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Poly(3-methylthiophene) modified gold sensor for determination of 3,4-dihydroxyphenylacetic acid, ascorbic acid and uric acid in biological fluids using voltammetric techniques

Yıl 2019, Cilt: 23 Sayı: 1, 25 - 33, 27.06.2025

Ebru Kuyumcu Savan , Gamze Erdoğdu

Öz

Electrochemical polymerization was carried out in a one-compartment cell containing deaerated
acetonitrile, and 100 mM tetrabutylammonium tetrafluoroborate monomer of 3-methylthiophene. The polymer films
were grown on a gold electrode by bulk electrolysis at 1.700 V (vs. Ag/Ag+). The modified sensor showed an excellent
electrocatalytic effect towards oxidation of the mixture of 3,4-dihydroxyphenylacetic acid (DOPAC), ascorbic acid and
uric acid, which appeared at a pH range of 2-11 by differential pulse voltammetry (DPV ) techniques. The best results
for determination of DOPAC were obtained by DPV in PBS (pH 7.00). A calibration curve was obtained in the DOPAC
concentration range of 1.0-50.0 μM (r = 0.9948). Limit of detection and limit of quantification were found as 0.066 μM
and 0.220 μM, respectively. The results of the experiments indicated that the sensor has good stability, sensitivity and
reproducibility for at least one month if stored in dry air.

Anahtar Kelimeler

Poly (3-methylthiophene) 3 4-dihydroxyphenylacetic acid ascorbic acid uric acid voltammetry

