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The fluorescent probe provides a simple for detecting Cu2+ through fluorescence quenching of the Schiff‐base probes by Cu2+. However, the azine‐based probes often suffer from poor solubility and dispersibility in water and are easily interfered with by other competing ions, which significantly reduces their applicable potential. In this study, we synthesized a water‐dissoluble and highly fluorescent γ‐Cyclodextrin (γ‐CD)/2‐hydroxybenzaldehyde azine (2‐HBA) inclusion complex for Cu2+ detection. The inclusion of 2‐HBA into γ‐CD enhances its solubility in water and allows it to emit fluorescence. The as‐synthesized γ‐CD/2‐HBA probe exhibits high sensitivity for colorimetric and fluorescent detection of Cu2+, with detection limits reaching 2.72 and 1.53 nM, respectively. The results exceed most of those reported in the literature. The probe's structure and potential mechanism were systematically analysed using the experimental and theoretical methods. [ABSTRACT FROM AUTHOR]

BACKGROUND: Papaya, a highly nutritious and economically significant fruit, is susceptible to infections caused by phytopathogenic fungi. Cinnamon essential oil, derived from Cinnamomum cassia (CC), shows promise in preserving papaya due to its antifungal properties. However, CC is volatile, sensitive to environmental factors, and carries a strong aroma. γ‐Cyclodextrin (γ‐CD) is known for encapsulating hydrophilic molecules, shielding them from environmental influences, reducing odor, and enabling controlled release due to its unique channel structure. This study aimed to tackle these challenges by preparing and characterizing an inclusion complex of CC with γ‐CD (CC‐γ‐CD), and subsequently evaluating its efficacy in preserving papaya fruits. RESULTS: Analyses, including Fourier‐infrared, powder X‐ray diffraction, thermal gravity analysis, differential scanning calorimeter, and scanning electron microscopy, revealed successful encapsulation of CC components within the γ‐CD cavity. Evaluations of the CC‐γ‐CD complex's impact on papaya fruit shelf life and quality showed notable enhancements. Fruits treated with CC‐γ‐CD inclusion complex at a dose of 10 g kg−1 exhibited a 55% extension in shelf‐life, evidenced by reduced disease severity index compared with untreated fruit in the same storage conditions. Detailed physicochemical and bromatological assessments highlighted significant improvements, particularly in fruit treated with CC‐γ‐CD inclusion complex at a dose of 10 g kg−1. CONCLUSION: The application of CC‐γ‐CD inclusion complex at 10 g kg−1 extended the shelf‐life of papaya fruit, significantly and markedly improved the overall quality. These findings underscore the potential of the CC‐γ‐CD inclusion complex as an effective preservative for papaya, offering a promising solution for its postharvest management and marketability. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Glaucoma is the leading cause of blindness worldwide. However, its surgical treatment, in particular via trabeculectomy, can be complicated by fibrosis. In current clinical practice, application of the drug, Mitomycin C, prevents or delays fibrosis, but can lead to additional side effects, such as bleb leakage and hypotony. Previous in silico drug screening and in vitro testing has identified the known antibiotic, josamycin, as a possible alternative antifibrotic medication with potentially fewer side effects. However, a suitable ocular delivery mechanism for the hydrophobic drug to the surgical site does not yet exist. Therefore, the focus of this paper is the development of an implantable drug delivery system for sustained delivery of josamycin after glaucoma surgery based on crosslinked γ-cyclodextrin. γ-Cyclodextrin is a commonly used solubilizer which was shown to complex with josamycin, drastically increasing the drug’s solubility in aqueous solutions. A simple γ-cyclodextrin crosslinking method produced biocompatible hydrogels well-suited for implantation. The crosslinked γ − cyclodextrin retained the ability to form complexes with josamycin, resulting in a 4-fold higher drug loading efficiency when compared to linear dextran hydrogels, and prolonged drug release over 4 days.

It is well known that platinum-based antineoplastic agents, including cisplatin (CP), have side effects that limit their use. Nefrotoxicity, neurotoxicity, and hemolytic anemia are the most common side effects. There are few studies on the reduction in these effects that involves nanoencapsulation; however, almost none involve cyclodextrins (CDs). Changes in the hematological and biochemical parameters of healthy Wistar rats treated with solutions of γ-cyclodextrin/resveratrol/cisplatin (γ-CD/Rv/CP) ternary complexes are investigated for the first time. They are intraperitoneally injected with γ-CD/Rv/CP solutions containing 5 mg CP/kg.b.w. Single shots were administered to six groups of Wistar rats (six individuals for every group) using γ-CD/Rv/CP, γ-CD/CP, γ-CD/Rv complexes, as well as positive- and negative-control groups, respectively. Thirty-two hematological and biochemical parameters were evaluated from blood samples and used as input variables for the principal component analysis (PCA) discrimination of the groups. The best protection was obtained for the γ-CD/Rv/CP ternary complex, which determined closer biochemical values to the control group. These values significantly differ from those of the γ-CD/CP treated group, especially for the IP, UA, and T-Pro kidney-related biochemical parameters. This finding proves the beneficial influence of Rv during CP administration through CD-based carriers. [ABSTRACT FROM AUTHOR]

Dairy protein hydrolysates possess a broad spectrum of bioactivity and hypoallergenic properties, as well as pronounced bitter taste. The bitterness is reduced by complexing the proteolysis products with cyclodextrins (CDs), and it is also important to study the bioactivity of the peptides in inclusion complexes. Hydrolysates of whey and colostrum proteins with extensive hydrolysis degree and their complexes with β/γ-CD were obtained in the present study, and comprehensive comparative analysis of the experimental samples was performed. The interaction of CD with peptides was confirmed via different methods. Bioactivity of the initial hydrolysates and their complexes were evaluated. Antioxidant activity (AOA) was determined by fluorescence reduction of fluorescein in the Fenton system. Antigenic properties were studied by competitive enzyme immunoassay. Antimutagenic effect was estimated in the Ames test. According to the experimental data, a 2.17/2.78-fold and 1.45/2.14-fold increase in the AOA was found in the β/γ-CD interaction with whey and colostrum hydrolysates, respectively. A 5.6/5.3-fold decrease in the antigenicity of whey peptides in complex with β/γ-CD was detected, while the antimutagenic effect in the host–guest systems was comparable to the initial hydrolysates. Thus, bioactive CD complexes with dairy peptides were obtained. Complexes are applicable as a component of specialized foods (sports, diet). [ABSTRACT FROM AUTHOR]

Room-temperature phosphorescence and organic afterglow materials exhibit significant applications in diverse fields. Among them, aqueous-phase organic afterglow materials display interesting biomedical and other applications, whereas afterglow material fabrication in aqueous medium remains less explored when compared to those in solid states. In view of the excellent afterglow performance in difluoroboron β-diketonate containing systems, here we report supramolecular inclusion complexation of γ-cyclodextrin (γCD) with difluoroboron β-diketonate (BF2bdk) phosphors for devising aqueous-phase room-temperature afterglow crystalline micro/nanostructures. The γCD-BF2bdk host-guest supramolecular interactions induce crystallization of the two-component system into micro/nanostructures where BF2bdk’s triplet excited states can be well protected from nonradiative decay and oxygen quenching, leading to the emergence of aqueous-phase afterglow with phosphorescence lifetimes around 1 s and high photoluminescence quantum yields (PLQY) > 50 %. The aqueous afterglow materials possess visible-light-excitable property and can serve as donor of energy transfer for constructing long-wavelength and color-tunable afterglow systems. Their potential applications for bioimaging were further demonstrated. The present study provides a simple method but a new avenue for the preparation of high-performance aqueous-phase afterglow materials.

