Facile Fabrication of Tumor Redox-Sensitive Nanoassemblies of Small-Molecule Oleate Prodrug as Potent Chemotherapeutic Nanomedicine

Small. 2016 Dec;12(46):6353-6362. doi: 10.1002/smll.201601597. Epub 2016 Sep 30.

Abstract

The conjugate of paclitaxel (PTX) and docosahexaenoic acid has entered into clinical trials. However, the most recent clinical outcomes fell short of expectations, due to the extremely slow drug release from the hydrophobic conjugates. Herein, a novel prodrug-based nanoplatform self-assembled by the disulfide bond linked conjugates of PTX and oleic acid for rapid and differential release of PTX in tumor cells is reported. This redox-responsive prodrug-nanosystem demonstrates multiple therapeutic advantages, including one-step facile fabrication, high drug-loading efficiency (56%, w/w), on-demand drug release responding to redox stimuli, as well as favorable cellular uptake and biodistribution. These advantages result in significantly enhanced antitumor efficacy in vivo, with the tumor almost completely disappearing in mice. Such a uniquely engineered prodrug-nanosystem has great potential to be used as potent chemotherapeutic nanomedicine in clinical cancer therapy.

Keywords: cancer therapy; disulfide bonds; oleate prodrugs; paclitaxel; prodrug-nanosystems.

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / administration & dosage
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / therapeutic use
  • Cell Line, Tumor
  • Drug Carriers / chemistry
  • Drug Delivery Systems
  • Female
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Mice, Nude
  • Nanomedicine / methods*
  • Oleic Acid / chemistry*
  • Oxidation-Reduction
  • Paclitaxel / administration & dosage
  • Paclitaxel / chemistry
  • Paclitaxel / therapeutic use
  • Prodrugs / administration & dosage
  • Prodrugs / chemistry*
  • Prodrugs / therapeutic use
  • Rats
  • Rats, Sprague-Dawley
  • Uterine Cervical Neoplasms / drug therapy

Substances

  • Antineoplastic Agents, Phytogenic
  • Drug Carriers
  • Prodrugs
  • Oleic Acid
  • Paclitaxel