一种检测ONOO–的新型荧光探针的构建与细胞成像研究

doi:10.6023/cjoc202203023

有机化学 ›› 2022, Vol. 42 ›› Issue (8): 2428-2432.DOI: 10.6023/cjoc202203023 上一篇下一篇

研究论文

一种检测ONOO^–的新型荧光探针的构建与细胞成像研究

李嘉欣, 贺如艳, 段森林, 黎锦华, 韩校净, 叶勇^*()

郑州大学化学学院郑州 450001

收稿日期:2022-03-12 修回日期:2022-04-21 发布日期:2022-05-26
通讯作者: 叶勇
作者简介:
^† 共同第一作者
基金资助:
郑州大学大学生创新创业训练计划(2021cxcy215); 郑州大学本科生拔尖计划资助项目.

Construction and Cell Imaging Study of a Novel Fluorescent Probe for ONOO^– Detection

Jiaxin Li, Ruyan He, Senlin Duan, Jinhua Li, Xiaojing Han, Yong Ye()

College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2022-03-12 Revised:2022-04-21 Published:2022-05-26
Contact: Yong Ye
About author:
^† These authors contributed equally to this work.
Supported by:
Innovation and Entrepreneurship Training Plan for College Students of Zhengzhou University(2021cxcy215); Top Undergraduates Program of Zhengzhou University

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摘要/Abstract

过氧亚硝酸盐(ONOO^–)作为一种重要的活性氮, 与多种疾病的发生密切相关, 发展检测ONOO^–的方法对于理解其相关生理病理机制具有重要的意义. 以四苯乙烯作为荧光团, 引入吡喃鎓基团作为ONOO^–的特异识别位点, 成功构建一例新型的ONOO^–荧光探针TPE-ONOO. 该探针对ONOO^–具有较好的选择性、较强的抗干扰能力以及较高的灵敏度. 细胞试验表明探针具有较低的细胞毒性, 并成功将其用于细胞外源性和内源性ONOO^–的成像监测. 该新型探针为研究ONOO^–生理过程提供了一种有效的研究工具.

关键词: 荧光探针, ONOO^–, 四苯乙烯, 细胞成像

As an important reactive nitrogen species, peroxynitrite (ONOO^–) is closely related to the occurrence of various diseases. The development of methods to detect ONOO^– is of great significance for understanding its related physiological and pathological mechanisms. A novel ONOO^– fluorescent probe TPE-ONOO was successfully constructed using tetraphenylethylene as a fluorophore and a pyrylium group as the specific recognition site of ONOO^–. The probe showed high selectivity, strong anti-interference ability and high sensitivity to ONOO^–. Cell assays suggested that the probe had low cytotoxicity and was successfully used for imaging monitoring of exogenous and endogenous ONOO^– in cells. The novel probe synthesized here provides an efficient tool for studying ONOO^–physiological processes.

Key words: fluorescent probe, ONOO^–, tetraphenylethylene, cell imaging

引用此文

李嘉欣, 贺如艳, 段森林, 黎锦华, 韩校净, 叶勇. 一种检测ONOO^–的新型荧光探针的构建与细胞成像研究[J]. 有机化学, 2022, 42(8): 2428-2432.

Jiaxin Li, Ruyan He, Senlin Duan, Jinhua Li, Xiaojing Han, Yong Ye. Construction and Cell Imaging Study of a Novel Fluorescent Probe for ONOO^– Detection[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2428-2432.

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图/表 4

图式1. 探针TPE-ONOO的合成路线和识别ONOO–的机理

Scheme 1. Synthetic route of probe TPE-ONOO and its response mechanism for ONOO–

图1. (A)探针TPE-ONOO对ONOO–的紫外-可见光吸收光谱和(B)探针TPE-ONOO (10 µmol/L)响应ONOO– (100 µmol/L)和其他离子(100 µmol/L)的荧光光谱

Figure 1. (A) UV-visible absorption spectrum of probe TPE-ONOO for ONOO– and (B) fluorescence spectra of probe TPE-ONOO (10 µmol/L) in response to ONOO– (100 µmol/L) and other ions (100 µmol/L) pH=7.4, 25 ℃, V(PBS):V(DMSO)=4:6, spectra were tested after adding ONOO– 0.5 h. Excitation: 400 nm, emission: 500 nm.

