Novel Homoleptic and Heteroleptic Pt(II) β‐oxodithiocinnamic ester Complexes: Synthesis, Characterization, Interactions with 9‐methylguanine and Antiproliferative Activity

GND
1258207036
ORCID
0000-0003-3669-9127
Affiliation
Institut für Anorganische und Analytische Chemie Friedrich-Schiller-Universität Humboldtstraße 8 07743 Jena Germany
Farh, Micheal K.;
GND
136906303
ORCID
0000-0002-7012-483X
Affiliation
Department of Gynecology Jena University Hospital – Friedrich Schiller University Jena Am Klinikum 1 07747 Jena Germany
Häfner, Norman;
GND
1214845193
Affiliation
Institut für Anorganische und Analytische Chemie Friedrich-Schiller-Universität Humboldtstraße 8 07743 Jena Germany
Görls, Helmar;
GND
1111567727
Affiliation
Department of Gynecology Jena University Hospital – Friedrich Schiller University Jena Am Klinikum 1 07747 Jena Germany
Runnebaum, Ingo B.;
GND
1062586395
ORCID
0000-0001-5177-1006
Affiliation
Institut für Anorganische und Analytische Chemie Friedrich-Schiller-Universität Humboldtstraße 8 07743 Jena Germany
Weigand, Wolfgang

Abstract Three new series of homoleptic and heteroleptic platinum(II) β‐oxodithiocinnamic ester complexes, [Pt(L1–L9) 2 ], [Pt(L1–L9)(DMS)Cl] and [Pt(L1–L9)(DMSO)Cl], were synthesized and characterized using elemental analysis, mass spectrometry, and different NMR spectroscopy ( 1 H, 13 C{ 1 H} and 195 Pt). The β‐oxodithiocinnamic esters coordinate towards the platinum(II) centre as O,S‐bidentate chelating ligands. The structures of HL3, [Pt(L2) 2 ], [Pt(L6)(DMS)Cl] as well as [Pt(L2)(DMSO)Cl] have been confirmed through the X‐ray crystallography, where the platinum(II) complexes exhibit a slightly distorted square planar geometry. In this article, we also investigated the solvolysis of three representative Pt(II) complexes, as well as the interaction with 9‐methylguanine as a DNA model system, by utilizing the LC‐ESI‐MS technique. A selection of the complexes was assessed for their use as anticancer agents, and cytotoxicity assays with these complexes showed modest toxicity on both Cisplatin sensitive and resistant ovarian cancer cell lines. However, the compounds cytotoxicity was not affected by the Cisplatin resistance mechanisms and a specific selection of the ligands may modify the cell line specificity.

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