Hydroxamic acid derivatives: a promising scaffold for rational compound optimization in Chagas disease

J Enzyme Inhib Med Chem. 2016 Dec;31(6):964-73. doi: 10.3109/14756366.2015.1077330. Epub 2015 Aug 31.

Abstract

This work describes the antitrypanocidal activity of two hydroxamic acid derivatives containing o-ethoxy (HAD1) and p-ethoxy (HAD2) as substituent in the aromatic ring linked to the isoxazoline ring. HAD1 and HAD2 induced a significant reduction in the number of intracellular parasites and consequently showed activity on the multiplication of the parasite. Treatment of cardiomyocytes and macrophages with the compounds revealed no significant loss in cell viability. Ultrastructural alterations after treatment of cardiomyocytes or macrophages infected by Trypanosoma cruzi with the IC50 value of HAD1 revealed alterations to amastigotes, showing initial damage seen as swelling of the kinetoplast. This gave a good indication of the ability of the drug to permeate through the host cell membrane as well as its selectivity to the parasite target. Both compounds HAD1 and 2 were able to reduce the cysteine peptidases and decrease the activity of metallopeptidases.

Keywords: Chagas disease; Trypanosoma cruzi; hydroxamic acid derivatives.

MeSH terms

  • Animals
  • Cells, Cultured
  • Chagas Disease / drug therapy*
  • Chagas Disease / microbiology
  • Dose-Response Relationship, Drug
  • Hydroxamic Acids / chemical synthesis
  • Hydroxamic Acids / chemistry*
  • Hydroxamic Acids / pharmacology*
  • Macrophages / drug effects
  • Macrophages / microbiology
  • Mice
  • Molecular Structure
  • Myocytes, Cardiac / drug effects
  • Myocytes, Cardiac / microbiology
  • Structure-Activity Relationship
  • Trypanocidal Agents / chemical synthesis
  • Trypanocidal Agents / chemistry*
  • Trypanocidal Agents / pharmacology*
  • Trypanosoma cruzi / drug effects*

Substances

  • Hydroxamic Acids
  • Trypanocidal Agents