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卤代香豆素衍生物的合成及抗增殖作用。

Synthesis and Antiproliferative Effect of Halogenated Coumarin Derivatives.

机构信息

Department of Biomedical Sciences, University of Cagliari, University Campus, 09042 Monserrato, CA, Italy.

Department of Chemical and Geological Sciences, University of Cagliari, University Campus, 09042 Monserrato, CA, Italy.

出版信息

Molecules. 2022 Dec 14;27(24):8897. doi: 10.3390/molecules27248897.

DOI:10.3390/molecules27248897
PMID:36558029
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9786284/
Abstract

A series of 6- and 6,8-halocoumarin derivatives have been investigated as potential antiproliferative compounds against a panel of tumor and normal cell lines. Cytotoxic effects were determined by the MTT method. To investigate the potential molecular mechanism involved in the cytotoxic effect, apoptosis assay, cell cycle analysis, reactive oxygen species (ROS), and reduced glutathione analysis were performed. Among the screened compounds, coumarins 6,8-dibromo-2-oxo-2-chromene-3-carbonitrile and 6,8-diiodo-2-oxo-2-chromene-3-carbonitrile exhibited the most antiproliferative effect in thyroid cancer-derived cells TPC-1. The apoptosis assay showed that both and induced apoptosis in TPC-1 thyroid cancer cells. According to these experiments, both coumarins induced a slight increase in TPC-1 cells in the G2/M phase and a decrease in the S phase. A significant increase in ROS levels was observed in TPC-1 treated with diiodocoumarin , while the dibromocoumarin induced a decrease in ROS in a dose and time-dependent manner.

摘要

已经研究了一系列 6- 和 6,8-卤代香豆素衍生物，作为针对一系列肿瘤和正常细胞系的潜在抗增殖化合物。通过 MTT 法测定细胞毒性作用。为了研究细胞毒性作用涉及的潜在分子机制，进行了凋亡测定、细胞周期分析、活性氧（ROS）和还原型谷胱甘肽分析。在所筛选的化合物中，香豆素 6,8-二溴-2-氧代-2-色烯-3-甲腈 和 6,8-二碘-2-氧代-2-色烯-3-甲腈在甲状腺癌细胞 TPC-1 中表现出最强的抗增殖作用。凋亡测定表明，和都诱导 TPC-1 甲状腺癌细胞凋亡。根据这些实验，两种香豆素均诱导 TPC-1 细胞在 G2/M 期略有增加，在 S 期减少。用二碘代香豆素处理 TPC-1 时，观察到 ROS 水平显著增加，而二溴代香豆素则以剂量和时间依赖的方式诱导 ROS 减少。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/2e2b418299c9/molecules-27-08897-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/7e6b22709fc5/molecules-27-08897-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/79d6c5569a5b/molecules-27-08897-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/c3fd0ab1597f/molecules-27-08897-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/44569b10dce4/molecules-27-08897-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/2e2b418299c9/molecules-27-08897-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/7e6b22709fc5/molecules-27-08897-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/79d6c5569a5b/molecules-27-08897-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/c3fd0ab1597f/molecules-27-08897-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/44569b10dce4/molecules-27-08897-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9c1/9786284/2e2b418299c9/molecules-27-08897-g004.jpg

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本文引用的文献

1
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2
Synergistic Effect of Cerium in Dual Photoinduced Ligand-to-Metal Charge Transfer and Lewis Acid Catalysis: Diastereoselective Alkylation of Coumarins.铈在双重光诱导配体到金属电荷转移和路易斯酸催化中的协同效应：香豆素的立体选择性烷基化。
J Org Chem. 2022 Jul 15;87(14):8970-8982. doi: 10.1021/acs.joc.2c00677. Epub 2022 Jun 27.
3
A review on convenient synthesis of substituted coumarins using reuseable solid acid catalysts.
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Molecules. 2023 Mar 6;28(5):2413. doi: 10.3390/molecules28052413.
关于使用可重复使用的固体酸催化剂方便合成取代香豆素的综述。
RSC Adv. 2021 Sep 1;11(47):29130-29155. doi: 10.1039/d1ra04887b.
4
Dual PI3K/Akt Inhibitors Bearing Coumarin-Thiazolidine Pharmacophores as Potential Apoptosis Inducers in MCF-7 Cells.具有香豆素-噻唑烷药效基团的双PI3K/Akt抑制剂作为MCF-7细胞中潜在的凋亡诱导剂
Pharmaceuticals (Basel). 2022 Mar 31;15(4):428. doi: 10.3390/ph15040428.
5
Deconstructive Insertion of Oximes into Coumarins: Modular Synthesis of Dihydrobenzofuran-Fused Pyridones.肟的去构筑性插入到香豆素中：二氢苯并呋喃并吡啶酮的模块化合成。
Org Lett. 2022 Apr 1;24(12):2282-2287. doi: 10.1021/acs.orglett.2c00384. Epub 2022 Mar 23.
6
Synthesis and Photophysical Properties of Fluorescent 6-Aryl-D-π-A Coumarin Derivatives.荧光6-芳基-D-π-A香豆素衍生物的合成及光物理性质
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7
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9
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Front Oncol. 2020 Dec 4;10:592853. doi: 10.3389/fonc.2020.592853. eCollection 2020.
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Curr Top Med Chem. 2021;21(19):1725-1736. doi: 10.2174/1568026620999201113110041.