Monoamine oxidase inhibitor type near-infrared fluorescent probe, synthetic method thereof and application of monoamine oxidase inhibitor type near-infrared fluorescent probe in photothermal therapy

Abstract

The invention discloses a monoamine oxidase inhibitor type near-infrared fluorescent probe, a synthesis method thereof and application of the monoamine oxidase inhibitor type near-infrared fluorescent probe in photothermal therapy of tumors. The method comprises the following steps: (1) synthesizing the monoamine oxidase inhibitor type near-infrared fluorescent probe SINH; and (2) applying the SINH probe to monoamine oxidase activity inhibition, organelle co-localization imaging and targeted phototherapy tumor treatment. The problem that a traditional inhibitor type probe only targets tumors and does not combine with illumination for phototherapy is solved; the inhibitor type near-infrared fluorescent probe has near-red absorption and emission properties, so that interference of background fluorescence signals can be weakened, and the tissue penetration depth can be increased; the probe disclosed by the invention not only has strong inhibition on the growth of SH-SY5Y cells with high MAO expression, but also can be used for carrying out photodynamic and photothermal therapy on subcutaneous tumor-bearing mice with high MAO expression, and has a very good inhibition effect on the growth of tumors with high MAO expression.

Description

Technical Field

[0001] The invention relates to a monoamine oxidase inhibitor type near-infrared fluorescent probe, a synthesis method thereof and application in phototherapy, and belongs to the technical field of fluorescent probes. Background Art

[0002] Cancer is an extremely aggressive disease with high morbidity and mortality rates, primarily due to the uncontrolled growth and division of cancer cells. Therefore, accurately detecting the presence and characteristics of tumors is crucial. Compared to traditional imaging techniques, fluorescence bioimaging can capture molecular information about tumor structure and metabolic processes. Through the recognition capabilities of optical probes, fluorescent signals are activated and multicolor imaging is achieved, resulting in a high signal-to-noise ratio. This technology offers numerous advantages, including low invasiveness, low toxicity, real-time performance, and visualization. However, single diagnostic or therapeutic approaches often lag in cancer treatment, leading to the integration of diagnosis and treatment into a new trend in cancer treatment. Leveraging the advantages of fluorescence imaging, researchers have combined fluorescence imaging with other therapeutic approaches to develop a variety of fluorescent probes with both diagnostic and therapeutic capabilities. For example, responsive fluorescent probes have been used in photodynamic therapy for early-stage superficial cancers. In recent years, the research and development of fluorescent materials has significantly advanced the development of light-mediated tumor therapies, such as photothermal therapy (PTT) and photodynamic therapy (PDT). These two therapies kill tumor cells by light-exciting photosensitizers to produce reactive oxygen species (ROS) and high heat, respectively. They have the advantages of high selectivity, good safety, little damage, and no drug resistance, and play an important role in tumor treatment.

[0003] Monoamine oxidase (MAO) is a flavin adenine dinucleotide (FAD)-dependent enzyme, primarily divided into two isoforms, MAO-A and MAO-B. It is primarily located in the outer mitochondrial membrane and participates in amine metabolism in the human body. It oxidizes monoamines produced during metabolic processes and exogenous monoamines into their corresponding aldehydes, generating hydrogen peroxide (H2O2). In the human body, MAO plays a key role in maintaining neurotransmission homeostasis. Recent studies have linked MAO not only to psychiatric disorders but also to various cancers. For example, during prostate cancer metastasis to bone and viscera, MAO-A activates a paracrine signaling pathway (Shh) that facilitates tumor cell metastasis. MAO-A expression is significantly elevated in high-grade renal carcinoma, potentially directly involved in maintaining a dedifferentiated phenotype and promoting tumor invasiveness. In hepatocellular carcinoma (HCC) specimens, abnormal expression of MAO-B is closely associated with vascular invasion, metastasis, and poor prognosis.

