Synthesis, characterisation and cytotoxicity studies of ruthenium arene complexes bearing trichlorogermyl ligands

Deacon-Price, Connor; Romano, Dario; Riedel, Tina; Dyson, Paul J.; Blom, Burgert

doi:10.1016/j.ica.2018.09.019

Cited by 15 publications

(4 citation statements)

References 35 publications

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“…These results are good evidence of the influence of the triphenylphosphine ligand on cellular toxicity. The literature [20][21][22][23] cites many examples of Ru IIarene complexes, without phosphine, with very high IC 50 values in various tumorigenic cell lines. One of the causes that leads to low toxicity of these compounds is the lack of lipophilic groups, decreasing the cellular uptake of these complexes.…”

Section: Biological Anticancer Experimentsmentioning

confidence: 99%

“…However, the half maximal inhibitory concentration (IC 50 ) values in cancer cells for these compounds are generally high (> 100 μM), which is attributed to the high reactivity of these complexes, as a result of the low stability in organic solvents or under physiological conditions. [20][21][22][23] In addition, there are many papers 22,23 which currently report the use of monophosphines or monopyridines as the "X" ligand, resulting in complexes with high toxicity (< 5 μM), thanks to the lipophilicity enhancement of the compounds, when at least one of these molecules is present in their structures. Furthermore, when "L−L" is N−N, [24][25][26] P−P, [27][28][29][30][31][32] N−S, 33,34 N−O, 24,31,32 O−O 24,35,36 donor ligand, a wide range of IC 50 values is obtained.…”

Section: Introductionmentioning

confidence: 99%

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“Half-Sandwich”/RuII Anticancer Complexes Containing Triphenylphosphine and p-Substituted Benzoic Acids

Honorato¹,

Oliveira²,

Leite³

et al. 2020

J. Braz. Chem. Soc.

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Mononuclear and binuclear Ru II /arene/triphenylphosphine complexes with p-substituted benzoic acid derivatives were prepared and characterized. These monocationic complexes of type [Ru(η 6-p-cymene)(PPh 3)L] (L = benzoic acid (1), p-hydroxybenzoic acid (2), p-nitrobenzoic acid (3) and terephthalic acid (4)) were characterized using various techniques, such as nuclear magnetic resonance (NMR) and matrix-assisted laser desorption/ionization-time of flight (MALDI-TOF) mass spectrometry, and the crystal structure of 1, 3 and 4 were determined by X-ray diffraction analysis. The cytotoxicity of the complexes was evaluated, in vitro, against tumorigenic [MDA-MB-231, MCF-7 (breast), A549 (lung) and DU-145 (prostate)] and non-tumorigenic [MCF-10A (breast), MRC-5 (lung) and PNT-2 (prostate)] cells. The binuclear complex (4) was inactive due to its low solubility. Complexes 1, 2 and 3 showed similar cytotoxicity, however, complex 1 presented better selectivity index against MDA-MB-231 than compounds 2 and 3. Cellular ruthenium absorption was explored by inductively coupled plasma mass spectrometry (ICP-MS) analyzing the whole cells and the culture medium. Complementary studies showed that complex 1 inhibited colony formation, induced morphology changes in cells and promoted cell cycle arrest in the Sub-G1 phase for the MDA-MB-231 cells.

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Section: Biological Anticancer Experimentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“Half-Sandwich”/RuII Anticancer Complexes Containing Triphenylphosphine and p-Substituted Benzoic Acids

Honorato¹,

Oliveira²,

Leite³

et al. 2020

J. Braz. Chem. Soc.

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“…[(Dichlorido)(κN1-Benzimidazole)( η 6 -p-cymene)]ruthenium(II) [19] (109 mg, 260 µmol) was added to a solution of N -benzyl-1,3-dioxo-2,3-dihydro-1H-inden-2-carboxamide [25] (80 mg, 290 µmol) and sodium methanolate (20 mg, 315 µmol) in methanol (30 mL). The mixture was irradiated for 5 min at 50 °C.…”

Section: Methodsmentioning

confidence: 99%

“…Choosing pyridine as a N -donor adds the possibility of light activation, as utilized in photoactivated chemotherapy (PACT) [23,24]. Another approach is the exchange of the labile leaving group by trichlorogermyl, which also resulted in an increased stability and cytotoxicity [25].…”

Section: Introductionmentioning

confidence: 99%

Fine-Tuning the Activation Mode of an 1,3-Indandione-Based Ruthenium(II)-Cymene Half-Sandwich Complex by Variation of Its Leaving Group

et al. 2019

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Fine-tuning of the properties of a recently reported 1,3-indandione-based organoruthenium complex is attempted to optimize the stability under physiological conditions. Previous work has shown its capacity of inhibiting topoisomerase IIα; however, fast aquation leads to undesired reactions and ligand cleavage in the blood stream before the tumor tissue is reached. Exchange of the chlorido ligand for six different N-donor ligands resulted in new analogs that were stable at pH 7.4 and 8.5. Only a lowered pH level, as encountered in the extracellular space of the tumor tissue, was capable of aquating the complexes. The 50% inhibitory concentration (IC50) values in three human cancer cell lines differed only slightly, and their dependence on the utilized leaving group was smaller than what would be expected from their differences in cellular accumulation, but in accordance with the very minor variation revealed in measurements of the complexes’ lipophilicity.

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Transition Metal Complexes of Germanium

Osakada¹

2023

Organogermanium Compounds

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Synthesis, characterisation and cytotoxicity studies of ruthenium arene complexes bearing trichlorogermyl ligands

Cited by 15 publications

References 35 publications

“Half-Sandwich”/RuII Anticancer Complexes Containing Triphenylphosphine and p-Substituted Benzoic Acids

“Half-Sandwich”/RuII Anticancer Complexes Containing Triphenylphosphine and p-Substituted Benzoic Acids

Fine-Tuning the Activation Mode of an 1,3-Indandione-Based Ruthenium(II)-Cymene Half-Sandwich Complex by Variation of Its Leaving Group

Transition Metal Complexes of Germanium

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