Tumor-Activated Benzothiazole Inhibitors of Stearoyl-CoA Desaturase

J Med Chem. 2020 Sep 10;63(17):9773-9786. doi: 10.1021/acs.jmedchem.0c00899. Epub 2020 Aug 19.

Abstract

A series of N-acyl benzothiazoles shows selective and potent cytotoxicity against cancer cell lines expressing cytochrome P450 4F11. A prodrug form is metabolized by cancer cells into an active inhibitor of stearoyl-CoA desaturase (SCD). Substantial variation on the acyl portion of the inhibitors allowed the identification of (R)-27, which balanced potency, solubility, and lipophilicity to allow proof-of-concept studies in mice. The prodrugs were activated inside the tumor, where they can arrest tumor growth. Together, these observations offer promise that a tumor-activated prodrug strategy might exploit the essentiality of SCD for tumor growth, while avoiding toxicity associated with systemic SCD inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzothiazoles / pharmacokinetics
  • Benzothiazoles / pharmacology*
  • Cell Line, Tumor
  • Cytochrome P450 Family 4 / metabolism
  • Enzyme Inhibitors / pharmacology*
  • Female
  • Humans
  • Mice
  • Prodrugs / metabolism
  • Stearoyl-CoA Desaturase / antagonists & inhibitors*
  • Tissue Distribution

Substances

  • Benzothiazoles
  • Enzyme Inhibitors
  • Prodrugs
  • Cytochrome P450 Family 4
  • CYP4F11 protein, human
  • Stearoyl-CoA Desaturase
  • benzothiazole