A new strategy against malaria – antimalarial ionic liquids derived from aminoquinolines and fatty acids

Silva, Ana Teresa; Teixeira, Cátia; Fontinha, Diana; Prudêncio, Cristina; Prudêncio, Miguel; Gomes, Paula; Ferraz, Ricardo

http://hdl.handle.net/10400.22/20461

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Abstract(s)

Based on the recent promising results obtained by us, where ionic liquids (ILs) derived from primaquine were found as triple-stage antimalarial hits, we have now produced, by simple, quantitative, and low-cost methods, new ILs via simple acid-base titration of antimalarial aminoquinolines (primaquine and chloroquine) with natural fatty acids (Figure 1). We have also synthesized, in good to high yields, the covalent amide analogues of these ILs (Figure 1), in order to establish how the nature of the chemical bond (ionic ammonium carboxylate versus covalent amide) between both building blocks influences the physico-chemical and biological properties of the final compounds. Results obtained thus far allow us to conclude that both ionic and covalent compounds (i) have higher thermostability than the parent drugs, and (ii) display remarkable in vitro activity against liver-stage malaria parasites.