[0004] As a non-invasive treatment method, phototherapy has attracted widespread attention due to its low drug resistance and small invasive area. This method can selectively destroy tumor tissue in situ. However, the selection of photosensitizers and their targeting are key factors in determining the effectiveness of phototherapy, and are also the main reasons limiting its further biological applications. At present, the excitation wavelengths of most photosensitizers are concentrated in the visible light region, which leads to insufficient penetration depth and is not conducive to the treatment of deep tumors. Therefore, the synthesis of controllable near-infrared fluorescent molecules and in-depth study of their photophysical and photochemical properties provide important basic data for the construction of activated near-infrared fluorescent molecules. Photosensitizers excited by near-infrared light sources have become a research hotspot for improving the application effect of photosensitizers. They can more effectively induce cell apoptosis, thereby improving the efficiency of phototherapy. Summary of the Invention

[0005] The purpose of the present invention is to provide a monoamine oxidase inhibitor type near-infrared fluorescent probe and its synthesis method and application in phototherapy, so as to provide an important therapeutic tool for inhibiting the activity of MAO in cells and treating tumors that overexpress MAO.

[0006] The implementation process of the present invention is as follows: A monoamine oxidase inhibitor-type near-infrared fluorescent probe, the structural formula of which is shown below: SINH The above compound is abbreviated as SINH.

[0007] The synthesis method of the above compound comprises the following steps: (1)

[0008] Cyclohexanone reacts in a mixed solution of PBr3, N,N-dimethylformamide and chloroform to obtain compound 1; (2)

[0009] Compound 1 reacts with 4-(diethylamino)salicylaldehyde to obtain compound 2; (3)

[0010] 2,3,3-Trimethylindole reacts with 6-bromohexanoic acid to give compound 3; (4)

[0011] Compound 3, 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate, and N,N-diisopropylethylamine were dissolved in dry DMF, and isoniazid was added to react to obtain compound 4; (5)

[0012] Compound 2 and compound 4 react to obtain compound SINH.

[0013] In the above synthesis method, in step (1), the volume ratio of PBr3 to cyclohexanone is 2.5: (0.5~1.5).

[0014] In the above synthesis method, in step (2), the molar ratio of 4-(diethylamino)salicylaldehyde to compound 1 is 1.2:(0.5~1.5).

[0015] In the above synthesis method, in step (3), the molar ratio of 2,3,3-trimethylindole to 6-bromohexanoic acid is 1:(3-5).

[0016] In the above synthesis method, in step (4), the molar ratio of compound 3, 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate, N,N-diisopropylethylamine and isoniazid is 1: (1.0~1.5): (1.5~2.5): (1.0~1.5).

[0017] In the above synthesis method, in step (5), the molar ratio of compound 2 to compound 4 is 1: (0.8~1.2).

[0018] As a control, compound 2 was reacted with compound 3 to obtain compound SCOH, and the molar ratio of compound 2 to compound 3 was 1: (0.8~1.2).

[0019]

[0020] The invention relates to an application of the compound in the preparation of a drug for inducing cell apoptosis.

[0021] The invention relates to an application of the compound in preparing an inhibitor for inhibiting monoamine oxidase activity in living cells.

[0022] Application of the compound of the present invention in the preparation of photothermal therapy drugs for tumors.

[0023] This invention utilizes a near-infrared fluorescent dye probe that can inhibit MAO expression in vitro and in vivo. It exhibits near-infrared absorption and emission, allowing for effective tissue penetration. The probe generates heat upon irradiation with a 660 nm laser, demonstrating superior photothermal performance in mouse tumor photothermal imaging. It also exhibits high toxicity toward cells that overexpress MAO. Photothermal therapy of subcutaneous tumor-bearing mice with this probe significantly inhibited the growth of SH-SY5Y cell xenografts that overexpress MAO.

