Skip to main content
SpringerLink
Log in

Polyphosphoric acid-induced perylene probe self-assembly and label-free fluorescence turn-on detection of alkaline phosphatase

  • Research Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

A label-free fluorescence turn-on strategy for alkaline phosphatase (ALP) detection was established based on its enzymatic catalyzed hydrolysis of polyphosphoric acid (PPA, an anionic polymer) that had been utilized for aggregation with our homemade positively charged perylene derivative (Probe-1) via noncovalent interactions. The disaggregation caused turn-on fluorescence signal which was recovered by the released Proble-1 molecules whose original strong fluorescence in an aqueous buffer solution had been quenched due to their previous aggregation induced by PPA. Such method presents its great advantages of free labeling, convenience and simplicity, cost effectiveness, high selectivity, and high sensitivity, with a detection limit of 0.5 mU/mL of ALP.

A label-free fluorescence turn-on strategy for alkaline phosphatase based on its enzymatic catalyzed hydrolysis of polyphosphoric acid that had been utilized for aggregation with our homemade positively charged perylene derivative via noncovalent interactions

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

Similar content being viewed by others

References

  1. Millan JL. Alkaline phosphatases: structure, substrate specificity and functional relatedness to other members of a large superfamily of enzymes. Purin Signal. 2006;2:335–41.

    Article  CAS  Google Scholar 

  2. Coleman JE. Structure and mechanism of alkaline-phosphatase. Annu Rev Biophys Biomol Struct. 1992;21:441–83.

    Article  CAS  Google Scholar 

  3. Cheung CL, Tan KCB, Lam KSL, Cheung BMY. The relationship between glucose metabolism, metabolic syndrome and bone-specific alkaline phosphatase: a structural equation modeling approach. J Clin Endocrinol Metab. 2013;98:3856–63.

    Article  CAS  Google Scholar 

  4. Colombatto P, Randone A, Civitico G, Gorin JM, Dolci L, Medaina N, et al. Hepatitis G virus RNA in the serum of patients with elevated gamma glutamyl transpeptidase and alkaline phosphatase: a specific liver disease. J Viral Hepat. 1996;3:301–6.

    Article  CAS  Google Scholar 

  5. Ooi K, Shiraki K, Morishita Y, Nobori T. High-molecular intestinal alkaline phosphatase in chronic liver diseases. J Clin Lab Anal. 2007;21:133–9.

    Article  CAS  Google Scholar 

  6. Couttenye MM, Dhaese PC, VanHoof VO, Lemoniatou E, Goodman W, Verpooten GA, et al. Low serum levels of alkaline phosphatase of bone origin: a good marker of adynamic bone disease in haemodialysis patients. Nephrol Dial Transplant. 1996;11:1065–72.

    Article  CAS  Google Scholar 

  7. Ramaswamy G, Rao VR, Krishnamoorthy L, Ramesh G, Gomathy R, Renukadevi D. Serum levels of bone alkaline phosphatase in breast and prostate cancers with bone metastasis. Indian J Clin Biochem. 2000;15:110–3.

    Article  CAS  Google Scholar 

  8. Nie F, Luo K, Zheng X, Zheng J, Song Z. Novel preparation and electrochemiluminescence application of luminol functional-Au nanoclusters for ALP determination. Sensor Actuat B. 2015;218:152–9.

    Article  CAS  Google Scholar 

  9. Yu L, Shi Z, Fang C, Zhang Y, Liu Y, Li C. Disposable lateral flow-through strip for smartphone-camera to quantitatively detect alkaline phosphatase activity in milk. Biosens Bioelectron. 2015;69:307–15.

    Article  CAS  Google Scholar 

  10. Goggins S, Naz C, Marsh BJ, Frost CG. Ratiometric electrochemical detection of alkaline phosphatase. Chem Commun. 2015;51:561–4.

    Article  CAS  Google Scholar 

  11. Ruan CM, Wang W, Gu BH. Detection of alkaline phosphatase using surface-enhanced Raman spectroscopy. Anal Chem. 2006;78:3379–84.

    Article  CAS  Google Scholar 

  12. Li Y, Li YN, Liu ZG, Su XG. Sensitive fluorometric detection of alkaline phosphatase using a water-soluble conjugated polymer. RSC Adv. 2014;4:42825–30.

    Article  CAS  Google Scholar 

  13. Wu CS, Oo MKK, Fan X. Highly sensitive multiplexed heavy metal detection using quantum-dot-labeled DNAzymes. ACS Nano. 2010;4:5897–904.

    Article  CAS  Google Scholar 

  14. Zhang H, Xu C, Liu J, Li X, Guo L, Li X. An enzyme-activatable probe with a self-immolative linker for rapid and sensitive alkaline phosphatase detection and cell imaging through a cascade reaction. Chem Commun. 2015;51:7031–4.

    Article  CAS  Google Scholar 

  15. Wang Y, Chen J, Chen Y, Li WY, Yu C. Polymer-induced perylene probe excimer formation and selective sensing of DNA methyltransferase activity through the monomer-excimer transition. Anal Chem. 2014;86:4371–8.

    Article  CAS  Google Scholar 

  16. An L, Tang Y, Feng F, He F, Wang S. Water-soluble conjugated polymers for continuous and sensitive fluorescence assays for phosphatase and peptidase. J Mater Chem. 2007;17:4147–52.

