Amodiaquine accumulation in Plasmodium falciparum as a possible explanation for its superior antimalarial activity over chloroquine

Mol Biochem Parasitol. 1996 Sep;80(1):15-25. doi: 10.1016/0166-6851(96)02655-2.

Abstract

Amodiaquine is a 4-aminoquinoline antimalarial whose structure is similar to chloroquine. In contrast to the wealth of information available about chloroquine accumulation and its relationship to activity, little is known about the uptake characteristics of amodiaquine, a drug that is inherently more active against malaria parasites. In this study we have investigated the accumulation of amodiaquine in Plasmodium falciparum in vitro, in order to gain an insight into the mechanisms responsible for its superior activity over chloroquine. The driving force for parasite accumulation of the 4-aminoquinolines is proposed to be a transmembrane proton gradient maintained by a vacuolar ATPase. In the present study, amodiaquine accumulation was greatly reduced, at steady state, in the absence of glucose and at 0 degrees C indicating a clear energy dependence of uptake. Amodiaquine accumulation in Plasmodium falciparum was shown to be 2- to 3-fold greater than chloroquine accumulation. This observation probably accounts for amodiaquine's greater inherent activity but is surprising given that amodiaquine is a weaker base than chloroquine. With this in mind we present evidence for an intraparasitic binding component in the accumulation of the 4-aminoquinolines. Differences in binding affinity of this 'receptor' for amodiaquine and chloroquine may partially explain the greater accumulation and in vitro potency of amodiaquine compared to chloroquine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / metabolism
  • Ammonium Chloride / pharmacology
  • Amodiaquine / metabolism*
  • Amodiaquine / pharmacology
  • Animals
  • Anti-Bacterial Agents / pharmacology
  • Antimalarials / metabolism*
  • Antimalarials / pharmacology
  • Biological Transport, Active
  • Chloroquine / metabolism
  • Chloroquine / pharmacology
  • Enzyme Inhibitors / pharmacology
  • Glucose / metabolism
  • Hydrogen-Ion Concentration
  • Ionophores / pharmacology
  • Kinetics
  • Macrolides*
  • Nigericin / pharmacology
  • Plasmodium falciparum / drug effects
  • Plasmodium falciparum / metabolism*
  • Proton-Translocating ATPases / antagonists & inhibitors
  • Protons

Substances

  • Anti-Bacterial Agents
  • Antimalarials
  • Enzyme Inhibitors
  • Ionophores
  • Macrolides
  • Protons
  • Ammonium Chloride
  • Amodiaquine
  • Chloroquine
  • bafilomycin A1
  • Adenosine Triphosphate
  • Proton-Translocating ATPases
  • Glucose
  • Nigericin