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Colorimetric and Fluorescent Probes Based on the Oxidation of o-Phenylenediamine for the Detection of Bio-Molecules

Liqing Li , Minghao Zheng , Dandan Jiang , Shuxin Cao , Kunming Liu , Jinbiao Liu

Progress in Chemistry ›› 2022, Vol. 34 ›› Issue (8) : 1815 -1830.

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Progress in Chemistry ›› 2022, Vol. 34 ›› Issue (8) : 1815-1830 DOI: 10.7536/PC210927
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Colorimetric and Fluorescent Probes Based on the Oxidation of o-Phenylenediamine for the Detection of Bio-Molecules
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Abstract

O-phenylenediamine (OPD) can be easily oxidized by a variety of oxidants to form yellow fluorescent substance 2, 3-diaminophenazine (OPDox), and the unique responding mechanism provides a principle in the design of reaction-based colorimetric/fluorescent probes. Up to now, colorimetric and fluorescent probes based on the OPD oxidative reactions have been widely applied in the detection of metal ions and organic molecules. In recent years, these probes have attracted much attention in the recognition of bio-molecules in cells and tissues due to their high sensitivity, fast response speed and strong anti-interference ability. This review summarizes the development of colorimetric and fluorescent probes based on the OPD oxidative reactions in the detection of important bio-molecules such as biothiols, reactive oxygen species, uric acid, enzyme, antigen and so on. We further make an in-depth perspectives on the application and development prospect of the probes.

Contents

1 Introduction

2 Detection of small bio-molecules

2.1 Biological thiols

2.2 Reactive oxygen species

2.3 Purine and its metabolites

2.4 Other small bio-molecules

3 Detection of biomacromolecules

3.1 Enzyme

3.2 Antigens

3.3 Bacteria and viruses

3.4 Other biomacromolecules

4 Conclusion and outlook

Graphical abstract

Keywords

o-phenylenediamine / colorimetric/fluorescent probe / oxidative reaction / bio-molecules / recognition

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Liqing Li, Minghao Zheng, Dandan Jiang, Shuxin Cao, Kunming Liu, Jinbiao Liu. Colorimetric and Fluorescent Probes Based on the Oxidation of o-Phenylenediamine for the Detection of Bio-Molecules. Progress in Chemistry, 2022, 34(8): 1815-1830 DOI:10.7536/PC210927

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1 Introduction

Biomolecules play an important role in affecting human life and health[1⇓~3]. For example, highly reactive oxygen species (hROS) and biological thiols are important cell signaling molecules in human body, enzymes are essential catalysts for cell metabolism, antigens are important biomarkers for auxiliary diagnosis and early warning of diseases, and bacteria and viruses are the main causes of human diseases. Therefore, the development of biomolecular detection methods is of great significance for the study of physiological mechanisms and clinical diagnosis. Up to now, a variety of biomolecular analysis techniques have been developed, such as electrochemical method, Photoelectrochemical method, liquid chromatography (HPLC), surface enhanced Raman spectroscopy and so on[4,5][6][7][8]. However, due to the biocompatibility and instrument characteristics, the above analysis methods are difficult to achieve in situ real-time detection of intracellular biomolecules[9].
Since Minta et al. First synthesized the calcium ion fluorescent probe in 1989, the fluorescent probe technology has been widely used in the detection of various cations, anions and small organic molecules, and has shown the advantages of high sensitivity, good selectivity, fast response, simple operation and so on[10][11][12][13]. Among them, the design principle of reactive fluorescent probes is based on the specific chemical reaction between the probe recognition group and the detection object, so they have excellent selectivity and anti-interference ability, and are suitable for in-situ detection of analytes in complex environments[14]. In recent years, reactive fluorescent probes for biomolecular detection have developed rapidly, providing a powerful tool for in-depth understanding of interactions in biological systems.
As an important organic raw material, o-phenylenediamine (OPD) is easily oxidized by a variety of oxidants such as H2O2, Cu2+, Hg2+, etc., resulting in the formation of a strong yellow fluorescent compound, 2,3-diaminophenazine (OPDox). Based on this unique colorimetric/fluorescent response, a series of colorimetric/fluorescent sensors have been developed for the detection of metal ions and small organic molecules, and the related research work has been summarized in our group[15]. Because of its high sensitivity, fast response and outstanding anti-interference ability, this kind of fluorescent probe has also been tried to be applied to the recognition of biomolecules in cells, tissues and living bodies in recent years. In this paper, the research progress of colorimetric/fluorescent probes based on OPD oxidation reaction in the recognition of small biomolecules and biomacromolecules from 2014 to 2021 is reviewed from the recognition principle and detection effect, and the application problems and development prospects of these probes are reviewed, so as to provide a reference for the design of efficient and reasonable OPD fluorescent probes.

2 Detection of Small Biomolecules by Colorimetric/Fluorescent Probes Based on OPD Oxidation Reaction

Small biomolecules, such as biothiols, reactive oxygen species, and purines, are closely related to cellular signal transduction, neuroregulation, and energy supply, and their concentration imbalance will lead to cancer, liver injury, and other diseases.Therefore, it is of great significance to achieve in situ detection of small biomolecules for the study of pathological mechanisms[16]. Due to the complex microenvironment of small biomolecules and the coexistence of many interfering substances, it brings great challenges to accurate detection. The advantages of colorimetric/fluorescent probes based on OPD oxidation reaction in specific recognition and anti-interference ability are helpful to overcome this difficulty and achieve in situ detection in cells.

