A systematic review on electrochemical sensors for the detection of acetaminophen

Ming Wei ^a, Yikai Yuan ^a, Dongsheng Chen ^a, Lin Pan ^c, Wenting Tong *^a and Wenbo Lu *^b
aKangda College of Nanjing Medical University, Lianyungang 222000, Jiangsu, China. E-mail: wttong@njmu.edu.cn
^bKey Laboratory of Magnetic Molecules and Magnetic Information Materials (Ministry of Education), School of Chemistry and Material Science, Shanxi Normal University, Taiyuan 030031, Shanxi, China. E-mail: luwb@sxnu.edu.cn
^cDepartment of Laboratory Medicine, Tianjin Peace District Obstetrics and Gynecology Hospital, Tianjin, 300020, China

First published on 19th August 2024

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Ming Wei

Ming Wei is currently an associate professor at Kangda College of Nanjing Medical University, China. He received his PhD at Shanxi Normal University (SNU) in 2022. He obtained his master's degree from Nanjing Normal University (NNU) in 2014. Currently, his research mainly focuses on the design and application of transition metal nanomaterials, including sensing, food safety and disease warning.

Wenting Tong

Wenting Tong is an experimentalist at the Department of Basic Medicine, Kangda College of Nanjing Medical University, China. She received her master's degree from Shanxi Normal University (SNU) in 2014. Her research focuses on the detection of disease markers.

Wenbo Lu

Wenbo Lu received his PhD from Southeast University (SEU), China in 2016. From 2019 to 2020, he worked as a visiting scholar at the University of Electronic Science and Technology of China. Currently, he is an associate professor at the School of Chemical and Materials Science, Shanxi Normal University, China. He is ranked among the World's Top 2% most-cited scientists 2023 by Stanford University. He has published over 130 articles and book chapters related to nanomaterials and sensors. His research interests include the design and fabrication of functional materials for electroanalytical chemistry and electrocatalysis.

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1. Introduction

The discovery of acetamide was the result of a medical serendipitous event. It is said that two doctors studying the effect of naphthalene on intestinal parasites mistakenly administered acetamide instead of naphthalene but noted its unique property and fever-reducing function in 1886.¹ Subsequently, a series of related drugs were synthesized, among which acetaminophen/paracetamol (AP) is the most representative drug.²

Modern pharmacological studies have shown that AP can inhibit the synthesis of prostaglandins produced by the central nervous system to achieve antipyretic and analgesic effects and is often used to treat colds, fever and pain.³ In general, an appropriate amount of AP can cure disease, but the side effects caused by the excessive use of AP cannot be ignored, which are caused by the toxic metabolite N-acetylbenzoquinoneimine; the side effects may include nausea, vomiting, eczema, anorexia, liver and kidney damage and protein degeneration.⁴ AP poisoning is clinically diagnosed when the level of AP in human plasma exceeds 2.0 × 10² μg mL⁻¹. The metabolic process of paracetamol in the human body is shown in Fig. 1. During its metabolism in vivo, AP is oxidized by cytochrome P450 to N-acetylbenzoquinoneimine, and then, acetylbenzoquinoneimine is decomposed into AP-CYS and AP-MERC. In addition, AP metabolism is accompanied with two biotransformation products: AP-GLUC and AP-SULF.⁵

AP has been globally accepted as an antipyretic and analgesic drug because of its reliable efficacy and few side effects. As a result, the prescription volume of AP is excessively large. For example, in the UK, the prescription volume of AP reached 403.11 tons in 2000.⁶ However, the extensive use of AP has caused a great threat to the ecological environment balance. To date, AP has been found in the natural environment in Asia, Europe and Africa, leading to a series of adverse effects on the survival of humans and plants.^7,8 In addition, wastewater containing AP is usually digested by chloride or oxide treatment. The chlorination process produces 11 chlorinated products, many of which are toxic.⁹

Therefore, the accurate and quantitative determination of AP concentration is of great significance for both medical diagnosis and environmental detection. Generally, AP concentration is determined using common detection methods, such as optical technology (spectrophotometry, fluorescence¹⁰ and chemiluminescence¹¹), chromatographic analysis (high performance liquid chromatography,¹² gas chromatography¹³ and thin layer chromatography¹⁴) and electrical technology.¹⁵ Compared with other methods, electrochemical detection can achieve accurate and rapid determination of the target without the need for sample pretreatment process and dependence on large instruments.¹⁶ In the electrochemical sensors' design process, the key point is the selection of the working electrode. A variety of nanomaterials has been involved in the design and preparation of AP electrochemical sensors, which is also the focus of this review. The purpose of this paper is to give a brief review of AP electrochemical sensors and provide a reference for the design of subsequent sensors.

