Research on Chemical Intermediates

, Volume 44, Issue 9, pp 5169–5180 | Cite as

A novel BF2–curcumin-based fluorescent chemosensor for detection of Cu2+ in aqueous solution and living cells

  • Yuan Li
  • Yu-Xin Ji
  • Lin-Jiang Song
  • Yi Zhang
  • Zi-Cheng Li
  • Li Yang
  • Wen-Cai HuangEmail author


A novel BF2–curcumin-based chemosensor 1, namely monopicolinate of BF2–curcumin complex, was designed, synthesized and applied for the detection of Cu2+ in aqueous buffer solution and living cells. Sensor 1 exhibited sensitive naked-eye color change toward Cu2+ from blue to pink in TBS solution and the detection limit was estimated to be 0.12 µM. The selectivity of sensor 1 for Cu2+ was high over competing metal ions (Ag+, Cu+, Hg2+, Mg2+, Ca2+, Co2+, Zn2+, Mn2+, Ni2+, Fe2+ and Fe3+). Based on the experimental results, the sensing mechanism was proposed for the Cu2+ triggered hydrolysis of 1 to BF2–curcumin which has unique chromogenic and fluorogenic properties. Compared with other chemosensors with a similar mechanism, chemosensor 1 had a comparatively large Stokes shift and the emission wavelength was close to NIR. Moreover, cell imaging investigations indicated that sensor 1 has the potential to be applied for practical Cu2+ detection in biological systems.


Cu2+ detection Chemosensor Curcumin Naked eye Picolinate 



We thank the Analytical and Testing Center of Sichuan University for NMR measurements.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11164_2018_3416_MOESM1_ESM.docx (490 kb)
Supplementary material 1 (DOCX 489 kb)


