Synthesis, Structure, Protolytic Properties, Alkylating and Cytotoxic Activity of Novel Platinum(II) and Palladium(II) Complexes with Pyrazole‐Derived Ligands

Budzisz, Elżbieta; Małecka, Magdalena; Keppler, Bernhard K.; Arion, Vladimir B.; Andrijewski, Grzegorz; Krajewska, Urszula; Różalski, Marcin

doi:10.1002/ejic.200700139

Cited by 32 publications

(6 citation statements)

References 49 publications

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“…27). 145 A cisoidal arrangement of the pyrazole ligand was confirmed in the palladacyclic complexes by X-ray crystallographic analysis. The antiproliferative activity studies for complex 54 (and its platinum analogue) were performed on human acute leukaemia HL-60 and NALM-6 cancer cell lines with the commercial anticancer drugs cisplatin and carboplatin serving as reference standards.…”

Section: Nitrogen Based Multidentate Ligandsmentioning

confidence: 89%

Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes

2014

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Much success has been achieved with platinum-based chemotherapeutic agents, i.e. through interactions with DNA. The long-term application of Pt complexes is thwarted by issues, leading scientists to examine other metals such as palladium which could exhibit complementary modes of action (given emphasis wherever known). Over the last 10 years several research groups have focused on the application of an eclectic array of palladium complexes (of the type PdX2L2, palladacycles and related structures) as potential anti-cancer agents. This review therefore provides readers with an up to date account of the advances that have taken place over the past several decades.

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Section: Nitrogen Based Multidentate Ligandsmentioning

confidence: 89%

Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes

2014

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“…Recently, some attention has been focused on compounds with bulky planar ligands which are believed to be kinetically and thermodynamically more stable than simple analogs of cisplatin. 11 Most of the therapeutically investigated complexes are cis isomers although sometimes trans conformers also demonstrate high activity. 12 Noticeable cytotoxic activity, comparable to standard platinum-based anticancer agents, was exhibited by some planar trans aminepalladium(II) complexes i.e.…”

Section: Introductionmentioning

confidence: 99%

“…Pd(II) complexes with pyridine-type ligands, (e.g. pyrazole) 11 and some other complexes, for example with 2,6-dimethyl-4nitro-pyridine ligand, reveal better cytotoxic properties than cisplatin. 7 Coordination compounds of palladium(II) are model substrates for studies on crystal geometry of square planar complexes.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, a combination of pyridine derivatives with palladium to form Pd(II) complexes are supposed to have a large affinity for DNA binding sites. 11 Our studies have long been concerned with the structural effects of substrates on the yield of carbonylation of amines and nitrocompounds. [24][25][26][27][28] We described the substituent effects in the nitrobenzene and aniline ring on the yield of ethyl N-fenylcarbamate (EPC) in the carbonylation of a nitrobenzene (NB), mixture NB/AN or AN (where AN is aniline), respectively.…”

Section: Introductionmentioning

confidence: 99%

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Crystal structure, electronic properties and cytotoxic activity of palladium chloride complexes with monosubstituted pyridines

et al. 2012

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Palladium(II) complexes attract great attention due to their remarkable catalytic and biological activity. In the present study X-ray characterization, UV-Vis and Time-Dependent Density Functional Theory (TD-DFT) calculations for six PdCl(2)(XPy)(2) complexes (where: Py = pyridine; X = H, CH(3) or Cl) were applied in order to investigate substituent effects on their crystal structures and electronic properties and to combine the results with their catalytic and cytotoxic activity. The structures of complexes PdCl(2)(3-MePy)(2), PdCl(2)(4-MePy)(2) and PdCl(2)(2-ClPy)(2), have been described for the first time and we compared our results with available data for the whole series of six complexes. All compounds exhibit a square planar coordination geometry in which the palladium ion coordinates two nitrogen atoms of pyridine ligands and two chlorine atoms in trans positions. For complexes with ortho substituted XPy ligands a cis disposition of substituents takes place, whereas for other ligands: 3-MePy and 3-ClPy--the substituents are in trans positions. For XPy the energies of π-π* and n-π* transitions depend on the position and nature of the X substituent in the XPy ring. After complex formation a hipsochromic shift (24-34 nm) of π-π* and a bathochromic shift of n-π* bands are observed. The UV-Vis spectra of PdCl(2)(XPy)(2) confirm that square planar coordination geometry of complexes I-VI and two dπ-π* transitions are expected. With the help of the TD-DFT calculations we proved that dπ-π* transitions in solutions of PdCl(2)(XPy)(2) complexes result from MLCT (metal-to-ligand charge transfer) with contribution from chlorine atoms to palladium. We also studied substituent effects on cytotoxic properties of Pd(II) complexes against the human breast cancer cell line MCF7, the human prostate cancer cell line PC3, and the human T-cell lymphoblast-like cell line CCRF. The studied complexes were the most active against the CCRF cell line and less or even no cytotoxic effect was observed for PC3 cells. Complexes with MePy ligands showed increased cytotoxic activity compared to unsubstituted pyridine ligands.

