Reduced Toxicity of Liposomal Nitrogen Mustard Prodrug Formulation Activated by an Intracellular ROS Feedback Mechanism in Hematological Neoplasm Models

Mol Pharm. 2020 Feb 3;17(2):499-506. doi: 10.1021/acs.molpharmaceut.9b00928. Epub 2019 Dec 27.

Abstract

Nitrogen mustard (NM) is among the earliest drugs used to treat malignant tumors and it kills tumor cells by cross-linking DNA. Unfortunately, because of the short half-life and unfavorable selectivity, NM causes significant damage to normal tissues. As NM can increase the levels of reactive oxygen species (ROS) in tumor cells, a ROS-activated nitrogen mustard prodrug (NM-Pro) was synthesized and mixed with NM at a specific ratio to obtain an "NM-ROS-NM-Pro-NM" positive feedback system, which ultimately achieves a specific lethal effect on hematological neoplasms. The further encapsulation of NM/NM-Pro in liposomes allows the sustained release of the drug and prolongs the residence time in vivo. Here, we prepared stable liposomes with a uniform particle size of 170.6 ± 2.2 nm. The optimal ratio of NM to NM-Pro in this study was 2:1. The active drug NM in the NM/NM-Pro system continuously stimulated ROS production by the cells, which in turn further activated the NM-Pro to continuously generate NM. The positive feedback pathway between the NM and NM-Pro resulted in the specific death of tumor cells. Furthermore, the K562 hematological neoplasm model was utilized to evaluate the therapeutic effect of NM/NM-Pro liposomes in vivo. After encapsulation in liposomes, the targeting of tumor cells was increased approximately two times compared with that of normal cells, and NM/NM-Pro liposomes exhibited reduced toxicity, without an increase in drug activity compared to the NM/NM-Pro combination. The NM/NM-Pro delivery system exerts a positive feedback effect on ROS production in tumor cells and displays good potential for the specific killing of hematoma cells.

Keywords: neactive oxygen species; nematological neoplasms; nitrogen mustard; nitrogen mustard prodrugs; positive feedback.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Alkylating / administration & dosage*
  • Antineoplastic Agents, Alkylating / pharmacokinetics
  • Cell Survival / drug effects
  • Disease Models, Animal
  • Drug Compounding / methods*
  • Drug Delivery Systems / methods*
  • Drug Liberation
  • Feedback, Physiological*
  • Female
  • Hematologic Neoplasms / drug therapy*
  • Humans
  • K562 Cells
  • Liposomes
  • Mechlorethamine / administration & dosage*
  • Mechlorethamine / pharmacokinetics
  • Mice
  • Particle Size
  • Prodrugs / administration & dosage*
  • Prodrugs / pharmacokinetics
  • Rats
  • Rats, Sprague-Dawley
  • Reactive Oxygen Species / metabolism*
  • Treatment Outcome

Substances

  • Antineoplastic Agents, Alkylating
  • Liposomes
  • Prodrugs
  • Reactive Oxygen Species
  • Mechlorethamine