Porphyrin and galactosyl conjugated micelles for targeting photodynamic therapy

Pharm Res. 2010 Jan;27(1):187-99. doi: 10.1007/s11095-009-9998-8. Epub 2009 Nov 4.

Abstract

Purpose: To study the targeting and photodynamic therapy efficiency of porphyrin and galactosyl conjugated micelles based on amphiphilic copolymer galactosyl and mono-aminoporphyrin (APP) incoporated poly(2-aminoethyl methacrylate)-polycaprolactone (Gal-APP-PAEMA-PCL).

Methods: Poly(2-aminoethyl methacrylate)-polycaprolactone (PAEMA-PCL) was synthesized by the combination of ring opening polymerization and reversible addition-fragmentation chain transfer (RAFT) polymerization, and then Gal-APP-PAEMA-PCL was obtained after conjugation of lactobionic acid and 5-(4-aminophenyl)-10,15,20-triphenylporphyrin (APP) to PAEMA-PCL. The chemical structures of the copolymers were characterized, and their biological properties were evaluated in human laryngeal carcinoma (HEp2) and human hepatocellular liver carcinoma (HepG2) cells.

Results: Both APP-PAEMA-PCL and Gal-APP-PAEMA-PCL did not exhibit dark cytotoxicity to HEp2 cells and HepG2 cells. However, Gal-APP-PAEMA-PCL was taken up selectively by HepG2 cells and had the higher phototoxicity effect. Both polymers preferentially localized within cellular vesicles that correlated to the lysosomes.

Conclusions: The results indicated that porphyrin and galactosyl conjugated polymer micelles exhibited higher targeting and photodynamic therapy efficacy in HepG2 cells than in HEp2 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Asialoglycoprotein Receptor / metabolism
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Carriers / chemical synthesis*
  • Drug Compounding / methods
  • Drug Delivery Systems / methods*
  • Drug Screening Assays, Antitumor
  • Galactose / chemistry*
  • Galactose / pharmacokinetics
  • Galactose / pharmacology
  • Hep G2 Cells
  • Humans
  • Micelles
  • Models, Biological
  • Particle Size
  • Photochemotherapy / methods*
  • Polyesters / chemistry
  • Polymers / chemical synthesis*
  • Porphyrins / chemical synthesis*
  • Porphyrins / pharmacokinetics
  • Porphyrins / pharmacology

Substances

  • Asialoglycoprotein Receptor
  • Drug Carriers
  • Micelles
  • Polyesters
  • Polymers
  • Porphyrins
  • polycaprolactone
  • Galactose