Synthesis and Characterization of the Inclusion Complex of Dicationic Ionic Liquid and β-Cyclodextrin

The supramolecular structure of the inclusion complex of β-cyclodextrin (β-CD) with 1,1',2,2'-tetramethyl-3,3'-(p-phenylenedimethylene) diimidazolium dibromide (TetraPhimBr), a dicationic ionic liquid, has been investigated. The inclusion complex with 1:1 molar ratio was prepared by a kneading method. Fourier transform infrared spectroscopy (FTIR), powder X-ray diffraction (XRD) analysis, (1)H NMR and thermogravimetric analysis (TGA) confirmed the formation of the inclusion complex. The results showed that the host-guest system is a fine crystalline powder. The decomposition temperature of the inclusion complex is lower than that of its parent molecules, TetraPhimBr and β-CD individually.     

Inclusion Complex of Sea Buckthorn Fruit Oil with β-Cyclodextrin: Preparation Characterization and Antioxidant Activity

This study aims to produce an inclusion complex between β-cyclodextrin (β-CD) and sea buckthorn fruit oil (SBFO) by using the saturated aqueous solution method and then to compare the resultant solution with the crude mixtures. In this study, the SBFO is extracted by Soxhlet extraction, which is optimized through the single-factor test. The main constituent of the SBFO is identified by gas chromatography-mass spectrometry (GC-MS), which confirms eight fatty acids. Fourier transform infrared spectroscopy, thermogravimetric analysis-differential scanning calorimetry, optical microscopy, scanning electron microscopy, and the result-characterized synthesized compounds confirm the formation of stable inclusion compounds by the SBFO with β-CD. The yield values of the inclusion complex and the SBFO loading content are 64.87 ± 2.26% and 9.2 ± 1.58%, respectively. Comparing the crude fruit oil, β-CD–SBFO, and saponified fruit oil reveals differences in their 2,2-diphenyl-1-pycrylhydrazyl and 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonate) antioxidant activities. These findings suggest that the SBFO inclusion complex after β-cyclodextrin is stabilized and is a good antioxidant. This solution improves the inadequacy of the water solution and the instability of the SBFO. This study also implies that β-CD is a cost-effective and straightforward carrier for extending the applications of SBFO as a food or medicinal additive. Practical applications: In this experiment, the SBFO is converted from oil to powder to increase its efficacy as an additive to health and food products.     

Simple Determination of Deoxycholic and Ursodeoxycholic Acids by Phenolphthalein-β-Cyclodextrin Inclusion Complex

An expeditious colorimetric methodology for the determination of the deoxycholic acid (DCA) and of the ursodeoxycholic acid (UDCA) in pharmaceutical formulations is reported. The method is based on their competitive complexation reaction with a color indicator to form β-cyclodextrin-inclusion complexes. Several pH color indicators were tested, but phenolphthalein (PHP) showed the best interaction with the β-cyclodextrin (β-CD) with an inclusion yield higher than 95%. The best concentrations of β-cyclodextrin to form inclusion complexes were 1.24 × 10⁻³ and 6.2 × 10⁻⁴ M at pH 9.5 and 10.5. Statistical analysis of the results showed that the pH had a significant effect on the DCA determination and that high β-CD-PHP inclusion complex concentrations had a significant negative effect on the UDCA determination (p < 0.05). The limit of detection and limit of quantification were 3.94 × 10⁻⁵ and 1.31 × 10⁻⁴ M for DCA (range: 6.1 × 10⁻⁶–3.13 × 10⁻³ M), 4.08 × 10⁻⁵  and 1.36 × 10⁻⁴ M for UDCA (range: 6.05 × 10⁻⁶–3.88 × 10⁻⁴ M). This simple and cheap method showed high stability and feasible instrumentation.     

Evaluation of Physicochemical and Antifungal Properties of Polylactic Acid–Thermoplastic Starch–Chitosan Biocomposites

Biocomposites of polylactic acid, thermoplastic starch, chitosan powder, and chitosan lyophilized powder were prepared using an extrusion process. The color, thermal, structural, mechanical, morphology, and antimicrobial properties were evaluated. The addition of thermoplastic starch and chitosan (chitosan powder and chitosan lyophilized powder) produced significant changes in color and heterogeneous surface morphology of the polylactic acid biocomposites. The thermal, mechanical, and morphometric properties of the material showed changes with the addition of thermoplastic starch and chitosan (chitosan powder and chitosan lyophilized powder). The biocomposites formulated with chitosan powder and chitosan lyophilized powder showed antifungal activity when evaluating this property. The biocomposites produced could be used in packaging applications.     

