Novel iron complexes behave like superoxide dismutase in vivo

Novel iron and copper complexes having tris[N-(5-methyl-2-pyridylmethyl)-2-aminoethyl]amine (5MeT-PAA), tris[N-(3-methyl-2-pyridylmethyl)-2-aminoethyl]amine (3MeTPAA), tris[N-(5-methoxycarbonyl-2-pyridylmethyl)-2-aminoethyl]amine (TNAA), tris[(2-thienylmethyl)-2-aminoethyl]amine (TTAA), tris[(2-furylmethyl)-2-aminoethyl]amine (TFAA) or tris[(2-imidazoyl)-2-aminoethyl]amine (TIAA) as ligand, were synthesized to examine the superoxide dismutase (SOD) activity. The concentrations of Fe-3MeTPAA and Fe-TIAA equivalent to 1 unit of SOD (IC50) were 0.5 microM and 1.0 microM, respectively. Fe-3MeTPAA and Fe-TIAA had higher SOD activity than other Fe and Cu complexes and protected Escherichia coli cells from paraquat toxicity. In case of using tris[N-(6-methyl-2-pyridylmethyl)-2-aminoethyl]amine (6MeTPAA) as ligand, the Fe complex could not be obtained, which may be due to the steric hindrance of 6-methyl substituent. Generally, Cu complexes had low SOD activity, compared with Fe complexes, and could not suppress paraquat toxicity.