Departamento de Química Inorgánica y Nuclear, Facultad de Química, Universidad Nacional Autónoma de México, Avenida Universidad 3000, Mexico City 04510, Mexico.
Departamento de Sistemas Biológicos, División de Ciencias Biológicas y de la Salud, Universidad Autónoma Metropollitana-Xochimilco (UAM-X), Mexico City 04960, Mexico.
Molecules. 2022 May 30;27(11):3504. doi: 10.3390/molecules27113504.
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, C 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) 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.
Casiopeinas 是一类铜 (II) 配合物，已显示出重要的抗肿瘤作用和对正常细胞的低毒性。这些化合物通过与内源性还原剂的催化氧化还原过程诱导细胞凋亡。进一步的研究包括结构变化，提高在癌细胞或其他靶标中的活性和选择性。在本工作中，我们报告了第三代，它包含一个生物活性的单价二次配体，以及十六个新的铜 (II) 配合物的设计、合成、表征和抗增殖活性，这些配合物的二次配体为姜黄素或二甲氧基姜黄素。所有化合物均通过元素分析、FTIR、UV-Vis、磁化率、MALDI-flight time 质谱、循环伏安法、电子顺磁共振 (EPR) 光谱和 X 射线衍射进行了表征。两个配合物在 DMSO 中用极性溶剂进行了结晶，晶体数据表明可能存在正方形或正方形基锥几何形状。支持 1:1:1 的化学计量比（二亚胺：铜：姜黄素类）和可能存在硝酸根离子作为抗衡离子。H、C NMR 光谱用于配体。使用磺基罗丹明 B 测定法评估了对两种人类癌细胞系 SKLU-1 和 HeLa 的细胞毒性作用。通过 DFT 计算获得电子描述符和氧化还原电位。结构-活性关系强烈取决于铜 (II) 的氧化还原电位 (E) 和配合物的摩尔体积 (V)。这些化合物可用作模板，在实验和理论上开辟广泛的研究领域。
