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

Zhang Yingpeng ^a,*,, ,
You Caixia ^a ,
Yang Yunshang ^a,*,, ,
Liu Xiaoyu ^a ,
Guo Huichen ^b ,
Dong Yuying ^a

a.
School of Petrochemical Engineering, Lanzhou University of Technology, Lanzhou 730050
b.
Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Lanzhou 730050

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 IC₅₀value of 376.558 μmol/L.
- pyrazoline,
- fluorescent probe,
- copper ions,
- recognition,
- PK-15 living cells
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]
1. [1]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
2. [2]
  Xiuhong Liu , Cunxu Yan , Yue Zhang , Xuesong Gao , Haifeng He . 一种新型荧光指示剂应用于配位滴定法中铜含量的测定——分析化学实验教学设计与实践. University Chemistry, 2026, 41(8): 389-401. doi: 10.12461/PKU.DXHX202507135
3. [3]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
4. [4]
  Yunshang YANG , Weiliang ZHAO , Zetai HU , Yingpeng ZHANG . Synthesis and application of a carbazole-pyrazole-based ratiometric fluorescent probe for detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2153-2161. doi: 10.11862/CJIC.20260082
5. [5]
  Liangling Tan , Chonghua Zhang , Xianjun Liu , Yiting Xu , Wanqiang Liu . 科教融合导向的化学综合实验设计——以铜离子特异性荧光探针的研发与应用为例. University Chemistry, 2026, 41(10): 316-325. doi: 10.12461/PKU.DXHX202510041
6. [6]
  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
7. [7]
  Shunping WANG , Chuandong GE , Shuguang QU , Tianduo LI , Shaomin WANG , Qingyuan YANG . Synthesis of a fluorescent probe based on urea-based coordination and Si—O bond cleavage for F^- and Cr(Ⅵ) detection. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 297-308. doi: 10.11862/CJIC.20250214
8. [8]
  Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
9. [9]
  Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370
10. [10]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
11. [11]
  Xiaohong Li , Huanjiang Wang , Fang Tan , Xiaohua Cai , Yingchun Luo , Yanli Leng , Guoyong Zhou , Zhu Wen . Research on the Project-Driven Teaching Model in the Context of New Engineering: A Case Study of the Development of a “Portable Metal ions and Pesticide Residues Intelligent Detection System”. University Chemistry, 2026, 41(1): 204-212. doi: 10.12461/PKU.DXHX202510037
12. [12]
  Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
13. [13]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
14. [14]
  Yubin Su , Chenyu Yao , Shuyan Chen , Lisha Xu , Min Peng , Yawen Wang , Yu Peng , Jianfeng Zheng . 一种聚集诱导发光荧光探针的合成及其在指纹显影中的应用——本科生综合性化学实验探索. University Chemistry, 2026, 41(5): 70-78. doi: 10.12461/PKU.DXHX202511031
15. [15]
  Xinrong Wu , Yingying Ren , Jianxue Wang , Lijin Yang , Jia Jia , Nan Li , Na Zhao . 聚光捕胺——高灵敏胺响应型聚集诱导发光探针的合成及传感应用. University Chemistry, 2026, 41(5): 180-189. doi: 10.12461/PKU.DXHX202509129
16. [16]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
17. [17]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
18. [18]
  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
19. [19]
  Tianrong Zhu , Fan Yu , Yuhang Liu , Haiyi Xu , Tingting Ma , Ming Li , Yuhang Xue , Yazhen Wang , Aihua Li , Biao Xiao , Xiaolun Peng . Intelligent Visualization, Precise Iodometry: Color Recognition-based Indirect Iodometric Method for Copper Determination. University Chemistry, 2026, 41(1): 264-275. doi: 10.12461/PKU.DXHX202503096
20. [20]
  Senqiang Zhu , Ruohan Li , Yujia Yang , Jinzhi Liao , Rui Liu . 聚光成辉——Suzuki偶联反应高效制备聚集诱导发射荧光分子及其潜指纹识别应用. University Chemistry, 2026, 41(5): 109-119. doi: 10.12461/PKU.DXHX202511066

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2054)
HTML views(324)

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

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

Metrics

通讯作者: 陈斌, bchen63@163.com

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