A hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP and a preparation method thereof

Abstract

The application belongs to the technical field of organic synthesis, and particularly discloses a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP and a preparation method thereof. ‑ As a protecting group of N-H bond, Knoevenagel condensation reaction is carried out between a BODIPY compound and a t-butyl carbamate derivative, and finally, the 3N-IBDP compound is obtained. The equilateral triangle structure can effectively improve the stability of the molecule, and is beneficial to maintaining the molecular configuration, and the atoms can form interaction, so that the molecule has the properties of aggregation-induced emission and red light emission. By introducing the t-butyl carbamate derivative as an electron donor, the intramolecular ICT is increased, the energy level difference (Delta Est) between the singlet state and the triplet state is minimized, and heavy atom iodine is introduced at the 2, 6 positions to generate more active oxygen which can kill bacteria. The oleophobic group ammonium cation makes it have good water dispersibility, excellent stability and excellent biocompatibility.

Description

Technical Field

[0001] The invention belongs to the technical field of organic synthesis and relates to the synthesis of fluorescent probes, in particular to a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP and a preparation method thereof. Background Art

[0002] Alzheimer's disease (AD) is one of the most common neurodegenerative diseases, affecting more than 50 million people worldwide. According to the World Alzheimer's Report, due to the aging population, the number of people with dementia is expected to increase to 150 million by 2050. In addition, due to the high incidence of AD, the lack of effective drugs and poor prognosis, AD imposes a huge economic and mental burden on families and society. The intestinal flora can regulate host brain function and behavior, including cognitive behavior, through the microbiome-gut-brain axis. Increased permeability of the blood-brain barrier caused by intestinal barrier and intestinal flora imbalance will increase the incidence of neurodegenerative diseases. Gut microbial metabolites and their effects on host neurochemical changes may increase the risk of AD. Infection with pathogenic microorganisms will also increase the risk of AD.

[0003] Photodynamic antimicrobial therapy (PDT) is a promising alternative to traditional drug chemotherapy and a potential non-invasive treatment. It involves three key elements: a photosensitizer, a light source, and oxygen. Oxidative damage to bacterial cell membranes can lead to bacterial toxicity. Antimicrobial agents based on PDT, such as chlorin e6 and porphyrin derivatives, exhibit excellent antimicrobial activity. However, the difficulty in modifying and purifying porphyrins and their derivatives has limited their further development. Boron dipyrrole (BODPY), another PS commonly used in PDT, holds broad application prospects due to its low toxicity, easily modifiable structure, and high molar extinction coefficient. BODIPY is an important class of organic functional dyes composed of two pyrrole rings connected by a methine bridge. It exhibits efficient reactive oxygen species (ROS) generation and high cellular uptake upon light irradiation, making it a promising candidate for rapid photodynamic antimicrobial therapy for bacterial diseases. This provides a novel strategy for photodynamic sterilization and infection elimination, thereby preventing or mitigating AD. Therefore, the development of photosensitizer probes with excellent hydrophilicity, stable structure, and efficient ROS generation is of great significance. Summary of the Invention

[0004] In view of the shortcomings of the existing technology, the purpose of the present invention is to provide a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP, which has the characteristics of long infrared wavelength, high hydrophilicity and high stability; another purpose of the present invention is to provide a method for preparing the fluorescent probe.

[0005] The present invention is achieved through the following technical solutions:

[0006] A hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP, whose molecular structure is shown below:

[0007]

[0008] A further improvement of the present invention is:

[0009] A method for preparing a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP comprises the following steps:

[0010] (1) reacting 2,4-dimethylpyrrole with p-formylbenzoic acid to synthesize the compound BODIPY;

[0011] (2) subjecting the compound BODIPY to iodination reaction to prepare 2IBDPIPY;

[0012] (3) reacting 2,2′-(ethylenedioxy)bis(ethylamine) with di-tert-butyl carbonate to synthesize compound TB;

[0013] (4) reacting compound 2IBDP with compound TB to synthesize the intermediate 3Boc-IBDP;

[0014] (5) reacting the intermediate 3Boc-IBDP with trifluoroacetic acid to prepare the product 3N-IBDP;