图2. (A)探针TPE-ONOO (10 µmol/L)响应ONOO– (0~100 µmol/L)的荧光光谱和(B)探针TPE-ONOO在500 nm荧光强度与ONOO–浓度之间的线性关系

Figure 2. (A) Fluorescence spectra of probe TPE-ONOO (10 µmol/L) in response to ONOO– (0~100 µmol/L) and (B) linear relationship between probe TPE-ONOO fluorescence intensity at 500 nm and ONOO– concentration pH=7.4, 25 ℃, V(PBS):V(DMSO)=4:6, spectra were tested after adding ONOO– 0.5 h, Excitation: 400 nm, emission: 500 nm

图3. 探针TPE-ONOO在MCF-7细胞中的荧光成像

Figure 3. Fluorescence imaging of probe TPE-ONOO in MCF-7 cells MCF-7 cells were first co-incubated with the probe TPE-ONOO (10 µmol/L) for 0.5 h, and then imaged under natural light and green light channels. (a1) natural light; (a2) green channel; (a3) overlay of a1 and a2. Imaging was performed under natural light and green channel after adding 50 µmol/L SIN-1 and co-incubating for 0.5 h. (b1) natural light; (b2) green channel; (b3) overlay of b1 and b2. Imaging was performed natural light and green channel after adding 100 µmol/L SIN-1. (c1) natural light; (c2) green channel; (c3) overlap of c1 and c2. Imaging was performed natural light and green channel after adding LPS (10 μg/mL)/IFN-γ (50 ng/mL) staining respectively 4 h. (d1) natural light; (d2) green channel; (d3) overlap of d1 and d2. Excitation: 400 nm, Emission: 450~530 nm. Scale bar: 20 μm