2. Research status of AP electrochemical sensors and highlights of this review

By virtue of its inherent advantages, the electrochemical detection of AP has attracted the increasing attention of researchers, which is proved by the number of articles published.^17,18 In the database of Web of Science, the themes (paracetamol OR acetaminophen), electrochemical and (detection OR Analysis OR monitor OR sensor) were searched. The retrieval results (Fig. 2) show that during the decade from 2014 to 2023, the number of published articles basically shows an increasing trend year by year, and the number of articles published in 2022 was 2.42 times that in 2014, proving that AP electrochemical detection is favored by more researchers.

The visualization software VOS viewer is a powerful tool for the further analysis of AP electrochemical sensor articles over the past decade. As shown in Fig. 3, in the clustering diagram, the top 15 high-frequency words (the number in parentheses is the total link strength) are acetaminophen (6720), paracetamol (4882), sensor (3440), ascorbic-acid (3324), electrochemical sensor (3114), dopamine (3073), nanoparticles (3070), voltammetric determination (2493), uric acid (2140), nanocomposite (1961), nanotubes (1662), graphene (1500), glassy-carbon electrode (1491), composite (1419) and electrode (1379). It is more certain that AP is generally mixed with ascorbic acid, dopamine, uric acid and so on. The detection materials are mostly graphene composite materials, and the electrochemical technology is mostly voltammetry.

To date, there have been some reviews on AP electrochemical detection, each with its own characteristics. Forbes et al. from the University of Pretoria summarized the analysis and detection techniques of AP from a macro-perspective, including electrochemical methods, chromatography-mass spectrometry, capillary zone electrophoresis and spectroscopy.¹⁹ In the section of electrochemical analysis, AP sensors are classified according to the electrochemical techniques, but the overview is not specific enough.

In reviews on the electrochemical detection of drugs and water environmental pollutants, traces of AP can also be found. Unfortunately, AP electrochemical detection is only a small part of these reviews, which makes it difficult for readers to fully grasp the detection status of AP. For example, Sivaranjanee et al., from St. Joseph's College of Engineering, systematically collated the literature on the electrochemical detection of emerging contaminants in the water environment, including drugs, endocrine disruptors and personal care products.²⁰ Similarly, Jiang et al., from Zhejiang Guangsha Vocational and Technical University of Construction, reviewed the research progress of drug electrochemical detection based on graphene composites, also involving AP.²¹

AP electrochemical detection reviews have also been reported, among which carbon-based materials are the central theme.^22,23 In addition, the electrochemical detection of paracetamol based on ionic liquids at room temperature has also been systematically reviewed.²⁴ Boumya et al., from Sultan Moulay Slimane University, and Tasić et al., from the University of Belgrade, focused on the modification of carbon-based electrodes and pencil graphite electrodes, respectively, and their progress in the electrochemical detection of AP is further introduced.^25,26 However, a mere overview of carbon-based electrodes is not enough for readers who want to fully understand the current state of AP electrochemical detection.

In this review, the literature on AP electrochemical detection was analyzed by metrology, and the research progress of enzyme-free and enzyme-based AP electrochemical sensors was systematically summarized. This review gives a comprehensive introduction to the progress of AP electrochemical research, which attempts to narrate an elegant story about the electrochemical detection of AP for readers.

3. Electrochemical principles and technology of AP detection

In the process of electrochemical detection, the response current is generated due to the electron transfer between the electrode and AP, and the response current is positively correlated with the AP concentration, which is also the quantitative basis for the electrochemical detection of AP. The AP detection mechanism will vary according to the monitoring environment. Fig. 4 shows the possible electrochemical detection mechanisms of AP under strong acid, alkaline, and intermediate conditions discussed by Chen's group.²⁷ Our group has made some modifications on this basis.

In acidic medium, NAPOI is first oxidized by air and loses two electrons and two protons to give intermediate A; A gains a proton from the medium to form enamine positive ion B and is attacked by a water molecule, which loses a proton to form intermediate C; C forms a six-membered cyclic transition state, which sheds an acetamide molecule to give the final product, benzoquinone D.

In alkaline medium, NAPOI is first oxidized by air to give intermediate A; then, a hydroxide ion in the medium attacks A and A gains a proton from water to give intermediate E, which then rearranges to F, which continues to be oxidized by air to give G. Just like intermediate A, G undergoes affinity addition, rearrangement, and oxidation to give the final product J.