[0015] The reaction equation is as follows:

[0016]

[0017]

[0018] A further improvement of the present invention is

[0019] The specific process of step (1) is as follows: 2,4-dimethylpyrrole and p-formylbenzoic acid are mixed and dissolved in dichloromethane, trifluoroacetic acid is added dropwise, and the mixture is stirred overnight at room temperature in a nitrogen atmosphere in the dark, 2,3-dimethyl-5,6-dicyanobenzoquinone, triethylamine, and boron trifluoride ether are added in sequence, and stirring is continued for 8-10 hours. After the reaction is complete, a green fluorescent fluoroboron dipyrrole fluorescent dye is separated, and the fluoroboron dipyrrole fluorescent dye, p-formylbenzoic acid, and toluenesulfonamide are dissolved in a mixed solution of toluene and piperidine, placed in a round-bottom flask equipped with a Dean-Stark apparatus, heated to reflux at 140°C-150°C until all the solvent is collected by the Dean-Stark apparatus, and then toluene and piperidine are added to the reaction medium, and the reaction is repeated at least once. After TLC tracking until the reaction of the raw materials is complete, column chromatography is performed, and the solvent is removed by reduced pressure distillation to obtain a black solid product BODIPY.

[0020] Furthermore, the molar ratio of the 2,4-dimethylpyrrole, p-formylbenzoic acid and 2,3-dimethyl-5,6-dicyanobenzoquinone is 1:1.8-2.5:0.8-1.2.

[0021] Furthermore, the specific process of step (2) is as follows: iodic acid is dissolved in water, and then added dropwise to anhydrous ethanol containing BODIPY and iodine to react. After the reaction is completed, separation and purification are performed to obtain a yellow solid 2IBDPIPY.

[0022] Furthermore, the molar ratio of iodic acid, BODIPY and iodine is 1.8-2:1:2-2.5.

[0023] Furthermore, the specific process of step (3) is as follows: dissolving 2,2′-(ethylenedioxy)bis(ethylamine) in DCM, adding di-tert-butyl carbonate dissolved in DCM dropwise, stirring at room temperature overnight, and separating to obtain compound TB after the reaction is completed.

[0024] Furthermore, the molar ratio of the 2,2′-(ethylenedioxy)bis(ethylamine) to di-tert-butyl carbonate is 1:0.1-0.2.

[0025] Furthermore, the specific process of step (4) is as follows: 2IBODIPY, HOBt and DIPEA are dissolved in anhydrous DMF, and the solution is cooled in an ice-salt bath, EDC is added, and the solution is stirred while cooling in an ice-salt bath, and TB dissolved in DMF is added dropwise. After the addition is complete, the temperature is raised to room temperature and stirred in the dark for 20-26 hours. The reaction is terminated, and the intermediate 3Boc-IBDP is separated and purified; the molar ratio of 2IBODIPY, HOBt, DIPEA, EDC and TB is 1:5-7:6-8:4-6:3-6.

[0026] Furthermore, the specific process of step (5) is as follows: adding trifluoroacetic acid to a solution of 3Boc-IBDP in DCM at -5°C to 5°C, stirring at room temperature for 4-6 hours, and quenching after the reaction is completed, and separating to obtain the product 3N-IBDP.

[0027] Compared with the prior art, the present invention has the following beneficial effects:

[0028] The equilateral triangle structure formed by the spatial arrangement of the fluorescent probe of the present invention can effectively improve the stability of the molecule and is conducive to maintaining the molecular configuration. -A fluoroborylpyrrole BODIPY compound, acting as a protecting group for the NH bond, undergoes a Knoevenagel condensation reaction with a tert-butyl carbamate derivative to yield a 3N-IBDP compound. The equilateral triangle structure effectively enhances molecular stability and helps maintain the molecular configuration. The interactions between atoms allow for aggregation-induced emission and red emission. By introducing a tert-butyl carbamate derivative as an electron donor, the intramolecular ICT is increased, minimizing the energy difference (ΔEst) between the singlet and triplet states. Furthermore, heavy iodine atoms at the 2 and 6 positions generate more reactive oxygen species that can kill bacteria. The oleophobic group, the ammonia cation, imparts excellent water dispersibility, stability, and biocompatibility. The development of BODIPY-based fluorescent molecular probes for photodynamic sterilization is of great significance for the treatment of AD caused by bacterial infection. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 This is the H NMR spectrum of the 3N-IBDP compound obtained in Example 1 of the present invention;

