Abstract
An optical bio-probe based on the immobilized tyrosinase on the surface of Fe3O4@Au was described for the detection of dopamine, phenol and catechol. The prepared bio-probe (Fe3O4@Au@tyrosinase) was characterized by means such as TEM, SEM, VSM, DLS and TGA. In the presence of the bio-probe, the phenol, catechol and dopamine were converted to benzoquinone, o-quinone and dopaquinone, and the fluorescence spectra appeared at 308 nm, 329 nm and 336 nm with ex = 270 nm, respectively. However, by increasing the concentration of phenolic compounds in the bio-probe, the amount of products (benzoquinone, o-quinone and dopaquinone) was increased which was the reason for the increase in fluorescence intensity. Using this mechanism, a bio-probe was designed such that the intensity of the fluorescence spectra increased proportionally with the increase of the substrate concentrations after different time periods. The 0.003 mg/mL of tyrosinase was loaded on 1.65 mg/mL of the Fe3O4@Au. The highest performance for a bio-probe was demonstrated at room temperature and pH 6.8. By investigating the characteristics of the response of the bio-probe to different phenolic compounds, it was found that the bio-probe had a linear response in the concentration range 5.0–75.0 µM, 10.0–100.0 µM for phenol and dopamine and 50.0–500.0 M for catechol. The Michaelis–Menten constant (Km) of the bio-probe was calculated as 0.6 µM. Finally, the bio-probe seems to be stable and efficient even after about 2 months.
Graphic abstract
A novel and easy method for the detection of dopamine, phenol and catechol by florescence that uses oxide capability to identify the phenolic compounds was introduced.
Similar content being viewed by others
Change history
16 August 2019
In the original article, the third author’s name and affiliation is incorrectly published.
References
Liggett SB (2000) Pharmacogenetics of beta-1-and beta-2-adrenergic receptors. Pharmacology 61(3):167
Jaber M, Robinson SW, Missale C, Caron MG (1996) Dopamine receptors and brain function. Neuropharmacology 35(11):1503–1519
Ali SR, Ma Y, Parajuli RR, Balogun Y, Lai WY-C, He H (2007) A nonoxidative sensor based on a self-doped polyaniline/carbon nanotube composite for sensitive and selective detection of the neurotransmitter dopamine. Anal Chem 79(6):2583–2587
Ankireddy SR, Kim J (2015) Selective detection of dopamine in the presence of ascorbic acid via fluorescence quenching of InP/ZnS quantum dots. Int J Nanomed 10(1):113
He Y-S, Pan C-G, Cao H-X, Yue M-Z, Wang L, Liang G-X (2018) Highly sensitive and selective dual-emission ratiometric fluorescence detection of dopamine based on carbon dots-gold nanoclusters hybrid. Sens Actuators B Chem 265:371–377
Freire RS, Durán N, Kubota LT (2002) Electrochemical biosensor-based devices for continuous phenols monitoring in environmental matrices. J Braz Chem Soc 13(4):456–462
Leboukh S, Gouzi H, Coradin T, Yahia H (2018) An optical catechol biosensor based on a desert truffle tyrosinase extract immobilized into a sol–gel silica layered matrix. J Sol-Gel Sci Technol 86(3):675–681
Gupta VK, Karimi-Maleh H, Sadegh R (2015) Simultaneous determination of hydroxylamine, phenol and sulfite in water and waste water samples using a voltammetric nanosensor. Int J Electrochem Sci 10:303–316
Huang J, Wang X, Jin Q, Liu Y, Wang Y (2007) Removal of phenol from aqueous solution by adsorption onto OTMAC-modified attapulgite. J Environ Manag 84(2):229–236
Contreras EM, Albertario ME, Bertola NC, Zaritzky NE (2008) Modelling phenol biodegradation by activated sludges evaluated through respirometric techniques. J Hazard Mater 158(2–3):366–374
Busca G, Berardinelli S, Resini C, Arrighi L (2008) Technologies for the removal of phenol from fluid streams: a short review of recent developments. J Hazard Mater 160(2–3):265–288
Wei G, Yu J, Zhu Y, Chen W, Wang L (2008) Characterization of phenol degradation by Rhizobium sp. CCNWTB 701 isolated from Astragalus chrysopteru in mining tailing region. J Hazard Mater 151(1):111–117
