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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

The relative content of TBARS in the lipid peroxidation of rat brain homogenates as nonenzymatic process in the presence of 10 μM 1–6 (0.5 mM Fe(NH4)(SO4)2).
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fig3: The relative content of TBARS in the lipid peroxidation of rat brain homogenates as nonenzymatic process in the presence of 10 μM 1–6 (0.5 mM Fe(NH4)(SO4)2).

Mentions: The data of antioxidative activity assay of 1–6 presenting the pairs of compounds bearing either 3,5-di-tert-butyl-4-hydroxyphenyl or phenyl substituents linked to the ferrocene by various spacers are shown in Figure 3. The IC50 values are summarized in Table 1.


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)

The relative content of TBARS in the lipid peroxidation of rat brain homogenates as nonenzymatic process in the presence of 10 μM 1–6 (0.5 mM Fe(NH4)(SO4)2).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig3: The relative content of TBARS in the lipid peroxidation of rat brain homogenates as nonenzymatic process in the presence of 10 μM 1–6 (0.5 mM Fe(NH4)(SO4)2).
Mentions: The data of antioxidative activity assay of 1–6 presenting the pairs of compounds bearing either 3,5-di-tert-butyl-4-hydroxyphenyl or phenyl substituents linked to the ferrocene by various spacers are shown in Figure 3. The IC50 values are summarized in Table 1.

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