2.1 Biothiol

Biological thiols such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) play an irreplaceable role in protein synthesis and cell signal translation, and the imbalance of their concentration levels will lead to arthritis, liver injury, hematopoietic disorders and AIDS[17]. Therefore, the detection of biological thiols in organisms is very important. In 2020, Chen Dugang et al. Reviewed some thiol fluorescent probes with excellent performance and emitting red or near-infrared light signals, represented by rhodamines, dipyrrole fluoroborons, cyanines, natural pigments, donor-acceptor conjugated compounds and aggregation-induced luminescence compounds[18]. However, the thiol fluorescent probes based on OPD oxidation reaction have not been involved. Therefore, our research group supplemented the biological thiol probes, hoping to provide more ideas for the detection of biological thiols.
In 2018, Wang Hua et al. First realized the detection of biological thiols by fluorescent probes based on OPD oxidation reaction (Fig. 1)[19]. Taking advantage of the oxidizability of Ag+, OPD will be rapidly converted to strongly fluorescent OPDox. When biological thiols exist, Ag+ will preferentially complex with them, thus losing the oxidation ability and failing to achieve the oxidation reaction of OPD, resulting in the attenuation of fluorescence intensity. Based on this fluorescence "on-off" strategy, the Ag+-OPD recognition system achieved the linear detection of Cys, Hcy and GSH in the range of 0. 5-30. 0 μM, 1.0-45. 0 μM and 0. 5-40. 0 μM, respectively, with the lowest detection limit (LOD) of 110 nM, 200 nM and 150 nM. Compared with other detection methods, the fluorescent probe has a short response time (10 min) and strong anti-interference ability to common amino acids, and has been successfully used for the detection of biological thiols in human serum[20]. The only fly in the ointment is that when Cys, Hcy and GSH coexist, it is difficult for the probe to achieve selective recognition of each biological thiol.
At the same time, Dunning et al. Established a colorimetric assay for the selective detection of GSH based on the autocatalytic oxidation of OPD by Ag+ (Fig. 2)[21]. Although the detection system is similar to the previous report, the identification strategy is different. In the oxidation process of OPD by Ag+, the generated silver nanoparticles (AgNPs) can catalyze the oxidation reaction and rapidly generate yellow OPDox with an ultraviolet absorption peak at 429 nm. Although Cys, Hcy and GSH can inhibit the oxidation of Ag+, GSH can form a strong Ag — S bond with AgNPs, thus weakening the self-catalytic oxidation ability of silver. In addition, due to the strong reducibility of GSH, the produced OPDox was reduced. Because of the above reasons, GSH can inhibit the oxidation reaction of OPD more easily than Cys and Hcy, and make the detection solution fade. In the presence of other biological thiols, amino acids and common metal ions, the colorimetric probe can detect glutathione with high selectivity, and has a wide linear detection range (2 nM ~ 1 μM) and excellent sensitivity (LOD = 1.7 nM), and has been successfully used to detect GSH content in plasma and urine samples.
In 2019, Meiling Liu et al. Constructed a colorimetric/fluorescent dual-channel probe for detecting GSH based on the oxidation reaction of OPD by MnO2 two-dimensional nanosheets (MnO2NS) (Fig. 3)[22]. Oxidase-like MnO2 nanosheets can catalyze the oxidation of OPD, and the oxidation product OPDox shows a signal at 410 nm in the ultraviolet absorption spectrum and 560 nm in the fluorescence spectrum, respectively. In the presence of GSH, the MnO2 nanosheets will be reduced to Mn2+, thus losing the oxidase-like activity, resulting in the shutdown of the colorimetric and fluorescence signals. It is worth mentioning that the complexation of Ag+ with GSH, which prevents the destruction of the activity of MnO2 nanosheets by GSH, can restore the oxidation reaction of OPD and realize the "on-off-on" of colorimetric/fluorescence signals, thus selectively detecting Ag+. Although the sensitivity of the probe is not very outstanding, for example, the lowest detection limit for GSH is 62 nM (fluorimetry) and 0.94 μM (colorimetry), respectively. However, the colorimetric/fluorescent dual-signal output recognition system can provide more abundant detection information and higher reliability, and shows higher accuracy in the determination of glutathione and Ag+ concentrations in human serum samples, which is very beneficial to the detection of biological thiols in complex environments.
Compared with the single signal probe, the ratio probe can overcome the influence of interference factors such as environment, concentration and instrument, and has obvious advantages in biomolecular detection[23,24]. Also based on the oxidation reaction of MnO2NS to OPD, Li Jianping et al. Recently reported a ratiometric fluorescent probe for detecting GSH (Fig. 4)[25]. Carbon quantum dots (CDs) were added to the detection system as a reference fluorescent substance. The oxidation reaction of OPD in the presence of MnO2NS resulted in fluorescence emission at 570 nm. At the same time, the fluorescence emission peak of CDs at 465 nm is quenched due to the MnO2NS and the inner filter effect (IFE) between the oxidized product OPDox and CDs. With the addition of GSH, MnO2NS was reduced to Mn2+ and then lost its activity, thereby inhibiting the generation of OPDox and restoring the fluorescence emission of CDs. Using the same excitation wavelength, the quantitative detection of glutathione can be realized by the change of the fluorescence of the ratio of I570/I465. Compared with other types of ratiometric fluorescent probes, the probe is cheap and easy to operate, and has a wide linear range (1 ~ 100 μM), but a higher detection limit (270 nM)[26].