Kaynakça

  • [1] Liu A, Honma I, Zhou H. Amperometric biosensor based on tyrosinase-conjugated polysacchride hybrid film: Selective determination of nanomolar neurotransmitters metabolite of 3,4-dihydroxyphenylacetic acid (DOPAC) in biological fluid. Biosens Bioelectron. 2005; 21: 809–816. [CrossRef]
  • [2] Kalimuthu P, John SA. Selective determination of 3,4 dihydroxyphenylacetic acid in the presence of ascorbic and uric acids using polymer film modified electrode. J Chem Sci. 2011; 123: 349–355. [CrossRef]
  • [3] Wu Z, Zhao H, Xue Y, He Y, Li X, Yuan Z. Poly (pyridine-3-boronic acid)/Multiwalled Carbon Nanotubes Modified Glassy Carbon Electrodes for Simultaneous. Electroanalysis. 2010; 22: 2196–2201. [CrossRef]
  • [4] Moriyasu K, Ichinose T, Nakahata A, Tanaka M, Matsui T, Furuya SI. The dipeptides Ile-Tyr and Ser-Tyr exert distinct effects on catecholamine metabolism in the mouse brainstem. Inter J Pept. 2016; Article ID 6020786. [CrossRef]
  • [5] Raj CR, Ohsaka T. Analytical applications of functionalized self-assembled monolayers on gold electrode: voltammetric sensing of DOPAC at the physiological level. Electroanalysis. 2002; 14: 679-684. [CrossRef]
  • [6] Stamford JA, Palij P, Davidson C, Trout SJ. Fast cyclic voltammetry: neurotransmitter measurement in “real time” and “real space”. J Bioelectrochem Bioenerg. 1995; 38(2): 289-296. [CrossRef]
  • [7] Valentini F, Orlanducci S, Terranova ML, Amine A, Palleschi G. Carbon nanotubes as electrode materials for the assembling of new electrochemical biosensors. Sens Actuators B. 2004; 100(1-2): 117-125. [CrossRef]
  • [8] Yan J, Zhou Y, Yu P, Su L, Mao L, Zhang D, Zhu D. An electrochemical sensor for 3,4-dihydroxyphenylacetic acid with carbon nanotubes as electronic transducer and synthetic cyclophane as recognition element. Chem Commun. 2008; 36: 4330-4332. [CrossRef]
  • [9 Salimi A, MamKhezri H, Hallaj R. Simultaneous determination of ascorbic acid, uric acid and neuro-transmitters with a carbon ceramic electrode prepared by Sol-Gel technique. Talanta. 2006; 70(4): 823-832. [CrossRef]
  • [10] Roy PR, Saha MS, Okajima T, Park SG, Fujishima A, Ohsaka T. Selective Detection of dopamine and its metabolite, DOPAC, in the presence of ascorbic acid using diamond electrode modified by the polymer film. Electroanalysis. 2004; 16(21): 1777-1784. [CrossRef]
  • [11] Raj CR, Behera SJ. Electrochemical studies of 6-mercaptonicotinic acid monolayer on Au electrode. Electroanal Chem. 2005; 581(1): 61-69. [CrossRef]
  • [12] Raj CR, Ohsaka T. Simultaneous electroanalysis of ascorbic acid, dihydroxyphenylacetic acid, homovanillic acid and uric acid using gold electrode modified with cationic self-assembled monolayers. Chem Lett. 2001; 30(7): 670-671. [CrossRef]
  • [13] Kalimuthu P, John SAJ. Size dependent electrocatalytic activity of gold nanoparticles immobilized onto three dimensional sol–gel network. J Electroanal Chem. 2008; 617(2): 164-170. [CrossRef]
  • [14] Maldonado S, Morin S, Stevenson KJ. Electrochemical oxidation of cathecholamines and cathechol at carbon nanotube electrodes. Analyst. 2006; 131(2): 262-267. [CrossRef]
  • [15] Wang J, Li M, Shi Z, Li N, Gu Z. Electrocatalytic oxidation of 3,4-dihydroxyphenylacetic acid at a glassy carbon electrode modified with single-wall carbon nanotubes. Electrochim Acta. 2001; 47(4): 651-657. [CrossRef]
  • [16] Liu A, Honma I, Zhou H. Electrochemical biosensor based on protein–polysaccharide hybrid for selective detection of nanomolar dopamine metabolite of 3,4-dihydroxyphenylacetic acid (DOPAC). Electrochem Commun. 2005; 7(2): 233–236. [CrossRef]
  • [17] Curulli A, Valentini F, Padeletti G, Viticoli M, Caschera D, Palleschi G. Smart (Nano) materials: TiO2 nanostructured films to modify electrodes for assembling of new electrochemical probes. Sens Act B: Chem. 2005; 111-112: 441-449. [CrossRef]
