Citation: Jing-Jing ZHANG, Ming YAN, Wen LU, Li XU, Xiao-Qing WANG. Design, Synthesis and Fluorescence Imaging Application of Hypochlorite Probe Based on Coumarin-oxime[J]. Chinese Journal of Inorganic Chemistry, ;2021, 37(6): 1071-1079. doi: 10.11862/CJIC.2021.133 shu

Design, Synthesis and Fluorescence Imaging Application of Hypochlorite Probe Based on Coumarin-oxime

College of Science, Nanjing Forestry University, Nanjing 210093, China

Corresponding author: Li XU, xuliqby@njfu.edu.cn Xiao-Qing WANG, xqwang@njfu.edu.cn
Received Date: 22 January 2021
Revised Date: 27 April 2021

Figures(8)

We designed and synthesized a fluorescent probe for hypochlorite based on coumarin-oxime (Cou-HC). Not only Cou-HC showed a rapid and highly selective response to hypochlorite, but also the product after the probe oxidation did not react with biological thiols, which could avoid the interference of biological thiols on the response of hypochlorite. The results of cell imaging experiments showed that the probe could perform real-time imaging of endogenous and exogenous hypochlorite in RAW 264.7 cells, which proves the probe's ability to detect hypochlorite in living systems.
- fluorescent probe,
- hypochlorite,
- coumarin,
- fluorescence detection,
- cell imaging
1. [1]
  D'Autreaux B, Toledano M B. Nat. Rev. Mol. Cell Biol. , 2007, 8(10): 813-824 doi: 10.1038/nrm2256
2. [2]
  Hawkins C L, Davies M J. Chem. Res. Toxicol. , 2005, 18: 1600-1610 doi: 10.1021/tx050207b
3. [3]
  Winterbourn C C. Nat. Chem. Biol. , 2008, 4(5): 278-286 doi: 10.1038/nchembio.85
4. [4]
  Christine J D, Michael W W, Winterbourn C C, Kettle A J. Biochem. J. , 1997, 327: 487-492 doi: 10.1042/bj3270487
5. [5]
  Fu S, Davies M J, Stocker R, Dean R T. Biochem. J. , 1998, 333: 519-525 doi: 10.1042/bj3330519
6. [6]
  Squadrito G L, Postlethwait E M, Matalon S. Am. J. Physiol. Lung C, 2010, 299(3): 289-300 doi: 10.1152/ajplung.00077.2010
7. [7]
  Anatoliotakis N, Deftereos S, Bouras G, Giannopoulos G, Tsounis D, Angelidis C, Kaoukis A, Stefanadis C. Curr. Top. Med. Chem. , 2013, 13: 115-138 doi: 10.2174/1568026611313020004
8. [8]
  Yap Y W, Whiteman M, Bay B H, Li Y, Sheu F S, Qi R Z, Tan C H, Cheung N S. J. Neurochem. , 2006, 98(5): 1597-1609 doi: 10.1111/j.1471-4159.2006.03996.x
9. [9]
  Li H F, Miao Y, Liu Z X, Wu X, Piao C X, Zhou X. Dyes Pigm. , 2020, 176: 108192 doi: 10.1016/j.dyepig.2020.108192
10. [10]
  Meng H, Huang X Q, Lin Y, Yang D Y, Lv Y J, Cao X Q, Zhang G X, Dong J, Shen S L. Spectrochim. Acta Part A, 2019, 223: 117355 doi: 10.1016/j.saa.2019.117355
11. [11]
  Grundler P, Holzapfel H. Talanta, 1971, 18: 147-153 doi: 10.1016/0039-9140(71)80023-1
12. [12]
  Zhou Y, Pei W B, Wang C Y, Zhu J X, Wu J S, Yan Q Y, Huang L, Huang W, Yao C, Loo J S C, Zhang Q C. Small, 2014, 10(17): 3560-3567 doi: 10.1002/smll.201303127
13. [13]
  Zhao C C, An J C, Zhou L, Fei Q, Wang F Y, Tan J, Shi B, Wang R, Guo Z Q, Zhu W H. Chem. Commun. , 2016, 52(10): 2075-2078 doi: 10.1039/C5CC08936K
14. [14]
  Xiao H D, Xin K, Dou H F, Yin G, Quan Y W, Wang R Y. Chem. Commun. , 2015, 51(8): 1442-1445 doi: 10.1039/C4CC07411D
15. [15]
  Parvez S, Long M J C, Poganik J R, Aye Y. Chem. Rev. , 2018, 118(18): 8798-8888 doi: 10.1021/acs.chemrev.7b00698
16. [16]
