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Detection of Metal Ions, Small Molecules and Large Molecules by Near-Infrared Fluorescent Probes

Yuanyuan Liu , Yun Guo , Xiaogang Luo , Genyan Liu , Qi Sun

Progress in Chemistry ›› 2021, Vol. 33 ›› Issue (2) : 199 -215.

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Progress in Chemistry ›› 2021, Vol. 33 ›› Issue (2) : 199-215 DOI: 10.7536/PC200765
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Detection of Metal Ions, Small Molecules and Large Molecules by Near-Infrared Fluorescent Probes
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Abstract

Fluorescent probe analysis, as a rapidly developed analytical method with high sensitivity, good selectivity, and fast responsibility, has been favored in environmental and life science field. And near-infrared fluorescent probe is one of the most developed fluorescent probes. It has been widely employed in detection, tracking and imaging of biomolecules in complex biological systems such as cells and tissues due to its distinguished features including long emission wavelength(600 to 900 nm), low cell damage, strong tissue penetration and low spontaneous fluorescence background. In this review, we summarize the development of near-infrared fluorescent probes in detection and imaging of metal ions(Hg2+, Cu2+, Zn2+, Al3+, Fe3+), small biological molecules(Cys, N2H4, H2S, H2O2), biological macromolecules(Leucine aminopeptidase, β-galactosidase) and other important biological molecules in recent five years. We further give the in-depth discussion on the in vitro and in vivo analytical applications of near-infrared fluorescent probes, and propose their future perspectives.

Contents

1 Introduction

2 Recognition of metal ions by near infrared fluorescent probes

2.1 Fluorescent probes for Hg2+

2.2 Fluorescent probes for Cu2+

2.3 Fluorescent probes for Fe3+

2.4 Fluorescent probes for Al3+

2.5 Fluorescent probes for Zn2+

3 Recognition of small molecules by near infrared fluorescent probes

3.1 Fluorescent probes for Cys

3.2 Fluorescent probes for N2H4

3.3 Fluorescent probes for H2S

3.4 Fluorescent probes for H2O2

4 Recognition of biomacromolecules by near infrared fluorescent probes

4.1 Fluorescent probes for Leucine aminopeptidase

4.2 Fluorescent probes for nucleic acids

4.3 Fluorescent probes forβ-galactosidase

5 Conclusion and outlook

Graphical abstract

Keywords

near-infrared fluorescent probes / metal ions / large molecules / small molecules / bioimaging

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Yuanyuan Liu, Yun Guo, Xiaogang Luo, Genyan Liu, Qi Sun. Detection of Metal Ions, Small Molecules and Large Molecules by Near-Infrared Fluorescent Probes. Progress in Chemistry, 2021, 33(2): 199-215 DOI:10.7536/PC200765

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1 Introduction

In recent years, with the rapid development of life science, people's research on the nature of life activities has gone deep into the cellular, subcellular and biomolecular levels. Studies have shown that intracellular biomolecules, such as cations, small molecules and biomacromolecules, are closely related to cell proliferation, differentiation and apoptosis[1⇓~3]. Their concentration level, spatial and temporal distribution and other characteristics not only play an important role in regulating cell function, but also reflect the physiological and pathological state of cells, tissues and individuals. Therefore, real-time detection, identification and imaging of the concentration and distribution of biomolecules in cells are of great significance for the diagnosis and treatment of diseases[4,5]. Fluorescent probe imaging techniques are widely used in intracellular analytical sensing and optical imaging due to their simplicity, directness, good selectivity, high sensitivity and in situ visualization[6⇓⇓~9].
Minta et al. First synthesized a new type of Ca2+ fluorescent probe in 1989, which opened the prelude of the field of fluorescent probes[9⇓⇓~12]. The classical structure of a fluorescent probe (fig. 1) consists of three parts: (1) a fluorescent dye, which can detect a target molecule by increasing, decreasing, or changing the wavelength of the fluorescent signal when the recognized molecule is present; (2) a recognition group, which can selectively react with a target molecule to achieve the effect of recognition or labeling; (3) a linking group, which can transmit the recognition signal of the recognition group to the fluorescent dye, thereby regulating the output of the fluorescent signal[13,14]. Based on the basic structure of fluorescent probes, fluorescent dyes, as the signal generator of fluorescent probes, greatly affect the recognition effect of fluorescent probe, such as sensitivity, detection limit and optical imaging[15,16]. Common fluorescent dyes include naphthalimides, rhodamines, coumarins, fluoroboropyrroles and cyanines[17][18,23][19][20,21,24][22]. Among them, rhodamine, fluoroborate pyrrole and cyanine near-infrared fluorescent dyes have the advantages of strong tissue penetration (1-2 cm), small cell and tissue damage and low autofluorescence interference due to their long emission wavelength (600-900 nm). Therefore, fluorescent probes based on near-infrared fluorescent dyes are widely used in the identification/detection and fluorescence imaging of biomolecules in cells, tissues and in vivo, and have potential applications in the fields of Bioanalysis and biomedicine[25⇓⇓~28].
In this paper, we review the recent progress in the study of biomolecules,Uch as metal ions (Hg2+[29], Cu2+[30], Fe3+[31], Al3+[32],Zn2+[33]), small biological molecules (Cys, N2H4, H2S,H2O2) and biological macromolecules (Leucine aminopeptidase and beta-galactosidase) and imaging in vivo and in vitro,The physicochemical properties of these NIR probes, such as excitation and emission wavelengths, Stokes shifts, solubility, and quantum yield, are summarized, and their applications in in vivo and in vitro imaging are discussed, as shown in Table 1[34][35][36][37][38][39]. It is expected to provide a reference for the construction of reasonable and efficient near-infrared fluorescence probes through the analysis and summary of the current near-infrared fluorescence probes. In addition, the prospect of its application is also discussed.

