proper contact angle (58.02°), and lower surface tension (42.49 mN/m). The interactions between ß-cyclodextrin, soybean lecithin, and vitamin E were confirmed using Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), nuclear magnetic resonance (NMR), and thermogravimetric analysis (TGA). The durability of Pickering emulsions was examined at various volume fractions of the oil phase and concentrations of nanoparticles. Compared to the emulsion stabilized by LC-CD, the one stabilized by LC-CD-VE showed superior storage stability. Moreover, for the delivery of BC, Pickering emulsions stabilized by LC-CD and LC-CD-VE can outperform bulk oil and Tween 80 stabilized emulsions in terms of UV light stability, storage stability, and bioaccessibility. This work could offer fresh perspectives on stabilizer alternatives for Pickering emulsion delivery systems.

Encapsulation of 4-terpineol with ß-cyclodextrin: Inclusion mechanism, characterization and relative humidity-triggered release.

4-Terpineol (4-TA), a typical monocyclic monoterpene essential oil compound with important biological activities, poor stability and solubility severely hamper its biological activities. To date, ß-cyclodextrin (ß-CD) encapsulating essential oil to form inclusion complexes (ICs) is considered as a satisfactory treatment. Nevertheless, the detailed inclusion mechanism of ß-CD for 4-TA especially the behavior of 4-TA during inclusion formation have not available yet. Herein, 4-TA/ß-CD ICs were successfully synthesized by the co-precipitation method, and hydrogen bonds and hydrophobic interactions played a key role in the formation of ICs, and the isopropyl of 4-TA entered the cavity through the wide rim of ß-CD. Moreover, the release profile demonstrated that high RH (85 % and 99 %) triggered the release of TA from ICs. This study suggests the great potential of cyclodextrin inclusion strategy for improving the stability and sustained release of 4-TA in food preservation application.

Neodymium adsorption from aqueous solution by ß-cyclodextrin nanosponges and a polymer valorized from potato peels waste: experiments and conventional and statistical physics interpretations.

Using organic waste and residue streams to be turned into valuable and greener materials for various applications has proven an efficient and suitable strategy. In this work, two green materials (nanosponges and a polymer) were synthesized using potato peels and applied for the first time to adsorb and recover Neodymium (Nd3+) from aqueous solutions. The recovery of Nd3+ that belongs to the rare earth elements has attracted important interest due to its/their importance in several industrial and technological applications. The fine potato peel waste (FPPW) polymer presented an irregular shape and porous surface. At the same time, the ß-cyclodextrin (ß-CD) nanosponges had uniform distribution with regular and smooth shapes. ß-CD nanosponges exhibited a much higher total carboxyl content (4.02 mmol g-1) than FPPW (2.50 mmol g-1), which could impact the Nd3+ adsorption performance because carboxyl groups can interact with cations. The adsorption capacity increased with the increase of the pH, reaching its maximum at pHs 6-7 for ß-CD nanosponges and 4-7 for FPPW polymer. The kinetic and equilibrium data were well-fitted by General order and Liu models. ß-CD nanosponges attained adsorption capacity near 100 mg Nd per gram of adsorbent. Thermodynamic and statistical physical results corroborated that the adsorption mechanism was due to electrostatic interaction/complexation and that the carboxyl groups were important in the interactions. ß-CD nanosponges (three cycles of use) were more effective than FPPW (one cycle of use) in the regeneration. Finally, ß-CD nanosponges could be considered an eco-friendly adsorbent to recover Nd3+ from aqueous matrices.

Poly-ß-cyclodextrin strengthen Pr6O11 porous oxidase mimic for dual-channel visual recognition of bioactive cysteine and Fe2.

To conveniently monitor bioactive cysteine (Cys) and Fe2+ in practice, a kind of poly-ß-cyclodextrin strengthen praseodymium oxide (Pr6O11) porous oxidase mimic (p-ß-CD@Pr6O11) was constructed by virtue of the strong coordination between nano Pr6O11 and poly-ß-cyclodextrin substrate. After its microstructure and physicochemical property were characterized in detail, it was noted that porous p-ß-CD@Pr6O11 exhibited excellent enzyme-like catalytic activity to accelerate the oxidation of 3,3',5,5,'-tetramethylbanzidine (TMB) and 2,2'-azinobis (3-ethylbenzo-thiazoline-6-sulfonic acid) ammonium salt (ABTS) with significant color-enhancement effect in the air. Based on the signal amplification, trace Cys could exclusively deteriorate the UV-vis absorbance at 653 nm of p-ß-CD@Pr6O11-TMB and Fe2+ alter the one at 729 nm of p-ß-CD@Pr6O11-ABTS with visual color changes. Under the optimized conditions, the proposed p-ß-CD@Pr6O11-TMB and p-ß-CD@Pr6O11-ABTS systems were successfully applied for dual-channel monitoring of Cys in Cys capsules and fetal bovine serum and Fe2+ in agricultural products with quite low detection limits, i.e., 7.8×10-9 mol·L-1 for Cys and 6.93×10-8 mol·L-1 (S/N=3) for Fe2+, respectively. The synergetic-enhancement detection mechanisms to Cys and Fe2+ were also proposed.

