Enantiomeric separation of tapentadol by capillary electrophoresis—Study of chiral selectivity manipulation by various types of cyclodextrins

Znaleziona, Joanna; Fejős, Ida; Ševčı́k, Juraj; Douša, Michal; Béni, Szabolcs; Maier, Vítězslav

doi:10.1016/j.jpba.2014.11.027

Cited by 27 publications

(17 citation statements)

References 16 publications

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“…A dual selector system has recently been used for the chiral separation of tapentadol enantiomers and the results were compared with those obtained when single CSs were utilized . Various types of CDs were used (e.g., α‐CD, β‐CD, γ‐CD, HP‐β‐CD, HP‐γ‐CD, SBE‐α‐CD, S‐α‐CD, CM‐α‐CD, and CM‐β‐CD), and among them, only HP‐β‐CD, HP‐γ‐CD, SBE‐α‐CD, S‐α‐CD, CM‐α‐CD, and CM‐β‐CD demonstrated a relative enantioselectivity toward tapentadol.…”

Section: Chiral Selectorsmentioning

confidence: 99%

Chiral selectors in CE: Recent development and applications (mid‐2014 to mid‐2016)

Stavrou

Agathokleous

Kapnissi‐Christodoulou

2017

Electrophoresis

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This report, which is a sequence of a series of reviews, records the most important chiral selectors (CSs) applied in CE. It highlights the CSs that were used during the period 2014 to mid-2016. In this review, method developments, validations, and pharmaceutical along with biomedical applications are presented. The different CSs include CDs, antibiotics, cyclofructants, linear and branched oligo- and polysaccharides, and polymeric surfactants. In addition, the advantages of these CSs, along with their chiral recognition mechanisms, and their performance, are discussed.

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Section: Chiral Selectorsmentioning

confidence: 99%

Chiral selectors in CE: Recent development and applications (mid‐2014 to mid‐2016)

Stavrou

Agathokleous

Kapnissi‐Christodoulou

2017

Electrophoresis

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“…Although no assay validation was performed the authors demonstrated that 0.1 % of the S , S ‐enantiomer could be detected as an impurity in tapentadol using 12 mM sulfated α‐CD in 50 mM Tris‐acetic acid, pH 4.75. In a subsequent study, the separation of all four stereoisomers of tapentadol was achieved . Native α‐, β‐, and γ‐CD as well as neutral and charged derivatives were initially screened at pH 2.5 (50 mM sodium phosphate buffer) and pH 9.5 (50 mM sodium borate buffer).…”

Section: Separation and Analysis Of Small Moleculesmentioning

confidence: 99%

“…Other experimental conditions: 56.0/64.5 cm, 50 mm id fused silica capillary, 25 kV, 15°C. (Reproduced with permission from Elsevier from . )…”

Section: Separation and Analysis Of Small Moleculesmentioning

confidence: 99%

Recent advances in capillary electrophoretic migration techniques for pharmaceutical analysis (2013–2015)

et al. 2016

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This review updates and follows-up a previous review by highlighting recent advancements regarding capillary electromigration methodologies and applications in pharmaceutical analysis. General approaches such as quality by design as well as sample injection methods and detection sensitivity are discussed. The separation and analysis of drug-related substances, chiral CE, and chiral CE-MS in addition to the determination of physicochemical constants are addressed. The advantages of applying affinity capillary electrophoresis in studying receptor-ligand interactions are highlighted. Finally, current aspects related to the analysis of biopharmaceuticals are reviewed. The present review covers the literature between January 2013 and December 2015.

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“…Affinity capillary electrophoresis (ACE) was utilized for the determination of interactions between drugs and CDs and polymers of CDs . Binding constants between enantiomers and CDs were determined for dipeptides , vinca alkaloids , tadalafil , tapentadol , nucleoside phosphonates and other analytes as reviewed in . Assuming a 1:1 complexation, the binding constant is calculated from the change in effective mobility an analyte gets at increasing CD concentrations.…”

Section: Introductionmentioning

confidence: 99%

Characterization of complexes between phenethylamine enantiomers and β‐cyclodextrin derivatives by capillary electrophoresis—Determination of binding constants and complex mobilities

et al. 2017

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To optimize chiral separation conditions and to improve the knowledge of enantioseparation, it is important to know the binding constants K between analytes and cyclodextrins and the electrophoretic mobilities of the temporarily formed analyte-cyclodextrin-complexes. K values for complexes between eight phenethylamine enantiomers, namely ephedrine, pseudoephedrine, methylephedrine and norephedrine, and four different β-cyclodextrin derivatives were determined by affinity capillary electrophoresis. The binding constants were calculated from the electrophoretic mobility values of the phenethylamine enantiomers at increasing concentrations of cyclodextrins in running buffer. Three different linear plotting methods (x-reciprocal, y-reciprocal, double reciprocal) and nonlinear regression were used for the determination of binding constants with β-cyclodextrin, (2-hydroxypropyl)-β-cyclodextrin, methyl-β-cyclodextrin and 6-O-α-maltosyl-β-cyclodextrin. The cyclodextrin concentration in a 50 mM phosphate buffer pH 3.0 was varied from 0 to 12 mM. To investigate the influence of the binding constant values on the enantioseparation the observed electrophoretic selectivities were compared with the obtained K values and the calculated enantiomer-cyclodextrin-complex mobilities. The different electrophoretic mobilities of the temporarily formed complexes were crucial factors for the migration order and enantioseparation of ephedrine derivatives. To verify the apparent binding constants determined by capillary electrophoresis, a titration process using ephedrine enantiomers and β-cyclodextrin was carried out. Furthermore, the isothermal titration calorimetry measurements gave information about the thermal properties of the complexes.

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Enantiomeric separation of tapentadol by capillary electrophoresis—Study of chiral selectivity manipulation by various types of cyclodextrins

Cited by 27 publications

References 16 publications

Chiral selectors in CE: Recent development and applications (mid‐2014 to mid‐2016)

Chiral selectors in CE: Recent development and applications (mid‐2014 to mid‐2016)

Recent advances in capillary electrophoretic migration techniques for pharmaceutical analysis (2013–2015)

Characterization of complexes between phenethylamine enantiomers and β‐cyclodextrin derivatives by capillary electrophoresis—Determination of binding constants and complex mobilities

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