A brominated BODIPY-containing photosensitizer, preparation method and application
By optimizing the synthesis method of BODIPY photosensitizer containing bromine and ring, the singlet oxygen generation ability and photostability are improved, the shortcomings of existing photosensitizers in photodynamic therapy are solved, and efficient photodynamic therapy application is achieved.
Patent Information
- Application Number
- CN202410515044.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2024-04-26
- Publication Date
- 2025-09-05
- Estimated Expiration
- 2044-04-26
AI Technical Summary
The existing photosensitizers have low singlet oxygen production capacity and poor photo stability in photodynamic therapy, which limits their application in treatment.
Using the preparation method of the bromine-containing BODIPY photosensitizer, the synthesis path is optimized to improve the singlet oxygen generation capacity and photostability by adjusting the molar feed ratio and reaction conditions of compound 1 with NBS, 4-cyanobenzene boric acid, catalyst and K2CO3.
The prepared compound I has high singlet oxygen generation ability and good light stability. It is suitable for photodynamic treatment. It has a simple synthesis method, low cost and simple product purification.
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Figure CN118373840B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a photosensitizer, and more specifically to a preparation method and application of a brominated BODIPY-containing photosensitizer. Background Art
[0002] Photodynamic therapy (PDT) is a new technology based on light and photosensitizers to treat diseases. It has been widely used in the treatment of tumors. The mechanism of action is that the photosensitizer absorbs light of a specific wavelength, which makes the photosensitizer excited. The excited photosensitizer transfers energy to the surrounding oxygen molecules, generating singlet oxygen ( 1 O2). The core issue of photodynamic therapy is the singlet oxygen ( 1 O2), using 1 The high activity of O2 kills cancer cells and achieves therapeutic effect. It sensitizes oxygen molecules to singlet oxygen ( 1 O2) originates from the excited triplet state of the photosensitizer. Heavy atom substitution can enhance the dye's electron spin-orbit coupling, thereby increasing intersystem crossing of electrons from the S1 state to the T1 state. Although many photosensitizers have been developed, their low singlet oxygen generation capacity and poor photostability have limited their further application in PDT. Therefore, researchers are actively searching for and improving photosensitizers to enhance their singlet oxygen generation capacity and photostability. This will help further improve the effectiveness and application of PDT.
[0003] BODIPY fluorescent dyes possess numerous excellent optical properties, such as high absorbance, high fluorescence quantum yield, and excellent photostability. In-depth research has led to the development of various derivatives and functionalized BODIPY dyes. The triplet state of BODIPY is of great significance in fundamental photochemical research, photodynamic therapy, photocatalysis, and other fields. It plays a key role in these fields and provides a powerful tool and platform for related research. Summary of the Invention
[0004] The purpose of the present invention is to provide a photosensitizer with the advantages of high singlet oxygen generation ability, good photostability and the like.
[0005] Another object of the present invention is to provide the use of the above-mentioned photosensitizer in photodynamic therapy.
[0006] Another object of the present invention is to provide a method for preparing the above-mentioned photosensitizer.
[0007] The technical solutions of the present invention are as follows:
[0008] A preparation method and application of a brominated BODIPY photosensitizer, the chemical structure of the compound being:
[0009]
[0010] Ⅰ.
[0011] The synthesis method and application of the brominated BODIPY photosensitizer include the following synthesis path:
[0012] ;
[0013] The specific steps include:
[0014] (1) Compound 1 was dissolved in tetrahydrofuran, and NBS was added and stirred to obtain a reaction solution; the reaction solution was subjected to vacuum rotary evaporation to remove the solvent, and the compound 2 was obtained by separation through silica gel column chromatography;
[0015] (2) Compound 2, 4-cyanophenylboronic acid and the catalyst were dissolved in 1,4-dioxane, and then an aqueous solution of K2CO3 was added and heated to react to obtain a reaction solution; the reaction solution was subjected to reduced pressure rotary evaporation to remove the solvent, and the compound I was obtained by separation through silica gel column chromatography;
[0016] The molar feed ratio of compound 1 to NBS in step (1) is 1:1 to 3. By changing the feed ratio, compound 2 can be obtained with a higher yield.
[0017] The reaction temperature of step (1) is 0 ~ 60 ° C, and the reaction time is 0.1 ~ 1 h. Selecting appropriate reaction temperature and time can ensure that compound 2 is obtained in a short time with a higher yield.
[0018] The molar feed ratio of compound 2, 4-cyanophenylboronic acid, catalyst, and K2CO3 in step (2) is 1:1-8:0.01-0.05:1-8. By changing the feed ratio, compound I can be obtained with a higher yield.
