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Bioinorganic Chemistry and Applications
Volume 2010, Article ID 165482, 6 pages
http://dx.doi.org/10.1155/2010/165482
Research Article

Antioxidative Activity of Ferrocenes Bearing 2,6-Di-Tert-Butylphenol Moieties

1Organic Chemistry Department, M.V. Lomonosov Moscow State University, 119991, Moscow, Russia
2Institute of Physiologically Active Compounds, Russian Academy of Sciences, 142432, Chernogolovka, Russia

Received 28 December 2009; Accepted 30 March 2010

Academic Editor: Spyros Perlepes

Copyright © 2010 E. R. Milaeva et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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 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.