Recent developments in liquid and supercritical fluid chromatographic enantioseparations

Mangelings, Debby; Eeltink, Sebastiaan; Heyden, Yvan Vander

doi:10.1016/b978-0-444-64070-3.00009-6

Cited by 12 publications

(6 citation statements)

References 227 publications

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“…As a benefit of this phenomenon, tailorable applications can be developed with a high selectivity pre-determined for a particular substance or a group of structural analogues. In practice, the separation of nanomolar amounts of chiral molecules is performed most often by using chromatographic or electrophoretic methods based on chiral stationary phases [ 1 , 2 , 3 ]. These phases are typically immobilized host molecule-containing porous materials or molecular imprinted polymers [ 1 , 2 , 3 ].…”

Section: Introductionmentioning

confidence: 99%

“…In practice, the separation of nanomolar amounts of chiral molecules is performed most often by using chromatographic or electrophoretic methods based on chiral stationary phases [ 1 , 2 , 3 ]. These phases are typically immobilized host molecule-containing porous materials or molecular imprinted polymers [ 1 , 2 , 3 ]. The common drawbacks of these methods are the required great efforts for preliminary method development and the complicated and expensive preparation of the materials used for separation.…”

Section: Introductionmentioning

confidence: 99%

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Enantiodiscriminating Lipophilic Liquid Membrane-Based Assay for High-Throughput Nanomolar Enantioenrichment of Chiral Building Blocks

et al. 2023

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The reported optical resolution method was designed to support high-throughput enantioseparation of molecular building blocks obtained by automated small-scale synthetic methods. Lipophilic esters of common resolving agents were prepared and used as liquid membranes on the indifferent polymer surface of a microtiter assay. Chiral model compounds were enriched in one of the enantiomers starting from the aqueous solutions of their racemic mixture. Enantiodiscrimination was provided by forming diastereomeric coordination complexes of lipophilic enantiopure esters with the enantiomers of the chiral building blocks inside the liquid membranes. This enantiomeric recognition resulted in a greater distribution ratio of the preferred isomer in the membrane phase, thus the process enables a simultaneous enantioenrichment of the solutions outside the membrane. This paper reports a novel microplate-integrated stereoselective membrane enrichment technique satisfying the need for automatable enantioseparation on a subpreparative scale.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantiodiscriminating Lipophilic Liquid Membrane-Based Assay for High-Throughput Nanomolar Enantioenrichment of Chiral Building Blocks

et al. 2023

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“…It has a truncated cone shape that provides an inner hydrophobic space for hydrophobic drugs or active ingredients, together with a hydrophilic outer structure. Following the incorporation of hydrophobic active compounds into the interior cavity, an inclusion complex may be formed, which can enhance the overall aqueous stability of the compound [ 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

The Dual Modification of PNIPAM and β-Cyclodextrin Grafted on Hyaluronic Acid as Self-Assembled Nanogel for Curcumin Delivery

et al. 2022

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Curcumin is an extract of turmeric (Curcuma longa) which possesses anti-inflammatory, anti-cancer and wound-healing effects and has been used as an active compound in biomedical research for many years. However, its poor solubility presents challenges for its use in drug delivery systems. A modified nanogel delivery system, with PNIPAM and β-cyclodextrin grafted onto hyaluronic acid (PNCDHA), was utilized to enhance the solubility. The polymer was characterized by NMR, and the inclusion complex between curcumin and β-cyclodextrin was confirmed by FTIR. The potential of this PNCDHA polymer complex as a drug delivery vehicle was supported by a curcumin encapsulation efficiency of 93.14 ± 5.6% and the release of encapsulated curcumin at 37 °C. At a concentration of 0.5% w/v in water, PNCDHA nanogels were biocompatible with fibroblast cell line (L929) up to a curcumin concentration of 50 µM. There was a direct concentration between curcumin loading and cellular internalization. A more detailed study of the cellular internalization of PNCDHA nanogel should be considered in order to clarify cellular delivery mechanisms and to assess how its viability as a carrier may be optimized.

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“…Of the tremendous number of CSPs, the most frequently used chiral selectors are amino acids, proteins, derivatized linear or branched carbohydrates (e.g., cellulose or amylose), and cavity-type selectors, such as chiral crown ethers, cyclodextrins, cyclofructans, and macrocyclic antibiotics. These selectors and the CSPs made of them have been discussed in several reviews, books, and book chapters [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ]. In the discussion of this review article, we focus on scientific results published only between 2015 and the first quarter of 2021 obtained with LC applying macrocyclic antibiotics as CSPs.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

et al. 2021

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Numerous chemical compounds of high practical importance, such as drugs, fertilizers, and food additives are being commercialized as racemic mixtures, although in most cases only one of the isomers possesses the desirable properties. As our understanding of the biological actions of chiral compounds has improved, the investigation of the pharmacological and toxicological properties has become more and more important. Chirality has become a major issue in the pharmaceutical industry; therefore, there is a continuous demand to extend the available analytical methods for enantiomeric separations and enhance their efficiency. Direct liquid chromatography methods based on the application of chiral stationary phases have become a very sophisticated field of enantiomeric separations by now. Hundreds of chiral stationary phases have been commercialized so far. Among these, macrocyclic glycopeptide-based chiral selectors have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance. This review focuses on direct liquid chromatography-based enantiomer separations, applying macrocyclic glycopeptide-based chiral selectors. Special attention is paid to the characterization of the physico-chemical properties of these macrocyclic glycopeptide antibiotics providing detailed information on their applications published recently.

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Recent developments in liquid and supercritical fluid chromatographic enantioseparations

Cited by 12 publications

References 227 publications

Enantiodiscriminating Lipophilic Liquid Membrane-Based Assay for High-Throughput Nanomolar Enantioenrichment of Chiral Building Blocks

Enantiodiscriminating Lipophilic Liquid Membrane-Based Assay for High-Throughput Nanomolar Enantioenrichment of Chiral Building Blocks

The Dual Modification of PNIPAM and β-Cyclodextrin Grafted on Hyaluronic Acid as Self-Assembled Nanogel for Curcumin Delivery

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

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