2 Recognition of Metal Ions by Near-Infrared Fluorescence Probe

As we all know, metal ions are indispensable elements for life, such as sodium, potassium, magnesium, calcium, iron and so on. These metal ions can coordinate with proteins, nucleic acids, vitamins and hormones to form complexes with important physiological functions, such as metalloproteins and enzymes, which play an important role in life processes. The imbalance of metal ion content can lead to the disorder of normal physiological functions, such as osmotic pressure imbalance and neurological dysfunction[40,41]. Therefore, the qualitative and quantitative analysis of metal ions is conducive to the study of the relationship between metal ions and diseases, and has potential value for disease diagnosis and treatment[42,43].

2.1 Hg2+ probe

Mercury ion (Hg2+) is considered to be one of the most toxic heavy metal ions in the environment, which is widely distributed in water, soil and air[44]. It is easily absorbed by plants and enriched in the human body through the food chain, causing adverse effects and leading to a variety of diseases, including central nervous system defects, arrhythmia, cardiomyopathy and kidney damage[45][46]. Therefore, it is of great significance to develop efficient detection methods for Hg2+ for human health and environmental protection.
Huang et al. designed and synthesized a dual-color near-infrared fluorescence probe DCM-Hg for the detection of Hg2+ (Figure 2)[47]. Based on the strong thiophilicity of mercury, the probe uses 1,3-dithiane as a recognition group and dicyanomethylene-4H-pyran (DCM) as a fluorophore, and realizes the detection of the Hg2+ through a thioacetal deprotection reaction triggered by the Hg2+. When the DCM-Hg probe was added to the mixed solution of PBS and DMSO with the volume ratio of 1 ∶ 1, the absorption spectrum of the probe showed a slight blue shift, the fluorescence intensity increased significantly, and the color of the solution changed from purple to pink, so it could be used as a test paper for detecting Hg2+ by naked eyes. The probe DCM-Hg has high sensitivity to Hg2+ with a detection limit of 6.8×10-8mol/L. In addition, DCM-Hg has low cytotoxicity and good cell penetration, and can be used for NIR fluorescence imaging of Hg2+ in living cells. The successful development of DCM-Hg provides a simple and efficient method for the detection of Hg2+ in environmental and living systems, which shows its potential application value in environmental and biological fields.
Due to the strong absorption and emission properties of cyanine dyes in the near-infrared region, Yuan et al. Designed and synthesized a new near-infrared fluorescent probe Cy-PT (Fig. 3) using hemicyanine derivatives as fluorophores[48]. The addition of Hg2+ to the mixed solution of DMSO and HEPES with a volume ratio of 2:8 triggered the hydrolysis of the thiocarbonate portion of Cy-PT, resulting in a significant increase in fluorescence. At the same time, the fluorescence titration experiment showed a good linear relationship, which laid the foundation for the quantitative detection of Hg2+ in vitro. The detection limit of Cy-PT was 0. 18 μmol/L, showing high sensitivity. In addition, Cy-PT has been successfully used for fluorescence imaging in living cells and zebrafish.
Obviously, these near-infrared fluorescent probes can only show good detection performance in a large number of organic solvent environments, which greatly limits their wide application in biology. Therefore, in order to obtain a near-infrared fluorescent probe suitable for detecting Hg2+ in biological samples under physiological conditions, Wang et al. Designed and synthesized a novel near-infrared fluorescent probe CY1OH2S based on a hemicyanine dye (fig. 4)[49]. In HEPES buffer solution, the dithioacetal deprotection reaction between the probe and the Hg2+ occurred, and the fluorescence intensity at 710 nm was enhanced.The probe showed good selectivity and high sensitivity to the Hg2+, and its detection limit was as low as 0. 32 μmol/L. In addition, the probe CY1OH2S has low cytotoxicity and good cell penetration, and is more suitable for fluorescence imaging of living cells and complex biological tissues.

