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Microchimica Acta

, Volume 183, Issue 3, pp 1137–1144 | Cite as

Indirect amperometric sensing of dopamine using a redox-switchable naphthoquinone-terminated self-assembled monolayer on gold electrode

  • Asma Hammami
  • Rihab Sahli
  • Noureddine RaouafiEmail author
Original Paper

Abstract

We report on the design of a simple yet sensitive and selective electrode for amperometric determination of dopamine at a cathodic potential as low as −0.30 V vs. Ag/AgCl. The electrode was obtained by self-assembly of ω-mercaptopropyl naphthoquinone (NQ-SAM) on the surface of a polycrystalline gold electrode. The presence of dopamine induces an increase of the reduction current peak at −0.30 V corresponding to the reduction of naphthoquinone to hydronaphthoquinone. Dopamine and dopamine-quinone accumulate on the surface to form a 3D network linked by hydrogen bonds. Raman and infrared spectroscopy as well as atomic force microscopy confirmed the multilayer formation. The method allows dopamine to be indirectly detected at a working potential that is lower by 0.50 V than the standard oxidation potential at a bare gold electrode. The sensor shows distinct oxidation potentials for dopamine (120 mV), ascorbic acid (280 mV) and uric acid (520 mV) which makes the method fairly selective. The analytical range extends from 1 to 100 μM concentrations of dopamine, and the limits of detection and quantification are 0.040 and 0.134 μM, respectively.

Graphical abstract

The self-assembly of naphthoquinone-terminated alkylthiol on gold electrode yields a sensitive sensor for dopamine detection at −0.30 V vs. Ag/AgCl, which is 0.5 V lower than the dopamine standard redox potential. It is able to discriminate dopamine in presence of interferents.

Keywords

Electroactive SAM Atomic force microscopy Cyclic voltammetry Dopamine Electron transfer Impedance 

Notes

Acknowledgments

Authors wish to acknowledge the financial support from the Tunisian Ministry of Higher Education and Scientific Research for support to this work through the mobility grant “Bourse d’Alternance” awarded to A. Hammami. Thanks also go to the Prof K. Boujlel for helpful discussions and comments and Mr. Ghazi Jomaa (INRAP, Tunis, Tunisia) for the acquisition of the AFM images. We also acknowledge the help of Dr. Adel Moadhen form the laboratory “Nanomatériaux et Photonique” for the Raman spectroscopy facility and recording of the Raman spectra.

Compliance with ethical standards

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

Supplementary material

604_2015_1739_MOESM1_ESM.docx (1.8 mb)
ESM 1 (DOCX 1.80 mb)

