Physicochemical, antioxidant, DNA cleaving properties and antimicrobial activity of fisetin-copper chelates

Łodyga-Chruścińska, Elżbieta; Pilo, Maria Itria; Zucca, Antonio; Garribba, Eugenio; Klewicka, Elżbieta; Rowińska‐Żyrek, Magdalena; Symonowicz, Marzena; Chruściński, Longin; Чещевик, В. Т.

doi:10.1016/j.jinorgbio.2017.12.006

Cited by 30 publications

(14 citation statements)

References 102 publications

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“…Dimitric Markovic [ 34 ] et al found that at neutral or alkaline pH, the chelating group was the catechol in the B ring and that fisetin bound iron in a 1:1 ratio. Several studies have also looked at copper binding by fisetin [ 33 , 35 ]. At neutral pH, fisetin also binds copper in a 1:1 ratio and, as with iron, the main chelating group is the catechol moiety in the B ring [ 35 ].…”

Section: Discussionmentioning

confidence: 99%

“…Metal chelation has been implicated in the beneficial effects of a number of different flavonoids including fisetin [ 31 ]. Indeed, fisetin has been reported to bind both iron [ 31 , 32 , 33 , 34 ] and copper [ 33 , 35 ]. Therefore, in this study it was asked if at least some of the neuroprotective and/or anti-inflammatory properties of fisetin could be due to its ability to modulate the effects of iron and/or copper on cells.…”

Section: Introductionmentioning

confidence: 99%

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Modulation of the Neuroprotective and Anti-inflammatory Activities of the Flavonol Fisetin by the Transition Metals Iron and Copper

Maher

2020

Antioxidants

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Alterations occur in the homeostasis of the transition metals iron (Fe2+) and copper (Cu2+) during aging and these are further amplified in neurodegenerative diseases, including Alzheimer’s disease (AD). These observations suggest that the most effective drug candidates for AD might be those that can reduce these alterations. The flavonoid fisetin has both neuroprotective and anti-inflammatory activity both in vitro and in vivo and can bind both iron and copper suggesting that its chelating activity might play a role in its beneficial effects. To test this idea, the effects of iron and copper on both the neuroprotective and anti-inflammatory activities of fisetin were examined. It is shown that while fisetin can reduce the potentiation of cell death by iron and copper in response to treatments that lower glutathione levels, it is much less effective when the metals are combined with other inducers of oxidative stress. In addition, iron but not copper reduces the anti-inflammatory effects of fisetin in a dose-dependent manner. These effects correlate with the ability of iron but not copper to block the induction of the antioxidant transcription factor, Nrf2, by fisetin. In contrast, although the flavanone sterubin also binds iron, the metal has no effect on sterubin’s ability to induce Nrf2 or protect cells from toxic or pro-inflammatory insults. Together, these results suggest that while iron and copper binding could contribute to the beneficial effects of neuroprotective compounds in the context of neurodegenerative diseases, the consequences of this binding need to be fully examined for each compound.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Modulation of the Neuroprotective and Anti-inflammatory Activities of the Flavonol Fisetin by the Transition Metals Iron and Copper

Maher

2020

Antioxidants

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“…Out of all ions, copper seems very interesting and promising because of its biological importance and properties. It is essential in the photosynthesis process and respiration and it consists of an active center of many enzymes [13,14]. Therefore copper was one of the metals subjected to our research to determine biological activity of its complexes with CA.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore copper was one of the metals subjected to our research to determine biological activity of its complexes with CA. In complexes with fisetin-polyphenolic compound from the group of isoflavonoids, it revealed high antibacterial and antifungal activity [14]. On the other hand copper complexed with resveratrol acts as a factor, which promotes fragmentation of nuclear DNA in human cells [15].…”