A kind of epitope surface imprinted particles was synthesized to selectively recognize cytochrome c (Cyt c) by a novel strategy assisted with γ-cyclodextrin (γ-CD) by host-guest interaction. C-terminal epitope nonapeptide of Cyt c was chosen as the template. γ-CD was immobilized on the surface of the silica as an encapsulated molecule to capture the template and improve the corresponding spatial orientation by the host-guest interaction for the peptide and target protein recognition. After γ-CD and epitope modified, the surface imprinted polymer assisted with the host-guest interaction was synthesized via monomers and cross-linkers by radical polymerization strategy. After the peptide removal, the epitope surface imprinted particles were obtained. The performance of Cyt c recognition in bovine serum sample by the imprinted polymers was calculated by HPLC. The modified imprinted polymers prepared achieved the best binding capability of 2.89 mg g−1 AE-9 with the IF = 4.07 and 37.58 mg g−1 Cyt c with the IF = 3.38, and it also realized an efficiency and selectivity protein recognition. Additionally, the imprinted particles assisting by γ-CD have good reusability with 89.89% of the original after five sorption-elution cycles and a better recognized ability (IF = 3.38) than those without γ-CD assisting (IF = 1.44). These results indicated that this epitope imprinted method assisted with the host-guest recognition interaction by γ-CD exhibited well specific recognition abilities towards the target protein Cyt c and potential application for Cyt c recognition in biological sample. [ABSTRACT FROM AUTHOR]

Enantioselective labeling of important bioactive molecules in complex biological environments by artificial receptors has drawn great interest. From both the slight difference of enantiomers' physicochemical properties and inherently complexity in living organism point of view, it is still a contemporary challenge for preparing practical chiral device that could be employed in the model animal due to diverse biological interference. Herein, we introduce γ-cyclodextrin onto graphene oxide for fabricating γ-cyclodextrin and graphene oxide assemblies, which provided an efficient nanoplatform for chiral labelling of D-phenylalanine with higher chiral discrimination ratio of KD/KL = 8.21. Significantly, the chiral fluorescence quenching effect of this γ-CD-GO nanoplatform for D-phenylalanine enantiomer in zebrafish was 7.0-fold higher than L-isomer, which exhibiting real promise for producing practical enantio-differentiating graphene-based systems in a complex biological sample. [ABSTRACT FROM AUTHOR]

Drug solubility plays a significant role in the development of drug formulation. The objectives of this work are to improve the solubility and dissolution rate of vortioxetine (VT) by preparing its inclusion complexes (ICs) with β‐Cyclodextrin (β‐CD) and γ‐Cyclodextrin (γ‐CD). The ICs were prepared in 1:1 M ratio via recrystallization method and characterized by P‐XRD, FT‐IR, 1H NMR, 2D NOESY, and DSC. Further, the crystal structure of VT‐β‐CD was analyzed by SC‐XRD. P‐XRD data obtained for ICs describe the crystalline pattern. The DSC analysis shows change in the thermal behavior of VT, CDs and ICs. FT‐IR analysis shows shifting of frequencies in ICs when compared with the pristine VT drug and CDs. The 2D NOESY in DMSO‐d6 indicates weak interaction between the VT and CD molecules. The crystal structure of VT‐β‐CD consists of one guest VT, one host CD, and nine water molecules in the crystal lattice. The solubility of ICs was significantly improved in distilled water, pH 1.2 acidic, and phosphate buffer pH 6.8 medium, as compared with the solubility of the pristine VT drug. The in vitro dissolution rate of ICs in different dissolution media was investigated, which was higher than that of the commercial product of VT. [ABSTRACT FROM AUTHOR]

BACKGROUND: Epigallocatechin‐3‐gallate (EGCG) is well known for excellent chain‐breaking antioxidant capability. However, browning by oxidation and aggregation of EGCG is a non‐negligible defect that hinders its applications as an antioxidant in various foodstuffs. Therefore, how to eliminate or mitigate browning efficiently, while retaining functionalities as food additive is a challenge in the food industry. RESULTS: Our results demonstrated that EGCG could be anchored within the internal cavity of γ‐cyclodextrin (γ‐CD) to form an inclusion structure, where hydrophobic interaction, hydrogen bonding, and π‐stacking were identified to be the primary drivers. The interplay between two molecules and the steric hindrance from γ‐CD could restrict the motion and aggregation of EGCG efficiently, thus alleviating the browning effect. In addition, the conformational adaption of EGCG within the inclusions would result in general decreases in hydrogen‐bond dissociation enthalpies for the pyrogallol‐type structure on the b ring, thus enhancing the antioxidant capability. In practical application, the nanoscale γ‐CD/EGCG inclusion complexes were validated preliminarily as efficient additives in the preservation of shrimp surimi, presenting significant effects on prolonging the shelf‐life of products. CONCLUSION: Here, nanoscale γ‐CD/EGCG inclusion complexes as alternatives to EGCG were tailored as food antioxidants for the preservation of shrimp surimi products, exerting antioxidant effects while mitigating the browning effects of EGCG on products. Through self‐assembly, EGCG would be anchored with the cavity of γ‐CD, which could regulate the release modes and restrict the aggregation of EGCG. This facile strategy has great potential in food preservation. © 2023 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

A three-component inclusion complex of ascorbyl palmitate (ASCP), urea (UR), and γ-cyclodextrin (γCD) with a molar ratio of 1/12 has been prepared for the first time using the evaporation method (EVP method) and the grinding and mixing method (GM method). Also, we investigated changes in the physicochemical properties of the three-component complexes. The powder X-ray diffraction (PXRD) measurements showed ASCP, UR, and γCD characteristic peaks in the physical mixture (PM) (AU (ASCP/UR = 1/12)/γCD = 1/2). In GM (AU (ASCP/UR = 1/12)/γCD = 1/1), new diffraction peaks were observed around 2θ = 7.5° and 16.6°, while characteristic peaks derived from EVP (ASCP/UR = 1/12) were observed at 2θ = 23.4° and 24.9°. On the other hand, new diffraction peaks at 2θ = 7.4° and 16.6° were observed in GM (1/2). In the differential scanning calorimeter (DSC) measurement, an endothermic peak at around 83 °C was observed in the GM (1/1) sample, which is thought to originate from the phase transition of urea from the hexagonal to the tetragonal form. An endothermic peak around 113.9 °C was also observed for EVP (ASCP/UR = 1/12). However, no characteristic phase transition-derived peak or EVP (ASCP/UR = 1/12)-derived endothermic peak was observed in GM (1/2). Near infrared (NIR) spectroscopy of GM (1/2) showed no shift in the peak derived from the CH group of ASCP. The peaks derived from the NH group of UR shifted to the high and low wavenumber sides at 5032 cm−1 and 5108 cm−1 in EVP (ASCP/UR = 1/12). The peak derived from the OH group of γCD shifted, and the peak derived from the OH group of ASCP broadened at GM (1/2). These results suggest that AU (ASCP/UR = 1/12)/γCD prepared by the mixed grinding method formed inclusion complexes at the molar ratio (1/2). [ABSTRACT FROM AUTHOR]

Abscisic acid (2‐cis,4‐trans‐abscisic acid) is a plant hormone that has an asymmetric carbon atom. We tried to separate the enantiomers of native abscisic acid by HPLC using a phenyl column and a chiral mobile phase containing γ‐cyclodextrin. The optimum mobile phase conditions were found to be 0.8% (w/v) γ‐cyclodextrin, 4% (v/v) acetonitrile, and 20 mM phosphate buffer (pH 6.0). It was found that (R)‐abscisic acid was earlier detected than (S)‐abscisic acid. Since γ‐cyclodextrin is hardly retained on a phenyl column, it was suggested that (R)‐abscisic acid formed a more stable complex with γ‐cyclodextrin than the (S)‐abscisic acid. Abscisic acid in an acacia honey sample was successfully enantioseparated with the proposed method and only (S)‐abscisic acid was detected. A biologically inactive 2‐trans,4‐trans‐abscisic acid, which was prepared by irradiation of abscisic acid with a light‐emitting diode lamp at 365 nm, was partially enantioseparated by the proposed method. Since the irradiation of (S)‐abscisic acid‐induced cis‐to‐trans isomerization to produce one 2‐trans,4‐trans‐abscisic acid enantiomer, it is reasonable that racemization did not proceed during the cis‐to‐trans isomerization. (S)‐Abscisic acid and probably (S)‐2‐trans,4‐trans‐abscisic acid were detected in a honey sample, where the peak area of (S)‐abscisic acid was 7 times larger than that of (S)‐2‐trans,4‐trans‐abscisic acid. [ABSTRACT FROM AUTHOR]