[0024] Compared with existing technologies, the present invention offers several significant technical advantages: The near-infrared fluorescent probe possesses excellent near-infrared absorption and emission properties, effectively resisting interference from background fluorescence signals, thereby enhancing the probe's anti-interference ability. The near-infrared fluorescent probe exhibits excellent targeting to mitochondria within cells, enabling precise localization and labeling of target organelles. In SH-SY5Y cells, the accumulation of the near-infrared fluorescent probe is mediated by organic anion transporters (OATPs), providing a scientific basis for its intracellular application. The probe exhibits a promising photothermal effect in a tumor-bearing mouse model, effectively converting near-infrared light into thermal energy. Under near-infrared laser irradiation, the near-infrared fluorescent probe generates significant heat, significantly inhibiting the growth of SH-SY5Y cell xenografts that overexpress monoamine oxidase (MAO). In summary, the near-infrared fluorescent probe of the present invention has broad application prospects in the biomedical field, particularly in tumor diagnosis and treatment. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 is the ultraviolet absorption of the near-infrared fluorescent probe SINH, the abscissa is the wavelength (nm), and the ordinate is the absorbance; Figure 2 is the fluorescence spectrum of the near-infrared fluorescent probe SINH, the abscissa is the wavelength (nm), and the ordinate is the fluorescence emission intensity; Figure 3 The toxicity of the near-infrared fluorescent probe SINH to SH-SY5Y cells is measured. The horizontal axis represents the log value of drug concentration, and the vertical axis represents the cell survival rate. Figure 4 This is a confocal fluorescence imaging diagram of the co-localization of the near-infrared fluorescent probe SINH cells; Figure 5 This is a cell absorption diagram of the near-infrared fluorescent probe SINH to SH-SY5Y cells; Figure 6 This is the photothermal imaging image of the near-infrared fluorescent probe SINH on tumor-bearing mice; Figure 7 This figure shows the effect of the near-infrared fluorescent probe SINH on the growth of cell xenograft tumors. DETAILED DESCRIPTION

[0026] The present invention will be further described below in conjunction with specific embodiments. Obviously, the embodiments described are only some embodiments of the present application, rather than all embodiments. Based on the embodiments in this application, all other embodiments obtained by those of ordinary skill in the art without making creative work are within the scope of protection of this application. The methods described are conventional methods unless otherwise specified, and the raw materials described can be obtained from public commercial channels unless otherwise specified.

[0027] The synthetic route of the compound of the present invention is as follows:

[0028] Specifically, the synthesis method of the present invention comprises the following steps: (1) PBr3 was slowly added dropwise to a mixed solution of N,N-dimethylformamide (DMF) and chloroform (CH3Cl) at 0 °C under nitrogen protection. After stirring for 45 min, cyclohexanone was slowly added dropwise to the reaction system and continued to stir at room temperature for 16 h. After the reaction was completed, the reaction solution was poured into ice water and the pH was adjusted to neutral. The solution was extracted with dichloromethane and washed with saturated brine. The organic layer was dried to obtain a yellow oily substance, which was recorded as compound 1.

[0029] (2) 4-(Diethylamino) salicylaldehyde was dissolved in DMF, cesium carbonate was added, and under nitrogen protection, the DMF solution of compound 1 was slowly injected into the reaction system and stirred at room temperature for 12 h. After the reaction was completed, the mixture was diluted with dichloromethane, filtered, and the filtrate was extracted, washed with saturated brine, dried, and the solvent was removed under reduced pressure. The mixture was purified by column chromatography to obtain an orange-red oil, which was recorded as compound 2.

[0030] (3) 2,3,3-Trimethylindole and 6-bromohexanoic acid were dissolved in acetonitrile and reacted under nitrogen protection in an oil bath at 72-90 °C for 54 h. After the reaction, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, and ethyl acetate was added to precipitate a solid. The solid was filtered to obtain a white solid, which was recorded as compound 3.

[0031] (4) Compound 2 and compound 3 were dissolved in anhydrous ethanol and stirred in an oil bath at 65-85 °C for 12 h. After the reaction was completed, the mixture was cooled, the solvent was removed under reduced pressure, and the mixture was purified by column chromatography to obtain a green solid, which was recorded as compound SCOH.

[0032] (5) Compound 3, 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate and N,N-diisopropylethylamine were dissolved in dry DMF and stirred at room temperature under nitrogen for 1 h. Isoniazid was then added and stirred for 3 h. After the reaction was completed, the mixture was washed with distilled water. The aqueous layer was collected and dried to obtain a slightly yellow oily substance, which was recorded as compound 4.

[0033] (6) Compound 2 and compound 4 were dissolved in anhydrous ethanol and stirred in an oil bath at 65-85 °C for 12 h. After the reaction was completed, the mixture was cooled, the solvent was removed under reduced pressure, and the mixture was purified by column chromatography to obtain a dark green solid, which was recorded as compound SINH.

