Separation of terbutaline enantiomers in capillary electrophoresis with cyclodextrin-type chiral selectors and investigation of structure of selector-selectand complexes

Gogolashvili, Ann; Tatunashvili, Elene; Chankvetadze, Lali; Sohajda, Tamás; Szemán, Julianna; Gümüştaş, Mehmet; Özkan, Síbel A.; Salgado, Antonio; Chankvetadze, Bezhan

doi:10.1016/j.chroma.2018.08.012

Cited by 38 publications

(30 citation statements)

References 27 publications

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“…In recent decades, plenty of researches have concentrated on separation of chiral compounds by CE. The research results reveal that CE is a powerful technique for enantiomers separation based on its high degree of flexibility, high separation efficiency, short analysis time, and low cost . In enantioseparation by CE, the chiral additives which are also referred to as “selector” in the electrolyte played an important role.…”

Section: Migration Time Resolution Selectivity Factor and Column Ementioning

confidence: 99%

Investigation of deep eutectic solvents as additives to β‐CD for enantiomeric separations of Zopiclone, Salbutamol, and Amlodipine by CE

Huang

et al. 2019

Electrophoresis

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The enantioseparation of chiral drugs via CE was first investigated using β‐CD as chiral additive and deep eutectic solvents (DESs) as auxiliary additive. The results showed that improved separation of tested chiral drugs was obtained in the presence of DESs and β‐CD compared to the single β‐CD separation system. With the optimized condition, resolutions of DESs applied β‐CD separation system for rac‐Zopiclone, rac‐Salbutamol, and rac‐Amlodipine increased 3–4.2 times as single β‐CD separation system. The resolutions reached 4.74, 6.37, and 9.67, respectively. The results demonstrate that DESs are viable additives to CD system in CE for the separation of the chiral drugs.

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Section: Migration Time Resolution Selectivity Factor and Column Ementioning

confidence: 99%

Investigation of deep eutectic solvents as additives to β‐CD for enantiomeric separations of Zopiclone, Salbutamol, and Amlodipine by CE

Huang

et al. 2019

Electrophoresis

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“…Racemic dapoxetine and alogliptin were synthesized as described previously . Terbutaline enantiomers were isolated and kindly provided by Prof. B. Chankvetadze according to their recent publication .…”

Section: Methodsmentioning

confidence: 99%

“…In our study, all the single isomer per‐monomethylated, per‐dimethylated, and the commercially available randomly substituted CDs along with the per‐trimethylated derivative were screened using a set of racemic compounds in CCE to establish structure‐enantiodiscrimination relationships. To get an atomic level picture on the enantiorecognition, a commonly used model drug terbutaline was chosen .…”

Section: Introductionmentioning

confidence: 99%

Comparative analysis of the full set of methylated β‐cyclodextrins as chiral selectors in capillary electrophoresis

et al. 2019

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Comparative analysis of the full set of methylated ␤-cyclodextrins as chiral selectors in capillary electrophoresisThe chiral separation ability of the full library of methylated-␤-cyclodextrins towards pharmacologically significant racemic drugs including basic compounds was studied by chiral CE. The syntheses of all the methylated, single isomer ␤-cyclodextrins were revised and optimized and the aqueous solubility of the derivatives was unambiguously established. The three most relevant commercially available methylated isomeric mixtures were also included in the screening, so a total of ten various methylated CDs were investigated. The effects of the selector concentration on the enantiorecognition properties at acidic pH were investigated. Among the dimethylated ␤-cyclodextrins, the heptakis (2,6-di-Omethyl)-␤-cyclodextrin isomer (2,6-DIMEB) resulted to be the most versatile chiral selector. Terbutaline was selected as a model compound for the in-depth investigation of host-guest enantiodiscrimination ability. The association constants between the two terbutaline enantiomers and 2,6-DIMEB were determined in order to support that the enantioseparation is driven by differences is host-guest binding. The migration order of the enantiomers was confirmed by performing spiking experiments with the pure enantiomers. 1D and 2D NMR spectroscopy was applied to the 2,3-, and 2,6-DIMEB/terbutaline systems to rationalize at molecular level the different enantioseparation ability of the dimethylated ␤-cyclodextrin selectors.

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“…The enantioselective environment created by chiral ceramics is the key to recognition of the molecular chirality of enantiomers and the ability to achieve their separation. [182] Many chiral ligands that ceramics can be derivatized with including proteins, [183] cyclodextrin, [184] crown ethers, [185] oligo-and polysaccharides, [186] etc., have been developed for chiral recognition and separation. The combination of different chiral selectors, a variety of chiral and achiral ceramic nanostructures have been developed for efficient recognition and separation of enantiomers by various methods, for example, filtration, centrifugation, chromatography, high-performance liquid chromatography, etc.…”

Section: Chiral Separationmentioning

confidence: 99%

Chiral Nanoceramics

Fan

Kotov

2020

Advanced Materials

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Jinchen Fan received his Ph.D. degree from Shanghai Jiao Tong University in 2014. He is now an associate professor at Shanghai University of Electric Power, China. He joined Prof. Kotov's group as a visiting scholar from October 2017 to October 2019. His current research focus is on the fabrication of chiral nanoceramics and their applications in chiroptical activity and catalysis. 2.2. Chiral Assemblies and Soft Templates Most of organic amphiphiles can be assembled into chiral superstructures. [43] This series of superstructures can be used as soft templates in the preparation of helical ceramic nanomaterials including, SiO 2 , [44] Ta 2 O 5 , [45] TiO 2 , [46] ZrO 2 , [47] and poly(bi ssilsesquioxane) [48] via the sol-gel transcription approach. Similarly, bio-macromolecules, such as peptides and DNA can serve as templates for realizing chiral ZnO [49] and silica structures. [50] Chiral synthesis with sodium cholate (SC) also serves as a representative example of this method. Because of its amphiphilic character, SC self-assembles into a unique bilayer structure through the hydrogen bonding between hydroxyl groups. [51] Huang and co-workers [51b] used the SC assembled via coordination with calcium ions, well-defined helical nanoribbons for creating additional helical SiO 2 and ZnS by sol-gel process. Methods of chirality transfer from soft templates often include self-organization ceramic building blocks based on hydrogen bonding, van der Waals forces, π-π stacking, hydrophobic effect, electrostatic and Coulomb interactions, and metal coordination. [41] One of representative examples of chiral assembly is the preparation of chiral nanostructured silica that proceeds via Nicholas A. Kotov pioneered conceptual foundations and technical realizations of biomimetic nanostructures, which include chiral nanomaterials. Chiral ceramic nanostructures are being investigated in his laboratory for optical, magnetic, biological, and catalytic properties. His contribution to technology include nacremimetic nanocomposites including those from graphene oxide, 3D tissue replicas for drug-testing, chiral biosensors, and cartilage-like electrolytes for batteries. He is a founder of several start-up companies that commercialized bioinspired nanomaterials for biomedical, energy, and automotive technologies.

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Separation of terbutaline enantiomers in capillary electrophoresis with cyclodextrin-type chiral selectors and investigation of structure of selector-selectand complexes

Cited by 38 publications

References 27 publications

Investigation of deep eutectic solvents as additives to β‐CD for enantiomeric separations of Zopiclone, Salbutamol, and Amlodipine by CE

Investigation of deep eutectic solvents as additives to β‐CD for enantiomeric separations of Zopiclone, Salbutamol, and Amlodipine by CE

Comparative analysis of the full set of methylated β‐cyclodextrins as chiral selectors in capillary electrophoresis

Chiral Nanoceramics

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