Recent developments in cyclodextrin functionalized monolithic columns for the enantioseparation of chiral drugs

Guo, Jialiang; Yang, Lin; Xiao, Ying; Crommen, Jacques; Jiang, Zhengjin

doi:10.1016/j.jpba.2016.05.023

Cited by 39 publications

(24 citation statements)

References 102 publications

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“…In the last decades, capillary electrophoresis (CE) has gained great success for the enantioseparation of chiral molecules [1][2][3][4]. Traditional CE chiral separation mostly occurred in aqueous BGE [3,[5][6][7][8], but CE in non-aqueous BGEs improved compatibility with mass spectrometric detector compared to CE in aqueous BGEs, due to its merits such as lower conductivity and favorable dissolution ability of hydrophobic compounds [3,[8][9][10][11]. Interestingly, a reversal of the enantiomer affinity pattern (EAP) of some enantiomers was observed when cyclodextrin (CD) additives or BGEs were replaced in aqueous/non-aqueous systems, and received much more attention in recent years.…”

Section: Introductionmentioning

confidence: 99%

Combination of capillary electrophoresis and molecular modeling to study the enantiomer affinity pattern between β‐blockers and anionic cyclodextrin derivatives in a methanolic and water background electrolyte

et al. 2019

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In order to have deep insights into the mechanisms of enantiomer affinity pattern in both aqueous and non‐aqueous systems, an approach combining capillary electrophoresis and molecular modeling was undertaken. A chiral β‐blocker; acebutolol, was enantioseparated in aqueous capillary electrophoresis and non‐aqueous capillary electrophoresis using two anionic β‐cyclodextrin derivatives. The enantiomer affinity pattern of acebutolol was found to be opposite when an aqueous background electrolyte was replaced with non‐aqueous background electrolyte in the presence of heptakis(2,3‐di‐O‐acetyl‐6‐sulfo)‐β‐cyclodextrin but remained the same in the presence of heptakis(2,3‐di‐O‐methyl‐6‐sulfo)‐β‐cyclodextrin. Molecular docking of acebutolol into two β‐cyclodextrin derivatives indicated two distinct binding modes called ‘up’ and ‘down’ conformations. After structure optimization by molecular dynamics and energy minimization, both enantiomers of acebutolol were preferred to the ‘up’ conformation with heptakis(2,3‐di‐O‐methyl‐6‐sulfo)‐β‐cyclodextrin while ‘down’ conformation with heptakis(2,3‐di‐O‐acetyl‐6‐sulfo)‐β‐cyclodextrin. The further calculation of the complex energy with solvent effect indicated that heptakis(2,3‐di‐O‐acetyl‐6‐sulfo)‐β‐cyclodextrin had higher affinity to S‐acebutolol than R‐acebutolol in non‐aqueous capillary electrophoresis while it showed better binding to R‐acebutolol in aqueous capillary electrophoresis. However, the heptakis(2,3‐di‐O‐methyl‐6‐sulfo)‐β‐cyclodextrin bound better to R‐acebutolol in both aqueous and non‐aqueous capillary electrophoresis, implying that the binding mode played more important role in chiral separation of heptakis(2,3‐di‐O‐methyl‐6‐sulfo)‐β‐cyclodextrin while the solvent effect had prevailing impact on heptakis(2,3‐di‐O‐acetyl‐6‐sulfo)‐β‐cyclodextrin.

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Section: Introductionmentioning

confidence: 99%

Combination of capillary electrophoresis and molecular modeling to study the enantiomer affinity pattern between β‐blockers and anionic cyclodextrin derivatives in a methanolic and water background electrolyte

et al. 2019

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“…4,5 In the agricultural field, the ineffective configuration of chiral pesticides not only does not have the effect of weeding but also may cause environmental pollution and endanger human health. [13][14][15][16] In CEC, the column is the most critical component. 6,7 Therefore, it is necessary for enantioseparation in the field of pharmaceutical and agricultural science.…”

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“…In addition, a hybrid technique, such as capillary electrochromatography (CEC), has also been used for enantioseparations. 15 Cationic CDs become an important branch of functionalized CDs and have exhibited great potential in enantioseparations. In recent years, enantioseparations using CEC attract more and more attention because of the short analysis time and low sample and solvent consumption.…”

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confidence: 99%

“…In recent years, enantioseparations using CEC attract more and more attention because of the short analysis time and low sample and solvent consumption. [13][14][15][16] In CEC, the column is the most critical component. Depending on fabricating techniques, three types of columns have been employed including packed columns, monolithic columns, and OT columns.…”

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“…19 Cyclodextrin (CD) and their derivatives (CDs) have been widely used as chiral stationary phases (CSPs), and the researches grow tremendously. 15 Cationic CDs become an important branch of functionalized CDs and have exhibited great potential in enantioseparations. For example, Yu et al prepared a new cationic β-CD derivative, mono-6-deoxy-6-piperdine-β-CD (PIP-β-CD), and successfully applied for the enantioseparation of meptazinol and its three intermediate enantiomers by CE.…”

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Preparation and characterization of a new open‐tubular capillary column for enantioseparation by capillary electrochromatography

Tang

Qin

et al. 2019

Chirality

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In order to use the enantioseparation capability of cationic cyclodextrin and to combine the advantages of capillary electrochromatography (CEC) with opentubular (OT) column, in this study, a new OT-CEC, coated with cationic cyclodextrin (1-allylimidazolium-β-cyclodextrin [AI-β-CD]) as chiral stationary phase (CSP), was prepared and applied for enantioseparation. Synthesized AI-β-CD was characterized by infrared (IR) spectrometry and mass spectrometry (MS). The preparation conditions for the AI-β-CD-coated column were optimized with the orthogonal experiment design L 9 (3 4 ). The column prepared was characterized by scanning electron microscopy (SEM) and elemental analysis (EA). The results showed that the thickness of stationary phase in the inner surface of the AI-β-CD-coated columns was about 0.2 to 0.5 μm. The AI-β-CD content in stationary phase based on the EA was approximately 2.77 mmol·m −2 . The AI-β-CD-coated columns could separate all 14 chiral compounds (histidine, lysine, arginine, glutamate, aspartic acid, cysteine, serine, valine, isoleucine, phenylalanine, salbutamol, atenolol, ibuprofen, and napropamide) successfully in the study and exhibit excellent reproducibility and stability. We propose that the column, coated with AI-β-CD, has a great potential for enantioseparation in OT-CEC.

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Cyclodextrins

Scriba

Konjaria

Krait

2023

Chiral Separations and Stereochemical Elucidation

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Recent developments in cyclodextrin functionalized monolithic columns for the enantioseparation of chiral drugs

Cited by 39 publications

References 102 publications

Combination of capillary electrophoresis and molecular modeling to study the enantiomer affinity pattern between β‐blockers and anionic cyclodextrin derivatives in a methanolic and water background electrolyte

Combination of capillary electrophoresis and molecular modeling to study the enantiomer affinity pattern between β‐blockers and anionic cyclodextrin derivatives in a methanolic and water background electrolyte

Preparation and characterization of a new open‐tubular capillary column for enantioseparation by capillary electrochromatography

Cyclodextrins

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