Synthesis and heme-binding correlation with antimalarial activity of 3,6-bis-(ω-N,N-diethylaminoamyloxy)-4,5-difluoroxanthone

Rozalia A. Dodean, Jane X. Kelly, David Peyton, Gary L. Gard, Michael K. Riscoe, Rolf W. Winter

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

In this study, the effect of fluorine upon the heme-binding ability of the xanthone nucleus was investigated for 3,6-bis-(ω-N,N-diethylaminoamyloxy)-4,5-difluoroxanthone (F2C5). 2-Fluoro-1,3-dimethoxybenzene was prepared by a new, improved method and used to build up the xanthone nucleus. The interaction of F2C5 with heme was investigated by UV-vis, 1H NMR, and 19F NMR spectroscopy. For the first time, NMR studies for the heme-drug interactions are carried out at pH 5.0, physiological for the acidic food vacuole of the malaria parasite.

Original languageEnglish (US)
Pages (from-to)1174-1183
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number3
DOIs
StatePublished - Feb 1 2008

Keywords

  • Fluoroxanthone
  • Heme-binding
  • Malaria
  • Spectroscopic investigation of binding

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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