  • [18] Yeung PKF, Buckley SJ, Pedder SCJ, Dingemanse J. Determination of 3,4-dihydroxyphenylacetic acid and 5 hydroxyindoleacetic acid in human plasma by a simple and rapid high-performance liquid chromatography assay. J Pharm Sci. 1996; 85(4): 451-453. [CrossRef]
  • [19] Adcock JL, Barnett NW, Costin JW, Francis PS, Lewis SW. Determination of selected neurotransmitter metabolites using monolithic column chromatography coupled with chemiluminescence detection. Talanta. 2005; 67(3): 585-589. [CrossRef]
  • [20] Drujan BD, Alvarez N, Borges JMD. A method for determination of 3,4-dihydroxyphenylacetic acid and 3,4 dihydroxymandelic acid in urine. Anal Biochem. 1966; 15(1): 8-17. [CrossRef]
  • [21] Liu A, Wei M, Honma I, Zhou H. Biosensing properties of titanatenanotube films: selective detection of dopamine in the presence of ascorbate and uric acid. Adv Functional Mat. 2006; 16(3): 371-376. [CrossRef]
  • [22] Wu Z, Zhao H, Xue Y, Li X, He Y, Yuan Z. Simultaneous determination of 3,4-dihydroxyphenylacetic acid, uric acid and ascorbic acid by poly(L-Arginine)/multi-walled carbon nanotubes composite film. J Nanosci Nanotechnol. 2011; 11(2): 1013-1018. [CrossRef]
  • [23] DuVall SH, McCreery RL. Control of catechol and hydroquinone electron-transfer kinetics on native and modified glassy carbon electrodes. Anal Chem. 1999; 71(20): 4594-4602. [CrossRef]
  • https://doi.org/10.12991/jrp.2018.105 J Res Pharm 2019; 23(1): 25-33 32 Journal of Research in Pharmacy Kuyumcu Savan and Erdoğdu. Determination of DOPAC at poly (3MT) modified sensor Research Article [24] Rubianes MD, Arribas AS, Bermejo E, Chicharro M, Zapardiel A, Rivas G. Carbon nanotubes paste electrodes modified with a melanic polymer: Analytical applications for the sensitive and selective quantification of dopamine. Sens Act B: Chem. 2010; 144(1): 274-279. [CrossRef]
  • [25] Mulla IA, Lowry JP, Serra PA, O’Neill RD. Development of a voltammetric technique for monitoring brain dopamine metabolism: compensation for interference caused by DOPAC electrogenerated during homovanillic acid detection. Analyst. 2009; 134: 893–898. [CrossRef]
  • [26] Huang SW, Ho KC. An all-thiophene electrochromic device fabricatedwith poly(3-methylthiophene) and poly(3,4 ethylenedioxythiophene). Sol Energ Mat Sol Cells. 2006; 90: 491–505. [CrossRef]
  • [27] Millán WM, Smit MA. Study of electrocatalysts for oxygen reduction based on electroconducting polymer and nickel. J Appl Polym Sci. 2009; 112: 2959–2967. [CrossRef]
  • [28] Liu C, Lu B, Fan C, Xu J, Li Y, Jiang F. Electrochemical copolymerization of 9,10-dihydrophenanthrene and 3 methylthiophene and characterization of their copolymer with tunable fluorescence properties. J Solid State Electrochem. 2010; 14: 1153–1161. [CrossRef]
  • [29] Huong VT, Shimanouchi T, Quan DP, Umakoshi H, Viet PH, Kuboi R. Polymethylthiophene/Nafion-modified glassy carbon electrode for selective detection of dopamine in the presence of ascorbic acid. J Appl Electrochem. 2009; 39: 2035–2042. [CrossRef]
  • [30] Zhang H, Zhao J, Liu H, Liu R, Wang H, Liu J. Electrochemical determination of diphenolsand their mixtures at the multiwall carbon nanotubes/poly(3-methylthiophene) modified glassy carbon electrode. Microchim Acta. 2010;169: 277–282. [CrossRef]
  • [31] ICH Guideline Q2A (R1), Validation of analytical procedures; Text and methodology, European Medicines Agency, London, UK, 2006. [CrossRef]
  • [32] Savan EK, Erdoğdu G. Determination of 3,4-dihydroxyphenylacetic acid in the presence of ascorbic acid and uric acid at poly(p-aminobenzene sulfonic acid) conducting polymer electrode. Polym Bull. 2017; 74: 4349–4360. [CrossRef]
  • [33] Sadikoglu M, Saglikoglu G, Yagmur S, Orta E, Yilmaz S. Voltammetric determination of acyclovir in human urine using ultra trace graphite and glassy carbon electrodes. Curr Anal Chem. 2011; 7(2): 130-135. [CrossRef]