[0019] The catalyst used in step (2) is tetrakistriphenylphosphine palladium or bis(triphenylphosphine)palladium dichloride. Selecting a suitable catalyst can ensure a higher yield of compound I.
[0020] The reaction temperature of step (2) is 50-120°C, and the reaction time is 0.5-4 h. Selecting appropriate reaction temperature and time can ensure that compound 2 is obtained in a short time with a higher yield.
[0021] The beneficial effects of the present invention are as follows:
[0022] 1. Compound I described in the present invention is an ideal organic small molecule photosensitizer with a high singlet oxygen generation capacity. It is used in photodynamic therapy and has good application prospects.
[0023] 2. The preparation method of compound I described in the present invention is simple and low-cost, and the obtained compound I has high singlet oxygen generation ability and strong photostability.
[0024] 3. The synthesis reaction conditions of Compound I described in the present invention are easy to control, the product purification is simple, and it has universal applicability. BRIEF DESCRIPTION OF THE DRAWINGS
[0025] Figure 1 is the hydrogen spectrum of compound Ⅰ obtained in Example.
[0026] Figure 2 is the carbon spectrum of compound Ⅰ obtained in Example.
[0027] Figure 3 is the mass spectrum of compound Ⅰ obtained in Example.
[0028] Figure 4 1 is the ultraviolet absorption spectrum of compound I obtained in Example 1 in different solvents.
[0029] Figure 5 1 is the fluorescence emission spectrum of compound I obtained in Example 1 in different solvents.
[0030] Figure 6 This is a spectrum diagram of the ability of Compound I obtained in Example to generate singlet oxygen in DMSO.
[0031] Figure 7 1 is a comparison chart of the singlet oxygen generation abilities of Compound I obtained in Example 1 and methylene blue (MB). DETAILED DESCRIPTION
[0032] The embodiments of the present invention will be described in detail below with reference to the examples. The specific amounts described in the examples are converted according to the ratios of the raw materials in the specification of the present invention. However, those skilled in the art will understand that the following examples are only used to illustrate the present invention and should not be construed as limiting the scope of the present invention.
[0033] Example 1
[0034] Compound 1 (358.0 mg, 1.0 mmol) was weighed and dissolved in tetrahydrofuran (15.0 mL). NBS (178.0 mg, 1.0 mmol) was added and stirred at room temperature for 1 h. After the reaction was completed as monitored by TLC, the reaction solution was evaporated under reduced pressure to remove the solvent and purified by chromatography on a silica gel column (PE:DCM=4:1, v / v) to obtain compound 2 with a yield of 12.5%.
[0035] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (73.5 mg, 0.5 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were weighed and dissolved in 1,4-dioxane (20.00 mL). A solution of K2CO3 (69.0 mg, 0.5 mmol) in water (0.5 mL) was added and the mixture was reacted at 90°C for 4 h. After the reaction was complete as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure and the product was purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain compound I with a yield of 18.6%.
[0036] Example 2
[0037] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL), and NBS (356.0 mg, 2.0 mmol) was added. The mixture was stirred at room temperature for 1 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to afford compound 2 in a yield of 58.6%. When the amount of NBS was doubled compared to that in Example 1, the yield increased by 46.1%.
[0038] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (73.5 mg, 0.5 mmol), and bis(triphenylphosphine)palladium dichloride (17.5 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of KCO (69.0 mg, 0.5 mmol) in water (0.5 mL) was added and the mixture was reacted at 90°C for 4 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure and purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I in a 6.3% yield. When bis(triphenylphosphine)palladium dichloride was used as the catalyst instead of tetrakistriphenylphosphine palladium, the yield decreased by 12.3% compared to Example 1.
[0039] Example 3
[0040] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL). NBS (534.0 mg, 3.0 mmol) was added and stirred at room temperature for 1 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The product was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to afford compound 2 in a 16.3% yield. When the amount of NBS was doubled compared to Example 1, the yield increased by 3.8%.
[0041] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (294 mg, 2 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of KCO (276.0 mg, 2 mmol) in water (1.5 mL) was added and the mixture was reacted at 90°C for 4 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I in a yield of 42.5%. When the amounts of 4-cyanophenylboronic acid and KCO were each increased by threefold compared to Example 1, the yield increased by 23.9%.
[0042] Example 4
[0043] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL). NBS (445.0 mg, 2.5 mmol) was added and stirred at room temperature for 1 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The product was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to afford compound 2 in a 39.3% yield. When the amount of NBS was increased by 1.5 times compared to Example 1, the yield increased by 26.8%.