  Chen X Q, Wang F, Hyun J Y, Wei T W, Qiang J, Ren X T, Shin I, Yoon J. Chem. Soc. Rev. , 2016, 45(10): 2976-3016 doi: 10.1039/C6CS00192K
17. [17]
  Li X H, Gao X H, Shi W, Ma H M. Chem. Rev. , 2014, 114(1): 590-659 doi: 10.1021/cr300508p
18. [18]
  Sun Q, Xu J J, Ji C L, Shaibani M S S, Li Z, Lim K, Zhang C W, Li L, Liu Z P. Anal. Chem. , 2020, 92(5): 4038-4045 doi: 10.1021/acs.analchem.9b05599
19. [19]
  Hu J J, Wong N K, Gu Q S, Bai X Y, Ye S, Yang D. Org. Lett. , 2014, 16(13): 3544-3547 doi: 10.1021/ol501496n
20. [20]
  Lin W Y, Long L L, Chen B B, Tan W. Chem. Eur. J. , 2009, 15(10): 2305-2309 doi: 10.1002/chem.200802054
21. [21]
  Lou Z R, Li P, Song P, Han K L. Analyst, 2013, 138(21): 6291-6295 doi: 10.1039/c3an00198a
22. [22]
  Shi J, Li Q Q, Zhang X, Peng M, Qin J G, Li Z. Sens. Actuators B, 2010, 145(1): 583-587 doi: 10.1016/j.snb.2009.11.003
23. [23]
  Koide Y, Urano Y, Kenmoku S, Kojima H, Nagano T. J. Am. Chem. Soc. , 2007, 129(34): 10324-10325 doi: 10.1021/ja073220m
24. [24]
  Zhao N, Wu Y H, Wang R M, Shi L X, Chen Z N. Analyst, 2011, 136(11): 2277-2282 doi: 10.1039/c1an15030h
25. [25]
  Wu L, Wu I C, DuFort C C, Carlson M A, Wu X, Chen L, Kuo C T Qin Y L, Yu J B, Hingorani S R, Chiu D T. J. Am. Chem. Soc. , 2017, 139(20): 6911-6918 doi: 10.1021/jacs.7b01545
26. [26]
  Zhang X F, Zhao W Y, Li B, Li W Q, Zhang C X, Hou X C, Jiang J, Dong Y Z. Chem. Sci. , 2018, 9(43): 8207-8212 doi: 10.1039/C8SC03226B
27. [27]
  Wu G S, Thirumalaivasan N, Lin T C, Wu S P. J. Pharm. Biomed. Anal. , 2020, 190: 113545 doi: 10.1016/j.jpba.2020.113545
28. [28]
  He X J, Chen H, Xu C C, Fan J Y, Xu W, Li Y H, Deng H, Shen J L. J. Hazard. Mater. , 2020, 388: 122029 doi: 10.1016/j.jhazmat.2020.122029
29. [29]
  Liu L Y, Jiang L P, Yuan W, Liu Z K, Liu D Y, Wei P, Zhang X Y, Yi T. ACS Sens. , 2020, 5(8): 2457-2466 doi: 10.1021/acssensors.0c00640
30. [30]
  Yang J J, Zheng W B, Shen Y, Xu Y Z, Lv G L, Li C X. J. Lumin. , 2020, 226: 117460 doi: 10.1016/j.jlumin.2020.117460
31. [31]
  Liu D D, Feng S M, Feng G Q. Sens. Actuators B, 2018, 269: 15-21 doi: 10.1016/j.snb.2018.04.152
32. [32]
  Sun Z N, Liu F Q, Chen Y, Tam P K H, Yang D. Org. Lett. , 2008, 10(11): 2171-2174 doi: 10.1021/ol800507m
33. [33]
  Wu Y L, Wang J, Zeng F, Huang S L, Huang J, Xie H T, Yu C M, Wu S Z. ACS Appl. Mater. Interfaces, 2016, 8(2): 1511-1519 doi: 10.1021/acsami.5b11023
34. [34]
  Li H Y, Li X H, Wu X F, Shi W, Ma H M. Anal. Chem. , 2017, 89(10): 5519-5525 doi: 10.1021/acs.analchem.7b00503
35. [35]
  Zhu B C, Zhang M, Wu L, Zhao Z Y, Liu C Y, Wang Z K, Duan Q X, Wang Y W, Jia P. Sens. Actuators B, 2018, 257: 436-441 doi: 10.1016/j.snb.2017.10.170
36. [36]
  Khurana J M, Ray A, Sahoo P K. Bull. Chem. Soc. Jpn. , 1994, 67(4): 1091-1093 doi: 10.1246/bcsj.67.1091
37. [37]
  Dong S Q, Zhang L J, Lin Y J, Ding C F, Lu C. Analyst, 2020, 145(15): 5068-5089 doi: 10.1039/D0AN00645A
38. [38]
  Lin W Y, Long L L, Chen B B, Tan W. Chem. Eur. J. , 2009, 15: 2305-2309 doi: 10.1002/chem.200802054
39. [39]
  Shi Y, Huo F J, Yin C X. Sens. Actuators B, 2020, 325: 128793 doi: 10.1016/j.snb.2020.128793
40. [40]
  Yang X F, Shi W D, Dong X L, Cui C Y, Huang X, Wang X, Xie H X, Li Y X, Yan M, Cui Y, Sun G X. Polyhedron, 2020, 185: 114563 doi: 10.1016/j.poly.2020.114563
41. [41]
  Wang B S, Li P, Yu F B, Song P, Sun X F, Yang S Q, Lou Z R, Han K L. Chem. Commun. , 2013, 49(10): 1014-1016 doi: 10.1039/C2CC37803E
