Skip to main content
Log in

Enhancing electrochemical sensing for catechol by biomimetic oxidase covalently functionalized graphene oxide

  • Research Paper
  • Published:
Bioprocess and Biosystems Engineering Aims and scope Submit manuscript

Abstract

Catechol level is an important indicator for evaluating the quality of tea. Therefore, the exploration of a simple and efficient quantitative detection method for catechol has an important significance. In this study, functionalized graphene oxide was synthesized by chemically modifying the surface of graphene oxide. The prepared carrier was covalently combined with biomimetic oxidase iron porphyrin (FePP, the active center of horseradish peroxidase). Ionic liquid as covalent coupling agents was designed as electronic bridge between biomimetic oxidase and graphene oxide. The novel biomimetic biosensor provided a detection range of 50.0–1600.0 μmol/L by modulating under the optimal conditions of the reaction system (FePP concentration is 1.5 × 10–3 mol/L, pH 3.0, Nafion solution dosage 1% and temperature 25 °C), the detection limit is 0.09 μmol/L. The biosensor has excellent stability, repeatability and reproducibility, and is expected to be applied to the rapid detection of catechol in actual tea sample..

Graphic abstract

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Ishii T, Minoda K, Bae M-J, Mori T, Uekusa Y, Ichikawa T (2010) Binding affinity of tea catechins for HSA: characterization by high-performance affinity chromatography with immobilized albumin column. Mol Nutr Food Res 54:816–822

    Article  CAS  Google Scholar 

  2. Nsanzamahoro S, Mutuyimana FP, Han Y, Ma S, Na M, Liu J (2019) Highly selective and sensitive detection of catechol by one step synthesized highly fluorescent and water-soluble silicon nanoparticles. Sensor Actuator B Chem 281:849–856

    Article  CAS  Google Scholar 

  3. Sun X, Gong Z, Cao Y, Wang X (2013) Acetylcholinesterase biosensor based on poly (diallyldimethylammonium chloride)-multi-walled carbon nanotubes-graphene hybrid film. Nano-Micro Lett 5(1):47–56

    Article  CAS  Google Scholar 

  4. Sun X, Wang X (2010) Acetylcholinesterase biosensor based on prussian blue-modified electrode for detecting organophosphorous pesticides. Biosens Bioelectron 25(12):2611–2614

    Article  CAS  Google Scholar 

  5. Zhai C, Sun X, Zhao W, Gong Z, Wang X (2013) Acetylcholinesterase biosensor based on chitosan/prussian blue/multiwall carbon nanotubes/hollow gold nanospheres nanocomposite film by one-stepelectrodeposition. Biosens Bioelectron 42:124–130

    Article  CAS  Google Scholar 

  6. Yu S, Rao D, Sheng Q, Zheng J (2017) Simultaneous voltammetric determination of hydroquinone and catechol by using a glassy carbon electrode modified with carboxy-functionalized carbon nanotubes in a chitosan matrix and decorated with gold nanoparticles. Microchim Acta 184:3591–3601

    Article  Google Scholar 

  7. Zou B, Chu Y, Xia J (2019) Biomimetic oxidase sensor based on functionalized surface of carbon nanotubes and iron prophyrins for catechol detection. Bioproc Biosyst Eng 42:279–290

    Article  Google Scholar 

  8. Taniselass S, Arshad MKM, Gopinath SCB (2019) Graphene-based electrochemical biosensors for monitoring noncommunicable disease biomarkers. Biosens Bioelectron 130:276–292

    Article  CAS  Google Scholar 

  9. Zhang H, Zhang H, Aldalbahi A, Zuo X, Fan C, Mi X (2017) Fluorescent biosensors enabled by graphene and graphene oxide. Biosens Bioelectron 89:96–106

    Article  CAS  Google Scholar 

  10. Qi Y, Cao Y, Meng X, Cao J, Li X, Hao Q (2019) Facile synthesis of 3D sulfur/nitrogen co-doped graphene derived from graphene oxide hydrogel and the simultaneous determination of hydroquinone and catechol. Sensor Actuator B Chem 279:170–176

    Article  CAS  Google Scholar 

  11. Erogul S, Bas SZ, Ozmen M, Yildiz S (2015) A new electrochemical sensor based on Fe3O4 functionalized graphene oxide-gold nanoparticle composite film for simultaneous determination of catechol and hydroquinone. Electrochim Acta 186:302–313

