Peroxides for chemotherapy of malaria and cancer

MEDI 4

Gary H. Posner, ghp@jhu.edu, Department of Chemistry, The Johns Hopkins University, 3400 N. Charles Street, Baltimore, MD 21218
Widespread resistance has greatly diminished the utility of previously reliable antimalarial drugs. Artemisinins and related trioxanes are among the newest antimalarials, and combination therapy that includes a trioxane with at least one other drug is now usually recommended in malaria-endemic areas. Although potent and fast-acting, the clinically available monomeric trioxanes commonly fail to achieve a cure when administered alone. In an effort to improve antimalarial activity and to prevent metabolic inactivation, a series of dimeric compounds that contain two artemisinin moieties linked by a short non-hydrolyzable bridge was designed and synthesized. In contrast to the clinically used trioxane artesunate which prolongs mouse survival by 3 days or less, for several of our new trioxane dimers a single subcutaneous dose of 30 mg/kg cured P. berghei-infected mice. Other of our dimers cured after three consecutive daily oral doses of 30 mg/kg. No toxicity was noted. The result is structurally diverse new trioxane dimers, obtained in good yield in a straightforward and inexpensive few steps from plant-derived artemisinin, having potent antimalarial activity, efficacy and safety in curing malaria-infected mice. These trioxane dimers are promising candidates for further preclinical and human studies toward much-needed new drug development for antimalarial chemotherapy.