Novel titanocene anti-cancer drugs derived from fulvenes and titanium dichloride

Tacke, Matthias; Allen, Lorcan T.; Cuffe, Laurence P.; Gallagher, William M.; Lou, Ying; Mendoza, Óscar; Müller‐Bunz, Helge; Rehmann, Franz-Josef K.; Sweeney, Nigel J.

doi:10.1016/j.jorganchem.2004.04.015

Cited by 89 publications

(39 citation statements)

References 22 publications

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“…In addition, alternative DNA damage-signalling pathways need to be evoked to circumvent the development of drug resistance. This observation has led to the synthesis of novel [(1,2-diaryl-1,2-dicyclopentadienyl)ethanediyl] titanium dichlorides (Tacke et al, 2004), which combine the reactivity of the titanium dichloride moiety with the ability of hydrogen bonding towards DNA of the amine ligand of cisplatin, if the aryl group is substituted accordingly. We have shown that one member from this series, Titanocene X is significantly more effective than titanium dichloride and exhibits potent cytotoxic effect on kidney carcinoma cells and is cytotoxic to cisplatin-resistant human ovarian carcinoma (Kelter et al, 2005).…”

Section: Discussionmentioning

confidence: 99%

“…Ansa-Titanocenes are a novel series of drugs synthesised from titanium dichloride and fulvenes (Teuber et al, 1997;Hartl et al, 2001;Tacke et al, 2001b;Siddik, 2003) that contain highly substituted ethylene bridge (Tacke et al, 2001a(Tacke et al, , 2004Rehmann et al, 2005). The subsequent synthesis of unbridged titanocene analogues led to increased cytotoxicity, suggesting a promising structure -function activity of these compounds .…”

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confidence: 99%

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Substituted titanocenes induce caspase-dependent apoptosis in human epidermoid carcinoma cells in vitro and exhibit antitumour activity in vivo

et al. 2007

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Titanocene compounds are a novel series of agents that exhibit cytotoxic effects in a variety of human cancer cells in vitro and in vivo. In this study, the antiproliferative activity of two titanocenes (Titanocenes X and Y) was evaluated in human epidermoid cancer cells in vitro. Titanocenes X and Y induce apoptotic cell death in epidermoid cancer cells, with IC50 values that are comparable to cisplatin. Characterisation of the cell death pathway induced by titanocene compounds in A431 cells revealed that apoptosis is preceded by cell cycle arrest and the inhibition of cell proliferation. The induction of apoptosis is dependent on the activation of caspase-3 and -7 but not caspase-8. Furthermore, the antitumour activity of Titanocene Y was tested in an A431 xenograft model of epidermoid cancer. Results indicate that Titanocene Y significantly reduced the growth of A431 xenografts with an antitumour effect similar to cisplatin. These results suggest that titanocenes represent a novel series of promising antitumour agents.

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

Substituted titanocenes induce caspase-dependent apoptosis in human epidermoid carcinoma cells in vitro and exhibit antitumour activity in vivo

et al. 2007

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“…The bent metallocene dichlorides can be modified either by substitution of the chloride ligands [5,6] or by substitution on the cyclopentadienyl rings [7,8]. Some of the recently prepared titanocene dichloride derivatives showed significantly better activity and stability than corresponding non-substituded counterparts [9][10][11][12]. These findings prompted us to study water-soluble vanadocene compounds [13][14][15].…”

Section: M]mentioning

confidence: 99%

Synthesis, characterization and structure of the Bis(methyl-cyclopentadienyl)vanadium(IV) carboxylates

et al. 2005

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Abstract:The 1,1'-dimethylvanadocene dichloride ((C 5 H 4 CH 3 ) 2 VCl 2 ) reacts in aqueous solution with various carboxylic acids giving two different types of complexes. The 1,1'-dimethylvanadocene complexes of monocarboxylic acids (C 5 H 4 CH 3 ) 2 V(OOCR) 2 (R = H, CCl 3 , CF 3 , C 6 H 5 ) contain two monodentate carboxylic ligands, whereas oxalic and malonic acids act as chelate compounds of the formula (C 5 H 4 CH 3 ) 2 V(OOC-A-COO) (A= -, CH 2 ). The structure of the (C 5 H 4 CH 3 ) 2 V(OOCCF 3 ) 2 complex was determined by single crystal X-ray diffraction analysis. The isotropic and anisotropic EPR spectra of all the complexes prepared were recorded. The obtained EPR parameter values were found to be in agreement with proposed structures.

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“…It should also be noted that the Ti(IV) products resulting from the hydrolysis process show a strong proliferative effect in hormone-dependent breast cancers [60]. The research continues, however, using titanium complexes of particularly robust ligands [61,62]. A concurrent approach, with the aim of lowering the toxicity of these metallic drugs, is based on changing the central metal.…”

Section: 25mentioning

confidence: 99%

A Novel Field of Research: Bioorganometallic Chemistry, Origins, and Founding Principles

2005

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Novel titanocene anti-cancer drugs derived from fulvenes and titanium dichloride

Cited by 89 publications

References 22 publications

Substituted titanocenes induce caspase-dependent apoptosis in human epidermoid carcinoma cells in vitro and exhibit antitumour activity in vivo

Substituted titanocenes induce caspase-dependent apoptosis in human epidermoid carcinoma cells in vitro and exhibit antitumour activity in vivo

Synthesis, characterization and structure of the Bis(methyl-cyclopentadienyl)vanadium(IV) carboxylates

A Novel Field of Research: Bioorganometallic Chemistry, Origins, and Founding Principles

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