α-Diimines as Versatile, Derivatizable Ligands in Ruthenium(II) p-Cymene Anticancer Complexes
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Biancalana, Lorenzo
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Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Biancalana, Lorenzo
[1
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Batchelor, Lucinda K.
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Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, CH-1015 Lausanne, SwitzerlandUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Batchelor, Lucinda K.
[2
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Funaioli, Tiziana
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Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Funaioli, Tiziana
[1
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Zacchini, Stefano
[3
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Bortoluzzi, Marco
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Univ Ca Foscari Venezia, Dipartirnento Sci Mol & Nanosistemi, Via Torino 155, I-30170 Venice, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Bortoluzzi, Marco
[4
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Pampaloni, Guido
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Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Pampaloni, Guido
[1
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Dyson, Paul J.
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Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, CH-1015 Lausanne, SwitzerlandUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Dyson, Paul J.
[2
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Marchetti, Fabio
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Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Marchetti, Fabio
[1
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机构:
[1] Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
alpha-Diimines are among the most robust and versatile ligands available in synthetic coordination chemistry, possessing finely tunable steric and electronic properties. A series of novel cationic ruthenium(II) p-cymene complexes bearing simple a-diimine ligands, [(eta(6)-p-cymene)RuCl{kappa N-2-(HCNR)(2)}]NO3 (R = Cy, [1]NO3; R = 4-C6H10OH, [2]NO3; R = 4-C6H4OH, [3]NO3), were prepared in near-quantitative yields as their nitrate salts. [2]NO3 displays high water solubility. The potential of the a-diimine ligand in [3]NO3 as a carrier of bioactive molecules was investigated via esterification reactions with the hydroxyl groups. Thus, the double-functionalized derivatives [(eta(6)-p-cymene)RuCl{kappa N-2-(HCN(4-C6H4OCO-R))(2})]NO3 (R = aspirinate, [5]NO3; valproate, [6]NO3) and also [4]Cl (R = Me) were obtained in good-to-high yields. UV-vis and multinuclear NMR spectroscopy and cyclic voltammetric studies in aqueous solution revealed only minor ruthenium chloride hydrolytic cleavage, biologically accessible reduction potentials, and pH-dependent behavior of [3]NO3. Density functional theory analysis was performed in order to compare the Ru-Cl bond strength in [1](+) with the analogous ethylenediamine complex, showing that the higher stability observed in the former is related to the electron-withdrawing properties of the adiimine ligand. In vitro cytotoxicity studies were performed against tumorigenic (A2780 and A2780cisR) and nontumorigenic (HEK-293) cell lines, with the complexes bearing simple a-diimine ligands ranging from inactive to IC50 values in the low micromolar range. The complexes functionalized with bioactive components, i.e., [5]NO3 and [6]NO3, exhibited a marked increase in the cytotoxicity with respect to the precursor [3]NO3.
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Qufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Qufu Normal Univ, Dept Chem & Chem Engn, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R ChinaQufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Yang, Yuliang
Guo, Lihua
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Qufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Qufu Normal Univ, Dept Chem & Chem Engn, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R ChinaQufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Guo, Lihua
Tian, Zhenzhen
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Qufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Qufu Normal Univ, Dept Chem & Chem Engn, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R ChinaQufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Tian, Zhenzhen
Liu, Xicheng
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Qufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Qufu Normal Univ, Dept Chem & Chem Engn, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R ChinaQufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Liu, Xicheng
Gong, Yuteng
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Qufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Qufu Normal Univ, Dept Chem & Chem Engn, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R ChinaQufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Gong, Yuteng
Zheng, Hongmei
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Qufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Qufu Normal Univ, Dept Chem & Chem Engn, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R ChinaQufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Zheng, Hongmei
Ge, Xingxing
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Qufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Qufu Normal Univ, Dept Chem & Chem Engn, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R ChinaQufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Ge, Xingxing
Liu, Zhe
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Qufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
Qufu Normal Univ, Dept Chem & Chem Engn, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R ChinaQufu Normal Univ, Inst Anticanc Agents Dev & Theranost Applicat, Key Lab Life Organ Anal, Qufu 273165, Peoples R China
机构:
Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Biancalana, Lorenzo
Batchelor, Lucinda K.
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机构:
Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, CH-1015 Lausanne, SwitzerlandUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Batchelor, Lucinda K.
Ciancaleoni, Gianluca
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Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Ciancaleoni, Gianluca
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Zacchini, Stefano
Pampaloni, Guido
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Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Pampaloni, Guido
Dyson, Paul J.
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机构:
Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, CH-1015 Lausanne, SwitzerlandUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy
Dyson, Paul J.
Marchetti, Fabio
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机构:
Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, ItalyUniv Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy