Potent Cytotoxicity of Novel L-Shaped Ortho-Quinone Analogs through Inducing Apoptosis
Potent Cytotoxicity of Novel L-Shaped Ortho-Quinone Analogs through Inducing Apoptosis
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新型 L 型邻醌类似物通过诱导细胞凋亡产生有效的细胞毒性
DOI：
10.3390/molecules24224138
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发表时间：
2019-11
期刊：
影响因子：
4.6
通讯作者：
Pan Wei-Dong
中科院分区：
文献类型：
--
作者：
Li Sheng-You;Sun Ze-Kun;Zeng Xue-Yi;Zhang Yue;Wang Meng-Ling;Hu Sheng-Cao;Song Jun-Rong;Luo Jun;Chen Chao;Luo Heng;Pan Wei-Dong
采用一锅法双自由基合成策略，通过去除呋喃环C-3位的甲基并在呋喃环C-2位引入不同的侧链，设计并合成了27个L型邻醌类似物。研究了合成的衍生物对人白血病细胞K562、前列腺癌细胞PC 3和黑素瘤细胞WM 9的细胞毒性活性。化合物TB 1、TB 3、TB 4、TB 6、TC 1、TC 3、TC 5、TC 9、TC 11、TC 12、TC 14、TC 15、TC 16和TC 17对三种癌细胞具有较好的广谱细胞毒活性。TB 7和TC 7分别选择性地对白血病细胞K562和前列腺癌细胞PC 3表现出强有力的抑制活性。进一步研究发现TB 3、TC 1、TC 3、TC 7和TC 17均能明显诱导PC 3细胞凋亡。TC 1和TC 17可明显诱导K562细胞凋亡。TC 1、TC 11和TC 14可诱导WM 9细胞凋亡。构效关系评价表明，去除呋喃环C-3位甲基，在呋喃环C-2位引入不同的侧链是提高L型邻醌类似物抗癌活性的有效策略。
Twenty-seven L-shaped ortho-quinone analogs were designed and synthesized using a one pot double-radical synthetic strategy followed by removing methyl at C-3 of the furan ring and introducing a diverse side chain at C-2 of the furan ring. The synthetic derivatives were investigated for their cytotoxicity activities against human leukemia cells K562, prostate cancer cells PC3, and melanoma cells WM9. Compounds TB1, TB3, TB4, TB6, TC1, TC3, TC5, TC9, TC11, TC12, TC14, TC15, TC16, and TC17 exhibited a better broad-spectrum cytotoxicity on three cancer cells. TB7 and TC7 selectively displayed potent inhibitory activities on leukemia cells K562 and prostate cancer cells PC3, respectively. Further studies indicated that TB3, TC1, TC3, TC7, and TC17 could significantly induce the apoptosis of PC3 cells. TC1 and TC17 significantly induced apoptosis of K562 cells. TC1, TC11, and TC14 induced significant apoptosis of WM9 cells. The structure-activity relationships evaluation showed that removing methyl at C-3 of the furan ring and introducing diverse side chains at C-2 of the furan ring is an effective strategy for improving the anticancer activity of L-shaped ortho-quinone analogs.
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对某些氧取代的日记酮的环保合成和抗增殖评估。
DOI：
10.3390/molecules18089818
发表时间：
2013-08-16
期刊：
Molecules (Basel, Switzerland)
影响因子：
--
作者：
Arenas P;Peña A;Ríos D;Benites J;Muccioli GG;Calderon PB;Valderrama JA
通讯作者：
Valderrama JA
影响因子：
16.2
作者：
Feng, Rui-Mei;Zong, Yi-Nan;Xu, Rui-Hua
通讯作者：
Xu, Rui-Hua
影响因子：
4.9
作者：
Cheng, Xuefang;Liu, Fang;Hao, Haiping
通讯作者：
Hao, Haiping
影响因子：
1.8
作者：
Deniz, Nahide Gulsah;Ozyurek, Mustafa;Apak, Resat
通讯作者：
Apak, Resat
影响因子：
3.7
作者：
Weerink LBM;Gant CM;van Leeuwen BL;de Bock GH;Kouwenhoven EA;Faneyte IF
通讯作者：
Faneyte IF