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Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles

Three series of podophyllotoxin derivatives with various nitrogen-containing heterocycles were designed and synthesized. The antitumor activity of these podophyllotoxin derivatives was evaluated in vitro against a panel of human tumor cell lines. The results showed that podophyllotoxin-imidazolium s...

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Autores principales: Yin, Meng, Fang, Yongsheng, Sun, Xiaotong, Xue, Minggao, Zhang, Caimei, Zhu, Zhiyun, Meng, Yamiao, Kong, Lingmei, Myint, Yi Yi, Li, Yan, Zhao, Jingfeng, Yang, Xiaodong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10206303/
https://www.ncbi.nlm.nih.gov/pubmed/37234201
http://dx.doi.org/10.3389/fchem.2023.1191498
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author Yin, Meng
Fang, Yongsheng
Sun, Xiaotong
Xue, Minggao
Zhang, Caimei
Zhu, Zhiyun
Meng, Yamiao
Kong, Lingmei
Myint, Yi Yi
Li, Yan
Zhao, Jingfeng
Yang, Xiaodong
author_facet Yin, Meng
Fang, Yongsheng
Sun, Xiaotong
Xue, Minggao
Zhang, Caimei
Zhu, Zhiyun
Meng, Yamiao
Kong, Lingmei
Myint, Yi Yi
Li, Yan
Zhao, Jingfeng
Yang, Xiaodong
author_sort Yin, Meng
collection PubMed
description Three series of podophyllotoxin derivatives with various nitrogen-containing heterocycles were designed and synthesized. The antitumor activity of these podophyllotoxin derivatives was evaluated in vitro against a panel of human tumor cell lines. The results showed that podophyllotoxin-imidazolium salts and podophyllotoxin-1,2,4-triazolium salts a1–a20 exhibited excellent cytotoxic activity. Among them, a6 was the most potent cytotoxic compound with IC(50) values of 0.04–0.29 μM. Podophyllotoxin-1,2,3-triazole derivatives b1–b5 displayed medium cytotoxic activity, and podophyllotoxin-amine compounds c1–c3 has good cytotoxic activity with IC(50) value of 0.04–0.58 μM. Furthermore, cell cycle and apoptosis experiments of compound a6 were carried out and the results exhibited that a6 could induce G2/M cell cycle arrest and apoptosis in HCT-116 cells.
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spelling pubmed-102063032023-05-25 Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles Yin, Meng Fang, Yongsheng Sun, Xiaotong Xue, Minggao Zhang, Caimei Zhu, Zhiyun Meng, Yamiao Kong, Lingmei Myint, Yi Yi Li, Yan Zhao, Jingfeng Yang, Xiaodong Front Chem Chemistry Three series of podophyllotoxin derivatives with various nitrogen-containing heterocycles were designed and synthesized. The antitumor activity of these podophyllotoxin derivatives was evaluated in vitro against a panel of human tumor cell lines. The results showed that podophyllotoxin-imidazolium salts and podophyllotoxin-1,2,4-triazolium salts a1–a20 exhibited excellent cytotoxic activity. Among them, a6 was the most potent cytotoxic compound with IC(50) values of 0.04–0.29 μM. Podophyllotoxin-1,2,3-triazole derivatives b1–b5 displayed medium cytotoxic activity, and podophyllotoxin-amine compounds c1–c3 has good cytotoxic activity with IC(50) value of 0.04–0.58 μM. Furthermore, cell cycle and apoptosis experiments of compound a6 were carried out and the results exhibited that a6 could induce G2/M cell cycle arrest and apoptosis in HCT-116 cells. Frontiers Media S.A. 2023-05-10 /pmc/articles/PMC10206303/ /pubmed/37234201 http://dx.doi.org/10.3389/fchem.2023.1191498 Text en Copyright © 2023 Yin, Fang, Sun, Xue, Zhang, Zhu, Meng, Kong, Myint, Li, Zhao and Yang. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Yin, Meng
Fang, Yongsheng
Sun, Xiaotong
Xue, Minggao
Zhang, Caimei
Zhu, Zhiyun
Meng, Yamiao
Kong, Lingmei
Myint, Yi Yi
Li, Yan
Zhao, Jingfeng
Yang, Xiaodong
Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles
title Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles
title_full Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles
title_fullStr Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles
title_full_unstemmed Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles
title_short Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles
title_sort synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10206303/
https://www.ncbi.nlm.nih.gov/pubmed/37234201
http://dx.doi.org/10.3389/fchem.2023.1191498
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