This study represents an integrated approach towards understanding the electronic and structural aspects of 2-benzylamino-1,4-naphthalenedione, a representative 2-amino-napfthoquinone. To this end, theoretical calculations performed at the B3PW91/6-31+G(d) level of density functional theory, electrochemical and X-ray structural investigation were employed. Two intramolecular H-bonds and other two intermolecular H-bonds were observed, including non-classical interactions. Cyclic voltammogram (CV) and differential pulse voltammetry (DPV) show two pairs of peaks, being each one a monoelectronic process.

Since the biological activity of [RuIII(NH3)4(catechol)]+ has never been tested, its cytotoxicity to glial cells was assayed and correlated with its redox properties. Coordinated catechol oxidizes faster than catechol in the presence of oxygen, but controlled potential electrolysis showed that its oxidation involves only one-electron. However, the oxidation of the free ligand by oxygen involves two electrons, which could generate more reactive oxygen species. Indeed, catechol was more cytotoxic than [RuIII(NH3)4(catechol)]+ complex to human glioblastoma GL-15 cells and also to rat astrocytes. [RuIII(NH3)4(catechol)]+-induced cytotoxicity was related to the generation of reactive oxygen species and [RuC1(NH3)5]2+. However, other mechanisms should be involved since antioxidant enzymes and deferoxamine only partially protected GL-15 cells