Enantioseparation of novel psychoactive chiral amines and their mixture by capillary electrophoresis using cyclodextrins as chiral selectors

Řezanková, Klára; Kohoutová, Radka; Kuchař, Martin; Král, Vladimír; Řezanka, Pavel

doi:10.1007/s11696-018-0535-2

Cited by 16 publications

(9 citation statements)

References 23 publications

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“…In literature, several articles deal with the enantioseparation of cathinone related compounds and further NPS. Chiral separations were carried out via different separation techniques including HPLC , supercritical fluid chromatography , GC , and also CE and CEC . Electrophoretically driven methods have great advantage that no expensive chiral stationary phases are needed.…”

Section: Introductionmentioning

confidence: 99%

Chiral separation of cathinone derivatives using β‐cyclodextrin‐assisted capillary electrophoresis–Comparison of four different β‐cyclodextrin derivatives used as chiral selectors

2019

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In the past decade, more than 100 different cathinone derivatives slopped over entire Europe due to their enormous popularity. Generally, these novel psychoactive substances are easily available via the internet. This fact leads to various social problems, since cathinones are substances with consciousness‐changing effects and are mainly misused for recreational matters by their consumers. Cathinones possess a chiral center including two enantiomeric forms with potentially different pharmacological behavior. This fact makes analytical method development regarding their chiral separation indispensable. In this study, a chiral capillary zone electrophoresis method for the enantioseparation of 61 cathinone and pyrovalerone derivatives was developed by means of four different β‐cyclodextrin derivatives. As chiral selectors, native β‐cyclodextrin as well as three of its derivatives namely acetyl‐β‐cyclodextrin, 2‐hydroxypropyl‐β‐cyclodextrin, and carboxymethyl‐β‐cyclodextrin were used. The cathinone and pyrovalerone derivatives were either purchased in internet stores or seized by police. As a result, overall 58 of 61 studied substances were partially or baseline separated by at least one of the four chiral selectors using 10 mM of β‐cyclodextrin derivative in a 10 mM sodium phosphate buffer (pH 2.5). Furthermore, the method was found to be suitable for simultaneous enantioseparations, for enantiomeric purity checks and to differentiate between positional isomers. Moreover, an intra‐ and an interday validation was performed successfully for each chiral selector to prove the robustness of the method.

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Section: Introductionmentioning

confidence: 99%

Chiral separation of cathinone derivatives using β‐cyclodextrin‐assisted capillary electrophoresis–Comparison of four different β‐cyclodextrin derivatives used as chiral selectors

2019

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“…From the measured electropherograms, it was concluded that the separation proceeds better in the phosphate buffer at a lower pH value. From the selected CDs ( Figure 5 ), i.e., β-CD, carboxymethylated β-cyclodextrin (CM-β-CD), heptakis(2,3,6-tri- O -methyl)-β-cyclodextrin (Me-β-CD), 2-hydroxypropylated β-cyclodextrin (HP-β-CD), sulfated β-cyclodextrin (S-β-CD), γ-CD, and carboxymethylated γ-cyclodextrin (CM-γ-CD), CM-β-CD, which is often used for the separation of basic nitrogenous substances [ 52 , 53 ], seems to be the most suitable. This may be due to the interaction of the carboxyl group of CM-β-CD with the NH group of the analyte and also due to the appropriate size of the β-CD cavity.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, in the search for optimal separation conditions, it is possible to achieve higher concentrations if necessary. [52,53], seems to be the most suitable. This may be due to the interaction of the carboxyl group of CM-β-CD with the NH group of the analyte and also due to the appropriate size of the β-CD cavity.…”

Section: Cyclodextrin Optimizationmentioning

confidence: 99%

Enantioseparation and Determination of Mephedrone and Its Metabolites by Capillary Electrophoresis Using Cyclodextrins as Chiral Selectors

et al. 2020

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Mephedrone, a psychoactive compound derived from cathinone, is widely used as a designer drug. The determination of mephedrone and its metabolites is important for understanding its possible use in medicine. In this work, a method of capillary electrophoresis for the chiral separation of mephedrone and its metabolites was developed. Carboxymethylated β-cyclodextrin was selected as the most effective chiral selector from seven tested cyclodextrin derivates. Based on the simplex method, the optimal composition of the background electrolyte was determined: at pH 2.75 and 7.5 mmol·L−1 carboxymethylated β-cyclodextrin the highest total resolution of a mixture of analytes was achieved. For mephedrone and its metabolites, calibration curves were constructed in a calibration range from 0.2 to 5 mmol·L−1; limits of detection, limits of quantification, precision, and repeatability were calculated, and according to Mandel’s fitting test, the linear calibration ranges were determined.

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“…The same format can be used for chiral separations [98]. A recent report based on this approach used it to separate a mixture of eleven psychoactive chiral amines [99]. Other applications have included the chiral analysis of pharmaceuticals such as levornidazole [100] or verapamil [101].…”

Section: Carbohydratesmentioning

confidence: 99%

Clinical and pharmaceutical applications of affinity ligands in capillary electrophoresis: A review

Zhang

Woolfork

Suh

et al. 2020

Journal of Pharmaceutical and Biomedical Analysis

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Affinity capillary electrophoresis (ACE) is a separation technique that combines a biologically-related binding agent with the separating power and efficiency of capillary electrophoresis. This review will examine several classes of binding agents that have been used in ACE and applications that have been described for the resulting methods in clinical or pharmaceutical analysis. Binding agents that will be considered are antibodies, aptamers, lectins, serum proteins, carbohydrates, and enzymes. This review will also describe the various formats in which each type of binding agent has been used in CE, including both homogeneous and heterogeneous methods. Specific areas of applications that will be considered are CE-based immunoassays, glycoprotein/glycan separations, chiral separations, and biointeraction studies. The general principles and formats of ACE for each of these applications will be examined, along with the potential advantages or limitations of these methods.

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Enantioseparation of novel psychoactive chiral amines and their mixture by capillary electrophoresis using cyclodextrins as chiral selectors

Cited by 16 publications

References 23 publications

Chiral separation of cathinone derivatives using β‐cyclodextrin‐assisted capillary electrophoresis–Comparison of four different β‐cyclodextrin derivatives used as chiral selectors

Chiral separation of cathinone derivatives using β‐cyclodextrin‐assisted capillary electrophoresis–Comparison of four different β‐cyclodextrin derivatives used as chiral selectors

Enantioseparation and Determination of Mephedrone and Its Metabolites by Capillary Electrophoresis Using Cyclodextrins as Chiral Selectors

Clinical and pharmaceutical applications of affinity ligands in capillary electrophoresis: A review

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