反应型HClO/ClO-荧光探针的研究进展

doi:10.16085/j.issn.1000-6613.2020-1297

摘要/Abstract

摘要：

次氯酸/次氯酸根是活性氧化物中重要的信号分子，在生物医药和环境安全等方面发挥着重要作用。反应型荧光探针基于出色的灵敏度、实时成像和生物兼容性好等特点，广泛应用于HClO/ClO^-的检测。本文评述了近5年反应型HClO/ClO^-荧光探针的研究进展，包括反应型HClO/ClO^-荧光探针的设计策略和识别机理，并从HClO/ClO^-引发的反应机理角度（碳碳双键的反应、硫族化合物的反应、醛肟基团的反应、腙/席夫碱的反应、酰肼/磺酰肼的反应、N,N-二甲基硫代氨基甲酸酯的反应和苯硼酸/硼酸酯的反应）概述了反应型HClO/ClO^-荧光探针的特点和实际应用，指出反应型HClO/ClO^-荧光探针的发展方向是合成性能优异的识别基团，构建选择性好、水溶性好、低荧光背景、光化学性能稳定和生物毒性低的反应型近红外HClO/ClO^-荧光探针，实现对生物体内外HClO/ClO^-的可视化检测及机理探索。

关键词: 次氯酸根, 荧光探针, 检测, 应用, 可视化

Abstract:

As one of the most vital reactive oxygen species, hypochlorous acid (HClO)/hypochlorite (ClO^-) plays an indispensable role in biology, medicine and environmental safety. Nowadays, a growing number of reaction-based fluorescent probes have been successfully developed for detecting and imaging HClO/ClO^- with excellent sensitivity, real time image and superior biocompatibility. In this paper, the research process of reaction-based fluorescent probes for HClO/ClO^- was reviewed in the last five years, including design strategies, recognition mechanisms and the characteristics and practical application of reaction-based HClO/ClO^- fluorescent probes based on the hypochlorous acid/hypochlorite-triggered response mechanisms including reaction of the C＝C double bond, chalcogenide, aldoxime group, hydrazine/Schiff, acylhydrazine/sulfonylhydrazine, N,N-dimethylthiocarbamate and phenylo boric acid/boronic acid ester. In the future, it is desired to develop novel detection groups, explore recognition mechanisms, synthetize novel NIR reaction-based fluorescent probes with well selectivity, excellent water solubility, low background fluorescence, stable photochemical property and low biological toxicity, so as to visualize and detect HClO/ClO^-in vitro and in vivo.

Key words: hypochlorite, fluorescent probe, detecting, application, visualize

中图分类号:

TP 212.2

安宁, 高云玲. 反应型HClO/ClO^-荧光探针的研究进展[J]. 化工进展, 2021, 40(6): 3346-3362.

AN Ning, GAO Yunling. Reaction-based fluorescent probes for detection of HClO/ClO^-[J]. Chemical Industry and Engineering Progress, 2021, 40(6): 3346-3362.