Physicochemical Properties and Metallurgical Evaluation of Magnesium—Strontium-Containing Limestones

Theoretical Foundations of Chemical Engineering - Magnesium—strontium-containing limestones are overburden and lie together with celestite ore, the extraction of which is economically...     

Synthesis and Characterization of the Inclusion Complex of β-cyclodextrin and Azomethine

A β-cyclodextrin (β-Cyd) inclusion complex containing azomethine as a guest was prepared by kneading method with aliquot addition of ethanol. The product was characterized by Fourier Transform Infrared (FTIR) spectrometer, ¹H Nuclear Magnetic Resonance (¹H NMR) and Thermogravimetric Analyzer (TGA), which proves the formation of the inclusion complex where the benzyl part of azomethine has been encapsulated by the hydrophobic cavity of β-Cyd. The interaction of β-Cyd and azomethine was also analyzed by means of spectrometry by UV-Vis spectrophotometer to determine the formation constant. The formation constant was calculated by using a modified Benesi-Hildebrand equation at 25 °C. The apparent formation constant obtained was 1.29 × 10⁴ L/mol. Besides that, the stoichiometry ratio was also determined to be 1:1 for the inclusion complex of β-Cyd with azomethine.     

Effect of γ-Cyclodextrin Inclusion Complex on the Absorption of R-α-Lipoic Acid in Rats

R-α-lipoic acid (RLA) is an endogenous organic acid, and works as a cofactor for mitochondrial enzymes and as a kind of antioxidant. Inclusion complexes of RLA with α-, β- or γ-cyclodextrins (CD) were prepared and orally administered as a suspension to rats. Among them, RLA/γ-CD showed the highest plasma exposure, and its area under the plasma concentration-time curve (AUC) of RLA was 2.2 times higher than that after oral administration of non-inclusion RLA. On the other hand, the AUC after oral administration of non-inclusion RLA and RLA/γ-CD to pylorus-ligated rats did not differ. However, the AUC after intraduodenal administration of RLA/γ-CD was 5.1 times higher than that of non-inclusion RLA, and was almost comparable to the AUC after intraduodenal administration of RLA-Na solution. Furthermore, the AUC after intraduodenal administration of RLA/γ-CD was not affected by biliary ligation or co-administration of an amylase inhibitor. These findings demonstrated that RLA was absorbed from the small intestine effectively when orally administered as a γ-CD inclusion complex, which could be easily dissolved in the lumen of the intestine. In conclusion, γ-CD inclusion complex is an appropriate formulation for supplying RLA as a drug or nutritional supplement with respect to absorption.     

Formation of a Polymer-Coated Inclusion Complex of D-Limonene and β-Cyclodextrin by Spray Drying

The polymer-coated inclusion complex powder formation of D-limonene and β-cyclodextrin obtained by spray drying was investigated with respect to the effects of various types of polymer coating agents on the powder particle size and morphology. The addition of the polymer coating agent affected the average particle size, morphology, and internal structures of the spray-dried powders. The average particle diameter of the uncoated spray-dried powders was approximately 5 µm. The powder particle size increased upon the addition of a polymer coating reagent. With the addition of 9 wt% of the polymer coating agent, an average diameter of approximately 80 µm was obtained for the spray-dried powder particles. However, further addition showed a negligible effect on the particle size. Inclusion complex crystals were observed on the surface and inside of the powder particles.     

Physicochemical Properties of Lipase-Catalyzed Interesterified Fat Containing α-Linolenic Acid

Two substrate blends (8:6:6 and 6:6:9, by weight) of anhydrous butterfat (ABF), palm stearin (PS), and flaxseed oil (FSO) were interesterified by immobilized lipases. The reaction was carried out in the absence of solvent at 60 °C for 24 h in a 1-L tank stirred-batch type reactor. In terms of equivalent carbon number (ECN) of triacylglycerol (TAG), the areas of ECN 36-38 (from FSO) and ECN 48-50 (from PS) decreased during the interesterification while ECN 42–46 increased with increasing reaction time. As interesterification time increased, the decreased enthalpy (?H), peak temperature (T _P) and transition range were observed. After short path distillation, interesterified fat (IF) was produced in which α-linolenic acid contents (ALn, mol%) of the 8:6:6 and 6:6:9 IF were 15.7 and 21.7%, respectively. Tocopherol, cholesterol and phytosterol contents in each IF were significantly reduced after short path distillation. In this study, hardness of 6:6:9 IF and 8:6:6 IF were 217 and 800 g/cm², respectively. After interesterification, short spacing at 4.6 Å disappeared or weakened, indicating that the predominant polymorphic form had changed from the β form to the desirable crystalline structure of the β′ form.     

