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Synthesis and antitumor evaluation of neolaxiflorin B inspired compounds
BACKGROUND: Neolaxiflorin B is derived from ent-kaurane like laxiflorin J and eriocalyxin B with a relatively low potency as an antitumor agent. During preliminary structure–activity relationship studies, the α,β-unsaturated ketone (enone) system is an important active group. METHODS: Seven neolaxif...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Dove
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6712212/ https://www.ncbi.nlm.nih.gov/pubmed/31692523 http://dx.doi.org/10.2147/DDDT.S202345 |
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author | Liu, Jing-Ping Xiao, Ye-Zhi Hu, Yu Li, Xiao-Nian Wu, Ming-Jiang Zhao, Yong Zhao, Yan Ma, Ze-Jin Shen, Jing |
author_facet | Liu, Jing-Ping Xiao, Ye-Zhi Hu, Yu Li, Xiao-Nian Wu, Ming-Jiang Zhao, Yong Zhao, Yan Ma, Ze-Jin Shen, Jing |
author_sort | Liu, Jing-Ping |
collection | PubMed |
description | BACKGROUND: Neolaxiflorin B is derived from ent-kaurane like laxiflorin J and eriocalyxin B with a relatively low potency as an antitumor agent. During preliminary structure–activity relationship studies, the α,β-unsaturated ketone (enone) system is an important active group. METHODS: Seven neolaxiflorin B derivatives containing α,β-unsaturated ketone moieties were synthesized. In vitro, activity was evaluated against three human tumor cell lines and a rat myogenic cell line (HepG2, NSCLC-H292, SNU-1040, and L6, respectively) by MTT assay. RESULTS: Compound 15 appeared a promising antitumor lead due to its cytotoxic potency and relatively high selectivity, with an SI value of 13.14. Flow cytometry analysis was conducted to show that NSCLC-H292 cells were blocked in the G0/G1 phase in the presence of compound 15, thus inhibiting the proliferation of tumor cells. CONCLUSION: This study has revealed that compound 15 is a promising antitumor lead due to the cytotoxic potencies and the high selectivity it displayed when compared to natural counterparts. |
format | Online Article Text |
id | pubmed-6712212 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Dove |
record_format | MEDLINE/PubMed |
spelling | pubmed-67122122019-11-05 Synthesis and antitumor evaluation of neolaxiflorin B inspired compounds Liu, Jing-Ping Xiao, Ye-Zhi Hu, Yu Li, Xiao-Nian Wu, Ming-Jiang Zhao, Yong Zhao, Yan Ma, Ze-Jin Shen, Jing Drug Des Devel Ther Original Research BACKGROUND: Neolaxiflorin B is derived from ent-kaurane like laxiflorin J and eriocalyxin B with a relatively low potency as an antitumor agent. During preliminary structure–activity relationship studies, the α,β-unsaturated ketone (enone) system is an important active group. METHODS: Seven neolaxiflorin B derivatives containing α,β-unsaturated ketone moieties were synthesized. In vitro, activity was evaluated against three human tumor cell lines and a rat myogenic cell line (HepG2, NSCLC-H292, SNU-1040, and L6, respectively) by MTT assay. RESULTS: Compound 15 appeared a promising antitumor lead due to its cytotoxic potency and relatively high selectivity, with an SI value of 13.14. Flow cytometry analysis was conducted to show that NSCLC-H292 cells were blocked in the G0/G1 phase in the presence of compound 15, thus inhibiting the proliferation of tumor cells. CONCLUSION: This study has revealed that compound 15 is a promising antitumor lead due to the cytotoxic potencies and the high selectivity it displayed when compared to natural counterparts. Dove 2019-08-23 /pmc/articles/PMC6712212/ /pubmed/31692523 http://dx.doi.org/10.2147/DDDT.S202345 Text en © 2019 Liu et al. http://creativecommons.org/licenses/by-nc/3.0/ This work is published and licensed by Dove Medical Press Limited. The full terms of this license are available at https://www.dovepress.com/terms.php and incorporate the Creative Commons Attribution – Non Commercial (unported, v3.0) License (http://creativecommons.org/licenses/by-nc/3.0/). By accessing the work you hereby accept the Terms. Non-commercial uses of the work are permitted without any further permission from Dove Medical Press Limited, provided the work is properly attributed. For permission for commercial use of this work, please see paragraphs 4.2 and 5 of our Terms (https://www.dovepress.com/terms.php). |
spellingShingle | Original Research Liu, Jing-Ping Xiao, Ye-Zhi Hu, Yu Li, Xiao-Nian Wu, Ming-Jiang Zhao, Yong Zhao, Yan Ma, Ze-Jin Shen, Jing Synthesis and antitumor evaluation of neolaxiflorin B inspired compounds |
title | Synthesis and antitumor evaluation of neolaxiflorin B inspired compounds |
title_full | Synthesis and antitumor evaluation of neolaxiflorin B inspired compounds |
title_fullStr | Synthesis and antitumor evaluation of neolaxiflorin B inspired compounds |
title_full_unstemmed | Synthesis and antitumor evaluation of neolaxiflorin B inspired compounds |
title_short | Synthesis and antitumor evaluation of neolaxiflorin B inspired compounds |
title_sort | synthesis and antitumor evaluation of neolaxiflorin b inspired compounds |
topic | Original Research |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6712212/ https://www.ncbi.nlm.nih.gov/pubmed/31692523 http://dx.doi.org/10.2147/DDDT.S202345 |
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