图/表 26

参考文献 93

1	HUO Fangjun, ZHANG Jingjing, YANG Yutao, et al. A fluorescein-based highly specific colorimetric and fluorescent probe for hypochlorites in aqueous solution and its application in tap water[J]. Sensors and Actuators B: Chemical, 2012, 166-167: 44-49.
2	ZHANG Dengqing. Highly selective and sensitive colorimetric probes for hypochlorite anion based on azo derivatives[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2010, 77(2): 397-401.
3	CHEN Hong, SUN Tao, QIAO Xiaoguang, et al. Red-emitting fluorescent probe for detecting hypochlorite acid in vitro and in vivo[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, 204: 196-202.
4	LI Gang, JI Dandan, ZHANG Shuman, et al. A mitochondria-targeting fluorescence turn-on probe for hypochlorite and its applications for in vivo imaging[J]. Sensors and Actuators B: Chemical, 2017, 252: 127-133.
5	HAN Danjuan, QIAN Manping, GAO Hongfang, et al. A "switch-on" photoluminescent and electrochemiluminescent multisignal probe for hypochlorite via a cyclometalated iridium complex[J]. Analytica Chimica Acta, 2019, 1074: 98-107.
6	WU S M, PIZZO S V. α₂-Macroglobulin from rheumatoid arthritis synovial fluid: functional analysis defines a role for oxidation in inflammation[J]. Archives Biochemistry and Biophysics, 2001, 391(1): 119-126.
7	STEINBECK M J, NESTI L J, SHARKEY P F, et al. Myeloperoxidase and chlorinated peptides in osteoarthritis: potential biomarkers of the disease[J]. Journal of Orthopaedic Research, 2007, 25(9): 1128-1135.
8	Yannwan YAP, WHITEMAN M, CHEUNG Namsang. Chlorinative stress: an under appreciated mediator of neurodegeneration?[J]. Cellular Signalling, 2007,19(2): 219-228.
9	SUGIYAMA S, KUGIYAMA K, AIKAWA M, et al. Hypochlorous acid, a macrophage product, induces endothelial apoptosis and tissue factor expression: involvement of myeloperoxidase-mediated oxidant in plaque erosion and thrombogenesis[J]. Arteriosclerosis, Thrombosis, and Vascular Biology, 2004, 24(7): 1309-1314.
10	CHEN Weichieh, VENKATESAN P, WU Shupao. A highly selective turn-on fluorescent probe for hypochlorous acid based on hypochlorous acid-induced oxidative intramolecular cyclization of boron dipyrromethene-hydrazone[J]. Analytica Chimica Acta, 2015, 882: 68-75.
11	JACKSON D S, CROCKETT D F, WOLNIK K A. The indirect detection of bleach (sodium hypochlorite) in beverages as evidence of product tampering[J]. Journal of Forensic Sciences, 2006, 51(4): 827-831.
12	MA Zhiwei, WANG Xiao, WANG Chuanchuan, et al. A sensitive and selective fluorescence probe for detection of hypochlorite (OCl^-) and its bioimaging in live cells[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 213: 370-374.
13	ORDEIG O, MAS R, GONZALO J, et al. Continuous detection of hypochlorous acid/hypochlorite for water quality monitoring and control[J]. Electroanalysis, 2005, 17(18): 1641-1648.
14	SOLDATKIN A P, GORCHKOV D V, MARTELET C, et al. New enzyme potentiometric sensor for hypochlorite species detection[J]. Sensors and Actuators B: Chemical, 1997, 43(1/2/3): 99-104.
15	ZHANG Jia, WANG Xiaolei, YANG Xiurong. Colorimetric determination of hypochlorite with unmodified gold nanoparticles through the oxidation of a stabilizer thiol compound[J]. The Analyst, 2012, 137(12): 2806-2812.
16	LI Wei, JIANG Chao, LU Sheng, et al. A hydrogel microsphere-based sensor for dual and highly selective detection of Al³⁺ and Hg²⁺[J]. Sensors and Actuators B: Chemical, 2020, 321: 128490.
17	WANG Kaijie, KONG Qing, CHEN Xiaoqiang, et al. A bifunctional rhodamine derivative as chemosensor for recognizing Cu²⁺ and Hg²⁺ ions via different spectra[J]. Chinese Chemical Letters, 2020, 31(5): 1087-1090.
18	LI Hao, YANG Youzhe, QI Xiaoyi, et al. Design and applications of a novel fluorescent probe for detecting glutathione in biological samples[J]. Analytica Chimica Acta, 2020, 1117: 18-24.
19	MA Qiujuan, WANG Chunyan, BAI Yu, et al. A lysosome-targetable and ratiometric fluorescent probe for hypochlorous acid in living cells based on a 1,8-naphthalimide derivative[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 223: 117334.
20	NGUYEN Vannghia, Seonye HEO, KIM Sangin, et al. A thiocoumarin-based turn-on fluorescent probe for hypochlorite detection and its application to live-cell imaging[J]. Sensors and Actuators B: Chemical, 2020, 317: 128213.
21	GU Bowen, DONG Chao, SHEN Ruwei, et al. Dioxetane-based chemiluminescent probe for fluoride ion-sensing in aqueous solution and living imaging[J]. Sensors and Actuators B: Chemical, 2019, 301: 127111.
22	ZHANG Zijian, Ting LYU, TAO Binbin, et al. A novel fluorescent probe based on naphthalimide for imaging nitroreductase (NTR) in bacteria and cells[J]. Bioorganic & Medicinal Chemistry, 2020, 28(3): 115280.
23	WU Ying, ZHANG Yuhuan, WANG Lan, et al. A simple ratiometric fluorescent sensor selectively compatible of different combinations of characteristic groups for identification of glutathione, cysteine and homocysteine[J]. Sensors and Actuators B: Chemical, 2020, 302: 127181.
24	WANG Dejia, FAN Xiaopeng, SUN Shiguo, et al. Substituent effect: a new strategy to construct a ratiometric fluorescent probe for detection of Al³⁺ and imaging in vivo[J]. Sensors and Actuators B: Chemical, 2018, 264: 304-311.