2.2 Reactive oxygen species

Reactive oxygen species (ROS) such as hydrogen peroxide, hydroxyl radical (· OH), hypochlorite (ClO-), and peroxynitrate (ONOO-) act as second messengers in cell signaling, affecting normal cell growth, proliferation, and differentiation[27]. Because of its strong oxidative capacity, the abnormal concentration of ROS will destroy nucleic acids, proteins and lipids, leading to irreversible apoptosis of cells and causing serious diseases[28].
In 2019, Tan Yueming et al. Reported a hydrogen peroxide ratiometric fluorescent probe based on OPD oxidation reaction (Fig. 5)[29]. On the one hand, ruthenium complex carbon nitride nanosheets (Ru-C3N4) have peroxidase-like activity, catalyzing the oxidation of OPD by hydrogen peroxide to produce yellow fluorescent OPDox; On the other hand, the generated OPDox will quench the autofluorescence of Ru-C3N4 due to IFE, thus forming ratiometric fluorescence (I565/I455). The fluorescence ratio showed a good linear relationship with the concentration of hydrogen peroxide in the range of 0 ~ 1 mM, and the detection limit was 50 nM. In addition, the probe can not only accurately detect the concentration of hydrogen peroxide in metabolites, but also realize the analysis of glucose, the precursor of hydrogen peroxide metabolism in human serum, on the premise of determining the concentration of glucose oxidase (GOx). The anti-interference experiment shows that the probe has high specificity and selectivity to glucose under the coexistence of common metal ions, saccharides and amino acids in the human body, which lays a foundation for in situ detection in cells. Subsequently, based on a similar strategy, Patra et al. Designed a copper nanocluster-pepsin complex (Cu23@pepsin) with peroxidase activity, which also realized the in situ detection of H2O2 through the ratiometric fluorescence of OPDox and Cu23@pepsin fluorescence emission peaks[30]. Unlike the previous example in which ratiometric fluorescence was generated based on IFE, the fluorescence quenching of Cu23@pepsin by OPDox was achieved by photoinduced energy transfer (PET). It is worth noting that after simple extraction and separation, the Cu23@pepsin in the detection system can be recycled, and after four cycles, it can still maintain 85% of the activity, showing high stability and durability.
In 2014, Khashab et al. Reported several highly reactive oxygen species (hROS) fluorescent sensors based on the mechanism of direct oxidation of gold nanoclusters, but their application was limited due to the inability to avoid the interference of other reactive oxygen species[31]. In 2020, Zhang Qunlin et al. Designed a novel gold nanocluster (SLB-AuNCs) as a ratiometric fluorescence probe based on the specific fluorescence response of OPD to hROS, which realized the selective detection of hROS under physiological conditions (Fig. 6)[32]. Without any enzyme, OPD can be directly oxidized to yellow fluorescent OPDox by highly reactive oxygen species such as · OH, ClO- and ONOO-, while other reactive oxygen species such as H2O2, O2 and 1O2 require the participation of specific enzymes to achieve this oxidation process. The novel gold nanoclusters have excellent monodispersity, quantum efficiency and photostability, and exhibit stable fluorescence emission at 480 nm under physiological conditions, which are used as reference fluorescence. When present, hROS will preferentially oxidize OPD and lead to fluorescence emission at 560 nm. At the same time, the oxidation product OPDox will quench the fluorescence of SLB-AuNCs due to fluorescence resonance energy transfer (FRET), forming the ratiometric fluorescence of I560/I480. The probe not only shows outstanding anti-interference ability for common reactive oxygen species, reactive nitrogen species and biomolecules, but also has high sensitivity, with detection limits of 0.11 μM, 0.50 μM and 0.69 μM for · OH, ClO- and ONOO-, respectively. In addition, the probe has good fluorescence stability and biocompatibility at physiological pH, and has been successfully applied to HeLa cell imaging. After incubation with lipopolysaccharide (LPS) and phorbol myristate acetate (PMA), endogenous hROS was generated in the cells, and after interaction with the probe, the cells changed from blue (Fig. 6A, D) to yellow (Fig. 6E, H) under the confocal fluorescence microscope.

2.3 Purine and its metabolites

Purine, as a widely existing biomolecule in human body, plays an important role in energy supply, metabolic regulation and coenzyme composition. For example, xanthine is an important intermediate in the metabolism of purine nucleotides and deoxynucleotides, and abnormal levels of xanthine can cause hyperuricemia and even gout[33]. For the detection of xanthine, Wang Xianxiang et al. reported a ratiometric fluorescence/colorimetric dual-channel fluorescence probe based on iron-nitrogen co-doped carbon dots (Fe, N-CDs) catalyzed OPD oxidation reaction in 2020 (Fig. 7)[34]. The detection mechanism of the probe is as follows: under the action of xanthine oxidase, xanthine is oxidized to form H2O2. Subsequently, Fe, N-CDs with catalase-like activity catalyzed the oxidation of OPD by H2O2, and the oxidation product OPDox produced fluorescence emission at 560 nm and appeared yellow. At the same time, due to the inner filter effect, OPDox will weaken the fluorescence of Fe, N-CDs at 450 nm, resulting in ratiometric fluorescence (I560/I450). With the increase of xanthine concentration, the fluorescence ratio and absorbance values increased gradually, and showed a linear correlation in the concentration range of 0 ~ 70 μM and 0 ~ 40 μM, respectively, with the minimum detection limit of 0. 02 μM and 0. 023 μM, respectively, showing a high sensitivity. The probe has good anti-interference ability for common biomolecules such as cholesterol, acetylcholinesterase, cysteine and glucose, and has been successfully used for the detection of xanthine in human serum and urine.
As the final metabolite of purine, uric acid (UA) content is an important clinical indicator for the diagnosis of acute gouty arthritis, diabetes mellitus and coronary heart disease[35]. In 2019, Zhang Youyu et al. Reported a ratiometric probe based on tandem catalytic oxidation reactions, which can achieve dual-signal output for UA recognition (Fig. 8)[36]. The fluorescence response of the probe was achieved by a two-step oxidation reaction: uric acid was oxidized to allantoin and by-product H2O2 under the catalysis of uricase, and the latter was then oxidized to OPDox under the catalysis of iodide ion, resulting in 565 nm fluorescence emission and color change. In order to achieve the detection effect of ratiometric fluorescence, silicon nanoparticles (SiNPs) were used as the reference fluorophore, and the fluorescence emission at 450 nm was quenched due to the IFE effect. In the range of 0.01 – 0.8 mM, the concentration of uric acid increased linearly with the absorbance (A470) and fluorescence ratio (I565/I450), respectively, and the detection limits of colorimetric method and ratiometric fluorescence method were 8.4 μM and 0.75 μM, respectively. The test data of uric acid content in human serum samples by the probe are very close to the test results of medical blood glucose/uric acid meter, showing high accuracy and reliability. The disadvantage is that the existence of high concentration of vitamin C has great interference to the probe, which needs to be improved in the future.
In the same period, He Yu et al. Also constructed a ratiometric colorimetric/fluorescent probe for the detection of uric acid by using functionalized multiple quantum dots (GSH-Ti3C2MQDs) as a reference fluorophore[37]. Similar to the above report, OPD was oxidized to yellow fluorescent OPDox by the metabolite H2O2 through the tandem catalysis of uricase-HRP. Differently, the fluorescence quenching of MQDs by OPDox is based on the FRET effect. Because the multiple quantum dots have high fluorescence quantum efficiency, which is beneficial to improve the sensitivity of ratiometric fluorescence, the detection limit of the probe is lower than that reported in the above example. The LOD was 200 nM and 125 nM, respectively, for colorimetric and ratiometric fluorescence detection of uric acid. In addition, the color of the solution changed significantly during the reaction, which made it possible for the probe to identify uric acid with naked eyes. Recently, based on the catalytic oxidation activity and optical properties of carbon quantum dots (CQDs), Wang Yilin et al. Have also achieved colorimetric/fluorescence ratio detection of uric acid content in urine through uricase-CQDs tandem catalysis[38]. It is not difficult to see that the probes in the above reports are designed based on the oxidation reaction of metabolite H2O2 to OPD, thus providing ideas for identifying other biomolecules involved in hydrogen peroxide metabolism.

