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  • Pseudo-halide derivatives of titanocene: synthesis and cytotoxicity studies.

Pseudo-halide derivatives of titanocene: synthesis and cytotoxicity studies.

Metallomics : integrated biometal science (2009-11-01)
James Claffey, Anthony Deally, Brendan Gleeson, Megan Hogan, Luis Miguel Menéndez Méndez, Helge Müller-Bunz, Siddappa Patil, Denise Wallis, Matthias Tacke
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Potassium thiocyanate, BioXtra, ≥99.0%
Sigma-Aldrich
Potassium cyanate-15N, ≥98 atom % 15N, ≥95% (CP)
Sigma-Aldrich
Potassium thiocyanate, ACS reagent, 99%
Sigma-Aldrich
Potassium thiocyanate, ReagentPlus®, ≥99.0%
Sigma-Aldrich
Potassium selenocyanate, reagent grade, 97%
Sigma-Aldrich
Potassium selenocyanate, ReagentPlus®, ≥99%
Sigma-Aldrich
Potassium thiocyanate solution, volumetric, 8 M KSCN
Sigma-Aldrich
Potassium cyanate, 96%