Enantiomeric separation of antimalarial drugs by capillary electrophoresis using neutral and negatively charged cyclodextrins

Németh, Krisztina; Tárkányi, Gábor; Varga, Erzsébet; Imre, Tı́mea; Mizsei, Réka; Iványi, Róbert; Visy, Júlia; Szemán, Julianna; Jicsinszky, László; Szente, Lajos; Simonyi, Miklós

doi:10.1016/j.jpba.2010.09.020

Cited by 43 publications

(29 citation statements)

References 41 publications

(67 reference statements)

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“…Carboxymethyl CDs represent a group of potentially nega‐tively charged (according to pH of the electrolyte) CD derivatives and all α‐, β‐, and γ‐ carboxymethylated CDs have been successfully used for CE separations. Specifically, mixtures of carboxymethyl‐α‐cyclodextrin (CMACD) derivatives have been utilized for the separation of disopyramide [], dipeptides and tripeptides [], metoprolol [], tocainide [], antimalarial drugs [], cis ‐β‐lactam derivatives [], and vinca alkaloids []. These works have been based on the cooperation of several scientific groups with Cyclolab Ltd. (Budapest, Hungary), the company producing mixtures of randomly carboxymethylated α‐CDs with the degree of substitution 2–3.…”

Section: Introductionmentioning

confidence: 99%

Impact of substituent position in monosubstituted α‐cyclodextrins on enantioselectivity in capillary electrophoresis

Řezanka

Sýkora

et al. 2012

J of Separation Science

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In this study, our three recently synthesized regiospecifically monosubstituted carboxymethyl-α-cyclodextrins (CMACDs) were successfully applied for the enantiomeric separation of several biologically important low-molecular weight compounds by capillary electrophoresis. The enantioselectivity of the individual monosubstituted CMACDs added into the background electrolyte (BGE) was studied and compared with the mixture of three monosubstituted CMACDs and with native α-cyclodextrin at pH of the BGE ranging from 2.5 to 11. Our experiments revealed a significant influence of the position of the carboxymethyl group on the α-cyclodextrin skeleton on the enantioselectivity for all the studied analytes. Interestingly, the least common 3(I)-O regioisomer was revealed as the most effective chiral selector.

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Section: Introductionmentioning

confidence: 99%

Impact of substituent position in monosubstituted α‐cyclodextrins on enantioselectivity in capillary electrophoresis

Řezanka

Sýkora

et al. 2012

J of Separation Science

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“…Under such conditions, the basic analytes were completely protonated, and thus migrated in the same direction with the EOF. For CM‐ β ‐CD, as its p K a is ~4 (Németh et al, ), with increasing buffer pH from 2.5 to 5.0, it was nearly uncharged or gradually negatively charged. Figure depicts the apparent electrophoretic mobility (μ app ), electroosmotic mobility (μ eo ) and electrophoretic mobility (μ eff ) variations of pindolol vs the increment of pH.…”

Section: Resultsmentioning

confidence: 99%

“…Until now, a remarkable number of chiral drugs and related compounds have been enantioseparated with CM‐ β ‐CD as chiral selector in CE, such as metoprolol and its metabolites (Lim, Linh, Hong, Lim, & Kang, ), neurotransmitters (Maruszak, Trojanowicz, Margasińska, & Engelhardt, ), dimetindene maleate (Chankvetadze, Schulte, Bergenthal, & Blaschke, ), bevantolol (Long, Trung, Oh, & Kim, ), meptazinol and its three intermediate enantiomers (Yu et al, ) and antimalarial drugs (Németh et al, ). Comprehensively, we could draw the conclusion that carboxymethyl‐ β ‐CD (CM‐ β ‐CD) exhibited excellent chiral selectivity toward neutral and positively charged analytes.…”