Enhanced Tumor Targeting and Antitumor Activity of Methylated ß-Cyclodextrin-Threaded Polyrotaxanes by Conjugating Cyclic RGD Peptides.

We previously reported that acid-degradable methylated ß-cyclodextrins (Me-ß-CDs)-threaded polyrotaxanes (Me-PRXs) can induce autophagic cell death through endoplasmic reticulum (ER) stress-related autophagy, even in apoptosis-resistant cells. Hence, Me-PRXs show great potential as anticancer therapeutics. In this study, peptide-supermolecule conjugates were designed to achieve the targeted delivery of Me-PRX to malignant tumors. Arg-Gly-Asp peptides are well-known binding motifs of integrin αvß3, which is overexpressed on angiogenic sites and many malignant tumors. The tumor-targeted cyclic Arg-Gly-Asp (cRGD) peptide was orthogonally post-modified to Me-PRX via click chemistry. Surface plasmon resonance (SPR) results indicated that cRGD-Me-PRX strongly binds to integrin αvß3, whereas non-targeted cyclic Arg-Ala-Glu (cRGE) peptide conjugated to Me-PRX (cRGE-Me-PRX) failed to interact with integrins αvß3. In vitro, cRGD-Me-PRX demonstrated enhanced cellular internalization and antitumor activity in 4T1 cells than that of unmodified Me-PRX and non-targeted cRGE-Me-PRX, due to its ability to recognize integrin αvß3. Furthermore, cRGD-Me-PRX accumulated effectively in tumors, leading to antitumor effects, and exhibited excellent biocompatibility and safety in vivo. Therefore, cRGD conjugation to enhance selectivity for integrin αvß3-positive cancer cells is a promising design strategy for Me-PRXs in antitumor therapy.

A Novel Magnetic ß-Cyclodextrin-Modified Graphene Oxide and Chitosan Composite as an Adsorbent for Trace Extraction of Four Bisphenol Pollutants from Environmental Water Samples and Food Samples.

In this study, a novel functionalized magnetic composite (MNCGC) for magnetic solid-phase extraction of bisphenols from environmental and food samples was developed, featuring a multistep synthesis with Fe3O4, chitosan, graphene oxide, and ß-cyclodextrin, crosslinked by glutaraldehyde. Characterization confirmed its advantageous morphology, intact crystal structure of the magnetic core, specific surface area, and magnetization, enabling efficient adsorption and separation via an external magnetic field. The optimized MSPE-HPLC-FLD method demonstrated excellent sensitivity, linearity, and recovery rates exceeding 80% for bisphenol pollutants, validating the method's effectiveness in enriching and detecting trace levels of bisphenols in complex matrices. This approach offers a new avenue for analyzing multiple bisphenol residues, with successful application to environmental water and food samples, showing high recovery rates.

Encapsulation of apigenin into ß-cyclodextrin metal-organic frameworks with high embedment efficiency and stability.

In an effort to improve the application performance of apigenin, ß-cyclodextrin metal-organic frameworks (BCDMOFs) known as porous materials were used to encapsulate apigenin via an innovative pH-adjusted method. The embedment efficiency had a significant positive pH dependence, reaching a maximum of 79.2 % ± 1.2 % at pH12. Scanning electron microscopy, X-ray diffraction, Fourier transform infrared spectroscopy, and thermogravimetric analysis demonstrated formation of apigenin/BCDMOFs composites, and exposure of BCDMOFs pores facilitated high embedment efficiency. Storage stability experiment and kinetic analysis showed degradation of apigenin/BCDMOFs composites was less than that of apigenin alone. Apigenin stability was increased by approximately 18 % after 7 days. BCDMOFs effectively encapsulated and controlled the release of apigenin, and the composites exhibited improved application performance in vitro.

Comparison of two different multiple dual-mode counter-current chromatograph for separation of ketoconazole enantiomers.

