Synthesis, Characterization, and Cu2+ Coordination Studies of a 3-Hydroxy-4-pyridinone Aza Scorpiand Derivative

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• 作者：Luis M. López-Martínez ; Javier Pitarch-Jarque ; Àlvar Martínez-Camarena ; Enrique García-España ; Roberto Tejero ; Hisila Santacruz-Ortega ; Rosa-Elena Navarro ; Rogerio R. Sotelo-Mundo ; Mario Alberto Leyva-Peralta ; Antonio Doménech-Carbó ; Begoña Verdejo
• 刊名：Inorganic Chemistry
• 出版年：2016
• 出版时间：August 1, 2016
• 年：2016
• 卷：55
• 期：15
• 页码：7564-7575
• 全文大小：671K
• 年卷期：0
• ISSN：1520-510X

文摘

The synthesis, acid–base behavior, and Cu²⁺ coordination chemistry of a new ligand (L1) consisting of an azamacrocyclic core appended with a lateral chain containing a 3-hydroxy-2-methyl-4(1H)-pyridinone group have been studied by potentiometry, cyclic voltammetry, and NMR and UV–vis spectroscopy. UV–vis and NMR studies showed that phenolate group was protonated at the highest pH values [log K = 9.72(1)]. Potentiometric studies point out the formation of Cu²⁺ complexes of 1:2, 2:2, 4:3, 1:1, and 2:1 Cu²⁺/L1 stoichiometries. UV–vis analysis and electrochemical studies evidence the implication of the pyridinone moieties in the metal coordination of the 1:2 Cu²⁺/L1 complexes. L1 shows a stronger chelating ability than the reference chelating ligand deferiprone. While L1 shows no cytotoxicity in HeLa and ARPE-19 human cell lines (3.1–25.0 μg/mL), it has significant antioxidant activity, as denoted by TEAC assays at physiological pH. The addition of Cu²⁺ diminishes the antioxidant activity because of its coordination to the pyridinone moiety phenolic group.