Xanthatin Promotes Apoptosis via Inhibiting Thioredoxin Reductase and Eliciting Oxidative Stress

Mol Pharm. 2018 Aug 6;15(8):3285-3296. doi: 10.1021/acs.molpharmaceut.8b00338. Epub 2018 Jul 5.

Abstract

Xanthatin (XT), a naturally occurring sesquiterpene lactone presented in cocklebur ( Xanthium strumarium L.), is under development as a potential anticancer agent. Despite the promising anticancer effect of XT, the molecular mechanism underlying its cellular action has not been well elucidated. The mammalian thioredoxin reductase (TrxR) enzymes, the essential seleno-flavoproteins containing a penultimate selenocysteine (Sec) residue at the C-terminus, represent a promising target for cancer chemotherapeutic agents. In this study, XT inhibits both the purified TrxR and the enzyme in cells. The possible binding mode of XT with the TrxR protein is predicted by the covalent docking method. Mechanism studies reveal that XT targets the Sec residue of TrxR and inhibits the enzyme activity irreversibly. Simultaneously, the inhibition of TrxR by XT promotes the oxidative stress-mediated apoptosis of HeLa cells. Importantly, the knockdown of the enzyme sensitizes the cells to XT treatment. Targeting TrxR thus discloses a novel molecular mechanism in accounting for the cellular action of XT and provides insights into the development of XT as an anticancer agent.

Keywords: anticancer; apoptosis; molecular docking; oxidative stress; thioredoxin; xanthatin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apoptosis / drug effects
  • Drug Screening Assays, Antitumor
  • Furans / chemistry
  • Furans / pharmacology*
  • HeLa Cells
  • Humans
  • Molecular Docking Simulation
  • Oxidative Stress / drug effects
  • Reactive Oxygen Species / metabolism
  • Thioredoxin-Disulfide Reductase / antagonists & inhibitors*
  • Thioredoxin-Disulfide Reductase / chemistry
  • Thioredoxin-Disulfide Reductase / metabolism
  • Xanthium / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Furans
  • Reactive Oxygen Species
  • xanthatin
  • Thioredoxin-Disulfide Reductase