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Recent application of near-infrared fluorescence probes in food safety detection

State Key Laboratory of Molecular Vaccinology and Molecular Diagnostics, State Key Laboratory of Vaccines for Infectious Diseases, Center for Molecular Imaging and Translational Medicine, Xiang An Biomedicine Laboratory, School of Public Health, Xiamen University, Xiamen 361102, P. R. China

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Zhongrui Peng

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Yun Zeng

Department of Pharmacy, Xiamen Medical College, Xiamen 361023, P. R. China

E-mail Address: zengyunxmmc@xmmc.edu.cn

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, and

Gang Liu

https://orcid.org/0000-0003-2613-7286

The Key Laboratory of Biomedical Imaging Science and System, Chinese Academy of Sciences, Shenzhen Research Institute of Xiamen University, Shenzhen 518000, P. R. China

E-mail Address: gangliu.cmitm@xmu.edu.cn

Corresponding author.

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https://doi.org/10.1142/S1793545825300034Cited by:0 (Source: Crossref)

Abstract

Fluorescent probes have wide applications in biological and environmental analysis due to their advantages of simple operation, convenient flexibility, high sensitivity and efficiency. They are considered to be promising tools for accurate analysis of agriculture- and food-related hazardous substances. In this review, the types and characteristics of the near-infrared fluorescence probes (NIFPs) are briefly described. The recent advances of NIFPs for precisely detecting various hazardous substances including heavy metals, sulfite and related sulfiting agents and hydrogen peroxide are summarized. Finally, the present challenges and future perspectives faced by NIFPs in food safety analysis are discussed.

Keywords:

1. Introduction

Food safety is an important public health issue with the aim of ensuring the supply of nutrient-rich and safe food. It is strongly associated with human health, which has received a great deal of attention. Food safety and quality are greatly influenced by the environment.¹ Industrial waste and widespread utilization of pesticides have resulted in environmental pollution. The polluted soil, water and air may contaminate crops, vegetables, fish and animals, which ultimately find their way into the human body through the food chain and can significantly threaten human health.^2,3 Considering the important impact of food safety and quality on human health, it is essential to develop fast, convenient and highly sensitive methods for early detection of food contaminants. Various techniques have been developed to identify the specific substances or toxins in food, such as high-performance liquid chromatography (HPLC), enzyme-linked immunosorbent assay (ELISA) and gas chromatography (GC).⁴ These methods have high sensitivity and selectivity, but they are unsuitable for wide application since these methods are time-consuming and require expensive equipment and skilled operators.

Near-infrared (NIR) spectroscopy technology has experienced tremendous advancements in recent years and found wide applications in various fields, such as analytical chemistry, agriculture and food industry.^5,6,7 Meanwhile, NIR fluorescent probes (NIFPs) have been reported and attracted much attention, they have a characteristic molecular structure with a highly conjugated polyene system.⁸ NIFPs can produce deeper tissue penetration without inducing any photochemical damage and possess a high signal-to-noise ratio and detection sensitivity.⁹ They have been widely used in immunoassay, bio-imaging and medical diagnosis.^10,11 Their high sensitivity and selectivity have enabled them to find a wide range of applications in the bioanalysis of the food industry.¹² Furthermore, compared with conventional technologies, NIRPs have the advantages of high resolution, simple operation and high cost-effectiveness.^13,14,15,16 Although there have been many reviews on NIFPs, they mainly focused on their bioimaging applications or the application in some specific aspect of food safety. Comprehensive reviews on their application of food safety are few. Therefore, in this review, we discuss the structures and characteristics of NIFPs and review their latest application in the food safety detection in recent 5 years. Moreover, the potential challenges and opportunities of NIFPs in these emerging fields are also discussed.

2. Types and Characteristics of NIFPs

Although the concept of NIFPs is simple, multiple steps are required to synthesize and purify the probes. NIFPs in the first NIR region are usually obtained by using donor–acceptor (D–A) system. The strong electron donors and acceptors are combined in a molecular structure, and the bandgap energy is reduced, leading to NIR-I probes. Furthermore, a second strong donor in the D–A architecture could be introduced, which could produce the symmetrical donor–acceptor–donor (D–A–D) architecture. The energy gap between hybridized highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels is lowered by the strong electron-donating groups close to the central electron acceptor, producing NIR-II probes.¹⁷ Four types of NIFPs have been discussed and each has its own unique characteristics, which enable them to find wide application in the detection of various harmful substances in food. The schematic illustration of the NIFPs categories has been presented in Fig. 2.

