Citation: Zhang Yingpeng, You Caixia, Yang Yunshang, Liu Xiaoyu, Guo Huichen, Dong Yuying. Synthesis of Reversible Fluorescence Quenched Probe for Cu2+ and Imaging in PK-15 cells[J]. Chinese Journal of Organic Chemistry, ;2016, 36(6): 1401-1406. doi: 10.6023/cjoc201512033 shu

Synthesis of Reversible Fluorescence Quenched Probe for Cu2+ and Imaging in PK-15 cells

  • Corresponding author: Zhang Yingpeng, yingpengzhang@126.com Yang Yunshang, yangyunshang@tom.com
  • Received Date: 23 December 2015
    Revised Date: 15 January 2016

    Fund Project: Project supported by the Natural Science Foundation of Gansu Province No. 2014GS03265

Figures(8)

  • A new pyrazoline derivative 1-(2-hydroxyphenyl)-4-(9-anthryl)-3-benzothiazole pyrazolin (P1) was designed and synthesized. The recognition properties of the target compound P1 with metal ions had been investigated by UV absorption and fluorescence spectrophotometry. The probe exhibits several favorable features, including instantaneous, reversible recognition, high sensitivity and selectivity to copper ions. Cytotoxicity test and fluorescent immunoassay results show that compound P1 has good biocompatibility and low toxicity with its IC50 value of 376.558 μmol/L.
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    1. [1]

      De Silva, A. P.; Gunaratne, H. N.; Gunnlaugsson, T.; Huxley, A. J.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515. 

    2. [2]

    3. [3]

      Andrews, N. C. Curr. Opin. Chem. Biol. 2002, 6, 181. 

    4. [4]

      Waggoner, D. J.; Bartnikas, T. B.; Gitlin, J. D. Neurobiol. Dis. 1999, 6, 221. 

    5. [5]

      Finkel, T.; Serrano, M.; Blasco, M. A. Nature 2007, 448, 767. 

    6. [6]

      Waggoner, D. J.; Bartnikas, T. B.; Gitlin, J. D. Neurobiol. Dis. 1999, 6, 221. 

    7. [7]

      Camakaris, J.; Voskoboinik, I.; Mercer, J. F. Biochem. Biophys. Res. Commun. 1999, 261, 225. 

    8. [8]

      Bruijn, L. I.; Miller, T. M.; Cleveland, D. W. Annu. Rev. Neurosci. 2004, 27, 723. 

    9. [9]

      Hung, Y. H.; Bush, A. I.; Cherny, R. A. J. Biol. Inorg. Chem. 2010, 15, 61. 

    10. [10]

      Brown, D. R.; Kozlowski, H. Dalton Trans. 2004, 13, 1907.

    11. [11]

       

    12. [12]

    13. [13]

       

    14. [14]

      Chen, K.; Guo, Y.; Lu, Z.; Yang, B.; Shi, Z. Chin. J. Chem. 2010, 28, 55.

    15. [15]

      Pan, M.; Lin, X. M.; Li, G. B.; Su, C. Y. Coord. Chem. Rev. 2011, 255, 1921. 

    16. [16]

      Guerchais, V.; Fillaut, J. L. Coord. Chem. Rev. 2011, 255, 2448. 

    17. [17]

      Wen, Z. C.; Yang, R.; He, H.; Jiang, Y. B. Chem. Commun. 2006, 42, 106.

    18. [18]

      Aksuner, N.; Henden, E.; Yilmaz, I.; Cukurovali, A. Dyes Pigm. 2009, 83, 211.

    19. [19]

      Liu, Z.; Zhang, C.; Wang, X.; He, W.; Guo, Z. D. Org Lett. 2012, 14, 4378. 

    20. [20]

      Chen, X.; Tong, A. Dyes Pigm. 2012, 95, 776.

    21. [21]

      Wang, S. Q.; Liu, S. Y.; Wang, H. Y.; Zheng, X. X.; Yuan, X.; Liu, Y. Z.; Zhao, B. X. J. Fluoresc. 2014, 24, 657. 

    22. [22]

      Kim, S. H.; Kim, J. S.; Park, S. M.; Chang, S. K. Org Lett. 2006, 8, 371. 

