In vitro SOD-like activity of mono- and di-copper complexes with a phosphonate substituted SALAN-type ligand

Székács, Inna; Tokarz, Paweł; Horváth, Róbert; Kovács, Krisztina; Kubas, Adam; Shimura, Mari; Brasuń, Justyna; Murzin, Vadim; Caliebe, W.; Szewczuk, Zbigniew; Paluch, Aneta; Wojnárovits, László; Tóth, Tünde; Pap, József S.; Szyrwiel, Łukasz

doi:10.1016/j.cbi.2019.04.003

Cited by 9 publications

(5 citation statements)

References 67 publications

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“…Most metallic elements are in the form of metal ions in cells [32]. They can produce many bonds and cooperate with biomolecules, thus playing a variety of roles in organisms, such as electron transport [33], gas transport [34], and enzyme activity centers [35]. Following the RNA sequencing results, we found significant changes in genes and pathways associated with metal ion transport, particularly copper ion transport.…”

Section: Discussionmentioning

confidence: 73%

Effects of Zearalenone on Apoptosis and Copper Accumulation of Goat Granulosa Cells In Vitro

Liu

Wei³

et al. 2023

Biology

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Zearalenone (ZEA), also known as F-2 toxin, is a mycotoxin. Despite numerous reports of ZEA impairing livestock production performance and fertility, little information is available, including information about the mechanism underlying damage to cell metal ion transport. Copper, which is essential for cell survival as a metal ion, can consist of a variety of enzymes that facilitate abundant metabolic processes. However, the accumulation of copper in cells can have toxic effects. Here, we intended to determine whether ZEA could impair goat granulosa cells (GCs) and alter the cellular copper concentration. GCs were divided into a negative control (NC) group (cells cultured with 0.1% dimethyl sulfoxide (DMSO) for 8 h) and a ZEA group (cells cultured with 200 μmol/L ZEA diluted in DMSO for 8 h). The results showed that ZEA could inhibit GC proliferation and impair cell viability. GCs showed significant increases in the apoptosis rate and oxidative stress levels, while their ability to synthesize estrogen decreased. In addition, RNA-seq results showed dramatic changes in the expression of copper transport-related genes. The expression levels of ATPase copper transporting alpha (ATP7A) and ATPase copper transporting beta (ATP7B) were significantly downregulated (p < 0.01), while the expression of solute carrier family 31 member 1 (SLC31A1) was not modified in the ZEA group compared with the NC group. In accordance with these trends, the copper concentration increased significantly in the ZEA group (p < 0.01). In summary, our results show that ZEA can negatively affect GCs and cause copper accumulation. This finding may provide a prospective line of research on the relationship between ZEA and the transport of copper ions in GCs.

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Section: Discussionmentioning

confidence: 73%

Effects of Zearalenone on Apoptosis and Copper Accumulation of Goat Granulosa Cells In Vitro

Liu

Wei³

et al. 2023

Biology

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“…Called the SOD‐like assay, it consists of performing a reaction like that which occurs in cells. [ 2,68,69 ] However, pyridinium salts did not show SOD mimetic activity, which was observed only for AA (positive control). In this study, although we have focused on the antioxidant properties of Se‐containing pyridinium salts, it should be mentioned that, in addition to their potential antioxidant (and anticancer properties already mentioned), pyridinium salts can also inhibit the growth of bacteria and fungi, for example.…”

Section: Discussionmentioning

confidence: 99%

Bioactivity of selenium‐containing pyridinium salts: Prospecting future pharmaceutical constituents to treat liver diseases involving oxidative stress