2.1. Near-infrared fluorescent dyes

Among many classes of fluorescent dyes, polymethine dyes (e.g., cyanines, hemicyanines and benzopyryliums) and xanthene dyes (rhodamines and fluoresceins) have been widely produced and applied in molecular imaging and clinical diagnostics. Other dyes such as squaraines, 4,40-difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) and some (benzo)phenoxazines and respective phenothiazines (e.g., Nile red) have also attracted much attention and have been employed as labels for immunoassays (Fig. 1).⁸

Fig. 1. Basic chemical structure of NIRF dyes. Reproduced from Ref. 8 with permission from the authors, copyright 2019.

Fig. 2. Schematic illustration of the NIFPs categories. With the advantages of sensitivity, convenience and low limit of detection, NIFPs are considered to be promising tools for accurate analysis of agriculture- and food-related hazardous substances.

As traditional dyes, cyanine dyes have attracted considerable interest and are widely employed in many fields of science and technology.^18,19 The cyanine chromophore is a polymethine chain. The conjugated –C=C– bonds usually link terminal heterocycles (thiazoles, etc.) and an odd number of C atoms. The spectral region of absorption and emission of the dyes could be determined by the length of the chain. The cyanine dyes in the NIR region mainly include pentamethine cyanines with a five-methylene polymethine chain and heptamethine cyanines with a seven-methylene polymethine chain. Cyanine has poor photostability and is easy to be photooxidatively bleached. Their photooxidation reaction follows the first-order reaction kinetics. When cyanine dyes have the same methine chain, their stability decreases (indole > oxazole > thiazole > selenazole) with the increase of the substitution of heteroatoms on the heteronuclear core. When the structure of the heteronuclear core is the same, the photostability becomes worse when the hemi-chain is longer. These characteristics are crucial for improving the light stability of NIR cyanine dyes. Cyanine dyes possess attractive fluorescence properties such as high molar absorptivity and long absorption/emission wavelength,²⁰ excellent biocompatibility and low toxicity.²¹ Cyanine 3 and cyanine 5 have been employed in antibody/protein microarrays or DNA microarray assays to detect foodborne pathogens and toxins.^22,23 Furthermore, modified chemical groups allow the dyes for further improvement of chemical and optical properties. Indocyanine green (ICG) has been approved by the U.S. Food and Drug Administration (FDA) for NIR in vivo imaging of humans.²⁴ Some other cyanine dyes in the NIR-I region are commercially available such as IR-125, CF770 and Alex Fluo@750.

Rhodamine and fluorescein are two classical xanthene fluorescent dyes with naphthalene ring fluorescein in the NIR spectral region. They have the advantages of high fluorescence quantum yields and high molar absorption coefficients, which enable them to be applied for the construction of fluorescent probes.²⁵ Some NIR rhodamine fluorescent dyes have been commercialized to be used for biomedical imaging and fluorescence-based assays. Invitrogen Corporation and Molecular Probes Inc. of the United States have introduced Alexa Fluor^® dye series such as Alexa Fluor^® 488, Alexa Fluor^® 546, Alexa Fluor^® 555 and the DY55x series. These dyes include both cyanine and rhodamine derivatives of improved photostability and fluorescence quantum yields. The wavelengths of Alex Fluoro’s xanthene-like fluorescent probes range from the visible region to the NIR region.²⁶ The sulfonic acid group in their structure increases the water-solubility of the probes, enabling them suitable for bioanalysis and medical diagnostics. Some rhodamine-based fluorescent probes have been designed for the detection of Pb $^{2 +}$ , Hg $^{2 +}$ and Cr $^{3 +}$ in seafood and real water samples.^27,28,29