25	WEN Jia, LI Weisi, LI Jiaqi, et al. Study on rolling circle amplification of Ebola virus and fluorescence detection based on graphene oxide[J]. Sensors and Actuators B: Chemical, 2016, 227: 655-659.
26	王少静, 李长伟, 李锦, 等. 新型香豆素类氟离子荧光探针的合成及细胞成像研究[J]. 化学学报, 2017, 75(4): 383-390.
	WANG Shaojing, LI Changwei, LI Jin, et al. Novel coumarin-based fluorescent probes for detecting fluoride ions in living cells[J]. Acta Chimica Sinica, 2017, 75(4): 383-390.
27	熊麟, 凡勇, 张凡. 稀土纳米晶用于近红外区活体成像和传感研究进展[J]. 化学学报, 2019, 77(12): 1239-1249.
	XIONG Lin, FAN Yong, ZHANG Fan. Research progress on rare earth nanocrystals for in vivo imaging and sensing in near infrared region[J]. Acta Chimica Sinica, 2019, 77(12): 1239-1249.
28	孙世国, 彭孝军, 凡明文, 等. 铼联吡啶系列光敏染料的研究[J]. 有机化学, 2004, 24(8): 953-956.
	SUN Shiguo, PENG Xiaojun, FAN Mingwen, et al. Studies on a series of rhenium(I) bipyridyl photosensitive dyes[J]. Chinese Journal of Organic Chemistry, 2004, 24(8): 953-956.
29	施锋, 李宏洋, 彭孝军, 等. 一种带有酯基并键合电子给体的新型Ru(bpy)₃的设计、合成及光谱和电化学性能[J]. 化学学报, 2004, 62(7): 713-719.
	SHI Feng, LI Hongyang, PENG Xiaojun, et al. Synthesis and spectral properties of a new ruthenium(II) tris-bipyridine with four ester groups and substituted phenol[J]. Acta Chimica Sinica, 2004, 62(7): 713-719.
30	SHEPHERD J, HILDERBRAND S A, WATERMAN P, et al. A fluorescent probe for the detection of myeloperoxidase activity in atherosclerosis-associated macrophages[J]. Chemistry & Biology, 2007, 14(11): 1221-1231.
31	LIU Ying, ZHAO Zhimin, MIAO Junying, et al. A ratiometric fluorescent probe based on boron dipyrromethene and rhodamine Förster resonance energy transfer platform for hypochlorous acid and its application in living cells[J]. Analytica Chimica Acta, 2016, 921: 77-83.
32	NIE Kaixuan, DONG Bo, SHI Huanhuan, et al. Facile construction of AIE-based FRET nanoprobe for ratiometric imaging of hypochlorite in live cells[J]. Journal of Luminescence, 2020, 220: 117018.
33	TONG Lulu, QIAN Ying. A naphthalimide-rhodamine chemodosimeter for hypochlorite based on TBET: high quantum yield and endogeous imaging in living cells[J]. Journal of Photochemistry & Photobiology A: Chemistry, 2019, 368: 62-69.
34	CHEN Liyan, PARK Sangjun, WU Di, et al. A two-photon ESIPT based fluorescence probe for specific detection of hypochlorite[J]. Dyes and Pigments, 2018, 158: 526-532.
35	LIU Shuzhi, YANG Di, LIU Yijiang, et al. A dual-channel and fast-response fluorescent probe for selective detection of HClO and its applications in live cells[J]. Sensors and Actuators B: Chemical, 2019, 299: 126937.
36	WU Wenli, ZHAO Xuan, XI Longlong, et al. A mitochondria-targeted fluorescence probe for ratiometric detection of endogenous hypochlorite in the living cells[J]. Analytica Chimica Acta, 2017, 950: 178-183.
37	WANG Wei, NING Junya, LIU Jinting, et al. A mitochondria-targeted ratiometric fluorescence sensor for the detection of hypochlorite in living cells[J]. Dyes and Pigments, 2019, 171: 107708.
38	HU Qiao, QIN Caiqin, HUANG Lei, et al. Selective visualization of hypochlorite and its fluctuation in cancer cells by a mitochondria-targeting ratiometric fluorescent probe[J]. Dyes and Pigments, 2018, 149: 253-260.
39	ZHANG Qian, ZHANG Peng, GONG Yan, et al. Two-photon AIE based fluorescent probe with large stokes shift for selective and sensitive detection and visualization of hypochlorite[J]. Sensors and Actuators B: Chemical, 2019, 278: 73-81.
40	YAN Yehao, MA Hanlin, MIAO Junying, et al. A ratiometric fluorescence probe based on a novel recognition mechanism for monitoring endogenous hypochlorite in living cells[J]. Analytica Chimica Acta, 2019, 1064: 87-93.
41	YANG Xin, SUN Mingtai, WANG Tian, et al. A smartphone-based portable analytical system for on-site quantification of hypochlorite and its scavenging capacity of antioxidants[J]. Sensors and Actuators B: Chemical, 2019, 283: 524-531.
42	LI Jianping, XIA Shuang, ZHANG Hua, et al. Three-input “and-type” fluorescent logic gate as ratio probe for specific imaging of hypochlorite in rough endoplasmic reticulum[J]. Sensors and Actuators B: Chemical, 2018, 255: 622-629.
43	GAO Liangliang, WANG Wanwan, WU Weina, et al. Sensitive and selective fluorescent probe for hypochlorite in 100% aqueous solution and its application for lysosome-targetable cell imaging[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, 231: 118110.
44	VEDAMALAI M, KEDARIA D, VASITA R, et al. Oxidation of phenothiazine based fluorescent probe for hypochlorite and its application to live cell imaging[J]. Sensors and Actuators B: Chemical, 2018, 263: 137-142.
45	WANG Chengjun, QIAN Ying. A TICT-active orthogonal D-A type probe phenothiazine-BODIPY for ratiometric response of hypochlorite and its application in living cells[J]. Journal of Luminescence, 2019, 210: 261-268.
46	SONG Haohan, ZHOU Yanmei, XU Chenggong, et al. A dual-function fluorescent probe: sensitive detection of water content in commercial products and rapid detection of hypochlorite with a large Stokes shift[J]. Dyes and Pigments, 2019, 162: 160-167.
47	JIN Yue, Minghuan LYU, TAO Yuanfang, et al. A water-soluble BODIPY-based fluorescent probe for rapid and selective detection of hypochlorous acid in living cells[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 219: 569-575.
