Synthesis of BODIPY-labeled alkylphosphocholines with leishmanicidal activity, as fluorescent analogues of miltefosine

Bioorg Med Chem Lett. 2008 Dec 15;18(24):6336-9. doi: 10.1016/j.bmcl.2008.10.089. Epub 2008 Nov 1.

Abstract

Two general synthetic methods are described, by which the highly fluorescent and photostable BODIPY group can be inserted in and aligned with the alkyl backbone of linear lipids. These methods have been used to prepare strongly emitting analogues of the leishmanicidal drug miltefosine, in which the antiparasite activity in vitro of the original drug is preserved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiprotozoal Agents / chemical synthesis*
  • Antiprotozoal Agents / pharmacology
  • Boron Compounds / chemical synthesis*
  • Boron Compounds / pharmacology
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / pharmacology
  • Humans
  • Leishmania donovani / metabolism*
  • Lipids / chemistry
  • Models, Chemical
  • Phosphorylcholine / analogs & derivatives*
  • Phosphorylcholine / chemistry*
  • Phosphorylcholine / pharmacology
  • Solvents / chemistry
  • Spectrophotometry / methods

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Antiprotozoal Agents
  • Boron Compounds
  • Fluorescent Dyes
  • Lipids
  • Solvents
  • Phosphorylcholine
  • miltefosine