BODIPY was first synthesized in 1968³⁰ and worked as a versatile visible region emitter with extraordinary properties such as strong fluorescence, sharp emission and absorption bands. It is not sensitive to pH and solvent polarity, exerting good stability under various environmental conditions. Its emission and absorption ranges could be fine-tuned by attachment of functional groups of the desired character. Differently substituted BODIPY dyes have found lots of potential applications in biomolecule labeling and in the design of energy transfer cassettes.^31,32 Some strategies have been reported to shift BODIPY into near-infrared fluorescent (NIRF) dyes such as modifying the phenyl rings and merging the 3- and 5-phenyl rings with the aza-BODIPY core.^33,34 Bromo-substituted BODIPY-containing thienopyrrole moieties have been developed and exhibited a high singlet oxygen quantum yield in the NIR region.³⁵ Chen et al. employed BODIPY to develop a $β$ -galactosidase-activatable fluorescent probe BOD-Gal. BODIPY served as the fluorophore to form a $β$ -O-glycosidic bond with galactose, allowing the BOD-Gal to show significant on–off fluorescent signals for in vitro and in vivo detection of Escherichia coli. The probe exhibited great potential in the detection of food pathogen.³⁶

Phenoxazine and benzophenoxazine are the two best-known fluorescent dyes. These dyes mainly include Nile red, Nile blue, Methylene blue and Toluidine blue. Substituents that freely donate and/or accept electron density on the benzophenoxazine cores can, in proper orientations, produce some fluorescent compounds. Meldola’s blue is the first discovered fluorescent compound in this class. However, the most frequently used dyes are Nile red and Nile blue. Nile red is very sensitive to the dye environment and the polarity of the surrounding medium could obviously affect its spectroscopic features. Because of its poor water solubility, Nile red is usually employed as a polarity probe, especially for hydrophobic systems.³⁷ In Seto’s study, Nile red was used to develop a fluorescent probe with the iminodiacetic acid-Ni $^{2 +}$ complex. In the probe, Nile red dye worked as the hydrophobic part and the iminodiacetic acid (IDA)-M $^{2 +}$ complex acted as the hydrophilic part. The probe had good adaptability in the detection of histamine in various cells and organs.³⁸ Nile blue has better water solubility and is more stable than rhodamines and BODIPYs under acidic conditions. But they have much smaller fluorescence quantum yields than those of rhodamines, cyanines and squaraines. Methylene blue and toluidine blue are the well-known dyes of the thiazine and phenothiazine classes, which are usually employed as colorants and stains.³⁹

2.2. NIRF rare earth metal chelates

Among the existing NIR materials, many complexes of the lanthanides containing La $^{3 +}$ , Eu $^{3 +}$ , Tb $^{3 +}$ , Nd $^{3 +}$ and Yb $^{3 +}$ have exhibited unique advantages such as large Stokes shift, sharp emission spectra and high chemical/photochemical stability.^40,41,42 Yb₂O₃ is the first generation of NIR emissive lanthanide material.⁴³ Vetrone et al. found NIR emission was observed in nanocrystalline and bulk Y₂O₃:Er $^{3 +}$ when the dopant concentration increased.⁴⁴ In Soga’s study, liposome-encapsulated, Er-doped Yb₂O₃ nanoparticles with various surface modifications have been developed as a fluorescent probe for NIR bioimaging.⁴⁵ In Ahmed’s study, Yb₂O₃.CuO@rGO nanocomposite was developed to accurately determine the levels of ascorbic acid in human blood serum and commercial vitamin C tablets.⁴⁶ Rare earth fluorides, such as NaYF₄ and NaGdF₄ were widely employed as doping matrices for lanthanide phosphor.⁴⁷ NaLnF₄ has been most widely applied as a matrix for NIR emission because of its high emission efficiency and excellent chemical stability.⁴⁸ NaGdF₄ was used as a contrast agent in MRI on account of its great magnetic properties.⁴⁹ In addition, some new matrices have been employed for NIR emission of lanthanides, which endow the nanoparticles with new properties such as long persistence emissive phenomenon and degradability in physiological fluids. Lanthanide-doped Ca $_{0.2}$ Zn $_{0.9}$ Mg $_{0.9}$ Si₂O₆ nanoparticles with NIR persistent luminescence have been synthesized by Scherman et al.⁵⁰ The nanoparticle could be used to evaluate the tumor mass in mice and exhibit great potential in clinical application. The NIR emitting nanoparticle of Zn $_{2.94}$ Ga $_{1.96}$ Ge₂O $_{10}$ co-doped with Cr $^{3 +}$ , Pr $^{3 +}$ has been developed and the nanoprobe found its application in MRI and NIR luminescence imaging after it is functionalized with gadolinium complexes.⁵¹ Recently, an analytical strategy based on the NIR fluorescence of multi-color upconversion nanoparticles (type NaYF4: Yb, Er, NaYF4: Yb, Tm) labels was developed to detect tyramine and histamine concurrently in meat, fermented products and aquatic origin foodstuffs. The strategy reduced the total test time and promoted the efficient detection of the targeted biogenic amines.⁵²

