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Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives
A series of novel perbutyrylated glycosides of 4β-triazolopodophyllotoxin derivatives were synthesized by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Evaluation of cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) usi...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272287/ https://www.ncbi.nlm.nih.gov/pubmed/25690288 http://dx.doi.org/10.3390/molecules20023255 |
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author | Zi, Cheng-Ting Liu, Zhen-Hua Li, Gen-Tao Li, Yan Zhou, Jun Ding, Zhong-Tao Hu, Jiang-Miao Jiang, Zi-Hua |
author_facet | Zi, Cheng-Ting Liu, Zhen-Hua Li, Gen-Tao Li, Yan Zhou, Jun Ding, Zhong-Tao Hu, Jiang-Miao Jiang, Zi-Hua |
author_sort | Zi, Cheng-Ting |
collection | PubMed |
description | A series of novel perbutyrylated glycosides of 4β-triazolopodophyllotoxin derivatives were synthesized by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Evaluation of cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using the MTT assay shows that some of these glycosylated derivatives have good anticancer activity. Among the synthesized compounds, compound 21a shows the highest activity, with IC(50) values ranging from 0.49 to 6.70 μM, which is more potent than the control drugs etoposide and cisplatin. Compound 21a is characterized by a perbutyrylated α-D(+)-galactosyl residue, the absence of an additional linking spacer between the sugar residue and the triazole ring, as well as a 4'-OH group on the E ring of the podophyllotoxin scaffold. |
format | Online Article Text |
id | pubmed-6272287 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62722872018-12-13 Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives Zi, Cheng-Ting Liu, Zhen-Hua Li, Gen-Tao Li, Yan Zhou, Jun Ding, Zhong-Tao Hu, Jiang-Miao Jiang, Zi-Hua Molecules Article A series of novel perbutyrylated glycosides of 4β-triazolopodophyllotoxin derivatives were synthesized by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Evaluation of cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using the MTT assay shows that some of these glycosylated derivatives have good anticancer activity. Among the synthesized compounds, compound 21a shows the highest activity, with IC(50) values ranging from 0.49 to 6.70 μM, which is more potent than the control drugs etoposide and cisplatin. Compound 21a is characterized by a perbutyrylated α-D(+)-galactosyl residue, the absence of an additional linking spacer between the sugar residue and the triazole ring, as well as a 4'-OH group on the E ring of the podophyllotoxin scaffold. MDPI 2015-02-16 /pmc/articles/PMC6272287/ /pubmed/25690288 http://dx.doi.org/10.3390/molecules20023255 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Zi, Cheng-Ting Liu, Zhen-Hua Li, Gen-Tao Li, Yan Zhou, Jun Ding, Zhong-Tao Hu, Jiang-Miao Jiang, Zi-Hua Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives |
title | Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives |
title_full | Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives |
title_fullStr | Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives |
title_full_unstemmed | Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives |
title_short | Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives |
title_sort | design, synthesis, and cytotoxicity of perbutyrylated glycosides of 4β-triazolopodophyllotoxin derivatives |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272287/ https://www.ncbi.nlm.nih.gov/pubmed/25690288 http://dx.doi.org/10.3390/molecules20023255 |
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