Synthesis and characterization of fluorescent poly(α-cyclodextrin)/carbon quantum dots composite for efficient removal and detection of toluene and xylene from aqueous media.

This study reports the synthesis and characterization of a supramolecular composite comprised of carbon dots (CDots) embedded within net-poly[(α-cyclodextrin)-ν-(citric acid)] (α-CD/CA/CDots) for the removal and detection of toluene and xylene from aqueous media. The remarkable stability of CDots within the composite enables the preservation of photoluminescence properties for prolonged storage and extended UV-light irradiation. As demonstrated, following the adsorption of both organic compounds, the composite detected them in the aqueous medium due to a fluorescence quenching mechanism. Spectroscopic analyses reveal that the accessible Stern-Volmer quenching constants for toluene and xylene are KSVa = 15.4 M-1 and KSVa = 10.3 M-1, respectively. As a result, the α-CD/CA/CDots composite were sensitive to the tested volatile organic compounds (LODtoluene = 3.7 mg/L and LODxylene = 4.9 mg/L). Optimal conditions for toluene and xylene adsorption were found, allowing to achieve noticeable adsorption capabilities (qe(toluene) = 68.9 and qe(xylene) = 48.2 mg/g) and removal efficiencies exceeding 70%. Different characterization techniques confirmed the successful synthesis of the composite and elucidated the interaction mechanisms between the adsorbent and the tested compounds. In summary, the multifunctionality demonstrated by the α-CD/CA/CDots composite ranks it as an efficient and promising adsorbent and detection probe for this class of water contaminants.

Water-responsive supercontractile polymer films for bioelectronic interfaces.

Connecting different electronic devices is usually straightforward because they have paired, standardized interfaces, in which the shapes and sizes match each other perfectly. Tissue-electronics interfaces, however, cannot be standardized, because tissues are soft1-3 and have arbitrary shapes and sizes4-6. Shape-adaptive wrapping and covering around irregularly sized and shaped objects have been achieved using heat-shrink films because they can contract largely and rapidly when heated7. However, these materials are unsuitable for biological applications because they are usually much harder than tissues and contract at temperatures higher than 90 °C (refs. 8,9). Therefore, it is challenging to prepare stimuli-responsive films with large and rapid contractions for which the stimuli and mechanical properties are compatible with vulnerable tissues and electronic integration processes. Here, inspired by spider silk10-12, we designed water-responsive supercontractile polymer films composed of poly(ethylene oxide) and poly(ethylene glycol)-α-cyclodextrin inclusion complex, which are initially dry, flexible and stable under ambient conditions, contract by more than 50% of their original length within seconds (about 30% per second) after wetting and become soft (about 100 kPa) and stretchable (around 600%) hydrogel thin films thereafter. This supercontraction is attributed to the aligned microporous hierarchical structures of the films, which also facilitate electronic integration. We used this film to fabricate shape-adaptive electrode arrays that simplify the implantation procedure through supercontraction and conformally wrap around nerves, muscles and hearts of different sizes when wetted for in vivo nerve stimulation and electrophysiological signal recording. This study demonstrates that this water-responsive material can play an important part in shaping the next-generation tissue-electronics interfaces as well as broadening the biomedical application of shape-adaptive materials.

Thiolated α-cyclodextrin: The likely smallest drug carrier providing enhanced cellular uptake and endosomal escape.

This study aimed to evaluate the effect of thiolated α-cyclodextrin (α-CD-SH) on the cellular uptake of its payload. For this purpose, α-CD was thiolated using phosphorous pentasulfide. Thiolated α-CD was characterized by FT-IR and 1H NMR spectroscopy, differential scanning calorimetry (DSC), and powder X-ray diffractometry (PXRD). Cytotoxicity of α-CD-SH was evaluated on Caco-2, HEK 293, and MC3T3 cells. Dilauryl fluorescein (DLF) and coumarin-6 (Cou) serving as surrogates for a pharmaceutical payload were incorporated in α-CD-SH, and cellular uptake was analyzed by flow cytometry and confocal microscopy. Endosomal escape was investigated by confocal microscopy and hemolysis assay. Results showed no cytotoxic effect within 3 h, while dose-dependent cytotoxicity was observed within 24 h. The cellular uptake of DLF and Cou was up to 20- and 11-fold enhanced by α-CD-SH compared to native α-CD, respectively. Furthermore, α-CD-SH provided an endosomal escape. According to these results, α-CD-SH is a promising carrier to shuttle drugs into the cytoplasm of target cells.

