High-performance liquid chromatographic separation of fluoroquinolone enantiomers: a review

Grellet, Jean; Ba, Burrows; Saux, Marie-Claude

doi:10.1016/s0165-022x(02)00116-1

Cited by 36 publications

(35 citation statements)

References 19 publications

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“…2). As a consequence, these compounds may exist as racemates, enantiomers or diastereoisomers [144]. Enantiomers of chiral drugs often exhibit different pharmacokinetic and pharmacodynamic properties that may induce different clinical responses.…”

Section: Chromatographic Separationmentioning

confidence: 99%

“…In the derivatization strategy the enantiomers are derivatized before chromatography using a pure chiral reagent to form a mixture of diastereoisomers with distinct physicochemical properties allowing separation in a conventional achiral HPLC column. Taking advantage of the carboxyl group of the fluoroquinolones, some authors have used chiral amines to form diastereoisomers, after activation of that carboxylic function [144]. Lehr and Damn [146] describe a chromatographic method for the determination of (R)-ofloxacin and (S)-ofloxacin (usually named as LEV, and 8 to 128 times more potent in vitro than the R-enantiomer) by coupling L-leucinamide to the enantiomers via diphenylphosphinyl chloride activation.…”

Section: Chromatographic Separationmentioning

confidence: 99%

“…Matsuoka et al [121] investigated the separation of TEM enantiomers by coupling the chiral reagent (S)-(−)-N-1-(2-naphthylsulphonyl)-2-pyrrolidine carbonylchloride (L-NSCP) to their piperazine group. The other indirect strategy to quantify separately each enantiomer involves the use of a chiral ligand and a suitable transition metal ion in the mobile phase [144]. These chiral mobile phase additives interact with enantiomers during their passage through the column by an exchange mechanism, forming diastereomeric complexes that can be easily separated on conventional reversedphase columns [120,134,144].…”

Section: Chromatographic Separationmentioning

confidence: 99%

See 2 more Smart Citations

Analytical methods for determination of new fluoroquinolones in biological matrices and pharmaceutical formulations by liquid chromatography: a review

et al. 2012

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Fluoroquinolones are one of the most promising and intensively studied drugs of contemporary anti-infective chemotherapy. New fluoroquinolone antibacterials with improved pharmacokinetic properties and a broad spectrum of activity have been developed, opening new windows of opportunity for clinical use. To our knowledge, no comprehensive and critical review of the analytical methods for the determination of these agents, which correspond to the third- and fourth-generation quinolones, has yet been published. This work summarizes for the first time most of the liquid chromatographic methods reported in the literature for the separation and quantification of the new fluoroquinolones in biological matrices and pharmaceutical formulations. A systematic and detailed survey of physicochemical properties, sample preparation procedures, and chromatographic and detection conditions is presented herein. In the course of this review several liquid chromatographic methods are discussed: reversed-phase high-performance liquid chromatography (RP-HPLC), ion-exchange high-performance liquid chromatography (IEX-HPLC), hydrophilic interaction liquid chromatography (HILIC), high-performance thin-layer chromatography (HPTLC) and other chiral chromatographic methods. Their advantages, applicability and limitations are also examined.

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Section: Chromatographic Separationmentioning

confidence: 99%

Section: Chromatographic Separationmentioning

confidence: 99%

Section: Chromatographic Separationmentioning

confidence: 99%

See 1 more Smart Citation

Analytical methods for determination of new fluoroquinolones in biological matrices and pharmaceutical formulations by liquid chromatography: a review

et al. 2012

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“…Fluoroquinolone enantiomers have been separated on cellulose, protein, or crown ether-based CSPs [4]. Especially, fluoroquinolone enantiomers containing a primary amino functional group have been successfully separated on crown ether-based CSPs.…”

Section: Introductionmentioning

confidence: 99%

HPLC of fluoroquinolone antibacterials using chiral stationary phase based on enantiomeric (3,3′‐diphenyl‐1,1′‐binaphthyl)‐20‐crown‐6

Cho

Han

Hyun³

2009

J of Separation Science

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A residual silanol group-protecting chiral stationary phase (CSP) based on optically active (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 was successfully applied to the resolution of fluoroquinolone compounds including gemifloxacin mesylate. The chiral recognition ability of the residual silanol group-protecting CSP was generally greater than that of the residual silanol group-containing CSP. From these results, it was concluded that the simple protection of the residual silanol groups of the latter CSP with lipophilic n-octyl groups can improve its chiral recognition ability for the resolution of racemic fluoroquinolone compounds. The chromatographic resolution behaviors were investigated as a function of the content and type of organic and acidic modifiers and the ammonium acetate concentration in aqueous mobile phase and the column temperature. Especially, the addition of ammonium acetate to the mobile phase was found to be a quite effective means of reducing the enantiomer retentions without sacrificing the chiral recognition efficiency of the CSP.

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“…In order to prepare a new compound medicine, it is necessary to analyse fluorinated quinolone antibacterials. The methods available for fluorinated quinolone antibacterials assays are thin-layer chromatography (TLC)-fluorescence (Simonovska et al, 1999;Novakovic et al, 2001;Riesbeck and Forsgren, 1994), capillary electrophoresis-UV or fluorescence (Faria et al, 2006;Awadallah et al, 2003;Schmitt-Kopplin et al, 1999), high-performance liquid chromatography (HPLC)-UV or fluorescence (Grellet et al, 2002;Carlucci, 1998;Gasparrini et al, 2001;Lee and Hong, 2000;Brodfuehrer et al, 1998). The majority of these methods were developed to analyse fluorinated quinolone antibacterials in biological samples such as serum or urine, residues in fish and meat or medicine tablets.…”

Section: Introductionmentioning

confidence: 99%

Determination of fluorinated quinolone antibacterials by ion chromatography with fluorescence detection

Zhang

Zhou

et al. 2007

J. Zhejiang Univ. - Sci. B

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For preparing fluorinated quinolone antibiotic medicine locally used in stomatology, simultaneous determination of norfloxacin, ciprofloxacin, and enoxacin was carried out by multiphase ion chromatography with fluorescence detection. Quinolone antibiotics were separated by Dionex OmniPac PAX-500 column with an eluent of 15 mmol/L H 2 SO 4 and 35% methanol (v/v) at a flow-rate of 1.0 ml/min and detected with fluorescence with excitation and emission wave lengths of 347 nm and 420 nm respectively. The detection limits (S/N=3) of norfloxacin, ciprofloxacin and enoxacin were 50, 105 and 80 ng/ml respectively. The relative standard deviations of retention time, peak area and peak height were less than 1.1% and good linear relationship resulted. The developed method was applied to pharmaceutical formulations and biological fluids.

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High-performance liquid chromatographic separation of fluoroquinolone enantiomers: a review

Cited by 36 publications

References 19 publications

Analytical methods for determination of new fluoroquinolones in biological matrices and pharmaceutical formulations by liquid chromatography: a review

Analytical methods for determination of new fluoroquinolones in biological matrices and pharmaceutical formulations by liquid chromatography: a review

HPLC of fluoroquinolone antibacterials using chiral stationary phase based on enantiomeric (3,3′‐diphenyl‐1,1′‐binaphthyl)‐20‐crown‐6

Determination of fluorinated quinolone antibacterials by ion chromatography with fluorescence detection

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