Synthesis and evaluation of a novel lipophilic folate receptor targeting ligand

Anticancer Res. 2011 May;31(5):1521-5.

Abstract

Background: Folate receptor (FR)-targeted liposomes have been investigated as delivery vehicles for anticancer drugs. A novel lipophilic FR ligand, folate-glutathione-polyethyleneglycol-distearoyl phosphatidylethanolamine (F-GSH-PEG-DSPE), was synthesized, incorporated into liposomes and evaluated for FR targeting efficiency. These liposomes were then evaluated as carriers of the chemotherapy agent vincristine (VIN).

Materials and methods: F-GSH-PEG-DSPE was synthesized and FR-targeted liposomes loaded with either calcein (F-L-Calcein) or VIN (F-L-VIN) were prepared by thin film hydration followed by polycarbonate membrane extrusion and, in the case of VIN, by remote loading. To assess liposome stability, the uptake of F-L-VIN in KB (FR+) cancer cells was measured after storage under 4°C for 3 months. Comparative pharmacokinetic studies were carried out with F-L-VIN and L-VIN (non-targeted control liposomes).

Results: F-L-Calcein showed significantly higher cellular uptake in KB cells compared to non-targeted liposomes. In addition, F-L-VIN showed enhanced cytotoxicity in KB cells in vitro compared to control liposomes. Pharmacokinetic parameters indicated that both F-L-VIN and control liposomes had higher area under the curve (AUC), mean residence time (MRT), elimination half life (t1/2-β) and lower total body clearance (CL) than those of free VIN, while there were no significant differences between these liposomal formulations.

Conclusion: F-GSH-PEG-DSPE is effective as a novel ligand for the synthesis of FR-targeted liposomes.

Publication types

  • Evaluation Study
  • Research Support, N.I.H., Extramural

MeSH terms

  • Antineoplastic Agents, Phytogenic / pharmacokinetics
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Survival / drug effects
  • Drug Delivery Systems*
  • Fluoresceins / administration & dosage
  • Fluoresceins / pharmacokinetics
  • Folate Receptors, GPI-Anchored / metabolism*
  • Folic Acid / analogs & derivatives*
  • Folic Acid / chemical synthesis
  • Folic Acid / chemistry*
  • Folic Acid / metabolism
  • Folic Acid / pharmacokinetics
  • Folic Acid / pharmacology
  • Humans
  • KB Cells
  • Ligands
  • Liposomes*
  • Phosphatidylethanolamines / chemical synthesis*
  • Phosphatidylethanolamines / chemistry*
  • Phosphatidylethanolamines / metabolism
  • Phosphatidylethanolamines / pharmacokinetics
  • Phosphatidylethanolamines / pharmacology*
  • Polyethylene Glycols / chemistry*
  • Polyethylene Glycols / metabolism
  • Protein Binding
  • Tissue Distribution
  • Vincristine / pharmacokinetics
  • Vincristine / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Fluoresceins
  • Folate Receptors, GPI-Anchored
  • Ligands
  • Liposomes
  • Phosphatidylethanolamines
  • folate-glutathione-polyethyleneglycol-distearoyl phosphatidylethanolamine
  • polyethylene glycol-distearoylphosphatidylethanolamine
  • Polyethylene Glycols
  • Vincristine
  • Folic Acid
  • fluorexon