1. Novel Imino Thioether Complexes of Platinum(II): Synthesis, Structural Investigation, and Biological Activity
- Author
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Franco Benetollo, Silvia Mazzega Sbovata, Rino A. Michelin, Paolo Sgarbossa, Cristina Marzano, Roberta Bertani, Valentina Gandin, and Mirto Mozzon
- Subjects
Models, Molecular ,Organoplatinum Compounds ,Nitrile ,Ethanethiol ,Stereochemistry ,chemistry.chemical_element ,platinum(II) ,biological activity ,Antineoplastic Agents ,Sulfides ,Crystallography, X-Ray ,Inorganic Chemistry ,Synthesis ,Structure-Activity Relationship ,chemistry.chemical_compound ,CROSS-LINK ,Thioether ,secondary aliphatic amines ,Tumor Cells, Cultured ,Humans ,Physical and Theoretical Chemistry ,X ray structure ,potential antitumor drugs ,inhibitor valproic acid ,OVARIAN-CANCER CELLS ,IN-VITRO ,COORDINATED NITRILES ,AMIDINE COMPLEXES ,Pt(II) complexes ,Tetrahydrofuran ,Coordination geometry ,Dose-Response Relationship, Drug ,Molecular Structure ,Ligand ,imino thioether complexes ,Triple bond ,chemistry ,MCF-7 Cells ,Imines ,Drug Screening Assays, Antitumor ,Platinum - Abstract
The reactions of the nitrile complexes cis- and trans-[PtCl2(NCR)2] (R = Me, Et, CH2Ph, Ph) with an excess of ethanethiol, EtSH, in the presence of a catalytic amount of n-BuLi in tetrahydrofuran (THF), afforded in good yield the bis-imino thioether derivatives cis-[PtCl2{E-N(H)?C(SEt)R}2] (R = Me (1), Et (2), CH2Ph (3), Ph (4)) and trans-[PtCl2{E-N(H)?C(SEt)R}2] (R = Me (5), Et (6), CH2Ph (7), Ph (8)). The imino thioether ligands assumed the E configuration corresponding to a cis addition of the thiol to the nitrile triple bond. The spectroscopic properties of these complexes have been reported along with the molecular structures of 1, 2, and 7 as established by X-ray crystallography which indicated that these compounds exhibit square-planar coordination geometry around the platinum center. Four N-H···Cl intermolecular contacts (N-H···Cl ca. 2.5-2.7 Å) between each chlorine atom and the N-H proton of the imino thioether ligand gave rise to "dimers" Pt2Cl4L4 (L = imino thioether) formed by two PtCl2L2 units. The cytotoxic properties of these new platinum(II) complexes were evaluated against various human cancer cell lines. Among all derivatives, trans-[PtCl2{E-N(H)?C(SEt)CH2Ph}2] showed the greatest in vitro cytotoxic activity being able to decrease cancer cell viability roughly 3-fold more effectively than cisplatin.
- Published
- 2013
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