New platinum (II) complexes based on schiff bases: synthesis, specification, X-ray structure, ADMET, DFT, molecular docking, and anticancer activity against breast cancer

IF 2.7 3区 化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY JBIC Journal of Biological Inorganic Chemistry Pub Date : 2023-07-15 DOI:10.1007/s00775-023-02005-1
Mahboube Eslami Moghadam, Maryam Hasanzadeh Esfahani, Mahdi Behzad, Samaneh Zolghadri, Nadali Ramezani, Yasaman Azadi
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引用次数: 2

Abstract

Acylpyrazolone-based Schiff base ligands (HLn) and their corresponding Pt(II) complexes with the general formula [Pt(Ln)(Cl)] (n?=?1–3)?were synthesized and characterized by different spectroscopic techniques including 1H-NMR, 195Pt-NMR, LC-Mass, FT–IR, and UV–Vis spectroscopy, as well as elemental analysis. The crystal structure of one of the Schiff base ligands was also obtained. Based on the ADMET comparative results and the bioavailability radar charts, the complexes are completely drug-like. The Schiff base complexes with a structural difference of one methyl group in ligand were used as anticancer agents against human breast cancer cell lines SKBR3 and MDA-MB-231. The IC50 values after treatment by [Pt(L1)Cl] and [Pt(L2)Cl] were obtained more than cisplatin and less than carboplatin on cancer cells MDA-MB-231 and SKBR3, while the IC50 value of [Pt(L3)Cl] was more than both other complexes and clinical Pt drugs. Molecular docking data showed that the groove binding is the main interaction with DNA double strands with a minor contribution from electrostatic interactions. To investigate the structure–activity relationship, DFT computational was done. All quantum chemical parameters display the drug approaching biomacromolecule and more biological activity of [Pt(L1)Cl]?>?[Pt(L2)Cl]?>?[Pt(L3)Cl]. So, three Schiff base platinum complexes can be suitable candidates as anticancer drugs.

Graphical abstract

Schiff-base ligands (HLn) and their Pt(II) complexes ([Pt(Ln)(Cl)], n=1-3) were obtained. To investigate their biological property and main interactions with DNA, ADMET, and cytotoxicity against MDA-MB-231 and SKBR3, DFT, and Molecular docking were done.

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基于希夫碱的新型铂(II)配合物:合成、规范、x射线结构、ADMET、DFT、分子对接、抗乳腺癌活性
酰基吡唑酮基希夫碱配体(HLn)及其对应的Pt(II)配合物,通式为[Pt(Ln)(Cl)] (n?= 1-3)?采用不同的光谱技术,包括1H-NMR、195Pt-NMR、LC-Mass、FT-IR和UV-Vis光谱以及元素分析对其进行了合成和表征。得到了其中一种席夫碱配体的晶体结构。根据ADMET比较结果和生物利用度雷达图,这些配合物完全是类药物的。利用配体中一个甲基结构差异的希夫碱配合物作为抗癌剂,对人乳腺癌细胞株SKBR3和MDA-MB-231进行了研究。[Pt(L1)Cl]和[Pt(L2)Cl]治疗后对癌细胞MDA-MB-231和SKBR3的IC50值均高于顺铂,低于卡铂,而[Pt(L3)Cl]的IC50值均高于其他复合物和临床Pt药物。分子对接数据表明,沟槽结合是与DNA双链的主要相互作用,静电相互作用贡献较小。为了研究结构-活性关系,进行了DFT计算。所有量子化学参数均显示了[Pt(L1)Cl]?>?[Pt(L2)Cl]?>?[Pt(L3)Cl]的药物接近生物大分子和更强的生物活性。因此,三种希夫碱铂配合物可以作为抗癌药物的合适候选者。得到了希夫碱配体(HLn)及其Pt(II)配合物([Pt(Ln)(Cl)], n=1-3)的图形摘要。为了研究它们的生物学特性、与DNA、ADMET的主要相互作用以及对MDA-MB-231和SKBR3的细胞毒性,我们进行了DFT和分子对接。
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来源期刊
JBIC Journal of Biological Inorganic Chemistry
JBIC Journal of Biological Inorganic Chemistry 化学-生化与分子生物学
CiteScore
5.90
自引率
3.30%
发文量
49
审稿时长
3 months
期刊介绍: Biological inorganic chemistry is a growing field of science that embraces the principles of biology and inorganic chemistry and impacts other fields ranging from medicine to the environment. JBIC (Journal of Biological Inorganic Chemistry) seeks to promote this field internationally. The Journal is primarily concerned with advances in understanding the role of metal ions within a biological matrix—be it a protein, DNA/RNA, or a cell, as well as appropriate model studies. Manuscripts describing high-quality original research on the above topics in English are invited for submission to this Journal. The Journal publishes original articles, minireviews, and commentaries on debated issues.
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