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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

Scavenging activity for compounds 1–6 in DPPH test (MeOH, 20°C, 100 μM).
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fig2: Scavenging activity for compounds 1–6 in DPPH test (MeOH, 20°C, 100 μM).

Mentions: The scavenging activity has been studied in the process of hydrogen atom transfer to the stable free radical DPPH [22]. The results of DPPH test at 20°C show that the activity depends strongly upon the presence of phenolic group in the presented pairs of compounds. The activity of 1, for instance, was 88.4% that is higher than that of a known antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT) (48.5%) whereas the activity of 2 bearing phenyl substituent was almost negligible −2.9% (Figure 2). The values of scavenging activity of compounds 3, 5 were lower, and in the case of 3 the decrease in activity was more pronounced. Evidently the activity extent of the compounds tested depends on their molecular structures. The HO-group of 2,6-di-tert-butylphenol is the key site in the molecule that is involved in hydrogen transfer to DPPH. However, despite the presence of ferrocene moiety in all the compounds they differ significantly containing linkers of various length and conjugation ability (–CH=N–, 1; –CH=N–CH2–, 2; –CH=CH–C(O)–, 3). The decrease of conjugation in their molecules containing either CH2 or CO groups in linkers leads to the decrease of metal influence on the stability of radicals formed as it has been observed previously [6]. However, it should be mentioned that the activity of 3 is much higher than that of 5 with N atom possessing a lone electron pair in linker that improves the influence of ferrocene moiety.


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)

Scavenging activity for compounds 1–6 in DPPH test (MeOH, 20°C, 100 μM).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig2: Scavenging activity for compounds 1–6 in DPPH test (MeOH, 20°C, 100 μM).
Mentions: The scavenging activity has been studied in the process of hydrogen atom transfer to the stable free radical DPPH [22]. The results of DPPH test at 20°C show that the activity depends strongly upon the presence of phenolic group in the presented pairs of compounds. The activity of 1, for instance, was 88.4% that is higher than that of a known antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT) (48.5%) whereas the activity of 2 bearing phenyl substituent was almost negligible −2.9% (Figure 2). The values of scavenging activity of compounds 3, 5 were lower, and in the case of 3 the decrease in activity was more pronounced. Evidently the activity extent of the compounds tested depends on their molecular structures. The HO-group of 2,6-di-tert-butylphenol is the key site in the molecule that is involved in hydrogen transfer to DPPH. However, despite the presence of ferrocene moiety in all the compounds they differ significantly containing linkers of various length and conjugation ability (–CH=N–, 1; –CH=N–CH2–, 2; –CH=CH–C(O)–, 3). The decrease of conjugation in their molecules containing either CH2 or CO groups in linkers leads to the decrease of metal influence on the stability of radicals formed as it has been observed previously [6]. However, it should be mentioned that the activity of 3 is much higher than that of 5 with N atom possessing a lone electron pair in linker that improves the influence of ferrocene moiety.

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