Senturk HB, Ozdes D, Gundogdu A, Duran C, Soylak M (2009) Removal of phenol from aqueous solutions by adsorption onto organomodified Tirebolu bentonite: equilibrium, kinetic and thermodynamic study. J Hazard Mater 172(1):353–362
dos Santos VL, de Souza Monteiro A, Braga DT, Santoro MM (2009) Phenol degradation by Aureobasidium pullulans FE13 isolated from industrial effluents. J Hazard Mater 161(2–3):1413–1420
van de Merbel NC, Hendriks G, Imbos R, Tuunainen J, Rouru J, Nikkanen H (2011) Quantitative determination of free and total dopamine in human plasma by LC–MS/MS: the importance of sample preparation. Bioanalysis 3(17):1949–1961
Perry M, Li Q, Kennedy RT (2009) Review of recent advances in analytical techniques for the determination of neurotransmitters. Anal Chim Acta 653(1):1–22
Mao Y, Bao Y, Gan S, Li F, Niu L (2011) Electrochemical sensor for dopamine based on a novel graphene-molecular imprinted polymers composite recognition element. Biosens Bioelectron 28(1):291–297
Wang C, Wu C, Zhang L, Zhang J (2016) Ultraperformance liquid chromatography–tandem mass spectrometry method for profiling ketolic and phenolic sex steroids using an automated injection program combined with diverter valve switch and step analysis. Anal Chem 88(16):7878–7884
Quynh BTP, Byun JY, Kim SH (2015) Non-enzymatic amperometric detection of phenol and catechol using nanoporous gold. Sens Actuators B Chem 221:191–200
Gupta VK, Mergu N, Kumawat LK, Singh AK (2015) Selective naked-eye detection of magnesium (II) ions using a coumarin-derived fluorescent probe. Sens Actuators B Chem 207:216–223
Gupta VK, Mergu N, Kumawat LK, Singh AK (2015) A reversible fluorescence “off–on–off” sensor for sequential detection of aluminum and acetate/fluoride ions. Talanta 144:80–89
Yola ML, Gupta VK, Eren T, Şen AE, Atar N (2014) A novel electro analytical nanosensor based on graphene oxide/silver nanoparticles for simultaneous determination of quercetin and morin. Electrochim Acta 120:204–211
Gupta VK, Singh AK, Kumawat LK (2014) Thiazole Schiff base turn-on fluorescent chemosensor for Al3 + ion. Sens Actuators B Chem 195:98–108
Xing Y, Jin Y-Y, Si J-C, Peng M-L, Wang X-F, Chen C, Cui Y-L (2015) Controllable synthesis and characterization of Fe3O4/Au composite nanoparticles. J Magn Magn Mater 380:150–156
Zhang T, Wang W, Zhang D, Zhang X, Ma Y, Zhou Y, Qi L (2010) Biotemplated synthesis of gold nanoparticle–bacteria cellulose nanofiber nanocomposites and their application in biosensing. Adv Funct Mater 20(7):1152–1160
Lai G-S, Zhang H-L, Han D-Y (2009) Amperometric hydrogen peroxide biosensor based on the immobilization of horseradish peroxidase by carbon-coated iron nanoparticles in combination with chitosan and cross-linking of glutaraldehyde. Microchim Acta 165(1–2):159–165
Guo S, Li D, Zhang L, Li J, Wang E (2009) Monodisperse mesoporous superparamagnetic single-crystal magnetite nanoparticles for drug delivery. Biomaterials 30(10):1881–1889
Pham TTH, Cao C, Sim SJ (2008) Application of citrate-stabilized gold-coated ferric oxide composite nanoparticles for biological separations. J Magn Magn Mater 320(15):2049–2055
Kim J, Park S, Lee JE, Jin SM, Lee JH, Lee IS, Yang I, Kim JS, Kim SK, Cho MH (2006) Designed fabrication of multifunctional magnetic gold nanoshells and their application to magnetic resonance imaging and photothermal therapy. Angew Chem 118(46):7918–7922
Baby TT, Ramaprabhu S (2010) SiO2 coated Fe3O4 magnetic nanoparticle dispersed multiwalled carbon nanotubes based amperometric glucose biosensor. Talanta 80(5):2016–2022
Grabar KC, Freeman RG, Hommer MB, Natan MJ (1995) Preparation and characterization of Au colloid monolayers. Anal Chem 67(4):735–743
Dehghani MH, Sanaei D, Ali I, Bhatnagar A (2016) Removal of chromium (VI) from aqueous solution using treated waste newspaper as a low-cost adsorbent: kinetic modeling and isotherm studies. J Mol Liq 215:671–679