Section: Introductionmentioning

confidence: 99%

“…This conclusion agreed with the observation made by Li et al (), indicating that negatively charged CM‐ β ‐CD provided more recognition sites for chiral separation, especially in the separation of analytes bearing amine and hydroxyl substituent groups. Additionally, some researchers found that molecular size, charge and the specific functional groups or substructures in the structures of analytes were very important in enantioseparation (Németh et al, ; Yu et al, ). Although the detailed mechanism of the enantioseparation was still lacking, several studies on the study of the possible driving forces responsible for separation have been reported.…”

Section: Introductionmentioning

confidence: 99%

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Carboxymethyl β‐cyclodextrin as chiral selector in capillary electrophoresis: Enantioseparation of 16 basic chiral drugs and its chiral recognition mechanism associated with drugs' structural features

Fang

et al. 2017

Biomedical Chromatography

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Herein we present the enantioseparation of 10 cardiovascular agents and six bronchiectasis drugs including propranolol, carteolol, metoprolol, atenolol, pindolol, esmolol, bisoprolol, bevantolol, arotinolol, sotalol, clenbuterol, procaterol, bambuterol, tranterol, salbutamol and terbutaline sulfate using carboxymethyl-β-cyclodextrin (CM-β-CD) as chiral selector. To our knowledge, there is no literature about using CM-β-CD for separating carteolol, esmolol, bisoprolol, bevantolol, arotinolol, procaterol, bambuterol and tranterol. During the course of work, changes in pH, CM-β-CD concentration, buffer type and concentration were studied in relation to chiral resolution. Excellent enantiomeric separations were obtained for all 16 compounds, especially for procaterol. An impressive resolution value, up to 17.10, was obtained. In particular, most of them achieved rapid separations within 20 min. Given the fact that enantioseparation results rely on analytes' structural characters, the possible separation mechanisms were discussed. In addition, in order to obtain faster separation for propranolol enantiomers in practical application, the effective length of capillary was innovatively shortened from 45 to 30 cm. After the validation, the method was successfully applied to the enantiomeric purity determination of propranolol in the formulation of drug substances.

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“…Other reports focused on the enantioseparation of various classes of compounds such as β‐carboline derivatives , helquats , iodiconazol and other triadimenol analogs , antimalarics , and cathinone derivatives with different CDs. The main goal was the screening of different CD derivatives for the chiral separations in these studies.…”

Section: Recent Applications Of Ce Enantioseparationsmentioning

confidence: 99%

Recent advances in electrodriven enantioseparations

Jáč

Scriba

2012

J of Separation Science

109

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Capillary electromigration techniques have developed into significant analytical separation tools especially for enantioseparations. While CE can be considered a mature technique as documented by its wide applications, CEC is still in a developmental state despite many research efforts. The success of stereospecific CE separation methods is due to the high specificity and flexibility of the technique as well as the availability of many types of chiral selectors. Thus, numerous methods have been developed for the analysis of chiral compounds in chemical, biochemical, pharmaceutical, environmental, and forensic sciences. However, most reported applications deal with pharmaceuticals. The search for new chiral selectors also continued despite the fact that most applications were performed using cyclodextrins. Furthermore, CE has been combined with spectroscopic and molecular modeling studies in attempts to understand the interactions between chiral selectors and analytes. The present review focuses on recent examples of mechanistic aspects of capillary enantioseparations with regard to mathematical modeling of enantioseparations, investigations of the analyte-complex structures as well as new chiral selectors and applications of chiral analyses by CE and CEC. It covers the literature published between January 2011 and August 2012.

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Enantiomeric separation of antimalarial drugs by capillary electrophoresis using neutral and negatively charged cyclodextrins

Cited by 43 publications

References 41 publications

Impact of substituent position in monosubstituted α‐cyclodextrins on enantioselectivity in capillary electrophoresis

Impact of substituent position in monosubstituted α‐cyclodextrins on enantioselectivity in capillary electrophoresis

Carboxymethyl β‐cyclodextrin as chiral selector in capillary electrophoresis: Enantioseparation of 16 basic chiral drugs and its chiral recognition mechanism associated with drugs' structural features

Recent advances in electrodriven enantioseparations

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