Biosurfactant Production by Bacillus tequilensis ZSB10: Structural Characterization,Physicochemical, and Antifungal Properties

A new biosurfactant was obtained from a moderately halophilic bacterium identified as Bacillus tequilensis ZSB10 that was isolated from a saline water pond located in Tehuacan-Cuicatlan valley, Mexico. A kinetic analysis of the bacterial growth of the ZSB10 strain showed a maximum growth at 24 h regardless of the initial pH (5, 7.4, and 9). The best results were found at pH = 7.4 in terms of bacterial growth, besides which the produced biosurfactant showed emulsifying and surfactant properties with an emulsification index (E₂₄) and surface tension change (ΔST) of 54 ± 0% and 26 mN m⁻¹, respectively. Extracted ZSB10 crude biosurfactant had a yield of 106 ± 6 mg L⁻¹, an E₂₄ = 58.4 ± 0.2%, and a ΔST = 26 mN m⁻¹ with a critical micelle concentration (CMC) of 44.82 mg L⁻¹. Also, its structure was characterized by MALDI-TOF mass spectrometry as a surfactin, iturin A, and fengycin mixture whose main isoform was leu/ile-7 C₁₅ surfactin [M + Na]⁺. Finally, the ZSB10 crude biosurfactant showed antifungal activity against Helminthosporium sp., with a 79.3% growth inhibition and an IC₅₀ of 1.37 mg per disc. Therefore, this biosurfactant could be used as biopesticide.     

Synthesis and Properties of Lipoamino Acid–Fatty Acid Mixtures: Influence of the Amphiphilic Structure

The acylation of amino acids by acid chlorides with from 8 to 12 carbon atoms in alkaline aqueous medium following Schotten–Baumann reaction results in sodium salts of a N ^α-acylamino acid and fatty acid mixture. The latter are present in a proportion from 40 to 60%. These compositions represent mixtures of amphiphilic anionic surfactants. Together they contribute to the properties of the formulation. Measurements of the surface-active properties of these formulations, such as critical micelle concentration (CMC), surface tension at the CMC (ST), foaming capacity (FC) and foaming stability (FS), show that surfactant mixtures with the longest chain have the most desirable properties. They are comparable to commercial petroleum-based surfactants. Thus, the CMC, ST and CM values of the formulation obtained starting from leucine and dodecanoyl chloride (310 mg/l, 30.1 mN/m and 200%, respectively) are similar to, and even better than, sodium dodecylsulfate (290 mg/l, 39.1 mN/m and 230%, respectively).     

Synthesis of Functionalized δ-Hydroxy-β-keto Esters and Evaluation of Their Anti-inflammatory Properties

δ-Hydroxy-β-keto esters and δ,β-dihydroxy esters are characteristic structural motifs of statin-type natural products and drug candidates. Here, we describe the synthesis of functionalized δ-hydroxy-β-keto esters in good yields and excellent enantioselectivities using Chan's diene and modified Mukaiyama-aldol reaction conditions. Diastereoselective reduction of δ,β-dihydroxy esters afforded the respective syn- and anti-diols, and saponification yielded the corresponding acids. All products were evaluated for their anti-inflammatory properties, which uncovered a surprising structure-activity relationship.     

Preparation and Performance of Poly(Lactic Acid)-γ-Cyclodextrin Inclusion Complex-Poly(Lactic Acid) Multibranched Polymers by the Reactive Extrusion Process

The poly(lactic acid)-γ-cyclodextrin inclusion complex-poly(lactic acid) multibranched polymers were prepared by reactive extrusion process with L-lactide as raw material, stannous octoate as catalyst and the carboxyl poly(lactic acid)-γ-cyclodextrin inclusion compound as cores prepared by ultrasonic coprecipitation and carboxylation reaction. It was shown that the comprehensive performance of poly(lactic acid)-γ-cyclodextrin inclusion complex-poly(lactic acid) had been significantly improved compared with liner poly(lactic acid) by the study of structure and properties. Thus, the novel poly(lactic acid)-γ-cyclodextrin inclusion complex-poly(lactic acid) multibranched polymers have a potential use in biomedical materials. This study provided a simple and feasible preparation method for improving the performance of poly(lactic acid).     

