Enantioseparation of ofloxacin and its four related substances with ligand exchange–micellar electrokinetic chromatography using copper(II)‐L‐isoleucine complex as chiral selector

Liu, Yongjing; Wang, Xiaoying

doi:10.1002/chir.22705

Cited by 11 publications

(10 citation statements)

References 19 publications

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“…6,7 To that end, several chromatographic methods have reviewed for enantiomeric separation of fluoroquinolones. [8][9][10][11] Most HPLC methods used indirect strategies either by derivatization of GFLX 12 and OFLX [13][14][15][16][17][18][19] or by addition of cyclodexrin in the mobile phase for enantiomeric separation of NFLX. 20,21 Some other researches applied direct enantiomeric separations by using chiral stationary phases (CSPs) like amylosebased CSP 22,23 for GFLX.…”

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confidence: 99%

Structure‐retention relationship for enantioseparation of selected fluoroquinolones

et al. 2018

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Fluoroquinolones are popular class of antibiotics with distinct chemical functionality. Most of them are ampholytes with one chiral center. Stereogeneic center is located either in the side ring of Gatifloxacin (GFLX) or in the quinolone core of Ofloxacin (OFLX). These two amphoteric fluoroquinolones have terminal amino groups in common. The unusual Nadifloxacin (NFLX) is an acidic fluoroquinolone with a core chiral center. Owing to chirality and functionality differences among GFLX, OFLX, and NFLX, we mapped these enantiomers onto structure-retention relationship. Amount of acetic acid modifier was studied in screened mobile phase and cellulose tris(3-chloro-4-methyl phenyl carbamate) (Lux cellulose-2) stationary phase. Experimental design of acetic acid% along with column temperature have been applied. Resolution and enantioselectivity have been related to structural features of the studied enantiomers. High amount of acid (0.4%) was optimum for the separation of either side chirality with a proximate amino group (GFLX) or core chirality without basic functionality (NFLX), while low amount (0.2%) is optimum for core chiral center with distal amino group (OFLX). Temperature has no significant effect on resolution and retention of enantiomers except for OFLX. Enantio-retention explains possible chiral selective and nonselective interactions. The proposed methods have been validated for pharmaceutical analyses.

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confidence: 99%

Structure‐retention relationship for enantioseparation of selected fluoroquinolones

et al. 2018

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“…Indeed, the use of SDS micelles was also critical in the separation of sitafloxacin and its impurities [79]. This was further validated in a report that used copper(II)- l -isoleucine complex with SDS micelles for the simultaneous analysis of ofloxacin enantiomers and six related impurities [78]. It was noted that without SDS, ofloxacin was only partially separated while the impurities were not separated at all.…”

Section: Low Molecular Weight Compoundsmentioning

confidence: 95%

“…Three classes of low molecular weight compounds were reported as CS. These are CS with a central ion (i.e., ligand exchangers [78,79], an ion-pair selector [80]), ILs [31,81,82] and a tetracycline antibiotic [83]. An IL implemented in a ligand exchanger is discussed under ILs.…”

Section: Low Molecular Weight Compoundsmentioning

confidence: 99%

“…Octa(6- O -sulfo)-γ-CD was used in the analysis of different pharmaceutical forms of pindolol, which is formulated as a racemic mixture [41]. Two groups worked independently on the separation of ofloxacin and related substances [33,78]. One group used copper(II)-L-isoleucine complex as CS [78], and the other used various β-CD derivatives, namely, carboxymethyl-β-CD and sulfated-β-CD [33].…”

Section: Applications To Real Samplesmentioning

confidence: 99%

“…Two groups worked independently on the separation of ofloxacin and related substances [33,78]. One group used copper(II)-L-isoleucine complex as CS [78], and the other used various β-CD derivatives, namely, carboxymethyl-β-CD and sulfated-β-CD [33]. Sodium carboxymethyl-β-CD was used in the analysis of betaxolol HCl and propranolol HCl in an inter-instrument reproducibility study that is required in method transfer [47].…”

Section: Applications To Real Samplesmentioning

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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Past, present, and future developments in enantioselective analysis using capillary electromigration techniques

2020

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Past, present, and future developments in enantioselective analysis using capillary electromigration techniques Enantioseparation of chiral products has become increasingly important in a large diversity of academic and industrial applications. The separation of chiral compounds is inherently challenging and thus requires a suitable analytical technique that can achieve high resolution and sensitivity. In this context, CE has shown remarkable results so far. Chiral CE offers an orthogonal enantioselectivity and is typically considered less costly than chromatographic techniques, since only minute amounts of chiral selectors are needed. Several CE approaches have been developed for chiral analysis, including chiral EKC and chiral CEC. Enantioseparations by EKC benefit from the wide variety of possible pseudostationary phases that can be employed. Chiral CEC, on the other hand, combines chromatographic separation principles with the bulk fluid movement of CE, benefitting from reduced band broadening as compared to pressure-driven systems. Although UV detection is conventionally used for these approaches, MS can also be considered. CE-MS represents a promising alternative due to the increased sensitivity and selectivity, enabling the chiral analysis of complex samples. The potential contamination of the MS ion source in EKC-MS can be overcome using partial-filling and counter-migration techniques. However, chiral analysis using monolithic and open-tubular CEC-MS awaits additional method validation and a dedicated commercial interface. Further efforts in chiral CE are expected toward the improvement of existing techniques, the development of novel pseudostationary phases, and establishing the use of chiral ionic liquids, molecular imprinted polymers, and metalorganic frameworks. These developments will certainly foster the adoption of CE(-MS) as a well-established technique in routine chiral analysis.

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Enantioseparation of ofloxacin and its four related substances with ligand exchange–micellar electrokinetic chromatography using copper(II)‐L‐isoleucine complex as chiral selector

Cited by 11 publications

References 19 publications

Structure‐retention relationship for enantioseparation of selected fluoroquinolones

Structure‐retention relationship for enantioseparation of selected fluoroquinolones

Chiral Selectors in Capillary Electrophoresis: Trends during 2017–2018

Past, present, and future developments in enantioselective analysis using capillary electromigration techniques

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