1-(2-(2-(2-(1-Aminoethyl)phenyl)diselanyl)phenyl)ethanamine: An amino organoselenium compound with interesting antioxidant profile

Free radical scavenging and antioxidant activities of 1-(2-(2-(2-(1-aminoethyl)phenyl)diselanyl)phenyl)ethanamine (compound A) and diphenyl diselenide (PhSe)2 were examined and compared for inhibition of Fe(II) and sodium nitroprusside (SNP) stimulated lipid peroxidation in rat brain, interaction with 1,1-diphenyl-2-picrylhydrazyl (DPPH) stable free radical and their glutathione peroxidase (GPx) like antioxidant activities with H₂O₂ or tBuOOH as substrates and with PhSH as thiol co-substrates as well as their ability to oxidize mono- and di-thiols were also evaluated. This study revealed that an amino group in amino diselenide drastically enhances their catalytic activities in the aromatic thiol (PhSH) assay system. Compound A was ～2-fold more active than (PhSe)2 in both tBuOOH and H₂O₂ assay systems. In addition, the present results showed that (PhSe)2 exhibited an increased ability to oxidize di-thiols, compound A was not a good substrate for the oxidation of thiol used namely DTT, cystine and DMPS. The antioxidant potency against Fe(II) and SNP-induced brain TBARS were in this order (compound A); IC₅₀ 2 μM and 4 μM] > (PhSe)2; IC₅₀ 19 μM and 27.5 μM. Compound A showed DPPH radical-scavenging activity. This study provides in vitro evidence anti-oxidant action of the tested organoselenium compounds, that the nitrogen atom in the organochalcogens can have a profound effect on their antioxidant activity.