Establishment and molecular modeling study of maltodextrin-based synergistic enantioseparation systems with two new hydroxy acid chiral ionic liquids as additives in capillary electrophoresis

Yang, Xuan; Du, Yingxiang; Feng, Zijie; Liu, Zongran; Li, Jingtang

doi:10.1016/j.chroma.2017.06.007

Cited by 40 publications

(18 citation statements)

References 41 publications

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“…1 H- 19 F heteronuclear Overhauser spectroscopy data indicated also the inclusion of EtCholNTf2 into the CD cavity. The enhanced enantioselectivity of selectors in combination with CILs was also studied by CE and molecular modeling for HP-β-CD [99] and maltodextrin [100].…”

Section: Structures Of Selector-selectand Complexesmentioning

confidence: 99%

Advances of capillary electrophoresis enantioseparations in pharmaceutical analysis (2017–2020)

2021

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Capillary electrophoresis is a powerful technique for the analysis of polar chiral compounds and has been widely accepted for analytical enantioseparations of drug compounds in pharmaceuticals and biological media. In addition, many mechanistic studies have been conducted in an attempt to rationalize enantioseparations in combination with spectroscopic and computational techniques. The present review will focus on recent examples of mechanistic aspects and summarize recent applications of stereoselective pharmaceutical and biomedical analysis published between January 2017 and November 2020. Various separation modes including electrokinetic chromatography in combination with several detection modes including laser-induced fluorescence, mass spectrometry and contactless conductivity detection will be discussed. A general trend also observed in other analytical techniques is the application of quality by design principles in method development and optimization.

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Section: Structures Of Selector-selectand Complexesmentioning

confidence: 99%

Advances of capillary electrophoresis enantioseparations in pharmaceutical analysis (2017–2020)

2021

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“…Its helical structure allows it to be a flexible CS, but high concentrations are required for effectiveness. There were three reports where maltodextrin was used alone [59] and in conjunction with other CS [23,60] in EKC. 20% ( w / v ) maltodextrin in pH 8.0 BGS was able to separate tramadol and methadone enantiomers satisfactorily [59].…”

Section: Macromoleculesmentioning

confidence: 99%

“…20% ( w / v ) maltodextrin in pH 8.0 BGS was able to separate tramadol and methadone enantiomers satisfactorily [59]. Meanwhile, only 3% ( w / v ) maltodextrin but in combination with chiral ILs in the BGS were able to separate four racemic drugs [60]. A comparison of the separations using maltodextrin alone and with 50 mM each of tetramethylammonium hydroxide, tetramethylammonium- d -pantothenate and tetramethylammonium- d -quinate clearly showed an improvement in separation in the presence of an IL.…”

Section: Macromoleculesmentioning

confidence: 99%

“…We note that an achiral IL derivatised β-CD was reported (see Section 2.1.1.2) in 2018. During this review period, amino acid or amide based chiral ILs were mainly used in conjunction with a macromolecule (mostly a CD) [31,60,82,90,91,92,93]. In general, chiral separations were obtained only with both IL and macromolecule in the BGS.…”

Section: Low Molecular Weight Compoundsmentioning

confidence: 99%

“…Molecular modelling can help the researcher understand the different steps involved in the molecular recognition process, the non-bonding interactions involved between the analyte and the CS and the binding energies for their association. During this review period, ten studies utilised molecular modelling, with the intention of understanding chiral recognition mechanism and elution migration order [22,32,35,44,60,62,72,73,94,95]. Molecular modelling has also been utilised to design new CSs [40].…”

Section: Molecular Modelling and Nmr Studiesmentioning

confidence: 99%

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Chiral Selectors in Capillary Electrophoresis: Trends during 2017–2018

