Antimony(V) and bismuth(V) complexes of lapachol: synthesis, crystal structure and cytotoxic activity

Molecules. 2011 Dec 13;16(12):10314-23. doi: 10.3390/molecules161210314.

Abstract

Antimony(V) and bismuth(V) complexes of lapachol have been synthesized by the reaction of Ph₃SbCl₂ or Ph₃BiCl₂ with lapachol (Lp) and characterized by several physicochemical techniques such as IR, and NMR spectroscopy and X-ray crystallography. The compounds contain six-coordinated antimony and bismuth atoms. The antimony(V) complex is a monomeric derivative, (Lp)(Ph₃Sb)OH, and the bismuth(V) complex is a dinuclear compound bridged by an oxygen atom, (Lp)₂(Ph₃Bi)₂O. Both compounds inhibited the growth of a chronic myelogenous leukemia cell line and the complex of Bi(V) was about five times more active than free lapachol. This work provides a rare example of an organo-Bi(V) complex showing significant cytotoxic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimony / chemistry
  • Antimony / pharmacology*
  • Bismuth / chemistry
  • Bismuth / pharmacology*
  • Cell Death / drug effects
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Female
  • Humans
  • K562 Cells
  • Magnetic Resonance Spectroscopy
  • Middle Aged
  • Molecular Conformation
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / chemistry
  • Naphthoquinones / pharmacology*

Substances

  • Naphthoquinones
  • Antimony
  • lapachol
  • Bismuth