Chiral recognition of dapoxetine enantiomers with methylated-gamma-cyclodextrin: A validated capillary electrophoresis method

Neumajer, Gábor; Sohajda, Tamás; Darcsi, András; Tóth, Gergő; Szente, Lajos; Noszál, Béla; Béni, Szabolcs

doi:10.1016/j.jpba.2011.12.032

Cited by 28 publications

(12 citation statements)

References 33 publications

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“…The robustness of the method was studied using Plackett–Burmann statistical experimental design, a practical approach to evaluate flexibility of analytical methods, in order to minimize the number of experiments . As response factors resolution, corrected peak area and migration time for R‐ Vilda were recorded.…”

Section: Methodsmentioning

confidence: 99%

Development and validation of a cyclodextrin‐modified capillary electrophoresis method for the enantiomeric separation of vildagliptin enantiomers

et al. 2016

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The enantiomers of vildagliptin, an orally available and selective dipeptidyl-peptidase-4 inhibitor used for the treatment of type II diabetes, have been separated by CD-modified CZE, using uncoated fused-silica capillary. After screening 13 negatively charged CD derivatives as potential chiral selectors, sulfobutyl-ether-α-CD (SBE-α-CD) was selected for the enantioseparation. For the optimization, a factorial analysis study was performed by orthogonal experimental design. Six experimental factors were chosen as variable parameters: temperature, applied voltage, chiral selector and BGE concentrations, pH, and the parameters of the hydrodynamic injection. The optimized system still was not considered final as the second peak (S-enantiomer) migrated too close to the EOF, resulting in a potential inaccuracy during the determination of the chiral impurity. To fine-tune the method "one factor at a time" variation approach was applied. The final method (applying 15°C capillary temperature, 40 mbar × 4 s hydrodynamic injection, 25 kV voltage in 75 mM acetate-Tris buffer [pH 4.75] containing 20 mM SBE-α-CD as chiral selector) was validated according to the ICH guideline. RSD percentage of the resolution value, migration times, and corrected peak areas were below 5% during testing repeatability and intermediate precision. LOD and LOQ values were found to be 2.5 and 7.5 μg/mL, respectively. The method is considered linear in the 7.5-180 μg/mL range for the R-enantiomer. The robustness of the method was justified using Plackett-Burmann statistical experimental design.

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Section: Methodsmentioning

confidence: 99%

Development and validation of a cyclodextrin‐modified capillary electrophoresis method for the enantiomeric separation of vildagliptin enantiomers

et al. 2016

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“…Wide range of CD derivatives with exactly known numbers and positions of substituents on CD glucose units is also used in electromigration methods. The most common derivatives have the same substituents on all the given carbon atoms of the glucose units (persubstituted derivatives at a given position or persubstituted derivatives where all the hydroxyl groups are replaced with the same functional group), for example, heptakis(2‐ O ‐sulfo‐3‐ O ‐methyl‐6‐ O ‐acetyl)‐β‐CD and per‐ O ‐methyl‐β‐CD .…”

Section: Cds As Additives In Chiral Cementioning

confidence: 99%

Application of cyclodextrins in chiral capillary electrophoresis

et al. 2014

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CE represents a very powerful separation tool in the area of chiral separations. CD-mediated chiral CE is a continuously flourishing technique within the frame of the electromigration methods. In this review, a brief overview of the synthetic procedures leading to modified CDs is provided first. Next, selected aspects related to the utilization of CDs in chiral CE are discussed specifically in the view of recently published data. Advantages of CDs and basic principles of chiral CE are remained. The topic of the determination of binding constants is touched. Particular attention is paid to the effort aiming at better understanding of the molecular level of the enantiorecognition between CDs and the analyte in the solution. Powerful approaches extensively utilized in this field are NMR, molecular modeling, and computer simulations. Then, a summary of applications of CDs in the CE enantioseparations is given, covering years 2008-2013. Finally, the general trend of modified CDs use in separation science is statistically evaluated.

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“…The main goal was the screening of different CD derivatives for the chiral separations in these studies. The stereoisomers of dapoxetine , vinpocetine , and nicotine butyric acid were also successfully separated.…”

Section: Recent Applications Of Ce Enantioseparationsmentioning

confidence: 99%

Recent advances in electrodriven enantioseparations

Jáč

Scriba

2012

J of Separation Science

110

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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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Chiral recognition of dapoxetine enantiomers with methylated-gamma-cyclodextrin: A validated capillary electrophoresis method

Cited by 28 publications

References 33 publications

Development and validation of a cyclodextrin‐modified capillary electrophoresis method for the enantiomeric separation of vildagliptin enantiomers

Development and validation of a cyclodextrin‐modified capillary electrophoresis method for the enantiomeric separation of vildagliptin enantiomers

Application of cyclodextrins in chiral capillary electrophoresis

Recent advances in electrodriven enantioseparations

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