An amphiphilic γ-cyclodextrin derivative bearing a single methyl-oleate-derived C18 chain (MO γ-CD) was synthesised by epoxide ring opening under ball-milling conditions and investigated as a self-assembling macrocyclic platform for ibuprofen solubilization and release modulation. The derivative was characterised by ESI-MS and NMR, and its aqueous behaviour was evaluated by solubility studies, dynamic light scattering and surface tension measurements. MO γ-CD retained sufficient aqueous compatibility, reaching an apparent solubility of approximately 3.5 mg/mL at 25 °C, and showed concentration-dependent self-association with critical aggregation concentration values of approximately 0.15–0.20 mM. The resulting assemblies displayed a stable volume-weighted size distribution of approximately 58 nm over 23 days. Ibuprofen, selected as a poorly water-soluble model drug, was not significantly solubilised below the aggregation concentration, whereas MO γ-CD markedly increased its apparent aqueous solubility above this threshold, reaching approximately 1.5–2.5 mg/mL depending on the loading procedure and equilibration time. In vitro release studies showed pH-dependent behaviour: MO γ-CD assemblies enhanced ibuprofen release under acidic conditions, while providing a more gradual release at pH 7.4 compared with the drug suspension. Preliminary cytotoxicity studies on Caco-2 cells indicated acceptable short-term biocompatibility, with concentration- and time-dependent effects at the highest tested concentration. Overall, these findings support MO γ-CD as an amphiphilic γ-cyclodextrin scaffold able to combine supramolecular self-assembly, drug solubilization and release modulation. An amphiphilic γ-cyclodextrin derivative bearing a single methyl-oleate-derived C18 chain was synthesised and characterised. MO γ-CD showed concentration-dependent self-association with a critical aggregation concentration of approximately 0.15–0.20 mM. MO γ-CD supramolecular assemblies markedly enhanced the apparent aqueous solubility of ibuprofen above the aggregation threshold. The IBU-loaded assemblies displayed pH-dependent release, improving release under acidic conditions and modulating release at pH 7.4.
Thymol is a natural source compound which widely distributed in some species and plant, and exhibited numerous biological activities. Inflammation and stomach ulcer are common diseases that affects many people worldwide. The objective of this work is to prepare thymol-β-cyclodextrin nansponge formulation and study its anti-inflammatory and anti-ulcer activity in rats. Three formulations (T1-T3) were prepared and evaluated for encapsulation efficiency (
The temperature-dependent thermodynamics of supramolecular complexation between butylscopolamine bromide (BSB) and native (α-, β-, and γ-cyclodextrins) and substituted β-cyclodextrins were investigated by isothermal titration calorimetry (ITC). Among the native CDs only β-CD exhibit a measurable heat flow, with a 1:1 stoichiometry, with binding predominantly entropic driven. The CMβ-CD: BSB system showed the strongest enthalpic stabilization, comparing all investigated systems, and a negative heat capacity change (ΔCp < 0), consistent with cavity dehydration and reduction of solvent-exposed nonpolar surface area upon inclusion. The enhanced affinity observed for CMβ-CD relative to neutral derivatives (native or substituted ones) indicates cooperative contributions from hydrophobic inclusion and electrostatic attraction between the cationic guest and anionic substituents. Linear correlation between ΔH° and TΔS° revealed near complete enthalpy-entropy compensation, leading to weak temperature dependence of ΔG°. The compensation behavior, supported by consistent stoichiometry and coherent ΔCp values, suggests intrinsic solvent mediated thermodynamic coupling. Overall, the results provide a comprehensive calorimetric description of BSB recognition by modified CDs and clarify how substituent chemistry modulates the balance between enthalpic stabilization and entropic penalty in aqueous supramolecular systems.
A novel bis-(nitrogen-heterocyclic carbene, NHC) derivatives, 1,4-bis[1-(quinolin-8-yl)-imidazolium-3-yl)]-benzene bis-hexafluorophosphate (2) was synthesized and characterized by using 1H NMR, 13C NMR, ESI-MS, and single-crystal X-ray diffraction technique. X-ray single crystal diffraction analysis shows that the bis-NHC probe 2 crystallizes in the triclinic space group P-1, and p-xylyl bridged two independent NHC moieties adopting an outward expansion in the endo-conformation, which were further connected by stronger π-π interactions between two quinoline rings of the adjacent bis-NHC molecules in face-to-face parallel arrangement. The bis-NHC probe 2 was demonstrated as a highly selective and sensitive fluorescent chemo-sensor molecule for Al3+ ion in aqueous-organic media, exhibiting a distinctly red-shifted fluorescence enhancement. A 1:1 binding ratio of bis-quinoline-Al [2 + 2] metallo-macrocyclic supramolecular assemblies and strong supramolecular interaction between Al3+ ion and both the carbonic hydrogen and quinoline nitrogen, were suggested by Job’s plot analysis and 1HNMR spectroscopy titrations. The detection limit for Al3+ ion was calculated to be 0.13 µM. Practical evaluation using tap water samples demonstrated the potential of bis-NHC probe 2 for Al3+ ion detection in complicated environments.
Dopamine (DA) inclusion complexes were prepared with β-cyclodextrin (β-CD), hydroxypropyl-β-CD (HP-β-CD) and methyl-β-CD (Me-β-CD) to develop sustained-release nanosystems. This study provides a systematic experimental and in silico evaluation of DA–CD interactions, linking complex stoichiometry and physicochemical properties to the development of sustained-release DA nanocarriers. β-CD exhibited the highest performance, forming predominantly 1:2 host-guest complexes (β-CD: DA), with inclusion efficiency 59