Karimi-Maleh H, Tahernejad-Javazmi F, Atar N, Yola ML, Gupta VK, Ensafi AA (2015) A novel DNA biosensor based on a pencil graphite electrode modified with polypyrrole/functionalized multiwalled carbon nanotubes for determination of 6-mercaptopurine anticancer drug. Ind Eng Chem Res 54(14):3634–3639
Asfaram A, Ghaedi M, Agarwal S, Tyagi I, Gupta VK (2015) Removal of basic dye Auramine-O by ZnS: Cu nanoparticles loaded on activated carbon: optimization of parameters using response surface methodology with central composite design. RSC Adv 5(24):18438–18450
Gupta KV, Nayak A, Agarwal S, Singhal B (2011) Recent advances on potentiometric membrane sensors for pharmaceutical analysis. Comb Chem High Throughput Screening 14(4):284–302
Vinod K (1995) Determination of lead using a poly (vinyl chloride)-based crown ether membrane. Analyst 120(2):495–498
Jain AK, Gupta VK, Sahoo BB, Singh LP (1995) Copper (II)-selective electrodes based on macrocyclic compounds. Analytical proceedings including analytical communications, vol 3. Royal Society of Chemistry, UK, pp 99–101
Yang L, Xiong H, Zhang X, Wang S (2012) A novel tyrosinase biosensor based on chitosan-carbon-coated nickel nanocomposite film. Bioelectrochemistry 84:44–48
Quan D, Kim Y, Shin W (2004) Characterization of an amperometric laccase electrode covalently immobilized on platinum surface. J Electroanal Chem 561:181–189
Kafi A, Chen A (2009) A novel amperometric biosensor for the detection of nitrophenol. Talanta 79(1):97–102
Chen X, Cheng G, Dong S (2001) Amperometric tyrosinase biosensor based on a sol–gel-derived titanium oxide–copolymer composite matrix for detection of phenolic compounds. Analyst 126(10):1728–1732
Abdullah J, Ahmad M, Karuppiah N, Heng LY, Sidek H (2006) Immobilization of tyrosinase in chitosan film for an optical detection of phenol. Sens Actuators B Chem 114(2):604–609
Wang J, Fang L, Lopez D (1994) Amperometric biosensor for phenols based on a tyrosinase–graphite–epoxy biocomposite. Analyst 119(3):455–458
Hall GF, Best DJ, Turner AP (1988) Amperometric enzyme electrode for the determination of phenols in chloroform. Enzym Microb Technol 10(9):543–546
Cosnier S, Innocent C (1993) A new strategy for the construction of a tyrosinase-based amperometric phenol and o-diphenol sensor. Bioelectrochem Bioenerg 31(2):147–160
Önnerfjord P, Emnéus J, Marko-Varga G, Gorton L, Ortega F, Domínguez E (1995) Tyrosinase graphite-epoxy based composite electrodes for detection of phenols. Biosens Bioelectron 10(6–7):607–619
Karami C, Taher MA (2019) A catechol biosensor based on immobilizing laccase to Fe3O4@ Au core-shell nanoparticles. Int J Biol Macromol 129:84–90
Karagoz B, Bayramoglu G, Altintas B, Bicak N, Arica MY (2011) Amine functional monodisperse microbeads via precipitation polymerization of N-vinyl formamide: immobilized laccase for benzidine based dyes degradation. Bioresour Technol 102(13):6783–6790
Xie J, Xu C, Kohler N, Hou Y, Sun S (2007) Controlled PEGylation of monodisperse Fe3O4 nanoparticles for reduced non-specific uptake by macrophage cells. Adv Mater 19(20):3163–3166
Park S-A, Jang E, Koh W-G, Kim B (2010) Fabrication and characterization of optical biosensors using polymer hydrogel microparticles and enzyme–quantum dot conjugates. Sens Actuators B Chem 150(1):120–125
Chai L, Zhou J, Feng H, Tang C, Huang Y, Qian Z (2015) Functionalized carbon quantum dots with dopamine for tyrosinase activity monitoring and inhibitor screening: in vitro and intracellular investigation. ACS Appl Mater Interfaces 7(42):23564–23574
Acknowledgements
The authors gratefully acknowledge the Research Council of Kermanshah University of Medical Sciences (Grant number: 97708) for the financial support.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Arkan, E., Karami, C. & Rafipur, R. Immobilization of tyrosinase on Fe3o4@Au core–shell nanoparticles as bio-probe for detection of dopamine, phenol and catechol. J Biol Inorg Chem 24, 961–969 (2019). https://doi.org/10.1007/s00775-019-01691-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00775-019-01691-0