In this work, two different multiple dual-mode (MDM) counter-current chromatography methods, conventional MDM and modified MDM elution modes, were compared for the chiral separation of the ketoconazole enantiomers. The biphasic solvent system which consisted of n-hexane: isobutyl acetate: 0.1 mol/L phosphate buffer (2:4:6, v/v) (pH = 8.5) was employed as stationary phase and mobile phase. And the hydroxypropyl-ß-cyclodextrin (HP-ß-CD) with a concentration of 100 mmol/L was dissolved in the phosphate buffer, as the chiral selector. Under two different methods, dual-mode (DM) elution was performed to determine the time of the transformed phase roles and multiple cycles were performed to isolate ketoconazole, respectively. The result indicated that the modified MDM elution had a significant improvement on the separation, increasing the resolution from 0.51 to 1.19, while the resolution was increased from 0.40 to 0.79 by the conventional MDM elution. Ultimately, baseline separation of ketoconazole enantiomers was essentially achieved by high-speed counter-current chromatography under optimized modified MDM separation conditions. The final recoveries of the two enantiomers, R-(K) and S-(K), were 92.5 % and 83.3 %, respectively, corresponding to enantiomeric excess values of 99.0 % and 97.0 %, as determined by HPLC.

Supramolecular assemblies of citalopram and escitalopram in ß-cyclodextrin dimeric cavity: Crystallographic and theoretical insights.

Cyclodextrin (CD) encapsulation improves physicochemical and pharmacological properties of selective serotonin reuptake inhibitors (SSRIs), which are efficacious in treating depression, a global mental health problem. Here, we scrutinize ß-CD inclusion complexes with racemate citalopram (rac-CTP; 1) and escitalopram ((S)-CTP; 2) by combined single-crystal X-ray diffraction and DFT full-geometry optimization. X-ray analysis unveiled that the 2:2 inclusion complexes of 1 and 2 with similar inclusion modes and topologies are stabilized by various intermolecular interactions of host-guest CH···π, host-host OH···O H-bonds, and guest-guest F···F in the tail-to-tail dimeric asymmetric unit. In the crystals, these dimers are stacked on top of each other, yielding similar channel structures of distinct crystal symmetries, triclinic, P1 (1) and monoclinic, P21 (2), which are further maintained by guest-guest π···π and CN···π interactions. The thermodynamic stabilities evaluated by DFT calculation indicate the vital role of weak intermolecular interactions in the formation and stabilization of the ß-CD monomeric and dimeric inclusion complexes. This study provides crystallographic and theoretical evidence for the improved stability and the masked bitterness of CTP through ß-CD encapsulation as patented previously and suggests the pharmaceutical implications in the drug delivery and enantioseparation.

A novel cationic ß-cyclodextrin decorated with a choline-like pendant exhibits Iodophor, Mucoadhesive and bactericidal properties.

Iodine is a vital microelement and a powerful antiseptic with a rapid and broad spectrum of action. The development of iodophor compounds to improve the solubility and stability of iodine is still challenging. Here, we report the synthesis of a novel cationic ß-cyclodextrin bearing a choline-like pendant (ß-CD-Chol) designed to complex and deliver iodine to bacterial cells. The characterization of ß-CD-Chol and the investigation of the inclusion complex with iodine were performed by NMR spectroscopy, mass spectrometry, UV-vis spectrophotometry, isothermal titration calorimetry, and dynamic light scattering. The functionalization with the positively charged unit conferred improved water-solubility, mucoadhesivity, and iodine complexation efficiency to the ß-CD scaffold. The water-soluble ß-CD-Chol/iodine complex efficiently formed both in solution and by solid-vapor reaction. The solid complex exhibited a significant stability for months. Iodine release from the inclusion complex was satisfactory and the bactericidal activity was proved against a Staphylococcus epidermidis strain. The absence of cytotoxicity tested on human keratinocytes and the improved mucoadhesivity make ß-CD-Chol a promising drug delivery system and an appealing iodophor candidate for iodine-based antisepsis including mucosa disinfection.

Fabrication of magnetic Fe3O4 doped ß-cyclodextrin microporous organic network for the efficient extraction of endocrine disrupting chemicals from food takeaway boxes.

Endocrine disrupting chemicals (EDCs) are a typical class of natural or man-made endogenous hormone agonists or antagonists that can directly or potentially interfere with human endocrine system. However, it is still difficult to analyze trace EDCs directly from complex environment and food matrices. Therefore, the proper sample pretreatment is highly desired and the preparation of efficient adsorbents is of great challenge and importance. Herein, we report the facile one-pot solvothermal synthesis of Fe3O4 nanoparticle doped magnetic ß-cyclodextrin microporous organic network composites (MCD-MONs) for the magnetic solid phase extraction (MSPE) of four phenolic EDCs in water and food takeaway boxes prior to the high-performance liquid chromatography analysis. The sheet-like Fe3O4 doped MCD-MONs offered good magnetic property (16.5 emu g-1) and stability, and provided numerous hydrogen bonding, hydrophobic, π-π, and host-guest interaction sites for EDCs. Under the optimal experimental conditions, the established method was successfully verified with wide linear range (2.0-1000 µg L-1), low limits of detection (0.6-1.0 µg L-1), good precisions (intra-day and inter-day RSDs < 5.2 %, n = 3), large enrichment factors (88-98) and adsorption capacity (90.3-255.8 mg g-1), short extraction time (6 min), less adsorbent consumption (3 mg), and good reusability (at least 8 times) for EDCs. The proposed method was successfully applied to detect the trace EDCs in real samples with the recovery of 84.0-99.7 %. This work demonstrated the great potential of MCD-MONs for the efficient MSPE of trace EDCs from complex food takeaway boxes and water samples and uncovered the prospect of CD-based MONs in sample pretreatment.

