Interactions of non-charged tadalafil stereoisomers with cyclodextrins: Capillary electrophoresis and nuclear magnetic resonance studies

Fejős, Ida; Kazsoki, Adrienn; Sohajda, Tamás; Marvanyos, E.; Volk, Balázs; Szente, Lajos; Béni, Szabolcs

doi:10.1016/j.chroma.2014.08.045

Cited by 20 publications

(9 citation statements)

References 27 publications

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“…Fejős et al. used a number of negatively and positively charged CDs, and they examined the enantioseparation of tadalafil and its interaction with the CDs by use of CE and NMR. Among the examined negatively charged CDs, SBE‐α‐CD was the most promising CD, and it was proposed as a CS in routine CE enantioseparations for the stereoisomeric impurity profiling of tadalafil.…”

Section: Chiral Selectorsmentioning

confidence: 99%

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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%

“…Fejős et al. , as it was mentioned earlier, studied the chiral separation of the four stereoisomers of tadalafil by the use of different negatively and positively charged CDs. Although negatively charged CDs demonstrated higher enantioseparation capabilities, some positively charged CDs proved to be enantioselective.…”

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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“…Recently, a review article covering 4 years of publications has been describing the evolution on the use of derivatization reagents, ligand exchange CE, and the use of CE‐MS with some insight on frontier nanomaterials . It has been showing how CE is well adapted to easily study these compounds.…”

Section: Separation Of Enantiomersmentioning

confidence: 99%

Recent advances in amino acid analysis by capillary electromigration methods, 2013–2015

et al. 2015

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We describe the most important research articles published on amino acid analysis using CE during the period from June 2013 to May 2015, and follows the format of the previous articles published in electrophoresis the new developments in amino acid analysis with CE are mainly describing improvements in detection means and injection methods. Enantiomeric separation developments are still important. Focusing the applications, we describe the neurochemical and clinical works, but also the metabolomic studies for which the publication number increase greatly. Finally, works focused on amino acids in food and agricultural applications are described.

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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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Interactions of non-charged tadalafil stereoisomers with cyclodextrins: Capillary electrophoresis and nuclear magnetic resonance studies

Cited by 20 publications

References 27 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 amino acid analysis by capillary electromigration methods, 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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