In a neutral medium, one NAPOI molecule is oxidized to intermediate A, another NAPOI molecule loses a proton to obtain the nucleophilic reagent K, and the two molecules of the intermediate undergo a nucleophilic addition reaction to obtain the dimer L, which is rearranged to the final product M.

Electrochemical analysis and testing mainly rely on electrochemical workstations using a three-electrode system, which includes a working electrode, reference electrode and auxiliary electrode (Fig. 5a and b). Specifically, the three-electrode system contains two loops, one is the polarization circuit and the other is the measurement circuit. The polarization circuit is composed of a power source, a working electrode and an auxiliary electrode, which will pass a higher current during the experiment. The measurement circuit is composed of a working electrode and a reference electrode so as to realize the determination of the relevant parameters of the working electrode. In this process, only a very small current (<10⁻⁷ A) passes through the measurement circuit, and the circuit diagram is shown in Fig. 5c.

To date, electrochemical analysis has made a rapid progress, and various new methods and techniques of electroanalysis have emerged, as exhibited in Fig. 5d. The electrochemical methods currently employed to monitor the concentration of AP include cyclic voltammetry (CV), linear sweep voltammetry (LSV), differential pulse voltammetry (DPV), square wave voltammetry (SWV), adsorptive stripping voltammetry (AdsSV) and amperometric i–t curve (i–t).

In CVs, the working potential is scanned from the initial potential to the termination point and then back to the original potential, completing the process. The CV method can not only help researchers to determine the concentration of the substance to be measured but also explore the kinetic details of the electrode reaction. In LSV technology, the working potential is positively correlated with the scan rate, and the analysis purpose is achieved according to the recorded current–potential curves. According to the Randles–Sevcik equation, the peak current is proportional to the target concentration and is related to the scan rate.²⁸ DPV is an electrochemical trace determination method. It needs to sample the current twice, using the current difference to plot the potential, so as to obtain the target concentration. SWV is a large amplitude analysis method, which has the characteristics of fast scanning speed and short analysis time. All in all, in the practical analysis of AP electrochemistry, the DPV method is more popular than the CV method because of its high sensitivity and adaptability to complex sample analysis tasks.¹⁹

4. The construction of AP electrochemical sensors

The emergence of nanomaterials endows electroanalytical chemistry with a reliable future. Generally speaking, the enhancement effect of nanomaterials on the electrode is reflected in the following aspects: (I) increasing the electrode surface area. Porous or multi-dimensional nanomaterials can increase the surface area of the electrode and further improve the response time and stability of the electrode by providing more reaction sites. (II) Increasing the sensitivity and selectivity. Specific modified nanomaterials can achieve sensitivity detection and the selective recognition of target molecules, which improves the accuracy of the electrochemical sensor. (III) Enhancing the electrocatalytic activity. The inherent catalytic properties of nanomaterials can reduce the activation energy of chemical reactions and increase the electrochemical reaction rate. In brief, the variety of nanomaterials provides unlimited possibilities for the construction of AP electrochemical sensors. In the following discussion, AP electrochemical sensors will be discussed systematically from the perspective of nanomaterials.

4.1 AP electrochemical sensors fabricated by precious metals

In the periodic table, precious metals generally refer to gold, silver and platinum group metals. With the inherent excellent catalytic activity, good chemical stability and promising biocompatibility, nano-sized precious metals have been widely employed in electrochemical sensors. They play an important role in the quantitative detection of AP, either alone, combined or combined with other materials. From the mechanism point of view, noble metals can accelerate the electron transfer between AP and the electrode surface, while greatly improving the response current, so as to improve the analytical performance of AP. Nanoscale precious metal materials have a large Gibbs free energy and aggregation tendency, which cannot be ignored; thus, suitable supporting materials are required, which is also the reason why precious metals often appear in the report at the same time as carbon-based materials.

