Metallocene-based antimalarials: an exploration into the influence of the ferrocenyl moiety on in vitro antimalarial activity in chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum

Bioorg Med Chem. 2007 Oct 15;15(20):6510-6. doi: 10.1016/j.bmc.2007.07.012. Epub 2007 Aug 1.

Abstract

To establish the role of the ferrocenyl moiety in the antiplasmodial activity of ferroquine, compounds in which this moiety is replaced by the corresponding ruthenium-based moieties were synthesized and evaluated. In both the sensitive (D10) and resistant (K1) strains of Plasmodium falciparum, ruthenoquine analogues showed comparable potency to ferroquine. This suggests that a probable role of the ferrocenyl fragment is to serve simply as a hydrophobic spacer group. In addition, ferroquine analogues with different aromatic substituents were synthesized and evaluated. Unexpectedly high activity for quinoline compounds lacking the 7-chloro substituent suggests the ferrocenyl moiety may have an additive and/or synergistic effect.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry*
  • Antimalarials / pharmacology*
  • Chloroquine / chemistry
  • Chloroquine / pharmacology*
  • Drug Resistance / drug effects
  • Ferrous Compounds / chemistry*
  • Metallocenes
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / pharmacology*
  • Plasmodium falciparum / drug effects*
  • Sensitivity and Specificity
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Ferrous Compounds
  • Metallocenes
  • Organometallic Compounds
  • metallocene
  • Chloroquine
  • ferrocene