2.3. NIRF quantum dots

Quantum dots (QDs) are nanosized semiconductor crystals, which have been widely employed in biomedical science and industry.⁵³ QDs’ fluorescence is size-tunable. The desired color could be achieved by adjusting QDs’ size and composition.^54,55 A redshift in fluorescence could be obtained by increasing the diameter of QDs.⁵⁶ NIR QDs not only have the characteristics of NIR, but also those of QDs, which could target deep-rooted tumors with low-intensity lights.⁵⁷ NIR QDs have broad absorption spectra and can be excited by a broad range of irradiation wavelengths, but exhibit narrow and sharp fluorescence emission peaks. They possess high extinction coefficients and better resistance to photobleaching than organic dyes.⁵⁸ Moreover, the marking technique of QDs is very simple and can be widely used in food safety testing. Some of QDs have been employed in the detection of histamine in food.⁵⁹ A detection system uniting the upconversion nanoparticles (type NaYF4: Yb, Tm) with the CdTe QDs was conducted to monitor multiple food pathogens with high specificity and sensitivity.⁶⁰ However, the biocompatibility of NIR QDs is still a major concern due to their potential toxicity to organ and tissue damage. Encapsulation with a stable polymer shell is usually considered in the design of NIR QDs.⁵⁴ However, the shell may impact on the optical properties of the core and also make it difficult to regulate the size of the QDs. A NIR QDs fluorescent probe was synthesized by modifying CdTe/CdS NIR QDs with a bovine serum albumin–glycyrrhetinic acid conjugate and arginine-glycine-aspartic acid. The probe not only exhibited toxicity toward liver cancer cells but also showed high targeting efficiency.⁶¹

2.4. Single-walled carbon nanotubes

Single-walled carbon nanotubes (SWCNTs) are closed or open-ended cylinders made of a single graphene layer.⁶² The diameter of SWCNTs ranges from 0.4nm to 2nm depending on their growing temperature. The higher the temperature used to produce them, the smaller the diameter of SWCNTs.⁶³ They have many extraordinary features, such as high strength, high thermal conductivity and electrical properties spanning metal to semiconductor.⁶⁴ Semiconducting SWCNTs are outstanding NIRF materials. They have bright fluorescence emission in the NIR spectral range between 900nm and 1600nm, and a broad absorption spectrum.⁶⁵ Their high surface areas can be readily functionalized. SWCNTs have high stability and do not photobleach or blink.⁶⁶ The NIR fluorescence and robust functionalization endow SWCNTs with prolonged detection through biological samples. Furthermore, the physical dimensions of SWCNTs match the typical size of biological molecules, enabling precise targeting and visualization.⁶⁷ Thus, SWCNTs are attractive NIFPs candidates for detection and analysis of toxic materials in the agricultural sector. SWCNTs have been employed to analyze the pesticides in teas⁶⁸ and lake water⁶⁹ and monitor the pathogenic bacteria in food processing.⁷⁰

3. Application of NIFPs in the Detection of Food Safety and Quality

3.1. Detection of heavy metals

As the global world becomes more technologically advanced, heavy metal pollution has become an international problem and has long-term detrimental effects on the ecosystem and human health. Heavy metals are mostly derived from the excessive discharge of industrial and urban trash, abuse of pesticides and fertilizers, metal smelting and transportation. These heavy metals are released into the soil and surface water, which can be easily accumulated in aquatic products, crops and other foodstuffs in the form of ions.^71,72 Through the food chain, heavy metals are absorbed by humans and distributed to organs and tissues, which cause neurological disorders and dysfunction of immune system, gastrointestinal tract and kidney and even some cancers.⁷³ It is necessary to set up rapid, sensitive and accurate methods for the detection of heavy metals in food.