Yıl 2019, Cilt: 23 Sayı: 1, 25 - 33, 27.06.2025

Ebru Kuyumcu Savan , Gamze Erdoğdu

Öz

Kaynakça

  • [1] Liu A, Honma I, Zhou H. Amperometric biosensor based on tyrosinase-conjugated polysacchride hybrid film: Selective determination of nanomolar neurotransmitters metabolite of 3,4-dihydroxyphenylacetic acid (DOPAC) in biological fluid. Biosens Bioelectron. 2005; 21: 809–816. [CrossRef]
  • [2] Kalimuthu P, John SA. Selective determination of 3,4 dihydroxyphenylacetic acid in the presence of ascorbic and uric acids using polymer film modified electrode. J Chem Sci. 2011; 123: 349–355. [CrossRef]
  • [3] Wu Z, Zhao H, Xue Y, He Y, Li X, Yuan Z. Poly (pyridine-3-boronic acid)/Multiwalled Carbon Nanotubes Modified Glassy Carbon Electrodes for Simultaneous. Electroanalysis. 2010; 22: 2196–2201. [CrossRef]
  • [4] Moriyasu K, Ichinose T, Nakahata A, Tanaka M, Matsui T, Furuya SI. The dipeptides Ile-Tyr and Ser-Tyr exert distinct effects on catecholamine metabolism in the mouse brainstem. Inter J Pept. 2016; Article ID 6020786. [CrossRef]
  • [5] Raj CR, Ohsaka T. Analytical applications of functionalized self-assembled monolayers on gold electrode: voltammetric sensing of DOPAC at the physiological level. Electroanalysis. 2002; 14: 679-684. [CrossRef]
  • [6] Stamford JA, Palij P, Davidson C, Trout SJ. Fast cyclic voltammetry: neurotransmitter measurement in “real time” and “real space”. J Bioelectrochem Bioenerg. 1995; 38(2): 289-296. [CrossRef]
  • [7] Valentini F, Orlanducci S, Terranova ML, Amine A, Palleschi G. Carbon nanotubes as electrode materials for the assembling of new electrochemical biosensors. Sens Actuators B. 2004; 100(1-2): 117-125. [CrossRef]
  • [8] Yan J, Zhou Y, Yu P, Su L, Mao L, Zhang D, Zhu D. An electrochemical sensor for 3,4-dihydroxyphenylacetic acid with carbon nanotubes as electronic transducer and synthetic cyclophane as recognition element. Chem Commun. 2008; 36: 4330-4332. [CrossRef]
  • [9 Salimi A, MamKhezri H, Hallaj R. Simultaneous determination of ascorbic acid, uric acid and neuro-transmitters with a carbon ceramic electrode prepared by Sol-Gel technique. Talanta. 2006; 70(4): 823-832. [CrossRef]
  • [10] Roy PR, Saha MS, Okajima T, Park SG, Fujishima A, Ohsaka T. Selective Detection of dopamine and its metabolite, DOPAC, in the presence of ascorbic acid using diamond electrode modified by the polymer film. Electroanalysis. 2004; 16(21): 1777-1784. [CrossRef]
  • [11] Raj CR, Behera SJ. Electrochemical studies of 6-mercaptonicotinic acid monolayer on Au electrode. Electroanal Chem. 2005; 581(1): 61-69. [CrossRef]
  • [12] Raj CR, Ohsaka T. Simultaneous electroanalysis of ascorbic acid, dihydroxyphenylacetic acid, homovanillic acid and uric acid using gold electrode modified with cationic self-assembled monolayers. Chem Lett. 2001; 30(7): 670-671. [CrossRef]
  • [13] Kalimuthu P, John SAJ. Size dependent electrocatalytic activity of gold nanoparticles immobilized onto three dimensional sol–gel network. J Electroanal Chem. 2008; 617(2): 164-170. [CrossRef]
  • [14] Maldonado S, Morin S, Stevenson KJ. Electrochemical oxidation of cathecholamines and cathechol at carbon nanotube electrodes. Analyst. 2006; 131(2): 262-267. [CrossRef]
  • [15] Wang J, Li M, Shi Z, Li N, Gu Z. Electrocatalytic oxidation of 3,4-dihydroxyphenylacetic acid at a glassy carbon electrode modified with single-wall carbon nanotubes. Electrochim Acta. 2001; 47(4): 651-657. [CrossRef]
  • [16] Liu A, Honma I, Zhou H. Electrochemical biosensor based on protein–polysaccharide hybrid for selective detection of nanomolar dopamine metabolite of 3,4-dihydroxyphenylacetic acid (DOPAC). Electrochem Commun. 2005; 7(2): 233–236. [CrossRef]
  • [17] Curulli A, Valentini F, Padeletti G, Viticoli M, Caschera D, Palleschi G. Smart (Nano) materials: TiO2 nanostructured films to modify electrodes for assembling of new electrochemical probes. Sens Act B: Chem. 2005; 111-112: 441-449. [CrossRef]
