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IF 3.7 2区化学 Q2 CHEMISTRY, APPLIED

Applied Organometallic Chemistry Pub Date : 2024-09-30 DOI:10.1002/aoc.7777

P. Dhivakar, G. Kalaiarasi, S. Parveen, Nouf M. Alyami, Fatimah S. Alkhattaf, Priya Prasad

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引用次数: 0

摘要

由穿心莲内酯与呋喃-2-羧酸酰肼（AFC）、吡啶-3-羧酸酰肼（AGC）和噻吩-2-羧酸酰肼（ATC）反应制备了一组新的穿心莲内酯酰肼衍生物（AFC、AGC 和 ATC），并制备了相应的钌（II）配合物（Ru-AFC、Ru-AGC 和 Ru-ATC）、在搅拌条件下，[RuCl2(η6-p-cymene)]2 与配体在二氯甲烷中直接反应，合成了穿心莲内酯与呋喃-2-羧酸酰肼（AFC）、吡啶-3-羧酸酰肼（AGC）和噻吩-2-羧酸酰肼（ATC）及其相应的钌（II）配合物（Ru-AFC、Ru-AGC 和 Ru-ATC）。这些化合物通过元素分析、红外光谱、紫外可见光谱、1H NMR 和 ESI-MS 光谱技术进行了分析，所获得的光谱数据显示配体通过其烯氧和胺氮与 Ru(II) 离子配位。计算了配体和配合物对 DPPH-、ABTS-+、O2- 和 NO- 自由基的抗氧化活性，并将其结果与标准抗氧化剂进行了比较。使用 MTT 法（MTT = 3-（4,5-二甲基噻唑-2-基）-2,5-二苯基溴化四唑）评估了合成配体和配合物对 A549 和 HeLa 细胞系的细胞毒活性。在这些化合物中，复合物 Ru-AGC 对 A549 和 HeLa 癌细胞具有更好的细胞毒性作用，IC50 值分别为 4.75 ± 0.17 和 6.32 ± 0.26 μM。此外，使用人脐静脉内皮细胞（HUVEC）证实了这些化合物的无毒性。用 AO/EB 和 DAPI 染色法检测细胞凋亡情况，并用流式细胞仪测定凋亡和坏死细胞的百分比。总体而言，由于螯合作用，我们发现钌（II）-烯配合物的生物活性比它们的母配体更强，而在这些配合物中，Ru-AGC 由于在配体的 N 端位置存在吡啶环而表现出更好的活性。研究结果表明，开发高活性钌配合物作为抗癌剂具有很大的可能性。

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New Organoruthenium(II) Complexes Containing Andrographolide-Appended Hydrazide Derivatives: Synthesis, Spectral Characterization, Anticancer Evaluation

A new set of andrographolide-appended hydrazide derivatives (AFC, AGC, and ATC) were prepared from the reaction of andrographolide with furan-2-carboxylic acid hydrazide (AFC), pyridine-3-carboxylic acid hydrazide (AGC), and thiophene 2-carboxylic acid hydrazide (ATC), and their corresponding ruthenium(II) complexes (Ru-AFC, Ru-AGC, and Ru-ATC) were synthesized by the direct reaction of [RuCl₂(η⁶-p-cymene)]₂ with ligands in dichloromethane under stirring condition. The compounds were analyzed by elemental analysis, IR, UV-Vis, ¹H NMR, and ESI-MS spectrometric techniques, and the obtained spectral data revealed that the ligands coordinated to Ru(II) ion through their enone oxygen and amine nitrogen. Antioxidant activities of the ligands and complexes were calculated against DPPH^•, ABTS^•+, O²⁻, and NO^• free radicals and their results were compared with standard antioxidants. The cytotoxic activity of the synthesized ligands and complexes toward A549 and HeLa cell lines was evaluated using MTT method (MTT = 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide). Among the compounds, the complex Ru-AGC showed better cytotoxic effect against A549 and HeLa cancer cells with IC₅₀ values of 4.75 ± 0.17 and 6.32 ± 0.26 μM, respectively. Further, the nontoxic nature of the compounds was confirmed by using human umbilical vein endothelial (HUVEC) cells. The apoptosis was inspected with AO/EB and DAPI staining methods; further, the percentages of the apoptotic and necrotic cells were determined by flow cytometry. Overall, the biological activities of our ruthenium(II)-arene complexes were found to be more potent than their parent ligands due to chelation, and among the complexes, Ru-AGC showed better activity due to the presence of pyridine ring in the N-terminal position of the ligand. The obtained results highlighted the strong possibility to develop highly active ruthenium complexes as anticancer agents.

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来源期刊

Applied Organometallic Chemistry 化学-无机化学与核化学

CiteScore

7.80

自引率

10.30%

发文量

408

审稿时长

2.2 months

期刊介绍： All new compounds should be satisfactorily identified and proof of their structure given according to generally accepted standards. Structural reports, such as papers exclusively dealing with synthesis and characterization, analytical techniques, or X-ray diffraction studies of metal-organic or organometallic compounds will not be considered. The editors reserve the right to refuse without peer review any manuscript that does not comply with the aims and scope of the journal. Applied Organometallic Chemistry publishes Full Papers, Reviews, Mini Reviews and Communications of scientific research in all areas of organometallic and metal-organic chemistry involving main group metals, transition metals, lanthanides and actinides. All contributions should contain an explicit application of novel compounds, for instance in materials science, nano science, catalysis, chemical vapour deposition, metal-mediated organic synthesis, polymers, bio-organometallics, metallo-therapy, metallo-diagnostics and medicine. Reviews of books covering aspects of the fields of focus are also published.