References

  1. 1.
    Huang Q, Zhang H, Hua S, Li F, Weng W, Chen J, Wang Q, He Y, Zhang W, Bao X (2014) A sensitive and reliable dopamine bio sensor was developed based on the Au@carbon dots–chitosan composite film. Biosens Bioelectron 52:277–280CrossRefGoogle Scholar
  2. 2.
    Wightman RM, May LJ, Michael AC (1988) Detection of dopamine dynamics in the brain. Anal Chem 60:769A–779ACrossRefGoogle Scholar
  3. 3.
    Hollenbach E, Schulz C, Lehnert H (1998) Rapid and sensitive determination of catecholamines and the metabolite 3-methoxy-4-hydroxyphen-ethyleneglycol using HPLC following novel extraction procedures. Life Sci 63:737–750CrossRefGoogle Scholar
  4. 4.
    Yang X, Feng B, He X, Li F, Ding Y, Fei J (2013) Carbon nanomaterial based electrochemical sensors for biogenic amines. Microchim Acta 180:935–956CrossRefGoogle Scholar
  5. 5.
    Capella P, Ghasemzadeh B, Mitchell K, Adams RN (1990) Nafion-coated fiber electrodes for neurochemical studies in brain tissue. Electroanalysis 2:175–182CrossRefGoogle Scholar
  6. 6.
    Wang C, Xu P, Zhuo K (2014) Ionic liquid functionalized graphene-based electrochemical biosensor for simultaneous determination of dopamine and uric acid in the presence of ascorbic acid. Electroanalysis 26:191–198CrossRefGoogle Scholar
  7. 7.
    Goyal RN, Gupta VK, Bachheti N, Sharma RA (2008) Electrochemical sensor for the determination of dopamine in presence of high concentration of ascorbic acid using a fullerene-C60 coated gold electrode. Electroanalysis 20:757–764CrossRefGoogle Scholar
  8. 8.
    Deng C, Chen J, Wang M, Xiao C, Nie Z, Yao SH (2009) A novel and simple strategy for selective and sensitive determination of dopamine based on the boron-doped carbon nanotubes modified electrode. Biosens Bioelectron 24:2091–2094CrossRefGoogle Scholar
  9. 9.
    Min K, Yoo YJ (2009) Amperometric detection of dopamine based on tyrosinase–SWNTs–ppy composite electrode. Talanta 80:1007–1011CrossRefGoogle Scholar
  10. 10.
    Wang J (1999) Amperometric biosensors for clinical and therapeutic drug monitoring: a review. J Pharmaceut Biomed Anal 19:47–53CrossRefGoogle Scholar
  11. 11.
    Joshi P, Joshi HC, Sanghi SK, Kundu S (2010) Immobilization of monoamine oxidase on eggshell membrane and its application in designing an amperometric biosensor for dopamine. Microchim Acta 169:383–388CrossRefGoogle Scholar
  12. 12.
    Zheng G, Chen M, Liu XY, Zhou J, Xie J, Diao GW (2014) Self assembled thiolated calix[n]arene (n = 4, 6, 8) films on gold electrodes and application for electrochemical determination dopamine. Electrochim Acta 136:301–309CrossRefGoogle Scholar
  13. 13.
    Sanghavi BJ, Wolfbeis OS, Hirsch T, Swami NS (2015) Nanomaterial-based electrochemical sensing of neurological drugs and neurotransmitters. Microchim Acta 182:1–41CrossRefGoogle Scholar
  14. 14.
    Ma H F, Chen TT, Luo Y, Kong FY, Fan DH, Fang HL, Wang W (2015) Electrochemical determination of dopamine using octahedral SnO2nanocrystals bound to reduced graphene oxide nanosheets. Microchim Acta182: 2001–2007.Google Scholar
  15. 15.
    Wu LN, Tan YL, Wang L, Sun SN, Qu ZY, Zhang JM, Fan YJ (2015) Dopamine sensor based on a hybrid material composed of cuprous oxide hollow microspheres and carbon black. Microchim Acta 182:1361–1369.Google Scholar
  16. 16.
    Zhang QL, Feng JX, Wang AJ, Wei J, Lv ZY, Feng JJ (2015) A glassy carbon electrode modified with porous gold nanosheets for simultaneous determination of dopamine and acetaminophen. Microchim Acta 182:589–595CrossRefGoogle Scholar
  17. 17.
    Ma W, Long YT (2014) Quinone/hydroquinone-functionalized biointerfaces for biological applications from themacro- to Nano-scale. Chem Soc Rev 43:30–51CrossRefGoogle Scholar
  18. 18.
    Katritzky AR, Fedoseyenko D, Mohapatra PP, Steel PJ (2008) Reactions of p-benzoquinone with sulfur nucleophiles. Synthesis 777-787Google Scholar
  19. 19.
    Bulovas A, Dirvianskytė N, Talaikytė Z, Niaura G, Valentukonytė S, Butkus E, Razumas V (2006) Electrochemical and structural properties of self-assembled monolayers of 2-methyl-3-(Ω-mercaptoalkyl)-1,4 naphthoquinones on gold. J Electroanal Chem 591:175–188CrossRefGoogle Scholar
  20. 20.
    Dongmo S, Witt J, Wittstock G (2015) Electropolymerization of quinone-polymers onto grafted quinone monolayers: a route towards non-passivating, catalytically active film. Electrochim Acta 155:474–482CrossRefGoogle Scholar
  21. 21.
    Moores B, Simons J, Xu S, Leonenko Z (2011) AFM-assisted fabrication of thiol SAM pattern with alternating quantified surface potential. Nanoscale Res Lett 6:185–190CrossRefGoogle Scholar
  22. 22.
    Laviron E (1979) General expression of the linear potential sweep voltammogram in the case of diffusionless electrochemical systems. J Electroanal Chem 101:19–28CrossRefGoogle Scholar
  23. 23.
    Mukae F, Takemura H, Takehara K (1996) Electrochemical behavior of the naphthoquinone anchored onto a gold electrode through the self-assembled monolayers of aminoalkanethiol. Bull Chem Soc Jpn 69:2461–2464Google Scholar
  24. 24.
    Budavari V, Szűcs Á, Somlai C, Novak M (2002) Noncovalently bonded quinone on self-assembled molecular layers. Electrochim Acta 47:4351–4356CrossRefGoogle Scholar
  25. 25.
    Burie JR, Boussac A, Boullais C, Berger G, Mattioli T, Mioskowski C, Nabedryk E, Breton J (1995) FTIR spectroscopy of UV-generated quinone radicals: evidence for an intramolecular hydrogen atom transfer in ubiquinone, naphthoquinone and plastoquinone. J Phys Chem 99:4059–4070CrossRefGoogle Scholar
  26. 26.
    Grafton AK, Wheeler RA (1997) A comparison of the properties of various fused-ring quinones and their radical anions using hartree-fock and hybrid hartree-fock/density functional methods. J Phys Chem A101:7154–7166CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Wien 2016

Authors and Affiliations

  1. 1.Université de Tunis El-Manar, Faculté des Sciences de Tunis, Département de Chimie, Laboratoire de Chimie Analytique & Electrochimie (LR99ES15)TunisTunisia
  2. 2.Laboratoire Méthodes et Techniques d’Analyse, Institut National de Recherche et d’Analyse Physico-Chimique (INRAP), BioTechPole Sidi ThabetArianaTunisia

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