Semi-synthesis and antitumor activity of 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives
Semi-synthesis and antitumor activity of 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives
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5, 8-O-二甲基酰紫草素衍生物6-异构体的半合成及其抗肿瘤活性
DOI：
10.1016/j.ejmech.2011.05.006
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发表时间：
2011-08-01
影响因子：
6.7
通讯作者：
Li, Shao-Shun
中科院分区：
文献类型：
--
作者：
Zhou, Wen;Zhang, Xu;Li, Shao-Shun
我们最近发现5,8-O-二甲基酰基紫草素衍生物对MCF-7具有选择性，并且对正常细胞无毒性。本文以紫草素为原料合成了一系列相应的5,8-O-二甲基酰基紫草素衍生物的6-异构体。细胞毒性的体外证据表明，大多数化合物比紫草素更具活性或相当，并且保留了针对MCF-7的选择性。 MDA-MB-231对正常细胞没有毒性。另外，位置异构体5p、6c的体内抗癌活性进一步表明，5,8-O-二甲基酰基紫草素衍生物的6-异构体比其相应的2-异构体活性更高。因此，我们可以得出结论，紫草素侧链与5,8-二甲氧基-1,4-萘醌连接的位置与抗肿瘤活性相关。 (C) 2011 Elsevier Masson SAS。版权所有。
We recently discovered that 5, 8-O-dimethyl acylshikonin derivatives displayed the selectivity towards MCF-7 and no toxicity to normal cells. Herein, a series of the corresponding 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives were synthesized starting from shikonin. In vitro evidence of the cytotoxicities indicated that most of thecompounds were more active than or comparative to shikonin and retained the selectivity against MCF-7. MDA-MB-231 besides no toxicity in the normal cells. Also, in vivo anticancer activity of the positional isomers 5p, 6c further showed that 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives were more active than their corresponding 2-isomers. Thus, we may conclude that the position of the side chain of shikonin attached to 5,8-dimethoxy -1,4-naphthoquinone is associated with the antitumor activity. (C) 2011 Elsevier Masson SAS. All rights reserved.