[0044] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (588.0 mg, 4 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of KCO (552.0 mg, 4 mmol) in water (2.0 mL) was added and the mixture was reacted at 90°C for 4 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I in a yield of 22.5%. When the amounts of 4-cyanophenylboronic acid and KCO were each increased by 7-fold compared to Example 1, the yield increased by 3.9%.
[0045] Example 5
[0046] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL). NBS (267.0 mg, 1.5 mmol) was added and stirred at room temperature for 1 h. After completion of the reaction as monitored by TLC, the reaction solution was evaporated under reduced pressure to remove the solvent. The product was purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to obtain compound 2 in a 45.8% yield. When the amount of NBS was increased by 0.5 times compared to Example 1, the yield increased by 33.3%.
[0047] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (588.0 mg, 4 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of KCO (414.0 mg, 3 mmol) in water (1.8 mL) was added and the mixture was reacted at 90°C for 4 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I in a yield of 45.6%. When the amount of KCO was reduced by half compared to Example 4, the yield increased by 26.1%. Increasing the amount of 4-cyanophenylboronic acid did not significantly affect the yield of Compound I, but varying the amount of KCO did.
[0048] Example 6
[0049] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL). NBS (320.4 mg, 1.8 mmol) was added and stirred at room temperature for 1 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The product was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to afford compound 2 in a yield of 59.6%. When the amount of NBS was increased by 0.8 times compared to Example 1, the yield increased by 47.1%.
[0050] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (294.0 mg, 2 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of KCO (414.0 mg, 3 mmol) in water (1.8 mL) was added and the mixture was reacted at 90°C for 3 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure and the mixture was purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I with a yield of 44.0%. When the reaction time was reduced by 1 h compared to Example 5, the yield decreased by 1.6%.
[0051] Example 7
[0052] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL), and NBS (320.4 mg, 1.8 mmol) was added. The mixture was stirred at room temperature for 40 min. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to obtain compound 2 in a 67.2% yield. When the reaction time was reduced by 20 min compared to Example 6, the yield increased by 7.6%.
[0053] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (294.0 mg, 2 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of KCO (414.0 mg, 3 mmol) in water (1.8 mL) was added and the mixture was reacted at 90°C for 2 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I with a yield of 48.6%. When the reaction time was reduced by 2 h compared to Example 5, the yield increased by 3.0%. Changing the reaction time did not significantly affect the yield of Compound I.
[0054] Example 8
[0055] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL), and NBS (320.4 mg, 1.8 mmol) was added. The mixture was stirred at room temperature for 20 min. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to afford compound 2 in a 64.6% yield. Reducing the reaction time by 40 min compared to Example 6 increased the yield by 5.0%.
[0056] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (294.0 mg, 2 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of K2CO3 (414.0 mg, 3 mmol) in water (1.8 mL) was added and the mixture was reacted at 120°C for 2 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure and purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I with a yield of 38.5%. When the reaction temperature was increased by 30°C compared to Example 7, the yield decreased by 10.1%.
[0057] Example 9
[0058] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL). NBS (320.4 mg, 1.8 mmol) was added and stirred at room temperature for 30 min. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to afford compound 2 in a yield of 76.8%. When the reaction time was reduced by 30 min compared to Example 6, the yield increased by 17.2%.
[0059] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (294.0 mg, 2 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of KCO (414.0 mg, 3 mmol) in water (1.8 mL) was added and the mixture was reacted at 50°C for 2 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure and purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I in a yield of 21.5%. When the reaction temperature was reduced by 40°C compared to Example 7, the yield decreased by 21.7%.
[0060] Example 10
[0061] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL), and NBS (320.4 mg, 1.8 mmol) was added. The mixture was stirred at 60°C for 30 min. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The product was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to obtain compound 2 in a yield of 75.0%. When the reaction temperature was increased by 35°C relative to that in Example 9, the yield decreased by 1.8%. Changing the reaction temperature did not significantly affect the yield of compound 2.
[0062] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (294.0 mg, 2 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of K2CO3 (414.0 mg, 3 mmol) in water (1.8 mL) was added and the mixture was reacted at 80°C for 2 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure and purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I with a yield of 40.2%. When the reaction temperature was reduced by 10°C compared to Example 7, the yield decreased by 8.4%.
[0063] Example 11
[0064] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL), and NBS (320.4 mg, 1.8 mmol) was added. The mixture was stirred at 0°C for 30 min. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The product was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to obtain compound 2 in a yield of 75.6%. When the reaction temperature was reduced by 25°C compared to Example 9, the yield decreased by 1.2%. Changing the reaction temperature did not significantly affect the yield of compound 2.
