The morphological symmetry-retaining and symmetry-breaking of single crystals of the γ-cyclodextrin metal-organic framework have been achieved via introducing lower symmetric β-cyclodextrins and α-cyclodextrins, respectively. β-cyclodextrins led to a morphological evolution with retained symmetry from cubic to rhombic dodecahedra, while α-cyclodextrins resulted in the original cubic crystal missing a vertex angle presenting symmetry-breaking behavior. The crystal structures of rhombic dodecahedra and angle-deficient crystals were confirmed through X-ray crystallography, and the mechanisms underlying the morphological transformation evolution were further analyzed. Our work not only provides a rare case realizing two different paths of morphological evolution in one system, but also encourages future efforts towards the evolution of artificial crystal systems in a natural way.

BACKGROUND: Vitamin E ( -tocopherol) and cholesterol are crucial components in cellular protection and physiological processes. Their uses in biological media face challenges due to their poor solubility and stability.
OBJECTIVE: The study investigated the complex interactions of these bioactive compounds in various encapsulation systems of cyclodextrin and liposome, as well as dispersion in PEG-6000, in an attempt to improve the viability, motility, and preservation of ovine sperm cells.
METHODS: The work explored the in vitro dissolution kinetics of vitamin E (d-tocopherol) and cholesterol using semi-empirical models.
RESULTS: The release profiles of VitE and Chl varied considerably, depending on the specific carrier systems. For liposome-loaded VitE and Chl, the Korsmeyer-Peppas model gave the best fit; for CD/VitE and CD/Chl, the Higuchi model provided the best fit, whereas for PEG-6000 dispersions (VitE and Chl) both the Higuchi and Korsmeyer-Peppas models demonstrated the excellent fit. All systems indicated a Fickian diffusion mechanism dictated by the concentration gradient. The delivery of VitE and Chl with CD, liposome and PEG dispersion significantly increased sperm mobility and motility. The effect on the VCL parameter was the greatest by liposome-loaded VitE and Chl, followed by CD encapsulation and PEG-6000 dispersion.
CONCLUSIONS: The dynamics of vitamin E and cholesterol within innovative delivery systems offers valuable insights into the development of advanced solutions in reproductive health, particularly on improving the viability, motility of refrigerated ovine sperm cells. Doi.org/10.54680/fr24510110712.

This study evaluates the antiproliferative potential of flavanones, chromanones and their spiro-1-pyrazoline derivatives as well as their inclusion complexes. The main goal was to determine the biological basis of molecular pro-apoptotic activities and the participation of reactive oxygen species (ROS) in shaping the cytotoxic properties of the tested conjugates. For this purpose, changes in mitochondrial potential and the necrotic/apoptotic cell fraction were analyzed. Testing with specific fluorescent probes found that ROS generation had a significant contribution to the biological anticancer activity of complexes of flavanone analogues. TT (thrombin time), PT (prothrombin time) and APTT (activated partial tromboplastin time) were used to evaluate the influence of the compounds on the extrinsic and intrinsic coagulation pathway. Hemolysis assays and microscopy studies were conducted to determine the effect of the compounds on RBCs.

Circularly polarized luminescence (CPL) materials have been widely used in the fields of bioimaging, optoelectronic devices, and optical communications. The supramolecular interaction, involving harnessing non-covalent interactions between host and guest molecules to control their arrangements and assemblies, represents an advanced approach for facilitating the development of CPL materials and finely constructing and tuning the desired CPL properties. Cyclodextrins (CDs) are cyclic natural polysaccharides, which have also been ubiquitous in various fields such as molecular recognition, drug encapsulation, and catalyst separation. By adjusting the interactions between CDs and guest molecules precisely, composite materials with CPL properties can be facilely generated. This review aims to outline the design strategies and performance of CD-based CPL materials comprehensively and provides a detailed illustration of the interactions between host and guest molecules.