Cholesterol crystal formation is a unifying pathogenic mechanism in the development of diabetic retinopathy.

AIMS/HYPOTHESIS: Hyper-reflective crystalline deposits found in retinal lesions have been suggested to predict the progression of diabetic retinopathy, but the nature of these structures remains unknown. METHODS: Scanning electron microscopy and immunohistochemistry were used to identify cholesterol crystals (CCs) in human donor, pig and mouse tissue. The effects of CCs were analysed in bovine retinal endothelial cells in vitro and in db/db mice in vivo using quantitative RT-PCR, bulk RNA sequencing, and cell death and permeability assays. Cholesterol homeostasis was determined using 2H2O and 2H7-cholesterol. RESULTS: We identified hyper-reflective crystalline deposits in human diabetic retina as CCs. Similarly, CCs were found in the retina of a diabetic mouse model and a high-cholesterol diet-fed pig model. Cell culture studies demonstrated that treatment of retinal cells with CCs can recapitulate all major pathogenic mechanisms leading to diabetic retinopathy, including inflammation, cell death and breakdown of the blood-retinal barrier. Fibrates, statins and α-cyclodextrin effectively dissolved CCs present in in vitro models of diabetic retinopathy, and prevented CC-induced endothelial pathology. Treatment of a diabetic mouse model with α-cyclodextrin reduced cholesterol levels and CC formation in the retina, and prevented diabetic retinopathy. CONCLUSIONS/INTERPRETATION: We established that cholesterol accumulation and CC formation are a unifying pathogenic mechanism in the development of diabetic retinopathy.

Improved Swelling Property of Tissue Adhesive Hydrogels Based on α-Cyclodextrin/Decyl Group-Modified Alaska Pollock Gelatin Inclusion Complexes.

Adhesives/sealants are used after suturing to prevent leakage of cerebrospinal fluid from an anastomotic site. Commercial adhesives/sealants have been used to close the cerebral dura. However, swelling of the cured adhesives/sealants induces increased intracranial pressure and decreases the strength of the seal. In the present study, tissue adhesive hydrogels with improved swelling property using inclusion complex composed of α-cyclodextrin (αCD) and decyl group (C10)-modified Alaska pollock-derived gelatin (C10-ApGltn) with a high degree of substitution (DS) (>20 mol%) are developed. Viscosity of C10-ApGltn with a high DS solution remarkably decreased by the addition of αCD. The resulting αCD/C10-ApGltn adhesive hydrogel composed of αCD/C10-ApGltn inclusion complexes and poly(ethylene glycol) (PEG)-based crosslinker showed improved swelling property after immersion in saline. Also, the resulting adhesive has a significantly higher burst strength than fibrin-based adhesives and is as strong as a PEG-based adhesive. Quantitative analysis of αCD revealed that the improved swelling property of the resulting adhesive hydrogels is induced by the release of αCD from cured adhesive, and the subsequent assembly of decyl groups in the saline. These results suggest that adhesives developed using the αCD/C10-ApGltn inclusion complex can be useful for closing the cerebral dura mater.

Reduction of thyroid radioactive iodine exposure by oral administration of cyclic oligosaccharides.

Alpha-cyclodextrin, a six D-glucose cyclic oligosaccharide, has several applications in food and pharmaceuticals, but has also been reported to retain iodine in a stable manner for 16 months. Radioactive iodine, which may cause thyroid cancer and hypofunction, must be properly managed. If the absorption of radioactive iodine is suppressed, it can be expected to lead to a reduction in thyroid exposure. This study clarified the inhibition of radioactive iodine absorption by the oral administration of α-cyclodextrin in a murine model using direct measurement of single photon emission computed tomography. The uptake of radioactive iodine into the thyroid gland in mice administered with radioactive iodine and an α-cyclodextrin solution was approximately 40% lower after 24 h. The finding that oral uptake of α-cyclodextrin has an inhibitory effect on the transfer of radioactive iodine to the thyroid gland has potential for application in many fields such as food, pharmaceuticals, nuclear emergency preparedness, and medicine.

