Study of the influence of the metal complex on the cytotoxic activity of titanocene-functionalized mesoporous materials

Kaluđerović, Goran N.; Pérez‐Quintanilla, Damián; Sierra, Isabel; Prashar, Sanjiv; Hierro, Isabel del; Žižak, Željko; Juranić, Zorica D.; Fajardo, Mariano; Gómez‐Ruiz, Santiago

doi:10.1039/b919269g

Cited by 59 publications

(45 citation statements)

References 45 publications

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“…The other titanocene complexes 1e3 present very similar cytotoxic activity, albeit the trimethylsilyl-substituted derivative 3 is slightly more cytotoxic than the others (1 and 2) as was expected by the previous studies carried out by our group [56] and by McGowan and coworkers [57].…”

supporting

confidence: 69%

One ligand different metal complexes: Biological studies of titanium(IV), tin(IV) and gallium(III) derivatives with the 2,6-dimethoxypyridine-3-carboxylato ligand

Gómez‐Ruiz

Ceballos-Torres

Prashar

et al. 2011

Journal of Organometallic Chemistry

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supporting

confidence: 69%

One ligand different metal complexes: Biological studies of titanium(IV), tin(IV) and gallium(III) derivatives with the 2,6-dimethoxypyridine-3-carboxylato ligand

Gómez‐Ruiz

Ceballos-Torres

Prashar

et al. 2011

Journal of Organometallic Chemistry

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“…In this context, several studies have used the potential reactivity of –OH groups to promote the functionalization of mesoporous silica with anticancer titanocene derivatives. [ 27–29 ] Those studies confirmed the incorporation of cytotoxic titanocene derivatives in the structure of the mesoporous silica via the protonolysis of Si‐OH groups and the formation of Si‐O‐Ti fragments. The resulting materials demonstrated their potential use as chemotherapeutic agents in the treatment of solid tumors or as potential bone fillers for in situ treatment of bone tumors upon local implantations.…”

Section: Introductionmentioning

confidence: 84%

Surrounding Interactions on Phase Transition Temperature Promoted by Organometallic Complexes in Functionalized Poly(N‐isopropylacrylamide‐co‐dopamine methacrylamide) Copolymers

Wang

García‐Peñas

Gómez‐Ruiz

et al. 2020

Macro Chemistry & Physics

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a broad range of applications. Additional functionalities and other features can be obtained through the preparation of composites, hybrid materials, or functionalizing the original polymers. Some of these approaches focused on obtaining new kinds of catalysts, which are soluble in water, ecofriendly, and recyclable.Such procedures usually require numerous steps, such as the polymerization of glycidyl methacrylate, which is preceded by amination of the epoxy group with diethanolamine. [1] The resulting triethanolamine-pendant ligand can react with cyclopentadienyltitanium(IV) trichloride and derivatives, allowing the incorporation of the organometallic complex. [1] The combination of some organometallic complexes with poly(N-isopropyl acrylamide) (PNIPAM) could extend the properties associated with its thermoresponsive behavior. It is well known that its lower critical solution temperature (LCST) is around body temperature and can also provide reversibility. [2] Some approximations to this work were previously performed by atomic transfer radical polymerization (ATRP) using catalytic systems based on Cu. [3][4][5][6] The use of living chain-growth radical polymerization combined with step step-growth polymerizationThe functionalization of different structures with organometallic complexes provides exciting properties in terms of applicability due to its ability to provide multiple benefits for catalysis and biomedicine as well as in other fields. This work reports the direct, facile functionalization of copolymers based on N-isopropylacrylamide and dopamine methacrylamide with bis(cyclopentadienyl)titanium (IV) dichloride (Cp 2 TiCl 2 , Cp = η 5 -C 5 H 5 ), which can offer an easy preparation method in comparison with other functionalization procedures. In addition, the lower critical solution temperature (LCST) is studied through aqueous solutions of new structures, which is affected by the presence of the metallocene moieties. UV-vis spectroscopy shows an average of the LCST-behavior in comparison with rheology that provides essential information about the changes of the phase transition temperature associated with the composition of the polymeric chains and their interactions with the medium. Then, the inclusion of an organometallic complex along the polymeric chain can partially modify the phase transition temperature due to the interactions promoted by the organometallic complex of surroundings over the polymeric sections free of comonomer content.

