Synthesis and antimalarial activity of amide and ester conjugates of siderophores and ozonides

Biometals. 2023 Apr;36(2):315-320. doi: 10.1007/s10534-022-00375-8. Epub 2022 Mar 1.

Abstract

Despite advances in chemotherapeutic interventions for the treatment of malaria, there is a continuing need for the development of new antimalarial agents. Previous studies indicated that co-administration of chloroquine with antioxidants such as the iron chelator deferoxamine (DFO) prevented the development of persistent cognitive damage in surrogate models of cerebral malaria. The work described herein reports the syntheses and antimalarial activities of covalent conjugates of both natural (siderophores) and artificial iron chelators, namely DFO, ferricrocin and ICL-670, with antimalarial 1,2,4-trioxolanes (ozonides). All of the synthesized conjugates had potent antimalarial activities against the in vitro cultures of drug resistant and drug sensitive strains of Plasmodium falciparum. The work described herein provides the basis for future development of covalent combination of iron chelators and antimalarial chemotherapeutic agents for the treatment of cerebral malaria.

Keywords: Antimalarials; Cerebral malaria; Iron chelation; Siderophore-ozonide conjugates.

Publication types

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

MeSH terms

  • Amides
  • Antimalarials* / pharmacology
  • Antimalarials* / therapeutic use
  • Esters
  • Humans
  • Iron Chelating Agents / pharmacology
  • Iron Chelating Agents / therapeutic use
  • Malaria, Cerebral* / drug therapy
  • Siderophores / pharmacology

Substances

  • Antimalarials
  • Siderophores
  • 1,2,4-trioxane
  • Amides
  • Esters
  • Iron Chelating Agents