  1. 1.
    M.C. Linder, M. Hazegh-Azam, Am. J. Clin. Nutr. 63, 797S (1996)PubMedGoogle Scholar
  2. 2.
    R. Uauy, M. Olivares, M. Gonzalez, Am. J. Clin. Nutr. 67, 952S (1998)CrossRefPubMedGoogle Scholar
  3. 3.
    R.A. Festa, D.J. Thiele, Curr. Biol. 21, R877 (2011)CrossRefPubMedPubMedCentralGoogle Scholar
  4. 4.
    D. Radisky, J. Kaplan, J. Biol. Chem. 274, 4481 (1999)CrossRefPubMedGoogle Scholar
  5. 5.
    N.J. Robinson, D.R. Winge, Annu. Rev. Biochem. 79, 537 (2010)CrossRefPubMedPubMedCentralGoogle Scholar
  6. 6.
    J.L. Burkhead, K.A. Reynolds, S.E. Abdel-Ghany, C.M. Cohu, M. Pilon, New Phytol. 182, 799 (2009)CrossRefPubMedGoogle Scholar
  7. 7.
    S. Lutsenko, Curr. Opin. Chem. Biol. 14, 211 (2010)CrossRefPubMedGoogle Scholar
  8. 8.
    D.C. Brady, M.S. Crowe, M.L. Turski, G.A. Hobbs, X. Yao, A. Chaikuad, S. Knapp, K. Xiao, S.L. Campbell, D.J. Thiele, C.M. Counter, Nature 509, 492 (2014)CrossRefPubMedPubMedCentralGoogle Scholar
  9. 9.
    Y.H. Hung, A.I. Bush, R.A. Cherny, J. Biol. Inorg. Chem. 15, 61 (2010)CrossRefPubMedGoogle Scholar
  10. 10.
    G. Eskici, P.H. Axelsen, Biochemistry 51, 6289 (2012)CrossRefPubMedGoogle Scholar
  11. 11.
    K.M. Davies, J.F.B. Mercer, N. Chen, K.L. Double, Clin. Sci. 130, 565 (2016)CrossRefPubMedGoogle Scholar
  12. 12.
    P.C. Bull, G.R. Thomas, J.M. Rommens, J.R. Forbes, D.W. Cox, Nat. Genet. 5, 327 (1993)CrossRefPubMedGoogle Scholar
  13. 13.
    E. Gaggelli, H. Kozlowski, D. Valensin, G. Valensin, Chem. Rev. 106, 1995 (2006)CrossRefPubMedGoogle Scholar
  14. 14.
    A. Gonzales, M. Firmino, C. Nomura, F. Rocha, P. Oliveira, I. Gaubeur, Anal. Chim. Acta 636, 198 (2009)CrossRefPubMedGoogle Scholar
  15. 15.
    M.V. Zoriy, D. Mayer, J.S. Becker, J. Am. Soc. Mass Spectrom. 20, 883 (2009)CrossRefPubMedGoogle Scholar
  16. 16.
    Y. Liu, P. Liang, L. Guo, Talanta 68, 25 (2005)CrossRefPubMedGoogle Scholar
  17. 17.
    J. Zhuang, L. Zhang, W. Lu, D. Shen, R. Zhu, D. Pan, Int. J. Electrochem. Sci. 6, 4690 (2011)Google Scholar
  18. 18.
    E.L. Que, D.W. Domaille, C.J. Chang, Chem. Rev. 108, 1517 (2008)CrossRefPubMedGoogle Scholar
  19. 19.
    J.A. Cotruvo Jr., A.T. Aron, K.M. Ramos-Torres, C.J. Chang, Chem. Soc. Rev. 44, 4400 (2015)CrossRefPubMedPubMedCentralGoogle Scholar
  20. 20.
    G.T. Sfrazzetto, C. Satriano, G.A. Tomaselli, E. Rizzarelli, Coord. Chem. Rev. 311, 125 (2016)CrossRefGoogle Scholar
  21. 21.
    A.T. Aron, K.M. Ramos-Torres, J.A. Cotruvo Jr., C.J. Chang, Acc. Chem. Res. 48, 2434 (2015)CrossRefPubMedPubMedCentralGoogle Scholar
  22. 22.
    Z. Yang, Y. Zhao, S. Chen, Y. Bu, X. Zhu, Y. Du, F. Li, Sens. Actuators B Chem. 235, 414 (2016)CrossRefGoogle Scholar
  23. 23.
    X.T. Chen, A.J. Tong, Dyes Pigments 95, 776 (2012)CrossRefGoogle Scholar
  24. 24.
    Q.Q. Li, M. Peng, N.N. Li, J.G. Qin, Z. Li, Sens. Actuators B Chem. 173, 580 (2012)CrossRefGoogle Scholar
  25. 25.
    C. Zhao, P. Feng, J. Cao, X. Wang, Y. Yang, Y. Zhang, J. Zhang, Y. Zhang, Org. Biomol. Chem. 10, 3104 (2012)CrossRefPubMedGoogle Scholar
  26. 26.
    O. Garcia-Beltran, N. Mena, L.C. Friedrich, J.C. Netto-Ferreira, V. Vargas, F.H. Quina, M.T. Nunez, B.K. Cassels, Tetrahedron Lett. 53, 5280 (2012)CrossRefGoogle Scholar
  27. 27.