48	CHOI Myunggil, Hyein RYU, Minjeoung CHO, et al. Dual signaling of hypochlorite in tap water by selective oxidation of phenylselenylated dichlorofluorescein[J]. Sensors and Actuators B: Chemical, 2017, 244: 307-313.
49	LOU Zhangrong, LI Peng, PAN Qiang, et al. A reversible fluorescent probe for detecting hypochloric acid in living cells and animals: utilizing a novel strategy for effectively modulating the fluorescence of selenide and selenoxide[J]. Chemical Communications, 2013, 49(24): 2445-2447.
50	SUN Chunlong, DU Wen, WANG Peng, et al. A novel mitochondria-targeted two-photon fluorescent probe for dynamic and reversible detection of the redox cycles between peroxynitrite and glutathione[J]. Biochemical and Biophysical Research Communications, 2017, 494(3/4): 518-525.
51	WANG Bingshuai, LI Peng, YU Fabiao, et al. A reversible fluorescence probe based on Se-BODIPY for the redox cycle between HClO oxidative stress and H₂S repair in living cells[J]. Chemical Communications, 2013, 49(10): 1014-1016.
52	SHI Wenjing, HUANG Yan, LIU Wancui, et al. A BODIPY-based “off-on” fluorescent probe for fast and selective detection of hypochlorite in living cells[J]. Dyes and Pigments, 2019, 170: 107566.
53	GAO Yunling, PAN Yong, CHI Yu, et al. A reactive turn-on fluorescence probe for hypochlorous acid and its bioimaging application[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 206: 190-196.
54	XU Xiuxiu, QIAN Ying. A novel pyridyl triphenylamine-BODIPY aldoxime: naked-eye visible and fluorometric chemodosimeter for hypochlorite[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2017, 183: 356-361.
55	HU Cunjie, LI Jianping, YAN Liqiang. A fluorescent probe for hypochlorite with colorimetric and fluorometric characteristics and imaging in living cells[J]. Analytical Biochemistry, 2019, 566: 32-36.
56	HAN Juan, LI Yuanyuan, WANG Yun, et al. A water-soluble fluorescent probe for monitoring hypochlorite in water and in living cells[J]. Sensors and Actuators B: Chemical, 2018, 273: 778-783.
57	LI Daoxue, FENG Yan, LIN Jizhi, et al. A mitochondria-targeted two-photon fluorescent probe for highly selective and rapid detection of hypochlorite and its bio-imaging in living cells[J]. Sensors and Actuators B: Chemical, 2016, 222: 483-491.
58	GUO Bingpeng, NIE Hailiang, YANG Wen, et al. A highly sensitive and rapidly responding fluorescent probe with a large Stokes shift for imaging intracellular hypochlorite[J]. Sensors and Actuators B: Chemical, 2016, 236: 459-465.
59	HOU Linxi, SHANGGUAN Mingqin, LU Zhen, et al. A cyclometalated iridium(III) complex-based fluorescence probe for hypochlorite detection and its application by test strips[J]. Analytical Biochemistry, 2019, 566: 27-31.
60	MALKONDU S, ERDEMIR S, KARAKURT S. Red and blue emitting fluorescent probe for cyanide and hypochlorite ions: biological sensing and environmental analysis[J]. Dyes and Pigments, 2020, 174: 108019.
61	NING Yaoyao, CUI Jihong, LU Yiwei, et al. De novo design and synthesis of a novel colorimetric fluorescent probe based on naphthalenone scaffold for selective detection of hypochlorite and its application in living cells[J]. Sensors and Actuators B: Chemical, 2018, 269: 322-330.
62	TANG Yong, LI Yuanyuan, HAN Juan, et al. A coumarin based fluorescent probe for rapidly distinguishing of hypochlorite and copper(II) ion in organisms[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 208: 299-308.
63	WANG Yun, XIA Jinchen, HAN Juan, et al. A fast-responsive fluorescent probe based on BODIPY dye for sensitive detection of hypochlorite and its application in real water samples[J]. Talanta, 2016, 161: 847-853.
64	ZHAO Xiongjie, JIANG Yuren, CHEN Yixuan, et al. A new "off-on" NIR fluorescence probe for determination and bio-imaging of mitochondrial hypochlorite in living cells and zebrafish[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 219: 509-516.
65	LI Yuanyuan, TANG Yong, GAO Mengmeng, et al. A sensitive BODIPY-based fluorescent probe suitable for hypochlorite detection in living cells[J]. Journal of Photochemistry and Photobiology A: Chemistry, 2018, 352: 65-72.
66	TANG Xu, ZHU Zhi, WANG Yun, et al. A cyanobiphenyl based fluorescent probe for rapid and specific detection of hypochlorite and its bio-imaging applications[J]. Sensors and Actuators B: Chemical, 2018, 262: 57-63.
67	ZHAO Yun, LI Haoyang, XUE Yuanyuan, et al. A phenanthroimidazole-based fluorescent probe for hypochlorous acid with high selectivity and its bio-imaging in living cells[J]. Sensors and Actuators B: Chemical, 2017, 241: 335-341.
68	TANG Xu, ZHU Zhi, LIU Renjie, et al. A novel ratiometric and colorimetric fluorescent probe for hypochlorite based on cyanobiphenyl and its applications[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 219: 576-581.
69	LI Mengru, DU Fangkai, XUE Pei, et al. An AIE fluorescent probe with a naphthalimide derivative and its application for detection of hypochlorite and imaging inside living cells[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, 227: 117760.
