Platinum(II) complexes with R2edda ligands (R = Me, Et, n-Pr; edda = ethylenediamine-N,N′-diacetate): Synthesis and characterization

Kaluđerović, Goran N.; Pantelić, Nebojša; Eichhorn, Thomas; Bette, Martin; Wagner, Christoph; Zmejkovski, Bojana B.; Schmidt, Harry

doi:10.1016/j.poly.2014.01.018

Cited by 9 publications

(2 citation statements)

References 17 publications

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“…From 2.60 to 3.00 ppm are chemical shifts for protons from ethylenediamine bridge, while signals attributable to protons (O)C–C H –NH are slightly shifted downfield (4.00–4.80 ppm) compared with free ligands. Signals of RC H 2 –OOC– protons were found at 3.60–4.00 ppm, similar to that of free ligands . Signals of N H protons in complexes are shifted downfield corresponding to free ligands, and appear at 6.40–7.50 ppm.…”

Section: Resultsmentioning

confidence: 80%

“…In the last decade, a number of these complexes were synthesized, using chelating ethylenediamine ligands derived from different amino acids and 1,2‐dibromethane, including Pt(IV) and Pt(II) complexes with ethylenediamine‐ N,N′ ‐diacetate ( edda )‐type ligands. These complexes showed antitumor activity equal to or better than cisplatin on a wide spectrum of tumor cell lines …”

Section: Introductionmentioning

confidence: 99%

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Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex

et al. 2017

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This study presents the synthesis, characterization, and antitumor action of five new Pt(II) halogenido, chlorido, and iodido complexes with edda type of ligands. (S,S)-Ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid dihydrochloride and its methyl, ethyl, and n-propyl esters were prepared according to the previously reported procedure. All investigated complexes were characterized by IR, ESI-MS ( H, C, and HMBC) NMR spectroscopy, and elemental analysis. Their cytotoxic action was investigated in four human tumor cell lines: promyelocytic (HL-60) and lymphocytic (REH) leukemia, glioma (U251), and lung carcinoma (H460). Cell viability was assessed by acid phosphatase and LDH assay, while oxidative stress and cell death parameters were analyzed by flow cytometry. The results showed that novel Pt(II) complexes exhibited antitumor action superior to precursor ligands, with iodido complexes being more efficient than corresponding chlorido complexes. Human promyelocytic cell line (HL-60) was the most sensitive to antitumor action of all investigated substances and was used for investigation of the underlying mode of antileukemic action. The investigated Pt(II) complexes showed more potent antileukemic action than corresponding Pt(IV) complex, through induction of oxidative stress and apoptosis, evidenced by caspase (8, 9, and 3) activation and phosphatidylserine externalization.

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Section: Resultsmentioning

confidence: 80%

Section: Introductionmentioning

confidence: 99%

Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex

et al. 2017

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Palladium(II) and Platinum(II) Complexes Containing Six‐Membered N‐Heterocyclic Ligands: Synthesis, Characterization, Interaction with DNA, DFT Calculation, and Cytotoxicity

et al. 2014

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Four novel complexes based on the ligand piperazine (Pip) in a chair conformation have been synthesized, namely [Pd(5,5Ј-dcbpy)Pip]·4H 2 O (1), [Pt(5,5Ј-dcbpy)Pip]·3H 2 O (2), [Pd(4,4Ј-dcbpy)Pip]·4H 2 O (3), and [Pt(4,4Ј-dcbpy)Pip]·2H 2 O (4; 4,4Ј-dcbpy = 2,2Ј-bipyridyl-4,4Ј-dicarboxylate, 5,5Ј-dcbpy = 2,2Ј-bipyridyl-5,5Ј-dicarboxylate). The four complexes were characterized by elemental analysis, FTIR spectroscopy, 1 H and 13 C NMR spectroscopy, and single-crystal X-ray diffraction analysis. In addition, gel electrophoresis was per- [a]5741 formed on the four complexes and further insight into these complexes was gained by quantum chemistry calculations. The interaction of these complexes with fish sperm DNA (FS-DNA) was studied by UV/Vis and fluorescence spectroscopy, which revealed that they have the ability to bind to FS-DNA. The IC 50 values of the four complexes range from 8.3 to 32.5 μM. Finally, we studied the cytotoxic activities of complexes 1-4 against two different cancer cell lines.devoted to the design and synthesis of new platinum anticancer drugs and their clinical trials for the cure of cancer. [2] Moreover, other transition-metal complexes, such as Pd 2+ , Ru 2+ , Ru 3+ , Fe 2+ , Co 2+ , Ni 2+ , Cu 2+ , and Zn 2+ have been designed and extensively investigated for their biological activity. [3] It is noteworthy that among transition-metal complexes of biological relevance, a broad range of parent Pd II /Pt II compounds bearing a variety of N-containing ligands have been extensively explored for their antitumor activity. Both Pd II and Pt II are soft Lewis acids and give rise to stronger bonds with nitrogen donors (soft bases) than oxygen donors (hard bases). From a kinetic and mechanistic point of view, the mechanism of action of platinum(II) anticancer drugs as well as of their palladium(II) analogues are suitable models for future drugs, because they exhibit around 10 4 -10 5 times higher activity than many related compounds; from a structural point of view, their structures and equilibrium behavior are similar. [4] As a consequence, numerous pairs of palladium and platinum complexes have been widely studied as anticancer drugs. [5] Of these, squareplanar platinum(II)/palladium(II) coordination complexes of diimine ligands have attracted considerable attention and interest due to their unique luminescent properties, [6] which may be exploited in chemosensing [7] and photocatalysis [8] as well as for their pronounced biological activity. [5a,9] Specifically, dipyridyl and its derivatives can form square-planar coordination complexes with platinum(II)/palladium(II). www.eurjic.org FULL PAPER Scheme 1. Synthesis of Pt/Pd complexes 1-4.On the other hand, piperazine is a good hydrogen-bond acceptor, which is beneficial for the coordination of metal ions to form supramolecular assemblies that are interesting building blocks with chair or boat conformations. [10] It is noteworthy that piperazine shows little toxicity and, consequently, it is widely used in medicine, [11] for example, in the prepara...

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Palladium(II) complexes: Structure, development and cytotoxicity from cisplatin analogues to chelating ligands with N stereocenters

Zmejkovski

Pantelić

Kaluđerović

2022

Inorganica Chimica Acta

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Platinum(II) complexes with R2edda ligands (R = Me, Et, n-Pr; edda = ethylenediamine-N,N′-diacetate): Synthesis and characterization

Cited by 9 publications

References 17 publications

Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex

Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex

Palladium(II) and Platinum(II) Complexes Containing Six‐Membered N‐Heterocyclic Ligands: Synthesis, Characterization, Interaction with DNA, DFT Calculation, and Cytotoxicity

Palladium(II) complexes: Structure, development and cytotoxicity from cisplatin analogues to chelating ligands with N stereocenters

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