Skip to main content
SpringerLink
Log in

Biomimetic oxidase sensor based on functionalized surface of carbon nanotubes and iron prophyrins for catechol detection

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

Abstract

A novel and highly stable biomimetic oxidase sensor system was designed for catehol detection. FePP used as biomimetic horseradish peroxidase (HRP) was immobilized onto modified multi-walled carbon nanotubes (MWCNTs). Functional groups such as –OH, –NH2 and –COOH were introduced onto the surface of MWCNTs to provide biomimetic microenvironment for iron porphyrins (FePP). Stable biomimetic enzyme electrode has been developed to detect catechol as a simple, economical and efficient method. At optimal condition, the detection limit of OH-MWCNTs/FePP/Nafion was 3.754 × 10− 6 M. After stored at − 4 °C for 35 days, the oxidation current value still maintained 98.3% of initial activity. In repetitive nature test, relative standard deviation (RSD) of oxidation current remained within 1.0% after ten consecutive measurements in the same concentration of catechol solution, while most of reported oxidase sensor was within 2.0% under the same condition.

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

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

Similar content being viewed by others

References

  1. Miled H, Saada M, Jallali I, Tlili Z (2017) Variability of antioxidant and biological activities of Rhus tripartitum related to phenolic compounds. Excli J 16:439–447

    PubMed  PubMed Central  Google Scholar 

  2. Bao G, Barasch J, Xu J, Wang W, Hu F, Deng S (2015) Purification and structural characterization of “simple catechol”, the NGAL-siderocalin siderophore in human urine. Rsc Adv 36:27–28535

    Google Scholar 

  3. Goulart L, Mascaro L (2016) GC electrode modified with carbon nanotubes and NiO for the simultaneous determination of bisphenol A, hydroquinone and catechol. Electrochim Acta 196:48–55

    Article  CAS  Google Scholar 

  4. M’Hemdi A, Dbira B, Abdelhed R, Brillas E, Ammar S (2012) Mineralization of catechol by fenton and photo-fenton processes. Acta Hydrochim Hydrobiol 40:878–885

    Google Scholar 

  5. Vatsal A, Zinjarde S, Ravikumar A (2017) Phenol is the initial product formed during growth and degradation of bromobenzene by tropical marine yeast, Yarrowia lipolytica NCIM 3589 via an early dehalogenation step. Front Microbiol 8:1165–1168

    Article  PubMed  PubMed Central  Google Scholar 

  6. Zhou Y, Tang L, Zeng G, Chen J, Wang J, Fan C (2015) Amplified and selective detection of manganese peroxidase genes based on enzyme-scaffolded-gold nanoclusters and mesoporous carbon nitride. Biosens Bioelectron 65:382–389

    Article  CAS  PubMed  Google Scholar 

  7. Pang Y, Zeng G, Lin T, Yi Z, Zhen L, Chen L (2011) Laccase biosensor using magnetic multiwalled carbon nanotubes and chitosan/silica hybrid membrane modified magnetic carbon paste electrode. J Cent South Univ T 18:1849–1856

    Article  CAS  Google Scholar 

  8. Neta P (2002) Redox reactions of metalloporphyrins and their role in catalyzed reduction of carbon dioxide. Office Sci Tech Inf Tech Rep 208:1274–1290

    Google Scholar 

  9. Günay T, Çimen Y (2017) Degradation of 2,4,6-trichlorophenol with peroxymonosulfate catalyzed by soluble and supported iron porphyrins. Environ Pollu 231:1013–1020

    Article  CAS  Google Scholar 

  10. Jiao Y, Jia H, Guo Y, Zhang H, Wang Z, Sun X (2016) An ultrasensitive aptasensor for chlorpyrifos based on ordered mesoporous carbon/ferrocene hybrid multiwalled carbon nanotubes. Rsc Advances 6:63–70

    Google Scholar 

  11. 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  PubMed  Google Scholar 

  12. Sun X, Li F, Shen G, Huang J, Wang X (2013) Aptasensor based on the synergistic contributions of chitosan-gold nanoparticles, graphene-gold nanoparticles and multi-walled carbon nanotubes-cobalt phthalocyanine nanocomposites for kanamycin detection. Analyst 139:299–308

    Article  PubMed  Google Scholar 

  13. Wu J (2017) Preparation of Ni(OH)2/MWCNTs composite for supercapacitor application. Int J Electrochem Sci 42:9665–9674