Preparation and Characterization of Carboxymethyl Chitosan and β-Cyclodextrin Microspheres by Spray Drying

Three kinds of carboxymethyl chitosan/β-cyclodextrin microspheres loaded with theophylline were prepared by spray drying intended for pulmonary delivery. Mucociliotoxicity, permeation rate, and drug release characteristics of the product were investigated. The microspheres obtained by spray drying were found to be spherical with smooth or wrinkled surfaces. The mean particle size was between 3.39 and 6.06 µm. The microspheres demonstrated high product yield (43.7–50.2%), high drug loading (13.7–38.1%), and high encapsulation efficiency (86.9–92.8%). FT-IR indicated that there were interactions of theophylline with carboxymethyl chitosan matrix. Further studies on mucociliotoxicity and permeation confirmed that microspheres had better adaptability and high permeation rate. In vitro drug release from the microspheres was not related to the drug/polymer ratios.     

Experimental and Theoretical Investigations on the Supermolecular Structure of Isoliquiritigenin and 6-O-α-d-Maltosyl-β-cyclodextrin Inclusion Complex

Isoliquiritigenin (ILTG) possesses many pharmacological properties. However, its poor solubility and stability in water hinders its wide applications. The solubility of bioactive compounds can often be enhanced through preparation and delivery of various cyclodextrin (CD) inclusion complexes. The 6-O-α-d-maltosyl-β-CD (G₂-β-CD), as one of the newest developments of CDs, has high aqueous solubility and low toxicity, especially stable inclusion characteristics with bioactive compounds. In this work, we for the first time construct and characterize the supermolecular structure of ILTG/G₂-β-CD by scanning electron microscopy (SEM), ultraviolet-visible spectroscopy (UV), Fourier transform infrared spectroscopy (FT-IR), and X-ray diffractometry (XRD). The solubility of ILTG in water at 25 °C rises from 0.003 to 0.717 mg/mL by the encapsulation with G₂-β-CD. Our experimental observations on the presence of the ILTG/G₂-β-CD inclusion complex are further supported by the ONIOM(our Own N-layer Integrated Orbital molecular Mechanics)-based QM/MM (Quantum Mechanics/Molecular Mechanics) calculations, typically substantiating these supermolecular characteristics, such as detailed structural assignments, preferred binding orientations, selectivity, solvent effects, interaction energies and forces of the ILTG/G₂-β-CD inclusion complex. Our results have elucidated how ILTG interacts with G₂-β-CD, demonstrating the primary host-guest interactions between ILTG and G₂-β-CD, characterized by hydrogen bonds, hydrophobic interactions, electrostatic forces, and conformational effects, are favored for the formation of the ILTG/G₂-β-CD inclusion.     

Effect of Saturated/Unsaturated Fatty Acid Ratio on Physicochemical Properties of Palm Olein–Olive Oil Blend

Although blending polyunsaturated oil with more saturated or monounsaturated oils has been studied extensively, there is no similar information regarding the partial replacement of palm olein with olive oil (OO). Therefore the main objective of this study was to investigate the effects of OO partial replacement (0, 25, 50, 75, 90 and 100% w/w) on the chemical stability of palm olein oil (POO). The physicochemical properties of oil samples namely iodine value, peroxide value (PV), anisidine value, TOTOX value (total oxidation value, TV), free fatty acid (FFA), cloud point, color and viscosity were considered as response variables. Significant differences among the oil blend properties were determined at the significance level of P < 0.05. Apart from FFA, all the response variables were significantly influenced by type and concentration of oils. The oil blend containing 10% POO and 90% OO showed the highest TV (6.10); whereas the blend containing 90% POO and 10% OO exhibited the least TV (2.41). This study indicated that the chemical stability of oil blend significantly (P < 0.05) increased with increasing the proportion of polyunsaturated/monounsaturated fatty acid.     

