Biological activity of neutral and cationic iridium(III) complexes with κP and κP,κS coordinated Ph2PCH2S(O)xPh (x = 0–2) ligands

Ludwig, Gerd; Mijatović, Sanja; Ranđelović, Ivan; Bulatović, Mirna; Miljković, Djordje; Maksimović‐Ivanić, Danijela; Korb, Marcus; Lang, Heinrich; Steinborn, Dirk; Kaluđerović, Goran N.

doi:10.1016/j.ejmech.2013.08.025

Cited by 27 publications

(20 citation statements)

References 39 publications

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“…45 The ruthenium-pincer complexes 1a and 1b were synthesized following a literature protocol. 35 1 H, 13 C, and 31 P NMR spectra were recorded either on a Bruker ASCEND 600 operating at 600 MHz for 1 H, 150 MHz for 13 C, 564 MHz for 31 P or on a Bruker AVANCE 400 operating at 400 MHz for 1 H, 100 MHz for 13 C, 376 MHz for 31 P. The mass analysis was done using an Agilent Accurate-Mass Q-Toff ESI-MS 6520. Circular dichroism studies were done using a Jasco-1500 spectropolarimeter.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…It has been demonstrated that, while imine-ruthenium complexes are active toward cancer cells with high selectivity, , the introduction of PPh 3 groups is known to impart better properties . In addition, a majority of the six coordinate ruthenium complexes tested for anticancer activity is based on bidentate ligands of the type P,P, , P,O, , P,S, , C,N, NN, and N,O. , Considering the fact that tridentate pincer-metal complexes have enjoyed unparalleled success in catalysis owing to their enhanced stability and reactivity, it would be interesting to probe their anticancer activity in the presence of imine and PPh 3 groups.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of NNN Chiral Ruthenium Complexes and Their Cytotoxicity Studies

et al. 2021

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The synthesis and characterization of chiral pincer-ruthenium complexes of the type (R2NNN)RuCl2 (PPh3) (R = 3-methylbutyl and 3,3-dimethylbutyl) is reported here. The cytotoxicity studies of these complexes were studied and compared with the corresponding activity of achiral complexes. The cytotoxic effect of pincer-ruthenium complexes on human dermal fibroblasts and human tongue carcinoma cells assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay displayed an inhibition of normal and cancer cell growth in a dose-dependent manner. Intracellular reactive oxygen species (ROS) level measurement, lactate dehydrogenase assay, DNA fragmentation, and necrosis studies revealed that treatment with pincer-ruthenium complexes induced a redox imbalance in SAS cells by upregulating ROS generation and caused necrotic cell death by disrupting the cellular membrane integrity.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of NNN Chiral Ruthenium Complexes and Their Cytotoxicity Studies

et al. 2021

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“…Pt drugs have achieved great success in the field of cancer chemotherapy. − However, the side effect of these Pt drugs has led chemotherapy research toward alternate anticancer agents such as Ru, Rh, Ir, and Os complexes. − In particular, organometallic half-sandwich complexes of some platinum group metals (Ru, Rh, Ir, and Os) have received considerable attention due to their easy tunable structure, high potency toward cancer cells, and specific mechanism of actions (MoAs). − Generally, the central metals of these 18-electron complexes [(η 5 -Cp)/(η 6 -arene)M(XY)Cl] 0/+ (Cp = functionalized cyclopentadienyl; M = Ru, Rh, Ir, Os; XY = bidentate ligands) have adopted six-coordinated geometry, where the chlorine atom, the bidentate ligand XY, and η 5 -Cp/η 6 -arene occupy one coordination site, two coordination sites, and three coordination sites, respectively (Scheme , I ). It should be noted that hydrolysis of M–Cl bonds, i.e., Cl – /H 2 O exchange, usually represents an activation step for these 18-electron complexes, since M–H 2 O aqua were usually more reactive than the corresponding chloride analogues .…”

Section: Introductionmentioning

confidence: 99%

16-Electron Half-Sandwich Rhodium(III), Iridium(III), and Ruthenium(II) Complexes as Lysosome-Targeted Anticancer Agents

