The complex [VONargPhenCl] (Narg, naringin; phen = 1,10-phenanthroline) was synthesized and characterized. Comparative analysis with the binary complex, [VO(Narg)₂], revealed improvements in both antioxidant and anticancer effects upon replacing one Narg ligand with Phen. The new complex behaved as a better antioxidant against reactive oxygen species (ROS) and displayed higher cytotoxicity (against the A549 human lung cancer cell line, 24 h incubation) compared to the ligands and the binary complex. This increased cytotoxic effect was associated with intracellular ROS generation and GSH/GSSG depletion, indicating an oxidative stress mechanism. Additional observations, such as the depletion of mitochondrial membrane potential and morphological changes, suggested the involvement of an intrinsic apoptotic pathway. Furthermore, the complex exhibited enhanced cellular uptake of vanadium compared to the binary complex. The complex demonstrated spontaneous interaction with bovine serum albumin and the binding constant values indicated its ability to be transported by this protein. This study underscores the significance of incorporating a compound with π-electronic delocalization into the coordination sphere of the oxidovanadium(IV) cation that improves the antioxidant capacity. Moreover, its lipophilic characteristics impart an improved transport across the cellular membrane and enhance the pro-oxidant effects in cancer cells, ultimately enhancing the anticancer actions of the metal complex.

中文翻译：

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第二配体菲咯啉对氧化钒(IV)/柚皮苷复合物的抗氧化、促氧化和细胞毒性作用的影响

合成并表征了复合物 [VONargPhenCl]（Narg、柚皮苷；phen = 1,10-菲咯啉）。与二元复合物 [VO(Narg) ₂ ] 的比较分析表明，用 Phen 取代一种 Narg 配体后，抗氧化和抗癌作用均有所改善。与配体和二元复合物相比，新复合物对活性氧 (ROS) 具有更好的抗氧化剂作用，并表现出更高的细胞毒性（针对 A549 人肺癌细胞系，孵育 24 小时）。这种细胞毒性作用的增加与细胞内 ROS 的产生和 GSH/GSSG 的消耗有关，表明存在氧化应激机制。其他观察结果，例如线粒体膜电位的耗竭和形态变化，表明涉及内在的凋亡途径。此外，与二元复合物相比，该复合物表现出增强的细胞对钒的吸收。该复合物表现出与牛血清白蛋白的自发相互作用，并且结合常数值表明其能够被该蛋白质转运。这项研究强调了将具有 π 电子离域作用的化合物纳入氧化钒 ( IV ) 阳离子的配位层中对于提高抗氧化能力的重要性。此外，其亲脂特性可改善细胞膜的运输，增强癌细胞的促氧化作用，最终增强金属络合物的抗癌作用。