Progress of Mitochondria⁃Targeted Near⁃Infrared HClO/ClO- Fluorescent Probes

doi:10.19894/j.issn.1000-0518.210583

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (3): 407-424.DOI: 10.19894/j.issn.1000-0518.210583

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Progress of Mitochondria⁃Targeted Near⁃Infrared HClO/ClO^- Fluorescent Probes

Rui HUANG¹, Chang-Qing YE², Ya-Jun LI², Mong-Feng CHIOU², Da-Liang LI¹(), Hong-Li BAO²()

^1.College of Life Sciences，Fujian Normal University，Fuzhou 350117，China
^2.Key Laboratory of Coal to Ethylene Glycol and Its Related Technology，Fujian Institute of Research on the Structure of Matter，Chinese Academy of Sciences，Fuzhou 350002，China

Received:2021-12-29 Accepted:2022-01-05 Published:2022-03-01 Online:2022-03-15
Contact: Da-Liang LI,Hong-Li BAO
About author:hlbao@fjirsm.ac.cn； daliangli@fjnu.edu.cn
Supported by:
the Innovative Research Teams Program II of Fujian Normal University in China(IRTL1703);the Natural Science Foundation of Fujian Province in China(2021J01205)

Abstract

Abstract:

As an important reactive oxygen species （ROS）， HClO/ClO^- can retrospect to mitochondria and participates in various physiological and pathological processes. Therefore， it is particularly important to develop an effective method to detect HClO/ClO^- in the biology and physiology. Fluorescence analysis has attracted much attention because of its high sensitivity， fast response time， low cost， and easy operation. More importantly， the use of fluorescent probes can visualize the detection process in vitro and in vivo. In recent years， to study the role of hypochlorous acid in cells， many mitochondria-targeted fluorescent HClO/ClO^- probes have been designed and synthesized. Among them， some probes in the short-wavelength region suffer from some shortages， such as high autofluorescence and poor tissue penetration. Therefore， it is of great significance to develop HClO/ClO^- probes with far-infrared to near-infrared emission. This article focuses on the latest developments of mitochondrial-targeted near-infrared fluorescent probes used to detect HClO/ClO^- and summarizes their possible reaction mechanisms which are mainly divided into the oxidation of unsaturated double bonds， the oxidation of thioethers， the oxidation of amino groups or hydrazides and oxidation multi-sites. It is expected to be beneficial to develop the novel specific fluorescent probes in the monitoring of physiological and pathological HClO/ClO^-.

Key words: Mitochondria, Fluorescent probe, Near infrared, Hypochlorous acid

CLC Number:

O652.1

Rui HUANG, Chang-Qing YE, Ya-Jun LI, Mong-Feng CHIOU, Da-Liang LI, Hong-Li BAO. Progress of Mitochondria⁃Targeted Near⁃Infrared HClO/ClO^- Fluorescent Probes[J]. Chinese Journal of Applied Chemistry, 2022, 39(3): 407-424.

Figures/Tables 19

Fig.1 The synthetic route of probe CMBI and the reaction mechanism with ClO-［51］

Fig.2 The reaction mechanism of probe OH-substituted coumarin-hemicyanine dye with ClO-［54］

Fig.3 Synthesis path of probe NSSN［59］

Fig.4 The reaction mechanism of probe NSSN in the presence of HClO［59］

Fig.5 The response mechanism of probe C3H to HClO［64］

Fig.6 Synthesis path of Mito?NCHO and Mito?NClO［65］

Fig.7 The reaction mechanism of Mito?NClO probe to ClO-［65］

Fig.8 The response mechanism of Cy7?NphS probe to HClO and MPO［69］

Fig.9 The response mechanism of probe L to HClO［70］

Fig.10 The response mechanism of probe MXS to HClO［71］

Fig.11 The response mechanism of probe CVS to HClO［76］

Fig.12 The response mechanism of probe NB?OCl to ClO-［80］

Fig.13 The reaction mechanism of probe NCS?BOD?OCH3 to ClO-［81］

Fig.14 The response mechanism of Mito?TP?ClO probe to ClO-［84］

Fig.15 Fluorescence response process of Cy7?Nil fluorescent probe to different concentrations of HClO/ClO-［86］

Fig.16 Synthesis method of probe P?HClO?SO2［48］

Fig.17 The detection of the HClO-SO2 cycle in the mitochondria by the probe P?HClO?SO2［96］

Fig.18 Reaction mechanism of probe D6［62］

Table 1 Probe performance

序号

No.

化合物名称

Compound's name

化合物结构

Compound's structure

荧光量子产率

Quantum yield（Φ）

皮尔森或重叠系数

Pearson's/overlap coefficient

检测限

Detection limit

响应时间

Response time

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Progress of Mitochondria⁃Targeted Near⁃Infrared HClO/ClO^- Fluorescent Probes

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