Citation: ZHANG Chang-Li, ZHANG Hong, HE Feng-Yun, YANG Hui, LIU Shao-Xian, LIU Min-Sheng. Coumarin-Based Turn-on Fluorescent Probe for Copper(Ⅱ) Detection and Its Application in Cell Imaging[J]. Chinese Journal of Inorganic Chemistry, ;2019, 35(10): 1869-1876. doi: 10.11862/CJIC.2019.207 shu

Coumarin-Based Turn-on Fluorescent Probe for Copper(Ⅱ) Detection and Its Application in Cell Imaging

Key Laboratory of Advanced Functional Materials of Nanjing, School of Environmental Science, Nanjing Xiaozhuang University, Nanjing 211171, China

Corresponding author: ZHANG Chang-Li, carbon314@163.com
Received Date: 1 June 2019
Revised Date: 19 July 2019

Figures(8)

A new coumarin-based Cu²⁺ probe (Cou-P) according to the Cu²⁺-coordination induced hydrolysis mechanism has been developed. Cou-P exhibits a highly selective turn-on response to Cu²⁺ over other transition metal ions in aqueous media. The recognition mechanism of Cou-P for Cu²⁺ was comfirmed by UV-Vis, fluorescence and mass spectrometry. The results show that Cou-P first forms Cou-P/Cu²⁺(1:1) complex, and Cou-P/Cu²⁺ complex is further catalyzed to 3-(carboxylic acid)-7-(diethylamino)-coumarin (Cou-COOH) by excessive Cu²⁺. Cou-P has low cytotoxicity and good membrane permeability. It has been successfully used to detect Cu²⁺ in MCF-7 cells.
- coumarin,
- copper probe,
- mechanism,
- cell imaging
1. [1]
  Martínez-Máez R, Sancenón F. Chem. Rev., 2003, 103:4419-4476 doi: 10.1021/cr010421e
2. [2]
  Thomas S W, Joly G D, Swager T M. Chem. Rev., 2007, 107:1339-1386 doi: 10.1021/cr0501339
3. [3]
  Kim S K, Lee D H, Hong J I, et al. Acc. Chem. Res., 2009, 42:23-31 doi: 10.1021/ar800003f
4. [4]
  Xu Z C, Chen X Q, Kim H N, et al. Chem. Soc. Rev., 2010, 39:127-137 doi: 10.1039/B907368J
5. [5]
  Zhou Y, Xu Z C, Yoon J. Chem. Soc. Rev., 2011, 40:2222-2235 doi: 10.1039/c0cs00169d
6. [6]
  Vendrell M, Zhai D T, Er J C, et al. Chem. Rev., 2012, 112:4391-4420 doi: 10.1021/cr200355j
7. [7]
  Liu Z P, He W J, Guo Z J. Chem. Soc. Rev., 2013, 42:1568-1600 doi: 10.1039/c2cs35363f
8. [8]
  Prohaska J R, Gybina A A. J. Nutr., 2004, 134:1003-1006 doi: 10.1093/jn/134.5.1003
9. [9]
  Davis A V, O'Halloran T V. Nat. Chem. Biol., 2008, 4:148-151 doi: 10.1038/nchembio0308-148
10. [10]
  Que E L, Domaille D W, Chang C J. Chem. Rev., 2008, 108:1517-1549 doi: 10.1021/cr078203u
11. [11]
  Thiele D J, Gitlin J D. Nat. Chem. Biol., 2008, 4:145-147 doi: 10.1038/nchembio0308-145
12. [12]
  Robinson N J, Winge D R. Annu. Rev. Biochem., 2010, 79:537-562 doi: 10.1146/annurev-biochem-030409-143539
13. [13]
  Cuajungco M P, Lees G J. Neurobiol. Dis., 1997, 4:137-169 doi: 10.1006/nbdi.1997.0163
14. [14]
  Bush A I. Curr. Opin. Chem. Biol., 2000, 4:184-191 doi: 10.1016/S1367-5931(99)00073-3
15. [15]
  Valentine J S, Hart P J. Proc. Natl. Acad. Sci. USA, 2003, 100:3617-3622 doi: 10.1073/pnas.0730423100
16. [16]
  Brown D R, Kozlowski H. Dalton Trans., 2004, 13:1907-1917
17. [17]
  Millhauser G L. Acc. Chem. Res., 2004, 37:79-85 doi: 10.1021/ar0301678
18. [18]
  Frederickson C J, Koh J Y, Bush A I. Nat. Rev. Neurosci., 2005, 6:449-462 doi: 10.1038/nrn1671
19. [19]
  Gaggelli E, Kozlowski H, Valensin D, et al. Chem. Rev., 2006, 106:1995-2044 doi: 10.1021/cr040410w
20. [20]
  Lutsenko S, Gupta A, Burkhead J L, et al. Arch. Biochem. Biophys., 2008, 476:22-32 doi: 10.1016/j.abb.2008.05.005
21. [21]
  Kaler S G. Nat. Rev. Neurol., 2011, 7:15-29 doi: 10.1038/nrneurol.2010.180
22. [22]
  Domaille D W, Que E L, Chang C J. Nat. Chem. Biol., 2008, 4:168-175 doi: 10.1038/nchembio.69
