Casiopeinas of Third Generations: Synthesis, Characterization, Cytotoxic Activity and Structure-Activity Relationships of Mixed Chelate Compounds with Bioactive Secondary Ligands
Por:
Figueroa-DePaz, Yeshenia, Perez-Villanueva, Jaime, Soria-Arteche, Olivia, Martinez-Otero, Diego, Gomez-Vidales, Virginia, Ortiz-Frade, Luis, Ruiz-Azuara, Lena
Publicada:
1 jun 2022
Resumen:
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. H-1,
C-13 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 (E-1/2) 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.
Filiaciones:
Figueroa-DePaz, Yeshenia:
Univ Nacl Autonoma Mexico, Fac Quim, Dept Quim Inorgan & Nucl, Ave Univ 3000, Mexico City 04510, DF, Mexico
Perez-Villanueva, Jaime:
Univ Autonoma Metropollitana Xochimilco UAM X, Dept Sistemas Biol, Div Ciencias Biol & Salud, Mexico City 04960, DF, Mexico
Soria-Arteche, Olivia:
Univ Autonoma Metropollitana Xochimilco UAM X, Dept Sistemas Biol, Div Ciencias Biol & Salud, Mexico City 04960, DF, Mexico
Martinez-Otero, Diego:
Ctr Conjunto Invest Quim Sustentable UAEM UNAM, Carretera Toluca Atlacomulco,Km 14-5, Toluca 50200, Mexico
Gomez-Vidales, Virginia:
Univ Nacl Autonoma Mexico, Inst Quim, Av Univ 3000, Mexico City 04510, DF, Mexico
Ortiz-Frade, Luis:
Ctr Invest & Desarrollo Tecnol Electroquim SC Par, Pedro De Escobedo 76703, Queretaro, Mexico
Ruiz-Azuara, Lena:
Univ Nacl Autonoma Mexico, Fac Quim, Dept Quim Inorgan & Nucl, Ave Univ 3000, Mexico City 04510, DF, Mexico
Green Published, gold, Gold, Green
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