Labile Pd-sulphur and Pt-sulphur bonds in organometallic palladium and platinum complexes [(COD)M(alkyl)(S-ligand)]n+—A speciation study

Lingen, Verena; Lüning, Anna; Krest, Alexander; Deacon, Glen B.; Schur, Julia; Ott, Ingo; Pantenburg, Ingo; Meyer, Gerd; Klein, Axel

doi:10.1016/j.jinorgbio.2016.06.009

Cited by 13 publications

(4 citation statements)

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“…In particular, a considerable effort is being devoted toward the development of organometallic compounds with antitumor activity. , The library of organometallic species with antiproliferative activities has seen marked growth in recent years with reports on organometallic compounds. − Among the transition metals, organometallic compounds of ruthenium ,− and gold , have been studied most extensively as antitumor agents. On the other hand, reports on Pt(II)-based organometallics in the same context are relatively less in number. − Most of the reported organoplatinum(II) compounds have an exchangeable and labile alkene ligand (1,5-cyclooctadiene) bound to the Pt(II) center. Additionally, there are some examples of cyclometalated organometallic complexes of Pt(II) that are reportedly biologically active and are potential anticancer agents …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Characterization, and Antiproliferative Activity of Organoplatinum Compounds Bearing a 1,2,3-Triazole Ring

et al. 2019

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Characterization, and Antiproliferative Activity of Organoplatinum Compounds Bearing a 1,2,3-Triazole Ring

et al. 2019

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“…(2) has approximate C 2 symmetry, which results in a signal for the olefinic proton and carbon atoms in 1 H and 13 C spectra, whereas [PtCl(sac)(COD)] (1) gives 2 signals in the NMR spectra for the corresponding groups due to the difference in the trans effects of the chlorido and sac ligands. The complexes exhibit high thermal stability in air.…”

Section: Discussionmentioning

confidence: 99%

“…Organoplatinum(II) complexes [Pt(R)(L)(COD)] (R = organic groups such as alkyl, aryl or alkynyl; L = other ligands) received great interest and were widely used in catalysis [6][7][8][9][10], material science [11,12] and medicinal research as anticancer agents [13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and crystal structures of platinum(II) saccharinate complexes with 1,5-cyclooctadiene

İçsel¹

2020

Turk J Chem

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Two new platinum(II) complexes, namely [PtCl(sac)(COD)] ( 1) and [Pt(sac) 2 (COD)] (2) (sac = saccharinate and COD = 1,5-cyclooctadiene), were synthesized and characterized by elemental analysis, IR, NMR, ESI-MS spectroscopic and thermal analysis (TG/DTA) methods. The platinum(II) complexes were prepared from the reaction of [PtCl 2 (COD)] with Na(sac)•2H 2 O. The addition of the sac ligand resulted in the replacement of 1 and 2 chlorido ligands in [PtCl 2 (COD)] to yield 1 and 2, respectively. The structures of the complexes were determined by single crystal X-ray diffraction and showed a distorted square planar coordination geometry around platinum(II). COD acted as a π -donor ligand, while sac was N -coordinated in both complexes. The TG/DTA data indicated that both complexes were thermally stable up to 220 °C in air and their thermal decompositions yielded Pt as a final product. Complexes 1 and 2 were also designed as possible precursors to synthesize new mixed-ligand platinum(II) sac complexes in a one-pot reaction.

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“…It should be also underlined that there is a limited number of studies on platinum organometallic compounds tested as antitumor drugs [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 ]. In this regard, the Zeise’s anion, [PtCl 3 (η 2 -C 2 H 4 )] − , showing an extreme lability of the trans to olefin chlorido ligand and a peculiar reactivity of the coordinated ethene, resulted to be a suitable precursor for the synthesis of new antitumor organometallic complexes [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of the Cytotoxic Activity of Water-Soluble Cationic Organometallic Complexes of the Type [Pt(η1-C2H4OMe)(L)(Phen)]+ (L = NH3, DMSO; Phen = 1,10-Phenanthroline)

Castro¹,

Stefàno²,

Migoni³

et al. 2021

Pharmaceutics

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Starting from the [PtCl(η1-C2H4OMe)(phen)] (phen = 1,10-phenanthroline, 1) platinum(II) precursor, we synthesized and characterized by multinuclear NMR new [Pt(η1-C2H4OMe)(L)(phen)]+ (L = NH3, 2; DMSO, 3) complexes. These organometallic species, potentially able to interact with cell membrane organic cation transporters (OCT), violating some of the classical rules for antitumor activity of cisplatin analogues, were evaluated for their cytotoxicity. Interestingly, despite both complexes 2 and 3 resulting in greater cell uptake than cisplatin in selected tumor cell lines, only 3 showed comparable or higher antitumor activity. General low cytotoxicity of complex 2 in the tested cell lines (SH-SY5Y, SK-OV-3, Hep-G2, Caco-2, HeLa, MCF-7, MG-63, ZL-65) appeared to depend on its stability towards solvolysis in neutral water, as assessed by NMR monitoring. Differently, the [Pt(η1-C2H4OMe)(DMSO)(phen)]+ (3) complex was easily hydrolyzed in neutral water, resulting in a comparable or higher cytotoxicity in cancer cells with respect to cisplatin. Further, both IC50 values and the uptake profiles of the active complex appeared quite different in the used cell lines, suggesting the occurrence of diversified biological effects. Nevertheless, further studies on the metabolism of complex 3 should be performed before planning its possible use in tissue- and tumor-specific drug design.

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Labile Pd-sulphur and Pt-sulphur bonds in organometallic palladium and platinum complexes [(COD)M(alkyl)(S-ligand)]n+—A speciation study

Cited by 13 publications

References 123 publications

Design, Synthesis, Characterization, and Antiproliferative Activity of Organoplatinum Compounds Bearing a 1,2,3-Triazole Ring

Design, Synthesis, Characterization, and Antiproliferative Activity of Organoplatinum Compounds Bearing a 1,2,3-Triazole Ring

Synthesis, characterization and crystal structures of platinum(II) saccharinate complexes with 1,5-cyclooctadiene

Synthesis and Evaluation of the Cytotoxic Activity of Water-Soluble Cationic Organometallic Complexes of the Type [Pt(η1-C2H4OMe)(L)(Phen)]+ (L = NH3, DMSO; Phen = 1,10-Phenanthroline)

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