Fluoromethylcyclopropylamine derivatives as potential in vivo toxicophores - A cautionary disclosure

Bioorg Med Chem Lett. 2019 Feb 15;29(4):560-562. doi: 10.1016/j.bmcl.2018.12.066. Epub 2019 Jan 2.

Abstract

Fluorination of metabolic hotspots in a molecule is a common medicinal chemistry strategy to improve in vivo half-life and exposure and, generally, this strategy offers significant benefits. Here, we report the application of this strategy to a series of poly-ADP ribose glycohydrolase (PARG) inhibitors, resulting in unexpected in vivo toxicity which was attributed to this single-atom modification.

Keywords: Animal welfare; Ataxia; Toxicophore.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Animals
  • Cyclopropanes / administration & dosage
  • Cyclopropanes / chemistry
  • Cyclopropanes / pharmacokinetics
  • Cyclopropanes / pharmacology*
  • Glycoside Hydrolases / administration & dosage
  • Glycoside Hydrolases / chemistry
  • Glycoside Hydrolases / pharmacokinetics
  • Glycoside Hydrolases / toxicity*
  • Half-Life
  • Humans
  • Mice
  • Microsomes, Liver / drug effects*
  • Microsomes, Liver / metabolism

Substances

  • Cyclopropanes
  • Glycoside Hydrolases
  • poly ADP-ribose glycohydrolase