Fluorescence and pectinase double-triggered chitosan/pectin/calcium propionate/curcumin-ß-cyclodextrin complex film for pork freshness monitoring and maintenance.

An intelligent and active food packaging film based on chitosan (CS), pectin (P), calcium propionate (CP), and curcumin-ß-cyclodextrin complex (Cur-ß-CD) was prepared. The CS/P/CP/Cur-ß-CD film exhibited improved hydrophobicity (74.78 ± 0.53°), water vapor (4.55 ± 0.16 × 10-11 g·(m·s·Pa)-1), and oxygen (1.50 ± 0.06 × 10-12 g·(m·s·Pa)-1) barrier properties, as well as antioxidant (72.34 ± 3.79 % for DPPH and 86.05 ± 0.14 % for ABTS) and antibacterial (79.41 ± 2.89 % for E. coli and 83.82 ± 3.96 % for S. aureus) activities. The release of CP and Cur could be triggered by pectinase, with their cumulative release reaching 92.62 ± 1.20 % and 42.24 ± 1.15 %, respectively. The CS/P/CP/Cur-ß-CD film showed delayed alterations in surface color, pH value, total volatile bases nitrogen, total viable counts, thiobarbituric acid reactive substance, hardness, and springiness of pork. Additionally, the fluorescence intensity of the film gradually decreased. In conclusion, we have developed a pH-responsive film with pectinase-triggered release function, providing a new concept for the design of multi-signal responsive intelligent food packaging.

ß-Cyclodextrin based Pickering emulsions for α-tocopherol delivery: Antioxidation stability and bioaccessibility.

ß-Cyclodextrin (ß-CD) Pickering emulsion and cinnamaldehyde/ß-cyclodextrin (CIN/ß-CD) Pickering emulsion were prepared and the influences of oxidation and digestion were investigated. CIN/ß-CD composite was better dispersed at the oil-water interface than ß-CD. Hydrophobic group of CIN anchored in the oil phase and Hydrophilic hydroxyl group of ß-CD extended into the aqueous phase, which allowed CIN/ß-CD composite to be oriented at the oil-water interface and formed a more stable oil-water interface layer. ß-CD Pickering emulsion was more susceptible to oxidative deterioration than CIN/ß-CD Pickering emulsion, its malondialdehyde (MDA) value was as high as 509.41 ± 9.37 nmol/L. Digestion experiment indicated that CIN/ß-CD Pickering emulsion was released inner oil phase in the small intestine and free fatty acid (FFA) release rate was 44.32 ± 1.08%. Pharmacokinetic parameters manifested that α-tocopherol peak concentration (Cmax) was 64.32 ± 6.45 mg/L and the peak time (Tmax) appeared at 5 h after administration of CIN/ß-CD Pickering emulsion.

Rigid crosslink improves the surface area and porosity of ß-cyclodextrin beads for enhanced adsorption of flavonoids.

Many reported ß-cyclodextrin (ß-CD) polymers have poor flavonoid adsorption performance due to their low surface area and porosity resulting from the compact stack of the ß-CD molecules crosslinked by flexible crosslinkers. Here, we propose a rigid crosslink strategy that uses phytic acid (PA) having rigid cyclic group as crosslinkers, achieving a high-surface-area (61.42-140.23 m2/g) and porous ß-CD beads. The improved surface area and porosity are attributed to the rigid cyclic groups in PA, which expand the network structure of ß-CD polymers. Benefitting from the advantages, the optimized PA-crosslinked ß-CD (PA-ß-CD) beads have an over tenfold increased adsorption amount and an threefold increased diffusivity for rutin compared with traditional non-porous ß-CD beads crosslinked by epichlorohydrin. Moreover, dynamic adsorption experiments reveal that PA-ß-CD beads are able to treat about 1100 mL of rutin solution (0.05 mg/mL), over 5 times higher than that of the non-porous ß-CD beads (200 mL). These results demonstrate the promise of PA-ß-CD beads for rapid and high-capacity adsorption of rutin.