2.2 Cu2+ probe

Cu2+ is the third most abundant transition metal ion in the human body, and it is also an important trace element in the human body, which plays an important role in many cellular processes such as gene expression, protein function and structural enhancement[76]. Abnormal levels of Cu2+ in living organisms lead to oxidative stress and neurological diseases, including Alzheimer's disease, Parkinson's disease, Menkes disease (copper deficiency) and Wilson's disease (copper excess)[77,78]. Therefore, the detection of Cu2+ is of great significance to life activities.
In 2017, Guo et al. designed and synthesized a near-infrared fluorescent probe NIR-Cu (Figure 5) for the detection of Cu2+, which uses cyanine dye Cy7 as the fluorophore and 1,4,8,11-tetraazacyclotetradecane as the specific receptor of Cu2+[50]. Free NIR-Cu showed weak fluorescence, but it had a strong affinity for Cu2+, and the fluorescence increased after binding. With the increase of the concentration of the Cu2+, the maximum emission intensity of the NIR-Cu probe decreases gradually at 778 nm, and a new peak is formed at 636 nm. The Stokes shift of up to 142 nm in the emission spectrum makes the emission peaks before and after the Cu2+ treatment clearly separated, so that a useful ratio measurement can be made. The ratio type probe can show a larger fluorescence ratio change by measuring the fluorescence intensity of two wavelengths from a short wavelength region to a long wavelength region, so as to avoid the interference of the self-fluorescence background of biomolecules in a biological system and provide a built-in correction for environmental effects. NIR-Cu has high sensitivity and good selectivity to Cu2+, and more importantly, the cell imaging is consistent with the ratio fluorescence response induced by Cu2+, so the NIR-Cu probe can be used for ratio fluorescence imaging of Cu2+ in living cells.
According to the current literature, most of the fluorescent probes for Cu2+ are quenched, which is not conducive to the detection of Cu2+. Rhodamine dyes have a unique spiro "on-off" property, that is, the structural change from a spiral ring state (non-fluorescent state) to an open ring state (fluorescent state), and the synthesized probe belongs to a fluorescence enhanced type, and compared with a fluorescence quenching type, the probe has the advantages of small background interference, high sensitivity and the like. Based on this, Li Ge et al. Synthesized the near-infrared fluorescent probe NRh-Cu (fig. 6) through the reaction of aniline and rhodamine[51]. The fluorescence of the probe solution was weak and colorless.After the addition of Cu2+, the absorbance at 717 nm increased significantly and the probe solution turned green, which indicated that NRh-Cu reacted with Cu2+ to form a ring-opened amide. Compared with other Cu2+ probes, the probe has higher sensitivity and selectivity and lower background interference. The Cu2+ imaging of NRh-Cu in cells was studied by confocal luminescence microscopy, and the results showed that NRh-Cu had good cell membrane permeability, could be localized to cells, and could realize the detection of Cu2+ in cells. NRh-Cu has potential biological application value in the application of real-time monitoring the change of Cu2+ content level in cells.
Recently, Li et al. Designed and synthesized a small molecule near-infrared fluorescent probe DCM-Cu (fig. 7) based on DCM fluorophore for the detection of Cu2+[52]. The fluorescence intensity of DCM-Cu was linear with the concentration of Cu2+ at 700 nm, and the detection limit of DCM-Cu was 2.54×10-8mol/L. DCM-Cu has been successfully used to detect Cu2+ in MCF-7 cells and tumor tissues. Therefore, DCM-Cu has the potential to monitor the Cu2+ of cells in living systems and can be used for the diagnosis of related diseases.

2.3 Fe3+ probe

Iron ion is the most abundant and essential transition metal ion in living systems, which plays an important role in various physiological processes, such as oxygen uptake, muscle contraction, neurotransmission, enzyme catalysis, nucleic acid synthesis and cell metabolism[79,80]. Deficiency of Fe3+ in the body (low iron) can lead to low blood pressure, iron deficiency anemia and other diseases, while excess (high iron) can lead to skin pigmentation, Alzheimer's disease and Parkinson's disease[81]. In addition, Fe2+ and Fe3+ are prone to oxidation-reduction reactions in the presence of oxygen, which can lead to tissue damage and serious complications[82,83]. Therefore, it has become an urgent need in the field of biology to use sensitive analytical methods to monitor the concentration of Fe3+ in organisms.
The probe with rhodamine as the dye can detect the Fe3+ in water or semi-aqueous medium, and can also detect the Fe3+ in living cells. Based on this, Gu et al. Developed a new fluorescent probe RHCC based on rhodamine derivatives and hybrid chromic cyanic acid (Fig. 8)[53]. RHCC has the structure of spironolactone, which has no fluorescence. When RHCC combines with Fe3+, the spironolactone ring is opened and hydrolyzed to produce a substance with red fluorescence. Compared with other probes, RHCC has higher accuracy and sensitivity in identifying Fe3+. In the MTT assay, the RHCC probe showed very low cytotoxicity, which laid the foundation for cell imaging and in vivo imaging. Cell and zebrafish imaging experiments showed that the probe could measure the concentration of Fe3+ in cells and zebrafish.
Hu et al. designed and synthesized a novel rhodamine-based near-infrared fluorescent probe B-1 (fig. 9)[54]. Different from the typical rhodamine dye probe, B-1 has a strong fluorescence enhancement effect on the Fe3+. In pure water solution, after interaction with the Fe3+, the ring-opening hydrolysis of spirolactam occurs, and the solution can be directly observed from colorless to pink, with a significant fluorescence enhancement (about 500 times). In addition, the near-infrared fluorescence probe has high selectivity for Fe3+ and has been used for fluorescence imaging of Fe3+ in living cells. In cells, B-1 showed good biocompatibility and low toxicity, and good dispersibility in water. Therefore, B-1 is a highly sensitive and selective near-infrared fluorescence probe for the detection of Fe3+.

