Redox-active metal(II) complexes of sterically hindered phenolic ligands: Antibacterial activity and reduction of cytochrome c. Part II. Metal(II) complexes of o-diphenol derivatives of thioglycolic acid

Loginova, N. V.; Ковальчук, Т. В.; Faletrov, Yaroslav V.; Halauko, Yury S.; Osipovich, N. P.; Полозов, Г. И.; Желдакова, Римма Анатольевна; Gres, A.T.; Halauko, A.S.; Azarko, I.I.; Shkumatov, V. M.; Шадыро, О. И.

doi:10.1016/j.poly.2011.07.008

Cited by 13 publications

(6 citation statements)

References 44 publications

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“…Previously it was shown that the above-mentioned complexes exhibit a wide spectrum of activities in vitro, comparable with those of well-known antibiotics, against both Gram-positive and Gram-negative bacteria as well as yeast and molds. [41][42][43][44] Biocidal activity of the abovementioned metal complexes is implemented through several mechanisms, involving metal ions interaction with functional groups of microorganisms cell wall and essential intracellular molecules [45] as well as redox activity of complexes itself, disrupting the function of cellular organelles. [46] The anticorrosion behavior and antibacterial activity of the modified coatings against Gram-positive (Staphylococcus carnosus) and Gramnegative (Escherichia coli) bacteria were examined.…”

Section: Introductionmentioning

confidence: 99%

“…In this paper, we explore the characteristics of anti‐corrosion antibacterial PEO coating for magnesium substrate obtained by means of deposition of the Ag(I) and Cu(II) complexes with sterically hindered phenolic (SHP) derivatives of thioglycolic and thiopropionic acids on the top of PEO surface, used as a carrier for bioactive compounds. Previously it was shown that the above‐mentioned complexes exhibit a wide spectrum of activities in vitro , comparable with those of well‐known antibiotics, against both Gram‐positive and Gram‐negative bacteria as well as yeast and molds [41–44] . Biocidal activity of the above‐mentioned metal complexes is implemented through several mechanisms, involving metal ions interaction with functional groups of microorganisms cell wall and essential intracellular molecules [45] as well as redox activity of complexes itself, disrupting the function of cellular organelles [46] .…”

Section: Introductionmentioning

confidence: 99%

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Characterization and In Vitro Behavior of PEO Coated Mg Modified with Antibacterial Ag(I) and Cu(II) Complexes

Tsimafeyeva,

Starykevich,

Snihirova

et al. 2024

Chemistry A European J

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The use of Mg‐based biomaterials with a number of their advantageous properties are overshadowed by uncontrollable metal corrosion. Moreover, the use of implants goes alongside with the threat of pathogens‐associated complications. In this study, PEO coated Mg biomaterial loaded with antibacterial Ag(I) and Cu(II) complexes is produced and tested to meet both appropriate protective characteristics as well as sufficient level of antibacterial activity. To achieve a suitable level of anticorrosion protection phosphate and fluoride‐phosphate electrolytes are used in the PEO process. Investigation of the surface thickness and morphology done by means of cross‐section analysis and scanning electron microscopy (SEM), as well as electrochemical impedance spectroscopy (EIS) assay show precedence of the fluoride containing PEO coating and make it the material of choice for further modification with Ag(I) and Cu(II) complexes. The presence of the complexes on the PEO surface is confirmed by energy dispersive X‐ray spectroscopy (EDX). X‐ray photoelectron spectroscopy (XPS), transmission electron microscopy (TEM) and glow discharge optical emission spectroscopy (GDOES) are used to estimate the complexes’ chemical state and depth of penetration in the coating surface. Based on the results of antibacterial assay, the modified coatings are found to be active against both Gram‐positive and Gram‐negative bacteria.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Characterization and In Vitro Behavior of PEO Coated Mg Modified with Antibacterial Ag(I) and Cu(II) Complexes

Tsimafeyeva,

Starykevich,

Snihirova

et al. 2024

Chemistry A European J

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“…Along with the pronounced biological activity, these compounds are widely used to obtain functionalized materials [ 13 , 14 , 15 , 16 ]; they serve as building blocks for coatings design [ 17 ], as the basis for organic batteries and redox capacitors [ 18 , 19 ], and as redox-based molecular memory-films [ 20 ] due to their ability to accept, store and donate electrons and protons. Researchers consider S-functionalized sterically hindered catechols (quinones) as promising chelating ligands in metal complexes [ 21 , 22 , 23 , 24 , 25 , 26 , 27 ], polynuclear compounds and coordination polymers [ 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidant Activity of New Catechol Thioethers with the Methylene Linker