70	GAO Yunling, PAN Yong, HE Yuanyuan, et al. A fast-response, red emission aza-BODIPY-hydrazone-based chemodosimeter for selective detection of HClO[J]. Sensors and Actuators B: Chemical, 2018, 269: 151-157.
71	HE Xiaojun, CHEN Hong., XU Chuchu, et al. Ratiometric and colorimetric fluorescent probe for hypochlorite monitor and application for bioimaging in living cells, bacteria and zebrafish[J]. Journal of Hazardous Materials, 2020, 388: 122029.
72	TANG Xu, ZHU Zhi, WANG Zengkai, et al. Developed a novel quinazolinone based turn-on fluorescence probe for highly selective monitoring hypochlorite and its bioimaging applications[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, 228: 117845.
73	Min Jeoung CHO, Hyein RYU, LEE Hyo Jin, et al. Selective fluorescence signaling of hypochlorite in tap water by oxidative hydrolysis of sulfonhydrazone[J]. Sensors and Actuators B: Chemical, 2017, 241: 285-291.
74	LIU Jinsheng, SHANGGUAN Mingqin., ZENG Xiaoyang, et al. Phosphorescent iridium(III) complex for efficient sensing of hypochlorite and imaging in living cells[J]. Analytical Biochemistry, 2020, 592: 113573.
75	LI Xiaohong, CHEN Weilin, LI Yangguang, et al. Multi-functional rare earth-containing polyoxometalates achieving high-efficiency tumor therapy and visual fluorescence monitoring[J]. Inorganic Chemistry Communications, 2019, 104: 40-47.
76	LU Zhen, SHANGGUAN Mingqin, JIANG Xingzong, et al. A water-soluble cyclometalated iridium(III) complex with fluorescent sensing capability for hypochlorite[J]. Dyes and Pigments, 2019, 171: 107715.
77	PAN Hong, XU Shuo, NI Yonghong. Rare-earth post-modified Zn-based coordination polymer microspheres: simple room-temperature preparation, fluorescent performances and application for detection of tryptophane[J]. Sensors and Actuators B: Chemical, 2019, 283: 731-739.
78	SCHMUED L, RAYMICK J. Introducing Euro-Glo, a rare earth metal chelate with numerous applications for the fluorescent localization of myelin and amyloid plaques in brain tissue sections[J]. Journal of Neuroscience Methods, 2017, 279: 79-86.
79	YANG Bo, CHEN Hui, ZHENG Zhuo, et al. Application of upconversion rare earth fluorescent nanoparticles in biomedical drug delivery system[J]. Journal of Luminescence, 2020, 223: 117226.
80	ZHANG Xiaoxiong, ZHANG Wenjun, LI Yingjie, et al. Hybrid luminescent materials of graphene oxide and rare-earth complexes with stronger luminescence intensity and better thermal stability[J]. Dyes and Pigments, 2017, 140: 150-156.
81	ZHOU Zhan, LI Xiangqian, TANG Yiping, et al. Oxidative deoximation reaction induced recognition of hypochlorite based on a new fluorescent lanthanide-organic framework[J]. Chemical Engineering Journal, 2018, 351: 364-370.
82	ZHOU Zhan, WU Haixia, LI Feifei, et al. Hypochlorite responsive ratiometric fluorescent switch and logic gates based on lanthanide functionalized polymer nanosphere[J]. Dyes and Pigments, 2020, 174: 108033.
83	YI Sili, LU Zhen, LIN Yandai, et al. A novel mitochondria-targeted phosphorescence probe for hypochlorite ions detection in living cells[J]. Talanta, 2020, 209: 120516.
84	ZHU Baocun, WU Liu, ZHANG Meng, et al. A highly specific and ultrasensitive fluorescent probe for monitoring hypochlorous acid and its applications in live cells[J]. Sensors and Actuators B: Chemical, 2018, 267: 589-596.
85	LIU Jingwei, YIN Zheng. A novel NIR-emissive probe with large Stokes shift for hypochlorite detection and imaging in living cells[J]. Talanta, 2019, 196: 352-356.
86	SHI Lei, YANG Sheng, HONG Haojia, et al. A novel target and pH dual-activatable fluorescent probe for precisely detecting hypochlorite in lysosomes[J]. Analytica Chimica Acta, 2020, 1094: 122-129.
87	LIU Caiyun, JIA Pan, ZHUANG Zihan, et al. A water-soluble and highly specific fluorescent probe with large Stokes shift for imaging basal HOCl in living cells and zebrafish[J]. Sensors and Actuators B: Chemical, 2019, 291: 243-249.
88	LIU Caiyun, JIA Pan, WU Liu, et al. Rational design of a highly efficient two-photon fluorescent probe for tracking intracellular basal hypochlorous acid and its applications in identifying tumor cells and tissues[J]. Sensors and Actuators B: Chemical, 2019, 297: 126731.
89	DU Yuchao, WANG Bowei, JIN Di, et al. Dual-site fluorescent probe for multi-response detection of ClO^- and H₂O₂and bio-imaging[J]. Analytica Chimica Acta, 2020, 1103: 174-182.
90	WANG Qing, LIU Chang, CHANG Jiajia, et al. Novel water soluble styrylquinolinium boronic acid as a ratiometric reagent for the rapid detection of hypochlorite ion[J]. Dyes and Pigments, 2013, 99(3): 733-739.
91	GAO Zheng, ZHANG Xu, ZHENG Meiling, et al. Synthesis of a water soluble red fluorescent dye and its application to living cells imaging[J]. Dyes and Pigments, 2015, 120: 37-43.
92	LAN Jinshuai, GUO Jing, JIANG Xiaoyi, et al. A new dicyanoisophorone-based ratiometric and colorimetric near-infrared fluorescent probe for specifically detecting hypochlorite and its bioimaging on a model of acute inflammation[J]. Analytica Chimica Acta, 2020, 1094: 70-79.
93	SHU Wei, YAN Liangguo, WANG Zuokai, et al. A novel visual and far-red fluorescent dual-channel probe for the rapid and sensitive detection of hypochlorite in aqueous solution and living cells[J]. Sensors and Actuators B: Chemical, 2015, 221: 1130-1136.

