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    陈司燮阳, 李茹, 柴俊, 张涤清, 殷华军, 陈莎莉, 胡静. 3,5-二溴水杨醛缩-4-氨基安替比林席夫碱Cu(Ⅱ)配合物的合成及其抗癌活性评价[J]. 蚌埠医科大学学报, 2023, 48(8): 1080-1084. DOI: 10.13898/j.cnki.issn.1000-2200.2023.08.015
    引用本文: 陈司燮阳, 李茹, 柴俊, 张涤清, 殷华军, 陈莎莉, 胡静. 3,5-二溴水杨醛缩-4-氨基安替比林席夫碱Cu(Ⅱ)配合物的合成及其抗癌活性评价[J]. 蚌埠医科大学学报, 2023, 48(8): 1080-1084. DOI: 10.13898/j.cnki.issn.1000-2200.2023.08.015
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    CHEN Si-xie-yang, LI Ru, CHAI Jun, ZHANG Di-qing, YIN Hua-jun, CHEN Sha-li, HU Jing. Synthesis of Cu(Ⅱ) complex based on 3,5-dibromosalicylaldehyde-4-aminoantipyrine Schiff base and its anticancer activity evaluation[J]. Journal of Bengbu Medical University, 2023, 48(8): 1080-1084. DOI: 10.13898/j.cnki.issn.1000-2200.2023.08.015
    Citation: CHEN Si-xie-yang, LI Ru, CHAI Jun, ZHANG Di-qing, YIN Hua-jun, CHEN Sha-li, HU Jing. Synthesis of Cu(Ⅱ) complex based on 3,5-dibromosalicylaldehyde-4-aminoantipyrine Schiff base and its anticancer activity evaluation[J]. Journal of Bengbu Medical University, 2023, 48(8): 1080-1084. DOI: 10.13898/j.cnki.issn.1000-2200.2023.08.015
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    3,5-二溴水杨醛缩-4-氨基安替比林席夫碱Cu(Ⅱ)配合物的合成及其抗癌活性评价

    Synthesis of Cu(Ⅱ) complex based on 3,5-dibromosalicylaldehyde-4-aminoantipyrine Schiff base and its anticancer activity evaluation

      摘要
    • 摘要:
      目的设计并合成新的3,5-二溴水杨醛缩-4-氨基安替比林席夫碱Cu(Ⅱ)配合物(CuL2), 并评价其抗癌活性。
      方法利用3,5-二溴水杨醛与4-氨基安替比林发生缩合反应, 合成新的3,5-二溴水杨醛缩-4-氨基安替比林席夫碱配体(HL)。将HL与Cu(Ac)2·H2O通过溶剂热法合成了CuL2, 并利用X射线单晶衍射、多晶粉末衍射(PXRD)、红外光谱(FT-IR)和热重分析(TGA-DSC)等技术对CuL2进行表征。MTT法检测HL及CuL2对MDA-MB-231细胞、SMMC-7721细胞、CNE-2Z细胞和A-549细胞的体外抗肿瘤活性。流式细胞术(FCM)分析CuL2对MDA-MB-231细胞凋亡和周期的影响。
      结果X射线单晶衍射分析显示, CuL2为单核金属配合物, 属单斜晶系, 空间群为C2/c, 具有微扭曲的四方形配位结构; PXRD显示, CuL2结晶度良好, 晶体结构符合单晶测试的分析结果; 配体和配合物的FT-IR特征峰与分子结构一致; TGA-DSC显示, CuL2在270℃以下具有良好的热稳定性。MTT实验结果显示, 当HL与Cu(Ⅱ)形成配合物时, CuL2抗癌活性优于HL, 其抑制MDA-MB-231细胞和SMMC-7721细胞活性较强, 略低于顺铂。FCM分析结果显示, CuL2可诱导MDA-MB-231细胞凋亡(P < 0.05);CuL2诱导MDA-MB-231细胞阻滞在G0/G1期和S期(P < 0.05)。
      结论合成得到CuL2, 其可抑制MDA-MB-231细胞和SMMC-7721细胞活性, 诱导MDA-MB-231细胞凋亡和细胞周期阻滞。

       

      Abstract:
      ObjectiveTo design and synthesize a novel Cu(Ⅱ) complex based on 3,5-dibromosalicylaldehyde-4-aminoantipyrine Schiff base (CuL2), and evaluate its anticancer activity.
      MethodsA novel Schiff base ligand, 3,5-dibromosalicylalde-4-aminoantipyrine (HL), was synthesized by condensation reaction of 3,5-dibromosalicylalde and 4-aminoantipyrine.The CuL2 was synthesized by solvothermal method with HL and Cu(Ac)2·H2O.The CuL2 was characterized by X-ray single crystal diffraction, polycrystaline powder X-ray diffraction (PXRD), Fourier transform infrared spectroscopy (FT-IR) and thermogravimetric analysis (TGA-DSC).The in vitro anticancer activity of HL and CuL2 on MDA-MB-231, SMMC-7721, CNE-2Z and A-549 cells was determined by MTT assay.The effect of CuL2 on apoptosis and cell cycle of MDA-MB-231 cells was analyzed by flow cytometry (FCM).
      ResultsX-ray single crystal diffraction analysis showed that CuL2 was a mononuclear metal complex, belonging to the monoclinic crystal system, with space group of C2/c and 4-coordination micro-torsion square structure; PXRD showed that the crystallinity of CuL2 was good, and the crystal structure accorded with the results of single crystal test; the FT-IR characteristic peaks were consistent with the molecular structures of ligand and complex; TGA-DSC analysis showed that CuL2 had good thermal stability below 270 ℃.The MTT assay results showed that when HL forms a complex with Cu (Ⅱ), CuL2 had better anticancer activity than HL, and its inhibitory activity on MDA-MB-231 cells and SMMC-7721 cells was stronger, which was slightly lower than that of cisplatin.The FCM analysis results showed that CuL2 could induce apoptosis in MDA-MB-231 cells (P < 0.05), and induce cell cycle arrest in G0/G1 and S phases in MDA-MB-231 cells (P < 0.05).
      ConclusionsThe CuL2 is synthesized, which can inhibit the activity of MDA-MB-231 and SMMC-7721 cells, and induce cell cycle arrest and apoptosis in MDA-MB-231 cells.

       

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