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García-España, A.
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article
Homo- and Heterobinuclear Cu<sup>2+</sup> and Zn<sup>2+</sup> Complexes of Ditopic Aza Scorpiand Ligands as Superoxide Dismutase Mimics.
Abstract
Two polytopic aza-scorpiand-like ligands, 6-[7-(diaminoethyl)-3,7-diazaheptyl]-3,6,9-triaza-1-(2,6-pyridina)cyclodecaphane (L1) and 6-[6'-[3,6,9-triaza-1-(2,6-pyridina)cyclodecaphan-6-yl]-3-azahexyl]-3,6,9-triaza-1-(2,6-pyridina)cyclodecaphane (L2), have been synthesized. The acid-base behavior and Cu<sup>2+</sup>, Zn<sup>2+</sup>, and Cu<sup>2+</sup>/Zn<sup>2+</sup> mixed coordination have been analyzed by potentiometry, cyclic voltammetry, and UV-vis spectroscopy. The resolution of the crystal structures of [Cu<sub>2</sub>L2Cl<sub>2</sub>](ClO<sub>4</sub>)<sub>2</sub>·1.67H<sub>2</sub>O (1), [Cu<sub>2</sub>HL2Br<sub>2</sub>](ClO<sub>4</sub>)<sub>3</sub>·1.5H<sub>2</sub>O (2), and [CuZnL2Cl<sub>2</sub>](ClO<sub>4</sub>)<sub>2</sub>·1.64H<sub>2</sub>O (3) shows, in agreement with the solution data, the formation of homobinuclear Cu<sup>2+</sup>/Cu<sup>2+</sup> and heterobinuclear Cu<sup>2+</sup>/Zn<sup>2+</sup> complexes. The metal ions are coordinated within the two macrocyclic cavities of the ligand with the involvement of a secondary amino group of the bridge in the case of 1 and 3. Energy-dispersive X-ray spectroscopy confirms the 1:1 Cu<sup>2+</sup>/Zn<sup>2+</sup> stoichiometry of 3. The superoxide dismutase (SOD) activities of the Cu<sup>2+</sup>/Cu<sup>2+</sup> and Cu<sup>2+</sup>/Zn<sup>2+</sup> complexes of L1 and L2 have been evaluated using nitro blue tetrazolium assays at pH 7.4. The IC<sub>50</sub> and k<sub>cat</sub> values obtained for the [Cu<sub>2</sub>L1]<sup>4+</sup> complex rank among the best values reported in the literature for Cu-SOD mimics. Interestingly, the binuclear Cu<sup>2+</sup> complexes of L1 and L2 have low toxicity in cultures of mammalian cell lines and show significant antioxidant activity in a copper-dependent SOD (SOD1)-defective yeast model. The results are rationalized by taking into account the binding modes of the Cu<sup>2+</sup> ions in the different complexes.