    Article  CAS  Google Scholar 

  12. Bhanage BM, Gaikwad V, Saptal VB, Harada K, Sasaki T, Nishio-Hamane D (2018) Ionic liquid immobilized on graphene oxide containing palladium metal ion as an efficient catalyst for the alkoxy, amino and phenoxy carbonylation reactions. Chemnanomat 4:575–582

    Article  Google Scholar 

  13. Rothemund P, Menotti AR (2002) Porphyrin studies. vol 1 the metal complex salts of α, β, γ, δ-tetraphenylporphine. J Am Chem Soc 70:42–63

    Google Scholar 

  14. Zhang W, Zong L, Liu S, Pei S, Zhang Y, Ding X (2019) An electrochemical sensor based on electro-polymerization of caffeic acid and Zn/Ni-ZIF-8-800 on glassy carbon electrode for the sensitive detection of acetaminophen. Biosens Bioelectron 131:200–206

    Article  CAS  Google Scholar 

  15. Pillai KC, Chung SJ, Moon I-S (2008) Studies on electrochemical recovery of silver from simulated waste water from Ag(II)/Ag(I) based mediated electrochemical oxidation process. Chemosphere 73:1505–1511

    Article  CAS  Google Scholar 

  16. Wang Y, Yang J, Sun S, Wang L, Guo T, Zhang D (2019) PtNi nanoparticles supported on electrochemically reduced porous graphene oxide for methanol oxidation reaction. Chem Phys Lett 730:575–581

    Article  CAS  Google Scholar 

  17. Khalili Dermani A, Kowsari E, Ramezanzadeh B, Amini R (2019) Utilizing imidazole based ionic liquid as an environmentally friendly process for enhancement of the epoxy coating/graphene oxide composite corrosion resistance. J Ind Eng Chem 79:353–363

    Article  CAS  Google Scholar 

  18. Mejias Carpio IE, Mangadlao JD, Nguyen HN, Advincula RC, Rodrigues DF (2014) Graphene oxide functionalized with ethylenediamine triacetic acid for heavy metal adsorption and anti-microbial applications. Carbon 77:289–301

    Article  CAS  Google Scholar 

  19. Lan D-H, Chen L, Au C-T, Yin S-F (2015) One-pot synthesized multi-functional graphene oxide as a water-tolerant and efficient metal-free heterogeneous catalyst for cycloaddition reaction. Carbon 93:22–31

    Article  CAS  Google Scholar 

  20. Castro KADF, Figueira F, Mendes RF, Almeida Paz FA, Neves MDGPMS, Cavaleiro JAS (2019) Porphyrinic coordination polymer-type materials as heterogeneous catalysts in catechol oxidation. Polyhedron 158:478–484

    Article  CAS  Google Scholar 

  21. Surekha G, Krishnaiah K, Ravi N, Suvarna R (2020) FTIR, Raman and XRD analysis of graphene oxide films prepared by modified Hummers method. J Phys Conf Ser 1945:19–21

    Google Scholar 

  22. Zou B, Wang P, Liu Z, Xia J, Chen B, Tan Z (2019) Biomimetic oxidase based on functionalized mesoporous SiO2 and metalloporphyrin for 5-hydroxymethylfurfural conversion. Process Biochem 86:65–72

    Article  CAS  Google Scholar 

  23. Gan T, Wang Z, Shi Z, Zheng D, Sun J, Liu Y (2018) Graphene oxide reinforced core-shell structured Ag@Cu2O with tunable hierarchical morphologies and their morphology-dependent electrocatalytic properties for bio-sensing applications. Biosens Bioelectron 112:23–30

    Article  CAS  Google Scholar 

  24. Brogan APS, Hallett JP (2016) Solubilizing and stabilizing proteins in anhydrous ionic liquids through formation of protein-polymer surfactant nanoconstructs. J Am Chem Soc 138:4494–4501

    Article  CAS  Google Scholar 

  25. Casero E, Parra-Alfambra AM, Petit-Domínguez MD, Pariente F, Lorenzo E, Alonso C (2012) Differentiation between graphene oxide and reduced graphene by electrochemical impedance spectroscopy. Electrochem Commun 20:63–66

    Article  CAS  Google Scholar 

  26. Li S, Zhang Q, Lu Y, Ji D, Zhang D, Wu J (2017) One step electrochemical deposition and reduction of graphene oxide on screen printed electrodes for impedance detection of glucose. Sensor Actuator B Chem 244:290–298

