Skip to main content
Log in

Assay of 1-hydroxypyrene via aggregation-induced quenching of the fluorescence of protamine-modified gold nanoclusters and 9-hydroxyphenanthrene-based sensitization

  • Original Paper
  • Published:
Microchimica Acta Aims and scope Submit manuscript

Abstract

This work describes a method for the determination of 1-hydroxypyrene (OH-Py) via aggregation-induced quenching of the emission of protamine-coated gold nanoclusters using 9-hydroxyphenanthrene (OH-Phe) as a sensitizer to boost the emission efficiency of nanoprobe. Under optimum conditions, the drop in fluorescence intensity at excitation/emission wavelengths of 300/596 nm is proportional to the concentrations of OH-Py in the range from 1.0 to 65 nM. The relative standard deviations are 4.2, 2.4 and 1.9% (for n = 11) at concentration levels of 8.0, 32 and 48 nM of OH-Py, respectively. The detection limit is 0.3 nM which is much lower than that of some previously reported methods. The recoveries from urine samples spiked with OH-Py ranged between 94.4 and 98.8%.

1-Hydroxypyrene (OH-Py) can trigger the aggregation of protamine-gold nanoclusters (PRT-AuNCs), resulting in the emission quenching of PRT-AuNCs. 9-Hydroxyphenanthrene (OH-Phe) can boost the emission efficiency of nanoprobe. Thereby, a highly sensitive assay of OH-Py was established.

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Sanchez-Guerra M, Pelallo-Martinez N, Diaz-Barriga F, Rothenberg SJ, Hernandez-Cadena L, Faugeron S, Oropeza-Hernandez LF, Guaderrama-Diaz M, Quintanilla-Vega B (2012) Environmental polycyclic aromatic hydrocarbon (PAH) exposure and DNA damage in Mexican children. Mutat Res 742:66–71

    Article  CAS  Google Scholar 

  2. Jongeneelen FJ (2014) A guidance value of 1-hydroxypyrene in urine in view of acceptable occupational exposure to polycyclic aromatic hydrocarbons. Toxicol Lett 231:239–248

    Article  CAS  Google Scholar 

  3. Hansen AM, Wallin H, Binderup ML, Dybdahl M, Autrup H, Loft S, Knudsen LE (2004) Urinary 1-hydroxypyrene and mutagenicity in bus drivers and mail carriers exposed to urban air pollution in Denmark. Mutat Res 557:7–17

    Article  CAS  Google Scholar 

  4. Mattarozzi M, Musci M, Careri M, Mangia A, Fustinoni S, Campo L, Bianchi F (2009) A novel headspace solid-phase microextraction method using in situ derivatization and a diethoxydiphenylsilane fibre for the gas chromatography-mass spectrometry determination of urinary hydroxy polycyclic aromatic hydrocarbons. J Chromatogr A 1216:5634–5639

    Article  CAS  Google Scholar 

  5. Lim HH, Shin HS (2013) Simultaneous determination of 2-naphthol and 1-hydroxypyrene in fish and shellfish contaminated with crude oil by gas chromatography-mass spectrometry. Food Chem 138:791–796

    Article  CAS  Google Scholar 

  6. Makos P, Fernandes A, Boczkaj G (2018) Method for the simultaneous determination of monoaromatic and polycyclic aromatic hydrocarbons in industrial effluents using dispersive liquid-liquid microextraction with gas chromatography-mass spectrometry. J Sep Sci 41:2360–2367

    Article  CAS  Google Scholar 

  7. He XM, Zhu GT, Yin J, Zhao Q, Yuan BF, Feng YQ (2014) Electrospun polystyrene/oxidized carbon nanotubes film as both sorbent for thin film microextraction and matrix for matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. J Chromatogr A 1351:29–36

    Article  CAS  Google Scholar 

  8. Onyemauwa F, Rappaport SM, Sobus JR, Gajdosova D, Wu R, Waidyanatha S (2009) Using liquid chromatography-tandem mass spectrometry to quantify monohydroxylated metabolites of polycyclic aromatic hydrocarbons in urine. J Chromatogr B Anal Technol Biomed Life Sci 877:1117–1125

    Article  CAS  Google Scholar 

  9. Shen X, Cui Y, Pang Y, Qian H (2012) Graphene oxide nanoribbon and polyhedral oligomeric silsesquioxane assembled composite frameworks for pre-concentrating and electrochemical sensing of 1-hydroxypyrene. Electrochim Acta 59:91–99