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“…21 Substitution of the Cp groups with new protonated cyclic and aryl amines 19 and some other aryl and alkyl side chains (extensive work by Tacke et al . 16 and some others 22 ) increased the solubility in water of titanocene dichloride or improved the cytotoxicity. From these Cp-substituted titanocenes those named titanocene C and titanocene Y (Chart 1) were the more successful.…”

Section: Introductionmentioning

confidence: 99%

Titanocene–Phosphine Derivatives as Precursors to Cytotoxic Heterometallic TiAu₂and TiM (M = Pd, Pt) Compounds. Studies of Their Interactions with DNA

et al. 2011

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A series of tri- and bimetallic titanium-gold, titanium-palladium and titanium-platinum derivatives of general formulas [Ti{η5-C5H4(CH2)nPPh2(AuCl)}2].2THF n = 0 (1); n = 2 (2); n = 3 (3) and [TiCl2{η5-C5H4κ-(CH2)nPPh2}2(PtCl2)].2THF (M = Pd, n = 0 (4); n = 2 (5); n = 3 (6); M = Pt, n = 0 (7); n = 2 (8); n = 3 (9)) have been synthesized and characterized by different spectroscopic techniques and mass spectrometry. The molecular structures of compounds 1–9 have been investigated by means of density-functional calculations. The calculated IR spectra of the optimized structures fit well with the experimental IR data obtained for 1–9. The stability of the heterometallic compounds in deuterated solvents (CDCl3, d6-dmso, mixtures 50:50 d6-dmso/D2O, 1:99 d6-dmso/D2O at acidic pH and at neutral pH) has been evaluated by 31P and 1H NMR spectroscopy showing a higher stability for these compounds than for Cp2TiCl2 or precursors [Ti{η5-C5H4(CH2)nPPh2}2]. The new compounds display a lower acidity (1 to 2 units) than Cp2TiCl2. The decomposition products have been identified over time. Complexes 1–9 have been tested as potential anticancer agents and their cytotoxicity properties were evaluated in vitro against HeLa human cervical carcinoma and DU-145 human prostate cancer cells. TiAu2 and TiPd compounds were highly cytotoxic for these two cell lines. The interactions of the compounds with Calf Thymus DNA have been evaluated by Thermal Denaturation (1–9) and by Circular Dichroism (1, 3, 4, 7) spectroscopic methods. All these complexes show a stronger interaction with DNA than that displayed by Cp2TiCl2 at neutral pH. The data is consistent with electrostatic interactions with DNA for TiAu2 compounds and for a covalent binding mode for TiM (M = Pd, Pt) complexes.

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Study of the influence of the metal complex on the cytotoxic activity of titanocene-functionalized mesoporous materials

Cited by 59 publications

References 45 publications

One ligand different metal complexes: Biological studies of titanium(IV), tin(IV) and gallium(III) derivatives with the 2,6-dimethoxypyridine-3-carboxylato ligand

One ligand different metal complexes: Biological studies of titanium(IV), tin(IV) and gallium(III) derivatives with the 2,6-dimethoxypyridine-3-carboxylato ligand

Surrounding Interactions on Phase Transition Temperature Promoted by Organometallic Complexes in Functionalized Poly(N‐isopropylacrylamide‐co‐dopamine methacrylamide) Copolymers

Titanocene–Phosphine Derivatives as Precursors to Cytotoxic Heterometallic TiAu₂and TiM (M = Pd, Pt) Compounds. Studies of Their Interactions with DNA

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Study of the influence of the metal complex on the cytotoxic activity of titanocene-functionalized mesoporous materials

Cited by 59 publications

References 45 publications

One ligand different metal complexes: Biological studies of titanium(IV), tin(IV) and gallium(III) derivatives with the 2,6-dimethoxypyridine-3-carboxylato ligand

One ligand different metal complexes: Biological studies of titanium(IV), tin(IV) and gallium(III) derivatives with the 2,6-dimethoxypyridine-3-carboxylato ligand

Surrounding Interactions on Phase Transition Temperature Promoted by Organometallic Complexes in Functionalized Poly(N‐isopropylacrylamide‐co‐dopamine methacrylamide) Copolymers

Titanocene–Phosphine Derivatives as Precursors to Cytotoxic Heterometallic TiAu2and TiM (M = Pd, Pt) Compounds. Studies of Their Interactions with DNA

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Titanocene–Phosphine Derivatives as Precursors to Cytotoxic Heterometallic TiAu₂and TiM (M = Pd, Pt) Compounds. Studies of Their Interactions with DNA