2.4 Other small biological molecules

Based on the oxidation reaction of metabolite H2O2 to OPD, the fluorescent recognition of metabolic precursors is realized, which is also reflected in the detection of Cholesterol and pyrophosphate (PPI).
Cholesterol content in the blood is an important measure of human health. Cholesterol imbalance can lead to kidney disease, diabetes, anemia, hyperthyroidism and Alzheimer's disease[39,40]. In 2019, Huang Shan et al. Reported a nitrogen and cobalt Co-doped carbon dots (N, Co-CDs) as a ratiometric fluorescent probe for detecting cholesterol content in human serum (Fig. 9)[41]. The co-doped carbon dots have excellent optical properties and strong fluorescence emission at 465 nm. In the detection process, cholesterol is catalyzed and oxidized by cholesterol oxidase to produce H2O2, and then OPD is converted into yellow fluorescent OPDox by the catalytic oxidation of HRP. Due to the IFE effect, OPDox can quench the fluorescence of N, Co-CDs and emit at 540 nm. Because the chemical property of the carbon dot as the reference fluorophore is very stable, the probe has excellent anti-interference performance. In the presence of common metal ions, anions, amino acids and proteins in human body, the probe still has a wide linear detection range (0.01 ~ 500 μM), covering the concentration range of cholesterol in human serum.
As an emerging biomarker, pyrophosphate (PPI) is one of the most important anionic species in biochemical processes and plays a key role in physiological function and disease monitoring[42⇓~44]. In 2020, Liao Weisi et al. designed a new nanoenzyme carbon dot (CDs) colorimetric probe for PPI detection based on the inhibition mechanism of PPI on OPD catalytic oxidation reaction (Fig. 10)[45]. CDs, prepared from galactose and histidine as precursors, has peroxidase-like activity and can catalyze the oxidation of OPD by H2O2 to form a yellow oxidation product OPDox. In the presence of PPI, the selective binding of functional groups on the surface of CDs and PPI seriously interfered with the electron transfer in the enzyme catalysis process, resulting in the effective inhibition of the oxidation process of OPD and the fading of the detection solution. The colorimetric response of the probe is very sensitive, with a detection limit of 4. 29 nM for PPI, and the probe has a strong anti-interference ability for common biomolecules in the physiological environment of PPI, such as adenosine triphosphate (ATP), adenosine diphosphate (ADP), adenosine monophosphate (AMP), urea and anions, which makes it possible to be used in complex matrices. In addition, the probe has excellent compatibility and high stability, and can be printed on paper-based equipment by inkjet, providing a portable PPI detection platform.
Histidine (His) is an important component of proteins, which mainly acts as neurotransmitters and modulators of metal transport in biological systems in the human body[46]. Imbalance of histidine concentration will lead to impaired nutritional status in patients with chronic kidney disease[47]. In 2015, Shen Jiangshan et al. Achieved highly selective and sensitive recognition of histidine based on the oxidation reaction of OPD by Cu2+ (Fig. 11)[48]. Under the action of Cu2+ ions with oxidase-like activity, the oxidation reaction of OPD resulted in a fluorescence response at 564 nm. Because of the strong complexing ability between His and Cu2+ ions, the activity of Cu2+ ions will be significantly inhibited, resulting in a decrease in fluorescence intensity. In the concentration range of 0. 5 ~ 30 μM, the fluorescence intensity at 564 nm decreased linearly with the increase of His content, thus realizing the detection of His. The anti-interference ability test of other 19 amino acids in human body showed that the detection system had specific recognition ability for His. In addition, the sensitivity of the probe was higher (LOD = 0.33 μM) compared with the HPLC and electrochemical methods[49][50]. Although the enzyme-like activity of nanomaterials can also achieve close to the detection limit, the Cu2+ has higher activity, faster response, and no preparation process, which is more convenient in the detection of His content in human urine[51].
Adenosine triphosphate (ATP) is an indispensable energy complex for maintaining many biological processes such as triphosphate cycling, neurotransmission, and DNA synthesis[52⇓~54]. The level of ATP concentration is particularly important for clinical diagnosis of human physiological conditions. Also based on the oxidation reaction of Cu2+ to OPD, Hu Xiaoli et al. Recently reported a ratiometric fluorescent/colorimetric probe for detecting ATP (Fig. 12)[55]. Using CDs as a reference fluorophore, the oxidation products of Cu2+ and OPD quench the fluorescence of CDs at 440 nm through the IFE effect, and emit yellow fluorescence at 565 nm, thus forming a ratiometric fluorescence. In the presence of ATP, the chelation of ATP with Cu2+ will inhibit the oxidation reaction of OPD, hinder the formation of OPDox, eliminate the IFE effect and restore the fluorescence of CDs, resulting in the change of ratiometric fluorescence. Therefore, the ATP concentration can be detected by the change of the I440/I565 ratio. At the same time, the color change of the solution also provides feasibility for colorimetric detection and naked eye identification of ATP. Except for PPI, the presence of other adenosine phosphate molecules, amino acids and anions did not affect the detection effect of the probe. Compared with other zeolite-based and carbon dot-based sensors, the fluorescent probe has a wider detection range (1 ~ 100 μM) and a lower detection limit (0. 43 μM), and shows excellent accuracy and sensitivity in the determination of ATP content in medical disodium adenosine triphosphate tablets and MCF-7 cell lysate[56][57].

