Synthesis, characterization and crystal structures of cyclometallated palladium (II) compounds containing difunctional ligands with [P,P], [As,As], [N,N], [P,As], [P,N] and [P,O] donor atoms

Ares, Raquel; Vázquez‐García, Digna; López‐Torres, Margarita; Fernández, Alberto; Gómez-Blanco, Nina; Vila, José M.; Fernández, Jesús J.

doi:10.1016/j.jorganchem.2008.08.023

Cited by 12 publications

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References 67 publications

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“…In the case of complex 2a , even though the bridging ligand 1-diphenylphosphino-2-diphenylarsinoethane is asymmetric, the dinuclear molecule is crystallographically centrosymmetric; this is caused by the disordered distribution of the P and As atoms (population parameter 50%) and by the quasi centrosymmetric nature of the compound, which gives similar environments for both P and As. This behavior has been observed in other complexes derived from the arsinophosphine ligand . In the crystal of 4a the complete molecule is generated by a C 2 symmetry axis that passes through the iron atom and is parallel to the two cyclopentadienyl rings.…”

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confidence: 99%

Dinuclear Ru^II(bipy)₂Derivatives: Structural, Biological, and in Vivo Zebrafish Toxicity Evaluation

et al. 2017

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Ruthenium-based drugs exhibit interesting properties as potential anticancer pharmaceuticals. We herein present the synthesis and characterization of a new family of ruthenium complexes with formulas [{Ru(bipy)}(μ-L)][CFSO] (L = bptz, 1a) and [{Ru(bipy)}(μ-L)][CFSO] (L = arphos, 2a; dppb, 3a; dppf, 4a), which were synthesized from the Ru(II) precursor compound cis-Ru(bipy)Cl. The complexes were characterized by elemental analysis, mass spectrometry, H andP{H} NMR, IR spectroscopy, and conductivity measurements. The molecular structures for three Ru(II) compounds were determined by single-crystal X-ray diffraction. The newly developed compounds interact with CT-DNA by intercalation, in particular, 2a, 3a, and 4a, which also seemed to induce some extent of DNA degradation. This effect seemed to be related with the formation of reactive oxygen species. The cytotoxic activity was evaluated against A2780, MCF7, and MDAMB231 human tumor cells. Compounds 2a and 4a were the most cytotoxic with activity compared to cisplatin (∼2 μM, 72 h) in the A2780 cisplatin sensitive cells. All the compounds induced A2780 cell death by apoptosis, however, to a lesser extent for compounds 4a and 2a. For these compounds, the mechanism of cell death in addition to apoptosis seemed to involve autophagy. In vivo toxicity was evaluated using the zebrafish embryo model. LC estimates varied from 5.397 (3a) to 39.404 (1a) mg/L. Considering the in vivo toxicity in zebrafish embryos and the in vitro cytotoxicity in cancer cells, compound 1a seems to be the safest having no effect on dechirionation and presenting a good antiproliferative activity against ovarian carcinoma cells.

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Section: Resultsmentioning

confidence: 99%

Dinuclear Ru^II(bipy)₂Derivatives: Structural, Biological, and in Vivo Zebrafish Toxicity Evaluation

et al. 2017

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Synthesis of Cyclopalladated Derivatives of (E)‐N‐Benzylidene‐2‐(2,6‐dichlorophenyl)ethanamine and Their Reactivity towards Monodentate and Symmetric Bidentate Lewis Bases

et al. 2011

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Treatment of the monoimine (E)-N-benzylidene-2-(2,6-dichlorophenyl)ethanamine (1) with a stoichiometric amount of Pd(OAc) 2 in acetic acid at 60°C under nitrogen produced the corresponding acetato-bridged endo five-membered ortho-cyclopalladated dimer [Pd{C 6 H 4 CH=N(CH 2 ) 2 (2,6-Cl 2 C 6 H 3 )}(μ-OAc)] 2 (2), which was isolated in pure form in 80 % yield. Reaction of 2 with an excess of LiCl in acetone gave rise to the corresponding chlorido-bridged cyclopalladated dimer [Pd{C 6 H 4 CH=N(CH 2 ) 2 (2,6-Cl 2 C 6 H 3 )}(μ-