Glucocorticoid-loaded pH/ROS dual-responsive nanoparticles alleviate joint destruction by downregulating the NF-κB signaling pathway.

Rheumatoid arthritis (RA) is an autoimmune disease causing severe symptoms that are difficult to treat. Nano-drug delivery system is recognized as a promising strategy for management of RA. However, how to thoroughly release payloads from nanoformulations and synergistic therapy of RA needs to be further investigated. To address this issue, a pH and reactive oxygen species (ROS) dual-responsive, methylprednisolone (MPS)-loaded and arginine-glycine-aspartic acid (RGD)-modified nanoparticles (NPs) was fabricated using phytochemical and ROS-responsive moiety co-modified α-cyclodextrin (α-CD) as a carrier. In vitro and in vivo experiments verified that the pH/ROS dual-responsive nanomedicine could be efficiently internalized by activated macrophages and synovial cells, and the released MPS could promote transformation of M1-type macrophages into M2 phenotype, thereby down-regulating pro-inflammatory cytokines. In vivo experiments demonstrated that the pH/ROS dual-responsive nanomedicine was remarkably accumulated in the inflamed joints of mice with collagen-induced arthritis (CIA). The accumulated nanomedicine could obviously relieve joint swelling and cartilage destruction without obvious adverse effects. Importantly, the expression of interleukin-6 and tumor necrosis factor-α in the joints of CIA mice were significantly inhibited by the pH/ROS dual-responsive nanomedicine in comparison with free drug and non-targeted counterparts. In addition, the expression of the NF-κB signaling pathway molecule P65 was also significantly decreased by nanomedicine-treatment. Our results reveal that MPS-loaded pH/ROS dual-responsive NPs can effectively alleviate joint destruction via down-regulation of the NF-κB signaling pathway. STATEMENT OF SIGNIFICANCE: Nanomedicine is recognized as an attractive method for the targeting treatment of rheumatoid arthritis (RA). To thorough release of payloads from nanoformulations and synergistic therapy of RA, herein, a phytochemical and ROS-responsive moiety co-modified α-cyclodextrin was used as a pH/ROS dual-responsive carrier to encapsulate methylprednisolone to manage RA. The fabricated nanomedicine can effectively release its payloads under pH and/or ROS microenvironment, and the released drugs dramatically promote transformation of M1-type macrophages into M2 phenotype to reduce the release of pro-inflammatory cytokines. The prepared nanomedicine also obviously decreased the NF-κB signaling pathway molecule P65 expression in the joints, thereby down-regulating pro-inflammatory cytokines expression to alleviate joint swelling and cartilage destruction. We provided a candidate for the targeting treatment of RA.

Recognition of malathion pesticides in agricultural samples by using α-CD functionalized gold nanoparticles as a colorimetric sensor.

Herein, a rapid, precise alpha-cyclodextrin (α-CD) based gold nanoparticles (AuNPs) for selective detection of malathion pesticides has been reported. These are organophosphorus pesticides (OPPs), that can cause a neurological disease by inhibiting the activity of acetylcholinesterase (AChE). It is important to exploit a quick and sensitive approach for monitoring OPPs. Hence in the present work, a colorimetric assay for the detection of malathion has been developed as a model of OPPs from the environmental sample matrices. The physical and chemical properties of synthesized alpha-cyclodextrin stabilized gold nanoparticles (AuNPs/α-CD) were studied with various characterization techniques, including UV-visible spectroscopy, TEM, DLS and FTIR. The designed sensing system displayed linearity in the broad range of malathion concentrations, 10-600 ng mL-1 with a limit of detection and the limit of quantification values 4.03 ng mL-1 and 12.96 ng mL-1, respectively. The application of the designed chemical sensor was extended to the malathion pesticide determination in real samples such as vegetables, which resulted in almost 100% recovery rates in all the spiked samples. Thus, due to these advantages, the present study established a selective, facile and sensitive colorimetric platform for the direct detection of malathion within a very short time (5 min) with a low detection limit. The practicality of the constructed platform was further executed by the detection of the pesticide in vegetable samples.

