title: Synthesis, Characterization, and Cu(2+) Coordination Studies of a 3-Hydroxy-4-pyridinone Aza Scorpiand Derivative.
abstract: The synthesis, acid-base behavior, and Cu(2+) 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 Cu(2+) complexes of 1:2, 2:2, 4:3, 1:1, and 2:1 Cu(2+)/L1 stoichiometries. UV-vis analysis and electrochemical studies evidence the implication of the pyridinone moieties in the metal coordination of the 1:2 Cu(2+)/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 Cu(2+) diminishes the antioxidant activity because of its coordination to the pyridinone moiety phenolic group.
authors.affiliation: Departamento de Investigación en Polímeros y Materiales, Universidad de Sonora , Calle Rosales y Blvd. Luis Encinas s/n, Col. Centro, Hermosillo, Sonora 83000, México.|Instituto de Ciencia Molecular , C/Catedrático José Beltrán 2, 46980 Paterna, Valencia, Spain.
authors.forename: Luis M
authors.initials: LM
authors.lastname: López-Martínez
authors.affiliation: Instituto de Ciencia Molecular , C/Catedrático José Beltrán 2, 46980 Paterna, Valencia, Spain.
authors.forename: Javier
authors.initials: J
authors.lastname: Pitarch-Jarque
authors.affiliation: Instituto de Ciencia Molecular , C/Catedrático José Beltrán 2, 46980 Paterna, Valencia, Spain.
authors.forename: Àlvar
authors.initials: À
authors.lastname: Martínez-Camarena
authors.affiliation: Instituto de Ciencia Molecular , C/Catedrático José Beltrán 2, 46980 Paterna, Valencia, Spain.
authors.forename: Enrique
authors.initials: E
authors.lastname: García-España
authors.affiliation: Departamento de Química Física, Universidad de Valencia , C/Dr Moliner 50, 46100 Burjassot, Valencia, Spain.
authors.forename: Roberto
authors.initials: R
authors.lastname: Tejero
authors.affiliation: Departamento de Investigación en Polímeros y Materiales, Universidad de Sonora , Calle Rosales y Blvd. Luis Encinas s/n, Col. Centro, Hermosillo, Sonora 83000, México.
authors.forename: Hisila
authors.initials: H
authors.lastname: Santacruz-Ortega
authors.affiliation: Departamento de Investigación en Polímeros y Materiales, Universidad de Sonora , Calle Rosales y Blvd. Luis Encinas s/n, Col. Centro, Hermosillo, Sonora 83000, México.
authors.forename: Rosa-Elena
authors.initials: RE
authors.lastname: Navarro
authors.affiliation: Departamento de Investigación en Polímeros y Materiales, Universidad de Sonora , Calle Rosales y Blvd. Luis Encinas s/n, Col. Centro, Hermosillo, Sonora 83000, México.|Laboratorio de Estructura Biomolecular. Centro de Investigación en Alimentación y Desarrollo (CIAD) , A. C. Carretera a Ejido La Victoria Km 0.6, Hermosillo, Sonora 83304, México.
authors.forename: Rogerio R
authors.initials: RR
authors.lastname: Sotelo-Mundo
authors.affiliation: Departamento de Investigación en Polímeros y Materiales, Universidad de Sonora , Calle Rosales y Blvd. Luis Encinas s/n, Col. Centro, Hermosillo, Sonora 83000, México.
authors.forename: Mario Alberto
authors.initials: MA
authors.lastname: Leyva-Peralta
authors.affiliation: Departamento de Química Analítica, Universidad de Valencia , C/Dr Moliner 50, 46100 Burjassot, Valencia, Spain.
authors.forename: Antonio
authors.initials: A
authors.lastname: Doménech-Carbó
authors.affiliation: Instituto de Ciencia Molecular , C/Catedrático José Beltrán 2, 46980 Paterna, Valencia, Spain.
authors.forename: Begoña
authors.initials: B
authors.lastname: Verdejo
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002614:Chelating Agents / Q000737:chemistry* / Q000494:pharmacology; D060326:Chemistry Techniques, Synthetic; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D011199:Potentiometry; D011725:Pyridines / Q000737:chemistry*; D011728:Pyridones / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
chemical_list: D000975:Antioxidants; D002614:Chelating Agents; D056831:Coordination Complexes; D011725:Pyridines; D011728:Pyridones; D003300:Copper