Quirino

2019

Molecules

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Chiral separation is an important process in the chemical and pharmaceutical industries. From the analytical chemistry perspective, chiral separation is required for assessing the fit-for-purpose and the safety of chemical products. Capillary electrophoresis, in the electrokinetic chromatography mode is an established analytical technique for chiral separations. A water-soluble chiral selector is typically used. This review therefore examines the use of various chiral selectors in electrokinetic chromatography during 2017–2018. The chiral selectors were both low and high (macromolecules) molecular mass molecules as well as molecular aggregates (supramolecules). There were 58 papers found by search in Scopus, indicating continuous and active activity in this research area. The macromolecules were sugar-, amino acid-, and nucleic acid-based polymers. The supramolecules were bile salt micelles. The low molecular mass selectors were mainly ionic liquids and complexes with a central ion. A majority of the papers were on the use or preparation of sugar-based macromolecules, e.g., native or derivatised cyclodextrins. Studies to explain chiral recognition of macromolecular and supramolecular chiral selectors were mainly done by molecular modelling and nuclear magnetic resonance spectroscopy. Demonstrations were predominantly on drug analysis for the separation of racemates.

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Nuclear magnetic resonance to study the interactions acting in the enantiomeric separation of homocysteine by capillary electrophoresis with a dual system of γ‐cyclodextrin and the chiral ionic liquid EtCholNTf₂

et al. 2019

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The enantiomeric separation of 9‐fluorenylmethoxycarbonyl chloride (FMOC)‐homocysteine (Hcy) by CE was investigated using γ‐CD and the chiral ionic liquid (R)‐(1‐hydroxybutan‐2‐yl)(trimethyl)azanium‐bis(trifluoromethanesulfon)imidate (also called (R)‐N,N,N‐trimethyl‐2‐aminobutanol‐bis(trifluoromethane‐sulfon)imidate) (EtCholNTf2) as chiral selectors. Using 2 mM γ‐CD and 5 mM EtCholNTf2 in 50 mM borate buffer (pH 9), FMOC‐Hcy enantiomers were separated with a resolution value of 3.8. A reversal in the enantiomer migration order in comparison with the single use of γ‐CD in the separation buffer was obtained. Then, NMR experiments were carried out to elucidate the interactions taking place in the enantiomeric separation of FMOC‐Hcy. NMR analyses highlighted the formation of an inclusion complex since the hydrophobic group of FMOC‐Hcy was inserted into the γ‐CD cavity. Moreover, interactions between EtCholNTf2 and γ‐CD were also observed, suggesting that the chiral ionic liquid would also enter the cavity of the γ‐CD.

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Establishment and molecular modeling study of maltodextrin-based synergistic enantioseparation systems with two new hydroxy acid chiral ionic liquids as additives in capillary electrophoresis

Cited by 40 publications

References 41 publications

Advances of capillary electrophoresis enantioseparations in pharmaceutical analysis (2017–2020)

Advances of capillary electrophoresis enantioseparations in pharmaceutical analysis (2017–2020)

Chiral Selectors in Capillary Electrophoresis: Trends during 2017–2018

Nuclear magnetic resonance to study the interactions acting in the enantiomeric separation of homocysteine by capillary electrophoresis with a dual system of γ‐cyclodextrin and the chiral ionic liquid EtCholNTf₂

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Establishment and molecular modeling study of maltodextrin-based synergistic enantioseparation systems with two new hydroxy acid chiral ionic liquids as additives in capillary electrophoresis

Cited by 40 publications

References 41 publications

Advances of capillary electrophoresis enantioseparations in pharmaceutical analysis (2017–2020)

Advances of capillary electrophoresis enantioseparations in pharmaceutical analysis (2017–2020)

Chiral Selectors in Capillary Electrophoresis: Trends during 2017–2018

Nuclear magnetic resonance to study the interactions acting in the enantiomeric separation of homocysteine by capillary electrophoresis with a dual system of γ‐cyclodextrin and the chiral ionic liquid EtCholNTf2

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Nuclear magnetic resonance to study the interactions acting in the enantiomeric separation of homocysteine by capillary electrophoresis with a dual system of γ‐cyclodextrin and the chiral ionic liquid EtCholNTf₂