Design, synthesis, molecular docking, and biological evaluation of new emodin anthraquinone derivatives as potential antitumor substances,Chemistry & Biodiversity

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Design, synthesis, molecular docking, and biological evaluation of new emodin anthraquinone derivatives as potential antitumor substances
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2020-09-02 , DOI: 10.1002/cbdv.202000328
Yuying Li ₁ , Fang Guo ₁ , Tinggui Chen ₁ , Liwei Zhang ₁ , Zhuanhua Wang ₁ , Qiang Su ₁ , Liheng Feng ₁

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The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3‐dihydroxy‐6,8‐dimethoxyanthracene‐9,10‐dione is a natural compound that has been synthesized for the very first time, and 1,3‐dimethoxy‐5,8‐dimethylanthracene‐9,10‐dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3‐dimethoxy‐5,8‐dimethylanthracene‐9,10‐dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3‐dimethoxy‐5,8‐dimethylanthracene‐9,10‐dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

中文翻译：

新型大黄素蒽醌衍生物作为潜在抗肿瘤物质的设计、合成、分子对接和生物学评价

大黄素蒽醌衍生物由于其多种药理活性而普遍用于中药。本研究设计合成了一系列大黄素蒽醌衍生物，其中1,3-二羟基-6,8-二甲氧基蒽-9,10-二酮是首次合成的天然化合物， 1,3-二甲氧基-5,8-二甲基蒽-9,10-二酮是一种以前从未报道过的化合物。有趣的是，虽然这些化合物中总共有七种在流感病毒中显示出神经氨酸酶抑制活性，抑制率超过 50%，但特定的四种化合物显示出对肿瘤细胞增殖的显着抑制。进一步的结果表明，1,3-二甲氧基-5,8-二甲基蒽-9，通过提高细胞内活性氧 (ROS) 的水平，10-二酮通过诱导 HCT116 癌细胞的最高凋亡率并阻止其 G0/G1 细胞周期阶段，在所有合成化合物中显示出最佳的抗癌活性。此外，1,3-二甲氧基-5,8-二甲基蒽-9,10-二酮与BSA蛋白的结合已得到彻底研究。总之，这项研究表明了新的大黄素蒽醌衍生物的神经氨酸酶抑制活性和抗肿瘤潜力。

更新日期：2020-09-02

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