Dependence of the cytotoxicity and antioxidant activity of the ammonium derivatives of alkylphenols on their structural characteristics

Abstract

The influence of seven structurally similar N,N-dimethyl-(4-hydroxyaryl)alkylammonium chlorides on the survival of strains of E. coli cells has been studied. AB1157 and isogenic BH910 defective in the genes of repair enzymes have been analyzed in the presence and in the absence of hydrogen peroxide. Among the studied compounds, only N,N-dimethyl-(3,5-dimethyl-4-hydroxybenzyl)ammonium chloride (C1) did not show cytotoxic properties and increased the survival of the cells of both strains in the presence of H2O2 to a larger extent than trolox (water-soluble analogue of α-tocopherol). Analogues of C1, derivatives of 3-methyl-5-di-tert-butyl-4-hydroxybenzyl- and 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propylamines, efficiently protected only mutant BH910 cells against H2O2. In a series of structural analogues of C1, the cytotoxicity increased with the replacement of the methyl groups in the aromatic ring by tert-butyl and cyclohexyl groups. Among the seven new compounds, only the C1 derivative is a prospective antioxidant for a subsequent more detailed analysis.