Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Thiourea linked glycolipid-assisted synthesis of sub-micrometer sized polyaniline spheres for enzyme less sensing of dopamine

Abstract

A simple methodology of synthesizing sub-micrometer sized polyaniline (PANI) spheres using gold electrodes with thiourea linked glycolipid self-assembly for the selective detection of dopamine (DA) is reported here. The synthesis was carried out using a potentiodynamic polymerization method. The self-assembled thiourea linked glycolipid on the gold electrodes and the same lipid acting as the surface directing agent for the formation of polyaniline microspheres is the highlighting factor in this work. The biocompatible sub-micrometer polyaniline spheres are characterized using scanning electron microscopy and transmission electron microscopy studies. Amperometry and electrochemical impedance spectroscopy were employed to estimate the concentration of dopamine. The amperometric studies reveal a linear range of ~ 1 to 640 μM, sensitivity of 370 μA cm−2 μM−1, a very low detection limit of 10 nM, and a response time of ~ 5 s. The interference from l-Dopa, ascorbic acid and uric acid has been minimized on account of the Nafion (Nf) coating and selectivity of the electrode. Real sample analysis was carried out using standard addition method.

Graphic abstract

Schematic representation for the formation of sub-micrometer PANI spheres using thiourea linked glycolipid on Au electrodes for sensing of dopamine.

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

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

References

  1. 1.

    Friend RH, Gymer RW, Holmes AB, Burroughes JH, Marks RN, Taliani C, Bradley DDC, Dos SDA, Bredas JL, Logdlund M, Salaneck WR (1999) Electroluminescence in conjugated polymers. Nature 397:121–128. https://doi.org/10.1038/16393

  2. 2.

    Wang D, Gong X, Heeger PS, Rininsland F, Bazan GC, Heeger AJ (2002) Biosensors from conjugated polyelectrolyte complexes. PNAS 99:49–53. https://doi.org/10.1073/pnas.012581399

  3. 3.

    Salahandish R, Ghaffarinejad A, Naghib SM, Niyazi A, Majidzadeh K, Janmaleki M, Nezhad AS (2019) Sandwich-structured nanoparticles-grafted functionalized graphene based 3D nanocomposites for high-performance biosensors to detect ascorbic acid biomolecule. Sci Rep 9:1226. https://doi.org/10.1038/s41598-018-37573-9

  4. 4.

    Wang M, Cui MZ, Liu W, Liu X (2019) Highly dispersed conductive polypyrrole hydrogels as sensitive sensor for simultaneous determination of ascorbic acid, dopamine and uric acid. J Electroanal Chem 832:174–181. https://doi.org/10.1016/j.jelechem.2018.10.057

  5. 5.

    Wilson GS, Johnson MA (2008) In-vivo electrochemistry: what can we learn about living systems? Chem Rev 108:2462–2481. https://doi.org/10.1021/cr068082i

  6. 6.

    Zhang L, Teshima N, Hasebe T, Kurihara M, Kawashima T (1999) Flow-injection determination of trace amounts of dopamine by chemiluminescence detection. Talanta 50:677–683. https://doi.org/10.1016/s0039-9140(99)00164-2

  7. 7.

    Nikolelis DP, Drivelos DA, Simantiraki MG, Koinis S (2004) An optical spot test for the detection of dopamine in human urine using stabilized in air lipid films. Anal Chem 76:2174–2180. https://doi.org/10.1021/ac0499470

  8. 8.

    Lakshmi D, Bossi A, Whitcombe MJ, Chianella I, Fowler SA, Subrahmanyam S, Piletska EV, Piletsky SA (2009) Electrochemical sensor for catechol and dopamine based on a catalytic molecularly imprinted polymer-conducting polymer hybrid recognition element. Anal Chem 81:3576–3584. https://doi.org/10.1021/ac802536p

  9. 9.

    Vázquez-Guardado A, Barkam S, Peppler M, Biswas A, Dennis W, Das S, Seal S, Chanda D (2018) Enzyme-free plasmonic biosensor for direct detection of neurotransmitter dopamine from whole blood. Nano Lett 19:449–454. https://doi.org/10.1021/acs.nanolett.8b04253

  10. 10.

    Chen PY, Nien PC, Ho KC (2009) Highly selective dopamine sensor based on an imprinted SAM/mediator gold electrode. Procedia Chem 1:285–288. https://doi.org/10.1016/j.proche.2009.07.071

  11. 11.

    Kalimuthu P, John SA (2009) Electropolymerized film of functionalized thiadiazole on glassy carbon electrode for the simultaneous determination of ascorbic acid, dopamine and uric acid. Bioelectrochemistry 77:13–18. https://doi.org/10.1016/j.bioelechem.2009.04.010

  12. 12.

