Effects of hydroxypropyl-beta-cyclodextrin on the chemical stability of a naphthoquinone in aqueous solutions

Pharmazie. 2003 Jan;58(1):32-7.

Abstract

2-Hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine (1), an antibacterial agent, was shown to form inclusion complexes with HP-beta-CD in aqueous solution. In the present work the kinetics of 1 degradation in aqueous buffer solution was investigated as a function of pH (2.34-3.95), HP-beta-CD concentration (0%-28% (w/v)) and temperature (60-90 degrees C). A second-order derivative spectroscopic methodology was developed for the kinetic investigations. The degradation showed to follow pseudo-first-order kinetics. Also, an specific acid catalysis was found and the introduction of up to 28% (w/v) HP-beta-CD to the reaction medium did not change this kinetic behaviour. The obtained results indicated that HP-beta-CD stabilises 1 against degradation in aqueous solutions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Hydroxypropyl-beta-cyclodextrin
  • Buffers
  • Chromatography, High Pressure Liquid
  • Cyclodextrins / chemistry*
  • Drug Stability
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Kinetics
  • Naphthoquinones / chemistry*
  • Reproducibility of Results
  • Solutions
  • Spectrophotometry, Ultraviolet
  • Temperature
  • beta-Cyclodextrins*

Substances

  • Buffers
  • Cyclodextrins
  • Naphthoquinones
  • Solutions
  • beta-Cyclodextrins
  • 2-Hydroxypropyl-beta-cyclodextrin