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Abstract Keywords Materials and methods Chemicals and materials Apparatus Preparation of modified GCE Results and discussion Electropolymerization of DBA at the GCE surface
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Electrochemical response of DA and AA at poly(DBA) film modified electrode

Effect of scan rate and pH on oxidation of DA

Interference and reproducibility study

Determination of DA

Analytical applications

Table 1

Conclusions
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Acknowledgments References

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Analytical Biochemistry

Volume 381, Issue 2, 15 October 2008, Pages 179184

Determination of dopamine in the presence of

ascorbic acid using poly(3,5-dihydroxy

benzoic acid) film modified electrode

Shurong Hou, Na Zheng, Haiyan Feng, Xiangjun Li , , Zhuobin Yuan College of Chemistry and Chemical Engineering, Graduate University, Chinese Academy

of Sciences, 100049 Beijing, China

Abstract

A polymerized film of 3,5-dihydroxy benzoic acid (DBA) was prepared on the surface of a

glassy carbon electrode (GCE) in neutral solution by cyclic voltammetry (CV). The poly(DBA)
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film-coated GCE exhibited excellent electrocatalytic activity toward the oxidation of dopamine

(DA). A linear range of 1.0 107

to 1.0 104

M and a detection limit of 6.0 108

M were

observed in pH 7.4 phosphate buffer solutions. Moreover, the interference of ascorbic acid (AA)was effectively eliminated. This work provides a simple and easy approach to selective detection

of DA in the presence of AA.

Keywords

Poly(3,5-dihydroxy benzoic acid) film modified electrode; Electrocatalysis; Dopamine; Ascorbic acid

Dopamine (DA)1is an important neurotransmitter molecule of catecholamines that is widely

distributed in the mammalian central nervous system for message transfer. It plays a very

important role in the function of central nervous, renal, hormonal, and cardiovascular systems

[1]. Extreme abnormalities of DA levels will lead to brain disorders such as parkinsonism andschizophrenia[2]and[3]. Therefore, it is essential to develop simple and rapid methods for the

determination of DA in routine analysis.

DA can be easily oxidized electrochemically at conventional electrodes, which have been widely

used to detect it by electrochemical methods[4]and[5]. But it is generally shown that the

reversibility of DA at bare electrode is not obvious and that high overpotentials are required foramperometric detections. Moreover, ascorbic acid (AA) usually coexists with DA in

physiological samples, and the oxidation potentials of these species are too close to be

determined separately at bare electrodes. Besides, the electrode fouling that takes place due tothe adsorption of oxidation products leads to rather poor selectivity and reproducibility[6]. The

ability to determine DA and AA selectively has been a major goal of electroanalytical research.Chemically modified electrodes with various approaches have been attempted to solve the

problems, including self-assembled monolayer[7],[8],[9]and[10], covalent modification[11],[12]and[13], polymer film[14],[15],[16],[17],[18],[19],[20],[21],[22],[23]and[24], and

composite[25],[26],[27],[28],[29],[30]and[31]. Among them, modified electrodes prepared

by electropolymerization have obvious advantages in the detection of analytes. For example,electropolymerization can accelerate transmission of electrons on the surface of electrode, it has

high selectivity and sensitivity due to the film homogeneity in electrochemical deposition, and it

has strong adherence to the electrode surface and large surface area[32]. Furthermore,fabrication of conducting polymer films is flexible and controllable; hence, it provides an

attractive means of detecting DA.

In biological environments (pH 7.4), DA exists as cations, whereas AA exists as anions.Therefore, to get rid of the interference of AA with the determination of DA, the negatively

charged polymer film is considered to be necessary. Xiao and coworkers[33]fabricated a unique

polymer composite modified gold electrode (by self-assembly of 11-mercaptoundecanoic acid[MUA] monolayer on gold surface and then electrochemical esterification of polyethylene glycol

[PEG] with MUA) for selectively detecting DA in the presence of AA. But the current work

employed only electropolymerization to form more negatively charged poly(3,5-dihydroxy
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benzoic acid) [poly(DBA)] film modified electrode, providing a more simple approach with

good selectivity and reproducibility.

3,5-Dihydroxy benzoic acid (DBA) is a molecule that has high electron density of carbonyl and

hydroxyl groups, and its application in the determination of DA has not been reported

previously. In this article, we report for the first time a polymer film of DBA to modify glassycarbon electrode (GCE) and describe the electrochemical behavior of DA and AA. Based on the

different electrocatalytic activities of the modified electrode toward DA and AA, a sensitive and

selective method for determination of DA in the presence of AA was established. Furthermore,the practical application was demonstrated to determine DA in injection with good results.

Therefore, this advantage has a significant attraction in biological and chemical research.