Haghshenas and collaborators constructed an electrochemical sensor by immobilizing Au nanoparticles onto the surface of magnetic Fe₃O₄ particles and quantitatively measuring AP using magnetoelectric electrodes. The AP electrochemical sensor had a linear range of 1.0 × 10⁻¹–70 μM and a detection limit as low as 4.5 × 10⁻² μM.²⁹ Kumar et al. synthesized curcumin-functionalized silver nanoparticles employing a green synthesis route, which effectively prevented the coagulation of silver nanoparticles. The linear range of AP electrochemical sensor based on the nanomaterial was 5.9 × 10⁻⁷–3.4 × 10⁻⁴ M, and the detection limit was as low as 2.9 × 10⁻¹ μM.³⁰ Based on the synergistic effect between materials, Rajamani et al. constructed an AP electrochemical sensor based on Pt/CeO₂@Cu₂O carbon-based nanocomposites (Fig. 6a). The as-prepared nanotubes (Fig. 6b) electrochemical sensor showed good performance with a linear range as low as 9.1 × 10⁻² μM, as shown in Fig. 6c.³¹ In order to prevent the aggregation of precious metal nanoparticles, Wu et al. successfully constructed an AP electrochemical sensor relying on precious metal Pd and multi-layer carbon nanotubes (Fig. 6d). The linear range of the electrochemical sensor was 5.0 × 10⁻¹–100 μM, and the detection limit was 1.3 × 10⁻¹ μM with a reliable selectivity (Fig. 6e and f).⁵⁷ In addition to the usage of single metal alone, the combination of multiple precious metals to detect AP has also been reported, which takes advantage of the synergy between bimetals. Considering that Au and Pd can effectively improve the reproducibility, stability and electrocatalytic activity of the working electrode, Qu and his collaborators successfully synthesized CS/Au/Pd/rGO for the electrochemical determination of AP, as shown in Fig. 6g.³² The sensor demonstrated good performance with a detection limit as low as 3.0 × 10⁻¹ μM and can be used for the determination of AP in actual water samples. Furthermore, defect engineering has also been applied to AP detection based on polymetallic nanomaterials. As illustrated in Fig. 6h, Jeon et al. designed an AP electrochemical sensor based on the nano-composite material Pd@α-MnO₂ with a detection limit as low as 5.9 × 10⁻² μM.³³Table 1 lists the performance of AP electrochemical sensors based on precious metals.

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4.2 AP electrochemical sensors fabricated by transition metals

Transition metals, usually referred to as d-block elements, are located between the s-block and p-block in the periodic table of elements. The valence electron configuration is (n−1)d¹⁻¹⁰ns¹⁻². Compared with precious metals, transition metals possess the merits of abundant reserves, perfect stability and superior activity, and are the focus of catalyst development. In the design of AP electrochemical sensors, cobalt, nickel, and copper are excellent representatives, specifically.

Cobalt, located in group VIII of the periodic table, is a typical transition element with high catalytic activity. The d orbital of cobalt is not filled; thus, it has a variety of valence states, usually showing +2 and +3. Correlational studies have shown that cobalt-based materials have great potential in the fields of electrochemical sensing and electrocatalysis. In the construction of AP electrochemical sensors based on cobalt-based materials, the performance of the sensors is often improved by adjusting the morphology of catalysts and combining with other materials. When Co₃O₄ is elegantly combined with a hollow carbon structure having appropriate pore architectures, this composite nanostructure shows good detection ability for AP. As shown in Fig. 7a, Wang et al. constructed an AP electrochemical sensor based on Co/Co₃O₄@HNCP. Thanks to the synergistic effect with hollow carbon polyhedrons, the detection limit of the sensor was as low as 8.3 × 10⁻³ μM at pH 6.0 (Fig. 7b).⁶¹ Similarly, as demonstrated in Fig. 7c, Duraisamy et al. fabricated the AP electrochemical sensor based on Co₃O₄@NHCS. The sensor had a linear range of 1.0–2.0 × 10² and 1.0 × 10³–8.0 × 10³ μM (Fig. 7d).⁶² At the same time, the AP sensor based on the intermetallic synergism also uses the design of multi-metallic cobalt-based oxides. Sun and his collaborators constructed an electrochemical sensor based on S-CTFs@NiCo₂O₄ to detect AP with a detection limit as low as 1.8 × 10⁻¹ μM.⁶³ Something similar to Co-La oxides/CNF/GCE has also been reported.⁶⁴ In addition, cobalt phthalocyanine cannot be ignored in the field of AP electrochemical detection. Cobalt phthalocyanine is often used as an electrode modifier, which can easily convert the valence states of cobalt during the reaction.⁶⁵ Luhana et al. employed the CE-Ergo/polyCoTAPc as the working electrode to achieve the goal of quantitative AP determination with the detection limit as low as 1.0 × 10⁻¹ μM.⁶⁶ The performance of the reported cobalt-based AP electrochemical sensors is listed in Table 2.

