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Paul J Dyson - One of the best experts on this subject based on the ideXlab platform.
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from sunscreen to anticancer agent ruthenium ii arene avobenzone complexes display potent anticancer activity
Organometallics, 2016Co-Authors: Riccardo Pettinari, Fabio Marchetti, Agnese Petrini, Claudio Pettinari, Giulio Lupidi, Piotr Smolenski, Rosario Scopelliti, Tina Riedel, Paul J DysonAbstract:A series of ruthenium(II) arene derivatives (arene = cymene (cym), Hexamethylbenzene (hmb)) containing avobenzone (1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione, AVBH) and PTA (1,3,5-triaza-7-phosphaadamantane) or PTA-Me (N-methyl-1,3,5-triaza-7-phosphaadamantane cation) have been synthesized and fully characterized. Three types of complexes have been obtained: i.e., neutral [Ru(arene)(AVB)Cl] (1, arene = cym; 2, arene = hmb), monocationic [Ru(arene)(AVB)(PTA)][SO3CF3] (3, arene = cym; 4, arene = hmb), and dicationic [Ru(arene)(AVB)(PTA-Me)][SO3CF3][BF4] (5, arene = cym; 6, arene = hmb). The solid-state structures of 1 and 2 were determined by single-crystal X-ray diffraction. The cytotoxicity of the complexes has been evaluated in vitro against human ovarian carcinoma cells, A2780 and A2780cisR, as well as against nontumorous Human Embryonic Kidney (HEK293) cells. The ionic complexes with hydrophilic PTA and PTA-Me ligands in 3–6 are considerably more active than the neutral complexes 1 and 2.
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Synthesis, Structure, and Anticancer Activity of Arene–Ruthenium(II) Complexes with Acylpyrazolones Bearing Aliphatic Groups in the Acyl Moiety
2016Co-Authors: Jessica Palmucci, Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Rosario Scopelliti, Tina Riedel, Bruno Therrien, Agustin Galindo, Paul J DysonAbstract:A series of neutral ruthenium(II) arene complexes [(arene)Ru(QR)Cl] (arene = p-cymene (cym) or Hexamethylbenzene (hmb)) containing 4-acyl-5-pyrazolonate QR ligands with different electronic and steric substituents (R = 4-cyclohexyl, 4-stearoyl, or 4-adamantyl) and related ionic complexes [(arene)Ru(QR)(PTA)][PF6] (PTA = 1,3,5-triaza-7-phosphaadamantane) were synthesized and characterized by spectroscopy (IR, UV–vis, ESI-MS, and 1H and 13C 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
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Ruthenium(II)–Arene RAPTA Type Complexes Containing Curcumin and Bisdemethoxycurcumin Display Potent and Selective Anticancer Activity
2015Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Giulio Lupidi, Rosario Scopelliti, Tina Riedel, Francesca Condello, Suman Mukhopadhyay, Paul J DysonAbstract:A series of novel ruthenium(II) arene RAPTA type derivatives (arene = cymene, Hexamethylbenzene) containing curcumin-based ligands (curcH = curcumin, bdcurcH = bisdemethoxycurcumin) and PTA (1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized. The solid-state structures of [Ru(cym)(curc)(PTA)][SO3CF3], [Ru(hmb)(curc)(PTA)][SO3CF3], and [Ru(hmb)(bdcurc)(PTA)][SO3CF3] have been determined by single-crystal X-ray diffraction. The antitumor activity of the complexes has been evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. The correlation of the cytotoxicity upon switching the curcumin-based ligands, i.e. curcumin vs bisdemethoxycurcumin, is not straightforward. In contrast, the PTA ligand greatly enhances the activity and selectivity of ruthenium compounds in comparison to previously reported compounds
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Ruthenium(II)–Arene RAPTA Type Complexes Containing Curcumin and Bisdemethoxycurcumin Display Potent and Selective Anticancer Activity
Organometallics, 2014Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Giulio Lupidi, Rosario Scopelliti, Tina Riedel, Francesca Condello, Suman Mukhopadhyay, Paul J DysonAbstract:A series of novel ruthenium(II) arene RAPTA type derivatives (arene = cymene, Hexamethylbenzene) containing curcumin-based ligands (curcH = curcumin, bdcurcH = bisdemethoxycurcumin) and PTA (1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized. The solid-state structures of [Ru(cym)(curc)(PTA)][SO3CF3], [Ru(hmb)(curc)(PTA)][SO3CF3], and [Ru(hmb)(bdcurc)(PTA)][SO3CF3] have been determined by single-crystal X-ray diffraction. The antitumor activity of the complexes has been evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. The correlation of the cytotoxicity upon switching the curcumin-based ligands, i.e. curcumin vs bisdemethoxycurcumin, is not straightforward. In contrast, the PTA ligand greatly enhances the activity and selectivity of ruthenium compounds in comparison to previously reported compounds.