    Article  CAS  Google Scholar 

  27. Numviyimana C, Chmiel T, Kot-Wasik A, Namieśnik J (2019) Study of pH and temperature effect on lipophilicity of catechol-containing antioxidants by reversed phase liquid chromatography. Microchem J 145:380–387

    Article  CAS  Google Scholar 

  28. Guo W, Pi F, Zhang H, Sun J, Zhang Y, Sun X (2017) A novel molecularly imprinted electrochemical sensor modified with carbon dots, chitosan, gold nanoparticles for the determination of patulin. Biosens Bioelectron 98:299–304

    Article  CAS  Google Scholar 

  29. Madhu R, Palanisamy S, Chen S-M, Piraman S (2014) A low temperature synthesis of activated carbon from the bio waste for simultaneous electrochemical determination of hydroquinone and catechol. J Electroanal Chem 727:84–90

    Article  CAS  Google Scholar 

  30. Nazari M, Kashanian S, Moradipour P, Maleki N (2018) A novel fabrication of sensor using ZnO-Al2O3 ceramic nanofifibers to simultaneously detect catechol and hydroquinone. J Electroanal Chem 812:122–131

    Article  CAS  Google Scholar 

  31. Zheng X, Hu Y, Li H, Han B, Lin R, Huang B (2020) N-doped carbon nanotube frameworks modified electrode for the selective sensing of hydroquinone and catechol. J Electroanal Chem 861:113968–113976

    Article  CAS  Google Scholar 

  32. Nazari M, Kashanian S, Maleki N, Shahabadi N (2019) Laccase immobilized onto graphene oxide nanosheets and electrodeposited gold-cetyltrimethylammonium bromide complex to fabricate a novel catechol biosensor. Bull Mater Sci 42:42–51

    Article  Google Scholar 

  33. Abdul Rasol Albayati S, Kashanian S, Nazari M, Rezaei S (2019) Novel fabrication of a laccase biosensor to detect phenolic compounds using a carboxylated multiwalled carbon nanotube on the electropolymerized support. Bull Mater Sci 42:187–192

    Article  Google Scholar 

  34. Sunil Kumar Naik T, Kumara Swamy B (2017) Modification of carbon paste electrode by electrochemical polymerization of neutral red and its catalytic capability towards the simultaneous determination of catechol and hydroquinone: a voltammetric study. J Electroanal Chem 804:78–86

    Article  CAS  Google Scholar 

  35. Bin Z, Yanhong C, Jiaojiao X (2019) Biomimetic oxidase sensor based on functionalized surface of carbon nanotubes and iron prophyrins for catechol detection. Bioprocess Biosyst Eng 42(2):279–290

    Article  CAS  Google Scholar 

  36. Bagheri N, Khataee A, Habibi B, Hassanzadeh J (2018) Mimetic Ag nanoparticle/Zn-based MOF nanocomposite (AgNPs@ZnMOF) capped with molecularly imprinted polymer for the selective detection of patulin. Talanta 179:710–718

    Article  CAS  Google Scholar 

  37. Ye Y, Yan W, Liu Y, He S, Cao X, Xu X (2019) Electrochemical detection of Salmonella using an invA genosensor on polypyrrole-reduced graphene oxide modified glassy carbon electrode and AuNPs-horseradish peroxidase-streptavidin as nanotag. Anal Chim Acta 1074:80–88

    Article  CAS  Google Scholar 

  38. Feizabadi M, Soleymanpour A, Faridnouri H, Ajloo D (2019) Improving stability of biosensor based on covalent immobilization of horseradish peroxidase by γ-aminobutyric acid and application in detection of H2O2. Int J Biol Macromol 136:597–606

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The work was funded by the National Natural Science Foundation of China (No. 21406093), the Natural Science Foundation of Jiangsu province (BK20140529), the Open Project Program of State Key Laboratory of Food Science and Technology of Jiangnan University (SKLF-KF-201919), Key University Science Research Project of Jiangsu Province (14KJB530001), China Postdoctoral Science Foundation (2014M550271), and Priority Academic Program Development of Jiangsu Higher Education Institutions.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zou Bin.

Ethics declarations

Conflict of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Publisher's Note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jiaojiao, X., Pengyun, W., Bin, Z. et al. Enhancing electrochemical sensing for catechol by biomimetic oxidase covalently functionalized graphene oxide. Bioprocess Biosyst Eng 44, 343–353 (2021). https://doi.org/10.1007/s00449-020-02446-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00449-020-02446-x

Keywords

Navigation