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Cytotoxic homoleptic Ti(IV) compounds of ONO-type ligands: synthesis, structures and anti-cancer activity

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Abstract

Eight Ti(IV) compounds 1–8, of the type [Ti(Ln)2] where Ln is a variously substituted dianionic tridentate acylhydrazone, were synthesized by reacting the appropriate hydrazide with 2-hydroxybenzaldehyde or 2′-hydroxyacetophenone and titanium(IV) tetra(isopropoxide) in a 2 : 2 : 1 molar ratio. The solid-state structures of 1–6 and 7·CH2Cl2 were deduced from the single crystal X-ray diffraction data, which indicated that each L2− ligand is fully deprotonated and coordinated to the Ti(IV) cation via the enolic oxygen, the imino nitrogen and the phenolic oxygen atoms (ONO donor set) in an enol tautomeric form, the metal assuming the distorted octahedral geometry. The structures of pro-ligands H2L3 and H2L5 are also reported. All complexes displayed high hydrolytic stability. In vitro cytotoxicity assays towards human ovarian A2780 and colon HT-29 cancer cell lines revealed the activity dependence on the acylhydrazone substituents, with electron-donating groups on the phenolato units enhancing the solubility and promoting cytotoxicity. The lead compound 5 of this study presents IC50 values of 2.5 ± 0.2 and 4.2 ± 0.6 μM for ovarian A2780 and colon HT-29 human cancer cells, respectively.

Graphical abstract: Cytotoxic homoleptic Ti(iv) compounds of ONO-type ligands: synthesis, structures and anti-cancer activity

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Publication details

The article was received on 16 Sep 2018, accepted on 20 Nov 2018 and first published on 21 Nov 2018


Article type: Paper
DOI: 10.1039/C8DT03747G
Citation: Dalton Trans., 2019, Advance Article
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    Cytotoxic homoleptic Ti(IV) compounds of ONO-type ligands: synthesis, structures and anti-cancer activity

    R. Manne, M. Miller, A. Duthie, M. F. C. Guedes da Silva, E. Y. Tshuva and T. S. Basu Baul, Dalton Trans., 2019, Advance Article , DOI: 10.1039/C8DT03747G

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