    D. Li, X. Sun, J. Huang, Q. Wang, Y. Feng, M. Chen, X. Meng, M. Zhu, X. Wang, Dyes Pigments 125, 185 (2016)CrossRefGoogle Scholar
  28. 28.
    L.K. Kumawat, M. Kumar, P. Bhatt, A. Sharma, M. Asif, V.K. Gupta, Sens. Actuators B Chem. 240, 365 (2017)CrossRefGoogle Scholar
  29. 29.
    P. Kaur, S. Kaur, K. Singh, P.R. Sharma, T. Kaur, Dalton Trans. 40, 10818 (2011)CrossRefPubMedGoogle Scholar
  30. 30.
    J. Bu, H. Duan, X. Wang, Res. Chem. Intermed. 40, 3119 (2014)CrossRefGoogle Scholar
  31. 31.
    S.O. Tümay, E. Okutan, I.F. Sengul, E. Özcan, H. Kandemir, T. Doruk, M. Çetin, B. Çosut, Polyhedron 117, 161 (2016)CrossRefGoogle Scholar
  32. 32.
    S.K. Sahoo, D. Sharma, A. Moirangthem, A. Kuba, R. Thomas, R. Kumar, A. Kuwar, H.-J. Choi, A. Basu, J. Lumin. 172, 297 (2016)CrossRefGoogle Scholar
  33. 33.
    A. Uslu, S.O. Tümay, A. Şenocak, F. Yuksel, E. Özcan, S. Yeşilot, Dalton Trans. 46, 9140 (2017)CrossRefPubMedGoogle Scholar
  34. 34.
    D. Zhu, A. Ren, X. He, Y. Luo, Z. Duan, X. Yan, Y. Xiong, X. Zhong, Sens. Actuators B Chem. 252, 134 (2017)CrossRefGoogle Scholar
  35. 35.
    A. Amalraj, A. Pius, S. Gopi, S. Gopi, J. Tradit. Complement. Med. 7, 205 (2017)CrossRefPubMedGoogle Scholar
  36. 36.
    A. Marchiani, C. Rozzo, A. Fadda, G. Delogu, P. Ruzza, Curr. Med. Chem. 21, 204 (2014)CrossRefPubMedGoogle Scholar
  37. 37.
    K.I. Priyadarsini, J. Photochem. Photobiol., C 10, 81 (2009)CrossRefGoogle Scholar
  38. 38.
    Z. Pi, J. Wang, B. Jiang, G. Cheng, S. Zhou, Mater. Sci. Eng. C Mater. 46, 565 (2015)CrossRefGoogle Scholar
  39. 39.
    G. Xu, J. Wang, G. Si, M. Wang, B. Wu, S. Zhou, Dyes Pigments 123, 267 (2015)CrossRefGoogle Scholar
  40. 40.
    K. Liu, T.L. Guo, J. Chojnacki, H.G. Lee, X. Wang, S.L. Siedlak, W. Rao, X. Zhu, S. Zhang, ACS Chem. Neurosci. 3, 141 (2012)CrossRefPubMedGoogle Scholar
  41. 41.
    K. Park, Y. Seo, M.K. Kim, K. Kim, Y.K. Kim, H. Choo, Y. Chong, Org. Biomol. Chem. 13, 11194 (2015)CrossRefPubMedGoogle Scholar
  42. 42.
    X. Zhang, Y. Tian, H. Zhang, A. Kavishwar, M. Lynes, A.L. Brownell, H. Sun, Y.H. Tseng, A. Moore, C. Ran, Sci. Rep. 5, 13116 (2015)CrossRefPubMedPubMedCentralGoogle Scholar
  43. 43.
    A.D’. Aléo, A. Felouat, F. Fages, Adv. Nat. Sci. Nanosci. Nanotechnol. 6, 015009 (2015)Google Scholar
  44. 44.
    A. Chaicham, S. Kulchat, G. Tumcharern, T. Tuntulani, B. Tomapatanaget, Tetrahedron 66, 6217 (2010)CrossRefGoogle Scholar
  45. 45.
    G. Xu, J. Wang, G. Si, M. Wang, X. Xue, B. Wu, S. Zhou, Sens. Actuators B Chem. 230, 684 (2016)CrossRefGoogle Scholar
  46. 46.
    H.T. Zhang, R.C. Liu, J. Liu, L. Li, P. Wang, S.Q. Yao, Z.T. Xu, H.Y. Sun, Chem. Sci. 7, 256 (2016)CrossRefPubMedGoogle Scholar
  47. 47.
    H. Zhang, L. Feng, Y. Jiang, Y.T. Wong, Y. He, G. Zheng, J. He, Y. Tan, H. Sun, D. Ho, Biosens. Bioelectron. 94, 24 (2017)CrossRefPubMedGoogle Scholar
  48. 48.
    L. Tang, P. He, K. Zhong, S. Hou, Y. Bian, Spectrochim. Acta A 169, 246 (2016)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Pharmaceutical and Bioengineering, School of Chemical EngineeringSichuan UniversityChengduChina
  2. 2.Cancer CenterWest China Hospital, Sichuan University and Collaborative Innovation CenterChengduChina

Personalised recommendations