Two novel unsymmetrical binucleating aroylhydrazonic ligands and four dicopper(II) complexes carrying fluorescent benzopyranothiophene (BPT) or boron dipyrromethene (BODIPY) entities were synthesized and fully characterized. Complex 1, derived from the BPT-containing ligand H₃L1, had its crystal structure elucidated through X-ray diffraction measurements. The absorption and fluorescence profiles of all the compounds obtained were discussed. Additionally, the stability of the ligands and complexes was monitored by UV–vis spectroscopy in DMSO and biologically relevant media. All the compounds showed moderate to high cytotoxicity towards the triple negative human breast cancer cell line MDA-MB-231. BPT derivatives were the most cytotoxic, specially H₃L1, reaching an IC₅₀ value up to the nanomolar range. Finally, fluorescence microscopy imaging studies employing mitochondria- and nucleus-staining dyes showed that the BODIPY-carrying ligand H₃L2 was highly cell permeant and suggested that the compound preferentially accumulates in the mitochondria.

Graphic abstract

中文翻译：

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新型发光苯并吡喃噻吩和 BODIPY 衍生的芳酰腙配体及其二铜 (II) 配合物：合成、抗增殖活性和细胞摄取研究

合成并充分表征了两种新型不对称双核芳酰基腙配体和四种携带荧光苯并吡喃噻吩 (BPT) 或硼二吡咯亚甲基 (BODIPY) 实体的二铜 (II) 配合物。复合物1源自含 BPT 的配体H ₃ L1，通过 X 射线衍射测量阐明了其晶体结构。讨论了所有获得的化合物的吸收和荧光曲线。此外，配体和配合物的稳定性在 DMSO 和生物相关介质中通过紫外-可见光谱监测。所有化合物对三阴性人乳腺癌细胞系 MDA-MB-231 均表现出中等至高度的细胞毒性。BPT 衍生物是最具细胞毒性的，特别是H ₃ L1，达到纳摩尔范围内的IC ₅₀值。最后，使用线粒体和细胞核染色染料的荧光显微镜成像研究表明，携带 BODIPY 的配体H ₃ L2具有高度的细胞渗透性，并表明该化合物优先在线粒体中积累。

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