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ruthenium ii arene rapta type complexes containing curcumin and bisdemethoxycurcumin display potent and selective anticancer activity
Organometallics, 2014Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Giulio Lupidi, Rosario Scopelliti, Tina Riedel, Francesca Condello, Suman Mukhopadhyay, Paul J DysonAbstract:A series of novel ruthenium(II) arene RAPTA type derivatives (arene = cymene, Hexamethylbenzene) containing curcumin-based ligands (curcH = curcumin, bdcurcH = bisdemethoxycurcumin) and PTA (1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized. The solid-state structures of [Ru(cym)(curc)(PTA)][SO3CF3], [Ru(hmb)(curc)(PTA)][SO3CF3], and [Ru(hmb)(bdcurc)(PTA)][SO3CF3] have been determined by single-crystal X-ray diffraction. The antitumor activity of the complexes has been evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. The correlation of the cytotoxicity upon switching the curcumin-based ligands, i.e. curcumin vs bisdemethoxycurcumin, is not straightforward. In contrast, the PTA ligand greatly enhances the activity and selectivity of ruthenium compounds in comparison to previously reported compounds.
Riccardo Pettinari - One of the best experts on this subject based on the ideXlab platform.
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from sunscreen to anticancer agent ruthenium ii arene avobenzone complexes display potent anticancer activity
Organometallics, 2016Co-Authors: Riccardo Pettinari, Fabio Marchetti, Agnese Petrini, Claudio Pettinari, Giulio Lupidi, Piotr Smolenski, Rosario Scopelliti, Tina Riedel, Paul J DysonAbstract:A series of ruthenium(II) arene derivatives (arene = cymene (cym), Hexamethylbenzene (hmb)) containing avobenzone (1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione, AVBH) and PTA (1,3,5-triaza-7-phosphaadamantane) or PTA-Me (N-methyl-1,3,5-triaza-7-phosphaadamantane cation) have been synthesized and fully characterized. Three types of complexes have been obtained: i.e., neutral [Ru(arene)(AVB)Cl] (1, arene = cym; 2, arene = hmb), monocationic [Ru(arene)(AVB)(PTA)][SO3CF3] (3, arene = cym; 4, arene = hmb), and dicationic [Ru(arene)(AVB)(PTA-Me)][SO3CF3][BF4] (5, arene = cym; 6, arene = hmb). The solid-state structures of 1 and 2 were determined by single-crystal X-ray diffraction. The cytotoxicity of the complexes has been evaluated in vitro against human ovarian carcinoma cells, A2780 and A2780cisR, as well as against nontumorous Human Embryonic Kidney (HEK293) cells. The ionic complexes with hydrophilic PTA and PTA-Me ligands in 3–6 are considerably more active than the neutral complexes 1 and 2.
