Synthesis, structure and cytotoxicity of triphenylphosphinegold(I) sulfanylpropenoates

J Inorg Biochem. 2008 Feb;102(2):184-92. doi: 10.1016/j.jinorgbio.2007.07.034. Epub 2007 Aug 7.

Abstract

The reaction of triphenylphosphinegold(I) chloride in ethanol in a 1:1 molar ratio with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x: p=3-phenyl-, Clp=3-(2-chlorophenyl)-, -o-mp=3-(2-methoxyphenyl)-, -p-mp=3-(4-methoxyphenyl)-, -o-hp=3-(2-hydroxyphenyl)-, -p-hp=3-(4-hydroxyphenyl)-, diBr-o-hp=3-(3,5-dibromo-2-hydroxyphenyl)-, f=3-(2-furyl)-, t=3-(2-thienyl)-, -o-py=3-(2-pyridyl)-; spa=2-sulfanylpropenoato] gave compounds of the type [Au(PPh(3))(Hxspa)], which were isolated and characterized as solids by elemental analysis, IR spectroscopy and FAB mass spectrometry and in solution by (1)H, (13)C and (31)P NMR spectroscopy. The structures of the complexes [Au(PPh(3))(HClpspa)], [Au(PPh(3))(H-o-mpspa)] and [Au(PPh(3))(H-p-mpspa)].2/3C(3)H(6)O were determined by X-ray diffractometry. Hydrogen bonding was found along with Au-S and Au-P bonds in all cases and weak pi-pi stacking was found in the H-p-mpspa derivative. The in vitro antitumour activities against the HeLa-229, A2780 and A2780cis cell lines were determined for all complexes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemical synthesis
  • Acrylates / chemistry
  • Acrylates / pharmacology
  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • HeLa Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Organogold Compounds / chemical synthesis*
  • Organogold Compounds / chemistry
  • Organogold Compounds / pharmacology
  • Phosphines / chemical synthesis
  • Phosphines / chemistry
  • Phosphines / pharmacology

Substances

  • Acrylates
  • Antineoplastic Agents
  • Organogold Compounds
  • Phosphines
  • triphenylphosphine gold chloride