L-asparaginase immobilization in supramolecular nanogels of PEG-grafted poly HPMA and bis(α-cyclodextrin) to enhance pharmacokinetics and lower enzyme antigenicity.

L-asparaginase (ASNase) enzyme has limited therapeutic use due to its poor pharmacokinetics and immunogenicity. To overcome these obstacles, we immobilized ASNase in biocompatible poly hydroxypropyl methacrylamide (P(HPMA))-based nanogels simply formed through the host-guest inclusion complex of ASNase-conjugated random copolymer of HPMA and polyethylene glycol (PEG) acrylate (P(HPMA-MPEGA)) and α-cyclodextrin dimer (bisCD) using cystamine as a linker. The effects of bisCD and polymer concentrations on particle size, gelation time, and recovery of enzyme activity were investigated. The ASNase-conjugated bisCD nanogels were discrete, homogeneous, and spherical with a mean projected diameter of 148 ± 41 nm. ASNase immobilized in the bisCD nanogels caused cytotoxicity on HL-60 cell line with IC50 of 3 IU/ml. In-vivo rat study revealed that the immobilized ASNase reduced the enzyme antigenicity and resulted in 8.1 folds longer circulation half-life than the native enzyme. Conclusively, immobilization of ASNase in P(HPMA-MPEGA) and bisCD supramolecular nanogels could enhance the therapeutic value of ASNase in cancer chemotherapy.

Sangelose-based gels and films: effects of glycerol and α-cyclodextrin and their pharmaceutical application.

OBJECTIVE: To evaluate the possible application of Sangelose as an alternative to gelatin and carrageenan for the development of film substrates, and to examine the effect of glycerol and α-cyclodextrin (α-CyD) on the viscoelastic properties of Sangelose-based gels and the physical properties of the films. SIGNIFICANCE: Sangelose-based gels/films can serve as a potential viable alternative to gelatin and carrageenan in pharmaceutical applications. METHODS: Glycerol (a plasticizer) and α-CyD (a functional additive) were added to Sangelose, and gels and films were prepared. The gels were evaluated by dynamic viscoelasticity measurements, and the films were evaluated by scanning electron microscopy, Fourier-transform infrared spectroscopy, tensile tests, and contact angle measurements. Soft capsules were prepared using the formulated gels. RESULTS: The strength of the gels was affected when only glycerol was added to Sangelose and α-CyD addition resulted in rigid gels. However, the addition of α-CyD with 10% glycerol weakened the gels. Tensile tests suggested that glycerol addition affected the formability and malleability of the films, while α-CyD addition affected their formability and elongation properties. The addition of 10% glycerol and α-CyD did not affect the flexibility of the films, suggesting that the malleability and strength were impacted. Soft capsules could not be prepared by adding only glycerol or α-CyD to Sangelose. Soft capsules with favorable disintegration behavior were obtained upon adding α-CyD to gels along with 10% glycerol. CONCLUSIONS: Sangelose combined with a suitable amount of glycerol and α-CyD has preferable characteristics for film formation and may have potential applications in the pharmaceutical and health food sectors.

Bacteroides uniformis and its preferred substrate, α-cyclodextrin, enhance endurance exercise performance in mice and human males.

Although gut microbiota has been linked to exercise, whether alterations in the abundance of specific bacteria improve exercise performance remains ambiguous. In a cross-sectional study involving 25 male long-distance runners, we found a correlation between Bacteroides uniformis abundance in feces and the 3000-m race time. In addition, we administered flaxseed lignan or α-cyclodextrin as a test tablet to healthy, active males who regularly exercised in a randomized, double-blind, placebo-controlled study to increase B. uniformis in the gut (UMIN000033748). The results indicated that α-cyclodextrin supplementation improved human endurance exercise performance. Moreover, B. uniformis administration in mice increased swimming time to exhaustion, cecal short-chain fatty acid concentrations, and the gene expression of enzymes associated with gluconeogenesis in the liver while decreasing hepatic glycogen content. These findings indicate that B. uniformis enhances endurance exercise performance, which may be mediated by facilitating hepatic endogenous glucose production.

