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Antioxidative activity of ferrocenes bearing 2,6-di-tert-butylphenol moieties.

Milaeva ER, Filimonova SI, Meleshonkova NN, Dubova LG, Shevtsova EF, Bachurin SO, Zefirov NS - Bioinorg Chem Appl (2010)

Bottom Line: The results of DPPH test at 20 degrees C show that the activity depends strongly upon the presence of phenolic group but is improved by the influence of ferrocenyl fragment.The data obtained demonstrate that the compounds with 2,6-di-tert-butylphenol moiety are significantly more active than the corresponding phenyl analogues in the in vitro study of lipid peroxidation in rat brain homogenate.These results allow us to propose the potential cytoprotective (neuroprotective) effect of ditopic compounds containing antioxidant 2,6-di-tert-butylphenol group and redox active ferrocene fragment.

View Article: PubMed Central - PubMed

Affiliation: Organic Chemistry Department, M.V. Lomonosov Moscow State University, 119991, Moscow, Russia.

ABSTRACT
The antioxidative activity of ferrocenes bearing either 2,6-di-tert-butylphenol or phenyl groups has been compared using DPPH (1,1-diphenyl-2-picrylhydrazyl) test and in the study of the in vitro impact on lipid peroxidation in rat brain homogenate and on some characteristics of rat liver mitochondria. The results of DPPH test at 20 degrees C show that the activity depends strongly upon the presence of phenolic group but is improved by the influence of ferrocenyl fragment. The activity of N-(3,5-di-tert-butyl-4-hydroxyphenyl)iminomethylferrocene (1), for instance, was 88.4%, which was higher than the activity of a known antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT) (48.5%), whereas the activity of N-phenyl-iminomethylferrocene 2 was almost negligible -2.9%. The data obtained demonstrate that the compounds with 2,6-di-tert-butylphenol moiety are significantly more active than the corresponding phenyl analogues in the in vitro study of lipid peroxidation in rat brain homogenate. Ferrocene 1 performs a promising behavior as an antioxidant and inhibits the calcium-dependent swelling of mitochondria. These results allow us to propose the potential cytoprotective (neuroprotective) effect of ditopic compounds containing antioxidant 2,6-di-tert-butylphenol group and redox active ferrocene fragment.

No MeSH data available.


Related in: MedlinePlus

Influence of 0.1 mM ferrocenes 1 and 2 on mitochondrial swelling and transmembrane potential (the values were determined and expressed as % of control).
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fig4: Influence of 0.1 mM ferrocenes 1 and 2 on mitochondrial swelling and transmembrane potential (the values were determined and expressed as % of control).

Mentions: It was shown that at concentration 0.1 mM ferrocenes 1 and 2 slightly depolarize the mitochondria (up to 25%) (Figure 4). On the other hand, these compounds inhibit the calcium-dependent swelling of mitochondria and this effect could not be the consequence of the depolarisation only. In both cases the effects on mitochondrial swelling and mitochondrial membrane potential obtained for ferrocene 1 are less pronounced that for 2. These data allow us to propose the potential cytoprotective (neuroprotective) effect of compounds studied.


Antioxidative activity of ferrocenes bearing 2,6-di-tert-butylphenol moieties.

Milaeva ER, Filimonova SI, Meleshonkova NN, Dubova LG, Shevtsova EF, Bachurin SO, Zefirov NS - Bioinorg Chem Appl (2010)

Influence of 0.1 mM ferrocenes 1 and 2 on mitochondrial swelling and transmembrane potential (the values were determined and expressed as % of control).
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC2901619&req=5

fig4: Influence of 0.1 mM ferrocenes 1 and 2 on mitochondrial swelling and transmembrane potential (the values were determined and expressed as % of control).
Mentions: It was shown that at concentration 0.1 mM ferrocenes 1 and 2 slightly depolarize the mitochondria (up to 25%) (Figure 4). On the other hand, these compounds inhibit the calcium-dependent swelling of mitochondria and this effect could not be the consequence of the depolarisation only. In both cases the effects on mitochondrial swelling and mitochondrial membrane potential obtained for ferrocene 1 are less pronounced that for 2. These data allow us to propose the potential cytoprotective (neuroprotective) effect of compounds studied.

Bottom Line: The results of DPPH test at 20 degrees C show that the activity depends strongly upon the presence of phenolic group but is improved by the influence of ferrocenyl fragment.The data obtained demonstrate that the compounds with 2,6-di-tert-butylphenol moiety are significantly more active than the corresponding phenyl analogues in the in vitro study of lipid peroxidation in rat brain homogenate.These results allow us to propose the potential cytoprotective (neuroprotective) effect of ditopic compounds containing antioxidant 2,6-di-tert-butylphenol group and redox active ferrocene fragment.

View Article: PubMed Central - PubMed

Affiliation: Organic Chemistry Department, M.V. Lomonosov Moscow State University, 119991, Moscow, Russia.

ABSTRACT
The antioxidative activity of ferrocenes bearing either 2,6-di-tert-butylphenol or phenyl groups has been compared using DPPH (1,1-diphenyl-2-picrylhydrazyl) test and in the study of the in vitro impact on lipid peroxidation in rat brain homogenate and on some characteristics of rat liver mitochondria. The results of DPPH test at 20 degrees C show that the activity depends strongly upon the presence of phenolic group but is improved by the influence of ferrocenyl fragment. The activity of N-(3,5-di-tert-butyl-4-hydroxyphenyl)iminomethylferrocene (1), for instance, was 88.4%, which was higher than the activity of a known antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT) (48.5%), whereas the activity of N-phenyl-iminomethylferrocene 2 was almost negligible -2.9%. The data obtained demonstrate that the compounds with 2,6-di-tert-butylphenol moiety are significantly more active than the corresponding phenyl analogues in the in vitro study of lipid peroxidation in rat brain homogenate. Ferrocene 1 performs a promising behavior as an antioxidant and inhibits the calcium-dependent swelling of mitochondria. These results allow us to propose the potential cytoprotective (neuroprotective) effect of ditopic compounds containing antioxidant 2,6-di-tert-butylphenol group and redox active ferrocene fragment.

No MeSH data available.


Related in: MedlinePlus