Antioxidant and antiglycating activities of 2,6-di- tert -butyl-4-[ N -(4-pyridyl)iminomethyl]phenol ( 1 ), 2,6-di- tert -butyl-4-[ N -(3-pyridylmethyl)-iminomethyl]phenol ( 2 ) and N -(3,5-di- tert -butyl-4-hydroxyphenyl)iminomethylferrocene ( 3 ) have been studied. Antioxidant activity of 2,6-di- tert -butylphenol bearing ferrocenyl moiety was shown to be sufficiently higher than that of the compounds 1 and 2 . Based on the data obtained in comparison with aminoguanidine which is an effective protein glycation inhibitor it was established that the introduction of ferrocenyl moiety into 2,6-di- tert -butylphenol results in a dramatic increase in the antiglycating activity exceeding that for aminoguanidine.
The effects of the complexes Cu(LRH)2(NO3)2 (R = H, Me) with the nitronylnitroxyl radicals LRH on the lipoxygenase (LOX-1) activity upon peroxidation of linoleic acid were studied. The complexes under study are reversible enzyme inhibitors, competitive and non-competitive inhibition type being observed for the complex with the methyl-substituted and unsubstituted ligands, respectively. The results of molecular docking showed that the complexes under study are incorporated into the hydrophobic pocket of the LOX-1 active site and the change in the type of inhibition can be explained by introduction of additional methyl group into the imidazole fragment of the ligand, which provides a slightly more favorable interaction of the inhibitor with the enzyme and results in the non-competitive mechanism of inhibition. The starting diamagnetic compounds (LRH2), nitronylnitroxyl radicals (LRH), and CuII complexes exhibit high activity in the nonenzymatic peroxidation of linoleic acid, as well as in generation of the superoxide radical anion O2 ·− in the xanthine-xanthine oxidase system.