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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Main Authors:	Guorui Cao, Kun Yang, Yue Li, Longjiang Huang, Dawei Teng
Format:	Article
Language:	English
Published:	MDPI AG 2016-02-01
Series:	Molecules
Subjects:	macrocycle 4-hydroxyproline azide-alkyne cycloaddition Mitsunobu reaction amide formation anti-tumor activity
Online Access:	http://www.mdpi.com/1420-3049/21/2/212

id	doaj-528b113d9f254525aeb84c79a4c4cc24
record_format	Article
spelling	doaj-528b113d9f254525aeb84c79a4c4cc242020-11-24T22:16:54ZengMDPI AGMolecules1420-30492016-02-0121221210.3390/molecules21020212molecules21020212Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-HydroxyprolineGuorui Cao0Kun Yang1Yue Li2Longjiang Huang3Dawei Teng4College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, ChinaA 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 (IC50 value = 2.55 µmol/L).http://www.mdpi.com/1420-3049/21/2/212macrocycle4-hydroxyprolineazide-alkyne cycloadditionMitsunobu reactionamide formationanti-tumor activity
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Guorui Cao Kun Yang Yue Li Longjiang Huang Dawei Teng
spellingShingle	Guorui Cao Kun Yang Yue Li Longjiang Huang Dawei Teng Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline Molecules macrocycle 4-hydroxyproline azide-alkyne cycloaddition Mitsunobu reaction amide formation anti-tumor activity
author_facet	Guorui Cao Kun Yang Yue Li Longjiang Huang Dawei Teng
author_sort	Guorui Cao
title	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_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_sort	synthetic strategy and anti-tumor activities of macrocyclic scaffolds based on 4-hydroxyproline
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2016-02-01
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 (IC50 value = 2.55 µmol/L).
topic	macrocycle 4-hydroxyproline azide-alkyne cycloaddition Mitsunobu reaction amide formation anti-tumor activity
url	http://www.mdpi.com/1420-3049/21/2/212
work_keys_str_mv	AT guoruicao syntheticstrategyandantitumoractivitiesofmacrocyclicscaffoldsbasedon4hydroxyproline AT kunyang syntheticstrategyandantitumoractivitiesofmacrocyclicscaffoldsbasedon4hydroxyproline AT yueli syntheticstrategyandantitumoractivitiesofmacrocyclicscaffoldsbasedon4hydroxyproline AT longjianghuang syntheticstrategyandantitumoractivitiesofmacrocyclicscaffoldsbasedon4hydroxyproline AT daweiteng syntheticstrategyandantitumoractivitiesofmacrocyclicscaffoldsbasedon4hydroxyproline
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Synthetic Strategy and Anti-Tumor Activities of Macrocyclic Scaffolds Based on 4-Hydroxyproline

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