    Article  CAS  Google Scholar 

  14. Wang Z, Duan L, Zhu D, Chen W (2014) Effects of Cu(II) and Ni(II) ions on adsorption of tetracycline to functionalized carbon nanotubes. J Zhejiang Uni Sci-A 15:653–661

    Article  CAS  Google Scholar 

  15. Ji P, Tan H, Xu X (2010) Lipase covalently attached to multiwalled carbon nanotubes as an efficient catalyst in organic solvent. Aiche J 56:3005–3011

    Article  CAS  Google Scholar 

  16. Tay W, Epperson J, Da S, Ming L (2010) 1H NMR, mechanism, and mononuclear oxidative activity of the antibiotic metallopeptide bacitracin: the role of D-Glu-4, interaction with pyrophosphate moiety, DNA binding and cleavage, and bioactivity. J Am Chem Soc 132:5652–5660

    Article  CAS  PubMed  Google Scholar 

  17. Maleki N, Kashanian S, Maleki E, Nazari M (2017) A novel enzyme based biosensor for catechol detection in water samples using artificial Neural network. Biochem Eng J 128:1–11

    Article  CAS  Google Scholar 

  18. Vlamidis Y, Gualandi I, Tonelli D (2017) Amperometric biosensors based on reduced GO and MWCNTs composite for polyphenols detection in fruit juices. J Electroanal Chem 32:285–292

    Article  CAS  Google Scholar 

  19. Li N, Wang Y, Wu C, Lu W, Pei K, Chen W (2017) Bioinspired catalytic generation of high-valent cobalt-oxo species by the axially coordinated CoPc on Pyridine-functionalized MWCNTs for the elimination of organic contaminants. Appl Surf Sci 28:1112–1121

    Google Scholar 

  20. Ganewatta N, El Z (2017) Monolithic capillary columns consisting of poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate) and their diol derivatives with incorporated hydroxyl functionalized multiwalled carbon nanotubes for reversed-phase capillary electrochromatography. Analyst 66:270–279

    Google Scholar 

  21. Huang J, Zhao L, Lei W, Wen W, Wang Y, Bao T (2017) A high-sensitivity electrochemical aptasensor of carcinoembryonic antigen based on graphene quantum dots-ionic liquid-nafion nanomatrix and DNAzyme-assisted signal amplification strategy. Biosens Bioelectron 99:28–33

    Article  CAS  PubMed  Google Scholar 

  22. Abatti G, Pires A, Spinelli A, Scharnagl N, Conceição T (2017) Conversion coating on magnesium alloy sheet (AZ31) by vanillic acid treatment: preparation, characterization and corrosion behavior. J Alloys Compd 38:224–232

    Google Scholar 

  23. Vajda K, Mogyorosi K, Nemeth Z, Hernadi K, Forro L, Magrez A (2011) Photocatalytic activity of TiO2/SWCNT and TiO2/MWCNT nanocomposites with different carbon nanotube content. Phys Status Solidi 248:2496–2499

    Article  CAS  Google Scholar 

  24. Hajian R, Ehsanikhah A (2017) Manganese Porphyrin immobilized on magnetic MCM-41 nanoparticles as an efficient and reusable catalyst for alkene oxidations with sodium periodate. Chem Phys Lett 691:146–154

    Article  CAS  Google Scholar 

  25. Iacovita C, Stiufiuc R, Radu T, Florea A, Stiufiuc G, Dutu A (2015) Polyethylene glycol-mediated synthesis of cubic iron oxide nanoparticles with high heating power. Nano Res Lett 10:391–397

    Article  CAS  Google Scholar 

  26. Liao N, Jia D, Yang Z, Zhou Y, Li Y, Jia X (2017) Strengthening and toughening effects of MWCN Ts on Si2BC3N ceramics sintered by SPS technique. Mat Sci Eng A 97:710–717

    Google Scholar 

  27. Nikoofard H, Solbi M (2016) Electro-catalytic Oxidation of catechol at Poly(1-amino-9,10-anthraquinone)-SDS composite film. Acta Chim Slov 63:705–712

    Article  CAS  PubMed  Google Scholar 

  28. Martins L, Souza E, Fernandez T, Souza B, Rachinski S, Pinheiro C (2010) Binuclear CuII complexes as catalysts for hydrocarbon and catechol oxidation reactions with hydrogen peroxide and molecular oxygen. J Brazil Chem Soc 21:1218–1229

    Article  CAS  Google Scholar 

  29. Pouliot M, Renaud P, Schenk K, Studer A, Vogler T (2009) Oxidation of catecholboron enolates with TEMPO. Angew Chem Inter Edit 48:6037–6040

