title: Electrophoretic behavior and pKa determination of quinolones with a piperazinyl substituent by capillary zone electrophoresis.
abstract: Electrophoretic behavior and pKa determination of six quinolones with a piperazinyl substituent, together with two quinolones without a piperazinyl substituent and 1-phenylpiperazine, were investigated by capillary zone electrophoresis. The results indicate that quinolones with a piperazinyl substituent involve three protonation/deprotonation equilibria. The results also suggest that the contribution of the zwitterionic species of these quinolones to the effective mobility may not be neglected. This is probably due to a slightly incomplete protonation of the piperazinyl moiety in the pH range of 6.0-8.0, compared with the complete dissociation of the carboxylic group. Consequently, the zwitterionic species of ciprofloxacin, in particular, is slightly negatively charged. With the aid of computer simulation, three pKa values were determined for quinolones with a piperazinyl substituent, thus allowing us to rationalize precisely the influence of pH on the electrophoretic behavior of these compounds.
authors.affiliation: Department of Chemistry, National Taiwan University, Taipei, Taiwan. celin@ntu.edu.tw
authors.forename: Ching-Erh
authors.initials: CE
authors.lastname: Lin
authors.forename: Yan-
authors.initials: Y
authors.lastname: Deng
authors.forename: Wei-Ssu
authors.initials: WS
authors.lastname: Liao
authors.forename: Shao-Wen
authors.initials: SW
authors.lastname: Sun
authors.forename: Wann-Yin
authors.initials: WY
authors.lastname: Lin
authors.forename: Chia-Chong
authors.initials: CC
authors.lastname: Chen
mesh_terms: D019075:Electrophoresis, Capillary / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D010879:Piperazines / Q000737:chemistry*; D015363:Quinolones / Q000032:analysis*
chemical_list: D010879:Piperazines; D015363:Quinolones