3 Detection of Biomacromolecules by Colorimetric/Fluorescent Probes Based on OPD Oxidation Reaction

Biological macromolecules such as enzymes, proteins, nucleic acids, and viruses also play important roles in life processes. In the fields of clinical treatment, biomedical research and food safety, it is of great significance to establish highly sensitive and selective methods for the analysis of biomacromolecules[58]. Although high-resolution mass spectrometry, nuclear magnetic resonance, X-ray single crystal diffraction, cryo-electron microscopy and other detection methods have been developed, the large size, complex structure and highly cross-linked molecular chains of biomacromolecules lead to large sample consumption, long response time and poor selectivity of conventional detection methods[59]. Fluorescent probes can not only overcome the above shortcomings, but also accurately simulate physiological processes through intracellular in situ detection.

3.1 Enzyme

As ubiquitous macromolecular compounds in living systems, enzymes are involved in many key metabolic processes[60]. For example, alkaline phosphatase (ALP) is usually used as a biomarker for clinical diagnosis, and its abnormal concentration level is often used as an important clinical basis for hepatobiliary diseases, bone diseases, prostate cancer and other diseases[61,62]. Because enzymes mainly play a catalytic role in the metabolic process, it is an important design strategy of this kind of fluorescent probes to identify the activity of enzymes through the fluorescence detection of metabolites.
In 2020, Liu Siyuan et al. Reported a quenching ALP fluorescent probe based on IFE[63]. In the presence of Ag+, OPD was oxidized in situ to strongly fluorescent OPDox. At the same time, under the catalysis of ALP, the fluorescence of OPDox was quenched by the IFE effect of p-nitrophenol obtained from the hydrolysis of p-nitrophenyl phosphate (Fig. 13A). This fluorescence response characteristic was successfully used to establish the relationship between ALP activity and fluorescence intensity. In the range of 0.1 ~ 8.0 mU/mL, the fluorescence intensity at 570 nm decreased linearly with the increase of ALP concentration, and the detection limit was up to 0.05 mU/mL (Fig. 13B). It is worth noting that using the strategy of in situ generation of fluorophores (OPDox), the probe does not need to introduce fluorophores through a tedious synthesis process, and has high practicability.
At the same time, Xiong Hua et al. reported a synergistic ternary emission fluorescent probe based on OPD oxidation reaction for visual detection of ALP (Fig. 14)[64]. The probe consisted of MnO2 nanosheets-OPD-red fluorescent quantum dots (r-QDs). Using the oxidase-like activity of MnO2 nanosheets, OPD was oxidized to OPDox(λem=569 nm) with yellow fluorescence, and the fluorescence of r-QDs was quenched by IFE (λem=659 nm). In the presence of ALP, ascorbic acid (AA), a metabolite of 2-phospho-L-ascorbic acid (AAP), will reduce the MnO2 nanosheets and make them lose oxidase-like activity, resulting in 569 nm fluorescence "on-off" and 659 nm fluorescence "off-on", and the probe shows red fluorescence. Further increasing the concentration of AA or ALP, the MnO2 nanosheets were decomposed, and the OPD was reduced to the blue fluorescent substance OPDred(λem=441 nm), which was mixed with the coexisting r-QDs to form purple fluorescence. Compared with the single/dual emission wavelength fluorescent probe, the rich color changes produced by the three emission wavelengths not only facilitate the visual detection of ALP, but also improve the detection range and reliability of the probe. The linear detection range and detection limit of ALP are 0. 1 ~ 100 mU/mL and 0. 06 mU/mL, respectively. The accurate detection of ALP content in food and human serum by the probe shows that the multi-fluorescence emission sensor has great application potential in the field visual detection in complex environment.
Recently, Su Xingguang et al. reported an ALP ratiometric fluorescent probe composed of Au nanoclusters (AuNCs) and OPD (Fig. 15)[65].
The AuNCs modified by Ag+ emit intense fluorescence at 600 nm and are used as reference fluorophores. Under the action of ALP, AAP was converted into AA, which was subsequently oxidized by KIO3 to produce dehydroascorbic acid (DHA), and then reacted with OPD to produce a fluorescent quinoxaline derivative (QXD), which emitted obvious fluorescence at 438 nm. At the same time, the complexation of I- and Ag+ in the system, as well as the oxidative etching and aggregation of I2 on AuNCs, will quench the 600 nm fluorescence. The fluorescence ratio of I438/I600 has a significant linear relationship with the concentration of ALP in the range of 0 ~ 3.0 U/L, and the detection limit is as low as 0.0035 U/L, which can meet the detection of ALP concentration in organisms. The probe has been successfully applied to the detection of ALP content in human serum, and the common interfering substances in the actual physiological environment, such as amino acids, biological enzymes, ions and other biomolecules, have no significant effect on the specific recognition ability of the probe. Interestingly, the fluorescence response of the probe in this example is not generated by the oxidation reaction of OPD, but by the condensation reaction of OPD and DHA, which opens up a new design idea for OPD probes.
