Chiral recognition and racemic resolution of drug enantiomers by electrophoresis based on host-guest complexation

Liu, Jinping; Coffey, Heather; Detlefsen, David J.; Li, Yang; Lee, Mike S.

doi:10.1016/s0021-9673(96)00997-1

Cited by 14 publications

(8 citation statements)

References 23 publications

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“…It has to be noticed that based on multidisciplinary approach involving separation science, spectroscopic techniques, X-ray crystallography, and molecular modeling significant advancements were achieved. At the same time, despite the fact that the first studies to model CD/chiral analyte complexes formed in CE environment date back to the 1990s [82,159], there is still a long way to go in order to reach the state when it will be possible, based on the structure of analyte and CD, to predict the binding strength and affinity pattern in CD complexes with chiral guests. Further advancement in this field requires combined application of the most advanced separation, spectroscopic and molecular modeling tools.…”

Section: Molecular Modeling Of Capillary Electrophoresis Enantioseparations Promoted By Cyclodextrins: Applicationsmentioning

confidence: 99%

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Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Peluso

Chankvetadze

2021

Electrophoresis

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CDs are cyclic oligosaccharides consisting of α‐d‐glucopyranosyl units linked through 1,4‐linkages, which are obtained from enzymatic degradation of starch. The coexistence of hydrophilic and hydrophobic regions in the same structure makes these macrocycles extremely versatile as complexing host with application in food, cosmetics, environmental, agriculture, textile, pharmaceutical, and chemical industries. Due to their inherent chirality, CDs have been also successfully used as chiral selectors in enantioseparation science, in particular, for CE enantioseparations. In the last decades, multidisciplinary approaches based on CE, NMR spectroscopy, X‐ray crystallography, microcalorimetry, and molecular modeling have shed light on some aspects of recognition mechanisms underlying enantiodiscrimination. With the ever growing improvement of computer facilities, hardware and software, computational techniques have become a useful tool to model at molecular level the dynamics of diastereomeric associate formation to sample low‐energy conformations, the binding energies between the enantiomer and the CD, and to profile noncovalent interactions contributing to the stability of CD/enantiomer association. On this basis, the aim of this review is to provide the reader with a critical overview on the applications of CDs in CE. In particular, the contemporary theory of the electrophoretic technique and the main structural features of CDs are described, with a specific focus on techniques, methods, and approaches to model CE enantioseparations promoted by native and substituted CDs. A systematic compilation of all published literature has not been attempted.

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Section: Molecular Modeling Of Capillary Electrophoresis Enantioseparations Promoted By Cyclodextrins: Applicationsmentioning

confidence: 99%

“…In 1997, Liu and co‐authors reported CE enantioseparation of a series of water‐ soluble melatonergic drugs with β‐CD and 2,6‐DM‐β‐CD as chiral selectors [159], indicating higher affinity of the CDs towards the S ‐enantiomer. Using BMS‐191435 (Fig.…”

Section: Molecular Modeling Of Capillary Electrophoresis Enantiosepar...mentioning

confidence: 99%

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Peluso

Chankvetadze

2021

Electrophoresis

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“…In the pharmaceutical industry, much research has been conducted in recent years on enantiomerically pure compounds, in order to discover and develop safer and more ef®cacious drugs (Liu et al, 1997;Bolender & Richardson, 2003). Moreover, most of today's top-selling drugs are optically pure enantiomers (Maier et al, 2001).…”

Section: Commentmentioning

confidence: 99%

9-[Ethoxy(8-quinolylamino)methyl]anthracene

Bin

Zhou

et al. 2004

Acta Cryst E

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“…In order to provide safer and more effective drugs, the chiral recognition and pharmacological screening of chiral molecules are an important analytical subject. 3 Electrochemical technology is a chiral recognition method to identify enantiomers by studying the different electrochemical behaviors of the enantiomers on the electrode surface. It has the advantages of being simple, fast, and effective.…”

Section: Introductionmentioning

confidence: 99%

A biomolecule chiral interface base on BSA for electrochemical recognition of amine enantiomers

Chen

Meng

et al. 2021

Chirality

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A composite chiral interface (BSA-MB-MWCNTs) was prepared from bovine serum albumin (BSA), methylene blue (MB), and multi-walled carbon nanotubes (MWCNTs) for chiral recognition of amine enantiomers (1S, 2S)-N,N 0 -dimethyl-1,2-cyclohexanediamine and (1R, 2R)-N,N 0 -dimethyl-1,2-cyclohexanediamine. The BSA-based composite was characterized by field emission scanning electron microscopy (FESEM) and ultraviolet-visible spectroscopy (UV-Vis). The electrochemical responses towards the two enantiomers were analyzed via cyclic voltammetry (CV), electrochemical AC impedance method (EIS), and differential-pulse voltammetry (DPV). The experimental results showed that the combination of MWCNTs and BSA could effectively improve the overall identification efficiency, and the peak current displayed by the S-enantiomer is larger, indicating that the prepared chiral surface has stronger interaction with the R-enantiomer. Under optimized condition, the current value of the oxidation peak of the chiral modified electrode showed a good linear relationship towards the amine concentration in the range of 5.0 Â 10 À3 to 5.0 Â 10 À5 mmolÁL À1 . The proposed electrochemical chiral interface is easy to handle and provides a promising electrochemical sensing platform that can be used to identify chiral amine enantiomers.

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Chiral recognition and racemic resolution of drug enantiomers by electrophoresis based on host-guest complexation

Cited by 14 publications

References 23 publications

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

9-[Ethoxy(8-quinolylamino)methyl]anthracene

A biomolecule chiral interface base on BSA for electrochemical recognition of amine enantiomers

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