Materials and methods

Chemicals and materials

DBA was obtained from Beijing Chemical Reagent (Beijing, China). Dopamine hydrochloridewas purchased from Acros Organics (Morris Plains, NJ, USA). AA was obtained from Beijing

Chemical Factory (Beijing, China). Uric acid was obtained from Alfa Aesar (Lancaster, UK).

Other chemicals were of analytical reagent grade. Phosphate buffer solutions were prepared by0.1 M KH2PO4 and 0.1 M Na2HPO4 and then adjusting the pH with 0.1 M H3PO4 and 0.1 M

NaOH. All aqueous solutions were prepared in doubly distilled water.

Apparatus

A CHI 660A Electrochemical Workstation (CH Instruments, Austin, TX, USA) was used for

electrochemical measurements. A conventional three-electrode system was employed with a bareor poly(DBA) modified GCE (3.0 mm in diameter) as the working electrode, a platinum wire as

the counter electrode, and a saturated calomel electrode (SCE) as the reference electrode. All

potentials reported in this article were referenced to the SCE. All measurements were performed

at the ambient temperature of the laboratory. The electrolyte solutions were thoroughly degassedwith purging high-purity nitrogen and kept under a nitrogen atmosphere.

Preparation of modified GCE

Prior to modification, the GCE was polished with emery paper and chamois leather containing

0.3 and 0.05 m Al2O3 slurry, respectively, thoroughly rinsed with water, and sonicated in

HNO3, ethanol, and distilled water in turn. After being cleaned, the electrode was immersed in0.1 M NaCl solution containing 2.0 102 M DBA and the potential of working electrode was

cycled between 1.5 and 2.5 V at 100 mV s1

for 20 scans to form poly(DBA) film modified

electrode.

Results and discussion

Electropolymerization of DBA at the GCE surface


6/23

Voltammograms of 2.0 102

M DBA in 0.1 M NaCl solution at a GCE are shown inFig. 1.

From the first cycle, an anodic peak (a) at 1.12 V increased gradually until the third cycle, and

then a new anodic peak (c) appeared at 1.72 V. A cathodic peak (b) appeared in the first cycle

with a potential at 0.55 V. Then larger peaks were observed on continuous scanning, reflecting

the continuous growth of the film. These facts indicated that DBA was deposited on the surface

of GCE by electropolymerization. After modification, the poly(DBA) film electrode wascarefully rinsed with doubly distilled water and then stored in air and prepared to use later.

Fig. 1. Repetitive cyclic voltammograms of 2.0 102

M DBA in 0.1 M NaCl solution.Initial potential:1.5 V; terminal potential: +2.5 V; sensitivity: 1.0 10

4A V

1; scan

rate: 100 mV s1

.

Figure options

Electrochemical response of DA and AA at poly(DBA) film modified electrode

Fig. 2shows cyclic voltammograms of DA and AA in pH 7.4 phosphate buffer solution at a bare

GCE and a poly(DBA) film modified GCE. The electrochemical response of DA and AA at thebare GCE produce an anodic peak at the potentials of 0.274 and 0.328 V, respectively; the peak

potentials are very close and nearly overlap. But at the poly(DBA) film modified electrode, it

could be observed that the modification shifts the oxidation potentials of DA and AA toward

significantly negatively potentials. For DA, the shift is larger; consequently, two well-resolvedpeaks are present. Whereas a well-defined redox wave of DA was observed with the anodic peak

potential at 0.270 V and the corresponding cathodic peak potential at 0.122 V, a new redox wave

appeared at the potentials of 0.224 and 0.299 V. Similar results were also reported in the

literature[15],[16]and[17]. As for AA, the peak potential shifted to 0.036 V.
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Fig. 2. Cyclic voltammograms of DA and AA at a bare GCE (A) and a poly(DBA) film

modified GCE (B) in 0.1 mol L1

phosphate buffer solution (pH 7.4). Scan rate: 100 mV

s1

. (A) a: blank; b: 104

M DA; c: 103

M AA. (B) a: blank; b: 104

M DA; c: 104

M DA

+ 103 M AA.

Figure options

Because theCOOH groups in DBA are dissociated in pH 7.4 phosphate buffer solution,

poly(DBA) exists as anions. Hence, there is a strong electrostatic attraction interaction betweenpositively charged DA and poly(DBA). Such an interaction would lead to an accumulation of

DA on the surface of the modified electrode; thus, an intensive increase in peak current was

observed in pH 7.4 phosphate buffer solution. Although for AA there is a repulsion interactionbetween AA and poly(DBA), because AA exists as an anion at pH 7.4, we can observe only a

small, broad anodic peak at 0.036 V.