2.4 Al3+ probe

Aluminum is the most abundant metal element in the earth's crust. It is widely used as a storage or cooking tool in daily life, which leads to the increase of Al3+ concentration in food and the probability of human body absorbing Al3+[84][85,86]. However, Al3+ is not an essential element for life. Excessive Al3+, especially in the brain, can damage the central nervous system and cause a series of diseases, such as Parkinson's disease, Alzheimer's disease, dialysis encephalopathy and osteoporosis[87]. Therefore, accurate identification and detection of intracellular Al3+ content is of great significance for biological research and clinical diagnosis.
Xie et al. Developed a new near infrared rhodamine spirochete amino fluorescent probe, NIR-Rh, for the detection of Al3+ (fig. 10)[55]. In this near infrared fluorescence probe, Fisheraldehyde is introduced into the structure of rhodamine dye to extend the absorption and emission wavelengths and thereby convert to a strong fluorescent structure. NIR-Rh also showed a significant fluorescence enhancement response to Al3+, and the fluorescence intensity increased by 77 times when the concentration of Al3+ increased to twice that of the original, indicating that the probe had high sensitivity to Al3+. In addition, live cell and tissue imaging experiments have further demonstrated its potential in practical applications.
The emission intensity of the fluorescent probe is affected by many factors, including the concentration of the fluorescent probe, the excitation intensity, and the detection efficiency. The ratio fluorescence probe can eliminate the influence of the above factors through self-calibration, and a more accurate ratio can be obtained by measuring the fluorescence intensity at two different emission wavelengths. Chen et al. designed and synthesized a ratio near-infrared fluorescent probe BTZ-SF (fig. 11). BTZ-SF showed good selectivity for Al3+, and showed significant blue shift of fluorescence after binding with Al3+[56]. In the range of 0 ~ 100 μmol/L, the fluorescence intensity ratio (I476 nm/I568 nm) showed a good linear relationship with the concentration (R2=0.9911), and the detection limit was 2. 2 μmol/L. At the same time, BTZ-SF has a good imaging effect on Al3+ in HeLa cells through fluorescence microscopy imaging, which has potential application value.

2.5 Zn2+ probe

Zinc ion is considered to be the second most abundant transition metal ion in human body after iron ion, which plays an important role in many biological processes such as gene expression, nerve signal transmission, DNA binding and recognition[88][89]. Moderate zinc is beneficial to human health, but abnormal zinc ion levels can lead to a variety of diseases, such as hypoglycemia, Alzheimer's disease, Parkinson's disease, epilepsy and cerebral ischemia[90⇓~92]. Therefore, in order to understand the role of zinc ions in pathology, physiology and toxicology, it is very important to develop sensitive and selective detection tools for zinc ions.
Dicyanoisophorone dyes have the advantages of large Stokes shift, near-infrared radiation, good photostability and low toxicity. Zhang et al. designed and synthesized a near-infrared fluorescence probe YPT based on dicyanoisofurone derivatives for rapid detection of Zn2+ (fig. 12)[57]. The probe has a low detection limit (12 nmol/L) and a large Stokes shift (168 nm) for Zn2+. Free YPT has a maximum absorption peak at 434 nm, but when Zn2+ is added to the YPT solution, the maximum absorption peak has a red shift to 502 nm, and the ratio of absorbance is proportional to the concentration of Zn2+. In addition, the probe YPT has good selectivity for Zn2+, and the excellent detection performance of YPT makes it a probe for monitoring Zn2+ in the nanomolar range. Importantly, the probe can also be used to detect the release of Zn2+ in cells, and after incubation with Zn2+, it shows strong and bright fluorescence, indicating that the YPT probe can be used for fluorescence imaging of Zn2+ in living cells.
Zhang et al. Reported a highly sensitive detection of Zn2+ by NR-Zn, a near-infrared fluorescent probe (fig. 13)[58]. The probe shows very weak and imperceptible fluorescence in the absence of a Zn2+, and a chelation reaction occurs when a Zn2+ is added, and the fluorescence is significantly enhanced when excited at 545 nm. NR-Zn has the advantages of low detection limit (0. 44 μmol/L), fast response (less than 20 s) and large Stokes shift (131 nm). The probe has high selectivity, low cytotoxicity and good photostability for Zn2+. NR-Zn can monitor the concentration of Zn2+ in HeLa cells in real time, which shows its value in vivo and clinical application.

3 Recognition of Small Molecules by Near-Infrared Fluorescent Probe

Small biological molecules such as cysteine (Cys), hydrazine (N2H4), hydrogen sulfide (H2S) and hydrogen peroxide (H2O2) are important signaling molecules in the human body, and their quantity, quality and structural composition are closely related to human health[93,94]. Therefore, the development of analytical tools for the detection of small biological molecules is of great significance for the study of physiological and pathological mechanisms.

