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用于体外和体内生物成像的单苯环可点击荧光团

Single-Benzene-Based Clickable Fluorophores for In Vitro and In Vivo Bioimaging.

作者信息

Mohanrao Raja, Pinto Clyde S, Suchenko Andrejus, Clarkson Guy J, Wills Martin, Roesner Stefan, Shipman Michael, Balasubramanian Mohan K

机构信息

Centre for Mechanochemical Cell Biology and Warwick Medical School, Division of Biomedical Science, University of Warwick, CoventryCV4 7AL, UK.

Department of Chemistry, University of Warwick, Gibbet Hill Road, CoventryCV4 7AL, UK.

出版信息

ChemistrySelect. 2025 Feb 27;10(9). doi: 10.1002/slct.202405738. eCollection 2025 Mar.

DOI:10.1002/slct.202405738
PMID:40551966
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7617796/
Abstract

A series of miniaturized, clickable single-benzene-based fluorophores derived from tetrafluoroterephthalonitrile is reported. Fluorophores based on a tetrahydroquinoxaline skeleton exhibited improved photophysical properties due to enhanced electron delocalization between donor and acceptor groups compared to those with a dihydro[1,4]thiazine skeleton. These easily synthesized clickable fluorophores were successfully applied in both in vitro and in vivo bioimaging following protein conjugation.

摘要

报道了一系列由四氟对苯二甲腈衍生的小型化、可点击的单苯基金属荧光团。与具有二氢[1,4]噻嗪骨架的荧光团相比，基于四氢喹喔啉骨架的荧光团由于供体和受体基团之间电子离域的增强而表现出改善的光物理性质。这些易于合成的可点击荧光团在蛋白质偶联后成功应用于体外和体内生物成像。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/1c90311b0eb4/EMS206536-f007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/a02746e96e1e/EMS206536-f001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/9091952eaef4/EMS206536-f002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/9e666b2125d8/EMS206536-f003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/97270b269b9f/EMS206536-f004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/61e5b27d3104/EMS206536-f005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/247c87398c00/EMS206536-f006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/1c90311b0eb4/EMS206536-f007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/a02746e96e1e/EMS206536-f001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/9091952eaef4/EMS206536-f002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/9e666b2125d8/EMS206536-f003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/97270b269b9f/EMS206536-f004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/61e5b27d3104/EMS206536-f005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/247c87398c00/EMS206536-f006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a924/7617796/1c90311b0eb4/EMS206536-f007.jpg

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本文引用的文献

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J Am Chem Soc. 2025 Feb 12;147(6):5258-5268. doi: 10.1021/jacs.4c16087. Epub 2025 Feb 4.
2
Data-driven machine learning models for predicting the maximum absorption and emission wavelengths of single benzene fluorophores.用于预测单个苯荧光团最大吸收和发射波长的数据驱动机器学习模型。
Spectrochim Acta A Mol Biomol Spectrosc. 2025 Feb 5;326:125213. doi: 10.1016/j.saa.2024.125213. Epub 2024 Sep 24.
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Recent advances in minimal fluorescent probes for optical imaging.
近年来光学成像用荧光探针的研究进展。
Curr Opin Chem Biol. 2024 Jun;80:102458. doi: 10.1016/j.cbpa.2024.102458. Epub 2024 Apr 25.
4
Small is Beautiful: Electronic Origin and Synthetic Evolution of Single-Benzene Fluorophores.小即美：单苯荧光团的电子起源与合成进化
Acc Chem Res. 2024 Jan 2;57(1):140-152. doi: 10.1021/acs.accounts.3c00605. Epub 2023 Dec 21.
5
Diamino-Terephthalonitrile-based Single Benzene Fluorophores Featuring Strong Solution State Fluorescence and Large Stokes Shifts.基于二氨基对苯二甲腈的单苯荧光团，具有强溶液态荧光和大斯托克斯位移。
J Org Chem. 2023 Nov 17;88(22):15708-15716. doi: 10.1021/acs.joc.3c01685. Epub 2023 Nov 6.
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