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一种新型基于硼二吡咯季铵盐的荧光探针:合成、物理性质及活细胞成像

A Novel BODIPY Quaternary Ammonium Salt-Based Fluorescent Probe: Synthesis, Physical Properties, and Live-Cell Imaging.

作者信息

Deng Peng, Xiao Fuyan, Wang Zhou, Jin Guofan

机构信息

The People's Hospital of Danyang, Affiliated Danyang Hospital of Nantong University, Zhenjiang, China.

School of Pharmacy, Jiangsu University, Zhenjiang, China.

出版信息

Front Chem. 2021 Mar 12;9:650006. doi: 10.3389/fchem.2021.650006. eCollection 2021.

DOI:10.3389/fchem.2021.650006
PMID:33777904
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7994363/
Abstract

The development of biological fluorescent probes is of great significance to the field of cancer bio-imaging. However, most current probes within the bulky hydrophobic group have limited application in aqueous medium and restricted imaging under physiological conditions. Herein, we proposed two efficient molecules to study their physical properties and imaging work, and the absorption and fluorescence intensity were collected with varying ions attending in aqueous medium. We enhance the water solubility through the quaternization reaction and form a balance between hydrophilic and hydrophobicity with dipyrrome-theneboron difluoride (BODIPY) fluorophore. We introduced pyridine and dimethylaminopyridine (DMAP) by quaternization and connected the BODIPY fluorophore by ethylenediamine. The final synthesized probes have achieved ideal affinity with HeLa cells (human cervical carcinoma cell line) in live-cell imaging which could be observed by Confocal Microscope. The probes also have a good affinity with subcutaneous tumor cells in mice in imaging, which may make them candidates as oncology imaging probes.

摘要

生物荧光探针的开发对癌症生物成像领域具有重要意义。然而,目前大多数含有庞大疏水基团的探针在水性介质中的应用有限,并且在生理条件下的成像受到限制。在此,我们提出了两种高效分子来研究它们的物理性质和成像效果,并在水性介质中加入不同离子的情况下收集吸收和荧光强度。我们通过季铵化反应提高了水溶性,并与二吡咯亚甲基二氟化硼(BODIPY)荧光团形成了亲水和疏水之间的平衡。我们通过季铵化引入了吡啶和二甲基氨基吡啶(DMAP),并通过乙二胺连接了BODIPY荧光团。最终合成的探针在活细胞成像中与HeLa细胞(人宫颈癌细胞系)实现了理想的亲和力,这可以通过共聚焦显微镜观察到。该探针在小鼠皮下肿瘤细胞成像中也具有良好的亲和力,这可能使它们成为肿瘤成像探针的候选者。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/25419b4534c7/fchem-09-650006-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/a6ba01f7d2e3/FCHEM_fchem-2021-650006_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/3013965c9d47/FCHEM_fchem-2021-650006_gs_sch2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/812b66096791/fchem-09-650006-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/b82e4ddfbdf3/fchem-09-650006-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/cb6df50edb26/fchem-09-650006-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/acb1ba0102a7/fchem-09-650006-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/09edb53dd346/fchem-09-650006-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/25419b4534c7/fchem-09-650006-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/a6ba01f7d2e3/FCHEM_fchem-2021-650006_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/3013965c9d47/FCHEM_fchem-2021-650006_gs_sch2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/812b66096791/fchem-09-650006-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/b82e4ddfbdf3/fchem-09-650006-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/cb6df50edb26/fchem-09-650006-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/acb1ba0102a7/fchem-09-650006-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/09edb53dd346/fchem-09-650006-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8cef/7994363/25419b4534c7/fchem-09-650006-g006.jpg

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2
Bicarbonate suppresses mitochondrial membrane depolarization induced by conventional uncouplers.碳酸氢盐可抑制传统解偶联剂诱导的线粒体膜去极化。
Biochem Biophys Res Commun. 2020 Sep 10;530(1):29-34. doi: 10.1016/j.bbrc.2020.06.131. Epub 2020 Jul 28.
3
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4
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6
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