Acidity of substituted cathinones studied by capillary electrophoresis using the standard and fast alternative approaches

Woźniakiewicz, Michał; Nowak, Paweł Mateusz; Gołąb, Małgorzata; Adamowicz, Piotr; Kala, Mansi; Kościelniak, Paweł

doi:10.1016/j.talanta.2017.12.025

Cited by 15 publications

(5 citation statements)

References 32 publications

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“…Although the enantiomers of 4‐MMC have been separated several times , its parent drug (MC) has been selected more rarely , whereas its important isomer (3‐MMC) has not been separated chirally until now. A very close similarity of structures and p K a values of MC, 4‐MMC and 3‐MMC , shown in Fig. , makes their simultaneous enantioseparation not straightforward.…”

Section: The Values Of Validation Parameters Obtained For MC 3‐mmc Amentioning

confidence: 95%

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Simultaneous enantioseparation of methcathinone and two isomeric methylmethcathinones using capillary electrophoresis assisted by 2‐hydroxyethyl‐β‐cyclodextrin

et al. 2018

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Methcathinone (ephedrone), 4-methylmethcathinone (mephedrone), and 3-methylmethcathinone (metaphedrone) are toxicologically-important cathinone derivatives used commonly as designer drugs. In this work we show the first method allowing to separate simultaneously all these molecules in a chiral medium, ensuring good resolution between all enantiomers. Eight cyclodextrins have been tested as potential chiral selectors, the best results were obtained with 2-hydroxyethyl-β-cyclodextrin, unreported so far for efficient separation of cathinones. After optimization, the method was calibrated and validated with and without the use of internal standard. The addition of standard improved an overall repeatability and precision, the use of electrophoretic mobility ratio was especially favorable (RSD < 1%). It was demonstrated that the method may be easily extended by introducing the additional cathinone-related drugs to the sample, maintaining satisfactory separation efficiency.

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Section: The Values Of Validation Parameters Obtained For MC 3‐mmc Amentioning

confidence: 95%

“…At the beginning, the sample containing MC, 3‐MMC, 4‐MMC (analytes) and 1‐PEA (internal standard) was separated in the phosphate buffers enriched with 10 mM CDs, of the pH value 8.7, close to the p K a values of all three cathinones , see Fig. .…”

Section: The Values Of Validation Parameters Obtained For MC 3‐mmc Amentioning

confidence: 99%

Simultaneous enantioseparation of methcathinone and two isomeric methylmethcathinones using capillary electrophoresis assisted by 2‐hydroxyethyl‐β‐cyclodextrin

et al. 2018

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“…CE has been utilized for pK a determination of various compounds mainly in aqueous solutions [28][29][30][31][32][33][34][35] but also in mixed hydro-organic solvents [27,36] and nonaqueous media [37][38][39]. Recently, several innovations in CE determination of pK a have been proposed.…”

Section: Introductionmentioning

confidence: 99%

Acidity constants and protonation sites of cyclic dinucleotides determined by capillary electrophoresis, quantum chemical calculations, and NMR spectroscopy

Štěpánová,

Andris,

Gutten

et al. 2023

Electrophoresis

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Cyclic dinucleotides (CDNs) are important second messengers in bacteria and eukaryotes. Detailed characterization of their physicochemical properties is a prerequisite for understanding their biological functions. Herein, we examine acid–base and electromigration properties of selected CDNs employing capillary electrophoresis (CE), density functional theory (DFT), and nuclear magnetic resonance (NMR) spectroscopy to provide benchmark pKa values, as well as to unambiguously determine the protonation sites. Acidity constants (pKa) of the NH+ moieties of adenine and guanine bases and actual and limiting ionic mobilities of CDNs were determined by nonlinear regression analysis of the pH dependence of their effective electrophoretic mobilities measured by CE in aqueous background electrolytes in a wide pH range (0.98–11.48), at constant temperature (25°C), and constant ionic strength (25 mM). The thermodynamic pKa values were found to be in the range 3.31–4.56 for adenine and 2.28–3.61 for guanine bases, whereas the pKa of enol group of guanine base was in the range 10.21–10.40. Except for systematic shifts of ∼2 pKa, the pKa values calculated by the DFT‐D3//COSMO‐RS composite protocol that included large‐scale conformational sampling and “cross‐morphing” were in a relatively good agreement with the pKas determined by CE and predict N1 atom of adenine and N7 atom of guanine as the protonation sites. The protonation of the N1 atom of adenine and N7 atom of guanine in acidic background electrolytes (BGEs) and the dissociation of the enol group of guanine in alkaline BGEs was confirmed also by NMR spectroscopy.

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“…It is a highly automated technique that requires small amounts of compounds and where high purity is not required due to the separation performed inside the capillary. [12][13][14][15][16][17][18][19] The IS-CE method is based on the use of an internal standard (i.e. a compound with known pKa) to measure the pH inside the capillary.…”

Section: Introductionmentioning

confidence: 99%

Determination of acidity constants at 37 °C through the internal standard capillary electrophoresis (IS-CE) method: internal standards and application to polyprotic drugs

Lebanov

Fuguet

Melo

et al. 2020

Analyst

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Acidity of substituted cathinones studied by capillary electrophoresis using the standard and fast alternative approaches

Cited by 15 publications

References 32 publications

Simultaneous enantioseparation of methcathinone and two isomeric methylmethcathinones using capillary electrophoresis assisted by 2‐hydroxyethyl‐β‐cyclodextrin

Simultaneous enantioseparation of methcathinone and two isomeric methylmethcathinones using capillary electrophoresis assisted by 2‐hydroxyethyl‐β‐cyclodextrin

Acidity constants and protonation sites of cyclic dinucleotides determined by capillary electrophoresis, quantum chemical calculations, and NMR spectroscopy

Determination of acidity constants at 37 °C through the internal standard capillary electrophoresis (IS-CE) method: internal standards and application to polyprotic drugs

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