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
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