Cyclodextrins, commonly used as excipients in antifungal formulations to improve the physicochemical properties and availability of the host molecules, have not been systematically studied for their effects and bioactivity without a complex active substance. This paper evaluates the effects of various cyclodextrins on the physiology of the test organism Candida boidinii. The research examines their impact on yeast growth, viability, biofilm formation and morphological changes. Native ACD, BCD, randomly methylated α- and β-CD and quaternary ammonium α-CD and β-CD were investigated in the 0.5-12.5 mM concentration range in both static and dynamic systems. The study revealed that certain cyclodextrins exhibited notable antifungal effects (up to ~69%) in dynamic systems; however, the biofilm formation was enhanced in static systems. The magnitude of these effects was influenced by several variables, including the size of the internal cavity, the concentration and structure of the cyclodextrins, and the contact time. Furthermore, the study found that CDs exhibited distinct effects in both static and dynamic systems, potentially related to their tendency to form aggregates. The findings suggest that cyclodextrins may have the potential to act as antifungal agents or growth promoters, depending on their structure and surrounding environments.

Cyclodextrin-based polyrotaxanes (CD-PRs) are gaining attention for their dynamic sliding rings along the polymer axis, enabling various applications in molecular shuttles, drug delivery, and durable polymers with slidable cross-links. However, the conventional synthesis of CD-PRs with tunable threading ratios is typically laborious, time-consuming, and complicated, which limits their scalability and cost-effectiveness. Herein, we highlight the great potential of planetary centrifugal mixing, a process that significantly accelerates and simplifies the initial synthesis of polypseudorotaxanes (PPRs), followed by a thiol-ene click reaction as an efficient end-capping reaction for the synthesis of PRs. Notably, PRs synthesized with glutathione (GSH) as the end-capping reagent are in a metastable state, where GSH act as a molecular bumper that significantly prevent de-threading of α-CD rings at room temperature. Moreover, the rate of ring de-threading can be precisely controlled by heating, enabling the preparation of metastable PRs with tunable threading ratios over a wide range. The developed strategy is of great significance to the efficient synthesis of CD-PRs, thus marking a significant step towards their practical application in advanced functional materials and devices.

​Considerable attention has been directed towards cyclodextrins (CDs) in the creation of co-assembled CPL-active materials, owing to their intrinsic chiral host cavities and synergistic host-guest interactions. However, achieving reversed CPL emission regulation with single-handedness CDs moiety poses a significant challenge. In this study, we have devised a series of γ-CD-based host-guest complexes comprising dual pyrene imidazolium derivatives with multiple linkers, which exhibit reversed circularly polarized emission. We have uncovered that the transformation of excimer stacking within γ-CD/pyrene complexes contributes to the inverted CPL emissions originating from a single-handed chiral host. This research elucidates the phenomenom of (+)- and (-)-circularly polarized excimer emission (CPEE) within γ-CD, arising from right- and left-handed stacking conformations, respectively.

BACKGROUND: Cyclodextrins are a well-established system which form inclusion complexes with many guest molecules. This property can be easily exploited to develop drug delivery systems. Additionally, carbon dots (CD) are a low-toxic photoluminescent product which have been used as luminescent tags. The combination of cyclodextrins and carbon dots allows obtaining a new nanoplatform, a biocompatible material, with both capabilities, increasing as well the internalization by the cells of the CD, induced by the cyclodextrins.
RESULTS: In the present work, we have modified the surface of carbon dots obtained from citric acid and glutathione with β and γ cyclodextrins. After a morphological and spectroscopic characterization, we concluded that the luminescence quantum yield and absorption molar coefficient of the derivatized and unmodified carbon dots was the same. These findings, together with the spectroscopic detection of active cyclodextrins, those bond to the CD able to interact with a guest molecule, allowed determination of the ratios: cyclodextrins/CD, active cyclodextrins/CD and an estimation of the CD molecular mass. Furthermore, the biocompatibility of the new materials was evaluated through cytotoxicity and cell-penetrance assays revealing that the materials were non cytotoxic up to 0.1 mg/mL. Moreover, the biocompatible developed nanoplatform penetrates in the cells maintaining the material\'s intrinsic fluorescence, thus constituting an adequate photoluminescent-tag with high-contrast for in vitro cell imaging.
CONCLUSIONS: This work provides a new and easy method to combine cyclodextrins and carbon dots into a biocompatible material which can be used as nanoplatform both as drug delivery system and as photoluminescent tag in cell imaging. Likewise, this paper shows how to characterize the number of cyclodextrins and active cyclodextrins per CD, having an average stoichiometric relation of 1:1 for guest molecule - CD. Additionally, the minimum molecular mass of the unmodified CD was indirectly obtained, yielding about 1.6-1.9 kDa.

