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Enantiomeric Separation of Ofloxacin by Nano-Liquid Chromatography Using a Sulfated-β-Cyclodextrin as a Chiral Selector in the Mobile Phase

[ Vol. 6 , Issue. 3 ]

Author(s):

Noelia Rosales-Conrado, Maria E. Leon-Gonzalez, Anna Rocco and Salvatore Fanali   Pages 209 - 216 ( 8 )

Abstract:


The S-(-)-enantiomer of ofloxacin, a chiral fluoroquinolone antibiotic, exhibits an antibacterial activity 8-128 times higher than that of the R-(+)-isomer. A new stereospecific nano-LC method for the enantioseparation of the ofloxacin racemic mixture was developed using an achiral reversed phase column (Pinnacle II Phenyl 3 μm, 15 cm x 100 μm ID) and heptakis-(2,3-diacetyl-6-sulfo)-β-cyclodextrin (HDAS-β-CD) as a mobile phase chiral additive. Best enantioresolution was achieved using a mobile phase containing acetonitrile, 50 mM sodium acetate buffer pH 3 (30:70, v/v) and 5 mM of HDAS-β-CD. The flow rate thorough the capillary column was estimated in 620 nL/min and the wavelength for the UV detection was set at 290 nm. Good separation of the enantiomers was obtained is less than 10 min with a resolution and selectivity factor of 1.66 and 1.88, respectively. The effect of several experimental parameters on the chiral separation was also evaluated and the method was successfully validated in terms of linearity, accuracy and precision, showing the enantiorecognition capability of the employed sulfated β-CD toward the ofloxacin chiral drug.

Keywords:

Chiral separation, β-cyclodextrin, Nano-liquid chromatography, Ofloxacin, Fluoroquinolone antibiotics

Affiliation:

Institute of Chemical Methodologies, Consiglio Nazionale delle Ricerche, Area della Ricerca di Roma I, 00015 Monterotondo Scalo, Rome, Italy.



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