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Capsaicin (CAP) demonstrates a potential for application in the food and pharmaceutical industries owing to its various attractive health benefits, including anti-cancer, anti-inflammatory, and antioxidant activities. However, the application of CAP is often limited by its low solubility in water, low bioavailability, and strong pungency. In this study, a simple one-step method for the stable encapsulation and dispersion of CAP in aqueous media was developed using polyelectrolyte complex particles formed by chitosan (CHI) and oleic acid (OA). Homogeneous particles with mean diameters below 1 μm were successfully prepared via spontaneous molecular complexation by mixing an aqueous solution of CHI with an ethanolic solution of OA and CAP. CAP was incorporated into the hydrophobic domains of the CHI–OA complex particles through hydrophobic interactions between the alkyl chains of OA and CAP. The factors affecting CAP encapsulation were investigated, and a maximum encapsulation yield of approximately 100% was obtained. The CHI–OA–CAP complex particles could be stored for more than 3 months at room temperature (22–26 °C) without resulting in macroscopic phase separation or degradation of CAP. We believe that our findings provide a useful alternative encapsulation technique for CAP and contribute to expanding its practical application.

Solvent-free preparation types for cyclodextrin complexation, such as co-grinding, are technologies desired by the industry. However, in-depth analytical evaluation of the process and detailed characterization of intermediate states of the complexes are still lacking in areas. In our work, we aimed to apply the co-grinding technology and characterize the process. Fenofibrate was used as a model drug and dimethyl-β-cyclodextrin as a complexation excipient. The physical mixture of the two substances was ground for 60 min; meanwhile, samples were taken. A solvent product of the same composition was also prepared. The intermediate samples and the final products were characterized with instrumental analytical tools. The XRPD measurements showed a decrease in the crystallinity of the drug and the DSC results showed the appearance of a new crystal form. Correlation analysis of FTIR spectra suggests a three-step complexation process. In vitro dissolution studies were performed to compare the dissolution properties of the pure drug to the products. Using a solvent-free production method, we succeeded in producing a two-component system with superior solubility properties compared to both the active ingredient and the product prepared by the solvent method. The intermolecular description of complexation was achieved with a detailed analysis of FTIR spectra.

This chapter focuses on describing the range of chemical-based microencapsulation technologies that have been applied widely within the textile industry, concentrating on specific applications within the dyeing and printing sectors. The chapter reviews the commercially available microencapsulation technologies which are designed to deliver novel visual effects during printing as well as examining the future opportunity for microencapsulation technology in improving textile dyeing processes. Technologies discussed include liposomes, in-situ and interfacial polymerisation as well as molecular complexation methods.

This study expands and combines concepts from two of our earlier studies. One study reported the complementary halogen bonding and π-π charge transfer complexation observed between isomeric electron rich 4-N,N-dimethylaminophenylethynylpyridines and the electron poor halogen bond donor, 1-(3,5-dinitrophenylethynyl)-2,3,5,6-tetrafluoro-4-iodobenzene while the second study elaborated the ditopic halogen bonding of activated pyrimidines. Leveraging our understanding on the combination of these non-covalent interactions, we describe cocrystallization featuring ditopic halogen bonding and π-stacking. Specifically, red cocrystals are formed between the ditopic electron poor halogen bond donor 1-(3,5-dinitrophenylethynyl)-2,4,6-triflouro-3,5-diiodobenzene and each of electron rich pyrimidines 2- and 5-(4-N,N-dimethyl-aminophenylethynyl)pyrimidine. The X-ray single crystal structures of these cocrystals are described in terms of halogen bonding and electron donor-acceptor π-complexation. Computations confirm that the donor-acceptor π-stacking interactions are consistently stronger than the halogen bonding interactions and that there is cooperativity between π-stacking and halogen bonding in the crystals.

The molecular host cucurbit[7]uril forms an extremely stable inclusion complex with the dicationic ferrocene derivative bis(trimethylammoniomethyl)ferrocene in aqueous solution. The equilibrium association constant for this host-guest pair is 3 x 10¹⁵ M⁻¹ (Kd = 3 x 10⁻¹⁶ M), equivalent to that exhibited by the avidin-biotin pair. Although purely synthetic systems with larger association constants have been reported, the present one is unique because it does not rely on polyvalency. Instead, it achieves its extreme affinity by overcoming the compensatory enthalpy-entropy relationship usually observed in supramolecular complexes. Its disproportionately low entropic cost is traced to extensive host desolvation and to the rigidity of both the host and the guest.

Despite numerous research efforts, drug delivery through the oral route remains a major challenge to formulation scientists. The oral delivery of drugs poses a significant challenge because more than 40% of new chemical entities are practically insoluble in water. Low aqueous solubility is the main problem encountered during the formulation development of new actives and for generic development. A complexation approach has been widely investigated to address this issue, which subsequently improves the bioavailability of these drugs. This review discusses the various types of complexes such as metal complex (drug-metal ion), organic molecules (drug-caffeine or drug-hydrophilic polymer), inclusion complex (drug-cyclodextrin), and pharmacosomes (drug-phospholipids) that improves the aqueous solubility, dissolution, and permeability of the drug along with the numerous case studies reported in the literature. Besides improving solubility, drug-complexation provides versatile functions like improving stability, reducing the toxicity of drugs, increasing or decreasing the dissolution rate, and enhancing bioavailability and biodistribution. Apart, various methods to predict the stoichiometric ratio of reactants and the stability of the developed complex are discussed.

Polyelectrolyte complexes based on the electrostatic interactions between the polymers mixed are of increasing importance, therefore, the aim of this study was to develop hydrogels composed of anionic tragacanth gum and cationic chitosan with or without the addition of anionic xanthan gum as carriers for buccal drug delivery. Besides the routine quality tests evaluating the hydrogel’s applicability on the buccal mucosa, different methods directed toward the assessment of the interpolymer complexation process (e.g., turbidity or zeta potential analysis, scanning electron microscopy and Fourier-transform infrared spectroscopy) were employed. The addition of xanthan gum resulted in stronger complexation of chitosan that affected the hydrogel’s characteristics. The formation of a more viscous PEC hydrogel with improved mucoadhesiveness and mechanical strength points out the potential of such polymer combination in the development of buccal drug dosage forms.

Azocalixarenes functionalized with cation binding sites are popular chromoionophores due to the ease of synthesis and the large complexation-induced shifts of their absorption band that originate from an azo-phenol–quinone-hydrazone tautomerism. Despite their extensive use, however, a thorough investigation of the structure of their metal complexes has not been reported. We describe herein the synthesis of a new azocalixarene ligand (2) and the study of its complexation properties with the Ca2+ cation. Through a combination of solution (1H NMR and UV-vis spectroscopies) and solid-state (X-ray diffractometry) techniques, we demonstrate that metal complexation induces a shift of the tautomeric equilibration towards the quinone-hydrazone form, while deprotonation of the complex results in the reversion to the azo-phenol tautomer.