A new calcium 2,5-dihydroxybenzoate: Synthesis, characterization and antioxidant studies and stress mediated cytotoxity in MCF-7 cells

Kalinowska, Monika; Mazur, Liliana; Jabłońska-Trypuć, Agata; Lewandowski, W.

doi:10.1016/j.jscs.2017.12.006

Cited by 11 publications

(14 citation statements)

References 44 publications

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“…The complexation of chlorogenic acid with oxidovanadium(IV) also improved the antioxidant and anti-cancer properties against the human breast cancer cell line SKBR3 [ 20 ]. The higher antioxidant activity of metal complexes compared to free phenolic compounds was observed in other cases as well, e.g., Fe(II), Cu(II), Ce(IV), La(III) and oxovanadium(IV) complexes of chrysin; complexes of apigenin with La(III), Mg(II) and luteolin with oxovanadium [ 21 ] or calcium complex of gentisic acid [ 22 ]. It should be kept in mind that the antioxidants may act as pro-oxidants depending on their concentration or the presence of some metal cations.…”

Section: Introductionmentioning

confidence: 99%

Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies

et al. 2020

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The structure of the Zn(II) complex of 5-caffeoylquinic acid (chlorogenic acid, 5-CQA) and the type of interaction between the Zn(II) cation and the ligand were studied by means of various experimental and theoretical methods, i.e., electronic absorption spectroscopy UV/Vis, infrared spectroscopy FT-IR, elemental, thermogravimetric and density functional theory (DFT) calculations at B3LYP/6-31G(d) level. DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), FRAP (ferric reducing antioxidant power), CUPRAC (cupric reducing antioxidant power) and trolox oxidation assays were applied in study of the anti-/pro-oxidant properties of Zn(II) 5-CQA and 5-CQA. The antimicrobial activity of these compounds against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus, Salmonella enteritidis and Candida albicans was tested. An effect of Zn(II) chelation by chlorogenic acid on the anti-/pro-oxidant and antimicrobial activities of the ligand was discussed. Moreover, the mechanism of the antioxidant properties of Zn(II) 5-CQA and 5-CQA were studied on the basis of the theoretical energy descriptors and thermochemical parameters. Zn(II) chlorogenate showed better antioxidant activity than chlorogenic acid and commonly applied natural (L-ascorbic acid) and synthetic antioxidants (butylated hydroxyanisol (BHA) and butylated hydroxytoluene (BHT)). The pro-oxidant activity of Zn(II) 5-CQA was higher than the ligand and increased with the rise of the compound concentration The type of Zn(II) coordination by the chlorogenate ligand strongly affected the antioxidant activity of the complex.

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Section: Introductionmentioning

confidence: 99%

Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies

et al. 2020

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“…In the literature, different values of the EC 50 for UA were reported: 0.108 mM [ 40 ], 0.131 mM [ 41 ] and 6.88 µM [ 42 ]; for the concentration of UA, 0.333 mM the % I = 10.62 [ 43 ]. The obtained values of EC 50 for the studied compounds pointed that the studied compounds were rather week scavengers of the radicals, when compared with some phenolic compounds or commercially applied antioxidants (butylated hydroxytoluene or butylated hydroxyanisole) [ 14 , 15 ]. On the other hand, it is interesting that the complexation of Cu 2+ with ursolic acid caused an increase in the antiradical activity of the molecule, as compared with ligand alone.…”

Section: Resultsmentioning

confidence: 99%

“…The results pointed that metal complexation with ursolic acid may be a promising way to overcome its low solubility and may increase the biological application. There are many more examples of metal complexes with higher antioxidant or anticancer activities than ligand alone, e.g., alkali metal salts and zinc (II) complex of chlorogenic acid [ 14 ], Ca(II) complex of gentisic acid [ 15 ], metal complexes of cichoric acid [ 16 ] and metal complexes of flavones [ 17 ]. The reasons for increasing antioxidant activity of metal complexes compared to ligand alone include the following: (I) stabilization of the semiquinone radicals by metal cations, (II) involvement of the metallic center in the reaction with the radicals and acquisition of additional superoxide dismutating centers, (III) changes in the redox potential and thermochemical parameters (i.e., lower dissociation energy of O-H and ionization energy) of complexes compared to ligands, and (IV) different kinetics of the reaction between complexes/ligands and radicals.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Antioxidant Activity of Ursolic Acid by Complexation with Copper (II): Experimental and Theoretical Study

2021

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The copper (II) complex of ursolic acid (Cu(II) UA) was synthesized and discussed in terms of its infrared, UV–visible spectra, quantum-chemical calculations at B3LYP/6-31G(d) level and antioxidant capacity. The copper (II) complex was stable in methanolic solution with the molar ratio metal:ligand 1:1. The data obtained by FT-IR confirmed the metal ion coordination through the carboxylate anion. The antioxidant properties of ursolic acid and its complex with Cu were discussed on the basis of energy of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and values of chemical reactivity parameters. The antiradical properties of ursolic acid and the Cu (II) complex were examined against DPPH• and HO• radicals, and the ferric reducing antioxidant power (FRAP) was examined. The Cu(II) complex showed higher antioxidant activity than ursolic acid, i.e., in DPPH• assay, the EC50 for UA was 47.0 mM, whereas, for Cu(II), UA EC50 = 19.5 mM; the FRAP value for UA was 20.8 µMFe2+, and 35.4 µMFe2+ for Cu(II) UA (compound concentration 3 mM). Although there was no distinct difference in the antioxidant activity against HO• between these two chemicals, they were both better HO• scavengers than DPPH• and showed different kinetics in the reaction with DPPH•.

