Skip to main content
SpringerLink
Log in

A Water-Soluble Fluorescent Probe for the Selective Sensing of Ag+ and its Application in Imaging of Living Cells and Nematodes

  • ORIGINAL ARTICLE
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

In this study, an imidazole-coumarin based fluorescent probe was developed for the selective and sensitive detection of Ag+ in aqueous solution. Using a combination of Job plot, NMR titrations, and DFT calculations, the binding properties between Ag+ and the probe were deeply investigated, and the results revealed a 1:1 binding stoichiometry between the probe and Ag+ with a binding constant of 1.02 × 106 M−1. The detection limit was found to be 150 nM, which satisfies the requirement for the quantitative detection of Ag+ in real water samples. Moreover, the new probe, Ic, was successfully applied to sense Ag+ in HeLa and HepG2 cells as well as in C. elegans, indicating that it could be a useful tool for the environmental monitoring of Ag+ pollution. These results demonstrated that Ic could serve as a high-efficiency and low-cost fluorescent probe for tracking Ag+ in an aquatic environment and biological organisms.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

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

Similar content being viewed by others

References

  1. Kursunlu AN, Ozmen M, Guler E (2016) Novel magnetite nanoparticle based on BODIPY as fluorescent hybrid material for Ag(I) detection in aqueous medium. Talanta 153:191–196

    CAS  PubMed  Google Scholar 

  2. Huang GW, Xiao HM, Fu SY (2014) Paper-based silver-nanowire electronic circuits with outstanding electrical conductivity and extreme bending stability. Nanoscale 6:8495–8502

    CAS  PubMed  Google Scholar 

  3. Drake PL, Hazelwood KJ (2005) Exposure-related health effects of silver and silver compounds: a review. Ann Occup Hyg 49:575–585

    CAS  PubMed  Google Scholar 

  4. Silver S, Lo J, Gupta (1999) A silver cations as an antimicrobial agent: clinical uses and bacterial resistance. APUA Newsletter 17:1–3

  5. Purcell TW, Peters JJ (1998) Sources of silver in the environment. Environ Toxicol Chem 17:539–546

    CAS  Google Scholar 

  6. Ratte HT (1999) Bioaccumulation and toxicity of silver compounds: a review. Environ Toxicol Chem 18:89–108

    CAS  Google Scholar 

  7. Bian L, Ji X, Hu W (2014) A novel single-labeled fluorescent oligonucleotide probe for silver(I) ion detection in water, drugs, and food. J Agric Food Chem 62:870–4877

    Google Scholar 

  8. Monteiro DR, Gorup LF, Takamiya AS, Ruvollo-Filho AC, de Camargo ER, Barbosa DB (2009) The growing importance of materials that prevent microbial adhesion: antimicrobial effect of medical devices containing silver. Int J Antimicrob Agents 34:103–110

    CAS  PubMed  Google Scholar 

  9. Siddiqi KS, Husen A, Rao RAK (2018) A review on biosynthesis of silver nanoparticles and their biocidal properties. J Nanobiotechnology 16:14

    PubMed  PubMed Central  Google Scholar 

  10. Li Y, Yu HJ, Shao G, Gan F (2015) A tetraphenylethylene-based “turn on” fluorescent sensor for the rapid detection of Ag+ ions with high selectivity. J Photoch Photobio A 301:14–19

    CAS  Google Scholar 

  11. Wan T, Conyers RA, Coombs CJ, Masterton JP (1991) Determination of silver in blood, urine and tissues of volunteers and burn patients. Clin Chem 37:1683–1687

    CAS  PubMed  Google Scholar 

  12. Järup L (2003) Hazards of heavy metal contamination. Br Med Bull 68:167–182

    PubMed  Google Scholar 

  13. Zhang JF, Zhou Y, Yoon J, Kim JS (2011) Recent progress in fluorescent and colorimetric chemosensors for detection of precious metal ions (silver, gold and platinum ions). Chem Soc Rev 40:3416–3429

    CAS  PubMed  Google Scholar 

  14. Lai Q, Liu Q, He Y, Zhao K, Wei C, Wojtas L, Shi X, Song Z (2018) Triazole-imidazole (TA-IM) derivatives as ultrafast fluorescent probes for selective Ag+ detection. Org Biomol Chem 16:7801–7805