Effect of scan rate and pH on oxidation of DA

The effect of scan rate on the oxidation peak current of 1.0 104

M DA was studied. With the

scan rate increasing, the anodic peak current (ipa) increased. A good linearity between the squareroot of scan rate and ipa was obtained within the range of 10 to 240 mV/s, The linear regression

equation was ip (10 A) = 0.99911 + 2.08835 V1/2

(mV/s) with the correlation coefficient

R = 0.99498. The result indicates that the electrode process is controlled by the diffusion of DA.

The effect of pH on the peak potential and current was investigated by cyclic voltammetry in the

presence of 104

M DA in 0.1 M phosphate buffer solution. The peak potential (Epa) shifted

negatively when the pH changed from acid over neutral to basic. The plot ofEpa versus pHshows linearity in the pH range of 5.0 to 8.5 with a slope of 55.09 mV pH

1, revealing that the

proportion of the electron and proton involved in the reactions is 1:1. Because the DA oxidation

is a two-electron process, the number of protons involved is also predicted to be two. Thisaccords with the mechanism of DA oxidation as reported previously[18]and[19]. It can also be

seen fromFig. 3that the peak current of DA reached a maximum at pH 7.4 and then decreased

with the change of pH. Because pH 7.4 was the physiological condition and the response current
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of DA was the highest at this pH, it was chosen as the experiment pH value in the

electrochemical detection of DA.

Fig. 3. Cyclic voltammograms of 1.0 104

M DA at poly(DBA) modified electrode at

different pH values (from a to h: 5.0, 5.5, 6.0, 6.5, 7.0, 7.4, 8.0, and 8.5, respectively).The inset shows the dependence of the oxidized current versus pH of solution. Scan rate:

100 mV s1

.

Figure options

Interference and reproducibility study

Fig. 4shows the electrochemical behavior of a mixture of 1.0 104

M DA and 1.0 103

M

AA at poly(DBA) modified electrodes with different concentrations of DBA in connection with

electropolymerization. It can be seen that when the monomer concentration increased to2.0 10

2M, the oxidation of AA was effectively suppressed at the polymerized film modified

electrode; AA had hardly any interference in the determination of DA. This could be ascribed to

the following reasons. When the monomer concentration increased, the electrostatic repulsionbetween the AA anions and the high electron density of the carbonyl and hydroxyl groups of

poly(DBA) at the modified electrode became stronger and then inhibited the oxidation of AA,

whereas the electrostatic attraction interaction between DA cation and the negative poly(DBA)film promoted the oxidation of DA. Therefore, DA could be detected with excellent sensitivityand selectivity in the presence of AA.
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Fig. 4. Cyclic voltammograms of 1.0 104

M DA + 1.0 103

M AA in 0.1 Mphosphate buffer solution (pH 7.4) at poly(DBA) modified electrodes prepared with

different concentrations of DBA: (a) 104

M; (b) 103

M; (c) 2 102

M. Scan rate:

100 mV s

1

.

Figure options

In the extracellular fluid of the central nervous system, DA exists in only a nanomolar tomicromolar range (0.011 M)[34], whereas the concentration of AA is very high (100

500 M)[35]. As the main interference, AA hinders the accurate detection of DA because theoxidized DA product, dopamine-o-quinone, can be catalytically reduced to DA by AA that again

becomes available for oxidation (as can be seen inFig. 2B, the DA oxidized current increased

when AA exists); however, when the concentration ratio of AA/DA is greater than 1, thisinterference is constant[33]. We carefully examined the oxidation currents of DA at the

poly(DBA) modified GCE in the presence of increasing concentrations of AA (Fig. 5A). Thereis no obvious change in the oxidation currents of DA when the concentration of AA changed

(when the concentration of DA was 50 M, the concentration ratio of AA/DA was 820).Moreover, there was hardly any response for AA oxidation at the poly(DBA) modified electrode.

As can be seen inFig. 5B, the oxidation currents of DA increased proportionally with DAs

concentration while the peak current of AA remained constant, indicating that the poly(DBA)electrode was sensitive only to DA. This means that in the real biological matrixes, where the

AA level is usually more than three orders of magnitude larger than DA, the poly(DBA) film

modified electrode could be used for the determination of DA in the real sample.
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Fig. 5. (A) Differential pulse voltammograms at poly(DBA) modified GCE in pH 7.4

phosphate buffer solution containing 50 M DA in the presence of different

concentrations of AA: (a) 0 M; (b) 400M; (c) 600M; (d) 800M; (e) 1000M. (B)

Differential pulse voltammograms at poly(DBA) modified GCE in pH 7.4 phosphatebuffer solution containing 500 M AA in the presence of different concentrations of DA:

(a) 0 M; (b) 4M; (c) 8M; (d) 12M; (e) 16M.