The study aimed to develop encapsulation systems to maintain the preservation of everlasting (Helichrysum plicatum) flower extract polyphenols. Spray-dried encapsulates were formulated using β-cyclodextrin (BCD) and 2-hydroxypropyl-β-cyclodextrin (HPBCD) as supramolecular hosts, and their macromolecule mixtures with the conventional carriers, maltodextrin (MD) and whey protein (WP). The obtained microparticles were comparatively assessed regarding technological, physicochemical, and phytochemical properties. The highest yields were achieved by combining cyclodextrins with whey protein (73.96% for WP+BCD and 75.50% for WP+HPBCD compared to 62.48% of pure extract). The extract-carrier interactions and thermal stability were evaluated by FTIR and DSC analysis, suggesting successful entrapment within the carriers. Carriers reduced the particle diameter (3.99 to 4.86 μm compared to 6.49 μm of pure extract), classifying all encapsulates as microsystems. Carrier blends made the particle size distribution uniform, while SEM analysis revealed the production of more spherical and less aggregated particles. The HPBCD provided the highest encapsulation efficiency, with the highest content of detected aglycones and slightly lower values of their glycosylated forms. An analysis of the dual macromolecule encapsulation systems revealed the highest bioactive preservation potential for SHE+MD+BCD and SHE+WP+HPBCD. Overall, macromolecule combinations of cyclodextrins and conventional biopolymers in the spray-drying process can enhance the functional properties of H. plicatum extract.

With increasing longevity globally, the search for effective and patient-friendly anti-aging solutions has been growing. Retinoic acid (Ret) is an FDA-approved anti-aging and anti-wrinkling formula, however, its poor solubility and poor tolerability hamper its use in cosmetically accepted formulations. In this study, cyclodextrins and arginine were investigated for improving the solubility and tolerability of retinoic acid through the formation of inclusion complexes and salt formation, respectively. Two different methods were employed: physical mixing and kneading. The prepared dispersions were investigated for molecular docking (MD), solubility, thermal and spectral analyses, cytotoxicity, and scratch assays. The optimized disperse systems were formulated in a gel formulation and characterized for rheological, in vitro release, and kinetics. The MD, DSC, and FTIR results indicated that both β- and hydroxy propyl (HP) β-cyclodextrins could host RA in their cavities and form inclusion complexes. Ret can form a salt with the basic amino acid arginine. Solubility studies of RA significantly (p < 0.01) enhanced by 14- to 81-fold increases with the investigated cyclodextrins and arginine. The cell viability recorded for Ret:HP β-CD K and Ret:arginine K was significantly increased compared to that for Ret alone. The IC50% recorded for azelaic acid (mild to non-irritant control), Ret, Ret:HP β-CD K, and Ret:arginine K were 1000, 485, 1100, and 895 µg/mL, respectively. The two carriers (HP β-CD and the amino acid arginine) were able to significantly (p < 0.05) reduce the irritation potential of Ret. Furthermore, comparable gap closure rates were recorded for Ret alone, Ret:HP β-CD K, and Ret:arginine K, indicating that inclusion complexation and ion pair formation reduced the irritation potentials without undermining the efficacy.