A novel signal amplification strategy for label-free electrochemical DNA sensor based on the interaction between α-cyclodextrin and ferrocenyl indicator.

The synthesized ferrocene appended naphthalimide derivative (FND) exhibited great binding ability toward dsDNA, while its usage as the electrochemical hybridization indicator was restricted by the poor water solubility. Herein, a simple and effective signal amplification strategy for FND based label-free DNA biosensors was developed based on the interaction between FND and cyclodextrin. α-Cyclodextrin (α-CD), ß-cyclodextrin (ß-CD) and γ-cyclodextrin (γ-CD) were helpful to amplify the signal of the DNA biosensor, while the signal amplification effect of α-CD was better than that of ß-CD and γ-CD. Under the optimum conditions, there was a 3-fold increase in the sensitivity of the DNA biosensor after the addition of α-CD. The interaction between FND and α-/ß-/γ-CD was investigated by differential pulse voltammetry and fluorescence experiment. Experimental results showed that α-CD not only minimized the impact on the electrochemical activity of FND but also improved the dispersity of FND in aqueous solution. That was why the proposed biosensor showed higher sensitivity in the presence of α-CD. This strategy was universal for other ferrocenyl indicators with similar structures as used in this work.

α-Cyclodextrin-based poly(pseudo)rotaxane for antifungal drug delivery to the vaginal mucosa.

This work aimed to evaluate poly(pseudo)rotaxanes (PPRs) potential for vaginal antifungal delivery. For this, PPRs containing terbinafine (TB) 2 % were obtained using two small surfactants, Kolliphor® RH40 and Gelucire® 48/16, and different α-cyclodextrin (α-CD) concentrations (5 and 10 %). PPRs were characterized by their physicochemical characteristics, irritation, and mucoadhesion capabilities. Formulations' performance was assessed in a vertical penetration model, which uses ex vivo entire porcine vagina. Conventional penetration experiments with excised vaginal tissue were performed as a control. Results showed all formulations were non-irritant according to the HET-CAM test. Furthermore, PPRs with 10 % αCD showed superior mucoadhesion (p < 0.05). Conventional horizontal penetration studies could not differentiate formulations (p > 0.05). However, PPRs with 10 % αCD presented a better performance in vertical ex vivo studies, achieving higher drug penetration into the vaginal mucosa (p < 0.05), which is probably related to the formulation's prolonged residence time. In addition, the antifungal activity of the formulations was maintained against Candida albicans and C. glabrata cultures. More importantly, the formulation's viscosity and drug delivery control had no negative impact on the antifungal activity. In conclusion, the best performance in a more realistic model evidenced the remarkable potential of PPRs for vaginal drug delivery.

Solid Xenon Carrier Based on α-Cyclodextrin: Properties, Preparation, and Application.

The inert gas xenon (Xe) is increasingly used in medicine as a universal anesthetic, a regulator of cellular metabolism, and a broad-spectrum organoprotector. Commonly utilized Xe inhalation requires expensive equipment that is not universally available. Here we describe the production process and physical characteristics of a solid, highly stable xenon carrier based on α-cyclodextrin (α-CD), developed for oral administration. It was found, that the interaction of α-CD with Xe in an aqueous solution and elevated pressure leads to precipitation of the α-CD-Xe complex. We have discovered three new properties of the resulting complex that promote long-term storage and oral delivery of Xe. (i) At temperatures below 0 °C, the precipitated α-CD-Xe complex containing water is so stable that it allows the removal of water by vacuum freeze-drying (lyophilization). (ii). Lyophilized α-CD-Xe remains stable for months at room temperature. (iii) Upon contact with water, α-CD-Xe rapidly releases gaseous Xe. As revealed in the forced swim test, after oral administration of lyophilized α-CD-Xe to rats, the duration of swimming was significantly increased. The obtained data open up prospects for the development of drugs based on the lyophilized α-CD-Xe complex suitable for storage, transportation, and medical use, including outside the hospital.