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Synthesis, Structure, and Anticancer Activity of Arene–Ruthenium(II) Complexes with Acylpyrazolones Bearing Aliphatic Groups in the Acyl Moiety
2016Co-Authors: Jessica Palmucci, Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Rosario Scopelliti, Tina Riedel, Bruno Therrien, Agustin Galindo, Paul J DysonAbstract:A series of neutral ruthenium(II) arene complexes [(arene)Ru(QR)Cl] (arene = p-cymene (cym) or Hexamethylbenzene (hmb)) containing 4-acyl-5-pyrazolonate QR ligands with different electronic and steric substituents (R = 4-cyclohexyl, 4-stearoyl, or 4-adamantyl) and related ionic complexes [(arene)Ru(QR)(PTA)][PF6] (PTA = 1,3,5-triaza-7-phosphaadamantane) were synthesized and characterized by spectroscopy (IR, UV–vis, ESI-MS, and 1H and 13C 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
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Arene–Ruthenium(II) Acylpyrazolonato Complexes: Apoptosis-Promoting Effects on Human Cancer Cells
2015Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Brian W. Skelton, Allan H. White, Laura Bonfili, Massimiliano Cuccioloni, Matteo Mozzicafreddo, Valentina Cecarini, Mauro AngelettiAbstract:A series of ruthenium(II) arene complexes with the 4-(biphenyl-4-carbonyl)-3-methyl-1-phenyl-5-pyrazolonate ligand, and related 1,3,5-triaza-7-phosphaadamantane (PTA) derivatives, has been synthesized. The compounds have been characterized by NMR and IR spectroscopy, ESI mass spectrometry, elemental analysis, and X-ray crystallography. Antiproliferative activity in four human cancer cell lines was determined by MTT assay, yielding dose- and cancer cell line-dependent IC50 values of 9–34 μM for three Hexamethylbenzene–ruthenium complexes, whereas the other metal complexes were much less active. Apoptosis was the mechanism involved in the anticancer activity of such compounds. In fact, the Hexamethylbenzene–ruthenium complexes activated caspase activity, with consequent DNA fragmentation, accumulation of pro-apoptotic proteins (p27, p53, p89 PARP fragments), and the concomitant down-regulation of antiapoptotic protein Bcl-2. Biosensor-based binding studies indicated that the ancillary ligands were critical in determining the DNA binding affinities, and competition binding experiments further characterized the nature of the interaction
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Ruthenium(II)–Arene RAPTA Type Complexes Containing Curcumin and Bisdemethoxycurcumin Display Potent and Selective Anticancer Activity
2015Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Giulio Lupidi, Rosario Scopelliti, Tina Riedel, Francesca Condello, Suman Mukhopadhyay, Paul J DysonAbstract:A series of novel ruthenium(II) arene RAPTA type derivatives (arene = cymene, Hexamethylbenzene) containing curcumin-based ligands (curcH = curcumin, bdcurcH = bisdemethoxycurcumin) and PTA (1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized. The solid-state structures of [Ru(cym)(curc)(PTA)][SO3CF3], [Ru(hmb)(curc)(PTA)][SO3CF3], and [Ru(hmb)(bdcurc)(PTA)][SO3CF3] have been determined by single-crystal X-ray diffraction. The antitumor activity of the complexes has been evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. The correlation of the cytotoxicity upon switching the curcumin-based ligands, i.e. curcumin vs bisdemethoxycurcumin, is not straightforward. In contrast, the PTA ligand greatly enhances the activity and selectivity of ruthenium compounds in comparison to previously reported compounds
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Ruthenium(II)–Arene RAPTA Type Complexes Containing Curcumin and Bisdemethoxycurcumin Display Potent and Selective Anticancer Activity
Organometallics, 2014Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Giulio Lupidi, Rosario Scopelliti, Tina Riedel, Francesca Condello, Suman Mukhopadhyay, Paul J DysonAbstract:A series of novel ruthenium(II) arene RAPTA type derivatives (arene = cymene, Hexamethylbenzene) containing curcumin-based ligands (curcH = curcumin, bdcurcH = bisdemethoxycurcumin) and PTA (1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized. The solid-state structures of [Ru(cym)(curc)(PTA)][SO3CF3], [Ru(hmb)(curc)(PTA)][SO3CF3], and [Ru(hmb)(bdcurc)(PTA)][SO3CF3] have been determined by single-crystal X-ray diffraction. The antitumor activity of the complexes has been evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. The correlation of the cytotoxicity upon switching the curcumin-based ligands, i.e. curcumin vs bisdemethoxycurcumin, is not straightforward. In contrast, the PTA ligand greatly enhances the activity and selectivity of ruthenium compounds in comparison to previously reported compounds.