β-Cyclodextrin Encapsulation of Synthetic AHLs: Drug Delivery Implications and Quorum-Quenching Exploits

Many bacteria, such as Pseudomonas aeruginosa, regulate phenotypic switching in a population density-dependent manner through a phenomenon known as quorum sensing (QS). For Gram-negative bacteria, QS relies on the synthesis, transmission, and perception of low-molecular-weight signal molecules that are predominantly N-acyl-l -homoserine lactones (AHLs). Efforts to disrupt AHL-mediated QS have largely focused on the development of synthetic AHL analogues (SAHLAs) that are structurally similar to native AHLs. However, like AHLs, these molecules tend to be hydrophobic and are poorly soluble under aqueous conditions. Water-soluble macrocycles, such as cyclodextrins (CDs), that encapsulate hydrophobic guests have long been used by both the agricultural and pharmaceutical industries to overcome the solubility issues associated with hydrophobic compounds of interest. Conveniently, CDs have also demonstrated anti-AHL-mediated QS effects. Here, using fluorescence spectroscopy, NMR spectrometry, and mass spectrometry, we evaluate the affinity of SAHLAs, as well as their hydrolysis products, for β-CD inclusion. We also evaluated the ability of these complexes to inhibit wild-type P. aeruginosa virulence in a Caenorhabditis elegans host infection study, for the first time. Our efforts confirm the potential of β-CDs for the improved delivery of SAHLAs at the host/microbial interface, expanding the utility of this approach as a strategy for probing and controlling QS.     

Use of Furandicarboxylic Acid and Its Decyl Ester as Additives in the Fischer’s Glycosylation of Decanol by d-Glucose: Physicochemical Properties of the Surfactant Compositions Obtained

2,5-Furandicarboxylic acid is a promising bio-based platform chemical that may serve as a ‘green’ substitute for terephthalate in polyesters. In the present work, straightforward glycosylation of decanol with unprotected and non-activated d-glucose was performed under reduced quantities of sulfuric acid as catalyst (down to 0.9 mol%) in the presence of 2,5-furandicarboxylic acid or its n-decyl ester as additive. Yield of decyl monoglucosides was highly improved by the use of the additives. Moreover, the presence of additive also limited the colouration of the reaction. The physical and chemical properties of the surfactant composition produced were studied and compared to reference compositions. The ultimate biodegradability of furan-2,5-dicarboxylic acid (FDCA) and its n-decyl ester formed or produced in the bulk reaction medium was also studied in order to assess its potential use in surfactant industry.     

Is Dialdehyde Chitosan a Good Substance to Modify Physicochemical Properties of Biopolymeric Materials?

The aim of this work was to compare physicochemical properties of three dimensional scaffolds based on silk fibroin, collagen and chitosan blends, cross-linked with dialdehyde starch (DAS) and dialdehyde chitosan (DAC). DAS was commercially available, while DAC was obtained by one-step synthesis. Structure and physicochemical properties of the materials were characterized using Fourier transfer infrared spectroscopy with attenuated total reflectance device (FTIR-ATR), swelling behavior and water content measurements, porosity and density observations, scanning electron microscopy imaging (SEM), mechanical properties evaluation and thermogravimetric analysis. Metabolic activity with AlamarBlue assay and live/dead fluorescence staining were performed to evaluate the cytocompatibility of the obtained materials with MG-63 osteoblast-like cells. The results showed that the properties of the scaffolds based on silk fibroin, collagen and chitosan can be modified by chemical cross-linking with DAS and DAC. It was found that DAS and DAC have different influence on the properties of biopolymeric scaffolds. Materials cross-linked with DAS were characterized by higher swelling ability (~4000% for DAS cross-linked materials; ~2500% for DAC cross-linked materials), they had lower density (Coll/CTS/30SF scaffold cross-linked with DAS: 21.8 ± 2.4 g/cm³; cross-linked with DAC: 14.6 ± 0.7 g/cm³) and lower mechanical properties (maximum deformation for DAC cross-linked scaffolds was about 69%; for DAS cross-linked scaffolds it was in the range of 12.67 ± 1.51% and 19.83 ± 1.30%) in comparison to materials cross-linked with DAC. Additionally, scaffolds cross-linked with DAS exhibited higher biocompatibility than those cross-linked with DAC. However, the obtained results showed that both types of scaffolds can provide the support required in regenerative medicine and tissue engineering. The scaffolds presented in the present work can be potentially used in bone tissue engineering to facilitate healing of small bone defects.