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Issue 46, 2014
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Synthesis, cytotoxic and hydrolytic studies of titanium complexes anchored by a tripodal diamine bis(phenolate) ligand

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Abstract

The reactivity, cytotoxic studies and hydrolytic behaviour of diamine bis(phenolate) titanium complexes are reported. The reactions of [Ti(tBu2O2NN′)Cl]2(μ-O) (1) with LiOiPr or HOiPr in the presence of NEt3, aiming at the synthesis of the alkoxido derivative of 1 led to no reaction or to the synthesis of the monomeric complex [Ti(tBu2O2NN′)(OiPr)2] (3), respectively. A small amount of the alkoxidotitanium dimer [Ti(tBu2O2NN′)(OiPr)]2(μ-O) (2) crystallized out of a solution of 3 and DFT calculations showed that the transformation of 1 into 3 is a thermodynamically favorable process in the presence of a base (NEt3) (ΔG = −14.7 kcal mol−1). 2 was quantitatively obtained through the direct reaction of the ligand precursor H2(tBu2O2NN′) with titanium tetra(isopropoxido). Further reaction of 2 with an excess of TMSCl was revealed to be the most suitable method for the preparation of [Ti(tBu2O2NN′)Cl2] (4). 1 and 3 disclosed cytotoxic activity towards HeLa, Fem-x, MDA-MB-361 and K562 cells and 1 exhibited moderate binding affinity to FS-DNA. 1H NMR hydrolysis studies attested the fast decomposition of 4 in the presence of D2O. The hydrolysis of 3 is slower and proceeds through the formation of [Ti(tBu2O2NN′)(OH)]2(μ-O) (5) that was crystallographically characterized. Upon D2O addition 1 immediately forms complex new species, stable in solution for long periods (weeks).

Graphical abstract: Synthesis, cytotoxic and hydrolytic studies of titanium complexes anchored by a tripodal diamine bis(phenolate) ligand

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The article was received on 02 Apr 2014, accepted on 19 Sep 2014 and first published on 26 Sep 2014


Article type: Paper
DOI: 10.1039/C4DT00975D
Citation: Dalton Trans., 2014,43, 17422-17433
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    Synthesis, cytotoxic and hydrolytic studies of titanium complexes anchored by a tripodal diamine bis(phenolate) ligand

    S. Barroso, A. M. Coelho, S. Gómez-Ruiz, M. J. Calhorda, Ž. Žižak, G. N. Kaluđerović and A. M. Martins, Dalton Trans., 2014, 43, 17422
    DOI: 10.1039/C4DT00975D

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