Synthesis, characterization, anticancer and antioxidant activity of new nickel(II) and copper(II) flavonoid complexes

Alper, Pınar; Erkısa, Merve; Gençkal, Hasene Mutlu; Şahin, Saliha; Ulukaya, Engin; Arı, Ferda

doi:10.1016/j.molstruc.2019.07.009

Cited by 33 publications

(14 citation statements)

References 51 publications

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“…protocol was used to dock the protein Human pancreatic α-amylase and the flavonoid compounds [35][36][37][38][39].…”

Section: Plos Onementioning

confidence: 99%

“…This is due to the attainment of extra resonating site and better stability of flavonoid metal complex radical than free flavonoids possess [16,28]. Moreover, flavonoids and their derivatives exhibit wide spectrum of therapeutical benefits, including antidiabetic [29,30], antiviral [26], antibacterial [31,32], anti-inflammatory [33], cardioprotective [34], anticancer [35], antiaging [36], neuroprotective/antioxidant [35,37,38], antiproliferative [39] and antiestrogenic/estrogenic activities [40,41].…”

Section: Introductionmentioning

confidence: 99%

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Pharmacokinetics and drug-likeness of antidiabetic flavonoids: Molecular docking and DFT study

et al. 2021

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Computer aided toxicity and pharmacokinetic prediction studies attracted the attention of pharmaceutical industries as an alternative means to predict potential drug candidates. In the present study, in-silico pharmacokinetic properties (ADME), drug-likeness, toxicity profiles of sixteen antidiabetic flavonoids that have ideal bidentate chelating sites for metal ion coordination were examined using SwissADME, Pro Tox II, vNN and ADMETlab web tools. Density functional theory (DFT) calculations were also employed to calculate quantum chemical descriptors of the compounds. Molecular docking studies against human alpha amylase were also conducted. The results were compared with the control drugs, metformin and acarbose. The drug-likeness prediction results showed that all flavonoids, except myricetin, were found to obey Lipinski’s rule of five for their drug like molecular nature. Pharmacokinetically, chrysin, wogonin, genistein, baicalein, and apigenin showed best absorption profile with human intestinal absorption (HIA) value of ≥ 30%, compared to the other flavonoids. Baicalein, butein, ellagic acid, eriodyctiol, Fisetin and quercetin were predicted to show carcinogenicity. The flavonoid derivatives considered in this study are predicted to be suitable molecules for CYP3A probes, except eriodyctiol which interacts with P-glycoprotein (p-gp). The toxicological endpoints prediction analysis showed that the median lethal dose (LD50) values range from 159–3919 mg/Kg, of which baicalein and quercetin are found to be mutagenic whereas butein is found to be the only immunotoxin. Molecular docking studies showed that the significant interaction (-7.5 to -8.3 kcal/mol) of the studied molecules in the binding pocket of the α-amylase protein relative to the control metformin with the crucial amino acids Asp 197, Glu 233, Asp 197, Glu 233, Trp 59, Tyr 62, His 101, Leu 162, Arg 195, His 299 and Leu 165. Chrysin was predicted to be a ligand with high absorption and lipophilicity with 84.6% absorption compared to metformin (78.3%). Moreover, quantum chemical, ADMET, drug-likeness and molecular docking profiles predicted that chrysin is a good bidentate ligand.

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“…protocol was used to dock the protein Human pancreatic α-amylase and the flavonoid compounds [35][36][37][38][39].…”

Section: Plos Onementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Pharmacokinetics and drug-likeness of antidiabetic flavonoids: Molecular docking and DFT study

et al. 2021

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“…Additionally, Epa value determines antioxidant activity of flavonoid, because if the Epa is lower, the antioxidant activity of flavonoid is higher. Quercetin (3) (Epa = 0.33 V) is a better antioxidant compound than naringenin (30) (Epa = 0.45 V) and that influences antioxidant properties of their complexes, because quercetin (3) complexes have stronger antioxidant properties than naringenin (30) complexes [251]. which may be released during lipid peroxidation.…”

