Design, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core

A series of novel fluorescent 4H-1-benzopyrans was designed and developed as near-infrared fluorescent molecules with a compact donor–acceptor-donor architecture. Spectral intensity of the fluorescent molecules <b>M-1, M-2, M-3</b> varied significantly with the increasing polarities of s...

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Autores principales:	Shuting Wang, Shulei Zhu, Yawen Tanzeng, Yuexing Zhang, Chuchu Li, Mingliang Ma, Wei Lu
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	dye fluorescence intensity environmental sensitivity near-infrared fluorescent molecules potential probe Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/04fe77a638c74e89a92fb52f3423ff36
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spelling	oai:doaj.org-article:04fe77a638c74e89a92fb52f3423ff362021-11-25T18:28:56ZDesign, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core10.3390/molecules262269861420-3049https://doaj.org/article/04fe77a638c74e89a92fb52f3423ff362021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6986https://doaj.org/toc/1420-3049A series of novel fluorescent 4H-1-benzopyrans was designed and developed as near-infrared fluorescent molecules with a compact donor–acceptor-donor architecture. Spectral intensity of the fluorescent molecules <b>M-1, M-2, M-3</b> varied significantly with the increasing polarities of solvents, where <b>M-3</b> showed high viscosity sensitivity in glycerol-ethanol system with a 3-fold increase in emission intensity. Increasing concentrations of compound <b>M-3</b> to 5% BSA in PBS elicited a 4-fold increase in fluorescence intensity, exhibiting a superior environmental sensitivity. Furthermore, the in vitro cellular uptake behavior and CLSM assay of cancer cell lines demonstrated that <b>M-3</b> could easily enter the cell nucleus and bind to proteins with low toxicity. Therefore, the synthesized near-infrared fluorescent molecules could provide a new direction for the development of optical imaging probes and potential further drugs.Shuting WangShulei ZhuYawen TanzengYuexing ZhangChuchu LiMingliang MaWei LuMDPI AGarticledyefluorescence intensityenvironmental sensitivitynear-infrared fluorescent moleculespotential probeOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6986, p 6986 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	dye fluorescence intensity environmental sensitivity near-infrared fluorescent molecules potential probe Organic chemistry QD241-441
spellingShingle	dye fluorescence intensity environmental sensitivity near-infrared fluorescent molecules potential probe Organic chemistry QD241-441 Shuting Wang Shulei Zhu Yawen Tanzeng Yuexing Zhang Chuchu Li Mingliang Ma Wei Lu Design, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core
description	A series of novel fluorescent 4H-1-benzopyrans was designed and developed as near-infrared fluorescent molecules with a compact donor–acceptor-donor architecture. Spectral intensity of the fluorescent molecules <b>M-1, M-2, M-3</b> varied significantly with the increasing polarities of solvents, where <b>M-3</b> showed high viscosity sensitivity in glycerol-ethanol system with a 3-fold increase in emission intensity. Increasing concentrations of compound <b>M-3</b> to 5% BSA in PBS elicited a 4-fold increase in fluorescence intensity, exhibiting a superior environmental sensitivity. Furthermore, the in vitro cellular uptake behavior and CLSM assay of cancer cell lines demonstrated that <b>M-3</b> could easily enter the cell nucleus and bind to proteins with low toxicity. Therefore, the synthesized near-infrared fluorescent molecules could provide a new direction for the development of optical imaging probes and potential further drugs.
format	article
author	Shuting Wang Shulei Zhu Yawen Tanzeng Yuexing Zhang Chuchu Li Mingliang Ma Wei Lu
author_facet	Shuting Wang Shulei Zhu Yawen Tanzeng Yuexing Zhang Chuchu Li Mingliang Ma Wei Lu
author_sort	Shuting Wang
title	Design, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core
title_short	Design, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core
title_full	Design, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core
title_fullStr	Design, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core
title_full_unstemmed	Design, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core
title_sort	design, synthesis, and evaluation of near-infrared fluorescent molecules based on 4h-1-benzopyran core
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/04fe77a638c74e89a92fb52f3423ff36
work_keys_str_mv	AT shutingwang designsynthesisandevaluationofnearinfraredfluorescentmoleculesbasedon4h1benzopyrancore AT shuleizhu designsynthesisandevaluationofnearinfraredfluorescentmoleculesbasedon4h1benzopyrancore AT yawentanzeng designsynthesisandevaluationofnearinfraredfluorescentmoleculesbasedon4h1benzopyrancore AT yuexingzhang designsynthesisandevaluationofnearinfraredfluorescentmoleculesbasedon4h1benzopyrancore AT chuchuli designsynthesisandevaluationofnearinfraredfluorescentmoleculesbasedon4h1benzopyrancore AT mingliangma designsynthesisandevaluationofnearinfraredfluorescentmoleculesbasedon4h1benzopyrancore AT weilu designsynthesisandevaluationofnearinfraredfluorescentmoleculesbasedon4h1benzopyrancore
_version_	1718411056559161344

Design, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core

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