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Nickel, which is similar to cobalt, is also popular in building AP electrochemical sensors. Nickel-based materials have abundant reserves, low cost and excellent catalytic performance. Compared with cobalt-based materials, nickel-based materials are more diverse, including elemental substances, oxides, hydroxides, and phosphates, which are used in the design of AP sensors. Wang et al. designed and synthesized carbon-coated nickel nanoparticles for the quantitative determination of AP. The linear range of the sensor was 7.8–1.1 μM and the detection limit was 2.3 μM.⁸⁸ In order to give full play to the synergistic effect between metals, Maduraiveeran et al. and Dou et al. constructed the electrochemical sensor based on Ti/AuNi and CuNi/rGO to realize the detection of AP, respectively^89,90 Furthermore, Niu et al. prepared Co₁Ni₁ @CN-700 composites with bimetallic CoNi-MOF as raw materials to achieve the goal of AP monitoring (Fig. 8a). Fig. 8b shows that the detection limit of the AP electrochemical sensor is as low as 3.8 × 10⁻³ μM.⁸⁰ NiO nanoparticles have high theoretical capacitance and large surface area. Annadurai built an AP electrochemical sensor based on NiO/GCE with a detection limit of 2.3 × 10⁻¹ μM.⁹¹ Similarly, due to the synergistic effect, bimetallic oxides such as NiFe₂O₄ are also used for the electrochemical determination of AP.⁹² Babaei et al. constructed an AP electrochemical sensor based on Ni(OH)₂ and multi-walled carbon nanotube with a detection limit of 1.0 × 10⁻² μM, indicating that hydroxides also have the potential to detect AP.⁹³ Our group further expanded the range of nickel-based materials in AP detection, i.e., for the first time, Ni₂P was employed in AP electrochemical detection (Fig. 8c). At the same time, the potential sites of the reaction were determined by discussing the electrostatic potential of AP (Fig. 8d). The linear range of the electrochemical sensor was 5.0 × 10⁻¹–4.5 × 10³ μM, and the detection limit was 1.1 × 10⁻¹ μM.¹⁵ The performance of the reported nickel-based AP electrochemical sensors is listed in Table 3.

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Copper-based nanomaterials, with good conductivity and abundant reserves, are also used in the preparation of AP electrochemical sensors. The copper-based materials reported for AP electrochemical sensing include elemental, oxide, and Cu-MOF. Brahman et al. electrodeposited copper nanoparticles on modified CPE to complete the construction of the CuNPs/C₆₀/MWCNTs/CPE composite. The AP electrochemical sensor based on this nanomaterial has a detection limit as low as 7.3 × 10⁻⁵ μM.¹¹⁴ Li's group prepared a series of AP electrochemical sensors based on copper-based materials, including CuX (CuO, Cu₂O and CuS)/g-C₃N₄. CuS/g-C₃N₄ showed optimum performance in the comparison experiment with a detection limit of 2.6 × 10⁻¹ μM due to its higher catalytic rate constant.¹¹⁵ In addition to single metals, bimetallic or trimetallic copper-based nanomaterials are also employed in the design of AP electrochemical sensors, considering the synergistic effect.^109,116 As can be seen from Fig. 9a, the combination of Cu-based materials and MOF is another path for AP electrochemical construction. Manoj et al. constructed Cu-MOF/HNTs/rGO nanomaterials to achieve the electrochemical determination of AP with a linear range of 5.0 × 10⁻¹–2.5 × 10² μM and a detection limit of 1.5 × 10⁻¹ μM at pH 7.0 (Fig. 9b–d).¹¹⁷ The performance of the reported copper-based AP electrochemical sensors is listed in Table 4.

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In addition to cobalt, nickel, and copper, other metals are more or less involved in the preparation of AP electrochemical sensors. Ferrocene is the most representative structure of iron-based materials, which are used to label proteins or aptamers while amplifying the response current.^142–144 Movlaee et al. achieved the quantitative determination of AP with an electrochemical sensor based on ferrocene and graphene composites with the linear range of 1.0–1.5 × 10² μM and a detection limit as low as 5.0 × 10⁻¹ μM.¹⁴⁵ In addition to ferrocene, iron oxides are also used in the design of AP electrochemical sensors. Fe₃O₄ with an inverse spinel structure can promote electron transfer and improve the conductivity.¹⁴⁶ Guo's group successfully prepared Fe₃O₄/N/C composites by combining Fe₃O₄ nanoparticles with MOF and multi-walled carbon nanotubes, as shown in Fig. 10a and b. The as-prepared AP sensor showed superior performance, a linear range of 5.0 × 10⁻¹–1.4 × 10³ μM and a detection limit as low as 1.4 × 10⁻¹ μM (Fig. 10c and d).¹⁴⁷ Similar to iron oxides, TiO₂ is a typical titanium-based material, which has good biocompatibility and chemical stability and is often used in the design of AP electrochemical sensors. Li's group prepared H-C/N@TiO₂ by a simple alcoholic and hydrothermal method and applied the nanomaterials for the electrochemical determination of AP. The linear range of the sensor is 3.0 × 10⁻¹–50 μM, and the detection limit is as low as 5.0 × 10⁻² μM.¹⁴⁸ In the field of zinc-based materials, ZnO has the advantages of simple preparation, high specific surface area and superior stability, which is widely employed in the construction of AP electrochemical sensors.^149,150 Liu et al. synthesized ZnO-MoO₃-C composite material based on MoO₃/ZnO and mushroom carbon for the electrochemical determination of AP (Fig. 10e and f). In the presence of dopamine, the linear range of the sensor is 2.5–2.0 × 10³ μM, and the detection limit is as low as 1.1 μM, as is shown in Fig. 10g.¹⁵¹ In addition to the above metals, AP electrochemical sensors constructed with nanomaterials containing elements such as Y,¹⁵² Zr¹⁵³ and Mo¹⁵⁴ have all been reported, as shown in Table 5.

