Spectral and electrochemical studies of ruthenium(II) complexes with N4-methyl-4-nitrobenzaldehyde and N4-methyl-4-nitrobenzophenone thiosemicarbazone: Potential anti-trypanosomal agents

N4-Methyl-4-nitrobenzaldehyde thiosemicarbazone (H4NO2Fo4M), N4-methyl-4-nitrobenzophenone thiosemicarbazone (H4NO2Bz4M) and their ruthenium(II) complexes [Ru(4NO2Fo4M)2(PPh3)2] (1), [Ru(4NO2Bz4M)2(PPh3)2] (2), [Ru(4NO2Fo4M)2(dppb)] (3) and [Ru(4NO2Bz4M)2(dppb)] (4) (dppb = 1,4-bis(diphenylphospine)butane) were obtained and characterized. The crystal structure of H4NO2Fo4M has been determined. Electrochemical studies have shown that the nitro anion radical, one of the proposed intermediates in the mechanism of action of nitro-containing anti-trypanosomal drugs, is formed at approximately −1.00 V in the free thiosemicarbazones as well as in their corresponding ruthenium(II) complexes, suggesting their potential to act as antitrypanosomal drugs. The natural fluorescence of H4NO2Fo4M, H4NO2Bz4M and complexes (1)–(4) provides a way to identify and to monitor their concentration in biological systems.

N4-Methyl-4-nitrobenzaldehyde thiosemicarbazone (H4NO2Fo4M), N4-methyl-4-nitrobenzophenone thiosemicarbazone (H4NO2Bz4M) and their ruthenium(II) complexes [Ru(4NO2Fo4M)2(PPh3)2] (1), [Ru(4NO2Bz4M)2(PPh3)2] (2), [Ru(4NO2Fo4M)2(dppb)] (3) and [Ru(4NO2Bz4M)2(dppb)] (4) were obtained. The nitro anion radical, one of the proposed intermediates in the mechanism of action of nitro-containing anti-trypanosomal drugs, is formed at approximately −1.00 V in the free thiosemicarbazones as well as in their corresponding ruthenium(II) complexes, suggesting their potential to act as antitrypanosomal drugs. The natural fluorescence of H4NO2Fo4M, H4NO2Bz4M and complexes (1)–(4) provides a way to identify and to monitor their concentration in biological systems.Figure optionsDownload as PowerPoint slide