[0034] Example 1 Synthesis of monoamine oxidase inhibitor-type near-infrared fluorescent probe SINH.

[0035] (1) Synthesis of compound 1: 12.4 mL of PBr3 was slowly added dropwise to a mixed solution of 11.2 mL of N,N-dimethylformamide (DMF) and 50 mL of chloroform (CH3Cl) at 0 °C under nitrogen protection. After stirring for 45 min, 5 mL of cyclohexanone was slowly added dropwise to the reaction system and continued to stir at room temperature for 16 h. After the reaction was completed, the reaction solution was poured into ice water and the pH was adjusted to neutral. The solution was extracted with 100 mL of dichloromethane and washed three times with saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to obtain compound 1 as a yellow oil.

[0036] (2) Synthesis of compound 2: 4-(Diethylamino) salicylaldehyde (2.45 g, 12.7 mmol) was dissolved in 7 mL of dry DMF in a 50 mL two-necked round-bottom flask, and cesium carbonate (3.47 g, 10.7 mmol) was added. Under nitrogen protection, the DMF solution of compound 1 was slowly injected into the reaction system and stirred at room temperature for 12 h. After the reaction was completed, it was diluted with 50 mL of dichloromethane, filtered, and the filtrate was extracted and washed three times with saturated brine. The product was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and purified by column chromatography (PE: EtOAc = 20:1) to obtain compound 2 as an orange-red oil.

[0037] (3) Synthesis of compound 3: 2,3,3-Trimethylindole (502.5 μL, 3.14 mmol) and 6-bromohexanoic acid (2.45 g, 12.56 mmol) were dissolved in 15 mL of acetonitrile and placed in a 50 mL round-bottom flask. The mixture was reacted under nitrogen protection in an oil bath at 72-90 °C for 54 h. After the reaction was completed, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, ethyl acetate was added, and the solid was precipitated. Compound 3 was obtained by filtration as a pink-white solid.

[0038] (4) Synthesis of compound SCOH: In a 25 mL round-bottom flask, compound 2 (85.3 mg, 0.3 mmol) and compound 3 (112.1 mg, 0.3 mmol) were dissolved in 6 mL of anhydrous ethanol and stirred in an oil bath at 65-85 °C for 12 h. After the reaction, the mixture was cooled, the solvent was removed under reduced pressure, and the product was purified by column chromatography (CH2Cl2:MeOH = 20:1) to obtain compound SCOH as a green solid.

[0039] (5) Synthesis of compound 4: In a 50 mL round-bottom flask, compound 3 (200 mg, 0.538 mmol), 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate (245.1 mg, 0.645 mmol) and N,N-diisopropylethylamine (188 μL, 1.079 mmol) were dissolved in 8 mL of dry DMF. After stirring at room temperature under nitrogen protection for 1 h, isoniazid (88.5 mg, 0.646 mmol) was added and stirring was continued for 3 h. After the reaction was completed, the mixture was washed with distilled water, and the aqueous layer was collected and dried to obtain compound 4 as a slightly yellow oil.

[0040] (6) Synthesis of SINH: In a 25 mL round-bottom flask, compound 2 (70.5 mg, 0.25 mmol) and compound 4 (97.9 mg, 0.25 mmol) were dissolved in 5 mL of anhydrous ethanol and stirred in an oil bath at 65-85 °C for 12 h. After the reaction, the mixture was cooled, the solvent was removed under reduced pressure, and purified by column chromatography (CH2Cl2:MeOH = 20:1) to obtain SINH as a dark green solid (96 mg, yield 58.4%). 1 H NMR (400 MHz, MeOD) δ 8.69 – 8.64 (m, 2H), 8.62 (d, J = 14.2 Hz,1H), 7.84 – 7.78 (m, 2H), 7.55 (d, J = 7.5 Hz, 1H), 7.52 (s, 1H), 7.47 – 7.41(m, 2H), 7.37 (d, J = 7.9 Hz, 1H), 7.30 (td, J = 7.4, 1.0 Hz, 1H), 6.92 (dd, J = 9.0, 2.4 Hz, 1H), 6.67 (d, J = 2.4 Hz, 1H), 6.26 (d, J = 14.2 Hz, 1H),4.21 (t, J = 7.4 Hz, 2H), 3.59 (q, J = 7.1 Hz, 4H), 2.72 (dt, J = 11.8, 6.1Hz, 4H), 2.36 (t, J = 7.1 Hz, 2H), 1.90 (dp, J= 12.0, 6.8 Hz, 4H), 1.80 (s,8H), 1.60 (tt, J = 9.2, 5.9 Hz, 2H), 1.28 (t, J = 7.1 Hz, 6H). 13 C NMR (150MHz, MeOD) δ 173.92, 173.03, 164.88, 163.36, 156.33, 152.32, 149.56(2C),142.34, 142.13, 141.20, 141.00, 138.10, 129.44, 128.52, 125.19, 123.15,122.13, 121.69(2C), 114.69, 113.05, 112.07, 111.01, 99.70, 95.37, 49.39,44.62(2C), 43.70, 33.04, 28.26, 27.29(2C), 26.60, 25.85, 24.67, 23.93, 20.54,11.35(2C).HRMS (ESI) m / z calcd for C 41 H 48 N5O3 + (M+H) + : 658.3752, Found:658.3749.

