Targeted Delivery and Sustained Antitumor Activity of Triptolide through Glucose Conjugation

Angew Chem Int Ed Engl. 2016 Sep 19;55(39):12035-9. doi: 10.1002/anie.201606121. Epub 2016 Aug 30.

Abstract

Triptolide, a key ingredient from the traditional Chinese medicinal plant thunder god vine, which has been used to treat inflammation and autoimmune diseases for centuries, has been shown to be an irreversible inhibitor of the XPB subunit of the transcription factor TFIIH and initiation of RNA polymerase II mediated transcription. The clinical development of triptolide over the past two decades has been limited by its toxicity and low water solubility. Herein, we report the development of a glucose conjugate of triptolide, named glutriptolide, which was intended to target tumor cells overexpressing glucose transporters selectively. Glutriptolide did not inhibit XPB activity in vitro but demonstrated significantly higher cytotoxicity against tumor cells over normal cells with greater water solubility than triptolide. Furthermore, it exhibited remarkable tumor control in vivo, which is likely due to sustained stepwise release of active triptolide within cancer cells. These findings indicate that glutriptolide may serve as a promising lead for developing a new mechanistic class of anticancer drugs.

Keywords: antitumor agents; cytotoxicity; glucose transporters; prostate cancer; triptolide.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / administration & dosage*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / therapeutic use*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Diterpenes / administration & dosage*
  • Diterpenes / chemistry
  • Diterpenes / therapeutic use*
  • Drug Delivery Systems*
  • Epoxy Compounds / administration & dosage
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / therapeutic use
  • Glucose / chemistry*
  • HEK293 Cells
  • Humans
  • Mice
  • Neoplasms / drug therapy*
  • Phenanthrenes / administration & dosage*
  • Phenanthrenes / chemistry
  • Phenanthrenes / therapeutic use*

Substances

  • Antineoplastic Agents
  • Diterpenes
  • Epoxy Compounds
  • Phenanthrenes
  • triptolide
  • Glucose