Fabio Marchetti - One of the best experts on this subject based on the ideXlab platform.
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from sunscreen to anticancer agent ruthenium ii arene avobenzone complexes display potent anticancer activity
Organometallics, 2016Co-Authors: Riccardo Pettinari, Fabio Marchetti, Agnese Petrini, Claudio Pettinari, Giulio Lupidi, Piotr Smolenski, Rosario Scopelliti, Tina Riedel, Paul J DysonAbstract:A series of ruthenium(II) arene derivatives (arene = cymene (cym), Hexamethylbenzene (hmb)) containing avobenzone (1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione, AVBH) and PTA (1,3,5-triaza-7-phosphaadamantane) or PTA-Me (N-methyl-1,3,5-triaza-7-phosphaadamantane cation) have been synthesized and fully characterized. Three types of complexes have been obtained: i.e., neutral [Ru(arene)(AVB)Cl] (1, arene = cym; 2, arene = hmb), monocationic [Ru(arene)(AVB)(PTA)][SO3CF3] (3, arene = cym; 4, arene = hmb), and dicationic [Ru(arene)(AVB)(PTA-Me)][SO3CF3][BF4] (5, arene = cym; 6, arene = hmb). The solid-state structures of 1 and 2 were determined by single-crystal X-ray diffraction. The cytotoxicity of the complexes has been evaluated in vitro against human ovarian carcinoma cells, A2780 and A2780cisR, as well as against nontumorous Human Embryonic Kidney (HEK293) cells. The ionic complexes with hydrophilic PTA and PTA-Me ligands in 3–6 are considerably more active than the neutral complexes 1 and 2.
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Synthesis, Structure, and Anticancer Activity of Arene–Ruthenium(II) Complexes with Acylpyrazolones Bearing Aliphatic Groups in the Acyl Moiety
2016Co-Authors: Jessica Palmucci, Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Rosario Scopelliti, Tina Riedel, Bruno Therrien, Agustin Galindo, Paul J DysonAbstract:A series of neutral ruthenium(II) arene complexes [(arene)Ru(QR)Cl] (arene = p-cymene (cym) or Hexamethylbenzene (hmb)) containing 4-acyl-5-pyrazolonate QR ligands with different electronic and steric substituents (R = 4-cyclohexyl, 4-stearoyl, or 4-adamantyl) and related ionic complexes [(arene)Ru(QR)(PTA)][PF6] (PTA = 1,3,5-triaza-7-phosphaadamantane) were synthesized and characterized by spectroscopy (IR, UV–vis, ESI-MS, and 1H and 13C 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
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Arene–Ruthenium(II) Acylpyrazolonato Complexes: Apoptosis-Promoting Effects on Human Cancer Cells
2015Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Brian W. Skelton, Allan H. White, Laura Bonfili, Massimiliano Cuccioloni, Matteo Mozzicafreddo, Valentina Cecarini, Mauro AngelettiAbstract:A series of ruthenium(II) arene complexes with the 4-(biphenyl-4-carbonyl)-3-methyl-1-phenyl-5-pyrazolonate ligand, and related 1,3,5-triaza-7-phosphaadamantane (PTA) derivatives, has been synthesized. The compounds have been characterized by NMR and IR spectroscopy, ESI mass spectrometry, elemental analysis, and X-ray crystallography. Antiproliferative activity in four human cancer cell lines was determined by MTT assay, yielding dose- and cancer cell line-dependent IC50 values of 9–34 μM for three Hexamethylbenzene–ruthenium complexes, whereas the other metal complexes were much less active. Apoptosis was the mechanism involved in the anticancer activity of such compounds. In fact, the Hexamethylbenzene–ruthenium complexes activated caspase activity, with consequent DNA fragmentation, accumulation of pro-apoptotic proteins (p27, p53, p89 PARP fragments), and the concomitant down-regulation of antiapoptotic protein Bcl-2. Biosensor-based binding studies indicated that the ancillary ligands were critical in determining the DNA binding affinities, and competition binding experiments further characterized the nature of the interaction
