Synthesis and antioxidative activity of metalloporphyrins bearing 2,6-di-tert-butylphenol pendants
| Autor: | Oscar I. Koifman, Elena F. Shevtsova, A.S. Semeykin, Elena R. Milaeva, E. G. Kireeva, Olga A. Gerasimova, D.B. Shpakovsky, Nikolay S. Zefirov, Sergey O. Bachurin, Sergei A. Syrbu, Zhang Jingwei |
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| Rok vydání: | 2007 |
| Předmět: |
Antioxidant
Stereochemistry Metalloporphyrins Radical medicine.medical_treatment Iron Palmitic Acids Biochemistry Medicinal chemistry Antioxidants Inorganic Chemistry Metal Lipid peroxidation chemistry.chemical_compound Phenols medicine Moiety Animals Rats Wistar 2 6-Di-tert-butylphenol chemistry.chemical_classification Manganese Chemistry Electron Spin Resonance Spectroscopy Cobalt Rats Oleic acid Zinc Hydrocarbon visual_art Mitochondrial Membranes visual_art.visual_art_medium Lipid Peroxidation Copper Oleic Acid |
| Zdroj: | Journal of inorganic biochemistry. 102(5-6) |
| ISSN: | 0162-0134 |
| Popis: | The novel metalloporphyrins (M = HH, Fe, Mn, Co, Cu, Zn) bearing 2,6-di- tert -butylphenol pendants as antioxidant substituents, and a long chain hydrocarbon palmitoyl group have been synthesized. The oxidation of compounds by PbO 2 leads to the formation of the corresponding 2,6-di- tert -butylphenoxyl radicals studied by EPR. The activity of porphyrins in lipid peroxidation has been examined using (1) in vitro lipid peroxidation induced by tert -butylhydroperoxide in respiring rat liver mitochondria, (2) in vitro lipid peroxidation in liver homogenates of Wistar strain rats, and (3) a model process of peroxidation of ( Z )-octadec-9-enic (oleic) acid as a structural fragment of lipids. The activity of these compounds depends dramatically on the nature of metal and might be changed from antioxidative (M = HH, Mn, Cu, Zn) to indifferent (M = Co), and to pro-oxidative one (M = Fe). The anti- or pro-oxidative action of these compounds may be derived from the concurrence between the involvement of 2,6-di- tert -butylphenol pendants acting as radical scavengers and redox active metal center promoting oxidation processes. The results of this study suggest that the polytopic compounds combining in one molecule 2,6-di- tert -butylphenol pendants, metalloporphyrin moiety, and a palmitoyl group, are membrane active compounds and might be studied in an effort to find novel pharmaceutical agents. |
| Databáze: | OpenAIRE |
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