Stereoselective separation of psychoactive substances: Multivariate optimization and validation of a capillary electrophoresis method using carboxymethyl-β-CD/deep eutectic solvent dual system

Ioannou, Katerina A.; Ioannou, Georgia D.; Christou, Atalanti; Stavrou, Ioannis J.; Schmid, Martin G.; Kapnissi-Christodoulou, Constantina P.

doi:10.1016/j.jpba.2023.115897

Cited by 3 publications

(1 citation statement)

References 31 publications

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“…Because of the relatively short period of time since their introduction in separation sciences, chiral DES has not yet been extensively studied especially with regard to the separation mechanism. Typically, DES was used in combination with established chiral selectors such as CDs, see for example [174][175][176][177][178]. Very recently, several DES based on lactobionic acid as sole chiral selectors have been introduced, but the interactions between the analytes and the selector components were not elucidated by spectroscopic or modeling approaches [179].…”

Section: Chiral Ils and Dessmentioning

confidence: 99%

Update on chiral recognition mechanisms in separation science

Scriba

2024

J of Separation Science

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The stereospecific analysis of chiral molecules is an important issue in many scientific fields. In separation sciences, this is achieved via the formation of transient diastereomeric complexes between a chiral selector and the selectand enantiomers driven by molecular interactions including electrostatic, ion‐dipole, dipole‐dipole, van der Waals or π‐π interactions as well as hydrogen or halogen bonds depending on the nature of selector and selectand. Nuclear magnetic resonance spectroscopy and molecular modeling methods are currently the most frequently applied techniques to understand the selector‐selectand interactions at a molecular level and to draw conclusions on the chiral separation mechanism. The present short review summarizes some of the recent achievements for the understanding of the chiral recognition of the most important chiral selectors combining separation techniques with molecular modeling and/or spectroscopic techniques dating between 2020 and early 2024. The selectors include polysaccharide derivatives, cyclodextrins, macrocyclic glycopeptides, proteins, donor‐acceptor type selectors, ion‐exchangers, crown ethers, and molecular micelles. The application of chiral ionic liquids and chiral deep eutectic solvents, as well as further selectors, are also briefly addressed. A compilation of all published literature on chiral selectors has not been attempted.

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Section: Chiral Ils and Dessmentioning

confidence: 99%

Update on chiral recognition mechanisms in separation science

Scriba

2024

J of Separation Science

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Thiolated Chiral Naphthalene Diimide Derivatives as Effective Selectors of the β‐Blocker Atenolol Enantiomers

Kowalczyk,

Duszczyk,

Sęk

et al. 2024

Adv Funct Materials

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Atenolol β‐blocker drug (ATN) to treat hypertension and cardiovascular disorders such as angina pectoris is manufactured commercially in a racemic form, while only its (S)‐enantiomer shows selective β1‐blocking activity. Here, a new axially chiral thiolated naphthalene diimide derivatives (HS‐BIN‐NDI) for the rapid, simple, and sensitive detection of ATN enantiomers is presented. The Surface Plasmon Resonance (SPR) and Atomic Force Microscopy (AFM) experiments show that interactions between a chiral selector and a chiral analyte occur only when their configurations are opposite. The extensive computational simulations support this finding. The association coefficient determined by SPR is high (105‐106 M−1 s−1) and indicates that the interactions are electrostatic. The analytical utility of atropisomeric HS‐BIN‐NDIs is proven, and the voltammetric sensors designed to determine ATN enantiomers are constructed. The developed sensors are characterized by a wide analytical operating range from 5.0·10−3 to 1.0 µm, nanomolar detection limit, high selectivity, and a long lifetime. Several additives like urea, creatinine, glucose, human albumin, and hemoglobin do not affect ATN sensing.

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Enantiomeric separation of nefopam and cathinone derivatives using a supramolecular deep eutectic solvent as a chiral selector in capillary electrophoresis

Ioannou,

Georgiou,

Ioannou

et al. 2024

Electrophoresis

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The present study investigates the utilization of a supramolecular deep eutectic solvent (SUPRADES), consisting of sulfated‐β‐cyclodextrin (S‐β‐CD) and citric acid (CA), as a chiral selector (CS) in capillary electrophoresis for the enantiomeric separation of nefopam (NEF) and five cathinone derivatives (3‐methylmethcathinone [3‐MMC], 4‐methylmethcathinone [4‐MMC], 3,4‐dimethylmethcathinone [3,4‐DMMC], 4‐methylethcathinone [4‐MEC], and 3,4‐methylendioxycathinone [MDMC]). A significant improvement in enantiomeric separation of the target analytes was observed upon the addition of S‐β‐CD‐CA to the background electrolyte (BGE), leading to a baseline separation of all analytes. In particular, the optimum percentage of S‐β‐CD‐CA, added to the BGE, was determined to be 0.075% v/v for NEF (Rs = 1.5) and 0.050% v/v for three out of five cathinone derivatives (Rs = 1.5, 1.6, and 2.4 for 3‐MMC, 4‐MEC, and 3,4‐DMMC, respectively). In the case of 4‐MMC and MDMC, a higher percentage of the CS, equal to 0.075% and 0.10% v/v, respectively, was required to achieve baseline separation (Rs = 1.5, 1.9 for MDMC and 4‐MMC, respectively). The outcomes of the present study highlight the potential effectiveness of using SUPRADES as a CS in electrophoretic enantioseparations.

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Stereoselective separation of psychoactive substances: Multivariate optimization and validation of a capillary electrophoresis method using carboxymethyl-β-CD/deep eutectic solvent dual system

Cited by 3 publications

References 31 publications

Update on chiral recognition mechanisms in separation science

Update on chiral recognition mechanisms in separation science

Thiolated Chiral Naphthalene Diimide Derivatives as Effective Selectors of the β‐Blocker Atenolol Enantiomers

Enantiomeric separation of nefopam and cathinone derivatives using a supramolecular deep eutectic solvent as a chiral selector in capillary electrophoresis

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