    CAS  PubMed  PubMed Central  Google Scholar 

  15. Li DH, Shen JS, Chen N, Ruan YB, Jiang YB (2011) A ratiometric luminescent sensing of Ag+ ion via in situ formation of coordination polymers. Chem Commun (Camb) 47:5900–5902

    CAS  Google Scholar 

  16. Hu M, Fan J, Cao J, Song K, Zhang H, Sun S, Peng X (2012) Enhanced fluorescent chemosensor for Ag+ in absolute aqueous solution and living cells: an experimental and theoretical study. Analyst 137:2107–2111

    CAS  PubMed  Google Scholar 

  17. Maurya N, Bhardwaj S, Singh AK (2017) Selective colorimetric and fluorescence ‘turn-on’ sensor for Ag+ and in-situ sensing of CN- (off-on-off) via displacement approach. Mater Sci Eng C Mater Biol Appl 74(2017):55–61

    CAS  PubMed  Google Scholar 

  18. Lum JT, Leung KS (2019) Quantifying silver nanoparticle association and elemental content in single cells using dual mass mode in quadrupole-based inductively coupled plasma-mass spectrometry. Anal Chim Acta 1061:50–59

    CAS  PubMed  Google Scholar 

  19. Gao Y, Hu Z, Wu J, Ning Z, Jian J, Zhao T, Liang X, Yang X, Yang Z, Zhao Q, Wang J, Wang Z, Dina NE, Gherman AMR, Jiang Z, Zhou H (2019) Size-tunable Au@Ag nanoparticles for colorimetric and SERS dual-mode sensing of palmatine in traditional Chinese medicine. J Pharm Biomed Anal 174:123–133

    CAS  PubMed  Google Scholar 

  20. Feichtmeier NS, Leopold K (2014) Detection of silver nanoparticles in parsley by solid sampling high-resolution-continuum source atomic absorption spectrometry. Anal Bioanal Chem 406:3887–3894

    CAS  PubMed  Google Scholar 

  21. Omidi F, Behbahani M, Shahtaheri SJ, Salimi S (2015) Trace monitoring of silver ions in food and water samples by flame atomic absorption spectrophotometry after preconcentration with solvent-assisted dispersive solid phase extraction. Environ Monit Assess 187:361

    PubMed  Google Scholar 

  22. Tang J, Chen W, Ju H (2019) Sensitive surface-enhanced Raman scattering detection of atrazine based on aggregation of silver nanoparticles modified carbon dots. Talanta 201:46–51

    CAS  PubMed  Google Scholar 

  23. Lim Z, Smith DG, Kolanowski JL, Mattison RL, Knowles JC, Baek SY, Chrzanowski W, New EJ (2018) A reversible fluorescent probe for monitoring Ag(I) ions. J R Soc Interface 15

  24. Ono A, Cao S, Togashi H, Tashiro M, Fujimoto T, Machinami T, Oda S, Miyake Y, Okamoto I, Tanaka Y (2008) Specific interactions between silver(I) ions and cytosine-cytosine pairs in DNA duplexes. Chem Commun (Camb) 39:4825–4827

    Google Scholar 

  25. Wang L, Zhang Y, Dong Y (2018) A multifunctional molecular probe for detecting Hg2+ and Ag+ based on ion-mediated base mismatch. Sensors (Basel) 18

  26. Tsukamoto K, Shinohara Y, Iwasaki S, Maeda H (2011) A coumarin-based fluorescent probe for Hg2+ and Ag+ with an N'-acetylthioureido group as a fluorescence switch. Chem Commun (Camb) 47:5073–5075

    CAS  Google Scholar 

  27. Chatterjee A, Santra M, Won N, Kim S, Kim JK, Kim SB, Ahn KH (2009) Selective fluorogenic and chromogenic probe for detection of silver ions and silver nanoparticles in aqueous media. J Am Chem Soc 131:2040–2041

    CAS  PubMed  Google Scholar 

  28. Zhang Y, Ye A, Yao Y, Yao C (2019) A sensitive near-infrared fluorescent probe for detecting heavy metal Ag+ in water samples. Sensors (Basel) 19

  29. Tabaraki R, Nateghi A (2016) Nitrogen-doped graphene quantum dots: “turn-off” fluorescent probe for detection of Ag(+) ions. J Fluoresc 26:297–305