The Impact of Low-Viscosity Soluble Dietary Fibers on Intestinal Microenvironment and Experimental Colitis: A Possible Preventive Application of Alpha-Cyclodextrin in Intestinal Inflammation.

SCOPE: The purpose of this study is to compare the impact of four low-viscosity soluble dietary fibers (DFs) on the intestinal microenvironment, in terms of microbiota composition, short-chain fatty acid (SCFA) production, proportion of colonic peripherally induced regulatory T cells (pTregs), and experimental colitis in mice. METHODS AND RESULTS: Mice are administered 5% w/v low-viscosity soluble DFs in drinking water for 2 weeks. The gut microbiota composition is determined using 16S rRNA sequencing. Luminal SCFAs are quantified by gas chromatography, and colonic pTregs are analyzed using flow cytometry. All low-viscosity soluble DFs promote the growth of beneficial bacteria such as Akkermansia muciniphila and Bacteroides acidifaciens, while eliminating pathogenic bacteria such as Clostridium perfringens. Moreover, two low-viscosity soluble DFs significantly increase the abundance of commensal bacteria and promote the accumulation of propionate and butyrate, leading to marked induction of colonic pTregs. Consistently, these two fibers, in particular α-cyclodextrin, show remarkable anti-inflammatory properties in a colitis mouse model. CONCLUSION: Mice administered any low-viscosity soluble DF show comparable gut microbiota compositions, but differ in terms of bacterial abundance, SCFA concentration, pTreg population, and colitis development. This exploratory study suggests that administration of α-cyclodextrin may be a possible strategy for the prevention of colitis.

Polypseudorotaxane hydrogel based on Tween 80 and α-cyclodextrin for sustained delivery of low molecular weight heparin.

Low molecular weight heparin (LMWH), an anionic polysaccharide, has been widely used as a clinical anticoagulant. However, repeated subcutaneous injection is sometimes required due to its short half-life. To reduce the dosing frequency, the injectable polypseudorotaxane hydrogel was fabricated by inclusion complexation formation between Tween 80 and α-Cyclodextrin (αCD) for sustained release of LMWH. The physicochemical properties of such hydrogel were characterized by SEM, XRD, DSC, and FTIR. This hydrogel showed shear-thinning and thixotropic behavior and was easily injected through standard syringe needles. The gelation time, mechanical strength, shear viscosity, in vitro drug release rate, in vitro hydrogel dissolution rate, and in vivo hydrogel retention could be tuned by αCD concentration in the hydrogel. In vivo safety evaluation indicated that the polypseudorotaxane hydrogel was biocompatible. Most importantly, this polypseudorotaxane hydrogel could sustain release of LMWH after subcutaneous injection.

Economical gold recovery cycle from bio-sensing AuNPs: an application for nanowaste and COVID-19 testing kits.

We report the controlled growth of biologically active compounds: gold nanoparticles (AuNPs) in various shapes, including their green synthesis, characterization, and studies of their applications towards biological, degradation and recycling. Using spectroscopic methods, studies on responsive binding mechanisms of AuNPs with biopolymers herring sperm deoxyribonucleic acid (hsDNA), bovine serum albumin (BSA), dyes degradation study, and exquisitely gold separation studies/recovery from nanowaste, COVID-19 testing kits, and pregnancy testing kits are discussed. The sensing ability of the AuNPs with biopolymers was investigated via various analytical techniques. The rate of degradation of various dyes in the presence and absence of AuNPs was studied by deploying stirring, IR, solar, and UV-Vis methods. AuNPs were found to be the most active cytotoxic agent against human breast cancer cell lines such as MCF-7 and MDAMB-468. Furthermore, an economical process for the recovery of gold traces from nanowaste, COVID-19 detection kits, and pregnancy testing kits was developed using inexpensive and eco-friendly α-cyclodextrin sugar. This method was found to be easy and safest in comparison with the universally accepted cyanidation process. In the future, small gold jewelry makers and related industries would benefit from the proposed gold-recycling process and it might contribute to their socio-economic growth. The methodologies proposed are also beneficial for trace-level forensic investigation.

