Separation and characterization of ciprofloxacin, difloxacin, lomefloxacin, norfloxacin, and ofloxacin oxidation products under potassium permanganate treatment in acidic medium by UPLC-MS/MS

Talanta. 2013 May 15:109:91-100. doi: 10.1016/j.talanta.2013.01.055. Epub 2013 Feb 5.

Abstract

A simple, sensitive and reproducible ultra-performance liquid chromatography method for determination of ciprofloxacin, difloxacin, lomefloxacin, norfloxacin and ofloxacin oxidation stability under permanganate treatment in acidic conditions at pH from 3.0 to 6.0, was developed. Chromatographic separations were carried out using the Acquity UPLC BEH C18 column; (2.1×100 mm, 1.7 μm particle size). The column was maintained at 40°C, and eluted under isocratic conditions using 83% of eluent A and 17% of eluent B over 6.5 min, at a flow rate of 0.3 mL min(-1). Eluent A: water/formic acid (0.1 v/v%); eluent B: acetonitrile/formic acid (0.1 v/v%). An oxidation process followed kinetic of the second order reaction and depended upon solution acidity. Oxidation of fluoroquinolones proceeded at piperazine moiety yielding respective hydroxy and oxo analogs, and remaining the quinolone fragment intact. Structures of products formed were assigned on a basis of UPLC/MS/MS fragmentation pathways.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Chromatography, Liquid / instrumentation
  • Chromatography, Liquid / methods*
  • Drug Stability
  • Fluoroquinolones / chemistry
  • Fluoroquinolones / isolation & purification*
  • Hydrogen-Ion Concentration
  • Limit of Detection
  • Molecular Structure
  • Oxidation-Reduction
  • Potassium Permanganate / chemistry*
  • Reproducibility of Results
  • Solutions
  • Tandem Mass Spectrometry / instrumentation
  • Tandem Mass Spectrometry / methods*

Substances

  • Anti-Bacterial Agents
  • Fluoroquinolones
  • Solutions
  • Potassium Permanganate