846550-68-3Relevant academic research and scientific papers
Influence of PPh3 moiety in the anticancer activity of new organometallic ruthenium complexes
Sáez, Rubén,Lorenzo, Julia,Prieto, Ma Jose,Font-Bardia, Mercè,Calvet, Teresa,Ome?aca, Nuria,Vilaseca, Marta,Moreno, Virtudes
, p. 1 - 12 (2014)
The effect of the PPh3 group in the antitumor activity of some new organometallic ruthenium(II) complexes has been investigated. Several complexes of the type [Ru(II)(Cl)(PPh3)(Lig-N)], [Ru (II)(Cl)2(Lig-N)] (where Lig-N = pyridine derivate) and [Ru(II)(Cl)(PPh3)2], have been synthesized and characterized. A noticeable increment of the antitumor activity and cytotoxicity of the complexes due to the presence of PPh3 moiety has also been demonstrated, affording IC50 values of 5.2 μM in HL-60 tumor cell lines. Atomic force microscopy, circular dichroism and electrophoresis experiments have proved that these complexes can bind DNA resulting in a distortion of both secondary and tertiary structures. Ethidium bromide displacement fluorescence spectroscopy studies and viscosity measurements support that the presence of PPh3 group induces intercalation interactions with DNA. Indeed, crystallographic analysis, suggest that intra-molecular π-π interactions could be involved in the intercalation within DNA base pairs. Furthermore, high performance liquid chromatography mass spectrometry (HPLC-MS) studies have confirmed a strong interaction between ruthenium complexes and proteins (ubiquitin and potato carboxypeptidase inhibitor - PCI) including slower kinetics due to the presence of PPh 3 moiety, which could have an important role in detoxification mechanism and others. Finally, ion mobility mass spectrometry (IMMS) experiments have proved that there is no significant change in the gas phase structural conformation of the proteins owing to their bonding to ruthenium complexes.
Somatostatin subtype-2 receptor-targeted metal-based anticancer complexes
Barragán, Flavia,Carrion-Salip, Dolors,Gómez-Pinto, Irene,González-Cantó, Alejandro,Sadler, Peter J.,De Llorens, Rafael,Moreno, Virtudes,González, Carlos,Massaguer, Anna,Marchán, Vicente
, p. 1838 - 1855 (2012/11/13)
Conjugates of a dicarba analogue of octreotide, a potent somatostatin agonist whose receptors are overexpressed on tumor cells, with [PtCl 2(dap)] (dap = 1-(carboxylic acid)-1,2-diaminoethane) (3), [(η6-bip)Os(4-CO2-pico)Cl] (bip = biphenyl, pico = picolinate) (4), [(η6-p-cym)RuCl(dap)]+ (p-cym = p-cymene) (5), and [(η6-p-cym)RuCl(imidazole-CO 2H)(PPh3)]+ (6), were synthesized by using a solid-phase approach. Conjugates 3-5 readily underwent hydrolysis and DNA binding, whereas conjugate 6 was inert to ligand substitution. NMR spectroscopy and molecular dynamics calculations showed that conjugate formation does not perturb the overall peptide structure. Only 6 exhibited antiproliferative activity in human tumor cells (IC50 = 63 ± 2 μ in MCF-7 cells and IC50 = 26 ± 3 μ in DU-145 cells) with active participation of somatostatin receptors in cellular uptake. Similar cytotoxic activity was found in a normal cell line (IC50 = 45 ± 2.6 μ in CHO cells), which can be attributed to a similar level of expression of somatostatin subtype-2 receptor. These studies provide new insights into the effect of receptor-binding peptide conjugation on the activity of metal-based anticancer drugs, and demonstrate the potential of such hybrid compounds to target tumor cells specifically.
Catalytic activity of bis-phosphine ruthenium(ii)-arene compounds: Structure - Activity correlations
Chaplin, Adrian B.,Dyson, Paul J.
, p. 2447 - 2455 (2008/10/09)
The phosphine dissociation characteristics of a range of bis-phosphine ruthenium(II)-arene complexes, [Ru(PPh3)(PR3) (η6-arene)]PF6 (arene = p-cymene: PR3 = PPhMe2, PPh3, P(p-tol)3, PPh2 iPr; arene = PhMe: PR3 = PPhMe2, PPh 3), [Ru(PPh3)(η2-PPh2(C 6H4O))(η6-p-cymene)]PF6, and [RuCl(PPh3)(η7PPh2(CH2) 3Ph)]PF6, have been investigated by a combination of ligand exchange kinetics (with P(p-tol)3 in THF) and tandem electrospray ionization mass spectrometry (ESI-MS/MS). Trends in reactivity established from these studies were rationalized in terms of steric bulk, on the arene or phosphine, and conformational freedom of the phosphine ligands. A good correlation is found between these trends, especially from the ESI-MS/MS data, and activity of the complexes as catalyst precursors for the hydrogenation of styrene to ethyl benzene (in THF). The most active catalyst precursors show good activity under comparatively mild conditions (e.g., TOF ≥ 2000 h -1 for styrene hydrogenation in THF at 50 °C under 50 bar of H2). The X-ray structures of [RuCl(PPh3)(PPhMe 2)(η6-p-cymene)]PF6, [RuCl(PPh 3)(PPh2iPr)(η6-p-cymene)]PF 6, [RuCl(PPh3)(P(p-tol)3)(η6-p- cymene)]PF6, and [RuCl(η2-PPh2(C 6H4O))(η6-p-cymene)] are also reported.