3.1 Cysteine probe

Cysteine (Cys), as an important sulfhydryl biomolecule, plays an important role in protein synthesis, signal transduction and post-translational modification, but its abnormal level has been confirmed to be closely related to many diseases.Uch as liver injury, somnolence, neurotoxicity, growth retardation, hematopoiesis disorders, skin lesions and neurodegenerative diseases, so it is very important to detect the concentration of Cys in vivo[95⇓~97][98]. However, the chemical structure and reactivity of Cys are similar to other biological thiols, such as glutathione (GSH) and homocysteine (Hcy), which makes the specific recognition of Cys in biological systems face great challenges[99]. Therefore, it is of great significance to develop an effective and specific method for the detection of Cys for the diagnosis and treatment of related diseases.
Zhang et al. designed and synthesized a novel near-infrared fluorescent probe Cys-WR with a large Stokes shift (fig. 14)[59]. The near-infrared fluorescent probe uses fluorophore WR-4 as a fluorescent reporter group, and uses crotonic acid ester to detect amino acid fragments. The use of near-infrared emitted fluorescence can reduce cell damage, eliminate background autofluorescence, and increase tissue penetration depth, thereby improving imaging accuracy.
Before cell imaging, the cytotoxicity of A549 cells was detected by CCK-8, and the results showed that the cytotoxicity of the probe was very small and could be used for biological imaging. The endogenous and exogenous Cys of living cells were then imaged with the probe under a fluorescence microscope. After A549 cells were incubated with the probe for 30 min, significant red fluorescence was observed. As a control, A549 cells showed very weak red fluorescence after incubation with the probe for 30 min after removal of intracellular Cys in NEM. The cells were pretreated with NEM, then treated with Cys, and finally incubated with the probe, resulting in strong red fluorescence.
Subsequently, the visualization of Cys in vivo was studied using zebrafish as a model. Incubation of the zebrafish with the probe produced intense red fluorescence from the ventral fin to the pectoral fin (the visceral area of the zebrafish). In the control experiment, the red fluorescence of zebrafish treated with NEM before probe incubation was significantly reduced. In addition, the red fluorescence signal of zebrafish was significantly enhanced when the zebrafish were pretreated with NEM and then incubated with probe and Cys. The experimental results show that the probe can penetrate cells and successfully image Cys in living cells and zebrafish, which is of great significance in biological imaging research.
Qi et al. designed and synthesized a selective near-infrared fluorescent probe CP-NIR for the detection of Cys (Figure 15). After Cys was added to DMSO-PBS solution, Cys would undergo conjugated addition and intramolecular cyclization reaction with the acrylate group of the probe.The generate lactam is cleaved from that molecule, thereby restore the fluorescence of the DCM fluorophore, the absorption wavelength of the DCM fluorophore is red-shifted from 550 nm to 600 nm, and the near-infrared fluorescence emission around 760 nm is obviously enhanced[60]. The probe also has large Stokes shift (160 nm), low detection limit (48 nmol/L), short response time and low toxicity. This near-infrared probe with good cell penetration has been successfully applied to endogenous Cys monitoring in living cells and mouse models, which is of great significance.
Cai et al. reported a lysosome-targeting near-infrared fluorescent probe, SHCy-C, based on a luminescent thiophene-indoline dye (fig. 16)[61]. The probe has higher selectivity and sensitivity for the detection of Cys, and the lowest detection limit for Cys is 31 nmol/L. After reacting with Cys in a C2H6O-PBS solution, the charge of the cationic Cys probe is transferred, the fluorescence is enhanced, the color change is visible to naked eyes, and the ultraviolet spectrum has a larger wavelength shift, so that the cationic Cys probe can be used for high-selectivity detection of Cys. More importantly, we found that the SHCy-C probe can accurately target lysosomes and successfully apply it to the fluorescence imaging of endogenous Cys in living cells. The probe SHCy-C becomes a precise and effective tool for Cys detection.

3.2 Hydrazine (N2H4) probe

Although N2H4 has a wide range of applications in industry, agriculture, medicine, military and aerospace, it is a toxic biological molecule[100,101]. Human exposure to high concentrations of hydrazine can irritate the eyes, nose and throat, cause temporary blindness, dizziness, nausea, pulmonary edema, coma, blood abnormalities and, in severe cases, damage to the liver, lungs, kidneys and central nervous system[102⇓⇓~105]. Therefore, the detection of N2H4 in vivo and in vitro has attracted much attention.
Our group designed and synthesized a new near-infrared fluorescence probe Cy-WR to detect N2H4 (Figure 17)[62]. The probe is superior to most of the N2H4 fluorescent probes reported at present, which is mainly manifested in the following aspects: (1) the probe has good water solubility in 99.9% PBS solution and does not need to use a large amount of organic cosolvent; (2) shows good selectivity to N2H4, does not cause any ultraviolet or fluorescence reaction to other organic amines (including methylamine, ammonia, morpholine and aniline), and can well distinguish hydrazine from other organic amines (Figure 18); (3) has a D-a type structure, and has good light absorption and light emission characteristics in the near infrared region, which can overcome the shortcomings of most of the current "off-on" or “on-off”N2H4 probes. In addition, the Cy-WR probe imaged Cys in living cells (fig. 19) as well as in zebrafish (fig. 20) with a significantly reduced red fluorescence signal, indicating that the Cy-WR probe can be used for real-time and ratiometric imaging of N2H4 in cells and zebrafish, and therefore has potential value for further investigation of various biological samples.
Wu et al. designed and synthesized a ratiometric near-infrared fluorescent probe DXM-OH (fig. 21) for the specific detection of N2H4[63]. The detection limit of the probe was 0. 09 μmol/L for N2H4, and the near-infrared fluorescence intensity decreased and the yellow fluorescence intensity increased with the addition of N2H4 in DMSO-PBS solution.Therefore, DXM-OH can be used to detect the near-infrared ratio fluorescence signal of N2H4. DXM-OH can be used not only for the detection of N2H4 in water samples, but also for the imaging of N2H4 in LO2 cells (human normal liver cells). DXM-OH provides a sensitive tool for the detection of N2H4 in environmental and biological samples.