Traditional methods have been employed in quantitative analysis of trace heavy metals in food, including inductively coupled plasma-mass spectrometry (ICP-MS), atomic fluorescence spectrometry (AFS), atomic absorption spectrometry (AAS), atomic emission spectrometry (AES), X-ray fluorescence spectrometry (XRF), etc.^74,75 Recently, lots of NIR fluorescent probes have been developed and widely employed in the detection of metal ions due to their extraordinary characteristics. The sensor of the probe is usually composed of a fluorescent carrier and an ionic carrier as independent species or covalently linked on a molecule. After the probe binds with the analyte, the photophysical properties of NIR fluorescent probes change significantly to facilitate the detection of heavy metals in food or the organism.⁷⁶ Wu et al. have designed the RBLY as a new NIR probe to recognize Hg $^{2 +}$ , which was synthesized by using the platform of rhodamine dye (Fig. 3).⁷⁷ It could turn on strong fluorescence upon sensing Hg $^{2 +}$ in the EtOH/H₂O (1:5, v/v) system and the generated fluorescence did not disappear over time. Its detection limitation was as low as 0.34 $μ$ M and the binding constant was $1.63 \times 1 0^{5}$ M $^{- 1}$ . Furthermore, a reversible effect could be achieved by adding S $^{2 -}$ . The addition of S $^{2 -}$ would reduce the fluorescence of the probe and restore the structure of the probe to its original state. The probe was not only able to determine Hg $^{2 +}$ in water samples but also stain living cells and plant cells. Liu et al synthesized a novel Schiff base derivative HMA containing dicyanomethylene-4H-pyran (DCM) unit.⁷⁸ It was applied to identify Al $^{3 +}$ and Cr $^{3 +}$ accompanied by obvious NIR fluorescence enhancement in the DMSO/H₂O (v/v = 9:1) system. The detection limit was $3.26 \times 1 0^{- 7}$ M and $5.63 \times 1 0^{- 7}$ M for Al $^{3 +}$ and Cr $^{3 +}$ , respectively. The probe has been successfully utilized in the detection of water samples. Li et al. developed a NIR fluorescent probe for the determination of Pb $^{2 +}$ by a simple Schiff base reaction between the dicyanoisophorone skeleton and carbohydrazide derivatives.⁷⁹ The probe with the thiophene-2-carbohydrazide group showed a selective fluorescence response to Pb $^{2 +}$ . The maximum emission wavelength was 670nm. It has been successfully applied in the fast detection of Pb $^{2 +}$ in real water samples with the detection limit of 1.65nM.

Fig. 3. (A) The response mechanism between RBLY and Hg $^{2 +}$ . (B) Coloring of soybean rhizomes ( $λ$ _ex = 620nm). (1) Soybean rhizomes grown in Hg $^{2 +}$ solution (20 $μ$ M), (2) Soybean rhizomes cultured in Hg $^{2 +}$ solution (20 $μ$ M) were soaked in RBLY (20 $μ$ M) for 1 h, (a) fluorescent images, (b) bright field, (c) the overlay images. Scale bar: 50 $μ$ M. Reproduced from Ref. 77 with permission from Elsevier B.V., copyright 2022.