[0030] Figure 2 The antibacterial performance of 3N-IBDP obtained in Example 1 of the present invention against Staphylococcus aureus in vitro under different illumination conditions. (a: blank control, no illumination, no BODIPY; b: with BODIPY, no illumination; c: with BODIPY, natural illumination; d: with BODIPY, 24W fluorescence (λ = 395 nm).) DETAILED DESCRIPTION

[0031] The present invention will be described in detail below with reference to specific embodiments.

[0032] The preparation method of 2IBODIPY used in the embodiments of the present invention is as follows:

[0033]

[0034] Weigh 150 mg (2.0 mmol) of p-formylbenzoic acid and dissolve it in 200 mL of freshly distilled dichloromethane. Inject 412 mg (4.4 mmol) of 2,4-dimethylpyrrole via syringe and rapidly add 2 drops of trifluoroacetic acid dropwise. Stir rapidly with magnetic stirring, in the dark, at room temperature overnight under a nitrogen atmosphere. Then, add 454 mg (2 mmol) of 2,3-dimethyl-5,6-dicyanobenzoquinone while stirring. Continue stirring and add 3 mL of freshly distilled triethylamine, stirring for 10 minutes. Slowly add 3 mL of boron trifluoride etherate dropwise in an ice bath. After 10 hours, monitor the reaction until the starting material is completely reacted. Column chromatography and vacuum distillation to remove the solvent yield a green fluorescent boron trifluoride pyrrole dye.

[0035] Fluoroboron dipyrrole fluorescent dye (0.54 mmol), p-formylbenzoic acid (1.08 mmol), and p-toluenesulfonamide (0.01 mmol) were dissolved in a mixed solution of toluene (25 mL) and piperidine (1 mL), placed in a round-bottom flask equipped with a Dean-Stark apparatus, and heated under reflux at 142°C until all the solvent was collected by the Dean-Stark apparatus. Toluene (25 mL) and piperidine (1 mL) were then added to the reaction medium, and heating under reflux at 142°C was continued until all the solvent was collected by the Dean-Stark apparatus. The addition of toluene (25 mL) and piperidine (1 mL) and the heating under reflux process were repeated four times. This process was tracked by TLC. After the raw materials reacted completely, column chromatography was performed and the solvent was removed by distillation under reduced pressure to obtain a black solid product, namely BODIPY (BDP).

[0036] Then, iodic acid is dissolved in water and then added dropwise to anhydrous ethanol containing fluorescent dye and iodine for reaction. After the reaction is completed, the mixture is cooled to room temperature, the solvent is removed under reduced pressure, and column chromatography is performed to separate and purify the mixture to obtain a yellow solid, namely the target product 2IBODIPY.

[0037] Example 1

[0038] 2,2'-(ethylenedioxy)bis(ethylamine) (10.7 g, 72.0 mmol) was dissolved in DCM (72 mL) and di-tert-butyl carbonate (2.6 g, 12 mmol) in DCM (28 mL) was added dropwise over 2 h. The reaction solution was stirred at room temperature overnight and the solvent was evaporated. The residue was dissolved in water and extracted with DCM. The filtrate was washed three times with anhydrous ethanol and dried over MgSO4. The solvent was removed to obtain the product TB (2.5 g, 99%) as a colorless oil. 1 H NMR (300MHz, CDCl3): δ=1.44 (s, 9H), 2.91 (t, 2H), 3.35-3.42 (m, 2H), 3.48-3.56 (m, 4H), 3.67 (s, 4H), 5.20 (br, 1H).

