Redox-Sensitive Micelles Based on O,N-Hydroxyethyl Chitosan-Octylamine Conjugates for Triggered Intracellular Delivery of Paclitaxel

Mol Pharm. 2016 Jun 6;13(6):1750-62. doi: 10.1021/acs.molpharmaceut.5b00696. Epub 2016 May 6.

Abstract

A redox-sensitive micellar system constructed from an O,N-hydroxyethyl chitosan-octylamine (HECS-ss-OA) conjugate with disulfide linkages between the hydrophobic alkyl chains and hydrophilic chitosan backbone was synthesized for triggered intracellular delivery of hydrophobic paclitaxel (PTX). In aqueous environments, conjugates formed micelles with high PTX loading (>30%). Mechanistically, the sensitivity of HECS-ss-OA micelles to reducing environments was investigated using the parameters of in vitro release and particle size. Intracellular release of nile red fluorescence alongside cytotoxicity studies further confirmed the potency of redox-sensitive micelles for intracellular drug delivery compared with redox-insensitive micelles. Additionally, an in vivo study confirmed the efficacy of PTX-loaded micelles in tumor-bearing mice with superior antitumor efficacy and diminished systemic toxicity when compared with the redox-insensitive micelles and a PTX solution. These results demonstrate the potential of redox-sensitive HECS-ss-OA micelles for intracellular trafficking of lipophilic anticancer drugs.

Keywords: anticancer effects; paclitaxel; polymeric micelle; redox-sensitive; triggered intracellular delivery.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Animals
  • Antineoplastic Agents, Phytogenic / administration & dosage
  • Antineoplastic Agents, Phytogenic / chemistry
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Chitosan / chemistry*
  • Drug Carriers / chemistry
  • Drug Delivery Systems / methods
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Mice
  • Mice, Inbred BALB C
  • Mice, Nude
  • Micelles
  • Oxidation-Reduction
  • Paclitaxel / administration & dosage*
  • Paclitaxel / chemistry*
  • Particle Size
  • Polymers / chemistry

Substances

  • Amines
  • Antineoplastic Agents, Phytogenic
  • Drug Carriers
  • Micelles
  • Polymers
  • Chitosan
  • Paclitaxel
  • octylamine