    CAS  PubMed  Google Scholar 

  30. Hammud HH, El Shazly S, Sonji G, Sonji N, Bouhadir KH (2015) Thiophene aldehyde-diamino uracil Schiff base: a novel fluorescent probe for detection and quantification of cupric, silver and ferric ions. Spectrochim Acta A Mol Biomol Spectrosc 150:94–103

    CAS  PubMed  Google Scholar 

  31. Chen ZE, Zhang H, Iqbal Z (2019) A new thiosemicarbazone fluorescent probe based on ,9′-bianthracene for Hg2+ and Ag+. Spectrochim Acta A Mol Biomol Spectrosc 215:34–40

    CAS  PubMed  Google Scholar 

  32. Ye F, Liang XM, Xu KX, Pang XX, Chai Q, Fu Y (2019) A novel dithiourea-appended naphthalimide “on-off” fluorescent probe for detecting Hg2+ and Ag+ and its application in cell imaging. Talanta 200:494–502

    CAS  PubMed  Google Scholar 

  33. Xu L, Yang X, Ding H, Li S, Li M, Wang D, Xia J (2019) Synthesis of green fluorescent carbon materials using byproducts of the sulfite-pulping procedure residue for live cell imaging and Ag+ ion determination. Mater Sci Eng C Mater Biol Appl 102:917–922

    CAS  PubMed  Google Scholar 

  34. Bhorge YR, Chou TL, Chen YZ, Yen YP (2015) New coumarin-based dual chromogenic probe: naked eye detection of copper and silver ions. Sensors Actuators B 220:1139–1144

    CAS  Google Scholar 

  35. El-Shekheby HA, Mangood AH, Hamza SM, Al-Kady AS, Ebeid e-ZM (2014) A highly efficient and selective turn-on fluorescent sensor for Hg2+, Ag+ and Ag nanoparticles based on a coumarin dithioate derivative. Luminescence 29:158–167

    CAS  PubMed  Google Scholar 

  36. Katerinopoulos HE (2004) The coumarin moiety as chromophore of fluorescent ion indicators in biological systems. Curr Pharm Des 10:3835–3852

    CAS  PubMed  Google Scholar 

  37. Li J, Li XK, Jia JB, Chen X, Lv YJ, Guo Y, Li J (2019) A ratiometric near-infrared fluorescence strategy based on spiropyran in situ switching for tracking dynamic changes of live-cell lysosomal pH. Dyes Pigments. https://doi.org/10.1016/j.dyepig.2019.03.060

    CAS  Google Scholar 

  38. Wang F, Nandhakumar R, Moon JH, Kim KM, Lee JY, Yoon J (2011) Ratiometric fluorescent chemosensor for silver ion at physiological pH. Inorg Chem 50:2240–2245

    CAS  PubMed  Google Scholar 

  39. Khilya OV, Frasinyuk MS, Turov AV, Khilya VP (2001) Chemistry of 3-Hetarylcoumarins. 1. 3-(2-Benzazolyl)coumarins. Chem Heterocycl Compd 37(2001):1029–1037

    CAS  Google Scholar 

  40. Bian W, Zhang H, Yu Q, Shi M, Shuang S, Cai Z, Choi MM (2016) Detection of Ag(+) using graphite carbon nitride nanosheets based on fluorescence quenching. Spectrochim Acta A Mol Biomol Spectrosc 169:122–127

    CAS  PubMed  Google Scholar 

  41. Cen MJ, Chang T, Yin YB, Li XL, He YW (2018) A novel ratiometric fluorescent sensor for Ag+ based on two fluorophores. Methods Appl Fluoresc 6:5005

    Google Scholar 

  42. Fang Q, Tian HH, Yang L, Chen S, Liu XJ, Song XZ (2018) A thiocoumarin-based fluorescent probe for detection of hypochlorite with high selectivity over other typical desulfurizing agents (Hg 2+/Ag+). Sensors Actuators B Chem 260:146–155

    CAS  Google Scholar 

  43. Yang Z, She M, Yin B, Hao L, Obst M, Liu P, Li J (2015) Solvent-dependent turn-on probe for dual monitoring of Ag(+) and Zn(2+) in living biological samples. Anal Chim Acta 868:53–59

