title: Preparative resolution of gatifloxacin enantiomers with pre-column esterification strategy and comparing their enantioselectivity to bacteria and antibody.
abstract: Gatifloxacin (GFX) is a kind of chiral fluoroquinolones compound due to the methyl group at the C-3 position of the piperazine ring[1]. Although the enantiomers of GFX show similar levels of antimicrobial activity and pharmacokinetics[2], the other biological activities (i.e., toxicity or enantioselective recognition to various receptors in vivo) of GFX enantiomers have not yet been studied. With this in mind, we developed a rapid and cost-effective high performance liquid chromatographic (HPLC) separation procedure for GFX enantiomers with a pre-column esterification strategy. With significant enhancement of drug solubility and optimization for chromatographic conditions, the proposed method was scaled up to preparative HPLC to obtain optical active S-(-)- and R-(+)-GFX. The antibacterial activities of GFX enantiomers after preparative separation were further verified by measuring the Minimum Inhibitory Concentration (MIC) values against Escherichia coli ATCC 25922. In addition, the binding selectivity of GFX enantiomers to protein receptor were evaluated by antibody using enzyme-linked immunosorbent assay (ELISA) for the first time.
authors.affiliation: Key Risk Assessment Laboratory of Agricultural Product Preservation, Ministry of Agriculture/Guangdong Provincial Key Laboratory of Food Quality and Safety, South China Agricultural University, Guangzhou 510642, Guangdong, China.
authors.forename: Chi Jian
authors.initials: CJ
authors.lastname: Zhang
authors.affiliation: Key Risk Assessment Laboratory of Agricultural Product Preservation, Ministry of Agriculture/Guangdong Provincial Key Laboratory of Food Quality and Safety, South China Agricultural University, Guangzhou 510642, Guangdong, China.
authors.forename: Hong Tao
authors.initials: HT
authors.lastname: Lei
authors.affiliation: Key Risk Assessment Laboratory of Agricultural Product Preservation, Ministry of Agriculture/Guangdong Provincial Key Laboratory of Food Quality and Safety, South China Agricultural University, Guangzhou 510642, Guangdong, China.
authors.forename: Xiao Long
authors.initials: XL
authors.lastname: Huang
authors.affiliation: College of Sciences, South China Agricultural University, Guangzhou 510642, Guangdong, China.
authors.forename: Ying Ju
authors.initials: YJ
authors.lastname: Liu
authors.affiliation: College of Life Science, Shaanxi Normal University, Xi'an 710062, Shaanxi, China.
authors.forename: Kai
authors.initials: K
authors.lastname: Cai
authors.affiliation: Key Risk Assessment Laboratory of Agricultural Product Preservation, Ministry of Agriculture/Guangdong Provincial Key Laboratory of Food Quality and Safety, South China Agricultural University, Guangzhou 510642, Guangdong, China.
authors.forename: Zhen Lin
authors.initials: ZL
authors.lastname: Xu
authors.affiliation: Key Risk Assessment Laboratory of Agricultural Product Preservation, Ministry of Agriculture/Guangdong Provincial Key Laboratory of Food Quality and Safety, South China Agricultural University, Guangzhou 510642, Guangdong, China.
authors.forename: Yuan Ming
authors.initials: YM
authors.lastname: Sun
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects*; D004951:Esterification; D024841:Fluoroquinolones / Q000737:chemistry* / Q000494:pharmacology*; D000077734:Gatifloxacin; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D024841:Fluoroquinolones; D000077734:Gatifloxacin