Inhibition of Trypanosoma cruzi alpha-hydroxyacid dehydrogenase-isozyme II by N-isopropyl oxamate and its effect on intact epimastigotes

J Enzyme Inhib Med Chem. 2003 Jun;18(3):265-71. doi: 10.1080/1475636031000071826.

Abstract

The effect of N-isopropyl oxamate on the activity of alpha-hydroxyacid dehydrogenase-isozyme II (HADH-isozyme II) from Trypanosoma cruzi was investigated. The kinetic studies showed that this substance was a competitive inhibitor of this isozyme. The attachment of the nonpolar isopropylic branched chain to the nitrogen of oxamate increased 12-fold the affinity of N-isopropyl oxamate for the active site of T. cruzi HADH-isozyme II. N-isopropyl oxamate was a selective inhibitor of HADH-isozyme II, since other T. cruzi dehydrogenases were not inhibited by this substance. Since HADH-isozyme II participates in the energy metabolism of T. cruzi, a trypanocidal effect can be expected with inhibitors of this isozyme. However, although it was not possible to detect any trypanocidal activity with N-isopropyl oxamate when the ethyl ester was tested as a possible trypanocidal prodrug, the expected trypanocidal effect was obtained, comparable to that obtained with nifurtimox and benznidazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohol Oxidoreductases / antagonists & inhibitors*
  • Alcohol Oxidoreductases / chemistry*
  • Animals
  • Dose-Response Relationship, Drug
  • Kinetics
  • Models, Chemical
  • Nifurtimox / pharmacology
  • Nitroimidazoles / pharmacology
  • Oxamic Acid / analogs & derivatives*
  • Oxamic Acid / pharmacology*
  • Prodrugs
  • Protein Isoforms
  • Time Factors
  • Trypanocidal Agents / pharmacology
  • Trypanosoma cruzi / enzymology*

Substances

  • N-isopropyloxamate
  • Nitroimidazoles
  • Prodrugs
  • Protein Isoforms
  • Trypanocidal Agents
  • Alcohol Oxidoreductases
  • D-2-hydroxyacid dehydrogenase
  • Nifurtimox
  • Oxamic Acid
  • benzonidazole