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Ruthenium(II)–Arene RAPTA Type Complexes Containing Curcumin and Bisdemethoxycurcumin Display Potent and Selective Anticancer Activity
2015Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Giulio Lupidi, Rosario Scopelliti, Tina Riedel, Francesca Condello, Suman Mukhopadhyay, Paul J DysonAbstract:A series of novel ruthenium(II) arene RAPTA type derivatives (arene = cymene, Hexamethylbenzene) containing curcumin-based ligands (curcH = curcumin, bdcurcH = bisdemethoxycurcumin) and PTA (1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized. The solid-state structures of [Ru(cym)(curc)(PTA)][SO3CF3], [Ru(hmb)(curc)(PTA)][SO3CF3], and [Ru(hmb)(bdcurc)(PTA)][SO3CF3] have been determined by single-crystal X-ray diffraction. The antitumor activity of the complexes has been evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. The correlation of the cytotoxicity upon switching the curcumin-based ligands, i.e. curcumin vs bisdemethoxycurcumin, is not straightforward. In contrast, the PTA ligand greatly enhances the activity and selectivity of ruthenium compounds in comparison to previously reported compounds
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Ruthenium(II)–Arene RAPTA Type Complexes Containing Curcumin and Bisdemethoxycurcumin Display Potent and Selective Anticancer Activity
Organometallics, 2014Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Giulio Lupidi, Rosario Scopelliti, Tina Riedel, Francesca Condello, Suman Mukhopadhyay, Paul J DysonAbstract:A series of novel ruthenium(II) arene RAPTA type derivatives (arene = cymene, Hexamethylbenzene) containing curcumin-based ligands (curcH = curcumin, bdcurcH = bisdemethoxycurcumin) and PTA (1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized. The solid-state structures of [Ru(cym)(curc)(PTA)][SO3CF3], [Ru(hmb)(curc)(PTA)][SO3CF3], and [Ru(hmb)(bdcurc)(PTA)][SO3CF3] have been determined by single-crystal X-ray diffraction. The antitumor activity of the complexes has been evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. The correlation of the cytotoxicity upon switching the curcumin-based ligands, i.e. curcumin vs bisdemethoxycurcumin, is not straightforward. In contrast, the PTA ligand greatly enhances the activity and selectivity of ruthenium compounds in comparison to previously reported compounds.
Therrien Bruno - One of the best experts on this subject based on the ideXlab platform.
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Arene-Ruthenium(II) Complexes with Bioactive ortho-Hydroxydibenzoylmethane Ligands: Synthesis, Structure, and Cytotoxicity
'Wiley', 2017Co-Authors: Pettinari Riccardo, Therrien Bruno, Petrini Agnese, Marchetti Fabio, Pettinari Claudio, Riedel Tina, Dyson, Paul J.Abstract: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)](SO3CF3) (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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Arene Ruthenium(II) Complexes with the Bioactive ortho-Hydroxydibenzoylmethane Ligand: Synthesis, Structure and Cytotoxicity
