Use of various ß-cyclodextrin derivatives as chiral selectors for the enantiomeric separation of ofloxacin and its five related substances by capillary electrophoresis.

ABSTRACT

A capillary electrophoretic method for the enantioseparation of ofloxacin and its five related substances (potential impurities, indicated as impurities B-F) was developed using ß-cyclodextrin derivatives as chiral selectors. To our knowledge, there are no previous studies about using capillary electrophoresis for the separation of impurities B-D. Six ß-cyclodextrin derivatives including cationic (piperidine- and cyclohexylamine-), neutral (dimethyl- and hydroxypropyl-), and anionic (carboxymethyl- and sulfated-) ß-cyclodextrin derivatives were tested and operational parameters such as buffer pH and concentration of ß-cyclodextrin derivatives were investigated. The best resolutions were all obtained with anionic ß-cyclodextrin derivatives ofloxacin, impurities C-F could be best resolved with carboxymethyl-ß-cyclodextrin at satisfactory resolutions of 8.27, 9.98, 5.92, 8.49 and 6.78, respectively, while for impurity B, a particularly impressive resolution value, up to 21.38, was observed using sulfated-ß-cyclodextrin. The enhancement of enantioseparation observed for the tested analytes using anionic ß-cyclodextrin derivatives might be due to some favorable interaction between selectors and analytes. Given the fact that the selection of chiral selector depends on the structures of analytes, with the help of structural similarities and differences of the analytes, the structure-separation relationship was further discussed.