Arene-Ruthenium(II) Complexes with Bioactive ortho-Hydroxydibenzoylmethane Ligands: Synthesis, Structure, and Cytotoxicity

Paul Joseph Dyson, Agnese Petrini, Tina Riedel
Wiley-Blackwell, 2017
Journal paper

The synthesis of a series of neutral arene-ruthenium (II) complexes (arene = p-cymene, hexamethylbenzene, and benzene) [(arene)Ru(HDB) Cl] derived from the reaction of the appropriate arene-ruthenium(II) dimers and ortho-hydroxydibenzoylmethane (HDBH), a potent inhibitor of cell proliferation, is described. In addition, related ionic complexes (arene)Ru(HDB)(PTA) (PTA = 1,3,5-triaza-7-phosphaadamantane) have been prepared. The structure of three complexes has been confirmed by X-ray crystallography. The cytotoxicity of the complexes has been evaluated against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorigenic human embryonic kidney (HEK293) cells, and compared to the free ligand and cisplatin. Two of the complexes, that is from the first series with p-cymene and hexamethylbenzene, display relevant activities against the cisplatin-resistant A2780cisR cancer cell line.

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Paul Joseph Dyson, Agnese Petrini, Tina Riedel
Wiley-Blackwell, 2017
Journal paper

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https://infoscience.epfl.ch/record/227696?ln=en

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Arene Osmium Complexes with Ethacrynic Acid-Modified Ligands: Synthesis, Characterization, and Evaluation of Intracellular Glutathione S-Transferase Inhibition and Antiproliferative Activity

Paul Joseph Dyson, Emilia Paunescu, Tina Riedel

Four arene osmium complexes were prepared containing derivatives of ethacrynic acid, a potent inhibitor of glutathione Stransferases, either by direct coordination or via N- or P-donor ligands. The complexes were characterized by spectroscopic and analytical methods and, for Os(eta(6)-p-cymene)(acetylacetonato)(2-(2,3-dichloro-4(2-ethylenebutanoyephenoxy)acetato) and Os(eta(6)-p-cymene)Cl-2(2-(2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetoxy)ethyl nicotinato), by single-crystal X-ray diffraction. The cytotoxicity of the complexes toward human ovarian cancer cells and nontumorous human embryonic kidney cells was investigated, and two of the complexes, for which ruthenium analogues are known, helped to delineate the influence of the metal ion. Inhibition studies of intracellular glutathione S-transferases (GSTs, detoxification enzymes implicated in drug resistance) indicate that the observed cytotoxicity of the complexes involves GST inhibition, as well as other targets following dissociation of the ethacrynic acid group from the osmium(II) ion.

American Chemical Society2016

Arene-ruthenium(II) complexes with pyrazole-based ligands bearing a pyridine moiety: Synthesis, structure, DFT calculations, and cytotoxicity

Paul Joseph Dyson, Farzaneh Fadaei Tirani, Mouna Hadiji

Two pyrazole-based ligands bearing a pyridine moiety, 3-methyl-1-(pyridin-2-yl)-5-pyrazolone (HLpy), and 3methyl-1-(pyridin-2-yl)-4-trifluoroacetyl-5-pyrazolone (HQpy,CF3), were prepared and fully characterized in the solid-state and the tautomerism of both ligands in solution was also rationalized by using Density Functional Theory. Neutral ruthenium(II) arene complexes of composition [Ru(arene)(Lpy)Cl] and [Ru(arene)(Qpy,CF3)Cl] [arene = p-cymene (cym) or hexamethylbenzene (hmb)]) were synthesized and characterized by IR, 1H, 13C, 15N and 19F NMR spectroscopy, elemental analysis and ESI mass spectrometry. The structures of complexes [Ru(hmb) (Lpy)Cl] and [Ru(hmb)(Qpy,CF3)Cl] were determined by X-ray crystallography, showing kappa 2-N,N'-coordination not only for Lpy but also for Qpy,CF3 ligand. DFT studies confirm that kappa 2O,O'-coordination, generally observed in metal complexes with 4-acyl-5-pyrazolone ligands, is not favored in this case. The cytotoxicity of ligands and complexes was evaluated against human ovarian carcinoma cells (A2780 and A2780cisR, cisplatin sensitive and cisplatin-resistant, respectively), and non-tumorous human embryonic kidney SV40 transformed (HEK293T) cells to reveal essentially equivalent activity in the cisplatin sensitive and cisplatin-resistant ovarian carcinoma cells.

ELSEVIER SCIENCE SA2021

Synthesis, Structure, and Anticancer Activity of Arene-Ruthenium(II) Complexes with Acylpyrazolones Bearing Aliphatic Groups in the Acyl Moiety

Paul Joseph Dyson, Tina Riedel, Rosario Scopelliti

A series of neutral ruthenium(II) arene complexes [(arene)Ru(Q(R))Cl] (arene = p-cymene (cym) or hexamethylbenzene (hmb)) containing 4-acyl-5-pyrazolonate Q(R) ligands with different electronic and steric substituents (R = 4-cyclohexyl, 4-stearoyl, or 4-adamantyl) and related ionic complexes [(arene)Ru(Q(R))(PTA)][PF6] (PTA = 1,3,5-triaza-7- phosphaadamantane) were synthesized and characterized by spectroscopy (IR, UVvis, ESI-MS, and H-1 and C-13 NMR), elemental analysis, X-ray crystallography, and density functional theory studies. The cytotoxicity of the proligands and metal complexes was evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. In general the cationic PTA-containing complexes are more cytotoxic than their neutral precursors with a chloride ligand in place of the PTA. Moreover, the complexes do not show cross-resistance and are essentially equally cytotoxic to both the A2780 and A2780cisR cell lines, although they only show limited selectivity toward the cancer cell lines.

American Chemical Society2016

X-ray crystallography

X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into ma

Ligand

In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves for

Coordination complex

A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the coordination centre, and a surrounding array of bound molecules or ions