    CAS  PubMed  Google Scholar 

  44. Li WT, Wu GY, Qu WJ, Li Q, Lou JC, Lin Q, Yao H, Zhang YM, Wei TB (2017) A colorimetric and reversible fluorescent chemosensor for Ag + in aqueous solution and its application in IMPLICATION logic gate. Sensors Actuators B Chem 239:671–678

    CAS  Google Scholar 

  45. Zhang E, Ju P, Li Q, Hou X, Yang H, Yang XJ, Zong Y, Zhang YQ (2018) A novel rhodamine 6G-based fluorescent and colorimetric probe for Bi3+: synthesis, selectivity, sensitivity and potential applications. Sensors Actuators B Chem 260:204–212

    CAS  Google Scholar 

  46. Wang L, Bing QJ, Li JX, Wang G (2018) A new “ON-OFF” fluorescent and colorimetric chemosensor based on 1,3,4-oxadiazole derivative for the detection of Cu2+ ions. J Photoch Photobio A 360:86–94

    Google Scholar 

  47. Abdel-Gaber R, Abdel-Ghaffar F, Abdallah Shazly M, Morsy K, Quraishy SA, Mohamed S, Mehlhorn H (2017) Morphological re-description of Electrotaenia malapteruri (Cestoda: Proteocephalidae) and Dujardinnascaris malapteruri (Nematoda: Heterocheilidae) infecting the electric catfish Malapterurus electricus and heavy metal accumulation in host and parasites in relation to water and sediment analysis in Lake Manzala, North Delta, Egypt. Acta Parasitol 62:319–335

    CAS  PubMed  Google Scholar 

  48. Mutwakil MH, Reader JP, Holdich DM, Smithurst PR, Candido EPM, Jones D, Stringham EG, de Pomerai DI (1997) Use of stress-inducible transgenic nematodes as biomarkers of heavy metal pollution in water samples from an English River system. Arch Environ Contam Toxicol 32:146–153

    CAS  PubMed  Google Scholar 

Download references

Acknowledgments

This work was supported by Grants from the National Science and Technology Major Project of the Ministry of Science and Technology of China (2018ZX09721004-006), the Administration of Traditional Chinese Medicine of Sichuan Province (2018JC013), the Science and Technology Planning Project of Sichuan Province (2016JY0101, 2017JQ0052, 2018JY0237, 2019JDPT0010), the Joint Fund of Luzhou City and Southwest Medical University (2015LZCYD-S01, 2018LZXNYD-ZK18, 2018LZXNYD-ZK28), the Educational Commission of Sichuan Province (18ZA0528, 18TD0051), the Open Program of Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province (HYX18010, HYX19018), and the Health Commission of Sichuan Province (18PJ019). We gratefully acknowledge Dr. Zengjin Liu for assistance in probe synthesis.

Author information

Authors and Affiliations

  1. The Pharmacy School of Southwest Medical University, Luzhou, China

    Xueqin Jiang, Xiaogang Zhou, Jianming Wu & Sicheng Liang

  2. The Affiliated Hospital of Southwest Medical University, Luzhou, China

    Youzhe Yang, Hao Li, Xiaoyi Qi, Mingming Deng, Muhan Lü & Sicheng Liang

  3. The Sichuan Key Medical Laboratory of New Drug Discovery and Drug Ability Evaluation, Luzhou, China

    Jianming Wu

  4. Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province, Luzhou, China

    Xiaoyi Qi & Sicheng Liang

Authors
  1. Xueqin Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Youzhe Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hao Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiaoyi Qi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xiaogang Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Mingming Deng
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Muhan Lü
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Jianming Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Sicheng Liang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Muhan Lü, Jianming Wu or Sicheng Liang.

Ethics declarations

Conflict of Interest

The authors have no conflicts of interest to declare.

Additional information

Publisher’s Note

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

Electronic supplementary material

ESM 1

(DOC 398 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jiang, X., Yang, Y., Li, H. et al. A Water-Soluble Fluorescent Probe for the Selective Sensing of Ag+ and its Application in Imaging of Living Cells and Nematodes. J Fluoresc 30, 121–129 (2020). https://doi.org/10.1007/s10895-019-02477-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-019-02477-y

Keywords

Search

Navigation