Binding and hydrolysis studies of antitumoural titanocene dichloride and Titanocene Y with phosphate diesters

Erxleben, Andrea; Claffey, James; Tacke, Matthias

doi:10.1016/j.jinorgbio.2009.11.010

Cited by 28 publications

(32 citation statements)

References 69 publications

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“…Upon dissolution in D 2 O (1,4-dioxane was used as internal reference [83]), monocyclopentadienyl compounds 1a·HCl-1c·HCl give acidic yellow solutions (2 mM, pD = 2.80-2.56, pD = pH* + 0.4, where pH* = pHmeter reading in D 2 O [84]), while compounds 2a–2c afford pD values of 4.74 ( 2a ), 5.95 ( 2b ) and 5.62 ( 2c ), respectively, at similar concentrations of ca. 2 mM.…”

Section: Resultsmentioning

confidence: 99%

“…The aqueous solution behaviour of [(η 5 -C 5 H 5 ) n TiCl 4-n ] (n = 1, 2) has been well documented [83–89]. Rapid hydrolysis of halide ligands occurs through a series of equilibrium reactions in which cyclopentadienyl rings (Cp) remain metal bound at pH < 3.0–3.5.…”

Section: Resultsmentioning

confidence: 99%

“…Rapid hydrolysis of halide ligands occurs through a series of equilibrium reactions in which cyclopentadienyl rings (Cp) remain metal bound at pH < 3.0–3.5. At higher pH, protonolysis of Cp initiates to give cyclopentadiene as well as insoluble, uncharacterized titanium hydrolysis products [83,84,87,89]. Accordingly, resonances due to cyclopentadiene (multiplets at δ 6.61, 6.55 and 2.98, see Supplementary data) were observed in the recorded 1 H NMR spectra of more acidic 1a·HCl-1c·HCl or 2a only after 24 h, while more basic solutions of 2b and 2c exhibit, within the first min after dilution, minor multiplets assigned to free cyclopentadiene.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Novel enantiopure cyclopentadienyl Ti(IV) oximato compounds as potential anticancer agents

Cueva-Alique

Muñoz-Moreno

Benabdelouahab

et al. 2016

Journal of Inorganic Biochemistry

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The synthesis and characterization of new enantiopure cyclopentadienyl titanium oximato compounds (S,R)-[(η5-C5H5)Ti{κ2NO,(R)NH·HCl}Cl2] (R = Ph (phenyl) 1a·HCl, Bn (benzyl) 1b·HCl, 2-pic (2-picolyl) 1c·HCl), (S,R)-[(η5-C5H5)TiCl2{κ2NO,(Ph)NH}] (1a) and (S,R)-[(η5-C5H5)2TiCl{κ2NO,(R)NH}] (R = Ph 2a, Bn 2b, 2-pic 2c), along with studies on their behaviour in D2O at different pD values are reported. The structure of previously described ammonium-oxime (2S,5R)-{NOH,(Bn)NH·HCl} (b·HCl) and novel titanium derivative 1a have been determined by single crystal X-ray crystallography. The effect of the compounds on cytotoxicity, cell adhesion and migration of the androgen-independent prostate cancer PC-3 cells has been assessed. Compounds 2b and 2c are more cytotoxic than additive doses of titanocene dichloride and free oxime proligand, probing the synergistic effect of these novel compounds. The cytotoxicity of 2b and 2c has been further evaluated against human renal Caki-1, colon DLD-1 and triple negative breast MDA-MB-231 cancer cell lines. The activity found for 2c on PC-3 and Caki-1 is higher than that of highly active Titanocene Y (bis-[(p-methoxybenzyl)cyclopentadienyl]titanium(IV) dichloride), while showing selectivity against renal cancer when compared to a non-tumorigenic human renal (HEK-293T) cell line. Compounds 2b and especially 2c are apoptotic in Caki-1 cancer cell lines. Cell adhesion and wound-healing assays confirmed that derivatives 1c·HCl, 2b and 2c affect the adhesion and migration patterns of the PC-3 cell line. Interactions of the novel compounds with plasmid (pBR322) DNA have also been studied, showing that the oximato Ti(IV) derivatives have a weak or no interaction with DNA at physiological pH.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Novel enantiopure cyclopentadienyl Ti(IV) oximato compounds as potential anticancer agents

Cueva-Alique

Muñoz-Moreno

Benabdelouahab

et al. 2016

Journal of Inorganic Biochemistry

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“…The formation of very large unstable aggregates in the presence of Group IV elements can be explained by the "metallic" properties of these elements and their high activity (compared to silicon) to form complexes with a coordination number greater than four [41], including bonds between the element and amine, carboxylate or phosphate groups [42][43][44]. This increased ability to form complex compounds results in the fast Fig.…”

Section: Resultsmentioning

confidence: 99%

The Effect of Titanium, Zirconium and Tin on the Growth of Diatom Synedra Acus and Morphology of Its Silica Valves

Basharina

Danilovtseva

Zelinskiy

et al. 2012

Silicon

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The effect of three Group IV metals (titanium, zirconium and tin) on the growth, morphology and chemical composition of the freshwater diatom Synedra acus subsp. radians (Kützing) Skabichevsky was studied and compared with germanium. The elements in their highest oxidation states were introduced into the culture medium in the form of hydroxides. Germanium was found to be toxic at ≥5 mol. % of the total Ge-Si content in the culture medium. In the presence of other elements, a slight decrease in the cell division rate was observed independent of the element within 1-15% content interval. The analysis of the obtained biomass and silica valves revealed the presence of all the added elements within the cells. However, only germanium was incorporated into the valves in considerable amounts. S. acus cultivation with the addition of 5% Group IV elements resulted in cells having the following aberrations in the structure of the silica valves: changes in valve shape, thickening of valves, alterations of the areolae rows, irregularity or absence of the areolae and a decrease in the mechanical strength of valves. Moreover, the effect of Group IV elements on silica formation was simulated in vitro using a synthetic polymer bearing polyamine and phosphate groups found in silaffines (proteins from Electronic supplementary material The online version of this article (diatom frustules). The studied elements were observed to provoke the formation of unstable silica particles in solution. We propose that the observed effects of germanium, titanium, zirconium and tin on diatom growth and structure are due to uncontrollable silica condensation.

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“…[14] In addition, hydrolysis and DNA studies of Cp2TiCl2 and Titanocene Y, with bis(4-nitrophenyl) phosphate (BNPP) have been studied (Figure 1). [15] They show that Cp2TiCl2 solutions promoted the hydrolysis of the activated phosphate di-and mono-esters, BNPP and NPP. However, no phosphate di-ester hydrolysis was observed in solutions containing the Titanocene Y species.…”

Section: Introductionmentioning

confidence: 99%

β-Diketonate Titanium Compounds Exhibiting High In Vitro Activity and Specific DNA Base Binding

et al. 2016

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Binding and hydrolysis studies of antitumoural titanocene dichloride and Titanocene Y with phosphate diesters

Cited by 28 publications

References 69 publications

Novel enantiopure cyclopentadienyl Ti(IV) oximato compounds as potential anticancer agents

Novel enantiopure cyclopentadienyl Ti(IV) oximato compounds as potential anticancer agents

The Effect of Titanium, Zirconium and Tin on the Growth of Diatom Synedra Acus and Morphology of Its Silica Valves

β-Diketonate Titanium Compounds Exhibiting High In Vitro Activity and Specific DNA Base Binding

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