Copper-topotecan complexation mediates drug accumulation into liposomes

J Control Release. 2006 Aug 10;114(1):78-88. doi: 10.1016/j.jconrel.2006.05.019. Epub 2006 Jun 2.

Abstract

These studies describe the role of transition metal ions in the liposomal encapsulation of topotecan. Liposomes (1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC) and cholesterol (CH) (55:45, mole ratio)) were prepared with manganese (Mn), copper (Cu), zinc (Zn) or cobalt (Co) ion gradients (metal inside). Subsequently, topotecan was added to the liposome exterior (final drug-to-lipid ratio (mol/mol) of 0.2) and drug encapsulation was measured as a function of time and temperature. No drug loading was achieved with liposomes containing Co or Zn. Topotecan could be encapsulated into Mn-containing liposomes only in the presence of the ionophore, A23187 suggesting that a transmembrane pH gradient was necessary. However, Cu-containing liposomes, in the presence or absence of an imposed pH gradient, efficiently encapsulated topotecan. It has been reported that Cu(II) can form transition metal complexes with camptothecin; therefore, the Cu-topotecan interaction was characterized in solution as a function of pH. These investigations demonstrated that topotecan inhibited formation of an insoluble Cu hydroxide precipitate. Cryo-TEM analysis of the topotecan-loaded Cu liposomes showed electron-dense intravesicular precipitates. Further studies demonstrated that only the active lactone form of the drug was encapsulated and this form predominated in Cu-containing liposomes. Copper complexation reactions define a viable methodology to prepare liposomal camptothecin formulations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Buffers
  • Calcimycin / chemistry
  • Cations, Divalent / chemistry
  • Chemical Precipitation
  • Cholesterol / chemistry
  • Copper / chemistry*
  • Cryoelectron Microscopy
  • Doxorubicin / chemistry
  • Drug Compounding / methods
  • Hydrogen-Ion Concentration
  • Lactones / chemistry
  • Liposomes / chemistry*
  • Manganese Compounds / chemistry
  • Molecular Structure
  • Nigericin / chemistry
  • Phosphatidylcholines / chemistry
  • Proton-Motive Force
  • Sulfates / chemistry
  • Topotecan / chemistry*

Substances

  • Buffers
  • Cations, Divalent
  • Lactones
  • Liposomes
  • Manganese Compounds
  • Phosphatidylcholines
  • Sulfates
  • Calcimycin
  • Copper
  • Topotecan
  • Doxorubicin
  • Cholesterol
  • 1,2-distearoyllecithin
  • Nigericin
  • manganese sulfate