荧光探针编号	量子产率	响应速度/s	检测限/nmol·L^-1	应用	颜色的变化	参考文献
1	—	215	31.6	L929细胞	无	［35］
2	0.85→0.014	30	41.8	RAW264.7细胞	无	［36］
3	0.233→0.392	40	321	RAW264.7细胞	无	［37］
4	—	120	182	HeLa细胞	红色变无色	［38］
5	—	210	13.2	HeLa细胞	红色变无色	［39］
6	—	13	25	RAW264.7细胞	无	［40］
7	—	—	80	水体样本	蓝色变粉红色	［41］
8	—	—	—	HepG2细胞	无	［42］
9	0.28→0.05	30	165	HeLa细胞	黄色变无色	［43］
10	0.003→0.216	120	4.1	RAW264.7细胞	蓝色变紫色	［44］
11	0.01→0.28	10	22.6	HepG2细胞	蓝色变紫色	［45］
12	0.051→0.074	10	449.76	PC12细胞	淡黄色变无色	［46］
13	0.0013→0.22	60	53	HeLa细胞	无	［47］
14	—	—	39	水体样本	粉红变浅黄色	［48］
15	0.02→0.32	60	120	RAW264.7细胞	无	［52］
16	0.0012→0.0094	—	2330	RAW264.7细胞	无	［53］
17	0.02→0.43	300	737	水体样本	紫色变绿色	［54］
18	—	120	210	A549细胞	黄色变无色	［55］
19	0.07→0.55	20	8.3	RAW264.7细胞	无	［56］
20	—	60	580	CHO细胞	无	［57］
21	—	60	790	CHO细胞	无	［57］
22	0.006→0.389	3s	2.88	RAW264.7细胞	无	［58］
23	0.059→0.56	210	228	HepG2细胞	粉红色变橙色	［65］
24	0.0094→0.1647	30	49	RAMOS细胞	无	［66］
25	—	210	14	HeLa细胞	无	［67］
26	0.166→0.186	30	334	RAMOS细胞	无	［68］
27	—	90	32	HeLa细胞	无	［69］
28	0.0045→0.073	3	270	RAW264.7细胞	无	［70］
29	—	40	128	MRC-5细胞和斑马鱼细胞	黄色变无色	［71］
30	—	20	11.4	RAMOS细胞	无色变黄色	［72］
31	—	300	20	水体样本	无	［73］
32	0.05→0.19	15	86	HeLa细胞	无	［74］
33	—	20	20.5	4T1细胞	无	［83］
34	—	300	164	RAW264.7细胞	无	［85］
35	0.001→0.22	5	24.3	HeLa细胞	无	［86］
36	0.028→0.371	5	3.30	RAW264.7细胞	无	［87］
37	—	60	0.9	RAW264.7细胞	无	［88］
38	—	180	28.2	HeLa细胞	无	［89］
39	—	120	63	试纸条应用	浅绿色变橙色	［90］
40	0.019→0.066	30	15.7	HepG2细胞	黄色变红色	［92］
41	—	60	400	RAW264.7细胞	浅黄色变红色	［93］