3.3 Hydrogen sulfide (H2S) probe

H2S is a gaseous substance produced by geological and microbial activities, which has a unique odor of rotten eggs and can irritate the eyes and respiratory tract. For centuries, H2S has been considered a toxic chemical[106⇓~108]. However, more and more evidences show that H2S also plays an important role in many physiological and pathological processes, such as protecting cardiovascular system (relaxing vascular smooth muscle and lowering blood pressure), regulating cell growth, regulating blood pressure and inhibiting insulin signal transduction. It is considered to be the third important gas in life system[109⇓~111]. As a ubiquitous and physiologically relevant signaling molecule, the abnormal concentration of H2S can lead to a variety of diseases, including Alzheimer's disease, Down's syndrome, diabetes and cirrhosis[112,113]. Therefore, it is very important to develop a method to detect H2S in living cells or tissues.
Jiang et al. designed and synthesized a new mitochondria-targeted near-infrared fluorescent probe (Mito-NIR-SH) (fig. 22) for the detection of H2S in living cells, which was designed and synthesized by using 2,4-dinitrobenzene as a fluorescence quenching group to introduce the part of the H2S reaction into the near-infrared fluorophore (CS-OH)[64]. Compared with the previously reported near-infrared fluorescent probe for opening mitochondria targeting, the near-infrared fluorescent probe has better chemical stability, faster response speed to H2S, lower detection limit and higher selectivity, and is successfully applied to near-infrared biological imaging experiments of H2S in living cells.It was confirmed that Mito-NIR-SH had good membrane permeability and could target the mitochondria in cells, which could monitor the exogenous and endogenous H2S in cells and was a very useful molecular detection tool.
In 2019, Huang et al synthesized a new near-infrared fluorescent probe DBT (fig. 23) for the detection of H2S in colon cancer cells[65]. With triphenylamine and BODIPY as the fluorophore and 2,4-dinitrosulfonyl as the reaction site, the DBT probe has the characteristics of fast response (within 150 s), significant near-infrared emission (716 nm), low detection limit (6. 74 nmol/L), high sensitivity and good selectivity for H2S, which is conducive to real-time monitoring and imaging of intracellular H2S. More importantly, fluorescence confocal studies showed that HCT116 cells showed very strong fluorescence after incubation with H2S and DBT, indicating that DBT probe was successfully applied to fluorescence imaging of endogenous H2S in cells and was a tool for detecting H2S in solution and living cells.
Xi et al. reported a near-infrared fluorescence probe NBD-SH (Fig. 24) with rhodamine derivative as fluorophore. After the probe reacts with H2S in DMSO-PBS solution, the fluorescence at 660 nm is enhanced by 10 times, and the fluorescence quantum yield of the product can reach 0.29[66]. NBD-SH showed high selectivity and sensitivity for H2S with a detection limit of 0. 27 μmol/L. In addition, NBD-SH has cell membrane permeability and mitochondrial targeting, and can be used for imaging endogenous H2S in living cells. Therefore, the red-shifted fluorescent probe can be used as a useful tool for H2S biological research.

3.4 Hydrogen peroxide (H2O2) probe

As an important reactive oxygen species (ROS), H2O2 (ROS) acts as the second messenger in normal cell signal transduction, participates in cell growth, proliferation and differentiation, and plays an important role in both physiological and pathological conditions[115,116][114]. However, the abnormal concentration of H2O2 can lead to a variety of diseases. High concentration of H2O2 can cause apoptosis and necrosis, resulting in oxidative stress and damage[117,118]. Therefore, the development of a method that can accurately detect the concentration of H2O2 in cells is essential for the study of its role in physiological and pathological conditions.
Xiong et al. designed and synthesized a new H2O2 specific fluorescent probe DCM-AC (fig. 25), which uses acetyl as a recognition group and shows a significant fluorescence enhancement signal in the near-infrared region after H2O2 treatment[67]. The selectivity of DCM-AC for H2O2 is better than that of other interfering substances, which is very important for the detection of H2O2. In addition, DCM-AC can also be used for fluorescence imaging of H2O2 in living cells. The application of DCM-AC in vivo imaging of intratumoral H2O2 also demonstrates its potential for tumor diagnosis. Therefore, DCM-AC can not only be used as an effective tool to track the pathological reactions related to H2O2 in living systems, but also be used to construct new fluorescent probes for H2O2 by adding new acetyl recognition groups to other fluorophores.
Diao et al. designed and synthesized a near-infrared fluorescent probe NRBE (Figure 26) with good water solubility by using phenylborane as a recognition group. In PBS buffer solution, the probe reacts with H2O2, the phenylborane is oxidized and released, and the fluorescence of the probe is rapidly enhanced. The response time is less than 15 min, with a high quantum yield (0.36) and a detection limit of 75 nmol/L for H2O2[68]. Therefore, the endogenous H2O2 produced by the human liver cancer cells can be detected, and the generation of the H2O2 in the ischemia-reperfusion process can be captured through cell imaging. The fluorescent probe NRBE is an effective tool for real-time detection of H2O2 in cells.
Huang et al. designed a Cy-H2O2 probe for real-time monitoring of H2O2 in vivo by benzyl modification of the near-infrared hemicyanine backbone (fig. 27)[69]. In methanol-water solution, Cy-piperazine reacts with H2O2, resulting in benzene rearrangement, decarboxylation and dehydration.The fluorescence intensity of Cy-piperazine at 578 nm is linear with the concentration of H2O2 (0-7 μmol/L), and the detection limit is 65 nmol/L. In addition, the Cy-H2O2 probe has been successfully applied to the detection of H2O2 in living cells and zebrafish.