[0039] 2IBODIPY (316 mg, 0.36 mmol), HOBt (336 mg, 2.2 mmol) and DIPEA (385 μL, 2.4 mmol) were dissolved in anhydrous DMF (25 mL) and the solution was cooled to -15 ° C in an ice-salt bath. EDC (350 mg, 1.8 mmol) was then added and the mixture was stirred at -15 ° C for 30 min. TB (376 mg, 1.5 mmol) in DMF (5 mL) was added dropwise, the solution was allowed to warm to room temperature and stirred in the dark for 24 h. The organic layer was washed with water and brine, dried, and concentrated to give a dark solid. Purification by DCM / MeOH (19:1, v / v) column chromatography gave the product 3Boc-IBDP as a dark solid (360 mg, 85%).

[0040] Trifluoroacetic acid (10 mL) was added to a solution of 3Boc-IBDP (360 mg) in DCM (15 mL) at 0°C. The solution was allowed to warm to room temperature and stirred for 5 h. The reaction was quenched with excess methanol. The solvent was evaporated in vacuo to quantitatively obtain the product 3N-IBDP. The compound was analyzed by NMR. 1 H NMR spectrum Figure 1 As shown, 1 H NMR (300MHz, DMSO-D6): δ = 9.91 (s, 3H), 7.95 (d, J = 4.4Hz, 6H), 7.52 (d, J = 4.4Hz, 6H), 7.2 (s, 9H), 6.95 ~ 6.99 (m, 2H), 6.73 ~ 6.7 9 (m, 4H), 6.28 (d, J = 4.4Hz, 3H), 5.89 (d, J = 4.4Hz, 9H), 5.67 (d, J = 4.4Hz, 1H), 4.7 (d, J = 4.4Hz, 3H), 2.29 (s, 3H), 1.95 (s, 3H).

[0041] Example 2

[0042] 2,2'-(ethylenedioxy)bis(ethylamine) (12.9 g, 86 mmol) was dissolved in DCM (80 mL) and di-tert-butyl carbonate (3.1 g, 14 mmol) in DCM (24 mL) was added dropwise over 2 h. The reaction solution was stirred at room temperature overnight and the solvent was evaporated. The residue was dissolved in water and extracted with DCM. The filtrate was washed three times with anhydrous ethanol and dried over MgSO4. The solvent was removed to obtain the product TB (2.5 g, 99%) as a colorless oil. 1 H NMR (300MHz, CDCl3): δ=1.44 (s, 9H), 2.91 (t, 2H), 3.35-3.42 (m, 2H), 3.48-3.56 (m, 4H), 3.67 (s, 4H), 5.20 (br, 1H).

[0043] 2IBODIPY (264 mg, 0.3 mmol), HOBt (280 mg, 1.8 mmol) and DIPEA (321 μL, 2 mmol) were dissolved in anhydrous DMF (20 mL) and the solution was cooled to -15°C in an ice-salt bath. EDC (291 mg, 1.52 mmol) was then added and the mixture was stirred at -15°C for 0.5 h. TB (314 mg, 1.26 mmol) in DMF (5 mL) was added dropwise, the solution was allowed to warm to room temperature and stirred in the dark for 24 h. The organic layer was washed with water and brine, dried, and concentrated to give a dark solid. Purification by DCM / MeOH (20:1, v / v) column chromatography gave the product 3Boc-IBDP as a dark solid (360 mg, 85%).

[0044] Trifluoroacetic acid (10 mL) was added to a solution of 3Boc-IBDP (300 mg) in DCM (15 mL) at 0°C. The solution was allowed to warm to room temperature and stirred for 5 h. The reaction was quenched with excess methanol. The solvent was evaporated in vacuo to give the product 3N-IBDP quantitatively. The compound was identified by NMR. 1 The H NMR spectrum was used for characterization. 1 H NMR (300MHz, DMSO-D6): δ = 9.91 (s, 3H), 7.95 (d, J = 4.4Hz, 6H), 7.52 (d, J = 4.4Hz, 6H), 7.2 (s, 9H), 6.95 ~ 6.99 (m, 2H), 6.73 ~ 6.7 9 (m, 4H), 6.28 (d, J = 4.4Hz, 3H), 5.89 (d, J = 4.4Hz, 9H), 5.67 (d, J = 4.4Hz, 1H), 4.7 (d, J = 4.4Hz, 3H), 2.29 (s, 3H), 1.95 (s, 3H).