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“…Metal ions Mg(II) and Mn(II) studied in the above work are characterized by a high ionic potential, thanks to In our study, the complex of isoferulic acid with metal ions had significantly higher antioxidant activity compared to alone IFA in DPPH • and CUPRAC assays. Multiple reports in the literature have shown that the complexation of phenolic compounds with metal ions may increase biological activity and bioavailability of the parent ligand [42][43][44][45], but there are also many studies describing a decrease in ligand activity due to the complexation with metal ions [90]. The higher biological activity of metal complexes compared with ligand was reported by other authors as well.…”

Section: Anti-/pro-oxidant Studymentioning

confidence: 89%

“…In the work of Rubens and Wagner [43], complexation of rutin and galangin with Cu(II), Fe(II), Al(III), and Zn(II) ions increased their DPPH • radical scavenging activity, i.e., the EC 50 value for rutin was 18.23 µM, while for the complexes it was in the range of 5.02-3.76 µM [43]. Ca(II) complex of gentisic acid shows higher antioxidant activity in DPPH • (2,2-diphenyl-1-picrylhydrazyl) radical, FRAP (ferric reducing antioxidant power), and CUPRAC (cupric reducing antioxidant capacity) assays than the ligand alone [44]. Moreover, it was proven that phenolic compound complexes with transition metals (such as Fe(II) or Mn(II)) often have higher bioavailability than pure ligands, e.g., quercetin shows increasing bioavailability in combination with Cu(II) ions [45].…”

Section: Introductionmentioning

confidence: 97%

Crystal Structure, Spectroscopic Characterization, Antioxidant and Cytotoxic Activity of New Mg(II) and Mn(II)/Na(I) Complexes of Isoferulic Acid

et al. 2021

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The Mg(II) and heterometallic Mn(II)/Na(I) complexes of isoferulic acid (3-hydroxy-4-methoxycinnamic acid, IFA) were synthesized and characterized by infrared spectroscopy FT-IR, FT-Raman, electronic absorption spectroscopy UV/VIS, and single-crystal X-ray diffraction. The reaction of MgCl2 with isoferulic acid in the aqueous solutions of NaOH resulted in synthesis of the complex salt of the general formula of [Mg(H2O)6]⋅(C10H9O4)2⋅6H2O. The crystal structure of this compound consists of discrete octahedral [Mg(H2O)6]2+ cations, isoferulic acid anions and solvent water molecules. The hydrated metal cations are arranged among the organic layers. The multiple hydrogen-bonding interactions established between the coordinated and lattice water molecules and the functional groups of the ligand stabilize the 3D architecture of the crystal. The use of MnCl2 instead of MgCl2 led to the formation of the Mn(II)/Na(I) complex of the general formula [Mn3Na2(C10H7O4)8(H2O)8]. The compound is a 3D coordination polymer composed of centrosymmetric pentanuclear subunits. The antioxidant activity of these compounds was evaluated by assays based on different antioxidant mechanisms of action, i.e., with •OH, DPPH• and ABTS•+ radicals as well as CUPRAC (cupric ions reducing power) and lipid peroxidation inhibition assays. The pro-oxidant property of compounds was measured as the rate of oxidation of Trolox. The Mg(II) and Mn(II)/Na(I) complexes with isoferulic acid showed higher antioxidant activity than ligand alone in DPPH (IFA, IC50 = 365.27 μM, Mg(II) IFA IC50 = 153.50 μM, Mn(II)/Na(I) IFA IC50 = 149.00 μM) and CUPRAC assays (IFA 40.92 μM of Trolox, Mg(II) IFA 87.93 μM and Mn(II)/Na(I) IFA 105.85 μM of Trolox; for compounds’ concentration 10 μM). Mg(II) IFA is a better scavenger of •OH than IFA and Mn(II)/Na(I) IFA complex. There was no distinct difference in ABTS•+ and lipid peroxidation assays between isoferulic acid and its Mg(II) complex, while Mn(II)/Na(I) complex showed lower activity than these compounds. The tested complexes displayed only slight antiproliferative activity tested in HaCaT human immortalized keratinocyte cell line within the solubility range. The Mn(II)/Na(I) IFA (16 μM in medium) caused an 87% (±5%) decrease in cell viability, the Mg salt caused a comparable, i.e., 87% (±4%) viability decrease in a concentration of 45 μM, while IFA caused this level of cell activity attenuation (87% ± 5%) at the concentration of 1582 μM (significant at α = 0.05).

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A new calcium 2,5-dihydroxybenzoate: Synthesis, characterization and antioxidant studies and stress mediated cytotoxity in MCF-7 cells

Cited by 11 publications

References 44 publications

Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies

Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies

Enhanced Antioxidant Activity of Ursolic Acid by Complexation with Copper (II): Experimental and Theoretical Study

Crystal Structure, Spectroscopic Characterization, Antioxidant and Cytotoxic Activity of New Mg(II) and Mn(II)/Na(I) Complexes of Isoferulic Acid

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