Host–guest assemblies open up opportunities for developing novel functional CLUSPOM multicomponent systems based on transition metal clusters (CLUS), polyoxometalates (POMs) and macrocyclic organic ligands. In water–ethanol solution γ-cyclodextrin (γ-CD) interacts with halide metal clusters [M6Cl14]2– (M = Mo, W) to form sandwich-type structures. The supramolecular association between the clusters and CDs, however, remains weak in solution, and the interactions are not strong enough to prevent the hydrolysis of the inorganic guest. Although analysis of the resulting crystal structures reveals inclusion complexation, 1H NMR experiments in solution show no specific affinity between the two components. The luminescent properties of the host–guest compounds in comparison with the initial cluster complexes are also studied to evaluate the influence of CD. [ABSTRACT FROM AUTHOR]

Overproduction of reactive oxygen species is one of the important reasons of non-healing wounds, such as diabetic wounds. Melatonin is well known as an antioxidant, while the poor solubility limits its use in many areas. In this study, the solubility of melatonin was improved by introducing γ-cyclodextrin to form the composite named MT-γ-CD through ultrasonic process. During this process, the molar ratio of melatonin and γ-cyclodextrin was 2:1, the temperature was set at 30 ℃, and the ultrasonic time was 40 min. The MT-γ-CD showed good antioxidant property in vitro with high free radical scavenging efficiency over 90%. Besides, an injectable self-healing hydrogel was prepared to load with MT-γ-CD to form the wound dressing, here, sodium carboxymethylated cellulose was oxidized to introduce aldehyde groups that could form Schiff base with amino groups in gelatin. This dressing with good biocompatibility could be injected into irregular wounds, suppress the level of reactive oxygen species, and accelerate wound healing of diabetic rats in vivo. Therefore, it has great potential to provide a new treatment strategy for diabetic wounds. [ABSTRACT FROM AUTHOR]

Rifampicin is a potent antimicrobial drug with some suboptimal properties, such as poor stability, low solubility, and variable bioavailability. Therefore, in the current study, a multicomponent complex between rifampicin, γ-cyclodextrin, and arginine was prepared with the aim of improving drug properties. Solubility was evaluated by phase-solubility studies. The mechanism of interaction was established through proton nuclear magnetic resonance spectroscopy and molecular modeling. Physicochemical characterization was investigated using Fourier transform-infrared spectroscopy, powder X-ray diffraction, and scanning electron microscopy. The dissolution properties, antimicrobial activity (antibacterial, antibiofilm, and antileishmanial), and stability of the different samples were studied. The results obtained in this investigation demonstrate that multicomponent complexes can improve the water solubility and dissolution rate of rifampicin, as well as its antibacterial and antileishmanial action, and present suitable stability. In conclusion, rifampicin complexed with γ-cyclodextrin and arginine is an attractive approach for developing pharmaceutical dosage forms of rifampicin with increased antimicrobial activities. [ABSTRACT FROM AUTHOR]

Metal-organic frameworks based on cyclodextrins (CDs) have been proposed as promising drug delivery systems due to their large surface area, variable pore size, and biocompatibility. In the current work, we investigated an incorporation of tolfenamic acid (TA), a representative of non-steroidal anti-inflammatory drugs (NSAIDs), in a metal-organic framework based on γ-cyclodextrin and potassium cations (γCD-MOF). Composites γCD-MOF/TA obtained by absorption and co-crystallization methods were characterized using powder X-ray diffraction, low temperature nitrogen adsorption/desorption, scanning electron microscopy, and FTIR spectroscopy. It was demonstrated that TA loaded in γCD-MOF has an improved dissolution profile. However, the inclusion of TA in γ-CD reduces the membrane permeability of the drug. A comparative analysis of the encapsulation of different NSAIDs in γCD-MOF was performed. The impact of NSAID structure on the loading capacity was considered for the first time. It was revealed that the presence of heterocycles in the structure and drug lipophilicity influence the loading efficiency of NSAIDs in γCD-MOF. [ABSTRACT FROM AUTHOR]

[Display omitted] Tilmicosin, as an effective broad-spectrum antibacterial drug, has incomplete absorption and low bioavailability due to its low water solubility, which limits its veterinary clinical applications. As a non-polymeric drug carrier, γ -cyclodextrin was complexed with tilmicosin through supercritical carbon dioxide assistance for the first time, and confirmed by FTIR, X-ray diffraction, proton NMR and scanning electron microscopy. The water solubility of tilmicosin was increased 57-fold through complexation with γ -cyclodextrin, and the release and bioavailability of tilmicosin in the complex were significantly improved. The tilmicosin in complex showed better anti- Streptococcus agalactiae activity than that of tilmicosin alone in MIC, MBC and drug susceptibility studies. [ABSTRACT FROM AUTHOR]

Green mold caused by Penicillium digitatum is one of the most destructive postharvest diseases in citrus fruit. Chemical fungicides (such as prochloraz) can be expected to effectively control this disease. But the widespread use of chemicals can easily lead to drug resistance of the pathogen, environmental pollution and food safety risks. Previous studies have shown that the plant essential oils and their bioactive components can be served as a type of potential biofungicide, due to the effective reduction of the postharvest disease in citrus fruit without impairing the fruit quality. However, the scale application can be largely limited by the volatility and easily oxidized property. Fortunately, the inclusion of cyclodextrins can be expected to improve the effectiveness of plant essential oils. In this study, the saturated aqueous solution was used to prepare the inclusion complexes of trans-2-hexenal, an active component in plant essential oils, particularly with four kinds of cyclodextrins including α-cyclodextrin (α-CD), β-cyclodextrin (β-CD), γ-cyclodextrin (γ-CD), and hydroxypropyl-β-cyclodextrin (HP-β-CD). An effort was also made to improve the antifungal efficiency of trans-2-hexenal. At the same time, the antifungal activity of these inclusion complexes against P. digitatum was analyzed by in vitro assay, in order to determine the structure and the inclusion mode of the inclusion complex with the highest efficiency. As a result, four inclusion compounds designated as α-CDTH, β-CDTH, γ-CDTH, and HP-β-CDTH, respectively, were prepared by the saturated aqueous solution. The morphological results showed that the α-CDTH, β-CDTH, and γ-CDTH powders were fine and dense, while the HP-β-CDTH powder was rough with distinct particles. The in vitro antifungal data demonstrated that these inclusion compounds were used to effectively inhibit the growth of P. digitatum mycelium in a concentration-dependent manner. The minimum antifungal concentration (MFC) of β-CDTH and γ-CDTH to the mycelial growth of P. digitatum was estimated to be both 1.00 mg/mL, while the MFCs of α-CDTH and HP-β-CDTH were 2.00 and 4.00 mg/mL, respectively. The entrapment efficiency indicated that the highest entrapment efficiency (75.36%) was found in the γ-CDTH, whereas the HP-β-CDTH was the lowest entrapment efficiency (38.63%). The AL type was used to describe the phase solubility curves of the four cyclodextrin inclusion compounds. The solubility was also ranked in the descending order of HP-β-CD>γ-CD>β-CD>α-CD. The best overall performance was found in the γ-CDTH considering the in vitro antifungal efficiency, entrapment efficiency, and solubility. Thus, the γ-CDTH was selected as the material for the follow-up experiments. In vivo assay showed that the γ-CDTH at different concentrations reduced the incidence of green mold in citrus fruit at varying degrees (P<0.05), with 8.00 g/L γ-CDTH as the most effective concentration. Once the control fruits were totally rotten after 6 d storage, the disease incidence in the samples of 8.00 g/L γ-CDTH treatment was only 58.3 %, which was comparable to that of prochloraz (56.7 %). In addition, the γ-CDTH treatment effectively maintained the citrus fruit firmness without any adverse effects on the weight loss rate, color, vitamin C, and total soluble solids contents of citrus fruit. The Scanning Electron Microscopy (SEM) observation revealed that the shapes and sizes of γ-CDTH were quite different from those of γ-CD and physical mixtures, the varying sizes and irregular crystals were found in γ-CD. In contrast, the physical mixtures presented a rough surface, whereas the γ-CDTH was a smooth surface with a flake-like morphology. The nuclear magnetic resonance (NMR) analysis demonstrated that the hydrogen bonding interactions between H-3ʹ and H-5ʹ of γ-CD and H-6 of trans-2-hexenal were attributed to the formation of γ-CDTH. In summary, four inclusion compounds of trans-2-hexenal with cyclodextrins were prepared to further verify the antifungal efficiency and structural characteristics of γ-CDTH. The findings can provide a direct basis for the γ-CDTH to control citrus postharvest diseases in the development of plant-derived natural preservatives. [ABSTRACT FROM AUTHOR]