荧光探针编号	量子产率	响应速度/s	检测限/nmol·L^-1	应用	颜色的变化	参考文献
1	—	215	31.6	L929细胞	无	［35］
2	0.85→0.014	30	41.8	RAW264.7细胞	无	［36］
3	0.233→0.392	40	321	RAW264.7细胞	无	［37］
4	—	120	182	HeLa细胞	红色变无色	［38］
5	—	210	13.2	HeLa细胞	红色变无色	［39］
6	—	13	25	RAW264.7细胞	无	［40］
7	—	—	80	水体样本	蓝色变粉红色	［41］
8	—	—	—	HepG2细胞	无	［42］
9	0.28→0.05	30	165	HeLa细胞	黄色变无色	［43］
10	0.003→0.216	120	4.1	RAW264.7细胞	蓝色变紫色	［44］
11	0.01→0.28	10	22.6	HepG2细胞	蓝色变紫色	［45］
12	0.051→0.074	10	449.76	PC12细胞	淡黄色变无色	［46］
13	0.0013→0.22	60	53	HeLa细胞	无	［47］
14	—	—	39	水体样本	粉红变浅黄色	［48］
15	0.02→0.32	60	120	RAW264.7细胞	无	［52］
16	0.0012→0.0094	—	2330	RAW264.7细胞	无	［53］
17	0.02→0.43	300	737	水体样本	紫色变绿色	［54］
18	—	120	210	A549细胞	黄色变无色	［55］
19	0.07→0.55	20	8.3	RAW264.7细胞	无	［56］
20	—	60	580	CHO细胞	无	［57］
21	—	60	790	CHO细胞	无	［57］
22	0.006→0.389	3s	2.88	RAW264.7细胞	无	［58］
23	0.059→0.56	210	228	HepG2细胞	粉红色变橙色	［65］
24	0.0094→0.1647	30	49	RAMOS细胞	无	［66］
25	—	210	14	HeLa细胞	无	［67］
26	0.166→0.186	30	334	RAMOS细胞	无	［68］
27	—	90	32	HeLa细胞	无	［69］
28	0.0045→0.073	3	270	RAW264.7细胞	无	［70］
29	—	40	128	MRC-5细胞和斑马鱼细胞	黄色变无色	［71］
30	—	20	11.4	RAMOS细胞	无色变黄色	［72］
31	—	300	20	水体样本	无	［73］
32	0.05→0.19	15	86	HeLa细胞	无	［74］
33	—	20	20.5	4T1细胞	无	［83］
34	—	300	164	RAW264.7细胞	无	［85］
35	0.001→0.22	5	24.3	HeLa细胞	无	［86］
36	0.028→0.371	5	3.30	RAW264.7细胞	无	［87］
37	—	60	0.9	RAW264.7细胞	无	［88］
38	—	180	28.2	HeLa细胞	无	［89］
39	—	120	63	试纸条应用	浅绿色变橙色	［90］
40	0.019→0.066	30	15.7	HepG2细胞	黄色变红色	［92］
41	—	60	400	RAW264.7细胞	浅黄色变红色	［93］

