Cargando…

Assembly of 1H-isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging

A novel strategy has been established to assemble a series of single (Z)- or (E)-1H-isoindole derivatives through selectively and sequentially activating carbon–nitrogen triple bonds in a multicomponent system containing various nucleophilic and electrophilic sites. The reaction provides efficient a...

Descripción completa

Detalles Bibliográficos
Autores principales: He, Dandan, Zhuang, Zeyan, Wang, Xu, Li, Jiawei, Li, Jianxiao, Wu, Wanqing, Zhao, Zujin, Jiang, Huanfeng, Tang, Ben Zhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6677114/
https://www.ncbi.nlm.nih.gov/pubmed/31588275
http://dx.doi.org/10.1039/c9sc01035a
_version_ 1783440888809127936
author He, Dandan
Zhuang, Zeyan
Wang, Xu
Li, Jiawei
Li, Jianxiao
Wu, Wanqing
Zhao, Zujin
Jiang, Huanfeng
Tang, Ben Zhong
author_facet He, Dandan
Zhuang, Zeyan
Wang, Xu
Li, Jiawei
Li, Jianxiao
Wu, Wanqing
Zhao, Zujin
Jiang, Huanfeng
Tang, Ben Zhong
author_sort He, Dandan
collection PubMed
description A novel strategy has been established to assemble a series of single (Z)- or (E)-1H-isoindole derivatives through selectively and sequentially activating carbon–nitrogen triple bonds in a multicomponent system containing various nucleophilic and electrophilic sites. The reaction provides efficient access to structurally unique fluorophores with aggregation-induced emission characteristics. These new fluorophores show fluorescence wavelengths and efficiencies that can be modulated and have excellent potential to specifically light up lipid droplets (LDs) in living cells with bright fluorescence, low cytotoxicity and better photostability than commercially available LD-specific dyes.
format Online
Article
Text
id pubmed-6677114
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-66771142019-10-04 Assembly of 1H-isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging He, Dandan Zhuang, Zeyan Wang, Xu Li, Jiawei Li, Jianxiao Wu, Wanqing Zhao, Zujin Jiang, Huanfeng Tang, Ben Zhong Chem Sci Chemistry A novel strategy has been established to assemble a series of single (Z)- or (E)-1H-isoindole derivatives through selectively and sequentially activating carbon–nitrogen triple bonds in a multicomponent system containing various nucleophilic and electrophilic sites. The reaction provides efficient access to structurally unique fluorophores with aggregation-induced emission characteristics. These new fluorophores show fluorescence wavelengths and efficiencies that can be modulated and have excellent potential to specifically light up lipid droplets (LDs) in living cells with bright fluorescence, low cytotoxicity and better photostability than commercially available LD-specific dyes. Royal Society of Chemistry 2019-06-12 /pmc/articles/PMC6677114/ /pubmed/31588275 http://dx.doi.org/10.1039/c9sc01035a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
He, Dandan
Zhuang, Zeyan
Wang, Xu
Li, Jiawei
Li, Jianxiao
Wu, Wanqing
Zhao, Zujin
Jiang, Huanfeng
Tang, Ben Zhong
Assembly of 1H-isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging
title Assembly of 1H-isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging
title_full Assembly of 1H-isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging
title_fullStr Assembly of 1H-isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging
title_full_unstemmed Assembly of 1H-isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging
title_short Assembly of 1H-isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging
title_sort assembly of 1h-isoindole derivatives by selective carbon–nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6677114/
https://www.ncbi.nlm.nih.gov/pubmed/31588275
http://dx.doi.org/10.1039/c9sc01035a
work_keys_str_mv AT hedandan assemblyof1hisoindolederivativesbyselectivecarbonnitrogentriplebondactivationaccesstoaggregationinducedemissionfluorophoresforlipiddropletimaging
AT zhuangzeyan assemblyof1hisoindolederivativesbyselectivecarbonnitrogentriplebondactivationaccesstoaggregationinducedemissionfluorophoresforlipiddropletimaging
AT wangxu assemblyof1hisoindolederivativesbyselectivecarbonnitrogentriplebondactivationaccesstoaggregationinducedemissionfluorophoresforlipiddropletimaging
AT lijiawei assemblyof1hisoindolederivativesbyselectivecarbonnitrogentriplebondactivationaccesstoaggregationinducedemissionfluorophoresforlipiddropletimaging
AT lijianxiao assemblyof1hisoindolederivativesbyselectivecarbonnitrogentriplebondactivationaccesstoaggregationinducedemissionfluorophoresforlipiddropletimaging
AT wuwanqing assemblyof1hisoindolederivativesbyselectivecarbonnitrogentriplebondactivationaccesstoaggregationinducedemissionfluorophoresforlipiddropletimaging
AT zhaozujin assemblyof1hisoindolederivativesbyselectivecarbonnitrogentriplebondactivationaccesstoaggregationinducedemissionfluorophoresforlipiddropletimaging
AT jianghuanfeng assemblyof1hisoindolederivativesbyselectivecarbonnitrogentriplebondactivationaccesstoaggregationinducedemissionfluorophoresforlipiddropletimaging
AT tangbenzhong assemblyof1hisoindolederivativesbyselectivecarbonnitrogentriplebondactivationaccesstoaggregationinducedemissionfluorophoresforlipiddropletimaging