• Folic acid surface-modified CD-MOF nanoplatform was constructed for quercetin delivery (Qu@FA-CMOF). • Modification of FA enabled Qu@FA-CMOF to specifically deliver quercetin to injured gastric cells. • Qu@FA-CMOF nanoplatform effectively exerted antioxidant, anti-inflammatory, and anti-apoptotic effects in vitro and vivo. • Potential mechanism of Qu@FA-CMOF in alleviating gastric ulcer was by regulating Nrf2, COX-2/NF-κB, and Bax/Bcl-2 pathways. Gastric ulcers, often caused by factors such as ethanol consumption and Helicobacter pylori infection, present significant treatment challenges due to the limited efficacy and adverse effects of current therapies. This study aimed to develop a nanoscale quercetin (Qu) delivery system using folic acid (FA)-functionalized cyclodextrin-based metal–organic frameworks (CD-MOFs), termed Qu@FA-CMOF nanoplatforms, to enhance therapeutic outcomes for acute gastric ulcers. The FA modification endowed the nanoplatforms with targeted delivery capabilities, improving cellular uptake and facilitating the sustained release of Qu. Comprehensive in vitro and in vivo evaluations demonstrated that Qu@FA-CMOF significantly attenuated gastric tissue injury, reduced oxidative stress, and suppressed inflammation by modulating the Nrf2/HO-1 and COX-2/NF-κB signaling pathways. Furthermore, the nanoplatform exhibited potent anti-apoptotic effects through regulation of the Bax/Bcl-2 pathway, and showed favorable biocompatibility with no significant toxicity observed in major organs. These findings highlight the potential of Qu@FA-CMOF nanoplatforms as a safe and effective therapeutic strategy for ethanol-induced gastric injury, offering a promising avenue for future nanomedicine-based therapies in gastric ulcer treatment. [ABSTRACT FROM AUTHOR]

It is well known that platinum-based antineoplastic agents, including cisplatin (CP), have side effects that limit their use. Nefrotoxicity, neurotoxicity, and hemolytic anemia are the most common side effects. There are few studies on the reduction in these effects that involves nanoencapsulation; however, almost none involve cyclodextrins (CDs). Changes in the hematological and biochemical parameters of healthy Wistar rats treated with solutions of γ-cyclodextrin/resveratrol/cisplatin (γ-CD/Rv/CP) ternary complexes are investigated for the first time. They are intraperitoneally injected with γ-CD/Rv/CP solutions containing 5 mg CP/kg.b.w. Single shots were administered to six groups of Wistar rats (six individuals for every group) using γ-CD/Rv/CP, γ-CD/CP, γ-CD/Rv complexes, as well as positive- and negative-control groups, respectively. Thirty-two hematological and biochemical parameters were evaluated from blood samples and used as input variables for the principal component analysis (PCA) discrimination of the groups. The best protection was obtained for the γ-CD/Rv/CP ternary complex, which determined closer biochemical values to the control group. These values significantly differ from those of the γ-CD/CP treated group, especially for the IP, UA, and T-Pro kidney-related biochemical parameters. This finding proves the beneficial influence of Rv during CP administration through CD-based carriers.

Dairy protein hydrolysates possess a broad spectrum of bioactivity and hypoallergenic properties, as well as pronounced bitter taste. The bitterness is reduced by complexing the proteolysis products with cyclodextrins (CDs), and it is also important to study the bioactivity of the peptides in inclusion complexes. Hydrolysates of whey and colostrum proteins with extensive hydrolysis degree and their complexes with β/γ-CD were obtained in the present study, and comprehensive comparative analysis of the experimental samples was performed. The interaction of CD with peptides was confirmed via different methods. Bioactivity of the initial hydrolysates and their complexes were evaluated. Antioxidant activity (AOA) was determined by fluorescence reduction of fluorescein in the Fenton system. Antigenic properties were studied by competitive enzyme immunoassay. Antimutagenic effect was estimated in the Ames test. According to the experimental data, a 2.17/2.78-fold and 1.45/2.14-fold increase in the AOA was found in the β/γ-CD interaction with whey and colostrum hydrolysates, respectively. A 5.6/5.3-fold decrease in the antigenicity of whey peptides in complex with β/γ-CD was detected, while the antimutagenic effect in the host–guest systems was comparable to the initial hydrolysates. Thus, bioactive CD complexes with dairy peptides were obtained. Complexes are applicable as a component of specialized foods (sports, diet).

This study aimed to produce freeze-dried inclusion complex of cinnamon essential oil (CEO) using β-cyclodextrin (BCD) and γ-cyclodextrin (GCD) as wall materials in two selected weight ratios (85/15 and 80/20). Encapsulation efficiency (EE) of CEO was significantly higher when the CD/CEO ratio was maintained at 80/20. Additionally, the GCD exhibited an excellent EE (96.5%) than the BCD (71.02%). Various analytical techniques, including Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry, X-ray diffraction, scanning electron microscopy, and rheological measurements demonstrated that the CEO was efficiently encapsulated in the cavity of cyclodextrins. Rheological data of CD and CEO in solution were fitted to the Herschel-Bulkley and Cross model well. The antimicrobial activity of the inclusion complexs (ICs) displayed that the CEO in GCD (80/20) had the excellent inhibitory effect against Listeria monocytogenes, and Salmonella enterica sv Typhimurium. Overall, the GCD acts as a superior wall material by forming an excellent IC with CEO with desirable properties. The obtained results demonstrated that both encapsulates would have potential for use as intermediate materials in antimicrobial food packaging. [ABSTRACT FROM AUTHOR]

The solid-phase exchange of ethanol in γ-cyclodextrin inclusion compounds has afforded binding of volatile organic compounds not forming inclusion compounds with dry γ-cyclodextrin or its hydrates. The obtained results can be used in the development of efficient filters to remove aromatic compounds from air. [ABSTRACT FROM AUTHOR]

BACKGROUND: Quercetin (Que) has many pharmacological activities, such as anticancer, antioxidant, cardiovascular protection, antihypertensive and lipid‐lowering activities. However, its poor water solubility greatly limits its application in medicine and food. γ‐Cyclodextrin metal–organic frameworks (γ‐CD‐MOFs) are novel porous carriers for loading functional products. In this study, Que was successfully loaded into γ‐CD‐MOFs, and the new compound (Que‐CD‐MOFs) was characterised by X‐ray diffraction, infrared spectroscopy, thermogravimetric analysis and scanning electron microscopy. RESULTS: The apparent solubility of Que‐CD‐MOFs was enhanced by 100‐fold compared with that of pure Que. The free radical scavenging ability of the encapsulated Que was significantly improved. The cytotoxicity of Que‐CD‐MOFs to HK‐2 cells was decreased, and their inhibition on HT‐29 tumour cells was maintained, as confirmed by CCK‐8 assays. Flow cytometry of HT‐29 cells showed that Que‐CD‐MOFs can inhibit G2 phase cells. Based on molecular modelling, Que molecules were preferentially located inside the cavities of γ‐CD pairs in γ‐CD‐MOFs. CONCLUSION: γ‐CD‐MOFs are promising carriers for bioactive agents in food and pharmaceutical applications. © 2021 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

