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新型桦木酸-二嗪衍生物作为潜在抗肿瘤药物的设计、合成及细胞毒性评价

Design, synthesis and cytotoxic evaluation of novel betulonic acid-diazine derivatives as potential antitumor agents.

作者信息

Shu Yisong, Li Feifei, Han Yaotian, Wang Penglong, Gao Feng, Yan Mengmeng, Liang Miao, Ma Qiang, Zhang Yuzhong, Ding Xia, Lei Haimin

机构信息

School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, China.

Chinese Academy of Inspection and Quarantine, Beijing, China.

出版信息

Front Chem. 2022 Sep 6;10:969770. doi: 10.3389/fchem.2022.969770. eCollection 2022.

DOI:10.3389/fchem.2022.969770
PMID:36147251
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9486541/
Abstract

With the purpose to improve antiproliferative activity, 26 new betulonic acid-diazine derivatives were designed and synthesized from betulinic acid. The anticancer activity of these semi-synthetic compounds was evaluated by MTT assay in both tumor cell lines and normal cell line. The results indicated that majority of new compounds exhibited improved antitumor activity compared with the parent compound betulonic acid. Compound , in particular, had the most significant action with IC value of 3.39 μM against MCF-7 cells, while it showed lower cytotoxicity on MDCK cell line than cisplatin. Furthermore, we discovered that strongly increased MCF-7 cell damage mostly by influencing arginine and fatty acid metabolism. In addition, the structure-activity relationships were briefly discussed. The results of this study suggested that the introduction of different diazines at C-28 could selectively inhibit different kinds of cancer cells and might be an effective way to synthesize potent anticancer lead compound from betulonic acid.

摘要

为了提高抗增殖活性，从桦木酸设计并合成了26种新的桦木酸 - 二嗪衍生物。通过MTT法在肿瘤细胞系和正常细胞系中评估了这些半合成化合物的抗癌活性。结果表明，与母体化合物桦木酸相比，大多数新化合物表现出改善的抗肿瘤活性。特别是化合物 ，对MCF - 7细胞的IC值为3.39 μM，具有最显著的作用，而其对MDCK细胞系的细胞毒性比顺铂低。此外，我们发现 主要通过影响精氨酸和脂肪酸代谢，强烈增加了MCF - 7细胞损伤。此外，还简要讨论了构效关系。本研究结果表明，在C - 28处引入不同的二嗪可以选择性地抑制不同种类的癌细胞，并且可能是从桦木酸合成强效抗癌先导化合物的有效方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/45f92cbeb342/fchem-10-969770-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/c0262331abe4/fchem-10-969770-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/a5725fb6913c/fchem-10-969770-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/7fd502abba1b/FCHEM_fchem-2022-969770_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/9ef9d19e80d2/fchem-10-969770-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/411d724d6a6a/fchem-10-969770-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/aed3baa96f43/fchem-10-969770-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/8f1b6e360060/fchem-10-969770-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/8ac4503ca366/fchem-10-969770-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/45f92cbeb342/fchem-10-969770-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/c0262331abe4/fchem-10-969770-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/a5725fb6913c/fchem-10-969770-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/7fd502abba1b/FCHEM_fchem-2022-969770_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/9ef9d19e80d2/fchem-10-969770-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/411d724d6a6a/fchem-10-969770-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/aed3baa96f43/fchem-10-969770-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/8f1b6e360060/fchem-10-969770-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/8ac4503ca366/fchem-10-969770-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7e4d/9486541/45f92cbeb342/fchem-10-969770-g008.jpg

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