3.2. Detection of sulfite

Sulfite and related sulfiting agents are types of food additives that are widely applied in the food-processing industry.^80,81,82 They are utilized as antioxidants, bleaching agents, flour treatment agents and preservatives in various food and beverage products such as dried fruits and vegetables, wine, cordials and seafood. They can maintain food color, extend shelf life and prevent microbial growth.⁸³ They are also used in some food packaging material production and as processing aids to sterilize bottles before packaging food or drinks. Sulfite is present in food in three forms including sulfurous acid, inorganic sulfites and other forms bound to the food matrix. Sulfites contribute beneficial effects to food products and are regarded as safe if used conforming to good manufacturing practices. However, the excessive addition could induce harmful effects on human health. Studies have reported that frequent exposure to SO₂, and its anionic derivatives are related to certain diseases, such as cardiovascular diseases, neurological disorders and cancer. Furthermore, some highly sensitive individuals may have an adverse allergy-like reaction such as skin rashes, nausea and respiratory distress even if they only consume very low levels of these compounds.⁸⁴ Because of their potential health concerns, the content of sulfite and/or related sulfiting agents has been strictly limited in foods and beverages. The Joint FAO/WHO Expert Committee on Food has limited the daily intake of sulfites to 0.7mg/kg body weight.⁸⁵ The U.S. FDA has set 10ppm as the threshold for the declaration of sulfite on the label of any product. The Chinese Hygienic Standard for the Use of Food Additives requires the maximum SO₂ content in cookies, sugar, vermicelli and canned foods is 0.05 g/kg, and SO₂ content in other varieties should not exceed 0.1 g/kg.⁸⁶ However, some manufacturers add excessive amounts of sulfites to make a profit or to meet technical standards, which poses a risk to public health and endangers the trade economy as well. Therefore, it is essential and highly demanded to develop a sensitive, fast and cost-effective method to determine sulfite for food quality control and quality assurance.

AOAC Official Method 990.28 has been identified as the required method by FDA for all regulatory analyses of sulfites in most food products.⁸⁷ However, this method includes an extended distillation, exhibits reduced sensitivity below 10ppm of SO₂, and low specificity in some matrices.⁸⁸ Various methods such as electrochemical methods, ion exchange chromatography, liquid chromatography, flow injection analysis, spectrophotometry and iodometry, have also been reported in previous studies for sulfite determination.⁸⁹

In recent years, fluorescent probes have been developed for the detection of various anions. The first fluorescent probe for sulfite was constructed by Choi et al. in 2010.⁹⁰ and then various fluorescent probes have been synthesized based on the nucleophilic reactions of aldehydes, selective deprotection of levulinate, Michael-type additions and coordinative interactions.⁹¹ However, in real food analysis, these probes are still facing some problems which may impact the accuracy of the results, such as the interference from hydrogen sulfide, biogenic amine and some enzymes and the overlap of the probes’ fluorescence with the background fluorescence of food components. NIR fluorescence probes can fully avoid the interference from the background fluorescence of food samples. A high-performance NIR fluorescent probe DCQN has been developed by Jiang et al. to detect sulfite levels in food.⁹² DCQN was synthesized by combining two electron-withdrawing moieties, methylquinolinium and 2-(3,5,5-trimethylcyclohex-2-enylidene) malononitrile with an acceptor– $π$ -conjugation–acceptor (A– $π$ – $A)$ structure. Because of the intramolecular charge transfer (ICT) effect, DCQN could exhibit chromogenic and NIR fluorescence turn-on response towards sulfite. It only took 4.5s to complete the reaction and the detection limit for sulfite was as low as 24nM. Therefore, DCQN could be employed to accurately determine the sulfite level in real food with high sensitivity and good recoveries. Furthermore, it can also be used for the on-site detection of sulfite in food by incorporating it into hydrogel as a portable device. In Zhong et al.’s study, a hyperchromic NIR fluorescent probe was synthesized, consisting of donor-p-acceptor fluorophore and 2,4-dinitrophenyl ether moiety. It can be employed to monitor H₂S in red wine, real water and living cells (Fig. 4).⁹³ Chao et al. established a NIR fluorescent probe of NIR-BN by conjugating the benzopyrylium moiety and 6-hydroxy-2-naphthaldehyde. The probe could detect SO $_{3}^{2 -}$ with high selectivity and rapidity with an emission wavelength of 680nm. The detection limit of NIR-BN was as low as 0.17mM and was applied to the detection of SO $_{3}^{2 -}$ in different sugar samples.⁹⁴ In Shang’s study, a bifunctional NIR fluorescent probe of QZB was synthesized by linking 3H-benzo [f]chromene and 1,3-indanedione via a C=C bond for selective sensing of HSO $_{3}^{-}$ and HClO by two different fluorescence signals. The feasibility of QZB in detecting HSO $_{3}^{-}$ in practical food samples was assessed by the method of standard recovery. The results indicated that the probe could be used to quantificationally detect HSO $_{3}^{-}$ in wine, sugar, canned fruit and jasmine tea drinks samples with high recovery between 95.35% and 106.03%.⁹⁵ In Li et al.’s study, a fluorescent probe based on IR-780 was designed to determine HSO $_{3}^{-}$ in crystal sugar and red wine samples with high selectivity and sensitivity.⁹⁶

Fig. 4. (a) Linear relationship between the fluorescence intensity of Dpyt (10 $μ$ M) and HSO $_{3}^{-}$ concentration in sugar and red wine. (b) Measured concentrations of HSO $_{3}^{-}$ in sugar and red wine by Dpyt (10 $μ$ M). Reproduced from Ref. 93 with permission from Elsevier B.V., copyright 2019.

