Cytotoxic organometallic [Ru(η6-anethole)(en)(X)]PF6 (X = Br or I) complexes: Synthesis, characterization and in vitro biological evaluation

Astudillo, David; Galdámez, Antonio; Sanguinetti, Maritza E.; Villena, Joan; Thomet, Franz A.

doi:10.1016/j.inoche.2017.08.024

Cited by 7 publications

(3 citation statements)

References 19 publications

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“…The interesting cytotoxic effect of 6f can probably be attributed to the Br in position 1 (R1) and/or Cl in position 2 (R2). These results are in agreement with data demonstrating that compounds substituted with this radical are relatively potent as cytotoxic agents . Finally, these compounds may be used as anticancer agents.…”

Section: Discussionsupporting

confidence: 91%

Cytotoxicity of new pyridazin‐3(2H)‐one derivatives orchestrating oxidative stress in human triple‐negative breast cancer (MDA‐MB‐468)

Bouchmaa

Mrid²,

Boukharsa

et al. 2018

Archiv der Pharmazie

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Triple-negative breast cancer (TNBC) is a complex and aggressive subtype of breast cancer characterized by high morbidity and mortality. In the absence of targeted therapy, only chemotherapy is available in this case of cancer. The current study investigated the antitumor effect of new pyridazin-3(2H)-one derivatives on the human TNBC cell line, MD-MB-468. The in vitro cytotoxic activities were investigated using the tetrazolium-based MTT assay. Lipid peroxidation, H 2 O 2 content, and the specific activities of antioxidant enzymes were also determined. Two molecules, 6f and 7h, were found to be selectively highly active against tumor cells with IC 50 values of 3.12 and 4.9 µM, respectively. Furthermore, cells exposed to 6f showed a significant increase in H 2 O 2 and lipid peroxidation levels, accompanied by a decrease in the enzyme activities of glutathione reductase (GR) and thioredoxin reductase (TrxR). The cytotoxicity of the compound 6f may improve the therapeutic efficacy of the current treatment for TNBC via the inhibition of GR and TrxR activities.anticancer agent, cytotoxicity, oxidative stress, pyridazin-(2H)-3-ones, triple-negative breast cancer

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Section: Discussionsupporting

confidence: 91%

Cytotoxicity of new pyridazin‐3(2H)‐one derivatives orchestrating oxidative stress in human triple‐negative breast cancer (MDA‐MB‐468)

Bouchmaa

Mrid²,

Boukharsa

et al. 2018

Archiv der Pharmazie

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“…2-(2,4-di-fluorophenyl) imidazole[4,5 f ][ 1 , 10 ]-phenanthroline was prepared using the method described above, but with 2,4-difluorobenzaldehyde (320 mg, 2.25 mmol). ESI-MS (in CH 3 CH 2 OH, m / z ):332.9 [M + H] + , 354.9 [M + Na] + , 687.0 [2M + Na] 2+ .…”

Section: Methodsmentioning

confidence: 99%

“…The arene Ru(II) complex [( η 6 -arene)Ru(X)(Y)(Z)] (XY is N,N-, N,O-, O,O- or S,O- chelating ligand, Z is a monoanionic ligand) has a high cytotoxicity in vivo and inhibits tumor cell growth [ 9 ]. The arene ligands are strongly coordinated with ruthenium; they stabilize the ruthenium in the oxidation state +2 and provide a hydrophobic side for passive transport through the cell membrane, and the chelating ligand and the leaving group (Cl) regulate the reactivity of the complex, resulting in cytotoxicity [ 10 , 11 ]. We have reported that arene Ru(II) complexes coordinated by phenanthroimidazole derivatives can inhibit tumor cell growth by stabilizing G-quadruplex DNA to induce tumor cell cycle arrest, DNA damage, and apoptosis [ 12 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Arene Ru(II) Complexes with Difluorinated Ligands Act as Potential Inducers of S-Phase Arrest via the Stabilization of c-myc G-Quadruplex DNA

et al. 2022

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Here, a series of half-sandwich arene Ru(II) complexes with difluorinated ligands [Ru(η6-arene)(L)Cl] (L1 = 2-(2,3-difluorophenyl)imidazole[4,5f][1,10]-phenanthroline; L2 = 2-(2,4-difluorophenyl)imidazole[4,5f][1,10]-phenanthroline; arene = benzene, toluene, and p-cymene) were synthesized and characterized. Molecular docking analysis showed that these complexes bind to c-myc G-quadruplex DNA through either groove binding or π–π stacking, and the relative difluorinated site in the main ligand plays a role in regulating the binding mode. The binding behavior of these complexes with c-myc G-quadruplex DNA was evaluated using ultraviolet–visible spectroscopy, fluorescence intercalator displacement assay, fluorescence resonance energy transfer melting assay, and polymerase chain reaction. The comprehensive analysis indicated that complex 1 exhibited a better affinity and stability in relation to c-myc G-quadruplex DNA with a DC50 of 6.6 μM and ΔTm values of 13.09 °C, than other molecules. Further activity evaluation results displayed that this class of complexes can also inhibit the growth of various tumor cells, especially complexes 3 and 6, which exhibited a better inhibitory effect against human U87 glioblastoma cells (51.61 and 23.75 μM) than other complexes, even superior to cisplatin (32.59 μM). Owing to a befitting lipophilicity associated with the high intake of drugs by tumor cells, complexes 3 and 6 had favorable lipid-water partition coefficients of −0.6615 and −0.8077, respectively. Moreover, it was found that complex 6 suppressed the proliferation of U87 cells mainly through an induced obvious S phase arrest and slight apoptosis, which may have resulted from the stabilization of c-myc G-quadruplex DNA to block the transcription and expression of c-myc. In brief, these types of arene Ru(II) complexes with difluorinated ligands can be developed as potential inducers of S-phase arrest and apoptosis through the binding and stabilization of c-myc G-quadruplex DNA, and could be used in clinical applications in the future.

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Ruthenium-mediated assembly and enhanced stability of heterometallic polystannides [Ru2Sn19]4− and [Ru2Sn20]6−

et al. 2022

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Cytotoxic organometallic [Ru(η6-anethole)(en)(X)]PF6 (X = Br or I) complexes: Synthesis, characterization and in vitro biological evaluation

Cited by 7 publications

References 19 publications

Cytotoxicity of new pyridazin‐3(2H)‐one derivatives orchestrating oxidative stress in human triple‐negative breast cancer (MDA‐MB‐468)

Cytotoxicity of new pyridazin‐3(2H)‐one derivatives orchestrating oxidative stress in human triple‐negative breast cancer (MDA‐MB‐468)

Arene Ru(II) Complexes with Difluorinated Ligands Act as Potential Inducers of S-Phase Arrest via the Stabilization of c-myc G-Quadruplex DNA

Ruthenium-mediated assembly and enhanced stability of heterometallic polystannides [Ru2Sn19]4− and [Ru2Sn20]6−

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