Boron-Pleuromutilins as Anti- Wolbachia Agents with Potential for Treatment of Onchocerciasis and Lymphatic Filariasis

J Med Chem. 2019 Mar 14;62(5):2521-2540. doi: 10.1021/acs.jmedchem.8b01854. Epub 2019 Feb 26.

Abstract

A series of pleuromutilins modified by introduction of a boron-containing heterocycle on C(14) of the polycyclic core are described. These analogs were found to be potent anti- Wolbachia antibiotics and, as such, may be useful in the treatment of filarial infections caused by Onchocerca volvulus, resulting in Onchocerciasis or river blindness, or Wuchereria bancrofti and Brugia malayi and related parasitic nematodes resulting in lymphatic filariasis. These two important neglected tropical diseases disproportionately impact patients in the developing world. The lead preclinical candidate compound containing 7-fluoro-6-oxybenzoxaborole (15, AN11251) was shown to have good in vitro anti- Wolbachia activity and physicochemical and pharmacokinetic properties providing high exposure in plasma. The lead was effective in reducing the Wolbachia load in filarial worms following oral administration to mice.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Boron / chemistry
  • Boron / pharmacology*
  • Diterpenes / chemistry
  • Diterpenes / pharmacology*
  • Elephantiasis, Filarial / drug therapy*
  • Filaricides / pharmacokinetics
  • Filaricides / pharmacology
  • Filaricides / therapeutic use*
  • Mice
  • Mice, Inbred BALB C
  • Mice, SCID
  • Onchocerciasis / drug therapy*
  • Pleuromutilins
  • Polycyclic Compounds / chemistry
  • Polycyclic Compounds / pharmacology*
  • Wolbachia / drug effects*
  • Wuchereria bancrofti / drug effects*

Substances

  • Diterpenes
  • Filaricides
  • Polycyclic Compounds
  • Boron