3.3. Detection of hydrogen peroxide

Hydrogen peroxide plays an important role in a wide variety of biological functions of the human body. Due to relative stability and target selectivity, low concentrations of hydrogen peroxide (1–100nM) could regulate a variety of cellular functions, such as proliferation, survival and angiogenesis.⁹⁷ In contrast, hydrogen peroxide at high concentrations (10 $μ$ M or higher) could induce oxidative damage to biomolecules, causing uncontrolled modification of target molecules.⁹⁸ Due to its strong oxidation activity, hydrogen peroxide has a definite effect on a wide range of pathogens, such as coliform organisms and salmonellas.^99,100 Its by-products are water and oxygen, which are nontoxic, ecologically safer and less hazardous to personnel. Therefore, hydrogen peroxide has been used as a disinfectant during food processing for many years. It not only can improve the appearance of foods, but also extend their shelf life. According to the National Standards for Uses of Food Additives of China, hydrogen peroxide could be used in the production process of aquatic products, bagged dried beancurd and raw milk. But hydrogen peroxide residue could not be detected in the finished products.¹⁰¹ However, some food poisoning incident was reported because of excessive hydrogen peroxide residue in milk.¹⁰¹ Herein, considering the potential harm of hydrogen peroxide, a convenient and accurate analysis method for residual hydrogen peroxide is necessary. Tian et al. developed a hydrogen peroxide fluorescent probe TC–BOR by using the hemicyanine and borate as fluorophore and recognition group.¹⁰² The reaction of the probe with hydrogen peroxide would produce the TC–OH. TC–OH could emit fluorescence at 723nm, and its fluorescence intensity was 55-fold higher than that of TC–BOR. The detection limit was 2.27 $μ$ mol/L and the response time was less than 7 min. It could be used in analyzing the content of hydrogen peroxide in various foods such as dried beancurd and bamboo shoots. An ESIPT-based NIR-emitting ratiometric fluorescent probe (HBQ-B) has been constructed by Chen et al. to monitor H₂O₂ (Fig. 5).¹⁰³ In the presence of H₂O₂, the probe molecule undergoes oxidation and 1,6-elimination reactions leading to the fluorophore release and then producing a bright red-shift emission with wavelength from 538 to 656. The probe has been applied to identify intracellular H₂O₂ in living cells and zebrafish. Wang et al. established a new colorimetric NIR fluorescent probe with an acetyl heterocyclic aromatic amine.¹⁰⁴ In response to H₂O₂, the deviation of the identification group of acetyl in the probe would obstruct the ICT process and the fluorescence intensity decrease at 700nm. The probe could be employed to detect endogenous and exogenous H₂O₂ in living cells with a detection limit of 0.85 $μ$ M.

Fig. 5. Chemical structure of HBQ-B and proposed mechanism of HBQ-B for sensing H₂O₂. Reproduced from Ref. 103 with permission from Elsevier Ltd, copyright 2021.

Additionally, some NIR fluorescent probes have also been synthesized to evaluate the antioxidant activity of tea or bioactive compounds. Wang et al. developed a new NIR AIE fluorophore DTPE, which was obtained by incorporating taurine with the fluorophore through a carbamate bond. The probe could be applied as a trackable therapeutic system featuring both imaging esterase-activated taurine release and ROS scavenging.¹⁰⁵ An “off-on” NIR fluorescent probe of CyQ–Cys has been developed in Xiao’s study by nucleophilic substitution. The probe was used to analyze the antioxidant activity of black tea by determining the content of Fe $^{3 +}$ .¹⁰⁶

The unique properties of NIRPs provide excellent opportunities for their use in food field. In this part, we described the potential utilization of NIRPs in food safety detection including heavy metal detection, sulfite analysis and hydrogen peroxide determination. The significant works in recent five years have been summarized in Table 1.

