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新型噻唑烷-2,4-二酮衍生物作为潜在血管内皮生长因子受体-2（VEGFR-2）抑制剂的发现及研究

Discovery of new thiazolidine-2,4-dione derivatives as potential VEGFR-2 inhibitors: and studies.

作者信息

Eissa Ibrahim H, Elkady Hazem, Rashed Mahmoud, Elwan Alaa, Hagras Mohamed, Dahab Mohammed A, Taghour Mohammed S, Ibrahim Ibrahim M, Husein Dalal Z, Elkaeed Eslam B, Al-Ghulikah Hanan A, Metwaly Ahmed M, Mahdy Hazem A

机构信息

Pharmaceutical Medicinal Chemistry & Drug Design Department, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo, 11884, Egypt.

Department of Pharmaceutical Organic Chemistry, College of Pharmacy, Al-Azhar University, Cairo, 11884, Egypt.

出版信息

Heliyon. 2024 Jan 12;10(2):e24005. doi: 10.1016/j.heliyon.2024.e24005. eCollection 2024 Jan 30.

DOI:10.1016/j.heliyon.2024.e24005
PMID:38298627
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10828660/
Abstract

In this study, a series of seven novel 2,4-dioxothiazolidine derivatives with potential anticancer and VEGFR-2 inhibiting abilities were designed and synthesized as VEGFR-2 inhibitors. The synthesized compounds were tested for their potential to inhibit VEGFR-2 and the growth of HepG2 and MCF-7 cancer cell lines. Among the compounds tested, compound (IC = 0.079 μM) demonstrated the highest -VEGFR-2 efficacy. Furthermore, it demonstrated significant anti-proliferative activities against HepG2 (IC = 2.04 ± 0.06 μM) and MCF-7 (IC = 1.21 ± 0.04 M). Additionally, compound also increased the total apoptotic rate of the MCF-7 cancer cell lines with cell cycle arrest at S phase. As well, computational methods were applied to study the VEGFR-2- complex at the molecular level. Molecular docking and molecular dynamics (MD) simulations were used to investigate the complex's structural and kinetic characteristics. The DFT calculations further revealed the structural and electronic properties of compound . Finally, computational ADMET and toxicity tests were performed indicating the likeness of the proposed compounds to be drugs. The results suggest that compound displays promise as an effective anticancer treatment and can serve as a model for future structural modifications and biological investigations in this field.

摘要

在本研究中，设计并合成了一系列七种具有潜在抗癌和VEGFR-2抑制能力的新型2,4-二氧代噻唑烷衍生物作为VEGFR-2抑制剂。对合成的化合物进行了抑制VEGFR-2以及HepG2和MCF-7癌细胞系生长潜力的测试。在所测试的化合物中，化合物（IC = 0.079 μM）表现出最高的VEGFR-2抑制效果。此外，它对HepG2（IC = 2.04 ± 0.06 μM）和MCF-7（IC = 1.21 ± 0.04 μM）表现出显著的抗增殖活性。此外，化合物还提高了MCF-7癌细胞系的总凋亡率，并使细胞周期停滞在S期。同样，应用计算方法在分子水平上研究VEGFR-2复合物。分子对接和分子动力学（MD）模拟用于研究该复合物的结构和动力学特征。DFT计算进一步揭示了化合物的结构和电子性质。最后，进行了计算ADMET和毒性测试，表明所提出的化合物具有成药的可能性。结果表明，化合物有望成为一种有效的抗癌治疗药物，并可作为该领域未来结构修饰和生物学研究的模型。

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Mol Divers. 2025 Feb 3. doi: 10.1007/s11030-024-11093-3.
()--(3-(1-(2-(4-(2,2,2-Trifluoroacetamido)benzoyl)hydrazono)ethyl)phenyl)nicotinamide: A Novel Pyridine Derivative for Inhibiting Vascular Endothelial Growth Factor Receptor-2: Synthesis, Computational, and Anticancer Studies.
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Molecules. 2022 Nov 9;27(22):7719. doi: 10.3390/molecules27227719.
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New Pyrimidine-5-Carbonitriles as COX-2 Inhibitors: Design, Synthesis, Anticancer Screening, Molecular Docking, and In Silico ADME Profile Studies.新型嘧啶-5-碳腈类化合物作为 COX-2 抑制剂的设计、合成、抗癌筛选、分子对接及体内 ADME 性质研究。
Molecules. 2022 Nov 2;27(21):7485. doi: 10.3390/molecules27217485.
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Discovery of New VEGFR-2 Inhibitors: Design, Synthesis, Anti-Proliferative Evaluation, Docking, and MD Simulation Studies.新型 VEGFR-2 抑制剂的发现：设计、合成、抗增殖评价、对接和 MD 模拟研究。
Molecules. 2022 Sep 21;27(19):6203. doi: 10.3390/molecules27196203.
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, VEGFR-2 inhibition, and anticancer activity of a 3-(hydrazonomethyl)naphthalene-2-ol derivative.3-(肼基亚甲基)萘-2-醇衍生物的血管内皮生长因子受体-2抑制作用及抗癌活性
J Biomol Struct Dyn. 2023 Sep-Oct;41(16):7986-8001. doi: 10.1080/07391102.2022.2127907. Epub 2022 Oct 2.
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Design, synthesis, anti-proliferative evaluation, docking, and MD simulations studies of new thiazolidine-2,4-diones targeting VEGFR-2 and apoptosis pathway.新型噻唑烷-2,4-二酮类化合物的设计、合成、抗增殖活性评价、对接及 MD 模拟研究，靶向 VEGFR-2 和凋亡通路。
PLoS One. 2022 Sep 23;17(9):e0272362. doi: 10.1371/journal.pone.0272362. eCollection 2022.
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Modified Benzoxazole-Based VEGFR-2 Inhibitors and Apoptosis Inducers: Design, Synthesis, and Anti-Proliferative Evaluation.基于苯并恶唑的 VEGFR-2 抑制剂和凋亡诱导剂的修饰：设计、合成与抗增殖活性评价。
Molecules. 2022 Aug 8;27(15):5047. doi: 10.3390/molecules27155047.
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A Multistage In Silico Study of Natural Potential Inhibitors Targeting SARS-CoV-2 Main Protease.针对 SARS-CoV-2 主蛋白酶的天然潜在抑制剂的多阶段计算机研究。
Int J Mol Sci. 2022 Jul 29;23(15):8407. doi: 10.3390/ijms23158407.
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Design, synthesis, in vitro biological assessment and molecular modeling insights for novel 3-(naphthalen-1-yl)-4,5-dihydropyrazoles as anticancer agents with potential EGFR inhibitory activity.设计、合成、体外生物学评估及新型 3-(萘-1-基)-4,5-二氢吡唑类化合物作为具有潜在 EGFR 抑制活性的抗癌剂的分子建模研究。
Sci Rep. 2022 Jul 27;12(1):12821. doi: 10.1038/s41598-022-15050-8.