Studies of the Formation of Inclusion Complexes Derivatives of Cinnamon Acid with α-Cyclodextrin in a Wide Range of Temperatures Using Conductometric Methods.

The electrical conductivities of aqueous solutions of sodium salts of trans-4-hydroxycinnamic acid (trans-p-coumaric acid), trans-3,4-dihydroxycinnamic acid (trans-caffeic acid), trans-4-hydroxy-3-methoxycinnamic acid, (trans-ferulic acid) and trans-3-phenylacrylic acid (trans-cinnamic acid) with α-cyclodextrin were measured in the temperature range of 288.15 K-318.15 K. For the first time in the literature, using the limiting molar conductivity (Λmo) obtained from conductivity measurements, the values of the complexation constants (Kf) of the salts of phenolic acid derivatives with α-cyclodextrin were determined using a modified low concentration chemical model (IcCM). An attempt was also made to analyze the individual thermodynamic functions ΔGo, ΔHo and ΔSo describing the complexation process as a function of temperature changes. The obtained results show that the process of formation of inclusion complexes is exothermic and is spontaneous.

Pseudo-polymorphism of a camphor α-cyclodextrin complex.

Crystalline products of vapor diffusion of an alcoholic solution of 1R,4R-camphor into an aqueous solution of α-cyclodextrin were prepared and subjected to X-ray structure analysis. Two different forms were obtained: a dimeric cavity formed by head-to-head association of cyclodextrin (phase A), and a complex set of monomeric cavities (phase B). Both contain camphor molecules orientationally disordered inside cavities. The structures are solvated by mixtures of water and ethanol. The structures significantly differ in chemical stabilities. Whilst phase A is relatively stable with respect to guest desorption, phase B rapidly reacts to change of its chemical environment manifested by cracking of crystals in solution. The phenomenon has been recorded and a short movie is included in the supplementary data.

Positive postprandial glycaemic and appetite-related effects of wheat breads enriched with either α-cyclodextrin or hydroxytyrosol/α-cyclodextrin inclusion complex.

PURPOSE: Enrichment of wheat bread with either α-cyclodextrin (α-CD) or an inclusion complex of hydroxytyrosol (HT) and α-CD was performed to examine potential postprandial benefits. METHODS: Ten healthy normoglycaemic adults were provided with either a glucose solution (reference food, GS), white wheat bread (WB), wheat bread enriched with α-CD (α-CDB) or wheat bread enriched with HT/α-CD complex ((HT + α-CD)B), with 1-week intervals in amounts that yielded 50 g of available carbohydrates. Venous blood samples were collected before consumption and at 15, 30, 45, 60, 90, 120 and 180 min, postprandially. Glycaemic, insulinaemic and appetite hormone responses as well as glycaemic index (GI) and subjective appetite ratings were evaluated. RESULTS: Both enriched breads were characterized as low GI foods (α-CDB:49.7, (HT + α-CD)B:40.0) and presented similar reduction in glucose, insulin and GLP-1 responses. Significant differences were found in glucose values 45 min after (HT + α-CD)B consumption compared to α-CDB (P < 0.05) as well as in serum ghrelin, 120 min postprandially, between (HT + α-CD)B and WB in (- 90.55 ± 29.17 and 16.53 ± 21.78 pg/dL, respectively, P < 0.05). Neither of the enriched breads prevailed regarding the induced self-reported satiety. However, their consumption led to a lower desire for the next meal compared to WB. CONCLUSION: Enrichment of bread with α-CD resulted in positive effects on postprandial glycaemia and induced satiety. Incorporation of encapsulated HT offered similar overall acceptability, due to the bitter taste-masking effect provided by α-CD, and a slightly additional positive effect in postprandial glycaemia and satiety. The development of foods with favorable metabolic effects is of great importance for the prevention of chronic diseases. The study was prospectively registered in clinicaltrials.gov (NCT04725955, date: 27th January 2021).