Castro,

Alves,

de Bittencourt Maia

et al. 2023

J Biochem & Molecular Tox

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Redox imbalance leads to oxidative stress that causes irreversible cellular damage. The incorporation of the antioxidant element selenium (Se) in the structure of pyridinium salts has been used as a strategy in chemical synthesis and can be useful in drug development. We investigated the antioxidant activity of Se‐containing pyridinium salts (named Compounds 3A, 3B, and 3C) through in vitro tests. We focused our study on liver protein carbonylation, liver lipoperoxidation, free radical scavenging activity (1,1‐diphenyl‐2‐picryl‐hydrazil [DPPH]; 2,2′‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid [ABTS]), and enzyme‐mimetic activity assays (glutathione S‐transferase [GST]‐like; superoxide dismutase [SOD]‐like). In addition, 2‐(4‐chlorophenyl)‐2‐oxoethyl)‐2‐((phenylselanyl)methyl)pyridin‐1‐ium bromide (3C) was selected to evaluate the acute oral toxicity in mice due to the best antioxidant profile. The three compounds were effective in reducing the levels of protein carbonylation and lipoperoxidation in the liver in a µM concentration range. All compounds demonstrated scavenger activity of DPPH and ABTS radicals, and GST‐like action. No significant effects were detected in the SOD‐like assay. Experimental data also showed that the acute oral treatment of mice with Compound 3C (50 and 300 mg/kg) did not cause mortality or change markers of liver and kidney functions. In summary, our findings reveal the antioxidant potential of Se‐containing pyridinium salts in liver tissue, which could be related to their radical scavenging ability and mimetic action on the GST enzyme. They also demonstrate a low toxicity potential for Compound 3C. Together, the promising results open space for future studies on the therapeutic application of these molecules.

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“…The lack of a re-dissolution peak upon anodic polarization scans excludes the presence of free copper, or the release of copper from the reduced complex. [37] Reaction of [Cu(py 2 pn)] 2 + with O 2 *À…”

Section: Characterization Of the Complex In The Solid State And Solutionmentioning

confidence: 99%

Versatile Activity of a Copper(II) Complex Bearing a N₄‐Tetradentate Schiff Base Ligand with Reduced Oxygen Species

et al. 2022

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The reactivity of the Cu(II) complex of N,N'-bis(pyridin-2-ylmethylene)propane-1,3-diamine (py 2 pn), [Cu(py 2 pn)(ClO 4 ) 2 ], toward O 2and H 2 O 2 has been examined. The complex reacts with O 2 *À with fast second order kinetics, k McF = 4.05 × 10 6 M À 1 s À 1 , employing the Cu(II)/Cu(I) couple proved by spectroscopic detection of the reduced form at low temperature. At À 40 °C in DMF, the reaction of the complex with H 2 O 2 /Et 3 N yields an stable end-on Cu(II)-hydroperoxide, with k OOH = 0.31 min À 1 , the formation of which has been established by DFT calculations, electronic and EPR spectra. At room temperature, the end-on Cu(II)-hydroperoxide reacts with a second Cu(II) complex to evolve O 2 , with k CAT = 83.2 M À 2 s À 1 . The Cu(II)-hydroperoxide can mediate phenol oxidation, probably through a trigonal bipyramidal ternary transition state based on DFT analysis, favored over catalase activity when low proportion of catalyst is used. In these reactions, structural constraints imposed by the ligand distort the coordination geometry of the metal and controls reactivity.

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In vitro SOD-like activity of mono- and di-copper complexes with a phosphonate substituted SALAN-type ligand

Cited by 9 publications

References 67 publications

Effects of Zearalenone on Apoptosis and Copper Accumulation of Goat Granulosa Cells In Vitro

Effects of Zearalenone on Apoptosis and Copper Accumulation of Goat Granulosa Cells In Vitro

Bioactivity of selenium‐containing pyridinium salts: Prospecting future pharmaceutical constituents to treat liver diseases involving oxidative stress

Versatile Activity of a Copper(II) Complex Bearing a N₄‐Tetradentate Schiff Base Ligand with Reduced Oxygen Species

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In vitro SOD-like activity of mono- and di-copper complexes with a phosphonate substituted SALAN-type ligand

Cited by 9 publications

References 67 publications

Effects of Zearalenone on Apoptosis and Copper Accumulation of Goat Granulosa Cells In Vitro

Effects of Zearalenone on Apoptosis and Copper Accumulation of Goat Granulosa Cells In Vitro

Bioactivity of selenium‐containing pyridinium salts: Prospecting future pharmaceutical constituents to treat liver diseases involving oxidative stress

Versatile Activity of a Copper(II) Complex Bearing a N4‐Tetradentate Schiff Base Ligand with Reduced Oxygen Species

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Versatile Activity of a Copper(II) Complex Bearing a N₄‐Tetradentate Schiff Base Ligand with Reduced Oxygen Species