Skip to main content

A novel peptide-based fluorescent probe for highly selective detection of mercury (II) ions in real water samples and living cells based on aggregation-induced emission effect

Analytical and Bioanalytical Chemistry volume 414, pages 4717–4726 (2022)Cite this article

Abstract

A new fluorescent probe TPE-GHK was synthesized containing a tetrastyrene (TPE) derivative as fluorophore and classical tripeptide (Gly-His-Lys-NH2) as a receptor based on the aggregation-induced emission (AIE) mechanism. TPE-GHK displayed high selectivity and rapid fluorescent “turn-on” response to Hg2+ among other competitive metal ions. The 2:1 complex binding mechanism of TPE-GHK toward Hg2+ was verified by fluorometric titration, Job’s plots, and ESI-HRMS spectra. The fluorescent emission showed a good linear response in the range of 0–1.0 μM with the low detection limit of 28.6 nM. Meanwhile, TPE-GHK exhibited the excellent biocompatibility and low toxicity and was successfully applied in monitoring Hg2+ in living CAKI 2 cells, which demonstrated its potential application in environment and biological science. More importantly, TPE-GHK could be used to detect Hg2+ in two real water samples and also was successfully designed as test strips.

Graphical abstract

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

Price includes VAT (USA)
Tax calculation will be finalised during checkout.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

References

  1. Clarkson TW, Magos L, Myers GJ. The toxicology of mercury–current exposures and clinical manifestations. N Engl J Med. 2003;349:1731–7.

    CAS  PubMed  Article  Google Scholar 

  2. Renzoni A, Zino F, Franchi E. Mercury levels along the food chain and risk forexposed populations. Environ Res. 1998;77:68–72.

    CAS  PubMed  Article  Google Scholar 

  3. Watras C, Back R, Halvorsen S, Hudson R, Morrison K, Wente S. Bioaccumulation of mercury in pelagic freshwater food webs. Sci Total Environ. 1998;219:183–208.

    CAS  PubMed  Article  Google Scholar 

  4. Wolfe MF, Schwarzbach S, Sulaiman RA. Effects of mercury on wildlife: a comprehensive review. Environ Toxicol Chem. 1998;17:146–60.

    CAS  Article  Google Scholar 

  5. Kim HN, Ren WX, Kim JS, Yoon J. Fluorescent and colorimetric sensors for detection of lead cadmium, and mercury ions. Chem Soc Rev. 2012;41:3210–44.

    CAS  PubMed  Article  Google Scholar 

  6. Yang YK, Yook KJ, Tae J. A rhodamine–based fluorescent and colorimetric chemodosimeter for the rapid detection of Hg2+ ions in aqueous media. J Am Chem Soc. 2005;127:16760–1.

    CAS  PubMed  Article  Google Scholar 

  7. Coskun A, Akkaya EU. Signal ratio amplification via modulation of resonance energy transfer: proof of principle in an emission ratiometric Hg (II) sensor. J Am Chem Soc. 2006;128:14474–5.

    CAS  PubMed  Article  Google Scholar 

  8. Yuan G, Lv HH, Liu H, He HP, Sun Q, Zhang XH, et al. Hemicyanine–based colorimetric and near-infrared fluorescent off–on probe for Hg2+ detection and imaging in living cells and zebrafish. Dyes Pigments. 2020;183:108674.

    CAS  Article  Google Scholar 

  9. Lv HS, Sun HY. A novel coumarin–benzopyrylium based near–infrared fluorescent probe for Hg2+ and its practical applications. Spectrochim Acta Part A. 2022;267:120527.

    CAS  Article  Google Scholar 

  10. Zhang ZW, Zhang D, Guo J, Li M, Wang TL, Yin HY, et al. An anthraquinone–based “turn–on” fluorescence probe for Hg2+ detection and its application in cell imaging. Inorg Chem Commun. 2021;130:108753.

    Article  CAS  Google Scholar 

  11. Meng XY, Wang JB, Li X, Sun Q, Tu QD, Liu XH, et al. A large Stokes shift probe based enhanced ICT strategy for Hg2+–detection in cancer cells and zebrafish. Microchem J. 2021;169:106551.

    CAS  Article  Google Scholar 

  12. Zhang Y, Liu CY, Su MJ, Rong XD, Wang X, Wang K, et al. A highly selective barbiturate-based fluorescent probe for detecting Hg2+ in cells and zebrafish as well as in real water samples. J Photochem Photobiol A Chem. 2022;425:113706.

    CAS  Article  Google Scholar 

  13. Liu JF, Li J, Tang J, Yang XP, Zhang D, Zhang Y, et al. Mitochondria-targeted NIR fluorescent probe for sensing Hg2+/HSO3− and its intracellular applications. Talanta. 2021;234:122606.