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4.3 AP electrochemical sensor fabricated by non-metallic nanomaterials

Carbon-based materials have outstanding advantages, low cost, abundant reserves and stable performance; thus, it is necessary to take carbon-based materials as the protagonist in the discussion of AP electrochemical sensors involving non-metallic materials. More importantly, carbon-based materials have rich morphologic features, such as zero-dimensional material carbon points, one-dimensional material carbon nanotubes, two-dimensional material graphene, and three-dimensional material carbon nanotubes, which is one of the unique advantages of carbon-based materials.¹⁷⁸

Graphene is a honeycomb plane structure composed of sp² hybrid carbon atoms, which has a large specific surface area, strong electron transport performance and high electrochemical activity.¹⁷⁹ From the perspective of microstructure, the van der Waals force between different planes leads to the aggregation of graphene, which has a great influence on its electrochemical performance. It is usually overcome by introducing other functional groups. Therefore, graphene often appears in the form of graphene oxide and reduced graphene oxide.¹⁸⁰ Huang et al. employed poly(3,4-ethylenedioxythiophene) as a conductive bridge to form a composite material rGO-PEDOT with rGO (Fig. 11a). In consideration of the synergistic effect between the materials, the resulting AP electrochemical sensor exhibits convincing performance with a linear range of 1–35 μM, a detection limit as low as 4.0 × 10⁻¹ μM, and good selectivity (Fig. 11b and c).¹⁸¹ Heteroatom doping is another modification path for carbon-based materials. Zhang et al. completed the synthesis of P-rGO nanomaterials by doping phosphorus in rGO. The AP electrochemical sensor designed by this method has a detection limit as low as 3.6 × 10⁻¹ μM, which can be used for the quantitative analysis of AP in a commercial tablet.¹⁸²

Carbon nanotubes are divided into single-walled carbon nanotubes (SWCNT) and multi-walled carbon nanotubes (MWCNT), both of which have network-type spatial structure with excellent conductivity and large specific surface area. Chen's group combined MWCNT with GO to synthesize MWCNT-GO composites, which realized the simultaneous determination of dopamine and AP (Fig. 11d). Due to the combination of the high charge density of GO and the advantages of MWCNT, the linear range of the constructed AP electrochemical sensor is between 5.0 × 10⁻¹ μM and 4.0 × 10², μM, and the detection limit is as low as 5.0 × 10⁻² μM (Fig. 11e and f).¹⁸³

With the advancement of science and technology, new carbon-based materials have been gradually discovered, and the graphitic carbon nitride (g-C₃N₄) is a typical representative.¹⁸⁴ The possible building blocks of g-C₃N₄ are shown in Fig. 11g. Liu et al. convincingly completed the electrochemical determination of AP by g-C₃N₄, which was prepared by melamine pyrolysis. The linear range of the as-prepared sensor was 1.7–2.0 × 10³ μM, and the detection limit was 1.5 × 10⁻¹ μM (Fig. 11h and i).¹⁸⁵

In addition to the carbon-based materials as the main part involved in the construction of AP electrochemical sensors, other non-metallic materials have also been reported. It should be noted that electropolymerization technique has been employed for these materials to participate in the construction of AP electrochemical sensors. Sun et al. applied the electropolymerization technology to prepare a new coccine film on a carbon paste electrode to achieve the quantitative determination of AP. The linear range of the electrochemical sensor was 1.5–1.2 × 10² μM, and the detection limit was 3.0 × 10⁻¹ μM.¹⁸⁶ Raoof's group employed luteolin as an electron transfer medium to construct an electrochemical sensor based on Lt/fMWCNT/MGCE by strong combination with multilayer carbon nanotubes. The linear range of the sensor is 9.0 × 10⁻¹–80 μM, and the detection limit is as low as 7.8 × 10⁻¹ μM.¹⁸⁷ Significantly, molecular imprinting technology has strong recognition ability for specific template molecules.¹⁸⁸ Dai et al. constructed an AP electrochemical sensor by the electrodeposition of Prussian blue and molecularly-imprinted polypyrrole on a GCE electrode. The detection limit of the prepared AP electrochemical sensor was unexpectedly as low as 5.3 × 10⁻⁴ μM.¹⁸⁹ The performance of some related non-metallic AP electrochemical sensors is shown in Table 6.