    23. [23]

      Mu, H.; Gong, R.; Ma, Q.; Sun, Y.; Fu, E. Tetrahedron Lett. 2007, 48, 5525.

    24. [24]

       

    25. [25]

       

    26. [26]

    27. [27]

    28. [28]

    29. [29]

    30. [30]

      Wang, M.; Zhang, J.; Liu, J.; Xu, C.; Ju, H. J. Lumin. 2002, 99, 79. 

    31. [31]

      Li, M. M.; Huang, S. Y.; Ye, H.; Ge, F.; Miao, J. Y.; Zhao, B. X. J. Fluoresc. 2013, 23, 799. 

    32. [32]

      Zhang, Z.; Wang, F. W.; Wang, S. Q.; Ge, F.; Zhao, B. X.; Miao, J. Y. Org. Biomol. Chem. 2012, 10, 8640. 

    33. [33]

      Gong, Z. L.; Ge, F.; Zhao, B. X. Sens. Actuators, B 2011, 159, 148. 

    34. [34]

    35. [35]

    36. [36]

      Shi, H. B.; Ji, S. J.; Bian, B. Dyes Pigm. 2007, 73, 394. 

    37. [37]

      Bian, B.; Ji, S. J.; Shi, H. B. Dyes Pigm. 2008, 76, 348. 

    38. [38]

      Hu, S, L.; Zhang, S, S.; Hu, Y.; Tao, Q.; Wu, A, X. Dyes Pigm. 2013, 96, 509.

    39. [39]

      Zhang, Z.; Wang, F. W.; Wang, S. Q.; Ge, F.; Zhao, B. X. Org. Biomol. Chem. 2012, 10, 8640. 

    40. [40]

      Gong, Z. L.; Ge, F.; Zhao, B. X. Sens. Actuators, B 2011, 159, 148. 

    41. [41]

      Li, M. M.; Zhao, W. B.; Zhang, T. T.; Fan, W. L.; Xu, Y.; Xiao, Y.; Zhao, B. X. J. Fluoresc. 2013, 23, 1263. 

    42. [42]

      Li, M. M.; Huang, S. Y.; Ye, H.; Ge, F.; Miao, J. Y.; Zhao, B. X. J. Fluoresc. 2013, 23, 799. 

    43. [43]

      Wang, S. Q.; Gao, Y.; Wang, H. Y.; Zheng, X. X.; Shen, S. L.; Zhang, Y. R.; Zhao, B. X. Spectrochim. Acta, Part A 2013, 106, 110. 

    44. [44]

      Zhang, T. T.; Wang, F. W.; Li, M. M.; Liu, J. T.; Miao, J. Y.; Zhao, B. X. Sens. Actuators, B 2013, 186, 755. 

    45. [45]

      Wang, S. Q.; Liu, S. Y.; Wang, H. Y.; Zheng, X. X.; Liu, Y. Z.; Zhao, B. X. J. Fluoresc. 2014, 24, 657. 

    46. [46]

      Zhang, T. T.; Chen, X. P.; Liu, J. T.; Zhang, L. Z.; Chu, J. M.; Su, L.; Zhao, B. X. RSC Adv. 2014, 4, 16973. 

    47. [47]

      Li, M. M.; Wang, F. W.; Wang, X. Y.; Zhang, T. T.; Xu, Y.; Xiao, Y.; Zhao, B. X. Anal. Chim. Acta 2014, 826, 77. 

    48. [48]

    49. [49]

    50. [50]

    51. [51]

      Li, J. P.; Lin, Z. P.; Zhang, X. H. Beilstein J. Org. Chem. 2007, 3, 13. 

    52. [52]

    53. [53]

      Sashidhara, K. V.; Avula, S. R.; Doharey, P. K.; Singh, L. R.; Balaramnavar, V. M.; Gupta, J.; Saxena, J. K. Eur. J. Med. Chem. 2015, 103, 418. 

    54. [54]

      Dong, B.; Wang, M.; Xu, C. Luminescence 2013, 28, 628.

    55. [55]

    56. [56]

       

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