    Article  CAS  Google Scholar 

  30. Blake D, Maness P, Huang Z, Wolfrum E, Huang J, Jacoby W (1999) Application of the photocatalytic chemistry of titanium dioxide to disinfection and the killing of cancer cells. Sep Puri Methods 28:1–50

    Article  CAS  Google Scholar 

  31. Kubesch K, Zona R, Solar S, Gehringer P (2005) Degradation of catechol by ionizing radiation, ozone and the combined process ozone-electron-beam. Radiat Phys Chem 72:447–453

    Article  CAS  Google Scholar 

  32. Mossanha R, Erdmann C, Santos C, Wohnrath K, Fujiwara S, Pessoa C (2017) Construction of a biosensor based on SAM of thiolactic acid on gold nanoparticles stabilized by silsesquioxane polyelectrolyte for cathecol determination. Sensor Actuat B Chem 46:747–756

    Article  CAS  Google Scholar 

  33. Dong W, Han J, Shi J (2017) Amperometric biosensor for detection of phenolic compounds based on tyrosinase, N-acetyl-l-cysteine-capped gold nanoparticles and chitosan nanocomposite. Chin J Chem 35:1305–1310

    Article  CAS  Google Scholar 

  34. Oliveira T, Barroso M, Morais S, Araújo M, Freire C, De L (2014) Sensitive bi-enzymatic biosensor based on polyphenoloxidases-gold nanoparticles-chitosan hybrid film-graphene doped carbon paste electrode for carbamates detection. Bioelectrochemistry 98:20–29

    Article  CAS  PubMed  Google Scholar 

  35. Ribeiro F, Maria Fátima B, Simone M, Subramanian V, Pedro L, Correia A (2014) Simple laccase-based biosensor for formetanate hydrochloride quantification in fruits. Bioelectrochemistry 95:7–14

    Article  CAS  PubMed  Google Scholar 

  36. Gopal P, Reddy T, Nagaraju C, Narasimha G (2014) Preparation, characterization and analytical application of an electrochemical laccase biosensor towards low level determination of isoprenaline in human serum samples. RSC Adv 4:64214–64214

    Article  CAS  Google Scholar 

  37. Amatatongchai M, Sroysee W, Laosing S, Chairam S (2013) Rapid screening method for assessing total phenolic content using simple flow injection system with laccase based-biosensor. Int J Electrochem Sc 8:10526–10539

    CAS  Google Scholar 

  38. Elkaoutit M, Naranjo-Rodriguez I, Temsamani K, Vega M (2007) Dual laccase–tyrosinase based sonogel-carbon biosensor for monitoring polyphenols in beers. J Agric Food Chem 55:8011–8018

    Article  CAS  PubMed  Google Scholar 

  39. Abdullah J, Ahmad M, Heng L, Karuppiah N, Sidek H (2007) An optical biosensor based on immobilization of laccase and MBTH in stacked films for the detection of catechol. Sensors 7:2238–2250

    Article  CAS  PubMed  Google Scholar 

  40. Pérez López B, Merkoçi A (2009) Improvement of the electrochemical detection of catechol by the use of a carbon nanotube based biosensor. Analyst 13:460–13464

    Google Scholar 

  41. Chung M, Nguyen T, Tran T, Yoon H, Kim I, Kim M (2017) Ultrarapid sonochemical synthesis of enzyme-incorporated copper nanoflowers and their application to mediatorless glucose biofuel cell. Appl Surf Sci 45:203–209

    Google Scholar 

  42. Yang J, Li D, Pang Z, Yang J, Li D, Pang Z, Wei Q (2016) Laccase biosensor based on Ag-doped TiO2 nanoparticles on CuCNFs for the determination of hydroquinone. Nano 11:597–600

    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), Key University Science Research Project of Jiangsu Province (14KJB530001), China Postdoctoral Science Foundation (2014M550271), and the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.

Author information

Authors and Affiliations

  1. School of Food and Biological Engineering, Jiangsu University, No. 301 Xuefu Road, Zhenjiang, 212013, China

    Zou Bin, Chu Yanhong & Xia Jiaojiao

Authors
  1. Zou Bin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chu Yanhong
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xia Jiaojiao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Zou Bin or Xia Jiaojiao.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bin, Z., Yanhong, C. & Jiaojiao, X. Biomimetic oxidase sensor based on functionalized surface of carbon nanotubes and iron prophyrins for catechol detection. Bioprocess Biosyst Eng 42, 279–290 (2019). https://doi.org/10.1007/s00449-018-2032-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00449-018-2032-y

Keywords

Search

Navigation