Benzylamine antioxidants: relationship between structure, peroxyl radical scavenging, lipid peroxidation inhibition and cytoprotection

摘要: Three homologous series of 3,5-dialkoxy-4-hydroxybenzylamines were prepared and tested (1) as peroxyl radical scavengers in homogeneous aqueous solution, (2) inhibitors iron-dependent peroxidation rabbit brain vesicular membrane lipids, (3) cytoprotective agents using primary cultures rat hippocampal neurons exposed to hydrogen peroxide. The structural requirements for efficient trapping solution differed from those effective lipid inhibition: In a kinetic preference existed smaller, less sterically encumbered substituents flanking the reactive phenolic hydroxyl group. Lipid inhibition, on other hand, required longer more lipophilic substituents. Consequently, alkoxyl substituent at C3 small C5 appeared optimal scavenging activity both solution. Maximal cytoprotection peroxide was also associated with derivatives although length bulk may represent independent parameters relating structure efficacy this system.