In Vitro and In Vivo Activities of Sulfur-Containing Linear Bisphosphonates against Apicomplexan Parasites

Antimicrob Agents Chemother. 2017 Jan 24;61(2):e01590-16. doi: 10.1128/AAC.01590-16. Print 2017 Feb.

Abstract

We tested a series of sulfur-containing linear bisphosphonates against Toxoplasma gondii, the etiologic agent of toxoplasmosis. The most potent compound (compound 22; 1-[(n-decylsulfonyl)ethyl]-1,1-bisphosphonic acid) is a sulfone-containing compound, which had a 50% effective concentration (EC50) of 0.11 ± 0.02 μM against intracellular tachyzoites. The compound showed low toxicity when tested in tissue culture with a selectivity index of >2,000. Compound 22 also showed high activity in vivo in a toxoplasmosis mouse model. The compound inhibited the Toxoplasma farnesyl diphosphate synthase (TgFPPS), but the concentration needed to inhibit 50% of the enzymatic activity (IC50) was higher than the concentration that inhibited 50% of growth. We tested compound 22 against two other apicomplexan parasites, Plasmodium falciparum (EC50 of 0.6 ± 0.01 μM), the agent of malaria, and Cryptosporidium parvum (EC50 of ∼65 μM), the agent of cryptosporidiosis. Our results suggest that compound 22 is an excellent novel compound that could lead to the development of potent agents against apicomplexan parasites.

Keywords: Cryptosporidium parvum; Plasmodium falciparum; Toxoplasma gondii; bisphosphonates; farnesyl diphosphate synthase; isoprenoids.

Publication types

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

MeSH terms

  • Animals
  • Antiprotozoal Agents / chemical synthesis
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / pharmacology*
  • Chemistry Techniques, Synthetic
  • Cryptosporidium parvum / drug effects*
  • Cryptosporidium parvum / growth & development
  • Diphosphonates / chemical synthesis
  • Diphosphonates / chemistry
  • Diphosphonates / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical / methods
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Geranyltranstransferase / antagonists & inhibitors
  • Humans
  • Mice, Inbred Strains
  • Plasmodium falciparum / drug effects*
  • Plasmodium falciparum / growth & development
  • Sulfur / chemistry
  • Sulfur / pharmacology
  • Toxoplasma / drug effects*
  • Toxoplasma / enzymology
  • Toxoplasma / growth & development
  • Toxoplasmosis / drug therapy

Substances

  • Antiprotozoal Agents
  • Diphosphonates
  • Enzyme Inhibitors
  • Sulfur
  • Geranyltranstransferase