期刊
INORGANIC CHEMISTRY
卷 55, 期 15, 页码 7564-7575出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.inorgchem.6b01006
关键词
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资金
- Spanish Ministerio de Economia y Competitividad [CSD-2010-00065, CTQ2013-48917-C3-1-P, MDM 2015-0038]
- Generalitat Valenciana [PROMETEOII2015-002]
- CONACYT
- Red Tematica de Quimica Supramolecular [271884]
- Secretaria de Educacion Publica, Mexico [P/PIFI 2014]
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 mu g/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.
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