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含1,1'-[(3-氟苯基)亚甲基]双-[3-(3-氟苯基)咪唑并[1,5-a]吡啶]的铜和锌配合物的合成、结构及抗癌活性

Syntheses, structures and anti-cancer activities of Cu and Zn complexes containing 1,1'-[(3-fluoro-phen-yl)methyl-ene]bis-[3-(3-fluoro-phen-yl)imidazo[1,5-]pyridine].

作者信息

Le Thi Hong Hai, Nguyen Van Hau, Hoang Tuan Duong, Tran Quang Hung, Dang Thanh Tuan, Van Meervelt Luc

机构信息

Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, Vietnam.

Institute of Natural Sciences, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, Vietnam.

出版信息

Acta Crystallogr E Crystallogr Commun. 2025 Jan 1;81(Pt 1):47-52. doi: 10.1107/S2056989024011617.

Abstract

Two novel complexes, [Cu()Cl] and [Zn()Cl], were synthesized from 1,1'-[(3-fluoro-phen-yl)methyl-ene]bis-[3-(3-fluoro-phen-yl)imidazo[1,5-]pyridine] (), and copper(II) and zinc(II) chloride, respectively. The structures of these complexes were confirmed using ESI-MS, IR and H NMR spectra. The results reveal mononuclear structures in which the central metal atoms are coordinated by two N atoms from the imidazole rings and two Cl ligands. The structure of the complex [systematic name: di-chlorido-{1,1'-[(3-fluoro-phen-yl)methyl-ene]bis-[3-(3-fluoro-phen-yl)imidazo[1,5-]pyridine]-κ ,'}copper(II), [CuCl(CHFN)], was confirmed by single-crystal X-ray diffraction. The Cu atom adopts a distorted tetra-hedral coordination environment with an NCl coordination set. The predominant features of the crystal packing are C-H⋯F, C-H⋯π and C-F⋯π inter-actions. Biological evaluations demonstrated that both complexes exhibit enhanced anti-cancer activity compared to the free ligand, with IC values ranging between 18.93 and 67.06 µ. Notably, the Cu complex displays excellent inhibitory activity against the MCF7 breast cancer cell line (IC = 27.99 µ), approximately twice as effective as cisplatin. Conversely, the complex shows greater efficacy against Hep-G2 and A549 lung cancer cell lines, with IC values between 18.93 and 24.83 µ. The results suggest that Cu and Zn complexes of show potential as cancer treatment agents.

摘要

两种新型配合物[Cu()Cl]和[Zn()Cl]分别由1,1'-[(3-氟苯基)亚甲基]双-3-(3-氟苯基)咪唑并[1,5-]吡啶与氯化铜(II)和氯化锌(II)合成。通过电喷雾电离质谱(ESI-MS)、红外光谱(IR)和核磁共振氢谱(¹H NMR)对这些配合物的结构进行了确证。结果表明它们为单核结构,中心金属原子由咪唑环上的两个氮原子和两个氯配体配位。配合物[系统命名:二氯-{1,1'-[(3-氟苯基)亚甲基]双-[3-(3-氟苯基)咪唑并[1,5-]吡啶]-κ²N,'²N}铜(II),[CuCl₂(C₁₉H₁₂F₂N₄)]的结构通过单晶X射线衍射得以确证。铜原子采用扭曲的四面体配位环境,配位原子为NCl组合。晶体堆积的主要特征为C-H⋯F、C-H⋯π和C-F⋯π相互作用。生物学评价表明,与游离配体相比,两种配合物均表现出增强的抗癌活性,IC₅₀值在18.93至67.06 μ之间。值得注意的是,铜配合物对MCF7乳腺癌细胞系表现出优异的抑制活性(IC₅₀ = 27.99 μ),约为顺铂的两倍。相反,锌配合物对Hep-G2和A549肺癌细胞系显示出更高的疗效,IC₅₀值在18.93至24.83 μ之间。结果表明,该配体的铜和锌配合物具有作为癌症治疗药物的潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5c77/11701767/6e19ee0d16a7/e-81-00047-fig1.jpg

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