Section: Introductionmentioning

confidence: 99%

Biological Activity of New Cichoric Acid–Metal Complexes in Bacterial Strains, Yeast-Like Fungi, and Human Cell Cultures In Vitro

et al. 2020

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Cichoric acid (CA) belongs to the group of polyphenols, which occurs in a variety of plant species and it is characterized by anticancer, antibacterial, and antiviral properties. Selected polyphenols have the ability to combine with metal ions to form chelate complexes that reveal greater biological activity than free compounds. In order to study possible antimicrobial and anticancer effect of CA and its complexes with copper(II)/zinc(II)/nickel(II)/cobalt(II) we decided to conduct cytotoxicity tests to estimate the most effective concentrations of tested compounds. The results of the presented study demonstrated, for the first time, that the treatment with newly synthesized CA-metal complexes has anticancer and antimicrobial effects, which were examined in seven different cell lines: MCF-7, MDA-MB-231, and ZR-75-1 breast cancer cell lines, A375 melanoma cell line, DLD-1 cell line, LN-229 cell line, FN cell line; five bacterial strains: Escherichia coli, Pseudomonas aeruginosa, Staphylococcus epidermidis, Proteus vulgaris, Lactobacillus rhamnosus, yeast Sacchcaromyces boulardii, and pathogenic yeast-like fungi Candida albicans. The presented study indicates that CA-metal complexes could be considered as a potential supplementary tool in anticancer therapy, however, because of their possible toxic activity on fibroblasts, they should be used with caution. Some of the tested complexes have also preservative properties and positive influence on normal non-pathogenic microorganisms, which was demonstrated in selected microbial strains, therefore they may serve as food preservatives of natural origin with cytoprotective properties.

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“…The compounds with two or more nitrogen atoms are capable chelating agents, which can easily bind to the metal ions function as a cofactor in enzymatic reactions. In some cases, it is thought that the efficacy is dependent on the selectivity arose from the chelation of drug molecules with trace metals …”

Section: Introductionmentioning

confidence: 99%

Iron(III) and nickel(II) complexes of tetradentate thiosemicarbazones: Synthesis, structure, cytotoxicity, and lipophilicity

Süleymanoğlu

Kaya

Erdem‐Kuruca

et al. 2019

J Biochem & Molecular Tox

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Eighteen of the iron(III) and nickel(II) complexes with tetradentate thiosemicarbazidato ligands were synthesized and described, by analytical and spectroscopic methods. Two complexes as an example to the iron and nickel centered ones were crystallographically analyzed to confirm the molecular structures. Cytotoxic effects of the complexes on K562 chronic myeloid leukemia cells were determined by 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay. For comparison, human umbilical vein endothelial cells (HUVECs) was used as a noncancerous cell line. While four of the iron(III) complexes exhibited the antileukemic effect with 50% inhibition of cell growth (IC50) values in the 3.4 to 6.9 μg/mL range on K562 cell line, the nickel(II) complexes showed no significant effect on both cell lines. The complexes Fe4, Fe5, and Fe6, bearing 4‐methoxy substituent exhibited relatively high antiproliferative activity on both cell lines. Complex Fe3 with 3‐methoxy and S‐allyl groups exhibited a selectivity between K562 and HUVEC cells by IC50 values of 6.9 and >10 μg/mL, respectively. Lipophilicity, a key parameter for bioavailability and oral administration, was found in the range of −0.3 and +1.3 that desired for drug active ingredients. The results were discussed in the context of a structure‐activity relationship.

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Physicochemical, antioxidant, DNA cleaving properties and antimicrobial activity of fisetin-copper chelates

Cited by 30 publications

References 102 publications

Modulation of the Neuroprotective and Anti-inflammatory Activities of the Flavonol Fisetin by the Transition Metals Iron and Copper

Modulation of the Neuroprotective and Anti-inflammatory Activities of the Flavonol Fisetin by the Transition Metals Iron and Copper

Biological Activity of New Cichoric Acid–Metal Complexes in Bacterial Strains, Yeast-Like Fungi, and Human Cell Cultures In Vitro

Iron(III) and nickel(II) complexes of tetradentate thiosemicarbazones: Synthesis, structure, cytotoxicity, and lipophilicity

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