The clinical use of anticancer drugs necessitates new technologies for their safe, sensitive, and selective detection. In this article, lanthanide (Eu3+ and Tb3+)-loaded γ-cyclodextrin nano-aggregates (ECA and TCA) are reported, which sensitively detects the anticancer drug irinotecan by fluorescence intensity changes. Fluorescent lanthanide (Eu3+ and Tb3+) complexes exhibit high fluorescence intensity, narrow and distinct emission bands, long fluorescence lifetime, and insensitivity to photobleaching. However, these lanthanide (Eu3+ and Tb3+) complexes are essentially hydrophobic, toxic, and non-biocompatible. Lanthanide (Eu3+ and Tb3+) complexes were loaded into naturally hydrophilic γ-cyclodextrin to form fluorescent nano-aggregates. The biological nontoxicity and cytocompatibility of ECA and TCA fluorescent nanoparticles were demonstrated by cytotoxicity experiments. The ECA and TCA fluorescence nanosensors can detect irinotecan selectively and sensitively through the change of fluorescence intensity, with detection limits of 6.80 μM and 2.89 μM, respectively. ECA can safely detect irinotecan in the cellular environment, while TCA can detect irinotecan intracellularly and is suitable for cell labeling. [ABSTRACT FROM AUTHOR]

The present work aimed to encapsulate the thyme essential oil (TEO) in β-cyclodextrin (BCD) and γ-cyclodextrin (GCD) complexes in two selected cyclodextrin (CD) to TEO ratios (85/15 and 80/20 w/w) and compare the physicochemical, antioxidant, and antimicrobial properties of the encapsulated powders. The inclusion complexes between CD and TEO were prepared by blending aqueous CD and TEO in ethanol followed by freeze-drying. The powder properties were assessed by measuring particle size and microstructure using SEM, FTIR, and XRD. The median values of the particle sizes (GCD: 92.0 ± 4.69 and BCD: 46.2 ± 2.56-mm) significantly influenced the encapsulation efficiency, resulting in a higher encapsulation efficiency of the GCD (92.02 ± 10.79%) than that of the BCD (56.30 ± 12.19%). The encapsulated GCD/TEO (80/20) showed higher antioxidant activity and an antimicrobial inhibitory effect against Listeria monocytogenes and Salmonella enterica sv. typhimurium. Overall, the GCD acts as a superior wall material to the BCD in the TEO encapsulation. [ABSTRACT FROM AUTHOR]

γ-Cyclodextrin (γ-CD) is a cyclic oligosaccharide composed of eight glucose molecules linked together via α-1,4-glycosidic bonds. It has a wide range of applications in the pharmaceutical, food, and chemical industries. Two pathways were designed for the synthesis of γ-CD from the non-food feedstock cellulose via an in vitro adenosine triphosphate (ATP) –free synthetic enzymatic biosystem. Cellulose was employed as the substrate for producing cellobiose, which was subsequently converted to γ-CD via a cascade reaction utilizing five enzymes. A stoichiometric conversion of cellulose to γ-CD was achieved by adding the synthesis module for glucose-1-phosphate (G-1-P) and optimizing the reaction conditions. The productivity of γ-CD obtained via pathway II – condition III was as high as 517 g/m3·h from cellobiose, representing a 16-fold increase compared to pathway II – condition I. A process for producing γ-CD from cellulose was established in this study, which yielded γ-CD of >90 % purity. This study presents a novel process that could be employed in next-generation biorefineries and a strategy for improving the economic considerations associated with cellulose utilization. [Display omitted] [ABSTRACT FROM AUTHOR]

Chronic kidney disease entails a progressive decline in kidney function, hindering the kidneys' ability to excrete fluid, electrolytes, and metabolites. This dysfunction leads to metabolite accumulation in the bloodstream, which can reach toxic concentrations. Hemodialysis is an effective means of treating patients with kidney failure, but it does not clear all toxins effectively. Engineered nano-adsorbents can potentially improve the removal of retained toxins, particularly protein-bound types. Magnetic nanoparticles coated with α-, β-, and γ-cyclodextrin were synthesized, and physicochemical properties were characterized using thermogravimetric analysis, transmission electron microscopy, dynamic light scattering, and ζ-potential for their physiochemical properties. The effect of surface chemistry and incubation time on toxin adsorption was investigated using quantitative mass spectrometry techniques. All particle types demonstrated toxin adsorption to some level. Overall, the adsorption process was independent of metabolite concentration, suggesting a dynamic interplay between surface properties and solution composition. This insight will contribute to developing innovative adsorbent films designed to remove uremic toxins effectively. [ABSTRACT FROM AUTHOR]

γ-Cyclodextrin (γ-CD) is an attractive material among the natural cyclodextrins owing to its excellent properties. γ-CD is primarily produced from starch by γ-cyclodextrin glycosyltransferase (γ-CGTase) in a controlled system. However, difficulty in separation and low conversion rate leads to high production costs for γ-CD. In this study, γ-CGTase from Bacillus sp. G-825-6 STB17 was used in γ-CD production from cassava starch. With the introduction of sodium tetraphenylborate (NaBPh 4), the total conversion rate was promoted from an initial 18.07 % to 50.49 % and the γ-CD ratio reached 78.81 % with a yield of 39.79 g/L. Furthermore, the mechanism was conducted via the determination of binding constant, which indicated that γ-CD exhibited much stronger binding strength with NaBPh 4 than β-CD. The reformation of water molecules and the chaotropic effect might be the main driving forces for the interaction. Additionally, the conformations of CD complexes were depicted by NMR and molecular docking. The results further verified different binding patterns between CDs and tetraphenylborate ions, which might be the primary reason for the specific binding. This system not only guides γ-CD production with an efficient and easy-to-remove production aid but also offers a new perspective on the selection of complexing agents in CD production. [Display omitted] [ABSTRACT FROM AUTHOR]

Cyclodextrin-based metal-organic framework (CD-MOF) has been widely used in various delivery systems due to its excellent edibility and high drug loading capacity. However, its typically bulky size and high brittleness in aqueous solutions pose significant challenges for practical applications. Here, we proposed an ultrasonic-assisted method for rapid synthesis of uniformly-sized nanoscale CD-MOF, followed by its hydrophobic modification through ester bond cross-linking (Nano-CMOF). Proper ultrasound treatment effectively reduced particle size to nanoscale (393.14 nm). Notably, carbonate ester cross-linking method significantly improved water stability without altering its cubic shape and high porosity (1.3 cm3/g), resulting in a retention rate exceeding 90% in various media. Furthermore, the loading of quercetin did not disrupt cubic structure and showcased remarkable storage stability. Nano-CMOF achieved controlled release of quercetin in both aqueous environments and digestion. Additionally, Nano-CMOF demonstrated exceptional antioxidant (free radical scavenging 82.27%) and biocompatibility, indicating its significant potential as novel nutritional delivery systems in food and biomedical fields. [Display omitted] • Ultrasound-assisted hydrothermal method was developed for fabricating nanoscale CD-MOF. • CD-MOF cross-linked by ester bonds (Nano-CMOF) had a cubic structure and higher water stability. • Nano-CMOF as a carrier for quercetin enhanced its stability and antioxidant activity. • Nano-CMOF achieved controlled release of quercetin and had great biocompatibility. [ABSTRACT FROM AUTHOR]