4 Recognition of Biomacromolecules by Near-Infrared Fluorescent Probe

Macromolecules also play an important role in biological processes, such as leucine aminopeptidase (LAP) and β-galactosidase, which play an important role in maintaining redox homeostasis of proteins, cells and organisms, but abnormal levels of these molecules have also been confirmed to be closely related to the occurrence of cancer[119,120]. Therefore, it is of great significance to design and develop high-selectivity and high-sensitivity biomacromolecule detection tools.

4.1 Leucine aminopeptidase (LAP) probe

LAP is an important protease widely found in mammals, plants, microorganisms and living cancer cells, which can selectively catalyze the hydrolysis of leucine residues of proteins or polypeptides and play an important role in many physiological and pathological processes. Abnormal expression of LAP is associated with a variety of diseases, such as ovarian epithelial malignancies and breast cancer. Therefore, the development of an effective method for monitoring LAP activity in living systems will provide an important reference for the diagnosis and treatment of cancer[121].
So far, some LAP near-infrared fluorescent probes have been developed, but there are still some problems, such as they can not be widely used in the detection and imaging of biomolecules in complex biological systems such as cells and tissues. Based on this, our research group designed and synthesized a new near-infrared fluorescent probe (BODIPY-C-Leu) (Figure 28), which uses asymmetric BODIPY dye as the fluorescent group and leucine as the recognition group[70]. When BODIPY-C-Leu reacts with LAP, the amide bond in the dipeptide is broken, a free amino group is released, and the residue undergoes intramolecular rearrangement. Through the interconversion between sulfur and nitrogen atoms, the sulfur-substituted BODIPY is converted into amino-substituted BODIPY, which changes the optical properties of the probe and enhances the fluorescence intensity for specific detection of LAP in vivo and in vitro (fig. 30). In addition, BODIPY-C-Leu also has good cell membrane permeability and can be applied to cell imaging (fig. 31). More importantly, BODIPY-C-Leu achieved the first detection of endogenous LAP activity in living zebrafish (fig. 29). The discovery of this probe provides a new choice for the detection of LAP in complex biological environment, and makes an important contribution to better understanding the activity of endogenous LAP in living samples.
In order to better detect LAP in complex biological environment, Zhang et al. designed and synthesized a new near-infrared fluorescent probe TMN-Leu for the first time (Fig. 32)[71]. The probe has ultra-high sensitivity, low detection limit (0. 38 ng/mL), large Stokes shift (198 nm), good water solubility, good specificity, good cell membrane permeability and low toxicity, has remarkable near-infrared emission (658 nm) to LAP, and can effectively detect trace LAP activity in cells.
In order to be able to quantitatively detect the distribution and dynamic changes of LAP, Gu et al. reported a targeted near-infrared fluorescent probe DCM-Leu (fig. 33) with DCM as the fluorophore and L-leucine as the recognition group, which was used to quantitatively detect LAP activity in different living cells[72]. DCM-Leu has a large Stokes shift (205 nm), the fluorescence intensity at 660 nm is linearly related to the concentration of LAP (R2=0.998), and the lowest detection limit for LAP is 46 ng/mL (Figure 34). In addition, DCM-Leu has good cell membrane permeability and little cytotoxicity. They studied the performance of the probe in several living cells using confocal laser scanning microscopy (fig. 35). Under the same experimental conditions, QSG-7701 cells had weak fluorescence in both green and red channels.In contrast, SMMC-7721 cells showed a decreased fluorescence signal in the green channel and an increased fluorescence signal in the red channel, and the fluorescence in the red channel was significantly decreased after the addition of bestatin (LAP inhibitor), indicating that SMMC-7721 cells had a high level of LAP activity. To further validate the experimental results, they chose to incubate HeLa cells with high endogenous LAP levels with DCM-Leu. As expected, clear near-infrared fluorescence was initially detected in the cells, and then fluorescence was blocked in the presence of bestatin. Therefore, DCM-Leu can be used as an efficient biological probe for quantitative monitoring of endogenous LAP activity.

