Dithiaarsanes induce oxidative stress-mediated apoptosis in HL-60 cells by selectively targeting thioredoxin reductase

J Med Chem. 2014 Jun 26;57(12):5203-11. doi: 10.1021/jm500221p. Epub 2014 Jun 11.

Abstract

The selenoprotein thioredoxin reductase (TrxR) plays a pivotal role in regulating cellular redox homeostasis and has attracted increasing attention as a promising anticancer drug target. We report here that 2-(4-aminophenyl)-1,3,2-dithiarsinane (PAO-PDT, 4), a potent and highly selective small molecule inhibitor of TrxR, stoichiometrically binds to the C-terminal selenocysteine/cysteine pair in the enzyme in vitro and induces oxidative stress-mediated apoptosis in HL-60 cells. The molecular action of 4 in cells involves inhibition of TrxR, elevation of reactive oxygen species, depletion of cellular thiols, and activation of caspase-3. Knockdown of TrxR sensitizes the cells to 4 treatment, whereas overexpression of the functional enzyme alleviates the cytotoxicity, providing physiological relevance for targeting TrxR by 4 in cells. The simplicity of the structure and the presence of an easily manipulated amine group will facilitate the further development of 4 as a potential cancer chemotherapeutic agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Apoptosis*
  • Arsenicals / chemical synthesis*
  • Arsenicals / chemistry
  • Arsenicals / pharmacology
  • Drug Screening Assays, Antitumor
  • Gene Knockdown Techniques
  • HL-60 Cells
  • Humans
  • Oxidative Stress*
  • Reactive Oxygen Species / metabolism
  • Sulfhydryl Compounds / metabolism
  • Thioredoxin-Disulfide Reductase / antagonists & inhibitors*
  • Thioredoxin-Disulfide Reductase / genetics
  • Thioredoxin-Disulfide Reductase / metabolism

Substances

  • 2-(4-aminophenyl)-1,3,2-dithiarsinane
  • Antineoplastic Agents
  • Arsenicals
  • Reactive Oxygen Species
  • Sulfhydryl Compounds
  • Thioredoxin-Disulfide Reductase