[0041] Example 2 Spectral properties of probe SINH A certain volume of probe SINH stock solution (10 mM) or compound SCOH stock solution (10 mM) was added to a 1.5 mL centrifuge tube and then diluted with appropriate amounts of DMSO and PBS buffer solution. After dilution, the concentration of the probe solution was 10 μM, the final volume was 1 mL, and the test system was a PBS buffer solution containing 10% DMSO. The excitation wavelength of the fluorimeter was set to 690 nm, and the emission wavelength reception range was 720 nm to 900 nm. The experimental results are shown in Figure 2. Figure 1 and Figure 2 As shown, it shows that the SINH probe has obvious near-infrared absorption and emission characteristics.

[0042] Example 3: Determination of the cytotoxicity of probe SINH to SH-SY5Y cells.

[0043] SH-SY5Y cells were seeded in a 96-well plate. After the cells attached and grew to an appropriate density, different concentrations of the probe SINH were added to each well and incubated in an incubator for 24 hours. Subsequently, 10 μL of MTT solution (at a concentration of 5 mg / mL) was added to each well and cultured for another 4 hours. Afterwards, the culture medium was carefully removed using a pipette, and 100 μL of DMSO was added to each well, and the mixture was shaken thoroughly to dissolve the formed purple crystals. Finally, the optical density (OD) of each well was measured at a wavelength of 570 nm using a multifunctional microplate reader (Infinite M1000), and calibrated at 630 nm to calculate the survival rate of each cell line. The results of the cytotoxicity assay of the probe SINH on SH-SY5Y cells are shown in Figure 2. Figure 3 As shown, the results show that the probe SINH exhibits significant concentration-dependent cytotoxicity. At a concentration of 10 μM, the probe is able to kill almost all tumor cells. In addition, the probe SINH preferentially accumulates in SH-SY5Y cells, leading to faster tumor cell death.

[0044] Example 4 Targeting ability of probe SINH to cell organelles SH-SY5Y cells were seeded in confocal culture dishes and cultured in an incubator for 12 hours. Subsequently, the probe SINH (at a concentration of 2 μM) was added to the cells and incubated together for 1 hour. Next, two commercial organelle fluorescent dyes, the nuclear dye Hoechst 33342 and the mitochondrial dye Mito-Tracker Green, were added respectively. After treatment for 30 minutes, the cells were washed three times with sterile PBS to remove the unabsorbed probes. Finally, the cells were imaged using a TCS SP8 DIVE confocal microscope. Figure 4 As shown, the red fluorescence of the SINH probe overlaps strongly with the green fluorescence of the mitochondrial dye, with a Pearson's correlation coefficient of P = 0.90. This indicates that the SINH probe is effectively targeted to mitochondria.

