Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol Moieties
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 mitochondr...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2010-01-01
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| Series: | Bioinorganic Chemistry and Applications |
| Online Access: | http://dx.doi.org/10.1155/2010/165482 |
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| author | E. R. Milaeva S. I. Filimonova N. N. Meleshonkova L. G. Dubova E. F. Shevtsova S. O. Bachurin N. S. Zefirov |
| author_facet | E. R. Milaeva S. I. Filimonova N. N. Meleshonkova L. G. Dubova E. F. Shevtsova S. O. Bachurin N. S. Zefirov |
| author_sort | E. R. Milaeva |
| collection | DOAJ |
| description | 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∘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. |
| format | Article |
| id | doaj-art-33186562b19042d78995ef41db4a07a2 |
| institution | Kabale University |
| issn | 1565-3633 1687-479X |
| language | English |
| publishDate | 2010-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Bioinorganic Chemistry and Applications |
| spelling | doaj-art-33186562b19042d78995ef41db4a07a22025-02-03T01:28:56ZengWileyBioinorganic Chemistry and Applications1565-36331687-479X2010-01-01201010.1155/2010/165482165482Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol MoietiesE. R. Milaeva0S. I. Filimonova1N. N. Meleshonkova2L. G. Dubova3E. F. Shevtsova4S. O. Bachurin5N. S. Zefirov6Organic Chemistry Department, M.V. Lomonosov Moscow State University, 119991, Moscow, RussiaOrganic Chemistry Department, M.V. Lomonosov Moscow State University, 119991, Moscow, RussiaOrganic Chemistry Department, M.V. Lomonosov Moscow State University, 119991, Moscow, RussiaInstitute of Physiologically Active Compounds, Russian Academy of Sciences, 142432, Chernogolovka, RussiaInstitute of Physiologically Active Compounds, Russian Academy of Sciences, 142432, Chernogolovka, RussiaInstitute of Physiologically Active Compounds, Russian Academy of Sciences, 142432, Chernogolovka, RussiaOrganic Chemistry Department, M.V. Lomonosov Moscow State University, 119991, Moscow, RussiaThe 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∘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.http://dx.doi.org/10.1155/2010/165482 |
| spellingShingle | E. R. Milaeva S. I. Filimonova N. N. Meleshonkova L. G. Dubova E. F. Shevtsova S. O. Bachurin N. S. Zefirov Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol Moieties Bioinorganic Chemistry and Applications |
| title | Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol Moieties |
| title_full | Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol Moieties |
| title_fullStr | Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol Moieties |
| title_full_unstemmed | Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol Moieties |
| title_short | Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol Moieties |
| title_sort | antioxidative activity of ferrocenes bearing 2 6 di tert butylphenol moieties |
| url | http://dx.doi.org/10.1155/2010/165482 |
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