Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin,Journal of Natural Products

当前位置： X-MOL 学术 › J. Nat. Prod. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-08-07 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00105
Olga V. Tsepaeva ₁ , Andrey V. Nemtarev _{1,

2} , Timur I. Abdullin ₂ , Leysan R. Grigor’eva ₂ , Elena V. Kuznetsova ₂ , Rezeda A. Akhmadishina ₂ , Liliya E. Ziganshina ₂ , Hanh H. Cong ₂ , Vladimir F. Mironov _{1,

2}

Affiliation

A series of new triphenylphosphonium (TPP) derivatives of the triterpenoid betulin (1, 3-lup-20(29)-ene-3β,28-diol) have been synthesized and evaluated for cytotoxic effects against human breast cancer (MCF-7), prostate adenocarcinoma (PC-3), vinblastine-resistant human breast cancer (MCF-7/Vinb), and human skin fibroblast (HSF) cells. The TPP moiety was applied as a carrier group through the acyl linker at the 28- or 3- and 28-positions of betulin to promote cellular and mitochondrial accumulation of the resultant compounds. A structure–activity relationship study has revealed the essential role of the TPP group in the biological properties of the betulin derivatives produced. The present results showed that a conjugate of betulin with TPP (3) enhanced antiproliferative activity toward vinblastine-resistant MCF-7 cells, with an IC₅₀ value as low as 0.045 μM.

中文翻译：

三萜类桦蛋白的三苯基phosph衍生物的设计，合成和癌细胞生长抑制活性

一系列的三萜桦木醇（新三苯基鏻（TPP）衍生物1，3- LUP-20（29） -烯3β，28-二醇）已被合成并评价针对人乳腺癌细胞毒性作用（MCF-7），前列腺腺癌（PC-3），耐长春碱的人乳腺癌（MCF-7 / Vinb）和人皮肤成纤维细胞（HSF）细胞。该TPP部分通过在白桦蛋白的28-或3-和28-位上的酰基连接基作为载体基团被施加，以促进所得化合物的细胞和线粒体积累。构效关系研究表明，TPP基团在所产生的甜菜素衍生物的生物学特性中起着至关重要的作用。目前的结果表明，白桦素与TPP的结合物（3）增强了对长春碱耐药MCF-7细胞的抗增殖活性，IC ₅₀值低至0.045μM。

更新日期：2017-08-07

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11