Ionic liquids (ILs) are chemical compounds composed of ions with melting points below 100 °C exhibiting a design feature. ILs are commonly used as the so-called green solvents, reagents or highly efficient catalysts in varied chemical processes. The huge application potential of ionic liquids (IL) justifies the growing interest in these compounds. In the last decade, increasing attention has been devoted to the development of new methods in the synthesis of stable chiral ionic liquids (CILs) and their application in various separation techniques. The beginnings of the successful use of CILs to separate enantiomers date back to the 1990 s. Most chiral ILs are based on chiral cations or chiral anions. There is also a limited number of CILs possessing both a chiral cation and a chiral anion. Due to the high molecular diversity of both ions, of which at least one has a chiral center, we have the possibility to design a large variety of optically active structures, thus expanding the range of CIL applications. Research utilizing chiral ionic liquids only recently has become more popular. However, it is the area that still has great potential for future development. This review aimed to describe the diversity of structures, properties and examples of applications of chiral ionic liquids as new chiral solid materials and chiral components of the anisotropic environment, providing chiral recognition of enantiomeric analytes, which is useful in liquid chromatography, countercurrent chromatography and other various CIL-based extraction techniques including aqueous biphasic (ABS) extraction systems, solid–liquid two-phase systems, liquid–liquid extraction systems with hydrophilic CILs, liquid–liquid extraction systems with hydrophobic CILs, solid-phase extraction and induced-precipitation techniques developed in the recent years. The growing demand for pure enantiomers in the pharmaceutical and food industries sparks further development in the field of extraction and separation systems modified with CILs highlighting them as affordable and environmentally friendly both chiral selectors and solvents.
Trace elements play an important role in the pathogenesis of several serious ophthalmological disorders, such as glaucoma, age-related macular degeneration (AMD), diabetic retinopathy, cataract, etc. This study aimed to measure alterations of chemical elements’ (67) levels in the aqueous humor of patients undergoing cataract surgery. The pilot study included 115 patients, (age 74 ± 7.27, female 64.35%, male 35.65%). The aqueous levels of elements were measured by the use of the inductively coupled plasma optical emission spectrometry (ICP-OES), quality controlled with certified standards. The classification of elements based on their concentration was achieved by hierarchical cluster analysis. This is the first screening study that quantifies over 60 elements which are present in the fluid from the anterior chamber of the eye of cataract patients. The obtained results can be suitable for understanding and identifying the causes that may play a role in the initiation and progression of lens opacity.
The aim of the study was to estimate the thiocyanate levels in saliva of cigarette smokers in comparison to e-cigarette smokers and nonsmokers. To improve our understanding of the influence of smoking on the oral level of thiocyanate, we conducted an assessment of human saliva, in 24 individuals (eight tobacco smokers, eight e-cigarette smokers, and eight nonsmokers). High-Performance Liquid Chromatography with ultraviolet detection (HPLC-UV) using a unique phosphatidylcholine column was applied in this assay. Thiocyanate ion was detected directly by its absorbance at 210 nm. The method presents a new application of the IAM (Immobilized Artificial Membrane) column for quantification of inorganic anions. The whole process meets the criteria of green chemistry because it was carried out without the use of organic solvents. For compensating matrix effects, an eight-point standard addition protocol was used to quantify the thiocyanate level in saliva samples. The calibration graphs were linear in the range of 5–100 mg L−1 with a correlation coefficient higher than 0.99. The thiocyanate concentrations in the saliva of tobacco smokers, e-cigarette smokers, and nonsmokers were found in the range of 121.25–187.54 mg L−1, 121.24–244.11 mg L−1, 33.03–79.49 mg L−1, respectively. The present study indicates an obvious statistically significant elevation in salivary thiocyanate level in tobacco smokers in comparison to nonsmokers. The phosphatidylcholine-based stationary phase proved to be suitable for the detection and quantification of the thiocyanate ion. The salivary thiocyanate levels in e-cigarette smokers were not significantly different in comparison to tobacco smokers but higher if compared to nonsmokers. The criterion for statistical significance was p < 0.05.
We present the specific cooperative effect of a semisynthetic glycopeptide antibiotic teicoplanin and chiral ionic liquids containing the (1R,2S,5R)-(-)-menthol moiety on the chiral recognition of enantiomers of mandelic acid, vanilmandelic acid, and phenyllactic acid. Experiments were performed chromatographically on an Astec Chirobiotic T chiral stationary phase applying the mobile phase with the addition of the chiral ionic liquids. The stereoselective binding of enantiomers to teicoplanin in presence of new chiral ionic liquids were evaluated applying thermodynamic measurements and the docking simulations. Both the experimental and theoretical methods revealed that the chiral recognition of enantiomers in the presence of new chiral ionic liquids was enthalpy driven. The changes of the teicoplanin conformation occurring upon binding of the chiral ionic liquids are responsible for the differences in the standard changes in Gibbs energy (ΔG ) values obtained for complexes formed by the R and S enantiomers and teicoplanin. Docking simulations revealed the steric adjustment between the chiral ionic liquids cyclohexane ring (chair conformation) and the β-d-glucosamine ring of teicoplanin and additionally hydrophobic interactions between the decanoic aliphatic chain of teicoplanin and the alkyl group of the tested salts. The obtained terpene derivatives can be considered as "structural task-specific ionic liquids" responsible for enhancing the chiral resolution in synergistic systems with two chiral selectors.
Reversed-phase high-performance liquid chromatography assay with the diode array detector was applied for detection of trans-resveratrol complexes with copper (II). Two complexes with copper to resveratrol ratio 3:2 and 1:1 were identified in ethanolic-aqueous solutions in neutral and acidic conditions. The matrix-assisted laser desorption ionization-time of flight mass spectrometry was used for evaluation of complexes in eluate liquid fraction. The structures of complexes were modeled by Titan, Spartan and HyperChem software. The findings obtained satisfactorily explain the chromatographic data and could provide useful an additional data about these forms in which is present trans-resveratrol in wine (free and/or forming complex with copper).
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