'Wiley', 2017Co-Authors: Pettinari Riccardo, Dyson, Paul J., Therrien Bruno, Petrini Agnese, Marchetti Fabio, Pettinari Claudio, Riedel TinaAbstract: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)][SO3CF3] (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 non-tumorigenic human embryonic kidney (HEK293) cells and compared to the free ligand and cisplatin. Two of the complexes, i.e. from the first series with p-cymene and Hexamethylbenzene, display relevant activities against the cisplatin resistant A2789cisR cancer cell line
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Synthesis, Structure, and Anticancer Activity of Arene-Ruthenium(II) Complexes with Acylpyrazolones Bearing Aliphatic Groups in the Acyl Moiety
'American Chemical Society (ACS)', 2017Co-Authors: Palmucci Jessica, Therrien Bruno, Pettinari Riccardo, Marchetti Fabio, Pettinari Claudio, Riedel Tina, Scopelliti Rosario, Galindo Agustin, Dyson, Paul J.Abstract: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
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Dichlorido(furfurylamine-κN)(η6-Hexamethylbenzene)ruthenium(II)
2012Co-Authors: Garci Amine, Suss-fink Georg, Thai Trieu-tien, Therrien BrunoAbstract:The single-crystal X-ray structure analysis of [RuCl2(C12H18)(C5H7NO)] reveals a distorted piano-stool geometry around the RuII atom, with a Hexamethylbenzene ligand, two chloride ligands and a furfurylamine ligand, the latter coordinating through the amine group. In the crystal, a dimeric structure is observed as a result of N-H...Cl interactions between two symmetry-related molecules
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[Bis(2-pyridyl-κN)amine]chlorido(η6-Hexamethylbenzene)ruthenium(II) hexafluoridophosphate dichloromethane solvate
2012Co-Authors: Gupta Gajendra, Therrien Bruno, Kim JinkwomAbstract:In the title half-sandwich complex, [RuCl(η6-C12H18)(C10H9N3)]PF6•CH2Cl2, the ruthenium(II) ion is four-coordinated by a chloro, a Hexamethylbenzene and a bidentate N, N'-chelating di(pyridin-2-yl)amine ligand. In the crystal, the amino N-H group forms a hydrogen bond with the chloro ligand of a neighbouring complex, thus forming chains along the b axis. Weak intermolecular C-H...F and C-H... Cl contacts are also observed
Claudio Pettinari - One of the best experts on this subject based on the ideXlab platform.
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from sunscreen to anticancer agent ruthenium ii arene avobenzone complexes display potent anticancer activity
Organometallics, 2016Co-Authors: Riccardo Pettinari, Fabio Marchetti, Agnese Petrini, Claudio Pettinari, Giulio Lupidi, Piotr Smolenski, Rosario Scopelliti, Tina Riedel, Paul J DysonAbstract:A series of ruthenium(II) arene derivatives (arene = cymene (cym), Hexamethylbenzene (hmb)) containing avobenzone (1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione, AVBH) and PTA (1,3,5-triaza-7-phosphaadamantane) or PTA-Me (N-methyl-1,3,5-triaza-7-phosphaadamantane cation) have been synthesized and fully characterized. Three types of complexes have been obtained: i.e., neutral [Ru(arene)(AVB)Cl] (1, arene = cym; 2, arene = hmb), monocationic [Ru(arene)(AVB)(PTA)][SO3CF3] (3, arene = cym; 4, arene = hmb), and dicationic [Ru(arene)(AVB)(PTA-Me)][SO3CF3][BF4] (5, arene = cym; 6, arene = hmb). The solid-state structures of 1 and 2 were determined by single-crystal X-ray diffraction. The cytotoxicity of the complexes has been evaluated in vitro against human ovarian carcinoma cells, A2780 and A2780cisR, as well as against nontumorous Human Embryonic Kidney (HEK293) cells. The ionic complexes with hydrophilic PTA and PTA-Me ligands in 3–6 are considerably more active than the neutral complexes 1 and 2.