Gao

Guo

et al. 2021

Organometallics

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The 18-electron half-sandwich platinum group (Rh, Ru, Ir, and Os) metal anticancer complexes have been largely reported due to their easy tunable structure, high potency toward cancer cells, and specific mechanism of actions. However, the 16electron (without the leaving group Cl − ) half-sandwich complexes and their biological evaluation are rarely investigated. With an easy access to the required α-keto-β-diimine ligands using m-CPBA as oxidant, we herein reported the synthesis and characterization of a panel of structurally related 16-electron piano-stool rhodium, iridium, and ruthenium complexes through the rearranged coordination reaction. These complexes have been well-established by NMR spectroscopy, mass spectrometry, single-crystal X-ray crystallography, and elemental analysis. Each of these complexes was stable and exhibited fluorescence in solution. Although no reaction with nucleobase (9-EtG and 9-MeA) was observed, the representative Rh5 showed affinity toward CT-DNA. These 16electron complexes showed promising activity toward A549 and HeLa cancer cells with the values of IC 50 in the range 7.1−32.3 μM, which was comparable to or even better than cisplatin. In addition, the structure−activity relationships were observed that the change of the metal center from iridium(III) and ruthenium(II) to rhodium(III) could enhance the cytotoxicity of these unsaturated complexes. The investigation of mechanism of actions (MoAs) using flow cytometry displayed that the cytotoxicity of the complex Rh5 was associated with the perturbation of the cell cycle and the induction of cell apoptosis. Moreover, microscopic analysis by confocal microscopy suggested that the representative 16-electron complex Rh5 entered A549 cells via energy-dependent pathway and predominantly accumulated in lysosomes, thus resulting in the disruption of lysosomal integrity.

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“…The fact that compounds inhibited cell division and induced cell senescence in parallel with cell death deserves more comments. In fact, while the induction of apoptosis has been reported for diverse iridium complexes, to the best of our knowledge we describe here the first case clearly evidencing the ability of iridium complexes to initiate senescence [ 26 , 27 ]. In recent years, it has been established that senescence is a special form of durable cell cycle arrest, and might represent a primary mechanism for tumor prevention and suppression.…”

Section: Resultsmentioning

confidence: 69%

A Comparative Analysis of the In Vitro Anticancer Activity of Iridium(III) {η5-C5Me4R} Complexes with Variable R Groups

Palo

Drača

Murrali

et al. 2021

IJMS

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Piano-stool iridium complexes based on the pentamethylcyclopentadienyl ligand (Cp*) have been intensively investigated as anticancer drug candidates and hold much promise in this setting. A systematic study aimed at outlining the effect of Cp* mono-derivatization on the antiproliferative activity is presented here. Thus, the dinuclear complexes [Ir(η5-C5Me4R)Cl(μ-Cl)]2 (R = Me, 1a; R = H, 1b; R = Pr, 1c; R = 4-C6H4F, 1d; R = 4-C6H4OH, 1e), their 2-phenylpyridyl mononuclear derivatives [Ir(η5-C5Me4R)(kN,kCPhPy)Cl] (2a–d), and the dimethylsulfoxide complex [Ir{η5-C5Me4(4-C6H4OH)}Cl2(κS-Me2S=O)] (3) were synthesized, structurally characterized, and assessed for their cytotoxicity towards a panel of six human and rodent cancer cell lines (mouse melanoma, B16; rat glioma, C6; breast adenocarcinoma, MCF-7; colorectal carcinoma, SW620 and HCT116; ovarian carcinoma, A2780) and one primary, human fetal lung fibroblast cell line (MRC5). Complexes 2b (R = H) and 2d (4-C6H4F) emerged as the most active ones and were selected for further investigation. They did not affect the viability of primary mouse peritoneal cells, and their tumoricidal action arises from the combined influence on cellular proliferation, apoptosis and senescence. The latter is triggered by mitochondrial failure and production of reactive oxygen and nitrogen species.

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Biological activity of neutral and cationic iridium(III) complexes with κP and κP,κS coordinated Ph2PCH2S(O)xPh (x = 0–2) ligands

Cited by 27 publications

References 39 publications

Synthesis of NNN Chiral Ruthenium Complexes and Their Cytotoxicity Studies

Synthesis of NNN Chiral Ruthenium Complexes and Their Cytotoxicity Studies

16-Electron Half-Sandwich Rhodium(III), Iridium(III), and Ruthenium(II) Complexes as Lysosome-Targeted Anticancer Agents

A Comparative Analysis of the In Vitro Anticancer Activity of Iridium(III) {η5-C5Me4R} Complexes with Variable R Groups

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