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4.4 Enzymatic AP biosensors

Enzymatic sensor is an important component of electrochemical sensors.²¹⁵ All of the AP electrochemical sensors mentioned above are non-enzymatic electrochemical sensors. Although enzymatic-based electrochemical sensors are rarely reported, they are also an important part of AP electrochemical sensors. From the perspective of the source of enzymes, it can be divided into pure enzymes and plant tissues, which are involved in the enzyme biosensors.

The first enzymatic AP biosensor dates back to 1991 when Vaughan et al. constructed the first corresponding sensor using aryl acylamidase (EC 3.5.1.13), which achieved the purpose of determining the AP concentration in blood. However, the lack of commercialization of this enzyme is a bottleneck.²¹⁶ Then, the polyphenol oxidase extracted from plant tissues immediately boarded the stage. Orlando et al. constructed an enzymatic AP biosensor based on polyphenol oxidase extracted from avocado tissue, with a detection limit of 8.8 μM.²¹⁷ Garcia et al. extracted polyphenol oxidase from eggplant, and the detection limit of the sensor was as low as 5.0 μM.²¹⁸ Aliabadi et al. used hydrogel as the absorbent polymeric matrix was combined with polyphenol oxidase extracted from banana to construct the AP biosensor, and the detection limit was successfully reduced to 1.6 μM.²¹⁹ The target enzyme of Valero et al.'s study was horseradish peroxidase (HRP), which was combined with polyacrylamide microparticles to construct the AP biosensor, and the detection limit of the sensor was 3.1 μM.²²⁰ At the same time, based on Valero's previous work, Frangu et al. studied the AP enzyme-based sensor containing tyrosinase, and the detection limit was even reduced to 1.1 μM.^221,222

5. Influencing factors of AP electrochemical sensors

5.1 Supporting electrolyte

Usually, to maintain the pH value throughout the electrochemical experiment, the buffer solution serves as the supporting electrolyte in the electrochemical sensor. In the design of AP electrochemical sensors, the common buffer solutions include phosphate buffer (PB) system, Britton–Robinson (B–R) buffer solution, and HAc-NaAc (ABS), which should be paid attention to for reasonable selection in the process. As a very popular buffer, the PB buffer system is usually composed of dihydrogen phosphate and monohydrogen phosphate. A certain amount of KCl or NaCl is usually added to achieve a certain ionic strength. Wang and co-researchers selected PBS as the supporting electrolyte and constructed an AP electrochemical sensor based on Co/Co₃O₄ and hollow nanoporous carbon polyhedrons with a detection limit as low as 8.3 × 10⁻³ μM.⁶¹ Compared with PB buffer, the B–R buffer system possesses a wider buffer range, which is also welcomed by laboratories. The AP electrochemical sensor built by Mahmoud et al. based on BiO-SPEs employed B–R buffer solution as the electrolyte.²²³ In addition, few people chose ABS as the buffer solution in the construction of the electrochemical sensor, for example, Li et al. chose ABS (pH 5.5) as the supporting electrolyte, which may be limited because of the narrow buffer range between 3.75 and 5.75.²²⁴

There is an important issue that cannot be ignored, namely, the matching of the electrode material to the supporting electrolyte. While employing zeolite-modified electrodes to detect AP, Sharifian et al. chose NaCl as the supporting electrolyte, which is due to consideration of ion exchange between the electrode material and the supporting electrolyte.¹⁵⁸ Similarly, in the design of the AP electrochemical sensor with Ag-based materials, Bhat and collaborators selected citrate buffer solutions as the supporting electrolyte because the citrate system had the lowest reactivity with Ag nanoparticles.⁴⁸ In addition, the H₂SO₄/Na₂SO₄ buffer system has also been reported.²²⁵

5.2 Interfering substances

Selective analysis, also known as interference research, is an important parameter in the design of electrochemical sensors. In the construction of AP electrochemical sensors, the selection of interfering substances generally follows two principles, one is the similarity of chemical structure and oxidation potential, and the other is the specific use environment.

