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新型丁香酚衍生物的合成及其对乳腺癌细胞的抗癌活性。

Synthesis and anticancer activity of novel Eugenol derivatives against breast cancer cells.

机构信息

Department of Chemistry, Faculty of Science, Al Baha University, Al Baha, Kingdom of Saudi Arabia.

出版信息

Nat Prod Res. 2023 May;37(10):1632-1640. doi: 10.1080/14786419.2022.2103809. Epub 2022 Jul 25.

Abstract

Eugenol chemically known as 4-allyl-2-methoxyphenol is a major phenolic component of and associated with significant biological activities. In the present work, new eugenol 1,2,3-triazole derivatives have been synthesized, characterized using NMR, mass spectrometry, IR, and elemental analysis and screened for their anticancer activity against breast cancer cells. Compound namely 3-(4-((4-allyl-2-methoxyphenoxy)methyl)-1-1,2,3-triazol-1-yl)-'-(4-methylbenzoyl) benzohydrazide was found to be the most potent candidate and better than eugenol in exhibiting cytotoxicity with IC 6.91 and 3.15 μM, comparable to Doxorubicin with IC 6.58 and 3.21 μM against MDA-MB-231 and MCF-7 cells, respectively. Furthermore, compound treated MCF-7 cells as observed by propidium iodide staining significantly increased cell population of S phase and G2 phase to 43.64% and 35.19%, respectively therefore arresting cell cycle at G2 and S phase. These results indicate that eugenol linked 1,2,3-triazole ring could be used as anticancer leads for the treatment of this deadly diseases.

摘要

丁香酚化学名为 4-丙烯基-2-甲氧基苯酚,是 和相关的重要生物活性的主要酚类成分。在本工作中,合成了新的丁香酚 1,2,3-三唑衍生物,并用 NMR、质谱、IR 和元素分析进行了表征,并对其进行了抗乳腺癌细胞活性筛选。化合物 3-(4-((4-丙烯基-2-甲氧基苯氧基)甲基)-1-1,2,3-三唑-1-基)-'-(4-甲基苯甲酰基)苯甲酰肼被发现是最有效的候选物,其细胞毒性比丁香酚更强,对 MDA-MB-231 和 MCF-7 细胞的 IC 6.91 和 3.15 μM,与阿霉素相当,IC 6.58 和 3.21 μM。此外,用碘化丙啶染色观察到化合物 处理 MCF-7 细胞后,S 期和 G2 期的细胞群体分别显著增加到 43.64%和 35.19%,从而将细胞周期阻滞在 G2 和 S 期。这些结果表明,丁香酚连接的 1,2,3-三唑环可作为治疗这种致命疾病的抗癌先导物。

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