The effect of stationary phase on lipophilicity determination of beta-blockers using reverse-phase chromatographic systems

Biomed Chromatogr. 2005 Dec;19(10):725-36. doi: 10.1002/bmc.507.

Abstract

Evaluation of lipophilicity parameters for basic compounds using different chromatographic stationary phases is presented. An HPLC method for determination of lipophilic molecule-stationary phase interactions was based on gradient analysis. Differences in correlation between the lipophilicity of compounds and experimental chromatographic results obtained in pseudo-membrane systems showed a strong influence of stationary phase structure and physico-chemical properties. beta-Blocker drugs with varying lipophilicity and bio-activity were chosen as test compounds. The stationary phases used for the study were monolithic rod-structure C18 and silica gel octadecyl phase SG-C18 as reference material. The second group was silica gel-based polar-embedded alkylamide and cholesterolic phases. The mobile phase was composed of acetonitrile or methanol with ammonium acetate, and a linear gradient of methanol and acetonitrile in mobile phase was performed. A linear correlation of plots of log k(g) = f(log P) was observed, especially for polar-embedded phases, and this allowed log P(HPLC) to be calculated. The behavior of stationary phases in methanol and acetonitrile buffer showed differences between obtained log P(HPLC) values.

MeSH terms

  • Adrenergic beta-Antagonists / analysis
  • Adrenergic beta-Antagonists / chemistry*
  • Chromatography, High Pressure Liquid / instrumentation
  • Chromatography, High Pressure Liquid / methods*
  • Hydrophobic and Hydrophilic Interactions
  • Lipids / chemistry*
  • Mexiletine / analysis
  • Mexiletine / chemistry
  • Propanolamines / analysis
  • Propanolamines / chemistry*
  • Quantitative Structure-Activity Relationship

Substances

  • Adrenergic beta-Antagonists
  • Lipids
  • Propanolamines
  • Mexiletine