    Sun F, Zeng J, Jing M et al (2018) Genetically encoded fluorescent sensor enables rapid and specific detection of dopamine in flies, fish, and mice. Cell 174:481–496. https://doi.org/10.1016/j.cell.2018.06.042

  13. 13.

    He Q, Liu J, Liu X, Li G, Deng P, Liang J (2018) Preparation of Cu2O-reduced grapheme nanocomposite modified electrodes towards ultrasensitive dopamine detection. Sensors 18:199–212. https://doi.org/10.3390/s18010199

  14. 14.

    Yan W, Feng X, Chen X, Li X, Zhu JJ (2008) A selective dopamine biosensor based on AgCl@polyaniline core–shell nanocomposites. Bioelectrochemistry 72:21–27. https://doi.org/10.1016/j.bioelechem.2007.07.003

  15. 15.

    Zablocka I, Zolopa MW, Winkler K (2018) Electrochemical detection of dopamine at a gold electrode modified with a polypyrrole–mesoporous silica molecular sieves (MCM-48) film. Int J Mol Sci 20:111–128. https://doi.org/10.3390/ijms20010111

  16. 16.

    Cui X, Fang X, Zhao H, Ren H (2017) An electrochemical sensor for dopamine based on polydopamine modified reduced graphene oxide anchored with tin dioxide and gold nanoparticles. Anal Methods 9:5322–5332. https://doi.org/10.1039/C7AY00991G

  17. 17.

    Kim DS, Kang ES, Baek S, Choo SS, Chung YH, Lee D, Min J, Kim TH (2018) Electrochemical detection of dopamine using periodic cylindrical gold nanoelectrode arrays. Sci Rep 8:14049. https://doi.org/10.1038/s41598-018-32477-0

  18. 18.

    Varki A, Cummings RD, Esko JD, Freeze HH, Stanley P, Bertozzi CR, Hart GW, Etzler ME (eds) (2009) Essentials of glycobiology, 2nd edn. Cold Spring Harbor Laboratory Press, New York

  19. 19.

    Goodby JW, Gortz V, Cowling SJ, Mackenzie G, Martin P, Plusquellec D, Benvegnu T, Boullanger P, Lafont D, Queneau Y, Chambert S, Fitremann J (2007) Thermotropic liquid crystalline glycolipids. Chem Soc Rev 36:1971–2032. https://doi.org/10.1039/B708458G

  20. 20.

    Faivre V, Rosilio V (2011) Interest of glycolipids in drug delivery: from physicochemical properties to drug targeting. Expert Opin Drug Deliv 7:1031–1048. https://doi.org/10.1517/17425247.2010.511172

  21. 21.

    Kamiya S, Minamikawa H, Jung JH, Yang B, Masuda M, Shimizu T (2005) Molecular structure of glucopyranosylamide lipid and nanotube morphology. Langmuir 21:743–750. https://doi.org/10.1021/la047765v

  22. 22.

    Hakkinen H (2012) The gold-sulfur interface at the nanoscale. Nat Chem 4:443–455. https://doi.org/10.1038/nchem.1352

  23. 23.

    Mathiselvam M, Loganathan D, Varghese B (2013) Synthesis and characterization of thiourea- and urea-linked glycolipids as low-molecular-weight hydrogelators. RSC Adv 3:14528–14542. https://doi.org/10.1039/C3RA42041H

  24. 24.

    Mauritz KA, Moore RB (2004) State of understanding of Nafion. Chem Rev 104:4535–4585. https://doi.org/10.1021/cr0207123

  25. 25.

    Tessensohn ME, Hirao H, Webster RD (2013) Electrochemical properties of phenols and quinones in organic solvents are strongly influenced by hydrogen bonding with water. J Phys Chem C 117:1081–1090. https://doi.org/10.1021/jp311007m

  26. 26.

    Foster RJ, Keyes TE, Zoski CG (eds) (2007) Handbook of electrochemistry, Chapter 6. Elsevier, Amsterdam

  27. 27.

    Yu HN, Pang YC, Tang JY (2015) Polyaniline nanofiber modified platinum electrode used to determination of dopamine by square wave voltammetry technique. Int J Electrochem Sci 10:8353–8360

  28. 28.

    Li X, Rong J, Wei B (2010) Electrochemical behavior of single-walled carbon nanotube supercapacitors under compressive stress. ACS Nano 4:6039–6049. https://doi.org/10.1021/nn101595y

  29. 29.

    Kan X, Zhou H, Li C, Zhu A, Xing Z, Zhao Z (2012) Imprinted electrochemical sensor for dopamine recognition and determination based on a carbon nanotube/polypyrrole film. Electrochim Acta 63:69–75. https://doi.org/10.1016/j.electacta.2011.12.086

  30. 30.