    CAS  PubMed  Article  Google Scholar 

  14. Zhao M, Guo YS, Fu GD, Wang Q, Sheng WL, Guo DS. Development of a Si–rhodamine–based NIR fluorescence probe for highly specific and quick response of Hg2+ and its applications to biological imaging. Microchem J. 2021;171:106855.

    CAS  Article  Google Scholar 

  15. Liu B, Liu J, He JP, Zhang JS, Zhou HJ, Gao C. A novel red–emitting fluorescent probe for the highly selective detection of Hg2+ ion with AIE mechanism. Chem Phys. 2020;539:110944.

    CAS  Article  Google Scholar 

  16. Wen D, Deng XK, Xu GN, Wu HR, Yu YH. A novel FRET fluorescent probe based on BODIPY–rhodamine system for Hg2+ imaging in living cells. J Mol Struct. 2021;1236:130323.

    CAS  Article  Google Scholar 

  17. Jiang YH, Li HW, Chen RF, Liu W, Chen CY, Li ZG, et al. Novel fluorescent probe based on dicoumarin for rapid on–site detection of Hg2+ in loess. Spectrochim Acta Part A. 2021;251:119438.

    CAS  Article  Google Scholar 

  18. Neupane LN, Neupane JY, Park JH, Park KH. Turn–on fluorescent chemosensor based on an amino acid for Pb (II) and Hg (II) ions in aqueous solutions and role of tryptophan for sensing. Org Lett. 2013;15:254–7.

    CAS  PubMed  Article  Google Scholar 

  19. Wang P, An Y, Wu J. Highly sensitive turn-on detection of mercury(II) in aqueous solutions and live cells with a chemosensor based on tyrosine. Spectrochim Acta Part A. 2020;230:118004.

    CAS  Article  Google Scholar 

  20. Lohani R, Neupane LN, Kim JM, Kim KH. Selectively and sensitively monitoring Hg2+ in aqueous buffer solutions with fluorescent sensors based on unnatural amino acids. Sensors Actuators B Chem. 2012;161:1088–96.

    CAS  Article  Google Scholar 

  21. Wang P, Xue SR, Yang XP. Highly selective and sensitive detection of hydrogen sulfide in aqueous medium and live cells using peptide–based bioprobe to mimic the binding sites of the ceruloplasmin for Cu(II) ions. Biosens Bioelectron. 2020;163:112283.

    CAS  PubMed  Article  Google Scholar 

  22. Yang MH, Thirupathi P, Lee KH. Selective and sensitive ratiometric detection of Hg (II) ions using a simple amino acid based sensor. Org Lett. 2011;13:5028–31.

    CAS  PubMed  Article  Google Scholar 

  23. Wang P, Sun LY, Wu J, Yang XP, Lin PC, Wang M. A dual–functional colorimetric and fluorescent peptide–based probe for sequential detection of Cu2+ and S2- in 100% aqueous buffered solutions and living cells. J Hazard Mater. 2021;407:124388.

    CAS  PubMed  Article  Google Scholar 

  24. Neupane LN, Lee KH. Selective and sensitive turn on detection of Hg2+ in aqueous solution using a thioether–appended dipeptide. Tetrahedron Lett. 2013;54:5007–10.

    CAS  Article  Google Scholar 

  25. Lohani CR, Kim JM, Lee KH. Two dansyl fluorophores bearing amino acid for monitoring Hg2+ in aqueous solution and live cells. Tetrahedron. 2011;67:4130–6.

    CAS  Article  Google Scholar 

  26. Neupane LN, Kim JM, Lohani CR, Lee KH. Selective and sensitive ratiometric detection of Hg2+ in 100% aqueous solution with triazole–based dansyl probe. J Mater Chem. 2012;22:4003–8.

    CAS  Article  Google Scholar 

  27. Wang P, Xue SR, Zhou DG, Guo ZQ, Wang QF, Guo BX, et al. Peptide–based colorimetric and fluorescent dual-functional probe for sequential detection of copper(II) and cyanide ions and its application in real water samples, test strips and living cells. Spectrochim Acta Part A. 2022;276:121222.

    CAS  Article  Google Scholar 

  28. Luo J, Xie Z, Lam JWY, Cheng L, Chen H, Qiu C, et al. Aggregation–induced emission of 1–methyl–1,2,3,4,5–pentaphenylsilole. Chem Commun. 2001;18:1740–1.

    Article  Google Scholar 

  29. Alam P, Leung NLC, Zhang J, Kwok RTK, Lam JWY, Tang BZ. AIE–based luminescence probes for metal ion detection. Coord Chem Rev. 2021;429:213693.

    CAS  Article  Google Scholar 

  30. Zhang Q, Zhang P, Gong Y, Ding CF. Two–photon AIE based fluorescent probe with large stokes shift for selective and sensitive detection and visualization of hypochlorite. Sensors Actuators B Chem. 2019;278:73–81.

