Pseudo-halide derivatives of titanocene: synthesis and cytotoxicity studies

Metallomics. 2009 Nov;1(6):511-7. doi: 10.1039/b911753a. Epub 2009 Sep 2.

Abstract

The well-known anticancer drug candidate bis-[(p-methoxybenzyl)cyclopentadienyl] titanium(IV) dichloride (Titanocene ) was reacted with sodium azide or potassium cyanate, thiocyanate or selenocyanate in order to give pseudo-halide analogues of Titanocene . and were characterised by single crystal X-ray diffraction, which confirmed the expected nitrogen binding of the cyanate and thiocyanate to the titanium centre. All four titanocenes had their cytotoxicity investigated through preliminary in vitro testing on the LLC-PK (pig kidney epithelial) cell line in an MTT based assay in order to determine their IC50 values. Titanocenes were found to have IC50 values of 24 (± 8) μM, 101 (± 14) μM, 54 (± 21) μM and 27 (± 4) μM respectively. All four titanocene derivatives show significant cytotoxicity improvement when compared to unsubstituted titanocene dichloride and and showed similiar cytotoxic behaviour to Titanocene in vitro.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Cell Survival / drug effects*
  • Cyanates / chemistry
  • Inhibitory Concentration 50
  • Models, Molecular
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / toxicity*
  • Selenium Compounds / chemistry
  • Sodium Azide / chemistry
  • Swine
  • Thiocyanates / chemistry
  • Titanium / chemistry
  • X-Ray Diffraction

Substances

  • Cyanates
  • Organometallic Compounds
  • Selenium Compounds
  • Thiocyanates
  • titanocene
  • selenocyanic acid
  • Sodium Azide
  • Titanium
  • potassium cyanate
  • potassium thiocyanate