Section: Complexes Of Flavonoids With Metal Ionsmentioning

confidence: 99%

Overview of the Antioxidant and Anti-Inflammatory Activities of Selected Plant Compounds and Their Metal Ions Complexes

et al. 2021

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Numerous plant compounds and their metal-ion complexes exert antioxidative, anti-inflammatory, anticancer, and other beneficial effects. This review highlights the different bioactivities of flavonoids, chromones, and coumarins and their metal-ions complexes due to different structural characteristics. In addition to insight into the most studied antioxidative properties of these compounds, the first part of the review provides a comprehensive overview of exogenous and endogenous sources of reactive oxygen and nitrogen species, oxidative stress-mediated damages of lipids and proteins, and on protective roles of antioxidant defense systems, including plant-derived antioxidants. Additionally, the review covers the anti-inflammatory and antimicrobial activities of flavonoids, chromones, coumarins and their metal-ion complexes which support its application in medicine, pharmacy, and cosmetology.

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“…Studies have shown that coordination of quercetin with metal ions can increase the antioxidant activity and ultraoxygen anion elimination than quercetin itself [ 24 – 26 ]. The strong ability of quercetin to chelate with different metal ions such as Tb(III) [ 27 ], Mg(II) [ 28 ], Cu(II) [ 29 ], Fe(II) [ 3 ], Cr(III) [ 30 ], Co(II) [ 31 ], Sn(II) [ 32 ], Vo(IV) [ 33 ], Zn(II) [ 34 ], Mn(II) [ 35 ], Pb(II) [ 36 ], and Ni(II) [ 37 ] can increase the solubility and bioavailability of quercetin and promote new pharmacological activity [ 38 ].…”

Section: Introductionmentioning

confidence: 99%

Quercetin as a Precursor for the Synthesis of Novel Nanoscale Cu (II) Complex as a Catalyst for Alcohol Oxidation with High Antibacterial Activity

Moodi

Bagherzade

Peters

2021

Bioinorganic Chemistry and Applications

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Quercetin (3,3′,4′,5,7-pentahydroxyflavone) is one of the dietary flavonoids, distributed in medicinal plants, vegetables, and fruits. Quercetin has the ability to bind with several metal ions to increase its biological activities. In the last two decades, quercetin has attracted considerable attention due to the biological and pharmaceutical activities such as antioxidant, antibacterial, and anticancer. In the present study, quercetin and ethanolamine were used for the synthesis Schiff base complex, which was characterized by IR, 1H NMR, and 13C NMR spectroscopy. The Schiff base has been employed as a ligand for the synthesis of novel nanoscale Cu (II) complex. The product was characterized by FT-IR spectroscopy, FESEM, and XRD. Significantly, the product showed remarkable catalytic activity towards the oxidation of primary and secondary alcohols. The antibacterial activity of the final product was assessed against Staphylococcus aureus (Gram‐positive) and Escherichia coli (Gram‐negative) bacteria using an inhibition zone test. The synthesized nanoscale Cu (II) complex exhibited a strong antibacterial activity against both Gram-positive and Gram-negative bacteria.

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Synthesis, characterization, anticancer and antioxidant activity of new nickel(II) and copper(II) flavonoid complexes

Cited by 33 publications

References 51 publications

Pharmacokinetics and drug-likeness of antidiabetic flavonoids: Molecular docking and DFT study

Pharmacokinetics and drug-likeness of antidiabetic flavonoids: Molecular docking and DFT study

Overview of the Antioxidant and Anti-Inflammatory Activities of Selected Plant Compounds and Their Metal Ions Complexes

Quercetin as a Precursor for the Synthesis of Novel Nanoscale Cu (II) Complex as a Catalyst for Alcohol Oxidation with High Antibacterial Activity

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