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Synthesis, Structure, and Anticancer Activity of Arene–Ruthenium(II) Complexes with Acylpyrazolones Bearing Aliphatic Groups in the Acyl Moiety
2016Co-Authors: Jessica Palmucci, Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Rosario Scopelliti, Tina Riedel, Bruno Therrien, Agustin Galindo, Paul J DysonAbstract:A series of neutral ruthenium(II) arene complexes [(arene)Ru(QR)Cl] (arene = p-cymene (cym) or Hexamethylbenzene (hmb)) containing 4-acyl-5-pyrazolonate QR ligands with different electronic and steric substituents (R = 4-cyclohexyl, 4-stearoyl, or 4-adamantyl) and related ionic complexes [(arene)Ru(QR)(PTA)][PF6] (PTA = 1,3,5-triaza-7-phosphaadamantane) were synthesized and characterized by spectroscopy (IR, UV–vis, ESI-MS, and 1H and 13C 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
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Arene–Ruthenium(II) Acylpyrazolonato Complexes: Apoptosis-Promoting Effects on Human Cancer Cells
2015Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Brian W. Skelton, Allan H. White, Laura Bonfili, Massimiliano Cuccioloni, Matteo Mozzicafreddo, Valentina Cecarini, Mauro AngelettiAbstract:A series of ruthenium(II) arene complexes with the 4-(biphenyl-4-carbonyl)-3-methyl-1-phenyl-5-pyrazolonate ligand, and related 1,3,5-triaza-7-phosphaadamantane (PTA) derivatives, has been synthesized. The compounds have been characterized by NMR and IR spectroscopy, ESI mass spectrometry, elemental analysis, and X-ray crystallography. Antiproliferative activity in four human cancer cell lines was determined by MTT assay, yielding dose- and cancer cell line-dependent IC50 values of 9–34 μM for three Hexamethylbenzene–ruthenium complexes, whereas the other metal complexes were much less active. Apoptosis was the mechanism involved in the anticancer activity of such compounds. In fact, the Hexamethylbenzene–ruthenium complexes activated caspase activity, with consequent DNA fragmentation, accumulation of pro-apoptotic proteins (p27, p53, p89 PARP fragments), and the concomitant down-regulation of antiapoptotic protein Bcl-2. Biosensor-based binding studies indicated that the ancillary ligands were critical in determining the DNA binding affinities, and competition binding experiments further characterized the nature of the interaction
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Ruthenium(II)–Arene RAPTA Type Complexes Containing Curcumin and Bisdemethoxycurcumin Display Potent and Selective Anticancer Activity
2015Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Giulio Lupidi, Rosario Scopelliti, Tina Riedel, Francesca Condello, Suman Mukhopadhyay, Paul J DysonAbstract:A series of novel ruthenium(II) arene RAPTA type derivatives (arene = cymene, Hexamethylbenzene) containing curcumin-based ligands (curcH = curcumin, bdcurcH = bisdemethoxycurcumin) and PTA (1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized. The solid-state structures of [Ru(cym)(curc)(PTA)][SO3CF3], [Ru(hmb)(curc)(PTA)][SO3CF3], and [Ru(hmb)(bdcurc)(PTA)][SO3CF3] have been determined by single-crystal X-ray diffraction. The antitumor activity of the complexes has been evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. The correlation of the cytotoxicity upon switching the curcumin-based ligands, i.e. curcumin vs bisdemethoxycurcumin, is not straightforward. In contrast, the PTA ligand greatly enhances the activity and selectivity of ruthenium compounds in comparison to previously reported compounds
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Ruthenium(II)–Arene RAPTA Type Complexes Containing Curcumin and Bisdemethoxycurcumin Display Potent and Selective Anticancer Activity
Organometallics, 2014Co-Authors: Riccardo Pettinari, Fabio Marchetti, Claudio Pettinari, Giulio Lupidi, Rosario Scopelliti, Tina Riedel, Francesca Condello, Suman Mukhopadhyay, Paul J DysonAbstract:A series of novel ruthenium(II) arene RAPTA type derivatives (arene = cymene, Hexamethylbenzene) containing curcumin-based ligands (curcH = curcumin, bdcurcH = bisdemethoxycurcumin) and PTA (1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized. The solid-state structures of [Ru(cym)(curc)(PTA)][SO3CF3], [Ru(hmb)(curc)(PTA)][SO3CF3], and [Ru(hmb)(bdcurc)(PTA)][SO3CF3] have been determined by single-crystal X-ray diffraction. The antitumor activity of the complexes has been evaluated in vitro against human ovarian carcinoma cells (A2780 and A2780cisR), as well as against nontumorous human embryonic kidney (HEK293) cells. The correlation of the cytotoxicity upon switching the curcumin-based ligands, i.e. curcumin vs bisdemethoxycurcumin, is not straightforward. In contrast, the PTA ligand greatly enhances the activity and selectivity of ruthenium compounds in comparison to previously reported compounds.