Synthesis and characterization of a PAMAM-OH derivative containing an acid-labile β-thiopropionate bond for gene delivery

Int J Pharm. 2016 Jul 25;509(1-2):314-327. doi: 10.1016/j.ijpharm.2016.05.060. Epub 2016 May 31.

Abstract

The present report describes the synthesis of a hydroxyl terminal PAMAM dendrimer (PAMAM-OH) derivative (PAMSPF). The hydroxyls of PAMAM-OH were attached to S-Methyl-l-cysteine (SMLC) via an acid-labile ester bond, named as β-thiopropionate bond, followed by modification with folic acid (FA) through a polyethylene glycol (PEG) linker. The degrees of attachment of SMLC and FA to the PAMAM-OH backbone were 83.9% and 12.8%, respectively. PAMSPF could condense DNA to form spherical nanoparticles with particle sizes of ∼200nm and remain stable in the presence of heparin and nuclease. The β-thiopropionate bond in PAMSPF was hydrolyzed completely and the DNA release rate was 95.8±3.3% after incubation under mildly acidic conditions at 37°C for 3h. PAMSPF/DNA was less cytotoxic to KB and HepG2 cells and exhibited a higher gene transfection efficiency than native PAMAM/DNA. The uptake assays showed that PAMSPF/DNA entered KB cells within 0.5h through folate receptor-mediated endocytosis and escaped from endosomes within 2h. In addition, PAMSPF/DNA displayed long circulation time along with excellent targeting of tumor sites in vivo. These findings demonstrate that PAMSPF is an excellent carrier for safe and effective gene delivery.

Keywords: Acid-labile polymer; Cytotoxicity; Gene delivery; PAMAM-OH; Transfection; β-thiopropionate.

MeSH terms

  • Acids / chemistry*
  • Animals
  • Cell Line, Tumor
  • Cysteine / analogs & derivatives*
  • Cysteine / chemistry
  • DNA / chemistry
  • Dendrimers / chemistry*
  • Endocytosis / drug effects
  • Female
  • Folic Acid / chemistry
  • Gene Transfer Techniques
  • Genetic Therapy / methods
  • Hep G2 Cells
  • Humans
  • KB Cells
  • Mice
  • Mice, Inbred BALB C
  • Mice, Nude
  • Nanoparticles / chemistry
  • Particle Size
  • Polyethylene Glycols / chemistry
  • Transfection / methods

Substances

  • Acids
  • Dendrimers
  • PAMAM Starburst
  • Polyethylene Glycols
  • 3-mercaptopyruvic acid
  • DNA
  • Folic Acid
  • Cysteine