The influence of some triphenylantimony(V) catecholates and <i>o</i>‐amidophenolates on lipid peroxidation<i>in vitro</i>

Smolyaninov, I. V.; Antonova, N. A.; Poddel’sky, Andrey I.; Осипова, В. П.; Берберова, Н. Т.; Pimenov, Yuri T.

doi:10.1002/aoc.2854

Cited by 26 publications

(8 citation statements)

References 61 publications

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“…The level of lipid peroxidation was estimated in the course of non‐enzymic reaction promoted by the ‘ascorbic acid–(NH 4 ) 2 Fe(SO 4 ) 2 ’ system. It is shown that the initial complex 1 (Table ) decreases the lipid oxidation of organ tissue homogenates by 10–35% compared with the control experiment, corresponding to earlier results on hydrobiont tissues . The different percentage of inhibition indicates the tissue specificity of 1 : the maximum reduction of TBARS concentration was observed in the case of heart homogenate.…”

Section: Resultssupporting

confidence: 75%

“…Potentially produced metabolites are able to promote the LP process. Earlier we confirmed in experiments in vitro that organometallic derivatives – Ph 3 Sb, Ph 3 SbBr 2 – promote theprocess of LP . Antimony(V) compounds in biosystems can undergo reduction to Sb(III) in interaction with low‐molecular‐weight thiols (cysteine, glutathione) and SH protein groups, resulting in ROS induction and intensifying the LP process.…”

Section: Resultssupporting

confidence: 68%

“…Compound 1 combines in its structure a hydrophobic organometallic fragment with a redox‐active ligand capable to exist in several redox forms. Organometallic antimony(V) derivatives with redox‐active ligands have been found to manifest antiradical activity …”

Section: Introductionmentioning

confidence: 99%

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The influence of triphenylantimony(V) catecholate and its spiroendoperoxide on lipid peroxidation

Smolyaninov

Antonova

Poddel’sky

et al. 2014

Applied Organom Chemis

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The effects of triphenylantimony(V) catecholate Ph 3 Sb(Cat) (1) and its spiroendoperoxide Ph 3 Sb(L-O 2 ) (2) (Cat = 3,6-di-tert-butyl-4,5-dimethoxycatecholate) on lipid peroxidation (LP) in vitro and in vivo were examined in BALB/c line mice. A comparative study of the impact of compounds 1 and 2 on LP under similar conditions was made by measuring the formation of thiobarbituric acid reactive substances (TBARS). The anti-or pro-oxidant action of complexes 1 and 2 may be caused by the different redox level of the ligand acting as radical scavenger and/or by the bound molecular oxygen promoting the oxidation process. Biological experiments (in vitro and in vivo) were performed using mouse tissue homogenates. Decreasing TBARS concentration was observed in all examined tissues and blood serum (in vitro as well as in vivo) for catecholate 1. These results indicate inhibition of LP in the presence of complex 1. In contrast to 1, spiroendoperoxide 2 increases the level of TBARS in tissue homogenates. Minor fluctuations of TBARS concentration in erythrocytes and in blood serum indicate the absence of an obvious anti/pro-oxidant influence of 2 on the LP process in vivo. The role of catecholate fragment was found to be essential in explaining antioxidant properties.

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Section: Resultssupporting

confidence: 75%

Section: Resultssupporting

confidence: 68%

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The influence of triphenylantimony(V) catecholate and its spiroendoperoxide on lipid peroxidation

Smolyaninov

Antonova

Poddel’sky

et al. 2014

Applied Organom Chemis

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“…4, 5 The biolog ical activity of these compounds has been studied. [6][7][8] Antimony compounds are characterized by a diversity of coordination modes and structure types. In the absence of strong steric hindrance, pentacoordinate Sb V deriva tives are prone to complete the coordination number to six through intermolecular interactions or through the coor dination by additional neutral ligands.…”

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confidence: 99%

Complex of triphenylantimony(v) catecholate with 5-(2,6-dimethylphenyl)-3-(4-pyridyl)-1-phenylformazan

et al. 2014

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The complex of triphenylantimony(V) 3,6 di tert butylcatecholate with 5 (2,6 dimethyl phenyl) 3 (4 pyridyl) 1 phenylformazan was synthesized and characterized by spectroscopic and electrochemical methods and by X ray diffraction. In the crystal structure, there are inter molecular hydrogen bonds between the formazan ligands of adjacent molecules. The electro chemical transformations of the complex were investigated by cyclic voltammetry. It was shown that both the formazan and catecholate moieties are involved in redox processes.