    Article  CAS  Google Scholar 

  10. Yang DH, Lee CS, Jeon BH, Choi SM, Kim YD, Shin JS, Kim H (2017) An electrochemical nanofilm sensor for determination of 1-hydroxypyrene using molecularly imprinted receptors. J Ind Eng Chem 51:106–112

    Article  CAS  Google Scholar 

  11. Pang Y, Zhang Y, Sun X, Ding H, Ma T, Shen X (2019) Synergistical accumulation for electrochemical sensing of 1-hydroxypyrene on electroreduced graphene oxide electrode. Talanta 192:387–394

    Article  CAS  Google Scholar 

  12. Li R, Kameda T, Li Y, Toriba A, Tang N, Hayakawa K, Lin JM (2011) Hydrogen peroxide- sodium hydrosulfite chemiluminescence system combined with high-performance liquid chromatography for determination of 1-hydroxypyrene in airborne particulates. Talanta 85:2711–2714

    Article  CAS  Google Scholar 

  13. Serrano M, Bartolome M, Bravo JC, Paniagua G, Ganan J, Gallego-Pico A, Garcinuno RM (2017) On-line flow injection molecularly imprinted solid phase extraction for the preconcentration and determination of 1-hydroxypyrene in urine samples. Talanta 166:375–382

    Article  CAS  Google Scholar 

  14. Serrano M, Bartolome M, Gallego-Pico A, Garcinuno RM, Bravo JC, Fernandez P (2015) Synthesis of a molecularly imprinted polymer for the isolation of 1-hydroxypyrene in human urine. Talanta 143:71–76

    Article  CAS  Google Scholar 

  15. Kang RH, Wang YS, Yang HM, Li GR, Tan X, Xue JH, Zhang JQ, Yuan YK, Shi LF, Xiao XL (2010) Rapid simultaneous analysis of 1-hydroxypyrene, 2-hydroxyfluorene, 9-hydroxyphenanthrene, 1- and 2-naphthol in urine by first derivative synchronous fluorescence spectrometry using Tween-20 as a sensitizer. Anal Chim Acta 658:180–186

    Article  CAS  Google Scholar 

  16. Yang HM, Wang YS, Li JH, Li GR, Wang Y, Tan X, Xue JH, Xiao XL, Kang RH (2009) Synchronous fluorescence determination of urinary 1-hydroxypyrene, β-naphthol and 9-hydroxyphenanthrene based on the sensitizing effect of β-cyclodextrin. Anal Chim Acta 636:51–57

    Article  CAS  Google Scholar 

  17. Zhang ZX, Zhu YX, Zhang Y (2015) Simultaneous determination of 9-ethylphenanthrene, pyrene and 1-hydroxypyrene in an aqueous solution by synchronous fluorimetry using the double scans method and hydroxyl-propyl beta-cyclodextrin as a sensitizer. Talanta 144:836–843

    Article  CAS  Google Scholar 

  18. Wang XF, Xiang LP, Wang YS, Xue JH, Zhu YF, Huang YQ, Chen SH, Tang X (2016) A “turn-on” fluorescence assay for lead(II) based on the suppression of the surface energy transfer between acridine orange and gold nanoparticles. Microchim Acta 183:1333–1339

    Article  CAS  Google Scholar 

  19. Miao X, Cheng Z, Ma H, Li Z, Xue N, Wang P (2018) Label-free platform for microRNA detection based on the fluorescence quenching of positively charged gold nanoparticles to silver nanoclusters. Anal Chem 90:1098–1103

    Article  CAS  Google Scholar 

  20. Huang YQ, Yang LN, Wang YS, Xue JH, Chen SH (2018) Protamine-stabilized gold nanoclusters as a fluorescent nanoprobe for lead(II) via Pb(II)-au(I) interaction. Microchim Acta 185:483

    Article  Google Scholar 

  21. Liu X, Shao C, Chen T, He Z, Du G (2019) Stable silver nanoclusters with aggregation- induced emission enhancement for detection of aluminum ion. Sensors Actuators B Chem 278:181–189

    Article  CAS  Google Scholar 

  22. Shen Z, Zhang C, Yu X, Li J, Liu B, Zhang Z (2019) A facile stage for cu2+ ions detection by formation and aggregation of Cu nanoclusters. Microchem J 145:517–522

    Article  CAS  Google Scholar 

  23. Roque A, Ponte I, Suau P (2011) Secondary structure of protamine in sperm nuclei: an infrared spectroscopy study. BMC Struct Biol 11:14

