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Synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds
A new approach for the synthesis of podophyllotoxin-naphthoquinone compounds using microwave-assisted three-component reactions is reported in this study. Novel podophyllotoxin-naphthoquinone derivatives with modification on ring E were synthesized. All the synthetic compounds were assessed in terms...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9361925/ https://www.ncbi.nlm.nih.gov/pubmed/36043070 http://dx.doi.org/10.1039/d2ra03312g |
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author | Nguyen, Ha Thanh Nguyen Thi, Quynh Giang Nguyen Thi, Thu Ha Thi, Phuong Hoang Le-Nhat-Thuy, Giang Dang Thi, Tuyet Anh Le-Quang, Bao Pham-The, Hai Van Nguyen, Tuyen |
author_facet | Nguyen, Ha Thanh Nguyen Thi, Quynh Giang Nguyen Thi, Thu Ha Thi, Phuong Hoang Le-Nhat-Thuy, Giang Dang Thi, Tuyet Anh Le-Quang, Bao Pham-The, Hai Van Nguyen, Tuyen |
author_sort | Nguyen, Ha Thanh |
collection | PubMed |
description | A new approach for the synthesis of podophyllotoxin-naphthoquinone compounds using microwave-assisted three-component reactions is reported in this study. Novel podophyllotoxin-naphthoquinone derivatives with modification on ring E were synthesized. All the synthetic compounds were assessed in terms of their cytotoxicity profile against four cancer cell lines (KB, HepG2, A549, and MCF7), and noncancerous Hek-293 cell lines. Notably, treatment of SK-LU-1 cells with compounds 5a and 5b resulted in G2/M phase arrest of the cell cycle, caspase-3/7 activation, and apoptosis. Additionally, molecular docking studies were performed and showed important interaction of two compounds against residues in the colchicine-binding-site of tubulin as well. Taken together, compounds 5a and 5b were identified as potent anticancer agents. |
format | Online Article Text |
id | pubmed-9361925 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-93619252022-08-29 Synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds Nguyen, Ha Thanh Nguyen Thi, Quynh Giang Nguyen Thi, Thu Ha Thi, Phuong Hoang Le-Nhat-Thuy, Giang Dang Thi, Tuyet Anh Le-Quang, Bao Pham-The, Hai Van Nguyen, Tuyen RSC Adv Chemistry A new approach for the synthesis of podophyllotoxin-naphthoquinone compounds using microwave-assisted three-component reactions is reported in this study. Novel podophyllotoxin-naphthoquinone derivatives with modification on ring E were synthesized. All the synthetic compounds were assessed in terms of their cytotoxicity profile against four cancer cell lines (KB, HepG2, A549, and MCF7), and noncancerous Hek-293 cell lines. Notably, treatment of SK-LU-1 cells with compounds 5a and 5b resulted in G2/M phase arrest of the cell cycle, caspase-3/7 activation, and apoptosis. Additionally, molecular docking studies were performed and showed important interaction of two compounds against residues in the colchicine-binding-site of tubulin as well. Taken together, compounds 5a and 5b were identified as potent anticancer agents. The Royal Society of Chemistry 2022-08-09 /pmc/articles/PMC9361925/ /pubmed/36043070 http://dx.doi.org/10.1039/d2ra03312g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Nguyen, Ha Thanh Nguyen Thi, Quynh Giang Nguyen Thi, Thu Ha Thi, Phuong Hoang Le-Nhat-Thuy, Giang Dang Thi, Tuyet Anh Le-Quang, Bao Pham-The, Hai Van Nguyen, Tuyen Synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds |
title | Synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds |
title_full | Synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds |
title_fullStr | Synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds |
title_full_unstemmed | Synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds |
title_short | Synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds |
title_sort | synthesis and biological activity, and molecular modelling studies of potent cytotoxic podophyllotoxin-naphthoquinone compounds |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9361925/ https://www.ncbi.nlm.nih.gov/pubmed/36043070 http://dx.doi.org/10.1039/d2ra03312g |
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