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“…Previously we showed that the redox characteristics, antiradical activity of organo-antimony(V) complexes with redox-active ligands, as well as their ability to bind molecular oxygen depends on a variety of factors [1][2][3][4][5][6]. Electron-donating substituent group in the redox-active fragment facilitates O 2 binding, shifts anodic oxidation potentials to the cathodic region, and enhances the antiradical activity of Sb(V) compounds [7,8].…”

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Redox transformations and antiradical activity of triarylantimony(V) 3,6-di-tert-butyl-4,5-dimethoxycatecholates

et al. 2014

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Triarylantimony(V) catecholate complexes were synthesized by the oxidative addition of 3,6-ditert-butyl-4,5-dimethoxy-o-benzoquinone to triarylstibines. The electrochemical properties and antiradical activity of the synthesized compounds were studied. According to cyclic viltammetry data, the complexes are oxidized via two consecutive quasi-reversible stages. Introduction of halogen atoms in para-position of phenyl groups at Sb(V) causes anodic shifts of the oxidation potentials and enhances stability of the mono-and dicationic forms of the compounds, which form in the course of electrochemical transformations. Triarylantimony(V) catecholate complexes exhibit appreciable antiradical activity in the auto-oxidation of oleic acid. In was found that the inhibitory activity of the complexes depends on their redox potential.Previously we showed that the redox characteristics, antiradical activity of organo-antimony(V) complexes with redox-active ligands, as well as their ability to bind molecular oxygen depends on a variety of factors [1-6]. Electron-donating substituent group in the redox-active fragment facilitates O 2 binding, shifts anodic oxidation potentials to the cathodic region, and enhances the antiradical activity of Sb(V) compounds [7,8]. Electron withdrawing groups in the catecholate ligand increase the potentials of the catecholate-о-semiquinolate-о-benzoquinone redox transitions and sometimes alter the mechanism of electrochemical oxidation of triphenylantimony(V) catecholate complexes from a two-stage one-electron transfer to one-stage two-electron transfer process [9, 10]. The stability of the cationic complexes resulting from electrochemical oxidation is also affected by the nature of the heteroatoms forming five-membered N, O,Oor S,. The properties of Sb(V) catecholate complexes can also be varied not only by varying substituents in the redox-active ligand, but also by functionalizing groups linked to the central antimony atom [15]. In the present work we continued to study the effect of aryl substituents (phenyl, pchlorophenyl, p-fluorophenyl) in the organometallic fragment SbR 3 of triarylantimony(V) 3,6-di-tert-butyl-4,5-dimethoxycatecholate complexes on the electrochemical transformations and antiradical activity in the auto-oxidation of oleic acid.We have synthesized triphenylantimony, tri-pchlorophenyl-, and tri-p-chlorophenylantimony catecholate complexes I-III by the oxidative addition of the corresponding triarylstibines to 3,6-di-tert-butyl-4,5-dimethoxy-о-benzoquinone (Scheme 1).Complex I was described in [5]. Complexes II and III were characterized by 1 H and 13 C NMR spectroscopy and mass spectrometry; their structure was found to be consistent with the suggested formulas. The oxidation potential relates to the reducing ability of a compound and is a factor which allows one to predict the antiradical activity. The electrochemical

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The influence of some triphenylantimony(V) catecholates and o‐amidophenolates on lipid peroxidationin vitro

Cited by 26 publications

References 61 publications

The influence of triphenylantimony(V) catecholate and its spiroendoperoxide on lipid peroxidation

The influence of triphenylantimony(V) catecholate and its spiroendoperoxide on lipid peroxidation

Complex of triphenylantimony(v) catecholate with 5-(2,6-dimethylphenyl)-3-(4-pyridyl)-1-phenylformazan

Redox transformations and antiradical activity of triarylantimony(V) 3,6-di-tert-butyl-4,5-dimethoxycatecholates

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