A new synthetic pathway was reported to obtain N6 donor ligand 2,9-bis-(2',5'-diazahexanyl)-1,10-phenanthroline (L1) and its coordination compounds of essential divalent metal ions Mn, Fe, Co, Ni, Cu and Zn. Complete characterization of all compounds was done with the conventional techniques. Crystal structures of [NiL1](PF(6))(2) and [ZnL1](PF(6))(2)·H(2)O were also reported. Electrochemical studies have shown an active participation of the aromatic moiety of the ligand in redox reactions. The in vitro tests of the cytotoxic activity against human tumour cell lines HeLa (cervix) and CHP-212 (neuroblastoma) showed that all coordination compounds that involve redox active metal ions exhibit noteworthy antiproliferative activity, superior in all cases to cisplatin. [CuL1](2+) showed the lower IC(50) value in the HeLa cell line with 1.84 μM, meanwhile, [CoL1](2+) showed the lower value in neuroblastoma CHP-212 with IC(50) = 45.28 μM. None of these compounds were active against the SK-N-SH neuroblastoma cell line. In Entamoeba histolytica cultures, remarkable nanomolar IC(50) values were found for [NiL1](2+) and [MnL1](2+) with 60 nM and 80 nM respectively, improving the antiproliferative activity more than 1000 times compared with the first choice drug for clinical treatments of human amoebiasis, metronidazole. On the other hand, a free ligand does not show antiproliferative activity either on human tumor cell lines or on Entamoeba histolytica trophozoites, highlighting the role played by metal ions to produce cytotoxicity in tumor cells and protozoa systems.
The spontaneous decomposition of 4‐nitrophenyldiazonium tetrafluoroborate in acetonitrile solution was used to modify glassy carbon electrodes with films bearing nitrophenyl groups. The modification procedure was performed by dipping non‐connected electrodes into the nitrophenyldiazonium solution. When these modified electrodes were analyzed by cyclic voltammetry in acetonitrile containing traces of water over a wide potential scale, only one reduction wave and two oxidation peaks were observed, which is atypical considering the reversible behaviour of the reduction of nitrobenzene in acetonitrile, however in acetonitrile containing a lower concentration of water, two consecutive reduction waves appear in the same potential scale. The difference between both behaviours is consistent with the presence of water trapped into the film structure, which promotes electron and proton transfer reactions that yield nitrosobenzene as product in surface. The trapping of water inside the film structure is justified by the capability of the nitrophenyl groups to interact with water by surface hydrogen bonding interactions.
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