Recognition and separation of enantiomers based on functionalized magnetic nanomaterials

Deng, Xiaojuan; Li, Wenbin; Wang, Yi; Ding, Guoyu

doi:10.1016/j.trac.2020.115804

Cited by 28 publications

(23 citation statements)

References 74 publications

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“…Although some articles have made detailed summarizations about chiral resolution, [4][5][6][7][8][9] as one of the hot spots, lots of impressive progresses have been achieved driven by the development of new technologies and theories in recent years. And yet there has no article summarized the newly emerged methods, such as the separation based on chiral-induced spin selectivity, resulting in a blank of systematic and comprehensive collation and summary.…”

Section: Introductionmentioning

confidence: 99%

Advances and applications of chiral resolution in pharmaceutical field

Teng

Chen

et al. 2022

Chirality

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The attention to chiral drugs has been raised to an unprecedented level as drug discovery and development strategies grow rapidly. However, separation of enantiomers is still a huge task, which leads to an increasing significance to equip a wider range of expertise in chiral separation science to meet the current and future challenges. In the last few decades, remarkable progress of chiral resolution has been achieved. This review summarizes and classifies chiral resolution methods in analytical scale and preparative scale systematically and comprehensively, including crystallization‐based method, inclusion complexation, chromatographic separation, capillary electrophoresis, kinetic resolution, liquid–liquid extraction, membrane‐based separation, and especially one bold new progress based on chiral‐induced spin selectivity theory. The advances and recent applications will be presented in detail, in which the contents may bring more thinking to wide‐ranging readers in various professional fields, from analytical chemistry, pharmaceutical chemistry, natural medicinal chemistry, to manufacturing of drug production.

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Section: Introductionmentioning

confidence: 99%

Advances and applications of chiral resolution in pharmaceutical field

Teng

Chen

et al. 2022

Chirality

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“…Chiral differentiation and quantification of organic enantiomers are always challenging due to the tiny discrepancies in their chemical and physical properties. [11][12][13] Despite all of this, differentiation of pregabalin enantiomers has been successful in some areas, such as liquid chromatography and capillary electrophoresis. For example, Zhang et al 14 utilized serial macrocyclic glycopeptides as chiral stationary phases to separate the pregabalin enantiomers by highperformance liquid chromatography (HPLC), and Béni et al 15 effectively separated pregabalin enantiomers at various pHs by derivatizing the isomers through capillary zone electrophoresis.…”

Section: Introductionmentioning

confidence: 99%

“…Chiral differentiation and quantification of organic enantiomers are always challenging due to the tiny discrepancies in their chemical and physical properties 11–13 . Despite all of this, differentiation of pregabalin enantiomers has been successful in some areas, such as liquid chromatography and capillary electrophoresis.…”

Section: Introductionmentioning

confidence: 99%

Enantio‐separation of pregabalin by ternary complexation using trapped ion mobility spectrometry

Yang

et al. 2021

Rapid Comm Mass Spectrometry

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Rationale The rapid identification of small‐molecule chiral drugs is challenging due to subtle structural differences. Different enantiomers of chiral drugs may produce inverse biological effects through their different pharmacokinetics. Therefore, it is highly desirable to distinguish the chirality of drug molecules. Methods The chirality of pregabalin was distinguished by studying the ion mobility spectra of the ternary non‐covalent complexes formed with cyclodextrins (CDs), pregabalin, and alkali‐earth cations using trapped ion mobility spectrometry (TIMS). The ternary non‐covalent complex ions were determined by electrospray ionization of mixed solutions. The analyzed sample was simply mixed, without derivatization or sample pretreatment. The relative contents of pregabalin enantiomers were derived using a calibration curve method. Results The ion mobility spectra of several ternary non‐covalent complexes formed with α‐, β‐, and γ‐CD, pregabalin, and alkali‐earth cations were obtained. We compared their ability to distinguish the chirality of pregabalin. The best peak‐to‐peak resolution (Rp‐p) was estimated to be 2.20 for [2β‐CD + pregabalin + Sr]2+, which can be ascribed as baseline separation. The derived relative contents for S‐pregabalin were in agreement with the actual contents. Conclusions A novel and convenient method for discriminating the chirality of the pregabalin molecule by TIMS was developed and optimized. The chirality of pregabalin was recognized by studying the ion mobility spectra of the ternary non‐covalent complexes, such as [2β‐CD + pregabalin + Sr]2+. This TIMS method could also be used to quantify the relative contents of pregabalin enantiomers.

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“…Over the last decades, several fundamental reviews and book chapters assembled the main achievements related to preparative separation of enantiomers [16,[19][20][21][22][23][24]. In this overview, the currently most applied techniques and the recently progresses achieved on preparative chiral separations are brief reported, focusing in the importance to achieve pure enantiomers at the early phases of the pipeline of drugs discovery and development.…”

Section: Introductionmentioning

confidence: 99%

Chiral Separations in Preparative Scale: A Medicinal Chemistry Point of View

2020

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Enantiomeric separation is a key step in the development of a new chiral drug. Preparative liquid chromatography (LC) continues to be the technique of choice either during the drug discovery process, to achieve a few milligrams, or to a scale-up during the clinical trial, needing kilograms of material. However, in the last few years, instrumental and technical developments allowed an exponential increase of preparative enantioseparation using other techniques. Besides LC, supercritical fluid chromatography (SFC) and counter-current chromatography (CCC) have aroused interest for preparative chiral separation. This overview will highlight the importance to scale-up chiral separations in Medicinal Chemistry, especially in the early stages of the pipeline of drugs discovery and development. Few examples within different methodologies will be selected, emphasizing the trends in chiral preparative separation. The advantages and drawbacks will be critically discussed.

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Recognition and separation of enantiomers based on functionalized magnetic nanomaterials

Cited by 28 publications

References 74 publications

Advances and applications of chiral resolution in pharmaceutical field

Advances and applications of chiral resolution in pharmaceutical field

Enantio‐separation of pregabalin by ternary complexation using trapped ion mobility spectrometry

Chiral Separations in Preparative Scale: A Medicinal Chemistry Point of View

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