pH-dependent association of SN-38 with lipid bilayers of a novel liposomal formulation

Int J Pharm. 2005 Aug 11;299(1-2):92-9. doi: 10.1016/j.ijpharm.2005.04.028.

Abstract

The aim of this study was to determine the location of SN-38 molecules in a liposomal formulation as a function of pH. Steady-state fluorescence polarization anisotropy and gel filtration studies of blank (placebo) liposomes, liposomes containing SN-38 and SN-38 solutions (in some cases suspensions) were conducted before lyophilization and after re-hydration at different pH conditions. SN-38, l-(4-trimethylammoniumphenyl)-6-phenyl-l,3,5-hexatriene p-toluenesulfonate (TMA-DPH), N-((4-(6-phenyl-l,3,5-hexatrienyl)phenyl)propyl)trimethylammonium p-toluenesulfonate (TMAP-DPH) and l,6-diphenyl-l,3,5-hexatriene (DPH) were used as fluoroprobes in the polarization anisotropy measurements. The localization of SN-38 was governed by the degree of hydrophobicity of the drug molecules. At high pH, SN-38 is in its inactive, hydrophilic form and partitioned into the water phase of the liposome suspensions. In lyophilized LE-SN38 liposomes re-hydrated with low pH buffer, SN-38 was found at the water-lipid interface of the bilayer.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Camptothecin / analogs & derivatives*
  • Camptothecin / chemistry
  • Cardiolipins / chemistry
  • Cholesterol / chemistry
  • Chromatography, Gel
  • Diphenylhexatriene / analogs & derivatives
  • Fluorescence Polarization
  • Fluorescent Dyes
  • Hydrogen-Ion Concentration
  • Hydrophobic and Hydrophilic Interactions
  • Irinotecan
  • Lipid Bilayers / chemistry*
  • Liposomes / chemistry*
  • Particle Size
  • Phosphatidylcholines / chemistry
  • Temperature
  • Topoisomerase I Inhibitors

Substances

  • Antineoplastic Agents, Phytogenic
  • Cardiolipins
  • Fluorescent Dyes
  • Lipid Bilayers
  • Liposomes
  • Phosphatidylcholines
  • Topoisomerase I Inhibitors
  • Diphenylhexatriene
  • 1-(4-(trimethylamino)phenyl)-6-phenylhexa-1,3,5-triene
  • Irinotecan
  • Cholesterol
  • 1,2-oleoylphosphatidylcholine
  • Camptothecin