4.2 Beta-galactosidase

β-galactosidase is an essential hydrolase, which can cleave the glycosidic bond of β-galactoside to form monosaccharides, and degrade residues from gangliosides, sphingolipids, glycoproteins and keratin sulfate[122]. It has been proved that the abnormal level of β-galactosidase is related to cell aging and the development of primary ovarian cancer[122,123]. Therefore, it has become an urgent need in the field of biology to develop efficient detection methods to detect and image the activity of β-galactosidase in organisms.
Zhang et al. designed and synthesized a novel β-galactosidase near-infrared fluorescent probe (Gal-Pro) based on the cysteine backbone and coupled to the D-galactose residue via a glycosidic bond (Figure 36)[73]. As a substrate of β-galactosidase, the probe showed a rapid and sensitive fluorescence enhancement reaction to β-galactosidase in aqueous solution. By detecting β-galactosidase in living cells, it was found that the probe showed a strong fluorescence signal in senescent cells, but not in normal cells, which indicated that the probe could successfully detect aging-related β-galactosidase in living cells.
Since β-gal is a typical lysosomal glycosidase, lysosome-specific probes are a more efficient tool for β-gal detection and imaging. Li et al. designed and synthesized Lyso-gal (fig. 37), a near-infrared fluorescent probe with lysosome targeting capability, for the detection and imaging of endogenous β-Gal in ovarian cancer cells (SKOV-3 cells)[74]. Lyso-Gal showed weak fluorescence in aqueous solution.After the addition of β-Gal, the galactoside group of Lyso-Gal was cleaved and the phenolic hydroxyl group was removed, resulting in the emission of bright near-infrared fluorescence at 725 nm. There was a good linear relationship between the absorbance of the probe and the concentration of β-gal (0 ~ 2 units/mL), and the detection limit was 0. 022 units/mL. After 15 min of incubation, the fluorescence signal of SKOV-3 cells was much brighter than that of control cells (Fig. 38). Therefore, Lyso-gal can be used as a reliable probe for the specific detection of β-Gal in ovarian cancer cells. In addition, the luminescence process of probe Lyso-Gal in SKOV-3 cells was dynamically monitored (Figure 39), and highly selective imaging of ovarian cancer cells could be achieved by incubating Lyso-Gal for 1 min, and the detection time was very short. Lyso-gal has the characteristics of high sensitivity, good selectivity and low toxicity, so it has great potential in the detection of ovarian cancer cells β-Gal. Implanting this functional probe into subcellular organelles is expected to provide more accurate imaging for ovarian cancer cells.
Wei et al. designed a near-infrared fluorescent probe DP-GLU (fig. 40) with dicyanoisofurone as the fluorophore, which can accurately detect β-Gal in living cells[75]. In acetonitrile-water solution, it reacts with β-Gal and shows a rapid and strong emission at 676 nm with a Stokes shift of 131 nm. DP-GLU also showed high sensitivity to β-Gal with a detection limit as low as 1.45×10-2μg/L. In addition, DP-GLU can be used to distinguish tumor cells from normal cells and reveal a noninvasive tracking function of β-Gal levels in a mouse tumor model. Therefore, DP-GLU has great application potential in the early diagnosis and treatment of cancer.

5 Conclusions and outlook

In this paper, the latest research progress of near-infrared fluorescence probes (2016-2020) is reviewed, and the design strategies, sensing mechanisms and interaction modes of near-infrared fluorescence probes are discussed.Special attention is paid to the application of near-infrared fluorescent probes in biological imaging.
Near-infrared (NIR) fluorescence probes have the advantages of high sensitivity, extremely low background interference, low autofluorescence intensity and can be used for biological imaging.However, with the deepening of research, biological fluorescence imaging technology has put forward higher requirements for the development of new small molecule fluorescence probes, and the development of NIR fluorescence technology is still facing enormous challenges. For example, dyes still have many limitations. Although BODIPY dyes have the advantages of easy modification of structure and high solubility in various organic solvents, BODIPY ion probes,The detection sensitivity and selectivity of anions are far less than those of cations, and the quantum yield is low, which to some extent limits the deeper application of this fluorescent dye in the field of biology. Although rhodamine dyes have high fluorescence quantum yield and molar extinction coefficient, the absorption and emission wavelengths of a small number of rhodamine derivatives are less than 600 nm, which limits their application in tissue and in vivo imaging. Therefore, there is also a need to design fluorophores with excellent chemical and photochemical properties, such as high quantum yield, large Stokes shift, and high photostability, for near-infrared fluorescent probes.
Current probes are not ideal for complex tissue detection, such as the detection of intracellular viscosity. Due to the diversity of different organelles, the high heterogeneity of intracellular microenvironment and the large regional differences of viscosity, in order to better show the changes of intracellular microenvironment, intracellular viscosity should be measured in specific organelles, rather than in the whole cytoplasm. However, traditional near-infrared fluorescence probes have many limitations in accurately monitoring the viscosity of living cells in specific organelles[124].
Fluorescence imaging has become a basic tool for biomedical applications, but most of the fluorescent materials still have some limitations, such as low response times, short emission wavelength, strong fluorescence background and so on. Near-infrared region 2 greatly overcomes these problems faced by traditional fluorescence, reduces photon scattering, and can produce higher signal-to-noise ratio, better spatial and temporal resolution, and deeper tissue penetration in vivo imaging, which is expected to open up a new field for the development of new near-infrared fluorescence probes.

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Funding

National Natural Science Foundation of China(21807082)

Special Projects of the Central Government in Guidance of Local Science and Technology Development in Hubei Province(2020ZYYD040)

second batch of the Key Research and Development Project of Hubei Province(2020BAB073)

Science and Technology Research Project of Hubei Provincial Department of Education(T201908)

Science and Technology Research Project of Hubei Provincial Department of Education(Q20171503)

Teaching Research Project of Hubei Province(2017327)

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