Inorganic pyrophosphatase (PPase) is directly involved in physiological processes such as carbohydrate and phosphate metabolism, lipid synthesis and degradation, and bone formation in the human body. The detection of PPase activity is helpful to clarify the molecular mechanism of these processes. In 2016, Yang Xiurong et al. Reported a colorimetric/fluorescent dual-channel probe based on the oxidation reaction of Cu2+ to OPD, which was used to determine the PPase content in serum and cell lysate (Fig. 16)[66]. In this system, the coordination of PPI to Cu2+ would inhibit the oxidation of OPD by Cu2+. PPase can catalyze the hydrolysis of PPI into phosphate (Pi), resulting in the annihilation of its coordination with Cu2+, so OPD is smoothly oxidized into OPDox to achieve fluorescence "turn-on". The results showed that the colorimetric/fluorescence response of the detection system was directly related to the concentration and activity of PPase when the concentrations of PPI, Cu2+ and OPD were fixed, and the logarithm of PPase activity increased linearly with the Log I560 and Log A417 in the range of 0. 2 ~ 50 mU/mL. The probe has good anti-interference ability to common phosphate, but phosphorus-containing biomolecules such as ATP, ADP and AMP have strong complexing ability to Cu2+, which affects the application range of the probe to some extent. In addition, they also carried out the inhibition experiment of PPase with sodium fluoride, and obtained the half inhibitory concentration (IC50) of 63.3 μM and 53.7 μM for fluorescence and colorimetric methods, respectively, which were close to the values reported in other literatures, indicating that the probe could provide a new way for the screening of PPase inhibitors[67].
Acetylcholinesterase (AChE) and cholinesterase (BChE) are the key enzymes in the hydrolysis of choline esters in the central nervous system[68]. Among them, AChE plays an irreplaceable role in maintaining the level of neurotransmitter acetylcholine[69]. In addition, the activity of both enzymes is considered to be a diagnostic biomarker for organophosphate poisoning and nerve agent exposure[70]. Therefore, it is of great significance to establish a method for detecting AChE and BChE activity in whole blood. In 2019, Hu Qin et al. constructed an OPD-CDs ratiometric fluorescent probe to achieve selective recognition of AChE and BChE in human whole blood (Fig. 17)[71]. OPDox, the product of OPD oxidation by Cu2+, can effectively quench the fluorescence of CDs at 460 nm due to the IFE effect, and produce a new emission peak at 570 nm. In the presence of AChE/BChE, acetylthiocholine (ATCh) or butyrylthiocholine (BTCh) is catalytically hydrolyzed to form thiocholine (TCh), whose thiol group strongly captures Cu2+ and inhibits the oxidation reaction of OPD, thus restoring the autofluorescence of CDs and achieving the effect of ratiometric detection (I460/I570). The linear detection ranges of the probe for AChE and BChE were 0. 2 ~ 14.0 U/L and 0. 1 ~ 5.0 U/L, respectively, and the detection limits were 0. 1 U/L and 0. 04 U/L, respectively. Compared with spectrophotometry, the probe not only has higher sensitivity, but also has more advantages in avoiding false positive signals, background interference and sample pretreatment[72]. In order to avoid the interference of the two cholinesterases in the whole blood, they also used Tacrine and Ethopropazine as inhibitors of AChE and BChE, respectively.It not only successfully realizes the selective detection of two enzymes in highly diluted blood samples, but also has good anti-interference ability for coexisting substances such as GSH, Cys, α-milk lipoprotein and β-lactoglobulin in whole blood, which shows the great potential of the probe in clinical diagnosis.
Histone demethylases (HDMs) influence physiological processes by regulating chromatin structure and transcriptional behavior. Among them, aberrant expression of lysine-specific demethylase (LSD) is associated with various diseases such as cancer, metabolic syndrome, and neurological disorders[73,74]. Recently, Huang et al. First reported a colorimetric/fluorescent dual-channel probe based on Ag+ induced OPD oxidation reaction for detection of group LSD activity[75]. Under the catalysis of LSD, methylated lysine undergoes an amine oxidation reaction to produce an important metabolite, formaldehyde, which will inhibit the oxidation process of OPD induced by Ag+, resulting in the reduction of fluorescence and colorimetric signals, thus realizing the detection of HDMs activity. The fluorescence inhibition efficiency showed a good linear relationship with the concentration of LSD in the range of 0. 6-150 nM, with a detection limit of 0. 3 nM, and was successfully applied to the detection of HDMs in cancer cell lysates from patients with liver cancer. It is worth mentioning that because formaldehyde is a common by-product formed during protein and nucleic acid demethylation, this method has broad potential in detecting the activity of different demethylases and identifying novel demethylases.
In addition, Yang Huanghao et al. Combined molecular imprinting technology (MIT) with OPD oxidation reaction to develop a colorimetric/fluorescent dual-channel sensing system for lysozyme detection[76]. Protein-imprinted TiO2@Cu(OH)2 nanoparticles were prepared by solution-phase deposition of lysozyme and TiO2 sol gel coated with Cu(OH)2, which could catalyze the oxidation of OPD to produce yellow OPDox and "turn on" the fluorescence. The fluorescence/colorimetric detection limits of the sensor are 0. 001 mg/mL and 0. 04 mg/L, respectively, which is more sensitive than the conventional lysine blotting method[77].