[0045] Example 5 Cellular uptake pathway of probe SINH SH-SY5Y cells were seeded in confocal dishes and cultured in an incubator for 12 hours. Subsequently, the cells were incubated with the probe SINH (at a concentration of 2 μM) at 37°C or 4°C for 30 minutes. Next, commercial dyes Mito-TrackerGreen and Hoechst 33342 were used for co-staining, and after 30 minutes of treatment, the cells were washed three times with sterile PBS to remove unabsorbed probes. Finally, the cells were imaged using a TCS SP8 DIVE confocal microscope. In addition, SH-SY5Y cells were seeded in confocal dishes and cultured in an incubator for 12 hours. The cells were then pretreated with an excess of AZD5363 (OATP competitive inhibitor) for 1 hour, and then the experiment was performed according to the normal incubation process at 37°C as described above. As Figure 5 As shown in Figure 3, the fluorescence intensity of the AZD5363 group was similar to that of the 4°C group, and both were lower than that of the normal group. This indicates that the cellular uptake of the probe SINH is mediated by OATP.

[0046] Example 6 Photothermal imaging of tumor-bearing mice using the SINH probe Tumor-bearing mice were randomly divided into two groups: one group was injected with the probe SINH in situ, and the other group was injected with PBS buffer in situ. One hour after injection, the tumor site was irradiated with a 660 nm laser for 5 minutes at a laser power of 1 W / cm², and temperature changes were recorded using a photothermal imager. Figure 6 As shown, the temperature of the probe can be raised to 50°C within 5 minutes, effectively killing tumor cells.

[0047] Example 7 Inhibitory Effect of Probe SINH on Xenograft Tumors Tumor-bearing mice were randomly divided into five groups: probe SINH+Laser group, probe SINH group, SCOH group, INH group, and saline group. The treatment of each group was as follows: Probe SINH+Laser group: 100 μL of SINH (50 μM concentration) was injected into the tumor, and one hour later, the tumor site was irradiated with a 660 nm laser for 5 minutes at a laser power density of 1 W / cm².

[0048] Probe SINH group, SCOH administration group, INH administration group and normal saline group: 100 μL of SINH (50 μM), SCOH (50 μM), INH (50 μM) and normal saline were injected into the tumor, respectively.

[0049] During the 14-day treatment period, the body weight and tumor volume (V = W²L / 2) of mice in each group were monitored daily. Figure 7As shown, the SINH probe exhibited a good phototherapy effect, and the tumor volume in the SINH+Laser group was significantly reduced. This indicates that SINH can inhibit the activity of monoamine oxidase (MAO) and generate heat under light conditions, thereby achieving a tumor inhibitory effect.

Claims

1. A monoamine oxidase inhibitor-type near-infrared fluorescent probe, characterized in that The structural formula is shown below. 。 2. The method for synthesizing the compound according to claim 1, characterized in that The following steps are involved: (1) Cyclohexanone reacts in a mixed solution of PBr3, N,N-dimethylformamide and chloroform to obtain compound 1; (2) , compound 1 reacts with 4-(diethylamino) salicylaldehyde to obtain compound 2; （3） , 2,3,3-trimethylindole reacts with 6-bromohexanoic acid to obtain compound 3; （4） Compound 3, 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate and N,N-diisopropylethylamine were dissolved in dry DMF, and isoniazid was added to react to obtain compound 4; , compound 2 and compound 4 react to obtain compound SINH.

3. The synthesis method according to claim 2, wherein: In step (1), the volume ratio of PBr3 to cyclohexanone is 2.5:(0.5~1.5).

4. The synthesis method according to claim 2, wherein: In step (2), the molar ratio of 4-(diethylamino)salicylaldehyde to compound 1 is 1.2:(0.5-1.5).

5. The synthesis method according to claim 2, wherein: In step (3), the molar ratio of 2,3,3-trimethylindole to 6-bromohexanoic acid is 1: (3-5).

6. The synthesis method according to claim 2, characterized in that: In step (4), the molar ratio of compound 3, 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate, N,N-diisopropylethylamine and isoniazid is 1:(1.0-1.5):(1.5-2.5):(1.0-1.5).

7. The synthesis method according to claim 2, wherein: In step (5), the molar ratio of compound 2 to compound 4 is 1: (0.8~1.2).

8. Use of the compound according to claim 1 in the preparation of a drug for inducing cell apoptosis.

9. Use of the compound according to claim 1 in the preparation of inhibitors for inhibiting monoamine oxidase activity in living cells.

10. Use of the compound according to claim 1 in the preparation of drugs for photothermal therapy of tumors.

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