Synthesis, spectroscopic characterization and biological activity of cis-[Ru(hesperidin)(1,10′-phenanthroline)2](PF6) complex

Oliveira, Regina Maria Mendes; Daniel, Juliana Feijó de Souza; Carlos, Rose Maria

doi:10.1016/j.molstruc.2012.09.066

Cited by 14 publications

(4 citation statements)

References 36 publications

(33 reference statements)

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“…The RCX was synthesized by reacting a previously deprotonated xanthoxylin with the precursor complex [Ru(phen) 2 Cl 2 ] in an ethanol/water mixture using a procedure similar to one already established 16 , 17 (Fig. 1 ).…”

Section: Resultsmentioning

confidence: 99%

A novel ruthenium complex with xanthoxylin induces S-phase arrest and causes ERK1/2-mediated apoptosis in HepG2 cells through a p53-independent pathway

et al. 2018

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Ruthenium-based compounds have gained great interest due to their potent cytotoxicity in cancer cells; however, much of their potential applications remain unexplored. In this paper, we report the synthesis of a novel ruthenium complex with xanthoxylin (RCX) and the investigation of its cellular and molecular action in human hepatocellular carcinoma HepG2 cells. We found that RCX exhibited a potent cytotoxic effect in a panel of cancer cell lines in monolayer cultures and in a 3D model of multicellular cancer spheroids formed from HepG2 cells. This compound is detected at a high concentration in the cell nuclei, induces DNA intercalation and inhibits DNA synthesis, arresting the cell cycle in the S-phase, which is followed by the activation of the caspase-mediated apoptosis pathway in HepG2 cells. Gene expression analysis revealed changes in the expression of genes related to cell cycle control, apoptosis and the MAPK pathway. In addition, RCX induced the phosphorylation of ERK1/2, and pretreatment with U-0126, an MEK inhibitor known to inhibit the activation of ERK1/2, prevented RCX-induced apoptosis. In contrast, pretreatment with a p53 inhibitor (cyclic pifithrin-α) did not prevent RCX-induced apoptosis, indicating the activation of a p53-independent apoptosis pathway. RCX also presented a potent in vivo antitumor effect in C.B-17 SCID mice engrafted with HepG2 cells. Altogether, these results indicate that RCX is a novel anticancer drug candidate.

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Section: Resultsmentioning

confidence: 99%

A novel ruthenium complex with xanthoxylin induces S-phase arrest and causes ERK1/2-mediated apoptosis in HepG2 cells through a p53-independent pathway

et al. 2018

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“…Most Ru(II) complexes induce cancer cell death in the single-digit micromolar range, similar to cisplatin. Ru(II) polypyridyl complexes with different types of dioxo ligands have shown promise as potential anticancer agents. − Among those Ru(II) polypyridyl complexes, analogues with acetylacetonate-based ligands have been particularly active. Ru(II) complexes with the general formula [Ru(bpy) 2 (L)] + , where bpy = 2,2′-bipyridine and L is a diverse array of κ 2 -O-O′ chelating β-diketone ligands including acetylacetonate (acac), showed nanomolar potency against DU-145 cells (human prostate cancer) and MIA PaCa-2 cells (human pancreatic cancer) …”

Section: Introductionmentioning

confidence: 99%

Ru(II)-Based Acetylacetonate Complexes Induce Apoptosis Selectively in Cancer Cells

et al. 2021

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The synthesis, chemical and biological characterization of seven Ru(II) polypyridyl complexes containing acetylacetonate (acac) ligands are reported. Electronic absorption spectra were determined and electrochemical potentials consistent with Ru(III/II) couples ranging from +0.60 to +0.73 V vs Ag/AgCl were measured. A series of complexes were screened against MDA-MB-231, DU-145, and MCF-10A cell lines to evaluate their cytotoxicities in cancer and normal cell lines. Although most complexes were either nontoxic or equipotent in cancer cells and normal cell lines, compound 1, [Ru(dpqy)(acac)(py)](PF6), where dqpy is 2,6-di(quinolin-2-yl)pyridine, showed up to 2.5:1.0 selectivity for cancer as compared to normal cells, along with nanomolar EC50 values in MDA-MB-231 cells. Lipophilicity, determined as the octanol/water partition coefficient, log P o/w, ranged from −0.33 (0.06) to 1.15 (0.10) for the complexes. Although cytotoxicity was not correlated with electrochemical potentials, a moderate linear correlation between lipophilicity and toxicities was observed. Cell death mechanism studies indicated that several of the Ru–acac compounds, including 1, induce apoptosis in MDA-MB-231 cells.

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“…Our research group developed a methodological characterization for this class of Mg( ii ) complexes bearing phen and natural products as ligands in previous studies. 29,30 However, the most prominent difference between the Mg(phen)(fer) complex prepared in this study and other Mg-phenol complexes is that, at room temperature, the equilibrium process between the Mg(phen)(fer) structures indicates that the hexacoordinated structure is the most favoured according to H 1 -NMR, DOSY-NMR and mass spectrum experiments (Fig. S1–S4†).…”

Section: Resultsmentioning

confidence: 74%

Antioxidant activity of an Mg(ii) compound containing ferulic acid as a chelator: potential application for active packaging and riboflavin stabilisation

Marchi,

Kock,

Soares dos Campos

et al. 2024

Food Funct.

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Synthesis, spectroscopic characterization and biological activity of cis-[Ru(hesperidin)(1,10′-phenanthroline)2](PF6) complex

Cited by 14 publications

References 36 publications

A novel ruthenium complex with xanthoxylin induces S-phase arrest and causes ERK1/2-mediated apoptosis in HepG2 cells through a p53-independent pathway

A novel ruthenium complex with xanthoxylin induces S-phase arrest and causes ERK1/2-mediated apoptosis in HepG2 cells through a p53-independent pathway

Ru(II)-Based Acetylacetonate Complexes Induce Apoptosis Selectively in Cancer Cells

Antioxidant activity of an Mg(ii) compound containing ferulic acid as a chelator: potential application for active packaging and riboflavin stabilisation

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