    Ramya R, Sangaranarayanan MV (2012) Polypyrrole microfibers synthesized with Quillaja Saponin for sensing of catechol. Sens Actuat B Chem 173:40–51. https://doi.org/10.1016/j.snb.2012.05.034

  31. 31.

    Ramya R, Sangaranarayanan MV (2013) Electrochemical sensing of glucose using polyaniline nanofiber dendrites-amperometric and impedimetric analysis. J Appl Polym Sci 129:735–747. https://doi.org/10.1002/app.38770

  32. 32.

    Qi L, Thomas E, White SH, Smith SK, Lee CA, Wilson LR, Sombers LA (2016) Unmasking the effects of L-DOPA on rapid dopamine signaling with an improved approach for Nafion coating carbon-fiber microelectrodes. Anal Chem 88:8129–8136. https://doi.org/10.1021/acs.analchem.6b01871

  33. 33.

    Maouche N, Guergouri M, Gam-Derouich S, Jouini M, Nessark B, Chehimi MM (2012) Molecularly imprinted polypyrrole films: some key parameters for electrochemical picomolar detection of dopamine. J Electroanal Chem 685:21–27. https://doi.org/10.1016/j.jelechem.2012.08.020

  34. 34.

    Liu S, Xing X, Yu J, Lian W, Li J, Cui M, Huang J (2012) A novel label-free electrochemical aptasensor based on graphene–polyaniline composite film for dopamine determination. Biosens Bioelectron 36:186–191. https://doi.org/10.1016/j.bios.2012.04.011

  35. 35.

    Ferreira M, Dinelli LR, Wohnrath K, Batista AA, Oliveira ON (2004) Langmuir-Blodgett films from polyaniline/ruthenium complexes as modified electrodes for detection of dopamine. Thin Solid Films 446:301–306. https://doi.org/10.1016/j.tsf.2003.10.006

  36. 36.

    Tsai TC, Han HZ, Cheng CC, Chen LC, Chang HC, Chen JJJ (2012) Modification of platinum microelectrode with molecularly imprinted over-oxidized polypyrrole for dopamine measurement in rat striatum. Sens Actuat B Chem 171–172:93–101. https://doi.org/10.1016/j.snb.2011.07.052

  37. 37.

    Gholivand MB, Amiri M (2012) Simultaneous detection of dopamine and acetaminophen by modified gold electrode with polypyrrole/aszophloxine film. J Electroanal Chem 676:53–59. https://doi.org/10.1016/j.jelechem.2012.05.001

  38. 38.

    Jiang X, Lin X (2005) Overoxidized polypyrrole film directed DNA immobilization for construction of electrochemical micro-biosensors and simultaneous determination of serotonin and dopamine. Anal Chim Acta 537:145–151. https://doi.org/10.1016/j.aca.2005.01.049

  39. 39.

    Harley CC, Rooney AD, Breslin CB (2010) The selective detection of dopamine at a polypyrrole film doped with sulfonated beta-cyclodextrins. Sens Actuat B Chem 150:498–504. https://doi.org/10.1016/j.snb.2010.09.012

  40. 40.

    Pihel K, Walker QD, Wightman RM (1996) Overoxidized polypyrrole-coated carbon fiber microelectrodes for dopamine measurements with fast-scan cyclic voltammetry. Anal Chem 68:2084–2089. https://doi.org/10.1021/ac960153y

Download references

Acknowledgements

This work was supported by the Science and Engineering Research Board, Government of India. The idea of employing glycolipid-assisted synthesis of conducting polymers was suggested to us by Prof Dr. D. Loganathan, Department of Chemistry, Indian Institute of Technology-Madras who passed away during the preparation of this manuscript. Hence, this paper is dedicated to him.

Funding

This research received no external funding.

Author information

The idea was conceptualized by Prof. M.V.S and Prof. D.L, and all the research relating to methodology, software, validation, analysis, investigation, data curation and writing was done by R.R and M.M. The review and editing, visualization, resources, supervision, project administration were provided by Prof. M.V.S.

Correspondence to Ramya Ramkumar.

Ethics declarations

Conflicts of interest

The authors declare no conflict of interest.

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

Verify currency and authenticity via CrossMark

Cite this article

Ramkumar, R., Mathiselvam, M. & Sangaranarayanan, M.V. Thiourea linked glycolipid-assisted synthesis of sub-micrometer sized polyaniline spheres for enzyme less sensing of dopamine. J Appl Electrochem (2020). https://doi.org/10.1007/s10800-020-01402-7

Download citation

Keywords

  • Sub-micrometer polyaniline
  • Thiourea linked glycolipid
  • Amperometry and electrochemical impedance spectroscopy