et al. 2022

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Novel catechol thio-ethers with different heterocyclic substituents at sulfur atom were prepared by reacting 3,5-di-tert-butyl-6-methoxymethylcatechol with functionalized thiols under acidic conditions. A common feature of compounds is a methylene bridge between the catechol ring and thioether group. Two catechols with the thio-ether group, bound directly to the catechol ring, were also considered to assess the effect of the methylene linker on the antioxidant properties. The crystal structures of thio-ethers with benzo-thiazole moieties were established by single-crystal X-ray analysis. The radical scavenging and antioxidant activities were determined using 2,2′-diphenyl-1-picrylhydrazyl radical test, ABTS∙+, CUPRAC (TEAC) assays, the reaction with superoxide radical anion generated by xanthine oxidase (NBT assay), the oxidative damage of the DNA, and the process of lipid peroxidation of rat liver (Wistar) homogenates in vitro. Most catechol-thioethers exhibit the antioxidant effect, which varies from mild to moderate depending on the model system. The dual anti/prooxidant activity characterizes compounds with adamantyl or thio-phenol substituent at the sulfur atom. Catechol thio-ethers containing heterocyclic groups (thiazole, thiazoline, benzo-thiazole, benzo-xazole) can be considered effective antioxidants with cytoprotective properties. These compounds can protect molecules of DNA and lipids from the different radical species.

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“…Hence, copper(II) complexes of the type CuL 2 with 4,6-di-tert-butyl-3-(2-hydroxyethylsulfanyl)-1,2-benzenedithiol and 2-[4,6-di-tert-butyl-2,3-dihydroxyphenylsulfanyl] acetic acid exhibit fungicidal properties [ 35 ]. Iron(II), copper(II), and related cobalt(II), nickel(II), and zinc(II) complexes based on 2-(4,6-di-tert-butyl-2,3-dihydroxyphenylsulfanyl)acetic and 2-(4,6-di-tert-butyl-2,3-dihydroxyphenylsulphenyl)acetic acids possess remarkable antibacterial activity [ 36 ]. Complexes of copper(II), cobalt(II), and nickel(II) with 4,6-di-tert-butyl-3-(2-hydroxyethylsulfanyl)-1,2-benzenedithiol, along with their fungicidal activity, inhibit the replication of the human immunodeficiency virus [ 37 ].…”

Section: Introductionmentioning

confidence: 99%

Triphenylantimony(V) Catecholates of the Type (3-RS-4,6-DBCat)SbPh3-Catechol Thioether Derivatives: Structure, Electrochemical Properties, and Antiradical Activity

et al. 2021

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A new series of triphenylantimony(V) 3-alkylthio/arylthio-substituted 4,6-di-tert-butylcatecholates of the type (3-RS-4,6-DBCat)SbPh3, where R = n-butyl (1), n-hexyl (2), n-octyl (3), cyclopentyl (4), cyclohexyl (5), benzyl (6), phenyl (7), and naphthyl-2 (8), were synthesized from the corresponding catechol thioethers and Ph3SbBr2 in the presence of a base. The crystal structures of 1, 2, 3, and 5 were determined by single-crystal X-ray analysis. The coordination polyhedron of 1–3 is better described as a tetragonal pyramid with a different degree of distortion, while that for 5- was a distorted trigonal bipyramid (τ = 0.014, 0.177, 0.26, 0.56, respectively). Complexes demonstrated different crystal packing of molecules. The electrochemical oxidation of the complexes involved the catecholate group as well as the thioether linker. The introduction of a thioether fragment into the aromatic ring of catechol ligand led to a shift in the potential of the “catechol/o-semiquinone” redox transition to the anodic region, which indicated the electron-withdrawing nature of the RS group. The radical scavenging activity of the complexes was determined in the reaction with DPPH radical.

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Redox-active metal(II) complexes of sterically hindered phenolic ligands: Antibacterial activity and reduction of cytochrome c. Part II. Metal(II) complexes of o-diphenol derivatives of thioglycolic acid

Cited by 13 publications

References 44 publications

Characterization and In Vitro Behavior of PEO Coated Mg Modified with Antibacterial Ag(I) and Cu(II) Complexes

Characterization and In Vitro Behavior of PEO Coated Mg Modified with Antibacterial Ag(I) and Cu(II) Complexes

Synthesis and Antioxidant Activity of New Catechol Thioethers with the Methylene Linker

Triphenylantimony(V) Catecholates of the Type (3-RS-4,6-DBCat)SbPh3-Catechol Thioether Derivatives: Structure, Electrochemical Properties, and Antiradical Activity

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