Salinipostins A-K, long-chain bicyclic phosphotriesters as a potent and selective antimalarial chemotype

J Org Chem. 2015 Feb 6;80(3):1312-20. doi: 10.1021/jo5024409. Epub 2015 Jan 13.

Abstract

Despite significant advances in antimalarial chemotherapy over the past 30 years, development of resistance to frontline drugs remains a significant challenge that limits efforts to eradicate the disease. We now report the discovery of a new class of antimalarials, salinipostins A-K, with low nanomolar potencies and high selectivity indices against mammalian cells (salinipostin A: Plasmodium falciparum EC50 50 nM, HEK293T cytotoxicity EC50 > 50 μM). These compounds were isolated from a marine-derived Salinospora sp. bacterium and contain a bicyclic phosphotriester core structure, which is a rare motif among natural products. This scaffold differs significantly from the structures of known antimalarial compounds and represents a new lead structure for the development of therapeutic targets in malaria. Examination of the growth stage specificity of salinipostin A indicates that it exhibits growth stage-specific effects that differ from compounds that inhibit heme polymerization, while resistance selection experiments were unable to identify parasite populations that exhibited significant resistance against this compound class.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemistry*
  • Antimalarials / pharmacology*
  • Biological Products / chemistry*
  • Biological Products / isolation & purification
  • Biological Products / pharmacology*
  • Bridged Bicyclo Compounds / chemistry*
  • Bridged Bicyclo Compounds / isolation & purification
  • Bridged Bicyclo Compounds / pharmacology*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / isolation & purification
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
  • HEK293 Cells / chemistry*
  • Humans
  • Malaria / metabolism*
  • Marine Biology
  • Plasmodium falciparum / chemistry
  • Plasmodium falciparum / drug effects*

Substances

  • Antimalarials
  • Biological Products
  • Bridged Bicyclo Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • salinipostin A