Determination by fluorimetric titration of the ionization constants of ciprofloxacin in solution and in the presence of liposomes

Photochem Photobiol. 2001 Jan;73(1):14-9. doi: 10.1562/0031-8655(2001)073<0014:dbftot>2.0.co;2.

Abstract

A fluorescence titration method was applied for the determination of pKa of ciprofloxacin (CPX) in solution. Values of 6.18 +/- 0.05 and 8.76 +/- 0.03 were obtained for pKa1 and pKa2, respectively. The method was used to determine the ionization constants in the presence of liposomes of dipalmitoylphosphatidylcholine (DPPC) and DPPC with 10 mol% of dipalmitoylphosphatidylglycerol. A dependence on the surface charge of liposomes was found which supported the existence of a basic electrostatic interaction between CPX and the phospholipid bilayer. Both pK values for the N-4 butyl-piperazinyl derivative (BCPX) of the parent compound were also determined in solution and in the presence of liposomes. The competition of both drugs for the same binding site as 1-anilino-8-naphtalene sulfonate demonstrate that the interaction is governed by electrostatic forces.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry
  • Ciprofloxacin / analogs & derivatives
  • Ciprofloxacin / chemistry*
  • Hydrogen-Ion Concentration
  • Liposomes
  • Photochemistry
  • Solutions
  • Spectrometry, Fluorescence
  • Static Electricity

Substances

  • Anti-Infective Agents
  • Liposomes
  • Solutions
  • Ciprofloxacin