Thermodynamic study of new antiepileptic compounds by combining chromatography on the phosphatidylcholine biomimetic stationary phase and differential scanning calorimetry

Flieger, Jolanta; Trębacz, Hanna; Pizoń, Magdalena; Płazińska, Anita; Płaziński, Wojciech; Kowalska, Anna; Szczęsna, Agnieszka; Plech, Tomasz

doi:10.1002/jssc.201900248

Cited by 9 publications

(8 citation statements)

References 57 publications

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“…This HPLC column has been designed for the prediction of drug-membrane interactions. There is evidence that the retention measured on this column correlates to traditional in-vitro methods such as Caco-2 cell line cultures, intestinal tissue, or liposome assays [34,35,36]. However, it has been previously discovered that inorganic anions are also able to retain on a phospholipid monolayer by Hu et al [37].…”

Section: Introductionmentioning

confidence: 99%

Levels of the Thiocyanate in the Saliva of Tobacco Smokers in Comparison to e-Cigarette Smokers and Nonsmokers Measured by HPLC on a Phosphatidylcholine Column

Flieger

Kawka

Tatarczak-Michalewska

2019

Molecules

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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.

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Section: Introductionmentioning

confidence: 99%

Levels of the Thiocyanate in the Saliva of Tobacco Smokers in Comparison to e-Cigarette Smokers and Nonsmokers Measured by HPLC on a Phosphatidylcholine Column

Flieger

Kawka

Tatarczak-Michalewska

2019

Molecules

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“…However, the studies showed that the membrane partition measured by IAM chromatography could provide a more reliable assessment, especially when the compounds are charged. The thermodynamic aspects of the binding of new antiepileptic compounds to C‐18 and IAM stationary phases have been investigated and compared using differential scanning calorimetry 53 . It was found that heteroatoms such as oxygen and sulphur in the triazole ring were responsible for the selectivity differences in the IAM interactions supported by molecular dynamics calculations.…”

Section: New Applications and Modelsmentioning

confidence: 99%

Biomimetic chromatography—A novel application of the chromatographic principles

Valkó¹

2022

Analytical Science Advances

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Biomimetic chromatography is the name of the High Performance Liquid Chromatography (HPLC) methods that apply stationary phases containing proteins and phospholipids that can mimic the biological environment where drug molecules distribute. The applied mobile phases are aqueous organic with a pH of 7.4 to imitate physiological conditions that would be encountered in the human body. The calibrated retention of molecules on biomimetic stationary phases reveals a compound's affinity to proteins and phospholipids, which can be used to model the biological and environmental fate of molecules. This technology, when standardised, enables the prediction of in vivo partition and distribution behaviour of compounds and aids the selection of the best compounds for further studies to become a drug molecule. Applying biomimetic chromatographic measurements helps reduce the number of animal experiments during the drug discovery process. New biomimetic stationary phases, such as sphingomyelin and phosphatidylethanolamine, widen the application to the modelling of blood-brain barrier distribution and lung tissue binding. Recently, the measured properties have also been used to predict toxicity, such as phospholipidosis and cardiotoxicity. The aquatic toxicity of drugs and pesticides can be predicted using biomimetic chromatographic data. Biomimetic chromatographic separation methods may also be extended in the future to predict protein and receptor binding kinetics. The development of new biomimetic stationary phases and new prediction models will further accelerate the widespread application of this analytical method.

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“…Therefore, the investigated 1,2,4-triazole derivatives (named TPR) seem to be an interesting group of antiepileptic drug candidates. In our previous papers [15,42], we examined these compounds on the cholesterol-based stationary phase, and the commercially available phosphatidylcholine biomimetic stationary phase [42]. Molecular dynamics simulations revealed the selective preferences of the phosphatidylcholine with respect to the compounds with either ether or sulfide moieties.…”

Section: Scheme 1 Schematic Representations Of Stationary Phases (A)mentioning

confidence: 99%

“…The details of the anticonvulsant activity evaluation procedure and subsequent results are partially described in our previous works [15,37,42]. The anticonvulsant activity of the investigated compounds was measured in mice maximal electroshock (MES)-induced seizure model of epilepsy.…”

Section: Evaluation Of Anticonvulsant Activitymentioning

confidence: 99%

Teicoplanin-Modified HPLC Column as a Source of Experimental Parameters for Prediction of the Anticonvulsant Activity of 1,2,4-Triazole-3-Thiones by the Regression Models

et al. 2020

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The cell membrane is a complex system that consists of lipids, proteins, polysaccharides, and amphiphilic phospholipids. It plays an important role in ADME processes that are responsible for the final pharmaceutical effects of xenobiotics (bioavailability, activity). To study drug-membrane interaction at the molecular level, several high-performance liquid chromatography (HPLC) membrane model systems have been proposed which are mimicking mainly its lipid character. The aim of this work was to study interactions of new synthesized antiepileptic compounds of 4-alkyl-5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione derivatives with Chirobiotic column containing glycoprotein ligand attached to the silica matrix. The affinity of the analytes to immobilized glycoprotein ligand was examined chromatographically in reversed-phase mode. The thermodynamics of interactions between bioactive compounds and teicoplanin was studied in terms of the van’t Hoff linear relationship ln k vs. 1/T in the range of 5–45 °C. Change in enthalpy (ΔH°), change in entropy (ΔS°) and change in Gibbs free energy (ΔG°) were estimated utilizing graphical extrapolation and interpolation methods. The density functional theory (DFT) approach and docking simulations were used to get the molecular interpretation and prove the obtained experimental results. Cross-correlations of chromatographic and thermodynamic parameters with non-empirical topological and quantum chemical indices suggest that the polarizability of analytes appears to be responsible for the interactions of the tested molecules with teicoplanin and, ultimately, their retention on the column. Experimental and theoretical parameters were subjected to statistical analysis using regression models. Partial least squares (PLS) regression model showed the usefulness of the experimentally measured parameter φ0 (MeOH) to discriminate between anticonvulsant active and inactive 1,2,4-triazole-3-thione derivatives. Obtained results point out the usefulness of interaction of potential anticonvulsants with glycoprotein class of compounds to anticipate their activity.

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Thermodynamic study of new antiepileptic compounds by combining chromatography on the phosphatidylcholine biomimetic stationary phase and differential scanning calorimetry

Cited by 9 publications

References 57 publications

Levels of the Thiocyanate in the Saliva of Tobacco Smokers in Comparison to e-Cigarette Smokers and Nonsmokers Measured by HPLC on a Phosphatidylcholine Column

Levels of the Thiocyanate in the Saliva of Tobacco Smokers in Comparison to e-Cigarette Smokers and Nonsmokers Measured by HPLC on a Phosphatidylcholine Column

Biomimetic chromatography—A novel application of the chromatographic principles

Teicoplanin-Modified HPLC Column as a Source of Experimental Parameters for Prediction of the Anticonvulsant Activity of 1,2,4-Triazole-3-Thiones by the Regression Models

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