Antiparasitic lethality of sulfonamidebenzamides in kinetoplastids

Bioorg Med Chem Lett. 2017 Feb 15;27(4):755-758. doi: 10.1016/j.bmcl.2017.01.043. Epub 2017 Jan 16.

Abstract

A sulfonamidebenzamide series was assessed for anti-kinetoplastid parasite activity based on structural similarity to the antiparasitic drug, nifurtimox. Through structure-activity optimization, derivatives with limited mammalian cell toxicity and increased potency toward African trypanosomes and Leishmania promastigotes were developed. Compound 22 had the best potency against the trypanosome (EC50=0.010μM) while several compounds showed ∼10-fold less potency against Leishmania promastigotes without impacting mammalian cells (EC50>25μM). While the chemotype originated from an unrelated optimization program aimed at selectively activating an apoptotic pathway in mammalian cancer cells, our preliminary results suggest that a distinct mechanism of action from that observed in mammalian cells is responsible for the promising activity observed in parasites.

Keywords: African sleeping sickness; Antiparasitic; Leishmaniasis; Sulfonamide.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiparasitic Agents / chemistry*
  • Antiparasitic Agents / pharmacology
  • Antiparasitic Agents / toxicity
  • Benzamides / chemistry*
  • Benzamides / pharmacology
  • Benzamides / toxicity
  • Cell Line
  • Cell Survival / drug effects
  • Humans
  • Leishmania / drug effects
  • Structure-Activity Relationship
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology
  • Sulfonamides / toxicity
  • Trypanosoma brucei brucei / drug effects

Substances

  • Antiparasitic Agents
  • Benzamides
  • Sulfonamides