23. [23]
  World Health Oganization. Guidelines for Drinking-Water Quality. 4th Ed. Geneva:World Health Organization, 2017:341
24. [24]
  Wang X B, Ma X Y, Yang Z, et al. Chem. Commun., 2013, 49:11263-11265 doi: 10.1039/c3cc46585c
25. [25]
  Kang D E, Lim C S, Kim J Y, et al. Anal. Chem., 2014, 86:5353-5359 doi: 10.1021/ac500329k
26. [26]
  Sharma N, Reja S I, Bhalla V, et al. Dalton Trans., 2014, 43:15929-15936 doi: 10.1039/C4DT01676A
27. [27]
  Han Y Y, Ding C Q, Zhou J, et al. Anal. Chem., 2015, 87:5333-5339 doi: 10.1021/acs.analchem.5b00628
28. [28]
  Kaur M, Ahn Y H, Choi K, et al. Org. Biomol. Chem., 2015, 13:7149-7153 doi: 10.1039/C5OB00907C
29. [29]
  Li S, Zhang D, Xie X Y, et al. Sens. Actuators B, 2016, 224:661-667 doi: 10.1016/j.snb.2015.10.086
30. [30]
  Jiang H, Li Z J, Kang Y F, et al. Sens. Actuators B, 2017, 242:112-117 doi: 10.1016/j.snb.2016.11.033
31. [31]
  Li Y Y, Sun M T, Zhang K, et al. Sens. Actuators B, 2017, 243:36-42 doi: 10.1016/j.snb.2016.11.118
32. [32]
  Liu L L, Dan F J, Liu W J, et al. Sens. Actuators B, 2017, 247:445-450 doi: 10.1016/j.snb.2017.03.069
33. [33]
  Yoon J W, Chang M J, Hong S, et al. Tetrahedron Lett., 2017, 58:3887-3893 doi: 10.1016/j.tetlet.2017.08.071
34. [34]
  FAN Fang-Lu, JING Jin-Qiu, CHEN Xue-Mei. Chinese J. Inorg. Chem., 2015, 31(3):548-554
35. [35]
  Lin W Y, Yuan L, Tan W, et al. Chem. Eur. J., 2009, 15:1030-1035 doi: 10.1002/chem.200801501
36. [36]
  Li N, Xiang Y, Tong A. Chem. Commun., 2010, 46:3363-3365 doi: 10.1039/c001408g
37. [37]
  Cheng J H, Zhang Y H, Ma X F, et al. Chem. Commun., 2013, 49:11791-11793 doi: 10.1039/c3cc47137c
38. [38]
  Huang L Y, Gu B, Su W, et al. RSC Adv., 2015, 5:76296-76301 doi: 10.1039/C5RA14443D
39. [39]
  Hu X X, Zheng X L, Fan X X, et al. Sens. Actuators B, 2016, 227:191-197 doi: 10.1016/j.snb.2015.12.037
40. [40]
  Li D X, Sun X, Huang J M, et al. Dyes Pigm., 2016, 125:185-191 doi: 10.1016/j.dyepig.2015.10.016
41. [41]
  Sun J, Wang B, Zhao X, et al. Anal. Chem., 2016, 88:1355-1361 doi: 10.1021/acs.analchem.5b03848
42. [42]
  Tan W B, Leng T H, Lai G Q, et al. J. Photochem. Photobiol. A, 2016, 324:81-86 doi: 10.1016/j.jphotochem.2016.03.014
43. [43]
  Tang J, Ma S G, Zhang D, et al. Sens. Actuators B, 2016, 236:109-115 doi: 10.1016/j.snb.2016.05.144
44. [44]
  Wang B G, Cui X Y, Zhang Z Q, et al. Org. Biomol. Chem., 2016, 14:6720-6728 doi: 10.1039/C6OB00894A
45. [45]
  Zhu D J, Luo Y H, Shuai L, et al. Tetrahedron Lett., 2016, 57:5326-5329 doi: 10.1016/j.tetlet.2016.10.056
46. [46]
  Zheng X L, Ji R X, Cao X Q, et al. Anal. Chim. Acta, 2017, 978:48-54 doi: 10.1016/j.aca.2017.04.048
47. [47]
  Gu B, Huang L Y, Xu Z F, et al. Sens. Actuators B, 2018, 273:118-125 doi: 10.1016/j.snb.2018.06.032
48. [48]
  Sirilaksanapong S, Sukwattanasinitt M, Rashatasakhon P. Chem. Commun., 2012, 48:293-295 doi: 10.1039/C1CC16148B
49. [49]
  Zhao C C, Feng P, Cao J, et al. Org. Biomol. Chem., 2012, 10:3104-3109 doi: 10.1039/c2ob06980f
50. [50]
  Yang C Y, Chen Y, Wu K, et al. Anal. Methods, 2015, 7:3327-3330 doi: 10.1039/C5AY00224A
51. [51]
  Tang L J, He P, Zhong K L, et al. Spectrochim. Acta Part A, 2016, 169:246-251 doi: 10.1016/j.saa.2016.06.045
52. [52]
  Zhu D J, Luo Y H, Yan X W, et al. RSC Adv., 2016, 6:87110-87114 doi: 10.1039/C6RA18669F
53. [53]
  Zhang H T, Feng L, Jiang Y, et al. Biosens. Bioelectron., 2017, 94:24-29 doi: 10.1016/j.bios.2017.02.037
1. [1]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
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]