3.2 Antigen

As an important class of biomarkers, the recognition of antigens is helpful for clinical diagnosis and early warning of diseases. Due to the limitation of detection equipment resolution and analysis methods, traditional methods such as nuclear magnetic resonance, X-ray tomography and electrochemical immunoassay are difficult to achieve the detection of deep human tissues[78]. The application of fluorescent probes in immunology provides a powerful tool for real-time and in situ monitoring of antigens. One of the design strategies of fluorescent probes for OPD in recent years is to prepare immunofluorescent sensors with oxidative or catalytic oxidation ability by immunoreaction.
Prostate specific antigen (PSA), as a tumor marker, is widely used in the early diagnosis of prostate cancer and in the monitoring of prostate cancer patients after radical resection[79]. In 2014, Jiang Liping et al. prepared a sandwich immunofluorescence sensor, which oxidized OPD to produce fluorescence response and realized the detection of PSA (Fig. 18)[80]. The antibody containing CuS nanoparticles was combined with PSA by immunoreaction to form a sandwich structure sensor, and the large specific surface area of multi-walled carbon nanotubes (MWCNTs) was used to enhance the conjugation of biomolecules to achieve signal amplification. Under the oxidation of CuS, OPD was converted into OPDox to realize the fluorescence "turn-on", and the linear relationship between the fluorescence intensity at 558 nm and the concentration of PSA was established. The immunofluorescence sensor has a detection limit as low as 0. 1 pg/mL, and has strong anti-interference ability for carcinoembryonic antigen (CEA), interleukin-6 (IL-6), alpha-fetoprotein (AFP) and immunoglobulin G (IgG), providing a PSA field detection method with high sensitivity and specificity.
Human immunodeficiency virus (HIV) destroys the human immune system by destroying immune cells, resulting in acquired immunodeficiency syndrome (AIDS), commonly known as "AIDS"[81]. Early diagnosis of HIV is helpful for AIDS treatment, but the current nucleic acid detection method based on polymerase chain reaction (PCR) is expensive and complex, which limits its scope of application[82]. In 2016, Yu Junping designed a novel immunofluorescent probe based on OPD oxidation reaction, which achieved rapid recognition of HIV-1 viral antigen P24 (Fig. 19)[83]. Magnetic beads (MBs) were used to immobilize P24 antibody, and P24 antigen was captured by immunoreaction and labeled with biotin to form functionalized magnetic beads. Subsequently, based on the biotin-streptavidin recognition mechanism, horseradish peroxidase (HRP) was modified on the magnetic beads to complete the catalytic oxidation of OPD with its activity, thus realizing the "turn-on" of fluorescence. Compared with the traditional ELISA kit, the detection limit of P24 was 0. 5 pg/mL, and the linear range was 1. 4-90. 0 pg/mL, which could cover the clinical detection concentration[84]. In addition, the short response time (90 min) and strong interference resistance endow the method with rapid and specific recognition of P24 antigen in clinic.
Liver fluke (Opisthorchis viverrine, Ov) infection is the cause of human liver fluke disease, which can cause chronic inflammation of bile duct and even cholangiocarcinoma[85]. However, the sensitivity of traditional enzyme-linked immunosorbent assay (ELISA) is low, which makes it difficult to accurately determine the ultra-low concentration of Ov antigen in urine samples of early liver fluke infection[86]. Recently, Loilome et al. Constructed a highly sensitive gold nanoparticle-linked immunosorbent assay (AuNPs-LISA) based on the fluorescence response of OPD, and successfully detected the content of Ov antigen in urine samples of patients with early ovarian cancer[87]. The detection mechanism was similar to the previous reports. The immunofluorescent sensor containing Ov antigen and AuNPs was constructed by immunoreaction to catalyze the oxidation of OPD by H2O2, and the linear relationship between the fluorescence intensity of OPDox and the concentration of Ov antigen was established. Compared with ELISA, the sensor was constructed with AuNPs with higher catalytic activity instead of the traditional HRP enzyme, the fluorescence response of OPD was used instead of the colorimetric response of tetramethylbenzidine, and the fluorescence signal of OPDox was enhanced by nonionic surfactant. The sensitivity of the probe was increased by about 1200 times, and the detection limit was 36. 97 ng/mL, which could meet the needs of clinical detection.

3.3 Bacteria and virus

Accurate identification of harmful bacteria such as Escherichia coli, Staphylococcus aureus, Streptococcus pneumoniae, influenza virus, and novel coronavirus can effectively prevent the spread of various diseases[88]. Compared with PCR technology, biosensors and electrochemical methods, fluorescent immunosensors have the advantages of fast response and strong recognition specificity, and have been developed rapidly in the detection of pathogens in recent years[89][90][91][92]. In 2014, Chen Guonan et al. Developed a novel immunofluorescence sensor for detecting H1N1 virus based on the OPD oxidation reaction catalyzed by Ag+ (Fig. 20)[93]. By immunoreaction,
Inactivated H1N1 antigen was combined with silver nanoparticle-labeled antibody to form a sandwich-structured probe. After treatment with 0.01 M HNO3, the probe releases Ag+ and induces the autocatalytic oxidation reaction of OPD, which "turns on" the fluorescence. In the presence of other influenza viruses such as H5N1 and H3N2, the probe can specifically recognize H1N1, and has a wide linear range (10-12~10-8g/mL), high sensitivity (LOD=10-13g/mL) and fast response speed (2 H). The probe is prepared into an ELISA kit, which provides a simple, stable and easy-to-operate portable H1N1 virus real-time detection platform.
Listeria, as a foodborne pathogen, can not only survive at low temperature (4 ℃), but also have strong infectivity at low doses[94]. In 2018, Zhao et al. Reported a simple and rapid colorimetric detection method for Listeria monocytogenes (Fig. 21)[95]. The colorimetric system consists of OPD and gold nanoparticles (GNPs). Due to the Au-NH interaction between them, GNPs are easy to aggregate, which leads to the red shift of the localized surface plasmon resonance (LSPR) absorption band, so the solution appears blue. Listeria and immunoglobulin-coated silver nanoclusters (AgNCs) were immunoreacted to form sandwich immune complexes with oxidase activity, which catalyzed the oxidation of OPD and consumed OPD, thus inhibiting the aggregation of GNPs, resulting in a blue shift of LSPR absorption band and a red detection solution. The absorbance at 525 nm was proportional to the logarithm of Listeria concentration in the range of 10~106cfu/mL, and the detection limit was 10 cfu/mL. In addition, the detection system has strong anti-interference ability against nine common pathogenic bacteria, such as Escherichia coli, Staphylococcus aureus and Probacterium monocytogenes, and has been successfully applied to the detection of Listeria in fresh pork samples.
Enterohemorrhagic Escherichia coli O157: H7, as a food-borne pathogen, can cause hemolytic uremic syndrome (HUS) through dietary intake, which can lead to red blood cell destruction and renal failure, and seriously affect human health[96]. Recently, Qi Yanfei et al. prepared a novel nano-oxidase for detecting E. coli O157: H7 based on the oxidation reaction of OPD (Fig. 22)[97]. Escherichia coli was assembled into a sandwich complex with polyoxometalate P2W18Fe4 w hich has peroxidase activity by immunoreaction, and then nano-oxidase was prepared by a simple solvothermal reaction with dopamine (DA) to catalyze hydrogen peroxide to produce hydroxyl radicals for the oxidation of OPD. E. coli O157: H7 was identified by the colorimetric/fluorescence signal of the oxidation product OPDox, and it was found that the fluorescence intensity at 564 nm increased linearly with the logarithm of E. coli concentration in the range of 103~106cfu/mL, and the detection limit was 4.2×102cfu/mL. From the above examples, it can be seen that the colorimetric/fluorescent immunosensor based on nanomaterials has a wide range of sources, low cost and fast response, and is expected to become a new tool to replace the traditional enzyme-linked immunosorbent assay.