**Table 1. The applications of NIFPs in the food safety detection.**
Probe	Analytes	Wavelength( $λ_{em})$	Detection limit	Working solution	Application	Ref.
Detection of heavy metals
RBLY	Hg $^{2 +}$	695nm	0.34 $μ$ M	EtOH/H₂O (1:5, v/v)	Water, plant cells	77
HMA	Al $^{3 +}$ Cr $^{3 +}$	670nm	Al $^{3 +}$ : 3.26 × 10 $^{- 7}$ MCr $^{3 +}$ : 5.63 × 10 $^{- 7}$ M	DMSO/H₂O (9:1, v/v)	Water	78
Probe 1	Pb $^{2 +}$	670nm	1.65nM	ACN/EtOH/HEPES system (1:1:2, v/v/v)	Water	79
Detection of sulfite
DCQN	HSO $_{3}^{-}$	660nm	24nM	DMSO/PBS (1:9, v/v)	Crystal sugar, yuba, zebrafish	92
Dpyt	HSO $_{3}^{-}$	658nm	—	PBS	Sugar, red wine, fish	93
NIR-BN	SO $_{3}^{2 -}$	680nm	0.17mM	CH3CN/PBS (2:8, v/v)	Crystal sugar, granulated sugar, soft sugar	94
QZB	HSO $_{3}^{-}$ HOCl	655nm	95nM130nM	DMSO/HEPES(5:5, v/v)	Wine, sugar, canned fruit, jasmine tea drinks	95
Probe 1	HSO $_{3}^{-}$ SO $_{3}^{2 -}$	705nm	0.37 $μ$ M	PBS (1% DMSO)	Crystal sugar, red wine	96
Detection of hydrogen peroxide
TC–BOR	H₂O₂	723nm	2.27 $μ$ mol/L	DMSO/PBS (1:9, v/v)	Dried beancurd, bamboo shoots	102
HBQ-B	H₂O₂	656nm	40.2 nM	PBS	Zebrafish	103
HAA	H₂O₂	700nm	0.85 $μ$ M	PBS/DMSO (1:1, v/v)	Living cells	104

4. Conclusion and Perspectives

Food safety is a major public issue around the world, which has been identified as a public health priority by the World Health Organization. Rapid and accurate determination of contaminants in foodstuffs attracts much more attention to safeguarding food safety. Recently, various NIR fluorescent probes have been developed to detect hazardous substances in different foods. This review systematically presents the types and characteristics of NIR fluorescent probes and their potential applications in the detection of heavy metals, sulfite and hydrogen peroxide in food. All endeavors could facilitate the future development of NIR fluorescent probes as highly efficient assay methods for food safety.

Although NIR fluorescent probes have shown great potential in ensuring food safety, the application of the technology in food safety is still in the initial stage. By now, most of the research work on the NIR fluorescent probes mainly focuses on biological imaging. For the future application of NIR fluorescent probes in the detection of food safety, there are still some challenges. First, it is important to eliminate the background signals in food samples, which affects the detection sensitivity and specificity. Second, most of the reported fluorescent probes are used to detect single contaminants in food, which limits their application in food safety detection since different types of food contaminants usually co-exist in food. Finally, affordable and practical probes should be developed to satisfy the market requirements. Therefore, scientists in different fields should work together and endeavor to design highly efficient and versatile NIR fluorescent probes for food safety detection.

Acknowledgments

The work was supported by the National Natural Science Foundation of China (Nos. 81925019, 81801817 and U22A20333), the National Key Research and Development Program of China (Nos. 2023YFB3810000 and 2023YFB3810003), the Fundamental Research Funds for the Central Universities and the Fujian Basic Research Foundation (Nos. 2022J011403, 2023XAKJ0101009, B2302014 and 2020Y4003) and the Program for New Century Excellent Talents in University, China (No. NCET-13-0502).

ORCID

Lei Li https://orcid.org/0000-0002-3529-6353

Gang Liu https://orcid.org/0000-0003-2613-7286

References

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Received 26 August 2024

Accepted 21 November 2024

Published: 15 February 2025

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