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Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance

It is highly important and challenging to develop donor-acceptor-donor structured small-molecule second near-infrared window (NIR-II) dyes with excellent properties such as water-solubility and chem/photostability. Here, we discovery an electron acceptor, 6,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4...

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Autores principales: Ji, Aiyan, Lou, Hongyue, Qu, Chunrong, Lu, Wanglong, Hao, Yifan, Li, Jiafeng, Wu, Yuyang, Chang, Tonghang, Chen, Hao, Cheng, Zhen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9250501/
https://www.ncbi.nlm.nih.gov/pubmed/35780137
http://dx.doi.org/10.1038/s41467-022-31521-y
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author Ji, Aiyan
Lou, Hongyue
Qu, Chunrong
Lu, Wanglong
Hao, Yifan
Li, Jiafeng
Wu, Yuyang
Chang, Tonghang
Chen, Hao
Cheng, Zhen
author_facet Ji, Aiyan
Lou, Hongyue
Qu, Chunrong
Lu, Wanglong
Hao, Yifan
Li, Jiafeng
Wu, Yuyang
Chang, Tonghang
Chen, Hao
Cheng, Zhen
author_sort Ji, Aiyan
collection PubMed
description It is highly important and challenging to develop donor-acceptor-donor structured small-molecule second near-infrared window (NIR-II) dyes with excellent properties such as water-solubility and chem/photostability. Here, we discovery an electron acceptor, 6,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TQT) with highest stability in alkaline conditions, compared with conventional NIR-II building block benzobisthiadiazole (BBT) and 6,7-diphenyl-[1,2,5] thiadiazolo[3,4-g]quinoxaline (PTQ). The sulfonated hydrophilic dye, FT-TQT, is further synthesized with 2.13-fold increased quantum yield than its counterpart FT-BBT with BBT as acceptor. FT-TQT complexed with FBS is also prepared and displays a 16-fold increase in fluorescence intensity compared to FT-TQT alone. It demonstrates real-time cerebral and tumor vessel imaging capability with µm-scale resolution. Dynamic monitoring of tumor vascular disruption after drug treatment is achieved by NIR-II fluorescent imaging. Overall, TQT is an efficient electron acceptor for designing innovative NIR-II dyes. The acceptor engineering strategy provides a promising approach to design next generation of NIR-II fluorophores which open new biomedical applications.
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spelling pubmed-92505012022-07-04 Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance Ji, Aiyan Lou, Hongyue Qu, Chunrong Lu, Wanglong Hao, Yifan Li, Jiafeng Wu, Yuyang Chang, Tonghang Chen, Hao Cheng, Zhen Nat Commun Article It is highly important and challenging to develop donor-acceptor-donor structured small-molecule second near-infrared window (NIR-II) dyes with excellent properties such as water-solubility and chem/photostability. Here, we discovery an electron acceptor, 6,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TQT) with highest stability in alkaline conditions, compared with conventional NIR-II building block benzobisthiadiazole (BBT) and 6,7-diphenyl-[1,2,5] thiadiazolo[3,4-g]quinoxaline (PTQ). The sulfonated hydrophilic dye, FT-TQT, is further synthesized with 2.13-fold increased quantum yield than its counterpart FT-BBT with BBT as acceptor. FT-TQT complexed with FBS is also prepared and displays a 16-fold increase in fluorescence intensity compared to FT-TQT alone. It demonstrates real-time cerebral and tumor vessel imaging capability with µm-scale resolution. Dynamic monitoring of tumor vascular disruption after drug treatment is achieved by NIR-II fluorescent imaging. Overall, TQT is an efficient electron acceptor for designing innovative NIR-II dyes. The acceptor engineering strategy provides a promising approach to design next generation of NIR-II fluorophores which open new biomedical applications. Nature Publishing Group UK 2022-07-02 /pmc/articles/PMC9250501/ /pubmed/35780137 http://dx.doi.org/10.1038/s41467-022-31521-y Text en © The Author(s) 2022, corrected publication 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Ji, Aiyan
Lou, Hongyue
Qu, Chunrong
Lu, Wanglong
Hao, Yifan
Li, Jiafeng
Wu, Yuyang
Chang, Tonghang
Chen, Hao
Cheng, Zhen
Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance
title Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance
title_full Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance
title_fullStr Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance
title_full_unstemmed Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance
title_short Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance
title_sort acceptor engineering for nir-ii dyes with high photochemical and biomedical performance
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9250501/
https://www.ncbi.nlm.nih.gov/pubmed/35780137
http://dx.doi.org/10.1038/s41467-022-31521-y
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