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On the Reactivity of Platina‐β‐diketone and Acetylplatinum(II) Complexes toward 2‐(Diphenylphosphanyl)benzaldehyde and Its Dioxolane Derivative

et al. 2013

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The dinuclear platina‐β‐diketone [Pt2{(COMe)2H}2(μ‐Cl)2] (1) reacts with four and two equivalents of 2‐[2‐(diphenylphosphanyl)phenyl]‐1,3‐dioxolane (L1) to yield [Pt(COMe)Cl(PPh2{o‐C6H4CH(O2C2H4)}‐κP)2] (3) and [Pt(COMe)Cl(PPh2{o‐C6H4CH(O2C2H4)}‐κP,κO)] (4), respectively. The weak Pt–O bond in 4 can be easily broken up by stronger donors. Thus, complex 4 reacts with PPh3 to yield [Pt(COMe)Cl(PPh3)(PPh2{o‐C6H4CH(O2C2H4)}‐κP)] (5) and [Pt(COMe)Cl(PPh3)2] (6) as well as with L1 to yield 3. Diacetylbis(amine)platinum(II) complexes cis‐[Pt(COMe)2(NH2R)2] (R = Bn, 2a; R = Et, 2b; Bn = benzyl) react with L1 with the substitution of one amine ligand to yield [Pt(COMe)2(NH2R)(PPh2{o‐C6H4CH(O2C2H4)}‐κP)] (R = Bn, 7a; R = Et, 7b). The unprotected 2‐(diphenylphosphanyl)benzaldehyde (L2) reacts with the platina‐β‐diketone 1 by oxidative C–H addition followed by reductive elimination of acetaldehyde to form [PtCl{PPh2(o‐C6H4CO)‐κP,κC}{PPh2(o‐C6H4CHO)‐κP}] (8). On the other hand, the reactions of diacetylbis(amine)platinum(II) complexes 2a/b and L2 proceeded with Schiff base formation and, thus, yielded complexes bearing hemiaminal–phosphane ligands, [Pt(COMe)2(PPh2{o‐C6H4CH(OH)(NHR)}‐κP,κN)] (R = Bn, 9a; R = Et, 9b), and imine–phosphane ligands, [Pt(COMe)2{PPh2(o‐C6H4CH=NR)‐κP,κN}] (R = Bn, 10a; R = Et, 10b). The identities of all platinum complexes were unambiguously proved by microanalyses, high‐resolution mass spectrometric investigations, NMR (1H, 13C, 31P, 195Pt) and IR spectroscopy, and single‐crystal X‐ray diffraction analyses (for 4, 9a). The differences in the reactivity of the aldehyde–phosphane L2 and its acetal‐protected derivative L1 are discussed.

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Synthesis, characterization and crystal structures of cyclometallated palladium (II) compounds containing difunctional ligands with [P,P], [As,As], [N,N], [P,As], [P,N] and [P,O] donor atoms

Cited by 12 publications

References 67 publications

Dinuclear Ru^II(bipy)₂Derivatives: Structural, Biological, and in Vivo Zebrafish Toxicity Evaluation

Dinuclear Ru^II(bipy)₂Derivatives: Structural, Biological, and in Vivo Zebrafish Toxicity Evaluation

Synthesis of Cyclopalladated Derivatives of (E)‐N‐Benzylidene‐2‐(2,6‐dichlorophenyl)ethanamine and Their Reactivity towards Monodentate and Symmetric Bidentate Lewis Bases

On the Reactivity of Platina‐β‐diketone and Acetylplatinum(II) Complexes toward 2‐(Diphenylphosphanyl)benzaldehyde and Its Dioxolane Derivative

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Synthesis, characterization and crystal structures of cyclometallated palladium (II) compounds containing difunctional ligands with [P,P], [As,As], [N,N], [P,As], [P,N] and [P,O] donor atoms

Cited by 12 publications

References 67 publications

Dinuclear RuII(bipy)2Derivatives: Structural, Biological, and in Vivo Zebrafish Toxicity Evaluation

Dinuclear RuII(bipy)2Derivatives: Structural, Biological, and in Vivo Zebrafish Toxicity Evaluation

Synthesis of Cyclopalladated Derivatives of (E)‐N‐Benzylidene‐2‐(2,6‐dichlorophenyl)ethanamine and Their Reactivity towards Monodentate and Symmetric Bidentate Lewis Bases

On the Reactivity of Platina‐β‐diketone and Acetylplatinum(II) Complexes toward 2‐(Diphenylphosphanyl)benzaldehyde and Its Dioxolane Derivative

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Dinuclear Ru^II(bipy)₂Derivatives: Structural, Biological, and in Vivo Zebrafish Toxicity Evaluation

Dinuclear Ru^II(bipy)₂Derivatives: Structural, Biological, and in Vivo Zebrafish Toxicity Evaluation