    CAS  Article  Google Scholar 

  31. Wu YQ, Wen XY, Fan ZF. An AIE active pyrene based fluorescent probe for selective sensing Hg2+ and imaging in live cells. Spectrochim Acta Part A. 2019;223:117315.

    CAS  Article  Google Scholar 

  32. Yang JT, Yang BS, Wen GM, Liu B. Dual sites fluorescence probe for H2S and Hg2+ with “AIE transformers” function. Sensors Actuators B Chem. 2019;296:126670.

    CAS  Article  Google Scholar 

  33. Clark M, Cramer RD III, Cramer NV III. Validation of the general purpose Tripos 5.2 force field. J Comput Chem. 1989;10:982–1012.

    CAS  Article  Google Scholar 

  34. Humphrey W, Humphrey A, Schulten K. VMD: visual molecular dynamics. J Mol Graph Model. 1996;14:33–8.

    CAS  Article  Google Scholar 

  35. Lee C, Yang W, Parr RG. Development of the Colle–Salvetti correlation–energy formula into a functional of the electron density. Phys Rev B. 1988;37:785–9.

    CAS  Article  Google Scholar 

  36. Beck AD, Density–functional thermochemistry. I. The effect of the exchange-only gradient correction. J Chem Phys. 1993;98:5648–52.

    Article  Google Scholar 

  37. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb M.A, Cheeseman JR, et al. Gaussian 09, Revision A.01, Gaussian, Inc.,Wallingford, CT, 2009.

  38. Zucchero AJ, McGrier PL, Bunz UHF. Cross-conjugated cruciform fluorophores. Acc Chem Res. 2010;43:397–408.

    CAS  PubMed  Article  Google Scholar 

  39. Stobiecka M, Molinero AA, Chałupa A, Hepel M. Mercury/homocysteine ligation–induced ON/OFF–switching of a T–T mismatch–based oligonucleotide molecular beacon. Anal Chem. 2012;84:4970–8.

    CAS  PubMed  Article  Google Scholar 

  40. Stobiecka M, Chałupa A. Biosensors based on molecular beacons. Chem Pap. 2015;69(1):62–76.

    CAS  Article  Google Scholar 

  41. Stobiecka M, Dworakowska B, Jakielaa S, Lukasiaka A, Chałupa A, Zembrzycki K. Sensing of survivin mRNA in malignant astrocytes using graphene oxide nanocarrier–supported oligonucleotide molecular beacons. Sensors Actuators B Chem. 2016;235:136–45.

    CAS  Article  Google Scholar 

  42. Stobiecka M, Ratajczak K, Jakiela S. Toward early cancer detection: Focus on biosensing systems and biosensors for an anti–apoptotic protein survivin and survivin mRNA. Biosens Bioelectron. 2019;137:58–71.

    CAS  PubMed  Article  Google Scholar 

  43. Stobiecka M. Novel plasmonic field–enhanced nanoassay for trace detection of proteins. Biosens Bioelectron. 2014;55:379–85.

    CAS  PubMed  Article  Google Scholar 

  44. Stobiecka M, Chałupa A. Modulation of plasmon–enhanced resonance energy transfer to gold nanoparticles by protein survivin channeled–shell gating. J Phys Chem B. 2015;119:13227–35.

    CAS  PubMed  Article  Google Scholar 

Download references

Funding

This work was supported by the Application Foundation Project of Science and Technology Department of Sichuan Province (No. 2021YJ0409, 2021YJ0323), the Opening Project of Key Laboratories of Fine Chemicals and Surfactants in Sichuan Provincial Universities (No. 2021JXY02), and the Fundamental Research Funds of China West Normal University (No. CXTD2020-1).

Author information

Authors and Affiliations

  1. Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Shida Road 1#, Nanchong, 637009, People’s Republic of China

    Peng Wang, Bo Chen & Fang Liao

  2. Key Laboratories of Fine Chemicals and Surfactants in Sichuan Provincial Universities, Zigong, 643002, People’s Republic of China

    Peng Wang

  3. School of Journalism and Communications, China West Normal University, Shida Road 1#, Nanchong, 637009, People’s Republic of China

    Shirui Xue

Authors
  1. Peng Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shirui Xue
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bo Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fang Liao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Peng Wang or Fang Liao.

Ethics declarations

Conflict of interest

The authors declare co competing interests.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1(DOC 3279 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Wang, P., Xue, S., Chen, B. et al. A novel peptide-based fluorescent probe for highly selective detection of mercury (II) ions in real water samples and living cells based on aggregation-induced emission effect. Anal Bioanal Chem 414, 4717–4726 (2022). https://doi.org/10.1007/s00216-022-04094-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-022-04094-4

Keywords

  • Tripeptide
  • Fluorescent probe
  • Hg(II) ions
  • Aqueous solutions
  • Cells imaging