  • [18] Yeung PKF, Buckley SJ, Pedder SCJ, Dingemanse J. Determination of 3,4-dihydroxyphenylacetic acid and 5 hydroxyindoleacetic acid in human plasma by a simple and rapid high-performance liquid chromatography assay. J Pharm Sci. 1996; 85(4): 451-453. [CrossRef]
  • [19] Adcock JL, Barnett NW, Costin JW, Francis PS, Lewis SW. Determination of selected neurotransmitter metabolites using monolithic column chromatography coupled with chemiluminescence detection. Talanta. 2005; 67(3): 585-589. [CrossRef]
  • [20] Drujan BD, Alvarez N, Borges JMD. A method for determination of 3,4-dihydroxyphenylacetic acid and 3,4 dihydroxymandelic acid in urine. Anal Biochem. 1966; 15(1): 8-17. [CrossRef]
  • [21] Liu A, Wei M, Honma I, Zhou H. Biosensing properties of titanatenanotube films: selective detection of dopamine in the presence of ascorbate and uric acid. Adv Functional Mat. 2006; 16(3): 371-376. [CrossRef]
  • [22] Wu Z, Zhao H, Xue Y, Li X, He Y, Yuan Z. Simultaneous determination of 3,4-dihydroxyphenylacetic acid, uric acid and ascorbic acid by poly(L-Arginine)/multi-walled carbon nanotubes composite film. J Nanosci Nanotechnol. 2011; 11(2): 1013-1018. [CrossRef]
  • [23] DuVall SH, McCreery RL. Control of catechol and hydroquinone electron-transfer kinetics on native and modified glassy carbon electrodes. Anal Chem. 1999; 71(20): 4594-4602. [CrossRef]
  • https://doi.org/10.12991/jrp.2018.105 J Res Pharm 2019; 23(1): 25-33 32 Journal of Research in Pharmacy Kuyumcu Savan and Erdoğdu. Determination of DOPAC at poly (3MT) modified sensor Research Article [24] Rubianes MD, Arribas AS, Bermejo E, Chicharro M, Zapardiel A, Rivas G. Carbon nanotubes paste electrodes modified with a melanic polymer: Analytical applications for the sensitive and selective quantification of dopamine. Sens Act B: Chem. 2010; 144(1): 274-279. [CrossRef]
  • [25] Mulla IA, Lowry JP, Serra PA, O’Neill RD. Development of a voltammetric technique for monitoring brain dopamine metabolism: compensation for interference caused by DOPAC electrogenerated during homovanillic acid detection. Analyst. 2009; 134: 893–898. [CrossRef]
  • [26] Huang SW, Ho KC. An all-thiophene electrochromic device fabricatedwith poly(3-methylthiophene) and poly(3,4 ethylenedioxythiophene). Sol Energ Mat Sol Cells. 2006; 90: 491–505. [CrossRef]
  • [27] Millán WM, Smit MA. Study of electrocatalysts for oxygen reduction based on electroconducting polymer and nickel. J Appl Polym Sci. 2009; 112: 2959–2967. [CrossRef]
  • [28] Liu C, Lu B, Fan C, Xu J, Li Y, Jiang F. Electrochemical copolymerization of 9,10-dihydrophenanthrene and 3 methylthiophene and characterization of their copolymer with tunable fluorescence properties. J Solid State Electrochem. 2010; 14: 1153–1161. [CrossRef]
  • [29] Huong VT, Shimanouchi T, Quan DP, Umakoshi H, Viet PH, Kuboi R. Polymethylthiophene/Nafion-modified glassy carbon electrode for selective detection of dopamine in the presence of ascorbic acid. J Appl Electrochem. 2009; 39: 2035–2042. [CrossRef]
  • [30] Zhang H, Zhao J, Liu H, Liu R, Wang H, Liu J. Electrochemical determination of diphenolsand their mixtures at the multiwall carbon nanotubes/poly(3-methylthiophene) modified glassy carbon electrode. Microchim Acta. 2010;169: 277–282. [CrossRef]
  • [31] ICH Guideline Q2A (R1), Validation of analytical procedures; Text and methodology, European Medicines Agency, London, UK, 2006. [CrossRef]
  • [32] Savan EK, Erdoğdu G. Determination of 3,4-dihydroxyphenylacetic acid in the presence of ascorbic acid and uric acid at poly(p-aminobenzene sulfonic acid) conducting polymer electrode. Polym Bull. 2017; 74: 4349–4360. [CrossRef]
  • [33] Sadikoglu M, Saglikoglu G, Yagmur S, Orta E, Yilmaz S. Voltammetric determination of acyclovir in human urine using ultra trace graphite and glassy carbon electrodes. Curr Anal Chem. 2011; 7(2): 130-135. [CrossRef]
Toplam 33 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Farmasotik Kimya
Bölüm Articles
Yazarlar