While studying the interfering substances, Jin and collaborators mainly considered the factors of structure and oxidation potential. Among them, 4-nitroaniline, phenacetin, and 4′-chloroacetanilide were selected on the basis of their similar structure, while glucose, rutin and uric acid were selected on the basis of their similar oxidation potential.⁴⁰ Generally speaking, AP detection is needed in two scenarios, including medical and environmental monitoring. Guo et al. mainly considered the interference of ascorbic acid, uric acid and dopamine in biological samples, and various interference ions and biological small molecules, such as Na⁺, K⁺, Mg²⁺, Ca²⁺, L-proline and L-threonine, were also considered.⁹⁵ Compared with the influence of interfering substances under physiological conditions, there are few related reports on environmental interferents. At present, bisphenol A, p-nitrophenol, Cd²⁺ and Fe³⁺ are mainly selected as interferents.^226,227 From a quantitative point of view, the selectivity can be evaluated using the following formula.

K = (response current)AP/(response current)interfering molecule

If the value of K is much larger than 1, it indicates that the electrochemical sensor has outstanding selectivity.

6. Simultaneous determination of AP and other targets

In the design of electrochemical sensors, identifying multiple targets simultaneously is often more popular. In the reported literature on AP electrochemical sensors, multiple substances can be determined simultaneously using AP. The principle for selecting targets for simultaneous detection is the same as that for interference experiments: one is structural similarity, and the other is drugs that may appear in the same clinical prescription. The intermediates in AP preparation or metabolism in vivo also should also be considered. As AP, dopamine and tryptophan are nitrogen aromatic compounds with similar structures, Liu et al. constructed an electrochemical sensing platform using NiO-CuO/GR to achieve the quantitative determination of the above three substances.⁹⁴ It has been clinically proved that AP, tramadol and caffeine are superior to single drugs in relieving pain and reducing side effects. Therefore, it is of certain significance to realize the simultaneous determination of these three substances. Chitravathi and Munichandraiah employed poly(Nile blue)-modified GCE to achieve the expected target.²²⁸ Considering the metabolic relationship of AP, Safavi et al. determined the concentration of AP and its intermediate p-aminophenol.²²⁹ In addition to the substances mentioned above, isoniazid,²³⁰ ofloxacin,²³¹ cefazolin and dexamethasone¹⁹² were also measured at the same time as AP, as shown in Fig. 12. In general, no matter which substances are monitored at the same time, they should have a significantly different peak potential from AP under the same experimental conditions.

7. Summary and prospectives

In this review, the relevant literature on the electrochemical detection of AP in the past 10 years was quantitatively analyzed, and the development history of AP, the principle, technology, nanomaterials and performance influencing factors of electrochemical sensors were systematically summarized. In the design and preparation of AP electrochemical sensors, various nanomaterials including precious metals, transition metals, non-metals, and enzymatic biosensors are involved, which provides unlimited possibilities for the selection of working electrodes for AP electrochemical detection. Generally, in the process of AP sensor design, it is necessary to increase the catalytic site or improve the intrinsic electrocatalytic activity of the nanomaterial itself as much as possible to achieve the purpose of reducing the activation energy of the electrode reaction, which can usually be achieved by synergistic effects between materials or changing the topological structure of nanomaterials.

However, some prominent problems cannot be ignored. At present, most AP electrochemical sensors are still in the laboratory stage, even if it is claimed that they can be employed for the detection of actual samples. As mentioned in the article, the quantitative determination of AP is mainly required in health monitoring and environmental protection, which have certain differences in the requirements of AP electrochemical sensors. In the field of health monitoring, AP electrochemical sensors should be non-invasive and wearable, while in the field of environmental detection, they should be portable. As more and more researchers join the field of electrical analysis of AP, it is reasonable to believe that the electrochemical detection of medicine represented by AP will usher in its own era.

Data availability

No primary research results, software or code have been included and no new data were generated or analysed as part of this review.

Author contributions

Ming Wei: original draft, writing – review & editing; Yikai Yuan: data curation; Dongsheng Chen: data curation; Lin Pan: formal analysis, visualization; Wenting Tong: data curation, funding acquisition, project administration; WenBo Lu: supervision, writing – review & editing, resource and investigation.

Conflicts of interest

There are no conflicts to declare.

Acknowledgements

This work was supported by the Qing Lan Project in Jiangsu Province, Ju Xian Ji Hua of Kangda College of Nanjing Medical University; Scientific Research Innovation Team Project of Kangda College of Nanjing Medical University (KD2022KYCXTD002), Scientific Research Talents Training Program of Kangda College of Nanjing Medical University (KD2021KYRC013), the Science Research and Development Foundation of Kangda College of Nanjing Medical University (KD2022KYJJZD001 and KD2022KYJJZD054).

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