• Acidic or basic form of Ellagic acid (EA) depends on the pH of the medium. • Effect of pH on inclusion complex formation of EA with γ-cyclodextrin(γ-CD). • γ-CD forms a 1:1 stoichiometric complex with EA. • The stability of the inclusion complex improved in an acidic medium. In food chemistry, the determination of the Ellagic acid (EA) from a food sample by Cyclodextrins (CDs) based nanosensor is a cheap, rapid, and sensitive method. EA acts as a ligand of CDs encapsulation. This study describes the effect of pH on EA and EA-γ-CD complex formation with the aid of spectroscopic and emission decay measurement. From this study, it was observed that pH of the medium has a high effect on the photophysical properties of EA and EA-γ-CD complexes. Due to larger cavity size, γ-CD forms a 1:1 stoichiometric complex with EA. Based on our results, it can be concluded that the stability of the complex between EA and γ-CD enhanced in an acidic medium. From the binding energy calculation by DFT method, it was observed that the encapsulation of EA in the cavity of γ-CD from the front side is more favorable compared to the back side to form EA-γ-CD complex. Such investigation should provide new information that will make it possible to improve the quality and safety of food. This study will be helpful in the use of γ-CD as a biosensor for EA determination. Graphic for table of contents. [Display omitted] [ABSTRACT FROM AUTHOR]

Enantioselective labeling of important bioactive molecules in complex biological environments by artificial receptors has drawn great interest. From both the slight difference of enantiomers’ physicochemical properties and inherently complexity in living organism point of view, it is still a contemporary challenge for preparing practical chiral device that could be employed in the model animal due to diverse biological interference. Herein, we introduce γ-cyclodextrin onto graphene oxide for fabricating γ-cyclodextrin and graphene oxide assemblies, which provided an efficient nanoplatform for chiral labelling of D-phenylalanine with higher chiral discrimination ratio of KD/KL = 8.21. Significantly, the chiral fluorescence quenching effect of this γ-CD-GO nanoplatform for D-phenylalanine enantiomer in zebrafish was 7.0-fold higher than L-isomer, which exhibiting real promise for producing practical enantio-differentiating graphene-based systems in a complex biological sample.

A three-component inclusion complex of ascorbyl palmitate (ASCP), urea (UR), and γ-cyclodextrin (γCD) with a molar ratio of 1/12 has been prepared for the first time using the evaporation method (EVP method) and the grinding and mixing method (GM method). Also, we investigated changes in the physicochemical properties of the three-component complexes. The powder X-ray diffraction (PXRD) measurements showed ASCP, UR, and γCD characteristic peaks in the physical mixture (PM) (AU (ASCP/UR = 1/12)/γCD = 1/2). In GM (AU (ASCP/UR = 1/12)/γCD = 1/1), new diffraction peaks were observed around 2θ = 7.5° and 16.6°, while characteristic peaks derived from EVP (ASCP/UR = 1/12) were observed at 2θ = 23.4° and 24.9°. On the other hand, new diffraction peaks at 2θ = 7.4° and 16.6° were observed in GM (1/2). In the differential scanning calorimeter (DSC) measurement, an endothermic peak at around 83 °C was observed in the GM (1/1) sample, which is thought to originate from the phase transition of urea from the hexagonal to the tetragonal form. An endothermic peak around 113.9 °C was also observed for EVP (ASCP/UR = 1/12). However, no characteristic phase transition-derived peak or EVP (ASCP/UR = 1/12)-derived endothermic peak was observed in GM (1/2). Near infrared (NIR) spectroscopy of GM (1/2) showed no shift in the peak derived from the CH group of ASCP. The peaks derived from the NH group of UR shifted to the high and low wavenumber sides at 5032 cm−1 and 5108 cm−1 in EVP (ASCP/UR = 1/12). The peak derived from the OH group of γCD shifted, and the peak derived from the OH group of ASCP broadened at GM (1/2). These results suggest that AU (ASCP/UR = 1/12)/γCD prepared by the mixed grinding method formed inclusion complexes at the molar ratio (1/2).

The extraordinary sensitivity of fluorescence spectroscopy has brought it to chemists' attention. Spectra recording at several interval times while the reaction is preceded, or at different complexing factor concentrations, is one case of policies by which data (second-order) can be created using the spectrofluorometric technique. In the current case, a mixed fluorescence spectrum of two Caffeic Acid (CA) and Ellagic Acid (EA) target analytes was documented as a γ-cyclodextrin (γ-CD) function (as an inclusion complexing factor) to produce data (second-order). At this point, Bilinear Least Squares/Residual Bilinearization (BLLS/RBL), as a second-order calibration technique, due to its benefits of accuracy, rapidity, simplicity, suitable concentration, and spectral resolution estimation even in the presence of the unknown interference (second-order advantage) was exploited for trilinear data deconvolution to obtain fluorescence spectra and concentration proles of the EA and CA as a function of γ-CD concentrations. A set of calibrations comprising 10 reference samples was employed to build the BLLS/RBL procedure. By a test set including 6 samples, the predictive ability of the technique was validated. The suggested model was effectively exploited to quantify CA and EA content in four fruit juice samples. [ABSTRACT FROM AUTHOR]

We presented an antibiotic-loaded γ-cyclodextrin metal-organic framework that delivered antibiotics suitable for the treatment of bacterial infections. The γ-cyclodextrin metal-organic framework was developed using γ-cyclodextrin and potassium ion via the ultrasonic method. The antibiotic (florfenicol and enrofloxacin) was primarily encapsulated into the pore structures of γ-CD-MOF, which allowed the sustained release of antibiotics over an extended period of time in vitro and in vivo. Notably, antibiotics-loaded γ-CD-MOF showed much superior activity against bacteria than free antibiotics (lower MIC value) and displayed better long-lasting activity (longer antibacterial time). The antibiotics-loaded γ-CD-MOF showed nontoxic and perfect biocompatibility to mammalian cells and tissues both in vitro and in vivo. These materials thus represent a novel drug-delivery device suitable for antibiotic therapy. This research is of great significance for reducing the generation of bacterial resistance and providing new ideas for the application of γ-CD-MOF.

Glaucoma is the leading cause of blindness worldwide. However, its surgical treatment, in particular via trabeculectomy, can be complicated by fibrosis. In current clinical practice, application of the drug, Mitomycin C, prevents or delays fibrosis, but can lead to additional side effects, such as bleb leakage and hypotony. Previous in silico drug screening and in vitro testing has identified the known antibiotic, josamycin, as a possible alternative antifibrotic medication with potentially fewer side effects. However, a suitable ocular delivery mechanism for the hydrophobic drug to the surgical site does not yet exist. Therefore, the focus of this paper is the development of an implantable drug delivery system for sustained delivery of josamycin after glaucoma surgery based on crosslinked γ-cyclodextrin. γ-Cyclodextrin is a commonly used solubilizer which was shown to complex with josamycin, drastically increasing the drug's solubility in aqueous solutions. A simple γ-cyclodextrin crosslinking method produced biocompatible hydrogels well-suited for implantation. The crosslinked γ - cyclodextrin retained the ability to form complexes with josamycin, resulting in a 4-fold higher drug loading efficiency when compared to linear dextran hydrogels, and prolonged drug release over 4 days.

Metal–Organic Frameworks (MOFs) are a class of coordination compounds with high versatility of design and a high loading ability. These properties have made them increasingly attractive for drug delivery, with research focusing mostly on the preparation of biocompatible MOFs. A suitable strategy is the use of cyclodextrins, cyclic oligosaccharides with excellent biosafety profiles. This review summarises the early steps taken in the application of cyclodextrin-coated and cyclodextrin-based MOFs in the treatment of bone-related diseases divided into three categories: cyclodextrin-coated MOFs, cyclodextrin-based MOFs and cross-linked derivatives of CD-MOFs. Applications in the delivery of bisphosphonates, osteoporotic regulating drugs and non-steroidal anti-inflammatory drugs, for osteoarthritis management, are highlighted. Lastly, the use of these materials in dentistry is exemplified with a recent report. [ABSTRACT FROM AUTHOR]

