Synthesis and characterization of a 13-member macrocycle functionalized by tyramine arms: Complexation with Cu2+ and antioxidant capacity

Luis Miguel López-Martínez, Hisila Santacruz-Ortega*, Rosa Elena Navarro, Motomichi Inoue, Rocío Sugich-Miranda, Javier Hernández-Paredes, Ivan Castillo, Rogerio R. Sotelo-Mundo

*Autor correspondiente de este trabajo

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

6 Citas (Scopus)

Resumen

A new macrocycle bearing tyramine arms through amide linkages, 2,2′-(2,9-dioxo-1,4,7,10-tetraazacyclotridecane-4,7-diyl)bis(N-(4-hydroxyphenethyl)acetamide) abbreviated as L13Tyra, has been synthesized with amide-coupling agents in a microwave reactor. This macrocycle involves two potential metal-coordinating and bioactive sites, i.e., the tetraaza-macrocyclic ring (with a low basicity of the amino nitrogen) and the pendant phenol arms (with a small pKa 8.6). The Cu2+ complex has different compositions in solid and in solution. An X-ray crystal study shows that a mononuclear complex [Cu(L13Tyra – 2H)]0 is formed with a square coordination of two deprotonated amide nitrogen and two amino nitrogen atoms of the macrocyclic ring; a carbonyl oxygen atom from a pendant arm occupies an axial site to construct a square pyramid. UV–Vis spectrometric titrations in aqueous solutions indicate the formation of a binuclear complex [Cu2(L13Tyra – 4H)(H2O)x]0 in which phenolate oxygen atoms of the tyramine arms coordinate a Cu2+ ion in addition to the coordination of the macrocyclic chelate; such a binuclear structure is maintained only in solution. The uncoordinated ligand has a high antioxidant capacity with a TEAC (Trolox equivalent antioxidant capacity) assay comparable to that of ascorbic acid, thanks to the phenolic OH of the tyramine arms. Copper(II) ion works as an inhibitor against the activity; the TEAC assay of the binuclear complex is as small as one-twentieth that of the uncoordinated ligand. Antiproliferative and cytotoxic assays with normal and cancer cell lines show no toxicity for both the ligand and its Cu2+ complex.

Idioma originalInglés
Páginas (desde-hasta)438-448
Número de páginas11
PublicaciónPolyhedron
Volumen127
DOI
EstadoPublicada - 2017

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© 2016 Elsevier Ltd

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