    Article  CAS  Google Scholar 

  17. Gonzalez-Gil S, Keafer BA, Jovine RVM, Aguilera A, Lu S, Anderson DM. Detection and quantification of alkaline phosphatase in single cells of phosphorus-starved marine phytoplankton. Mar Ecol Prog Ser. 1998;164:21–35.

    Article  CAS  Google Scholar 

  18. Craig DB, Wong JCY, Dovichi NJ. Detection of attomolar concentrations of alkaline phosphatase by capillary electrophoresis using laser-induced fluorescence detection. Anal Chem. 1996;68:697–700.

    Article  CAS  Google Scholar 

  19. Park L, Bae H, Kim YT, Lee JH. Rapid monitoring of alkaline phosphatase in raw milk using 1,10-oxalyldiimidazole chemiluminescence detection. Method Anal. 2011;3:156–60.

    Article  CAS  Google Scholar 

  20. Chen Y, Li WY, Wang Y, Yang X, Chen J, Jiang Y, et al. Cysteine-directed fluorescent gold nanoclusters for the sensing of pyrophosphate and alkaline phosphatase. J Mater Chem. 2014;2:4080–5.

    Article  CAS  Google Scholar 

  21. Qian Z, Chai L, Tang C, Huang Y, Chen J, Feng H. Carbon quantum dots-based recyclable real-time fluorescence assay for alkaline phosphatase with adenosine triphosphate as substrate. Anal Chem. 2015;87:2966–73.

    Article  CAS  Google Scholar 

  22. Jiao H, Wang B, Chen J, Liao D, Yu C. Label free fluorescence turn-on detection of polynucleotide kinase activity with a perylene probe. Chem Commun. 2012;48:7862–4.

    Article  CAS  Google Scholar 

  23. Chen J, Jiao HP, Li WY, Liao DL, Zhou HP, Yu C. Real-time fluorescence turn-on detection of alkaline phosphatase activity with a novel perylene probe. Chem Asian J. 2013;8:276–81.

    Article  CAS  Google Scholar 

  24. Wang B, Yu C. Fluorescence turn-on detection of a protein through the reduced aggregation of a perylene probe. Angew Chem Int Ed. 2010;49:1485–8.

    Article  CAS  Google Scholar 

  25. Wang B, Jiao HP, Li WY, Liao DL, Wang FY, Yu C. Superquencher formation via nucleic acid induced noncovalent perylene probe self-assembly. Chem Commun. 2011;47:10269–71.

    Article  CAS  Google Scholar 

  26. Wang B, Wang FY, Jiao HP, Yang X, Yu C. Label-free selective sensing of mercury(II) via reduced aggregation of the perylene fluorescent probe. Analyst. 2010;135:1986–91.

    Article  CAS  Google Scholar 

  27. Yang Y, Li WY, Qi H, Zhang QF, Chen J, Wang Y, et al. Detection of silver(I) ions based on the controlled self-assembly of a perylene fluorescence probe. Anal Biochem. 2012;430:48–52.

    Article  CAS  Google Scholar 

  28. Liao DL, Li WY, Chen J, Jiao HP, Zhou HP, Wang B, et al. Sensing of a nucleic acid binding protein via a label-free perylene probe fluorescence recovery assay. Anal Chim Acta. 2013;797:89–94.

    Article  CAS  Google Scholar 

  29. Li YX, Zhou HP, Chen J, Shahzad SA, Yu C. Controlled self-assembly of small molecule probes and the related applications in bioanalysis. Biosens Bioelectron. 2016;76:38–53.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (21561162004, 21405151), the Natural Science Foundation of Jilin Province (20150101183JC, 20160520127JH), the Jilin Provincial Strategic Economic Infrastructure Adjustment fund (2015Y058), and the Pillar Program of Changchun Municipal Bureau of Science and Technology (14KG046). Yu D gratefully acknowledges the support from the visiting program collaborated between Danish Universities and the Chinese Academy of Sciences. Support from the Sino-Danish Centre for Education and Research (SDC) is also fully acknowledged.

Author information

Authors and Affiliations

  1. School of Chemical & Environmental Engineering, Changchun University of Science and Technology, Changchun, Jilin, 130022, China

    Wenping Zhang, Ying Gao & Xiuyun Yang

  2. State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin, 130022, China

    Wenping Zhang, Yongxin Li, Qingfeng Zhang, Zhenzhen Hu, Yunyi Zhang, Ejaz Hussain & Cong Yu

  3. University of Chinese Academy of Sciences, Beijing, 100049, China

    Wenping Zhang, Yongxin Li, Qingfeng Zhang, Zhenzhen Hu, Yunyi Zhang, Ejaz Hussain & Cong Yu

  4. Department of Chemistry and Bioscience, Aalborg University, 9220, Aalborg East, Denmark

    Donghong Yu

  5. Sino-Danish Center for Education and Research, Aarhus University, 8000, Aarhus, Denmark

    Donghong Yu

Authors
  1. Wenping Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ying Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yongxin Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Qingfeng Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhenzhen Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yunyi Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ejaz Hussain
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Xiuyun Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Donghong Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Cong Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Ying Gao, Yongxin Li, Donghong Yu or Cong Yu.

Ethics declarations

Conflict of interest

The authors declare that they have no competing interests.

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 413 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, W., Gao, Y., Li, Y. et al. Polyphosphoric acid-induced perylene probe self-assembly and label-free fluorescence turn-on detection of alkaline phosphatase. Anal Bioanal Chem 409, 1031–1036 (2017). https://doi.org/10.1007/s00216-016-0017-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-016-0017-8

Keywords

Search

Navigation