Analytical chiral separation of a new quinolone compound in biological fluids by high-performance liquid chromatography

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

“…Consequently, their differentiation and, in particular, chromatographic separation are not possible in achiral environments. Some HPLC methods have been developed to introduce chirality in the process either directly using a chiral stationary phase (CSP) or indirectly by derivatization of analytes with a chiral reagent or addition of chiral additives to the mobile phase [121]. 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.…”

“…As an alternative to the derivatization of the carboxyl group, the amine function was shown to be more effective in some fluoroquinolones because the distance to the chiral centre of the enantiomers is shorter. 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].…”

“…Lehr and Damn [146] developed a method to quantify (R)-ofloxacin and its S-enantiomer (LEV) in biologic fluids by using a CSP with bovine serum albumin immobilized on silica gel. Another protein-based column consisted of an ovomucoid conjugated to aminopropyl silica gel and it was used for the separation of racemic TEM in serum and urine, reported by Matsuoka et al [121]. In both methods the chromatography was performed with a neutral or basic mobile phase.…”

Chiral separation of quinolones by liquid chromatography and capillary electrophoresis

“… and Matsuoka et al. utilized secondary amino function of a 7‐piperazine substituent of fluoroquinolones to prepare diastereomeric derivatives of lomefloxacin two steps synthesis. The diastereomers were then chromatographied on a silica column under normal phase conditions.…”

“…Matsuoka et al. reported a chiral method for temafloxacin enantiomers using an ovomucoid CSP. To eliminate peak asymmetry and achieve baseline separation, they had derivatized the free carboxylic and amino groups of the investigated quinolone.…”