Alkalohalophilic Evansellacaseinilytica produced an extracellular cyclodextrin glycosyltransferase (CGTase) with cyclization activity of 43.5 ± 4.4 U/L in M1 medium containing 1% starch and 6% NaCl in nutrient broth at 37 ºC, pH 9.0, after 48 h. This is the first report of CGTase from this bacterium. 0.1% starch was found to induce CGTase, and further optimization using one variable at a time approach followed by statistical optimization led to 5.5-fold enhancement resulting in 240.5 ± 5.46 U/L. Six parameters were identified as positive signals using Plackett–Burman (PB). Of these, yeast extract, MgSO4 and tryptone were taken further for Response Surface Methodology (RSM) by disposing beef extract and fixing starch and soya peptone. The optimized M4 medium consisted of tryptone (0.1%, w/v), yeast extract (0.25%, w/v), MgSO4 (8 mM, w/v), potato starch (0.1%, w/v) and soya peptone (0.2%, w/v). CGTase was further purified with 6.44-fold purification and 19.32% yield employing starch affinity. It was found to be monomeric, corresponding to a size of 68 kDa as estimated by SDS-PAGE and was further confirmed to be 65 kDa by size exclusion chromatography. γ-Cyclodextrins were produced as the major product with a conversion of 5% soluble starch into 20.38% γ-cyclodextrins after 24 h reaction, as determined by HPLC. Peptide fingerprint after LC–MS analysis matched with IPT/TIG domain-containing protein within the genome of E. caseinilytica. Further blastp analysis revealed the closest homology with γ-CGTase from an alkalophilic E. clarkii, thereby confirming CGTase from E. caseinilytica as γ-CGTase. [ABSTRACT FROM AUTHOR]

Alkalohalophilic Evansellacaseinilytica produced an extracellular cyclodextrin glycosyltransferase (CGTase) with cyclization activity of 43.5 ± 4.4 U/L in M1 medium containing 1% starch and 6% NaCl in nutrient broth at 37 ºC, pH 9.0, after 48 h. This is the first report of CGTase from this bacterium. 0.1% starch was found to induce CGTase, and further optimization using one variable at a time approach followed by statistical optimization led to 5.5-fold enhancement resulting in 240.5 ± 5.46 U/L. Six parameters were identified as positive signals using Plackett–Burman (PB). Of these, yeast extract, MgSO4 and tryptone were taken further for Response Surface Methodology (RSM) by disposing beef extract and fixing starch and soya peptone. The optimized M4 medium consisted of tryptone (0.1%, w/v), yeast extract (0.25%, w/v), MgSO4 (8 mM, w/v), potato starch (0.1%, w/v) and soya peptone (0.2%, w/v). CGTase was further purified with 6.44-fold purification and 19.32% yield employing starch affinity. It was found to be monomeric, corresponding to a size of 68 kDa as estimated by SDS-PAGE and was further confirmed to be 65 kDa by size exclusion chromatography. γ-Cyclodextrins were produced as the major product with a conversion of 5% soluble starch into 20.38% γ-cyclodextrins after 24 h reaction, as determined by HPLC. Peptide fingerprint after LC–MS analysis matched with IPT/TIG domain-containing protein within the genome of E. caseinilytica. Further blastp analysis revealed the closest homology with γ-CGTase from an alkalophilic E. clarkii, thereby confirming CGTase from E. caseinilytica as γ-CGTase. [ABSTRACT FROM AUTHOR]

The crystal structure of the polymeric title compound, catena-poly[[[diaqualithium]-μ-γ-cyclodextrin(1−)-[aqualithium]-μ-γ-cyclodextrin(1−)] pentadecahydrate], {[Li2(C48H79O40)2(H2O)3]·15H2O}n, consists of deprotonated γ-cyclodextrin (CD) molecules assembled by lithium ions into metal–organic ribbons that are cross-linked by multiple O—H...O hydrogen bonds into sheets extending parallel to (0\overline11). Within a ribbon, one Li+ ion is coordinated by one deprotonated hydroxyl group of the first γ-CD torus and by one hydroxyl group of the second γ-CD torus as well as by two water molecules. The other Li+ ion is coordinated by one deprotonated hydroxyl and by one hydroxyl group of the second γ-CD torus, by one hydroxyl group of the first γ-CD torus as well as by one water molecule. The coordination spheres of both Li+ cations are distorted tetrahedral. The packing of the structure constitute channels along the a axis. Parts of the hydroxymethyl groups in cyclodextrin molecules as well as water molecules show two-component disorder. Electron density associated with additional disordered solvent molecules inside the cavities was removed with the SQUEEZE [Spek (2015). Acta Cryst. C71, 9–18] routine in PLATON. These solvent molecules are not considered in the given chemical formula and other crystal data. Five out of the sixteen hydroxymethyl groups and one water molecule are disordered over two sets of sites.

Host–guest assemblies open up opportunities for developing novel functional CLUSPOM multicomponent systems based on transition metal clusters (CLUS), polyoxometalates (POMs) and macrocyclic organic ligands. In water–ethanol solution γ-cyclodextrin (γ-CD) interacts with halide metal clusters [M6Cl14]2– (M = Mo, W) to form sandwich-type structures. The supramolecular association between the clusters and CDs, however, remains weak in solution, and the interactions are not strong enough to prevent the hydrolysis of the inorganic guest. Although analysis of the resulting crystal structures reveals inclusion complexation, 1H NMR experiments in solution show no specific affinity between the two components. The luminescent properties of the host–guest compounds in comparison with the initial cluster complexes are also studied to evaluate the influence of CD.

Rifampicin is a potent antimicrobial drug with some suboptimal properties, such as poor stability, low solubility, and variable bioavailability. Therefore, in the current study, a multicomponent complex between rifampicin, γ-cyclodextrin, and arginine was prepared with the aim of improving drug properties. Solubility was evaluated by phase-solubility studies. The mechanism of interaction was established through proton nuclear magnetic resonance spectroscopy and molecular modeling. Physicochemical characterization was investigated using Fourier transform-infrared spectroscopy, powder X-ray diffraction, and scanning electron microscopy. The dissolution properties, antimicrobial activity (antibacterial, antibiofilm, and antileishmanial), and stability of the different samples were studied. The results obtained in this investigation demonstrate that multicomponent complexes can improve the water solubility and dissolution rate of rifampicin, as well as its antibacterial and antileishmanial action, and present suitable stability. In conclusion, rifampicin complexed with γ-cyclodextrin and arginine is an attractive approach for developing pharmaceutical dosage forms of rifampicin with increased antimicrobial activities.

Metal-organic frameworks based on cyclodextrins (CDs) have been proposed as promising drug delivery systems due to their large surface area, variable pore size, and biocompatibility. In the current work, we investigated an incorporation of tolfenamic acid (TA), a representative of non-steroidal anti-inflammatory drugs (NSAIDs), in a metal-organic framework based on γ-cyclodextrin and potassium cations (γCD-MOF). Composites γCD-MOF/TA obtained by absorption and co-crystallization methods were characterized using powder X-ray diffraction, low temperature nitrogen adsorption/desorption, scanning electron microscopy, and FTIR spectroscopy. It was demonstrated that TA loaded in γCD-MOF has an improved dissolution profile. However, the inclusion of TA in γ-CD reduces the membrane permeability of the drug. A comparative analysis of the encapsulation of different NSAIDs in γCD-MOF was performed. The impact of NSAID structure on the loading capacity was considered for the first time. It was revealed that the presence of heterocycles in the structure and drug lipophilicity influence the loading efficiency of NSAIDs in γCD-MOF.