Figure options

We also examined the influence of other substances on the signals of the DA and found that no

interference occurred in the presence of the following substance: 200-fold uric acid, 200-fold

hippuric acid, 200-fold citric acid, 200-fold glucose, 200-fold cysteine, 1000-fold sodium

chloride, and 1000-fold potassium chloride (with relative standard deviations < 5%).

One of the problems of determination of DA by the bare electrode is the fouling of electrodesurface, but in our experiment we did not notice the inhibition of the activity of the modifier

toward DA detection; the peak current of DA remained constant after the scan cycles of cyclic

voltammograms up to 11 times (seeFig. 6). This can be explained as shown by the equations in

Scheme 1[36]. When the DA is oxidized (Eq. 1), its oxidation product, dopaminequinone, canundergo follow-up ring closure reaction (Eq. 2), leading to leucodopaminechrome[37], which in

turn is oxidized to dopaminechrome (Eq. 3). The latter compound can polymerize to melanin-like compounds (Eq. 4) on the surface of the electrode and, thus, can inhibit the electron transferreaction[38]in the ring closure reaction (Eq. 2). It is required that the protonated side chain of

dopaminequinone move toward the quinone ring. But at the poly(DBA) modified electrode, the

high density of negatively charged groups in the film is likely to immobilize the chain or at least

suppress its mobility and, thus, prevent the reaction given byEq. (2)and, consequently, all of thefollow-up reactions.
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Fig. 6. Repetitive cyclic voltammograms of 1.0 104

M DA at poly(DBA) modifiedelectrode in 0.1 M phosphate buffer solution. Scan rate: 100 mV s

1.

Figure options

Scheme 1. Possible reaction procedure of DA on the electrode.

Figure options
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Determination of DA

The determination of DA concentration at the poly(DBA) modified electrode was performed

with cyclic voltammetry. The anodic peak current was linear to DA concentration in the rangesof 1.0 10

7to 4.0 10

5M and 4.0 10

5to 1.0 10

4M. The linear regression equations

were ip (10 A) = 0.59247 + 3.85979 C (10 M) (R = 0.99801) and ip (10 A) = 11.928 +0.9335 C (10 M) (R = 0.99212), respectively. The detection limit was 6.0 10

8M.

The relative standard deviation of 10 successive scans was 3.9% for 1.0 105

M DA, indicating

that the poly(DBA) modified electrode had excellent reproducibility. Furthermore, the stabilityof the modified electrode was investigated. The peak current retained 95.7% of its initial

response after storage in air for 2 weeks.

Analytical applications

The injections of DA were analyzed by the standard addition method. The results are shown in

Table 1. The recovery and relative standard deviation values were acceptable, showing that theproposed methods could be efficiently used for the determination of DA in injections.

Table 1. Determination of DA in injections (n = 8)

SampleContent (mg

ml1

)

Found (mg

ml1

)

RSD

(%)

Added (mg

ml1

)

Found (mg

ml1

)

Recovery

(%)

1 10 9.824 3.52 10 10.055 100.55

2 10 9.793 2.21 10 10.422 104.22

3 10 10.126 0.66 10 9.678 96.78

Table options

Conclusions

This study has indicated that the poly(DBA) film exhibits highly electrocatalytic activity to the

oxidation of DA. The modified electrode provides greater sensitivity and selectivity in thedetermination of DA. The interference of AA could be eliminated due to the very favorable

electrostatic interaction between the negatively charged poly(DBA) film and cationic species of

DA or anionic species of AA in phosphate buffer solution at pH 7.4. Moreover, the modified

electrode showed good reproducibility and stability. The proposed methods can be applied to the

detection of DA in the presence of excess AA in real samples.

Acknowledgments

This work was supported by the National Natural Science Foundation of China (20235010 and

20775088), the Foundation of State Key Laboratory of Electroanalytical Chemistry, Changchun

Institute of Applied Chemistry (CIAC, 2006002), and the President Foundation of GraduateUniversity of the Chinese Academy of Sciences (GUCAS).
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o Y.Z. Zhang, G.Y. Jin, Z.S. Yang, H. Zhaoo Determination of dopamine in the presence of ascorbic acid using a

poly(amidosulfonic acid) modified glassy carbon electrode

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[18]o H. Zhao, Y.Z. Zhang, Z.B. Yuano Study on the electrochemical behavior of dopamine with poly(sulfosalicylic acid)

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|

PDF (102 K)

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19.o [19]o H. Zhao, Y.Z. Zhang, Z.B. Yuano Electrochemical determination of dopamine using poly(2-picolinic acid) modified

glassy carbon electrode

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carbon electrode and separation of electrocatalytic responses for ascorbic acid and

dopamine oxidation
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