  Xiaotao Jin , Yanlan Wang , Yingping Huang , Di Huang , Xiang Liu . Percarbonate activation catalyzed by nanoblocks of basic copper molybdate for antibiotics degradation: High performance, degradation pathways and mechanism. Chinese Chemical Letters, 2024, 35(10): 109499-. doi: 10.1016/j.cclet.2024.109499
4. [4]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
5. [5]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
6. [6]
  Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
7. [7]
  Jianqiu Li , Yi Zhang , Songen Liu , Jie Niu , Rong Zhang , Yong Chen , Yu Liu . Cucurbit[8]uril-based non-covalent heterodimer realized NIR cell imaging through topological transformation from nanowire to nanorod. Chinese Chemical Letters, 2024, 35(10): 109645-. doi: 10.1016/j.cclet.2024.109645
8. [8]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
9. [9]
  Yuan Dong , Mutian Ma , Zhenyang Jiao , Sheng Han , Likun Xiong , Zhao Deng , Yang Peng . Effect of electrolyte cation-mediated mechanism on electrocatalytic carbon dioxide reduction. Chinese Chemical Letters, 2024, 35(7): 109049-. doi: 10.1016/j.cclet.2023.109049
10. [10]
  Hongxia Li , Xiyang Wang , Du Qiao , Jiahao Li , Weiping Zhu , Honglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747
11. [11]
  Yixin Zhang , Ting Wang , Jixiang Zhang , Pengyu Lu , Neng Shi , Liqiang Zhang , Weiran Zhu , Nongyue He . Formation mechanism for stable system of nanoparticle/protein corona and phospholipid membrane. Chinese Chemical Letters, 2024, 35(4): 108619-. doi: 10.1016/j.cclet.2023.108619
12. [12]
  Jia Fu , Shilong Zhang , Lirong Liang , Chunyu Du , Zhenqiang Ye , Guangming Chen . PEDOT-based thermoelectric composites: Preparation, mechanism and applications. Chinese Chemical Letters, 2024, 35(9): 109804-. doi: 10.1016/j.cclet.2024.109804
13. [13]
  Ping Wang , Tianbao Zhang , Zhenxing Li . Reconstruction mechanism of Cu surface in CO2 reduction process. Chinese Journal of Structural Chemistry, 2024, 43(8): 100328-100328. doi: 10.1016/j.cjsc.2024.100328
14. [14]
  Wenzhong Zhang , Zirui Yan , Lingcheng Chen , Yi Xiao . Sn-fused perylene diimides: Synthesis, mechanism, and properties. Chinese Chemical Letters, 2024, 35(10): 109582-. doi: 10.1016/j.cclet.2024.109582
15. [15]
  Yubang Li , Xixi Hu , Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274
16. [16]
  Lingna Wang , Chenxin Tian , Ruobin Dai , Zhiwei Wang . Eco-friendly regeneration of end-of-life PVDF membrane with triethyl phosphate: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(9): 109356-. doi: 10.1016/j.cclet.2023.109356
17. [17]
  Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H₂O₂ system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
18. [18]
  Fengrui Yang , Debing Wang , Xinying Zhang , Jie Zhang , Zhichao Wu , Qiaoying Wang . Synergistic effects of peroxydisulfate on UV/O₃ process for tetracycline degradation: Mechanism and pathways. Chinese Chemical Letters, 2024, 35(10): 109599-. doi: 10.1016/j.cclet.2024.109599
19. [19]
  Yun-Xin Huang , Lin-Qian Yu , Ke-Yu Chen , Hao Wang , Shou-Yan Zhao , Bao-Cheng Huang , Ren-Cun Jin . Biochar with self-doped N to activate peroxymonosulfate for bisphenol-A degradation via electron transfer mechanism: The active edge graphitic N site. Chinese Chemical Letters, 2024, 35(9): 109437-. doi: 10.1016/j.cclet.2023.109437
20. [20]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(704)
HTML views(152)

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