To enhance the oral bioavailability of heparin, a self-nano-emulsifying drug delivery system (SNEDDS) was developed using hydrophobic ion-pairing with cationic polymers of α-, ß-, and γ-cyclodextrins (CPCDs). Hydrophobic ion paired complexes were formed, and the recovery of heparin was determined in n-hexane and isopropyl myristate (IPM). The SNEDDSs were prepared and were optimized using D-optimal response surface methodology (RSM). The determination of the recovery of complexes in IPM revealed that in cationic α-cyclodextrin, the highest recovery was achieved at the heparin: CPCD weight ratio of 1:0.5. However, in cationic ß-cyclodextrin the highest recovery was obtained at the weight ratio of 1:4. Similar to CPßCD, for ealed that in c the highest recovery was obtained at 1:4 weight ratio. The size of optimized nano-droplets was found to be 127.00 ± 4.1, 184.00 ± 6.43, and 216.00 ± 5.43 nm; polydispersity index (PdI) values were reported as 0.372 ± 0.005, 0.163 ± 0.008, 0.236 ± 0.003; and calculated loading efficiency (LE%) were 84.60 ± 3.62, 91.06 ± 2.49, and 92.81 ± 0.70% for SNEDDS preparations incorporating cationic derivatives of α-, ß-, and γ-cyclodextrin, respectively. The in vitro release study revealed that SNEDDS preparations containing cationic γ-cyclodextrin posed the slowest release rate. Data achieved from cellular uptake study showed that the SNEDDS containing α-cyclodextrin had the highest cumulative uptake percentage after 6 h post-exposure; same results were obtained in the intestinal transport study demonstrating SNEDDS containing α-cyclodextrin posed the highest transport efficiency with Papp of 24.85 × 10−r ± 1.06 × 10−± cm.s−m. [ABSTRACT FROM AUTHOR]

Porous materials have been widely studied for encapsulation and controlled release of active species for packaging applications. This study examines the encapsulation efficiency of hexanal in γ-cyclodextrin metal organic frameworks (γ-CDMOF) for potential active packaging applications. γ-CDMOF was synthesized and hexanal was encapsulated in the MOF using a vapor diffusion process. The synthesized MOF was characterized both before and after the encapsulation of hexanal using x-ray diffraction (XRD), scanning electron microscopy (SEM), differential scanning calorimetry (DSC), fourier transform infrared spectroscopy (FTIR) and thermogravimetric analysis (TGA). The diffraction peaks of various planes obtained from XRD characterization matched the theoretically calculated values. We identified the most stable docking sites using energy minimization calculations. FTIR and computational studied indicated hydrogen bonding interactions play a significant role in the stabilization of hexanal and γ-CDMOF inclusion complex. TGA characterization results revealed an encapsulation efficiency of about 15%. DSC and SEM study also supported encapsulation of hexanal in γ-CDMOF. [ABSTRACT FROM AUTHOR]

Geraniol (Ger) is an essential oil molecule with excellent biological activity. High hydrophobicity and volatility limit its practical application. Cyclodextrins (CDs) are water-soluble cyclic oligosaccharides with hydrophobic cavities. Physical encapsulation of CDs to improve the solubility and stability of essential oil molecules is not satisfactory. Therefore, this study synthesized the γ-CD derivative (γ-CD-Ger) by grafting Ger onto γ-CD using a bromide-mediated method. Compared to the inclusion complexes (γ-CD/Ger) formed by both, the derivatives exhibit better solubility and thermal stability. The derivative has better antibacterial activity when the ratio of γ-CD to Ger was 1:2. In addition, the derivatives did not exhibit cytotoxic and hemolytic properties. These results indicate that this research provides a water-soluble antibacterial agent with a wide range of promising applications and offers new ideas for the application of alcohol hydrophobic molecules in aqueous systems. [Display omitted] • The coupling of geraniol and γ-cyclodextrin was achieved for the first time. • Geraniol-modified γ-cyclodextrin has good antibacterial effect in aqueous systems. • The derivatives have better stability and solubility than inclusions. • The prepared derivatives have no significant cytotoxic and hemolytic activity. [ABSTRACT FROM AUTHOR]

Na- l -Thyroxine (Na- l -Thy) is a frequently prescribed synthetic hormone for hypothyroidism treatment. Despite its efficacy, its hydrophobic nature poses a challenge for achieving optimal bioavailability. To address this, researchers explored various delivery methods, including micro-formulations and nano-formulations, for precise and prolonged release of hydrophobic and hydrophilic drugs. In this study, we developed micro-formulations with cyclodextrin and chitosan. Docking studies identified γ -cyclodextrin as the preferred option for forming a stable complex with Na- l -Thyroxine compared to α , and β -cyclodextrins. Two micro-formulations were prepared compared: Na- l -Thyroxine loaded on chitosan (CS + Na- l -Thy) and Na- l -Thyroxine and γ -cyclodextrin inclusion complex (IC) loaded on chitosan (CS + IC). CS + IC exhibited superior encapsulation efficiency (91.25 %) and loading capacity (18.62 %) compared to CS + Na- l -Thy (encapsulation efficiency: 70.24 %, loading capacity: 21.18 %). Characterization using FTIR, SEM, and TGA validated successful encapsulation of Na- l -Thy in spherical microparticles with high thermal stability. In-vitro release studies at pH 1.2 and 7.4 showed that the CS + IC microparticles displayed gradual, consistent drug release compared to CS + Na- l -Thy -Thy. Both formulations showed faster release at pH 1.2 than at pH 7.4. Reaction kinetics analysis of release studies of CS + Na- l -Thy and CS + IC were best described by Higuchi kinetic model and Korsemeyer-Peppas kinetic model respectively. This study suggests that the CS + IC microparticles are an effective and stable delivery system for sustained release of hydrophobic Na- l -Thy. [ABSTRACT FROM AUTHOR]

[Display omitted] • EGCG was encapsulated in phospholipid nanovesicles with emulsion-transfer methods. • The addition of γ-cyclodextrin in nanovesicles had better EGCG encapsulation. • Cyclodextrin could improve EGCG sustained releases in phospholipid nanovesicles. • Nanovesicle could prevent the binding of EGCG with mucin and mask its bitterness. A novel phospholipid-based nanovesicle (PBN) was developed to encapsulate (-)-epigallocatechin gallate (EGCG), a major polyphenol in green tea, to mask its bitter taste and expand its application in food products. The PBN was formed using W/O emulsion-transfer methods and showed a multilayer membrane nanovesicle structure (around 200 nm) observed with TEM. The PBN possessed a high encapsulation efficiency (92.1%) for EGCG. The bitterness of EGCG was significantly reduced to 1/12 after encapsulation. Fourier transform infrared spectroscopy (FTIR) indicated the EGCG mainly interacted with the upper chain/glycerol/head group region of the lipid bilayer in PBN. Quartz crystal microbalance with dissipation (QCM-D) showed the addition of γ-cyclodextrin in PBN enhanced EGCG's adsorption with phospholipids and allowed for its good sustained release. Encapsulating EGCG in PBN inhibited its complexation with mucin, reducing bitterness and astringency. This provides a new method to improve EGCG's flavor, potentially expanding its application in the food industry. [ABSTRACT FROM AUTHOR]

A natural polysaccharide-based vehicle is facilely prepared for enantioselective loading of S-naproxen (S-NPX) and its programmed release. Cyclodextrin metal-organic frameworks (CD-MOF) are synthesized through the coordination of K+ with γ-cyclodextrin (γ-CD). Compared with R-NPX, the CD-MOF preferably combines with S-NPX, which can be confirmed by the thermodynamic calculations. The S-NPX loaded CD-MOF (CD-MOF-S-NPX) is grafted with disulfide bond (–S–S–) to improve its hydrophobicity, and the loaded S-NPX is further encapsulated in the chiral cavity of γ-CD by carboxymethyl potato starch (CPS) hydrogels. The intermolecular hydrogen bonding of the CPS hydrogels is prone to be destroyed in mildly basic media (∼pH 8.0), resulting in the swelling of the hydrogels; the –S–S– linkage in the vehicle can be cleaved in the presence of glutathione (GSH), leading to the collapse of the CD-MOF. Therefore, the programmed release of S-NPX can be achieved. Also in this work, the release kinetics is investigated, and the results indicate that the release of S-NPX is controlled by the Higuchi model. • A γ-CD-based vehicle is facilely prepared for chiral separation of the NPX isomers. • The CD-MOF-S-NPX is grafted with –S–S– bond to improve the hydrophobicity. • The loaded S-NPX is further encapsulated by the CPS hydrogels. • Programmed release of S-NPX from the SS-CD-MOF-S-NPX-gel is achieved. • Release kinetics reveals that the release of S-NPX is controlled by Higuchi model. [ABSTRACT FROM AUTHOR]