Synthesis of a Reactive Oxygen Species-Responsive Doxorubicin Derivative

Molecules. 2018 Jul 21;23(7):1809. doi: 10.3390/molecules23071809.

Abstract

A heterobifunctional reactive oxygen species (ROS)-responsive linker for directed drug assembly onto and delivery from a quantum dot (QD) nanoparticle carrier was synthesized and coupled to doxorubicin using N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC)/sulfo⁻NHS coupling. The doxorubicin conjugate was characterized using ¹H NMR and LC-MS and subsequently reacted under conditions of ROS formation (Cu2+/H₂O₂) resulting in successful and rapid thioacetal oxidative cleavage, which was monitored using ¹H NMR.

Keywords: doxorubicin; heterobifunctional; linker.

MeSH terms

  • Doxorubicin / analogs & derivatives
  • Doxorubicin / chemical synthesis*
  • Doxorubicin / chemistry
  • Doxorubicin / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nanoparticles / chemistry
  • Oxidation-Reduction / drug effects
  • Peptides / chemistry
  • Quantum Dots
  • Reactive Oxygen Species / metabolism*

Substances

  • Peptides
  • Reactive Oxygen Species
  • Doxorubicin