Synthesis and activity of inhibitors highly specific for the glycolytic enzymes from Trypanosoma brucei

Mol Biochem Parasitol. 1993 Jun;59(2):201-10. doi: 10.1016/0166-6851(93)90218-m.

Abstract

Most glycosomal enzymes of Trypanosoma brucei carry a relatively high number of positive charges. In at least 3 of the enzymes some of the charges unique to these enzymes are concentrated in 2 distinct areas on the enzymes' surface, about 4 nm apart [4] and these positively charged structural elements have been suggested to be the site of interaction with the trypanocidal drug Suramin. We have synthesized a series of symmetrical long chain molecules with negative charges or strong dipoles at each end. Several of these compounds inhibited the glycosomal enzymes more strongly than Suramin. They also exhibited a specificity for the trypanosome enzymes, when compared with homologous enzymes from other organisms. By varying the chain length of the active compounds, a 4-nm distance between the molecules' extremes proved optimal for inhibition. Tetra-substituted compounds were better than di-substituted. Modifications introduced at the two ends indicated that a planar orientation, with an amide bond linking a phenyl ring to the chain, is preferred. Inhibition kinetics for some of the enzymes indicated the existence of multi-site interactions with the inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzoates / chemical synthesis
  • Benzoates / pharmacology*
  • Dicarboxylic Acids / chemical synthesis
  • Dicarboxylic Acids / pharmacology*
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology*
  • Glycolysis / drug effects*
  • Humans
  • Kinetics
  • Molecular Structure
  • Suramin / pharmacology
  • Trypanocidal Agents / chemical synthesis
  • Trypanocidal Agents / pharmacology*
  • Trypanosoma brucei brucei / drug effects
  • Trypanosoma brucei brucei / enzymology*

Substances

  • Benzoates
  • Dicarboxylic Acids
  • Enzyme Inhibitors
  • Trypanocidal Agents
  • Suramin