Amphiphilic polyesters bearing pendant sugar moieties: synthesis, characterization, and cellular uptake

Carbohydr Polym. 2014 Jan:99:710-9. doi: 10.1016/j.carbpol.2013.08.098. Epub 2013 Sep 8.

Abstract

Ring-opening polymerization (ROP) and "click" reactions were used to prepare a series of amphiphilic block-graft (PαN₃CL-g-Sugar)-b-PCL polymers. The glycosylated RO-(PαN₃CL-g-Sugar)-b-PCL polymers formed micelles with critical micelle concentrations (CMCs) in the range of 4.9-23.2 mg L(-1) in the aqueous phase. The mean diameters of the micelles were between 21 nm and 125 nm, considerably lower than the 200 nm diameter at which the uptake of micelles by the reticuloendothelial cells becomes compromised. Selective lectin-binding experiments confirmed that glycosylated RO-(PαN₃CL-g-Sugar)-b-PCL can be used in biorecognition applications, and in vitro cell-viability assay showed that RO-(PαN₃CL-g-Sugar)-b-PCL has low cytotoxicity. Micelles loaded with doxorubicin (DOX) facilitated an improved uptake of DOX by HeLa cells that was completed within 1h, and the endocytosed-DOX successfully reached intracellular compartments and entered nuclei.

Keywords: Block-graft polymer; Cellular uptake; Drug delivery; Glycopolymer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / pharmacology*
  • Cell Survival / drug effects
  • Doxorubicin / chemistry
  • Doxorubicin / pharmacology*
  • Drug Carriers / chemical synthesis*
  • Drug Compounding
  • Endocytosis
  • HeLa Cells
  • Humans
  • Micelles
  • Particle Size
  • Polyesters / chemistry*
  • Polysaccharides / chemistry*

Substances

  • Antibiotics, Antineoplastic
  • Drug Carriers
  • Micelles
  • Polyesters
  • Polysaccharides
  • polycaprolactone
  • Doxorubicin