    Article  CAS  Google Scholar 

  24. Huang YQ, Fu S, Wang YS, Xue JH, Xiao XL, Chen SH, Zhou B (2018) Protamine-gold nanoclusters as peroxidase mimics and the selective enhancement of their activity by mercury ions for highly sensitive colorimetric assay of hg(II). Anal Bioanal Chem 410:7385–7394

    Article  CAS  Google Scholar 

  25. Jalili R, Khataee A (2018) Aluminum(III) triggered aggregation-induced emission of glutathione-capped copper nanoclusters as a fluorescent probe for creatinine. Microchim Acta 186:29

    Article  Google Scholar 

  26. Wu Z, Liu J, Gao Y, Liu H, Li T, Zou H, Wang Z, Zhang K, Wang Y, Zhang H, Yang B (2015) Assembly-induced enhancement of cu nanoclusters luminescence with mechanochromic property. J Am Chem Soc 137:12906–12913

    Article  CAS  Google Scholar 

  27. Goswami N, Yao Q, Luo Z, Li J, Chen T, Xie J (2016) Luminescent metal nanoclusters with aggregation-induced emission. J Phys Chem Lett 7:962–975

    Article  CAS  Google Scholar 

  28. Zhao Q, Chen S, Zhang L, Huang H, Zeng Y, Liu F (2014) Multiplex sensor for detection of different metal ions based on on–off of fluorescent gold nanoclusters. Anal Chim Acta 852:236–243

    Article  CAS  Google Scholar 

  29. Wang C, Wu J, Jiang K, Humphrey MG, Zhang C (2017) Stable ag nanoclusters-based nano-sensors: rapid sonochemical synthesis and detecting Pb2+ in living cells. Sensors Actuators B Chem 238:1136–1143

    Article  CAS  Google Scholar 

  30. Durgadas CV, Sharma CP, Sreenivasan K (2011) Fluorescent gold clusters as nanosensors for copper ions in live cells. Analyst 136:933–940

    Article  CAS  Google Scholar 

  31. Ding SN, Li CM, Bao N (2015) Off-on phosphorescence assay of heparin via gold nanoclusters modulated with protamine. Biosens Bioelectron 64:333–337

    Article  CAS  Google Scholar 

  32. Ji L, Guo Y, Hong S, Wang Z, Wang K, Chen X, Zhang J, Hu J, Pei R (2015) Label-free detection of Pb2+ based on aggregation-induced emission enhancement of au-nanoclusters. RSC Adv 5:36582–36586

    Article  CAS  Google Scholar 

  33. Zhang JQ, Wang YS, Xue JH, He Y, Yang HX, Liang J, Shi LF, Xiao XL (2012) A gold nanoparticles-modified aptamer beacon for urinary adenosine detection based on structure- switching/fluorescence-"turning on" mechanism. J Pharm Biomed Anal 70:362–368

    Article  CAS  Google Scholar 

  34. Farzampour L, Amjadi M (2014) Sensitive turn-on fluorescence assay of methimazole based on the fluorescence resonance energy transfer between acridine orange and silver nanoparticles. J Lumin 155:226–230

    Article  CAS  Google Scholar 

  35. Xiao J, Shi J, Cao H, Wu S, Ren F, Xu M (2007) Analysis of binding interaction between puerarin and bovine serum albumin by multi-spectroscopic method. J Pharm Biomed Anal 45:609–615

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge the support of the National Natural Science Foundation of China (No. 21177052, 11405081), the Science and Technology Program of Hunan Province in China (2010SK3039), the Key R&D Program of Hunan Province (2018SK2029), the Fund of Hengyang Key Laboratory (No. 2018KJ110), and Research Study and Innovation Experiment Program for University Students (No.477).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Yong-Sheng Wang or Le Li.

Ethics declarations

The studies were approved by the Ethical Commission of the University of South China and were performed in accordance with ethical standards.

Conflict of interest

The author(s) declare that they have no competing interests.

Additional information

Publisher’s note

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

Jin-Hua Xue and Ling Liu are the Co-first authors.

Electronic supplementary material

ESM 1

(DOC 7780 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xue, JH., Liu, L., Wang, YS. et al. Assay of 1-hydroxypyrene via aggregation-induced quenching of the fluorescence of protamine-modified gold nanoclusters and 9-hydroxyphenanthrene-based sensitization. Microchim Acta 186, 700 (2019). https://doi.org/10.1007/s00604-019-3810-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00604-019-3810-1

Keywords

Navigation