3.4 Other biomacromolecule

As the main chemical component of chromosomes, DNA plays a vital role in the storage and transmission of genetic information[98]. In the fluorescence recognition of DNA, graphene quantum dots (GQDs) have the advantages of high luminescence efficiency, low toxicity and good biocompatibility, and have great potential for application. However, the DNA molecular labeling of GQDs is very cumbersome and time-consuming, causing great inconvenience[99]. In 2016, Wang Guangli et al. designed a label-free DNA fluorescence detection method based on the oxidation reaction of OPD by using GQDs as a reference fluorophore (Fig. 23)[100]. First, the hairpin DNA probe is hybridized with the target DNA to form a bimolecular strand, which is quickly cut into two pieces by endonuclease. One of them is inserted into the heme to form a G-quartet/heme deoxyribozyme (DNAzyme), which catalyzes the oxidation of OPD by means of its peroxidase-like activity. The resulting OPDox quenched the fluorescence of GQDs at 460 nm via the FRET effect, while producing fluorescence emission at 564 nm. The results showed that the change of I460/I564 ratio was linearly related to DNA concentration, and the detection limit was 30 fM. It is worth noting that the target DNA is only involved in the formation of the DNAzyme cycle and is not consumed during the detection process. This means that a low concentration of target DNA can produce enough DNAzyme to catalyze the reaction, thus endowing the method with signal amplification. This design idea provides a reference for the application of OPD oxidation reaction in the fluorescence detection of other nucleic acids.
Nuclear matrix protein 22 (NMP22), as one of the important proteins to maintain nuclear function, is a tumor biomarker for the diagnosis of bladder cancer in clinic[101]. In 2019, Zheng Gengxiu et al. Reported a NMP colorimetric/fluorescent probe based on OPD oxidation reaction (Fig. 24)[102]. NMP 22 antibody and porous palladium nanoparticles (Pd NPs) were first used to prepare nanoenzyme-palladium NPs with peroxidase activity, which were combined with NMP 22 to form a sandwich-type complex by immunoreaction. The complex can catalyze the oxidation reaction of OPD and realize the colorimetric/fluorescent signal amplification of OPDox by ELISA technology. The probe has excellent sensitivity (LOD = 0.31 pg/mL), and the fluorescence intensity and absorbance increase linearly in the concentration range of 1 ~ 500 pg/mL. The probe shows high accuracy in the determination of NMP content in human serum, which provides a reliable detection method for the clinical diagnosis of bladder cancer.

4 Conclusion and prospect

In recent years, great progress has been made in the design and synthesis of colorimetric/fluorescent probes for different detection platforms. The unique fluorescence response of OPD oxidation reaction provides an important idea for the design of new colorimetric/fluorescent probes. In this paper, the research progress of colorimetric/fluorescent probes based on OPD oxidation reaction in biomolecular recognition in recent years is reviewed. It can be seen that most probe design strategies are based on the "on-off" or "off-on" response of colorimetric/fluorescent signals caused by the promotion/inhibition of OPD oxidation by biomolecules or their metabolites. This kind of probe shows excellent sensitivity, anti-interference and rapid response ability in the recognition of human plasma, serum, urine and intracellular biomolecules, and provides a powerful tool for clinical diagnosis and physiological mechanism research. The relevant performance is summarized in Table 1. At the same time, there are also some challenges to be overcome in the development of this kind of probe, such as (1) designing probe molecules with good water solubility and biocompatibility, which is helpful to improve their in situ detection ability in vivo; (2) The near-infrared fluorescent probe has the advantages of strong tissue penetration and good imaging effect[103]. The development of near-infrared probes with OPD structure can enhance the tracing and imaging effect in complex biological systems. (3) With the increasing demand for field testing, portable probe equipment is a future development direction. A kit suitable for clinical detection can be prepared by combining the probe with ELISA technology. In addition, the current recognition mechanism is mainly based on the oxidation reaction of OPD. However, there are some reports that fluorescent heterocyclic compounds can be formed by the condensation reaction of OPD and α-dicarbonyl compounds, which provides a new idea for the design of OPD reactive fluorescent probes.

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Funding

Natural Science Foundation of China(21762018)

Natural Science Foundation of China(21961014)

Science and Technology Project Founded by the Education Department of Jiangxi Province(GJJ160668)

Jiangxi Provincial Natural Science Foundation(20202BABL213007)

Jiangxi Provincial Natural Science Foundation(20212BAB203013)

Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry(20212BCD42018)

National Training Programs of Innovation and Entrepreneurship for Undergraduates(202110407006)

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