Ebru Kuyumcu Savan

Gamze Erdoğdu

Yayımlanma Tarihi 27 Haziran 2025
Yayımlandığı Sayı Yıl 2019 Cilt: 23 Sayı: 1

Kaynak Göster

APA Kuyumcu Savan, E., & Erdoğdu, G. (2025). Poly(3-methylthiophene) modified gold sensor for determination of 3,4-dihydroxyphenylacetic acid, ascorbic acid and uric acid in biological fluids using voltammetric techniques. Journal of Research in Pharmacy, 23(1), 25-33.
AMA Kuyumcu Savan E, Erdoğdu G. Poly(3-methylthiophene) modified gold sensor for determination of 3,4-dihydroxyphenylacetic acid, ascorbic acid and uric acid in biological fluids using voltammetric techniques. J. Res. Pharm. Haziran 2025;23(1):25-33.
Chicago Kuyumcu Savan, Ebru, ve Gamze Erdoğdu. “Poly(3-Methylthiophene) Modified Gold Sensor for Determination of 3,4-Dihydroxyphenylacetic Acid, Ascorbic Acid and Uric Acid in Biological Fluids Using Voltammetric Techniques”. Journal of Research in Pharmacy 23, sy. 1 (Haziran 2025): 25-33.
EndNote Kuyumcu Savan E, Erdoğdu G (01 Haziran 2025) Poly(3-methylthiophene) modified gold sensor for determination of 3,4-dihydroxyphenylacetic acid, ascorbic acid and uric acid in biological fluids using voltammetric techniques. Journal of Research in Pharmacy 23 1 25–33.
IEEE E. Kuyumcu Savan ve G. Erdoğdu, “Poly(3-methylthiophene) modified gold sensor for determination of 3,4-dihydroxyphenylacetic acid, ascorbic acid and uric acid in biological fluids using voltammetric techniques”, J. Res. Pharm., c. 23, sy. 1, ss. 25–33, 2025.
ISNAD Kuyumcu Savan, Ebru - Erdoğdu, Gamze. “Poly(3-Methylthiophene) Modified Gold Sensor for Determination of 3,4-Dihydroxyphenylacetic Acid, Ascorbic Acid and Uric Acid in Biological Fluids Using Voltammetric Techniques”. Journal of Research in Pharmacy 23/1 (Haziran 2025), 25-33.
JAMA Kuyumcu Savan E, Erdoğdu G. Poly(3-methylthiophene) modified gold sensor for determination of 3,4-dihydroxyphenylacetic acid, ascorbic acid and uric acid in biological fluids using voltammetric techniques. J. Res. Pharm. 2025;23:25–33.
MLA Kuyumcu Savan, Ebru ve Gamze Erdoğdu. “Poly(3-Methylthiophene) Modified Gold Sensor for Determination of 3,4-Dihydroxyphenylacetic Acid, Ascorbic Acid and Uric Acid in Biological Fluids Using Voltammetric Techniques”. Journal of Research in Pharmacy, c. 23, sy. 1, 2025, ss. 25-33.
Vancouver Kuyumcu Savan E, Erdoğdu G. Poly(3-methylthiophene) modified gold sensor for determination of 3,4-dihydroxyphenylacetic acid, ascorbic acid and uric acid in biological fluids using voltammetric techniques. J. Res. Pharm. 2025;23(1):25-33.