[1]	雷伟, 姜维佳, 王玉高, 和明豪, 申峻. N、S共掺杂煤基碳量子点的电化学氧化法制备及用于Fe³⁺检测[J]. 化工进展, 2023, 42(9): 4799-4807.
[2]	毛善俊, 王哲, 王勇. 基团辨识加氢：从概念到应用[J]. 化工进展, 2023, 42(8): 3917-3922.
[3]	孙旭东, 赵玉莹, 李诗睿, 王琦, 李晓健, 张博. 我国地方性氢能发展政策的文本量化分析[J]. 化工进展, 2023, 42(7): 3478-3488.
[4]	张芳, 郭鹍鹏, 梁春平, 尤雪瑞, 张志超. 一种具有聚集诱导发光效应有机荧光小分子的设计合成及功能应用[J]. 化工进展, 2023, 42(6): 3097-3104.
[5]	徐国彬, 刘洪豪, 李洁, 郭家奇, 王琪. ZnO量子点水性喷墨荧光墨水制备及性能[J]. 化工进展, 2023, 42(6): 3114-3122.
[6]	秦凯, 杨仕林, 李俊, 储震宇, 薄翠梅. 基于卡尔曼滤波算法的葡萄糖酶生物传感器高精度检测方法[J]. 化工进展, 2023, 42(6): 3177-3186.
[7]	金涌, 程易, 白丁荣, 张晨曦, 魏飞. 中国流态化技术研发史略[J]. 化工进展, 2023, 42(6): 2761-2780.
[8]	李建雄, 耿爽, 胡树坚, 周明. 脂质体递送系统功能结构设计与应用研究进展[J]. 化工进展, 2023, 42(4): 2003-2012.
[9]	司银芳, 胡语婕, 张凡, 董浩, 佘跃惠. 生物合成氧化锌纳米颗粒材料及其抗菌应用[J]. 化工进展, 2023, 42(4): 2013-2023.
[10]	吴恒, 李银龙, 晏刚, 熊通, 张浩, 陶骙. 蒸气压缩制冷/热泵系统中的气液分离技术[J]. 化工进展, 2023, 42(3): 1129-1142.
[11]	陈邦富, 欧阳平, 李宇涵, 段有雨, 董帆. ZnSn(OH)₆ 基纳米材料在环境光催化中的应用[J]. 化工进展, 2023, 42(2): 756-764.
[12]	潘月磊, 程旭东, 闫明远, 何盼, 张和平. 二氧化硅气凝胶及其在保温隔热领域应用进展[J]. 化工进展, 2023, 42(1): 297-309.
[13]	罗爱芹, 蔡艳慧, 梁阿新, 解炳腾. 新型分子印迹生物传感器在癌症生物标志物中的应用[J]. 化工进展, 2022, 41(S1): 448-460.
[14]	付春龙, 王松江, 李国智. 煤气化细渣燃烧技术研究进展[J]. 化工进展, 2022, 41(S1): 516-523.
[15]	黄岳峰, 马丽莎, 张莉莉, 王志国. 木质纤维素复合生物质薄膜材料的功能化应用研究进展[J]. 化工进展, 2022, 41(9): 4840-4854.