Four new hydrazones were synthesized by the condensation of the selected hydrazine and the appropriate nitrobenzaldehyde. A complete characterization was done employing 1 H-and 13 C-NMR, electrochemical techniques and theoretical studies. After the characterization and electrochemical analysis of each compound, amoebicidal activity was tested in vitro against the HM1:IMSS strain of Entamoeba histolytica. The results showed the influence of the nitrobenzene group and the hydrazone linkage on the amoebicidal activity. meta-Nitro substituted compound 2 presents a promising amoebicidal activity with an IC50 = 0.84 μM, which represents a 7-fold increase in cell growth inhibition potency with respect to metronidazole (IC50 = 6.3 μM). Compounds 1, 3, and 4 show decreased amoebicidal activity, with IC50 values of 7, 75 and 23 µM, respectively, as a function of the nitro group position on the aromatic ring. The observed differences in the biological activity could be explained not only by the redox potential of the molecules, but also by their capacity to participate in the formation of intra-and intermolecular hydrogen bonds. Redox potentials as well as the amoebicidal activity can be described with parameters obtained from the DFT analysis.
This work presents the electrochemical characterization of Cu(NO<sub>3</sub>)<sub>2</sub>•2.5H<sub>2</sub>O, [Cu(pdto)H<sub>2</sub>O](PF6)<sub>2</sub> and superoxide ion in DMSO. The electrochemical processes Cu(II) + 2e → Cu(0), [Cu(pdto)(H<sub>2</sub>O)]<sup>2+</sup> + 1e → [Cu(pdto)]<sup>+</sup>, [Cu(pdto)]<sup>+</sup> + 1e → Cu(0), O<sub>2</sub> <sup>•-</sup> ↔ O<sub>2</sub> + 1e-, and O<sub>2</sub><sup>•-</sup> + 1e + H+ → OOH<sup>-</sup> were identified. The electrochemical response of a mixture of the complex [Cu(pdto)(H<sub>2</sub>O)]<sup>2+</sup> with superoxide was studied and, according to this result, it was possible to establish a simple methodology that indicates if a compound presents a superoxide dismutase (SOD)-like mechanism.
In the title compound, [Cu(C16H20N2S2)(H2O)](NO3)2·CH3CN, the CuII atom displays a distorted square-pyramidal coordination, in which a water molecule occupies the apical position and the basal plane is formed by two N atoms and two S atoms of a 1,8-bis(pyridin-2-yl)-3,6-dithiaoctane ligand. The crystal packing is stabilized by O—H⋯O and C—H⋯O hydrogen bonds.
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