42. [42]
  Liu S R, Wu S P. Org. Lett. , 2013, 15(4): 878-881 doi: 10.1021/ol400011u
43. [43]
  Cao D X, Liu Z P, Verwilst P, Koo S, Jangjili P, Kim J S, Lin W Y. Chem. Rev. , 2019, 119(18): 10403-10519 doi: 10.1021/acs.chemrev.9b00145
44. [44]
  Watanabe S, Alexander M, Misharin A V, Budinger G R S. J. Clin. Invest. , 2019, 129(7): 2619-2628 doi: 10.1172/JCI124615
1. [1]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
2. [2]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
3. [3]
  Qin Hou , Jiayi Hou , Aiju Shi , Xingliang Xu , Yuanhong Zhang , Yijing Li , Juying Hou , Yanfang Wang . Preparation of Cuprous Iodide Coordination Polymer and Fluorescent Detection of Nitrite: A Comprehensive Chemical Design Experiment. University Chemistry, 2024, 39(8): 221-229. doi: 10.3866/PKU.DXHX202312056
4. [4]
  Chun-Lin Sun , Yaole Jiang , Yu Chen , Rongjing Guo , Yongwen Shen , Xinping Hui , Baoxin Zhang , Xiaobo Pan . Construction, Performance Testing, and Practical Applications of a Home-Made Open Fluorescence Spectrometer. University Chemistry, 2024, 39(5): 287-295. doi: 10.3866/PKU.DXHX202311096
5. [5]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
6. [6]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
7. [7]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
8. [8]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
9. [9]
  Xinyu Liu , Weiran Hu , Zhengkai Li , Wei Ji , Xiao Ni . Algin Lab: Surging Luminescent Sea. University Chemistry, 2024, 39(5): 396-404. doi: 10.3866/PKU.DXHX202312021
10. [10]
  Jianjun Liu , Xue Yang , Chi Zhang , Xueyu Zhao , Zhiwei Zhang , Yongmei Chen , Qinghong Xu , Shao Jin . Preparation and Fluorescence Characterization of CdTe Semiconductor Quantum Dots. University Chemistry, 2024, 39(7): 307-315. doi: 10.3866/PKU.DXHX202311031
11. [11]
  Zishuo Yi , Peng Liu , Yan Xu . Fluorescent “Chameleon”: A Popular Science Experiment Based on Dynamic Luminescence. University Chemistry, 2024, 39(9): 304-310. doi: 10.12461/PKU.DXHX202311079
12. [12]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
13. [13]
  Xinyi Hong , Tailing Xue , Zhou Xu , Enrong Xie , Mingkai Wu , Qingqing Wang , Lina Wu . Non-Site-Specific Fluorescent Labeling of Proteins as a Chemical Biology Experiment. University Chemistry, 2024, 39(4): 351-360. doi: 10.3866/PKU.DXHX202310010
14. [14]
  Lin Song , Dourong Wang , Biao Zhang . Innovative Experimental Design and Research on Preparing Flexible Perovskite Fluorescent Gels Using 3D Printing. University Chemistry, 2024, 39(7): 337-344. doi: 10.3866/PKU.DXHX202310107
15. [15]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
16. [16]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
17. [17]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
18. [18]
  Liwei Wang , Guangran Ma , Li Wang , Fugang Xu . A Comprehensive Analytical Chemistry Experiment: Colorimetric Detection of Vitamin C Using Nanozyme and Smartphone. University Chemistry, 2024, 39(8): 255-262. doi: 10.3866/PKU.DXHX202312094
19. [19]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
20. [20]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079

Get Citation

PDF

XML

Metrics

PDF Downloads(17)
Abstract views(873)
HTML views(182)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142