Illustration of a simple and versatile scheme for reversing enantiomeric elution order and facilitating enantiomeric impurity determination in capillary electrophoresis

Magnusson, Jeanette; Wan, Hong; Blomberg, Lars G.

doi:10.1002/1522-2683(200209)23:17<3013::aid-elps3013>3.0.co;2-k

Cited by 18 publications

(3 citation statements)

References 35 publications

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“…There are different ways to change the enantiomeric migration order by CE when CDs are used as chiral selectors [4,[10][11][12][13]: (i) modifying the CD cavity size [14]; (ii) changing the nature of CD substituents [15,16]; (iii) varying the location of substituents on the CD rim [17]; (iv) employing charged CDs in the BGE and changing the polarity of the applied voltage [18,19]; (v) modifying the pH of the BGE [18,20]; (vi) changing the EOF, i.e., eliminating or reversing it [19,20]; (vii) using achiral additives (i.e., micelles or ligandexchange compounds as metals) in chiral systems [21,22], and finally, (viii) varying the concentration of the CD in the separation buffer. However, this last phenomenon has scarcely been observed.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration

Castro‐Puyana¹,

Crego²,

Marina³

et al. 2007

Electrophoresis

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The enantioselective separation of a group of six weak base azole compounds was achieved in this work using EKC with three neutral b-CDs as chiral selectors. The native b-CD and two other b-CD derivatives with different types and positions of the substituents on the CD rim ((2-hydroxy)propyl-b-CD (HP-b-CD) and heptakis-2,3,6-tri-O-methyl-b-CD (TM-b-CD)) were employed. Apparent binding constants for each pair compound-CD were determined in order to study analyte-CD interactions. The best enantiomeric resolutions for miconazole, econazole, and sulconazole were observed with HP-b-CD whereas for the separation of the enantiomers of ketoconazole, terconazole, and bifonazole, TM-b-CD was the best chiral selector. The enantioseparations obtained were discussed on the basis of the structure of the compounds taking into account that inclusion into the hydrophobic CD cavity occurred through the phenyl ring closer to the azole group. In addition, a change in the migration order for the enantiomers of two of the compounds studied (ketoconazole and terconazole) with the concentration of HP-b-CD was observed for the first time.

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Section: Introductionmentioning

confidence: 99%

Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration

Castro‐Puyana¹,

Crego²,

Marina³

et al. 2007

Electrophoresis

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“…Also, Magnusson et al, exemplified the setback of enantiomeric elution instruction and discovered enantiomeric impurity in CE for IBP. Poor IBP resolution with HS-β-CD (R s : 0.7) was well resolved (R s : 3.3) with dual cyclodextrin (TM-β-CD & HS-β-CD) [35]. Matthij et al [36] stated the enantiomeric separation of several pharmaceuticals with various acid-basic characteristics (16 basics, 8 acids, and 1 neutral) which were analyzed by employing twin cyclodextrin systems, one of which is strongly sulfated (α, β, γ-HSCD) and one neutral cyclodextrin, i.e., either Dimethyl-β-cyclodextrin (DM-β-CD), TM-β-CD, or Hydroxypropyl-β-cyclodextrin (HP-β-CD), which are examined with these pharmacological substances.…”

Section: Chiral Drug Separations For Cementioning

confidence: 99%

Emerging Developments in Separation Techniques and Analysis of Chiral Pharmaceuticals

Al-Sulaimi,

Kushwah,

Abdullah Alsibani

et al. 2023

Molecules

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Chiral separation, the process of isolating enantiomers from a racemic mixture, holds paramount importance in diverse scientific disciplines. Using chiral separation methods like chromatography and electrophoresis, enantiomers can be isolated and characterized. This study emphasizes the significance of chiral separation in drug development, quality control, environmental analysis, and chemical synthesis, facilitating improved therapeutic outcomes, regulatory compliance, and enhanced industrial processes. Capillary electrophoresis (CE) has emerged as a powerful technique for the analysis of chiral drugs. This review also highlights the significance of CE in chiral drug analysis, emphasizing its high separation efficiency, rapid analysis times, and compatibility with other detection techniques. High-performance liquid chromatography (HPLC) has become a vital technique for chiral drugs analysis. Through the utilization of a chiral stationary phase, HPLC separates enantiomers based on their differential interactions, allowing for the quantification of individual enantiomeric concentrations. This study also emphasizes the significance of HPLC in chiral drug analysis, highlighting its excellent resolution, sensitivity, and applicability. The resolution and enantiomeric analysis of nonsteroidal anti-inflammatory drugs (NSAIDs) hold great importance due to their chiral nature and potential variations in pharmacological effects. Several studies have emphasized the significance of resolving and analyzing the enantiomers of NSAIDs. Enantiomeric analysis provides critical insights into the pharmacokinetics, pharmacodynamics, and potential interactions of NSAIDs, aiding in drug design, optimization, and personalized medicine for improved therapeutic outcomes and patient safety. Microfluidics systems have revolutionized chiral separation, offering miniaturization, precise fluid control, and high throughput. Integration of microscale channels and techniques provides a promising platform for on-chip chiral analysis in pharmaceuticals and analytical chemistry. Their applications in techniques such as high-performance liquid chromatography (HPLC) and capillary electrochromatography (CEC) offer improved resolution and faster analysis times, making them valuable tools for enantiomeric analysis in pharmaceutical, environmental, and biomedical research.

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“…For a thorough discussion the reader is referred to a recent review [77]. Blomberg et al [78] have suggested a versatile scheme for reversing the enantiomer migration order using ibuprofen and propranolol as model compounds for acidic and basic analytes. The resolution of the propranolol enantiomers was achieved using the charged HDAS-b-CD while a mixture of HDAS-b-CD and the neutral TM-b-CD was applied for ibuprofen.…”

Section: Enantioseparations Of Nonracemic Mixtures Determination Of mentioning

confidence: 99%

Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An update

Scriba¹

2003

Electrophoresis

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Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An updateCapillary electrophoresis is often considered an ideal method for the chiral analysis of compounds due to the high separation power of the technique and has therefore found widespread acceptance for the analysis of drugs and pharmaceuticals. In contrast, capillary electrochromatography is still more or less in an infancy state searching for its place among the analytical separation techniques although interesting applications have been published. The present review summarizes recent developments and applications of chiral pharmaceutical analysis by electromigration techniques published in 2002 and early 2003.

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Illustration of a simple and versatile scheme for reversing enantiomeric elution order and facilitating enantiomeric impurity determination in capillary electrophoresis

Cited by 18 publications

References 35 publications

Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration

Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration

Emerging Developments in Separation Techniques and Analysis of Chiral Pharmaceuticals

Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An update

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