Novel Pt(II) anticancer agents and their Pd(II) analogues: syntheses, crystal structures, reactions with nucleobases and cytotoxicities

Mock, Christian; Puscasu, Ina; Rauterkus, Michael J.; Tallen, Gesche; Wolff, Johannes; Krebs, Bernt

doi:10.1016/s0020-1693(01)00459-5

Cited by 77 publications

(40 citation statements)

References 19 publications

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“…As can be observed from the listed data in Table 3, the N-M(II) distances in these compounds are essentially the same and similar to other previously reported for dipyridine and pyridine complexes containing N-M bonds ( M= Pd, Pt). 2,4,11,14,22,23 The close similitude of the Pt-Cl and Pd-Cl bond distances in complexes 3 and 4 can be attributed to the lanthanide contraction effect present in the 5d platinum(II) cation. With regard to the conformational features displayed by the complexes 3 and 4 where sixmembered chelate rings were formed, the central ring in both complexes is in a boat conformation.…”

Section: X-ray Crystallographymentioning

confidence: 99%

“…[1][2][3][4][5][6] These compounds act as versatile ligands towards transition metals which yield five-and six-membered chelate rings in a bidentate coordination mode [7][8][9][10][11][12][13][14][15][16] Synthesis of compounds containing five-membered rings can be envisaged by the use of bipyridine (unbridged) derivatives (Ia, Figure 1). 7,8 When the dipyridinic ligands have flexible bridging groups as methylene, hydroxymethyl, amine, hydrazone and amide groups, they mainly form sixmembered rings (Ib).…”

Section: Introductionmentioning

confidence: 99%

“…7,8 When the dipyridinic ligands have flexible bridging groups as methylene, hydroxymethyl, amine, hydrazone and amide groups, they mainly form sixmembered rings (Ib). [9][10][11][12][13][14][15][16] In other dipyridines with less flexible bridging groups, the formation of five-membered rings (Ic) has been reported. 17,18 Recently, we described the synthesis of complexes of Li(I) 19 and Pd(II) 20 and the formation of five-membered rings by the use of the di- …”

Section: Introductionmentioning

confidence: 99%

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Synthesis and crystal structures of cis-palladium(II) and cis-platinum(II) complexes containing dipyridyl ligands

Andrade‐López¹,

Alvarado‐Rodríguez²,

González‐Montiel³

et al. 2007

Arkivoc

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Coordinative behavior of the di-(2-pyridyl)hydroxymethane (1) and di-(2-pyridyl)-2-pyridylsulfanylmethane (2) ligands towards Pd(II) and Pt(II) is described. The compounds 3-5 were characterized by IR, mass spectrometry and NMR spectroscopy. Crystal structures of [Pt{(C 5 H 4 N) 2 CH(OH)}Cl 2 ] 3 and [Pd{(C 5 H 4 N) 2 CH(2-C 5 H 4 NS)}Cl 2 ] 4 as DMSO solvates displayed the formation of neutral mononuclear complexes. In the complexes 3 and 4 is observed the formation of six-membered chelate rings. The local geometry of the metallic atoms can be described as square planar in the title complexes.

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Section: X-ray Crystallographymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and crystal structures of cis-palladium(II) and cis-platinum(II) complexes containing dipyridyl ligands

Andrade‐López¹,

Alvarado‐Rodríguez²,

González‐Montiel³

et al. 2007

Arkivoc

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“…DNA targeting moieties such as DNA intercalators used as platinum carriers may also be a new strategy, possibly leading to a broadened spectrum activity [4] and exalting platinum intracellular uptake. Pt(II) complexes with polypyridyl 2-(2-benzimidazolyl)pyridine ligands [5], heterocycles endowed with hydrophobic properties, have been reported and an increase of hydrophobicity around the drug-DNA binding site has been assessed. The presence of NH containing moieties in these complexes can originate H-bonding interactions towards DNA, validating the well-established structure-activity relationships which claims the necessity of at least one NH moiety within the ligand for H-bonding interactions towards DNA.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterisation and biological studies of new mononuclear platinum(II) complexes with sterically hindered heterocyclic ligands

Rubino

Portanova

Giammalva

et al. 2011

Inorganica Chimica Acta

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a b s t r a c tThree novel cisplatin analogues were synthesized, designed according to an approach which violates the ''classical'' structure-activity relationship, by replacing the diamine ligands with a planar N donor heterocycle giving a sterically hindered complex. Moreover, the sterical hindrance of antitumor drug candidates potentially makes them less susceptible to deactivation by sulphur-containing proteins and helping to overcome resistance mechanisms. The resulting mononuclear complexes of sterically hindered polidentate heterocyclic N ligands [PtCl(bbp)have been prepared and structurally characterised. Both neutral and ionic complexes are present, with monofunctional (1) and bifunctional Pt(II) moieties (2) and coordinatively saturated Pt(II) ions in the mixed ligand complex (3), whose size and shape enable them to behave as novel scaffolds for DNA binding. All complexes were tested ''in vitro'' for their biological activity on human HT29 colorectal carcinoma and HepG2 hepatoma cells. The complexes (1) and (3), endowed with a positive charge, showed a potent cytotoxic activity and reduced cell viability with an efficacy higher than that of cisplatin; whilst the neutral bifunctional compound (2) was inactive. IC50 values have been calculated for the active compounds. The cytotoxic effects were confirmed by the accumulation of treated cells in subG0/G1 phase of cell cycle, by the loss of mitochondrial potential (Dw m ) and by the chromatin condensation or fragmentation observed by means of fluorescence microscopy after Hoechst 33258 nuclear staining. A study on intracellular platinum uptake in HT29 cell line has been also performed and data obtained strongly suggest that the cytotoxicity of new tested complexes reported in this work is based on a different pharmacodynamic pattern with respect to cisplatin.

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“…(Jansen et al, 2002) Special attention in recent years were given to the investigation of dinuclear complexes of platinum and paladium. (Mock et al, 2001) …”

mentioning

confidence: 99%

Interactions of the Platinum(II) Complexes with Nitrogen- and Sulfur-Bonding Bio-Molecules in Chronic Lymphocytic Leukemia

Bogojeski¹,

Petrović²,

Bugarčić³

2012

Chronic Lymphocytic Leukemia

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Novel Pt(II) anticancer agents and their Pd(II) analogues: syntheses, crystal structures, reactions with nucleobases and cytotoxicities

Cited by 77 publications

References 19 publications

Synthesis and crystal structures of cis-palladium(II) and cis-platinum(II) complexes containing dipyridyl ligands

Synthesis and crystal structures of cis-palladium(II) and cis-platinum(II) complexes containing dipyridyl ligands

Synthesis, structural characterisation and biological studies of new mononuclear platinum(II) complexes with sterically hindered heterocyclic ligands

Interactions of the Platinum(II) Complexes with Nitrogen- and Sulfur-Bonding Bio-Molecules in Chronic Lymphocytic Leukemia

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