[0045] Example 3

[0046] 2,2'-(ethylenedioxy)bis(ethylamine) (43 mmol) was dissolved in DCM (80 mL) and di-tert-butyl carbonate (3.1 g, 14 mmol) in DCM (24 mL) was added dropwise over 2 h. The reaction solution was stirred at room temperature overnight and the solvent was evaporated. The residue was dissolved in water and extracted with DCM. The filtrate was washed three times with anhydrous ethanol and dried over MgSO4. The solvent was removed to obtain the product TB (2.5 g, 99%) as a colorless oil. 1HNMR (300MHz, CDCl3): δ=1.44 (s, 9H), 2.91 (t, 2H), 3.35-3.42 (m, 2H), 3.48-3.56 (m, 4H), 3.67 (s, 4H), 5.20 (br, 1H).

[0047] 2IBODIPY (264 mg, 0.3 mmol), HOBt (280 mg, 1.8 mmol) and DIPEA (321 μL, 2 mmol) were dissolved in anhydrous DMF (20 mL) and the solution was cooled to -15°C in an ice-salt bath. EDC (291 mg, 1.52 mmol) was then added and the mixture was stirred at -15°C for 2 h. TB (314 mg, 1.26 mmol) in DMF (5 mL) was added dropwise, the solution was allowed to warm to room temperature and stirred in the dark for 24 h. The organic layer was washed with water and brine, dried, and concentrated to give a dark solid. Purification by DCM / MeOH (20:1, v / v) column chromatography gave the product 3Boc-IBDP as a dark solid (360 mg, 85%).

[0048] Trifluoroacetic acid (10 mL) was added to a solution of 3Boc-IBDP (300 mg) in DCM (15 mL) at 0°C. The solution was allowed to warm to room temperature and stirred for 6 h. The reaction was quenched with excess methanol. The solvent was evaporated in vacuo to give the product 3N-IBDP quantitatively. The compound was identified by NMR. 1 The H NMR spectrum was used for characterization. 1 H NMR (300MHz, DMSO-D6): δ = 9.91 (s, 3H), 7.95 (d, J = 4.4Hz, 6H), 7.52 (d, J = 4.4Hz, 6H), 7.2 (s, 9H), 6.95 ~ 6.99 (m, 2H), 6.73 ~ 6.7 9 (m, 4H), 6.28 (d, J = 4.4Hz, 3H), 5.89 (d, J = 4.4Hz, 9H), 5.67 (d, J = 4.4Hz, 1H), 4.7 (d, J = 4.4Hz, 3H), 2.29 (s, 3H), 1.95 (s, 3H).

[0049] Example 4

[0050] In vitro anti-Staphylococcus aureus activity test of 3N-IBDP under different light conditions

[0051] Staphylococcus aureus (S. aureus) was cultured in LB broth for 24 h. The incubated bacterial solution was centrifuged at 6000 rpm for 10 minutes and the supernatant was removed. The bacterial precipitate was washed three times with PBS and redispersed in 4 mL of PBS solution. The bacteria (10 8 One group was set as blank bacterial control group a, and the other three experimental groups (b: no light, c: natural light, d: 24W fluorescent lamp with filter (λ=395nm)) were used for 10 8 The bacterial suspension with CFU / mL was incubated with 3N-IBDP sample at a concentration of 1 mg / mL. The culture was shaken at 150 rpm for 24 h. The three experimental groups were irradiated for 2 h in the dark, natural light, and a 24W fluorescent lamp with a filter (λ = 395 nm) at a distance of 5 cm from the light source. Then, the UV absorbance of the bacteria at 600 nm was measured. 600 The bacterial growth curve is drawn with absorbance as the horizontal and vertical coordinates. The specific results are as follows Figure 2 The results showed that the antibacterial effect of 3N-IBDP was the best under the irradiation of 24W fluorescent lamp (λ=395nm).