参考文献 22

[1]	Liu, X.; He, L.; Gong, X.; Yang, Y.; Cheng, D.; Peng, J.; Wang, L.; Zhang, X.-B.; Yuan, L. CCS Chem. 2021, 4, 356. doi: 10.31635/ccschem.021.202000679
[2]	Grzelakowska, A.; Zielonka, M.; Debowska, K.; Modrzejewska, J.; Szala, M.; Sikora, A.; Zielonka, J.; Podsiadly, R. Free Radicals Biol. Med. 2021, 169, 24. doi: 10.1016/j.freeradbiomed.2021.04.011
[3]	Ding, Z.; Tan, J.; Feng, G.; Yuan, Z.; Wu, C.; Zhang, X. Chem. Sci. 2017, 8, 5101. doi: 10.1039/C7SC01077J
[4]	Xie, X.; Liu, G.; Su, X.; Li, Y.; Liu, Y.; Jiao, X.; Wang, X.; Tang, B. Anal. Chem. 2019, 91, 6872. doi: 10.1021/acs.analchem.9b01175
[5]	Yang, X.; Zhang, D.; Ye, Y.; Zhao, Y. Coord. Chem. Rev. 2022, 453, 214336. doi: 10.1016/j.ccr.2021.214336
[6]	Zhao, X.; Li, N.; Liu, F.; Gao, C.; Feng, J.; Liu, L.; Guan, X.; Yan, N. Chin. J. Org. Chem. 2020, 40, 4339. (in Chinese) doi: 10.6023/cjoc202007022
	(赵小龙, 李娜, 刘发玉, 高超, 丰久彪, 刘乐平, 关晓琳, 燕娜, 有机化学, 2020, 40, 4339.) doi: 10.6023/cjoc202007022
[7]	Wang, B.; Wang, Y.; Wang, Y.; Zhao, Y.; Yang, C.; Zeng, Z.; Huan, S.; Song, G. Anal. Chem. 2020, 92, 4154. doi: 10.1021/acs.analchem.0c00329
[8]	Liu, F.; Dong, H.; Tian, Y. Analyst 2019, 144, 2150. doi: 10.1039/C9AN00079H
[9]	Li, D.; Chen, H.; Gan, Z.; Sun, J.; Guo, D.; Qu, L. Sens. Actuators, B 2018, 277, 8.
[10]	Liu, Z.; Tian, Y. Sci. Chin. Chem. 2021, 64, 915. doi: 10.1007/s11426-020-9961-3
[11]	Deng, Y.; Feng, G. Anal. Chem. 2020, 92, 14667. doi: 10.1021/acs.analchem.0c03199
[12]	Yin, X.; Feng, W.; Gong, S.; Feng, G. Dyes Pigm. 2020, 172, 107820. doi: 10.1016/j.dyepig.2019.107820
[13]	Xia, Q.; Feng, S.; Hong, J.; Feng, G. Sens. Actuators, B 2021, 337, 129732. doi: 10.1016/j.snb.2021.129732
[14]	Xiong, J.; Wang, W.; Wang, C.; Zhong, C.; Ruan, R.; Mao, Z.; Liu, Z. ACS Sens. 2020, 5, 3237. doi: 10.1021/acssensors.0c01555
[15]	Cheng, D.; Gong, X.; Wu, Q.; Yuan, J.; Lv, Y.; Yuan, L.; Zhang, X. Anal. Chem. 2020, 92, 11396. doi: 10.1021/acs.analchem.0c02277 pmid: 32683859
[16]	Mao, Z.; Xiong, J.; Wang, P.; An, J.; Zhang, F.; Liu, Z.; Kim, J. S. Coord. Chem. Rev. 2022, 454, 214356. doi: 10.1016/j.ccr.2021.214356
[17]	Cheng, D.; Pan, Y.; Wang, L.; Zeng, Z.; Yuan, L.; Zhang, X.; Chang, Y. T. J. Am. Chem. Soc. 2017, 139, 285. doi: 10.1021/jacs.6b10508 pmid: 27996249
[18]	Tian, X.; Zuo, M.; Niu, P.; Wang, K.; Hu, X. Chin. J. Org. Chem. 2020, 40, 1823. (in Chinese) doi: 10.6023/cjoc202003066
	(田雪琪, 左旻瓒, 牛蓬勃, 王开亚, 胡晓玉, 有机化学, 2020, 40, 1823.) doi: 10.6023/cjoc202003066
[19]	Han, T.; Yan, D. Y.; Wu, Q.; Song, N.; Zhang, H. K.; Wang, D. Chin. J. Chem. 2021, 39, 677. doi: 10.1002/cjoc.202000520
[20]	Xu, W.; Yang, Q.; Zeng, J.; Tan, L.; Zhou, L.; Peng, L.; Zhou, Y.; Xie, C.; Luo, K.; Zhang, Z. Sens. Actuators, B 2022, 359, 131565. doi: 10.1016/j.snb.2022.131565
[21]	Kang, M.; Gu, X.; Kwok, R. T. K.; Leung, C. W. T.; Lam, J. W. Y.; Li, F.; Tang, B. Z. Chem. Commun. 2016, 52, 5957. doi: 10.1039/C6CC01797E
[22]	Wang, E.; Zhao, E.; Hong, Y.; Lam, J. W. Y.; Tang, B. Z. J. Mater. Chem. B 2014, 2, 2013. doi: 10.1039/C3TB21675F

一种检测ONOO^–的新型荧光探针的构建与细胞成像研究

Construction and Cell Imaging Study of a Novel Fluorescent Probe for ONOO^– Detection

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一种检测ONOO–的新型荧光探针的构建与细胞成像研究

Construction and Cell Imaging Study of a Novel Fluorescent Probe for ONOO– Detection

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一种检测ONOO^–的新型荧光探针的构建与细胞成像研究

Construction and Cell Imaging Study of a Novel Fluorescent Probe for ONOO^– Detection