A novel family of L-amino acid-based biodegradable polymer-lipid conjugates for the development of long-circulating liposomes with effective drug-targeting capacity

Bioconjug Chem. 2003 Nov-Dec;14(6):1156-64. doi: 10.1021/bc0340363.

Abstract

The objective of this study was to develop biodegradable polypeptide-lipid conjugates for the design of polymer-coated long-circulating liposomes (LCL). Lipid conjugates of poly(hydroxyalkyl L-asparagine/L-glutamine) were synthesized and incorporated into 0.15 microm dipalmitoyl phosphatidylcholine (DPPC)-cholesterol liposomes. Circulation times and biodistribution were assessed in rats using a radioactive lipid marker. Evaluation of the therapeutic activity of prednisolone phosphate loaded in 0.1 microm PHEA-DPPC-cholesterol liposomes in a rat experimental arthritis model was performed to demonstrate the drug-targeting potential of the polymer-coated liposomes. Coating of liposomes with poly(hydroxyethyl L-asparagine) (PHEA) and poly(hydroxyethyl L-glutamine) (PHEG) extended the circulation half-life to a similar extent as poly(ethylene glycol) (PEG), which is normally used for the preparation of LCL. Glutamine polymers with a hydroxypropyl or a hydroxybutyl group instead of hydroxyethyl group also yield prolonged circulation, however, not to the same extent as PHEA/G. The pharmacokinetic properties of PHEA-liposomes were independent of the lipid dose even at very low lipid doses of around 50 nmol per rat. PLP was successfully entrapped in PHEA-liposomes. These liposomes were shown to be stable in the circulation and equally effective in rat experimental arthritis as PLP encapsulated in PEG-liposomes. PHEA and PHEG are attractive alternative polymers for the design of LCL: their performance is similar to that of PEG-liposomes but they have the advantage of being biodegradable.

MeSH terms

  • 1,2-Dipalmitoylphosphatidylcholine / chemistry
  • 1,2-Dipalmitoylphosphatidylcholine / pharmacokinetics
  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry*
  • Animals
  • Anti-Inflammatory Agents / pharmacokinetics
  • Arthritis, Experimental / drug therapy
  • Biodegradation, Environmental
  • Drug Delivery Systems*
  • Half-Life
  • Lipids / chemistry*
  • Liposomes / chemistry*
  • Liposomes / metabolism
  • Liposomes / pharmacokinetics
  • Male
  • Molecular Structure
  • Polyethylene Glycols / chemistry
  • Polyethylene Glycols / pharmacokinetics
  • Polymers / chemical synthesis
  • Polymers / chemistry*
  • Rats
  • Rats, Inbred Lew
  • Rats, Wistar
  • Tissue Distribution

Substances

  • Amino Acids
  • Anti-Inflammatory Agents
  • Lipids
  • Liposomes
  • Polymers
  • 1,2-Dipalmitoylphosphatidylcholine
  • Polyethylene Glycols