[0052] The above embodiments are intended only to illustrate the technical concepts and features of the present invention. Their purpose is to enable those skilled in the art to understand the contents of the present invention and implement them accordingly. They are not intended to limit the scope of protection of the present invention. Any equivalent changes or modifications made in accordance with the spirit of the present invention are intended to be covered by the scope of protection of the present invention.

Claims

1. A hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP, characterized in that: The molecular structure is shown below:

2. The method for preparing a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP according to claim 1, characterized in that: The following steps are involved: (1) reacting 2,4-dimethylpyrrole with p-formylbenzoic acid to synthesize the compound BODIPY; (2) subjecting the compound BODIPY to iodination reaction to prepare 2IBDPIPY; (3) reacting 2,2′-(ethylenedioxy)bis(ethylamine) with di-tert-butyl carbonate to synthesize compound TB; (4) reacting compound 2IBDP with compound TB to synthesize the intermediate 3Boc-IBDP; (5) reacting the intermediate 3Boc-IBDP with trifluoroacetic acid to prepare the product 3N-IBDP; The reaction equation is as follows:

3. The method for preparing a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP according to claim 2, characterized in that: The specific process of step (1) is as follows: 2,4-dimethylpyrrole and p-formylbenzoic acid are mixed and dissolved in dichloromethane, trifluoroacetic acid is added dropwise, and the mixture is stirred overnight in the dark at room temperature under a nitrogen atmosphere. 2,3-dimethyl-5,6-dicyanobenzoquinone, triethylamine, and boron trifluoride ether are added in sequence, and stirring is continued for 8-10 hours. After the reaction is complete, compound 3 is separated, compound 3, p-formylbenzoic acid, and toluenesulfonamide are dissolved in a mixed solution of toluene and piperidine, placed in a round-bottom flask equipped with a Dean-Stark apparatus, heated to reflux at 140°C-150°C until all the solvent is collected by the Dean-Stark apparatus, and then toluene and piperidine are added to the reaction medium. The process is repeated at least once, and TLC is followed until the reaction of the raw materials is complete. Column chromatography and reduced pressure distillation are performed to remove the solvent to obtain a black solid product BODIPY.

4. The method for preparing a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP according to claim 2, characterized in that: The specific process of step (2) is as follows: iodic acid is dissolved in water, and then added dropwise to anhydrous ethanol containing BODIPY and iodine to react. After the reaction is completed, separation and purification are performed to obtain a yellow solid 2IBDPIPY.

5. The method for preparing a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP according to claim 4, characterized in that: The molar ratio of iodic acid, BODIPY and iodine is 1.8-2:1:2-2.

5.

6. The method for preparing a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP according to claim 2, characterized in that: The specific process of step (3) is as follows: dissolving 2,2′-(ethylenedioxy)bis(ethylamine) in DCM, adding di-tert-butyl carbonate dissolved in DCM dropwise, stirring at room temperature overnight, and separating to obtain compound TB after the reaction is completed.

7. The method for preparing a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP according to claim 6, characterized in that: The molar ratio of the 2,2'-(ethylenedioxy)bis(ethylamine) to di-tert-butyl carbonate is 1:0.1-0.

2.

8. The method for preparing a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP according to claim 2, characterized in that: The specific process of step (4) is as follows: 2IBODIPY, HOBt and DIPEA are dissolved in anhydrous DMF, and the solution is cooled in an ice-salt bath, EDC is added, and the solution is stirred while cooling in an ice-salt bath, and TB dissolved in DMF is added dropwise. After the addition is complete, the temperature is raised to room temperature and stirred in the dark for 20-26 hours. The reaction is terminated, and the intermediate 3Boc-IBDP is separated and purified; the molar ratio of 2IBODIPY, HOBt, DIPEA, EDC and TB is 1:5-7:6-8:4-6:3-6.

9. The method for preparing a hydrophilic equilateral triangle BODIPY photodynamic sterilization fluorescent probe 3N-IBDP according to claim 2, characterized in that: The specific process of step (5) is as follows: trifluoroacetic acid is added to a solution of 3Boc-IBDP in DCM at -5°C to 5°C, stirred at room temperature for 4-6 hours, and after the reaction is completed, the product 3N-IBDP is obtained by quenching and isolating.

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