In vitro metabolic profile and in vivo antischistosomal activity studies of (η(6)-praziquantel)Cr(CO)3 derivatives

J Med Chem. 2013 Nov 27;56(22):9192-8. doi: 10.1021/jm401287m. Epub 2013 Nov 12.

Abstract

In vitro metabolic behavior was investigated for two chromium tricarbonyl derivatives of the antischistosomal drug praziquantel (PZQ) with the formula (η(6)-PZQ)Cr(CO)3 (1 and 2), by use of human liver microsomes. The metabolic profiles of the derivatives differ significantly. The optically pure (η(6)-PZQ)Cr(CO)3 derivatives (S, Sp)-1, (R, Rp)-1, (S, Rp)-2, and (R, Sp)-2 were also prepared to assess the eudysmic ratios of 1 and 2 against Schistosoma mansoni in vitro. A strong enantioselective antischistosomal activity was observed. The R-enantiomers are highly active against adult schistosomes in vitro (IC50 0.08-0.13 μM), whereas both S-enantiomers lack activity. The in vivo activity of 1 and 2 was then studied in mice harboring a chronic S. mansoni infection. A single dose of 1 and 2 (400 mg/kg) resulted in low worm burden reductions of 24% and 29% (p > 0.05).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthelmintics / chemistry
  • Anthelmintics / metabolism*
  • Anthelmintics / pharmacology*
  • Female
  • Humans
  • Mice
  • Optical Phenomena
  • Praziquantel / chemistry
  • Praziquantel / metabolism*
  • Praziquantel / pharmacology*
  • Schistosoma mansoni / drug effects*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Anthelmintics
  • Praziquantel