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“…have shown the ability to coordinate acylpyrazolone ligands, [21] reports of Pt derivatives with 5-pyrazolones, to the best of our knowledge, have been rare. [22,23] Interestingly, these exotic β-diketonates have shown different coordination behaviours. As the enol tautomer, the HQ ligands are able to coordinate the metal through the two oxygen donors in a chelate form or through the pyrazole N2 atom, as observed in the crystal structures of [Ba(Q Ph ) 2 [25,26] These HQ ligands are also able to coordinate the metal through the pyrazole N2 atom, as observed in Ag I and Pb II complexes, where Q -showed a chelate tridentate structure, in which it coordinates two metal centres with the two oxygen atoms and the pyrazole N2 atom.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, and Biological Study of Pt^II Complexes with 4‐Acyl‐5‐pyrazolones

et al. 2014

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The syntheses of new PtII complexes with 4‐acyl‐5‐pyrazolones [HQPh = 1‐phenyl‐3‐methyl‐4‐benzoylpyrazol‐5‐one, a; HQpy,CF3 = 1‐(2‐pyridyl)‐3‐methyl‐trifluoroacetylpyrazol‐5‐one, b] are reported: trans‐[PtCl2(DMSO)(HQPh)] (1a), cis‐[PtCl2(DMSO)(HQPh)] (2a), [PtCl(DMSO)(Qpy,CF3)] (1b), and [PtCl2(KQpy,CF3)] (2b). All complexes were characterized by multinuclear (1H, 13C, 19F, and 195Pt), multidimensional NMR spectroscopy and single‐crystal X‐ray diffraction analyses. The isomer trans‐[PtCl2(DMSO)(HQPh)] (1a) crystallizes in two polymorphic forms, which correspond to two different conformers. In the trans–syn conformer (1aM) (monoclinic, space group P21/c), the H atom of the enol group [O(1)H(1)] establishes an intramolecular hydrogen bond with the ketone oxygen (O2), whereas in the trans–anti conformer (1aO) (orthorhombic, space group Pca21), the same groups are involved in an analogous intermolecular H bond. Interestingly, the cis isomer (2a) showed in solution and at room temperature slow rotation around both the Pt–N1 and the Pt–S bonds, which restrained both the acylpyrazolone and DMSO ligand motion. Moreover, the water solubility of the complexes trans‐ and cis‐[PtCl2(DMSO)(HQPh)] (1a and 2a) and [PtCl2(KQpy,CF3)] (2b) allowed to perform in vitro biological assays on platinum‐sensitive human endometrium (HeLa) and platinum‐resistant human breast (MCF‐7) cancer cell lines. It was also possible to compare their cytotoxicity to cisplatin. Interestingly, trans isomer 1a showed higher cytotoxicity on HeLa cells compared to the cis isomer 2a.

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Synthesis, Structure, Protolytic Properties, Alkylating and Cytotoxic Activity of Novel Platinum(II) and Palladium(II) Complexes with Pyrazole‐Derived Ligands

Cited by 32 publications

References 49 publications

Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes

Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes

Crystal structure, electronic properties and cytotoxic activity of palladium chloride complexes with monosubstituted pyridines

Synthesis, Crystal Structure, and Biological Study of Pt^II Complexes with 4‐Acyl‐5‐pyrazolones

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Synthesis, Structure, Protolytic Properties, Alkylating and Cytotoxic Activity of Novel Platinum(II) and Palladium(II) Complexes with Pyrazole‐Derived Ligands

Cited by 32 publications

References 49 publications

Anti-cancer palladium complexes: a focus on PdX2L2, palladacycles and related complexes

Anti-cancer palladium complexes: a focus on PdX2L2, palladacycles and related complexes

Crystal structure, electronic properties and cytotoxic activity of palladium chloride complexes with monosubstituted pyridines

Synthesis, Crystal Structure, and Biological Study of PtII Complexes with 4‐Acyl‐5‐pyrazolones

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Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes

Anti-cancer palladium complexes: a focus on PdX₂L₂, palladacycles and related complexes

Synthesis, Crystal Structure, and Biological Study of Pt^II Complexes with 4‐Acyl‐5‐pyrazolones