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

doi:10.6023/cjoc202203023

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2428-2432.DOI: 10.6023/cjoc202203023 Previous Articles Next Articles

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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

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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Abstract

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

Cite this article

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

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.

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

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

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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

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 4

References 22

Related Articles 15

Recommended Articles

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Comments

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