Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline

A series of novel 13- to 15-member hydroxyproline-based macrocycles, which contain alkyl-alkyl ether and alkyl-aryl ether moieties, have been synthesized by the strategy of macrocyclization utilising azide-alkyne cycloaddition, Mitsunobu protocol and amide formation. Their anti-tumor activities towa...

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Autores principales: Cao, Guorui, Yang, Kun, Li, Yue, Huang, Longjiang, Teng, Dawei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274554/
https://www.ncbi.nlm.nih.gov/pubmed/26891283
http://dx.doi.org/10.3390/molecules21020212
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author Cao, Guorui
Yang, Kun
Li, Yue
Huang, Longjiang
Teng, Dawei
author_facet Cao, Guorui
Yang, Kun
Li, Yue
Huang, Longjiang
Teng, Dawei
author_sort Cao, Guorui
collection PubMed
description A series of novel 13- to 15-member hydroxyproline-based macrocycles, which contain alkyl-alkyl ether and alkyl-aryl ether moieties, have been synthesized by the strategy of macrocyclization utilising azide-alkyne cycloaddition, Mitsunobu protocol and amide formation. Their anti-tumor activities towards A549, MDA-MB-231 and Hep G2 cells were screened in vitro by an MTT assay. The results indicated that 13-member macrocycle 33 containing alkene chain showed the best results, exhibiting the highest inhibitory effects towards lung cancer cell line A549, which was higher than that of the reference cisplatin (IC(50) value = 2.55 µmol/L).
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spelling pubmed-62745542018-12-28 Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline Cao, Guorui Yang, Kun Li, Yue Huang, Longjiang Teng, Dawei Molecules Article A series of novel 13- to 15-member hydroxyproline-based macrocycles, which contain alkyl-alkyl ether and alkyl-aryl ether moieties, have been synthesized by the strategy of macrocyclization utilising azide-alkyne cycloaddition, Mitsunobu protocol and amide formation. Their anti-tumor activities towards A549, MDA-MB-231 and Hep G2 cells were screened in vitro by an MTT assay. The results indicated that 13-member macrocycle 33 containing alkene chain showed the best results, exhibiting the highest inhibitory effects towards lung cancer cell line A549, which was higher than that of the reference cisplatin (IC(50) value = 2.55 µmol/L). MDPI 2016-02-15 /pmc/articles/PMC6274554/ /pubmed/26891283 http://dx.doi.org/10.3390/molecules21020212 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Cao, Guorui
Yang, Kun
Li, Yue
Huang, Longjiang
Teng, Dawei
Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline
title Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline
title_full Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline
title_fullStr Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline
title_full_unstemmed Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline
title_short Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline
title_sort synthetic strategy and anti-tumor activities of macrocyclic scaffolds based on 4-hydroxyproline
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274554/
https://www.ncbi.nlm.nih.gov/pubmed/26891283
http://dx.doi.org/10.3390/molecules21020212
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