Novel platinum(II) compounds with O,S bidentate ligands: synthesis, characterization, antiproliferative properties and biomolecular interactions

Carolin Mügge; Ruiqi Liu; Helmar G?rlsChiara GabbianiElena MichelucciNadine RüdigerJoachim H. ClementLuigi MessoriWolfgang Weigand

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Novel platinum(II) compounds with O,S bidentate ligands: synthesis, characterization, antiproliferative properties and biomolecular interactions

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Cisplatin and its analogues are first-line chemotherapeutic agents for the treatment of numerous human cancers. A major inconvenience in their clinical use is their strong tendency to link to sulfur compounds, especially in kidney, ultimately leading to severe nephrotoxicity. To overcome this drawback we prepared a variety of platinum complexes with sulfur ligands and analyzed their biological profiles. Here, a series of six platinum(II) compounds bearing a conserved O,S binding moiety have been synthesized and characterized as experimental anticancer agents. The six compounds differ in the nature of the O,S bidentate β-hydroxydithiocinnamic alkyl ester ligand where both the substituents on the aromatic ring and the length of the alkyl chain may be varied. The two remaining coordination positions at the square-planar platinum(II) center are occupied by a chloride ion and a DMSO molecule. These novel platinum compounds showed an acceptable solubility profile in mixed DMSO-buffer solutions and an appreciable stability at physiological pH as judged from analysis of their time-course UV-visible absorption spectra. Their anti-proliferative and pro-apoptotic activities were tested against the cisplatin-resistant lung cancer cell line A549. Assays revealed significant effects of the sample drugs at low concentrations (in the μmolar range); initial structure-activity-relationships are proposed. The activity of the apoptosis-promoting protein caspase 3/7 was determined; results proved that these novel platinum compounds, under the chosen experimental conditions, preferentially induce apoptosis over necrosis. Reactions with the model proteins cytochrome c, lysozyme and albumin were studied by ESI MS and ICP-OES to gain preliminary mechanistic information. The tested compounds turned out to metalate the mentioned proteins to a large extent. In view of the obtained results these novel platinum complexes qualify themselves as promising cytotoxic agents and merit, in our opinion, a deeper pharmacological evaluation as prospective anticancer agents.

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《Dalton transactions: An international journal of inorganic chemistry》 |2014年第8期|3072-3086|共15页
作者
Carolin Mügge; Ruiqi Liu; Helmar G?rlsChiara GabbianiElena MichelucciNadine RüdigerJoachim H. ClementLuigi MessoriWolfgang Weigand;
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作者单位

Institute of Inorganic and Analytical Chemistry, Friedrich-Schiller-University Jena, Humboldtstra?e 8, 07743 Jena, Germany;

Department of Chemistry and Industrial Chemistry, University of Pisa, Via Risorgimento 35, 56126 Pisa, Italy;

Mass Spectrometry Center (CISM), University of Florence, Via U. Schiff 6, 50019 Sesto Fiorentino, Firenze, ItalyDepartment of Internal Medicine II, Jena University Hospital, Erlanger Allee 101, 07740 Jena, GermanyLaboratory of Metals in Medicine, Department of Chemistry, University of Florence, Via della Lastruccia 3, 50019 Sesto Fiorentino, Firenze, Italy;

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正文语种英语
中图分类化学;无机化学;
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Novel; platinum(II); interactions;

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Novel platinum(II) compounds with O,S bidentate ligands: synthesis, characterization, antiproliferative properties and biomolecular interactions

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