Casiopeinas of Third Generations: Synthesis, Characterization, Cytotoxic Activity and Structure–Activity Relationships of Mixed Chelate Compounds with Bioactive Secondary Ligands

Autor: Yeshenia Figueroa-DePaz, Jaime Pérez-Villanueva, Olivia Soria-Arteche, Diego Martínez-Otero, Virginia Gómez-Vidales, Luis Ortiz-Frade, Lena Ruiz-Azuara
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: Molecules, Vol 27, Iss 11, p 3504 (2022)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules27113504
Popis: Casiopeinas are a family of copper(II) coordination compounds that have shown an important antineoplastic effect and low toxicity in normal cells. These compounds induce death cells by apoptosis through a catalytic redox process with endogenous reducing agents. Further studies included a structural variation, improving the activity and selectivity in cancer cells or other targets. In the present work we report the third generation, which contains a bioactive monocharged secondary ligand, as well as the design, synthesis, characterization and antiproliferative activity, of sixteen new copper(II) coordination compounds with curcumin or dimethoxycurcumin as secondary ligands. All compounds were characterized by elemental analysis, FTIR, UV-Vis, magnetic susceptibility, mass spectra with MALDI-flight time, cyclic voltammetry, electron paramagnetic resonance (EPR) spectroscopy and X-ray diffraction. Crystallization of two complexes was achieved in dimethylsulfoxide (DMSO) with polar solvent, and crystal data demonstrated that a square-based or square-base pyramid geometry are possible. A 1:1:1 stoichiometry (diimine: copper: curcuminoid) ratio and the possibility of a nitrate ion as a counterion were supported. 1H, 13C NMR spectra were used for the ligands. A sulforhodamine B assay was used to evaluate the cytotoxicity effect against two human cancer cell lines, SKLU-1 and HeLa. Electronic descriptors and redox potential were obtained by DFT calculations. Structure–activity relationships are strongly determined by the redox potential (E1/2) of copper(II) and molar volume (V) of the complexes. These compounds can be used as a template to open a wide field of research both experimentally and theoretically.
Databáze: Directory of Open Access Journals
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