[0065] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (294.0 mg, 2 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in toluene (20.00 mL). A solution of K2CO3 (414.0 mg, 3 mmol) in water (1.8 mL) was added and the mixture was reacted at 90°C for 2 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure and purified by silica gel column chromatography (PE:DCM = 3:1, v / v) to obtain Compound I in an 8.5% yield. When toluene was used as the reaction solvent instead of 1,4-dioxane, the yield decreased by 40.1%, compared to Example 7.
[0066] Example 12
[0067] Compound 1 (358.0 mg, 1.0 mmol) was dissolved in tetrahydrofuran (15.0 mL), and NBS (320.4 mg, 1.8 mmol) was added. The mixture was stirred at room temperature for 30 min. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure. The mixture was then purified by silica gel column chromatography (PE:DCM = 4:1, v / v) to afford compound 2 in a 76.8% yield. Screening of reaction conditions revealed the most suitable conditions to be the addition of 1.8 equivalents of NBS and a reaction time of 30 min at room temperature.
[0068] Compound 2 (258.0 mg, 0.5 mmol), 4-cyanophenylboronic acid (294.0 mg, 2 mmol), and tetrakistriphenylphosphine palladium (28.8 mg, 0.025 mmol) were dissolved in 1,4-dioxane (20.00 mL). A solution of K₂CO₃ (414.0 mg, 3 mmol) in water (1.8 mL) was added and the mixture was reacted at 90°C for 2 h. After completion of the reaction as monitored by TLC, the solvent was removed by rotary evaporation under reduced pressure and the mixture was purified by silica gel chromatography (PE:DCM = 3:1, v / v) to obtain compound I in a 48.6% yield. Screening of reaction conditions revealed the most suitable reaction conditions: 4 equivalents of 4-cyanophenylboronic acid, 6 equivalents of K₂CO₃, and tetrakistriphenylphosphine palladium as the catalyst, at 90°C for 2 h.
[0069] Example 13
[0070] The compound I obtained in Example 1 was subjected to the following tests.
[0071] 1. Spectral properties test of compound I
[0072] Weigh compound I (5.38 mg, 0.01 mmol) and dissolve it in 1 mL of dichloromethane to a concentration of 10 -2 6 μL of the mother solution was dissolved in 3 mL of dichloromethane to a concentration of 2×10 -5 The test solution of M was tested in different solvents for UV-visible absorption and fluorescence emission spectra detection. The results were as follows: Figure 4 and Figure 5 shown. Figure 4 The maximum UV absorption peaks of compound I in toluene are 542 nm and 583 nm. Figure 2 The maximum fluorescence emission peaks of compound I were 603 nm and 647 nm.
[0073] 2. Test of compound I's ability to produce singlet oxygen
[0074] In this experiment, 1,3-diphenylisobenzofuran (DPBF) was used as a probe to detect the generation of singlet oxygen. Compound I and methylene blue (MB) were prepared in DMSO as solvent to form a 10 -2 A standard solution of M was prepared, and DPBF was prepared into a 5 mM standard solution using DMSO as the solvent. A certain amount of DPBF standard solution was mixed with a certain amount of compound I or MB standard solution and the volume was adjusted to 3 mL with DMSO. The prepared sample solution was transferred to a quartz glass dish and placed in a dark room. A 570 ~ 580 nm LED lamp was used as the light source and irradiated for different lengths of time. The absorbance of the sample solution was detected by a UV-visible spectrophotometer, and the generation of singlet oxygen was detected by recording the change in the absorbance value of DPBF at 417 nm. The results were as follows: Figure 6 and Figure 7 shown. Figure 6 The decrease in the DPBF absorbance value indicates the generation of singlet oxygen. Figure 7 The fitting slopes of compound I and MB are shown. Using MB as a reference, the singlet oxygen quantum yield of compound I was calculated to be 0.77.
[0075] The above embodiments are merely preferred technical solutions of the present invention and should not be construed as limiting the present invention. The embodiments and features in the embodiments of this application may be arbitrarily combined with each other unless they conflict. The scope of protection of the present invention shall be the technical solutions described in the claims, including equivalent alternatives to the technical features of the technical solutions described in the claims. Equivalent alternatives and improvements within this scope are also within the scope of protection of the present invention.
Claims
1. A brominated BODIPY-containing photosensitizer, characterized in that: The chemical structural formula of the photosensitizer is shown below: Ⅰ。 2. The method for preparing a brominated BODIPY photosensitizer according to claim 1, wherein: The method comprises the following synthetic route: (1) Compound 1 was dissolved in tetrahydrofuran, and N-bromosuccinimide was added, and the mixture was stirred to react to obtain a reaction solution; the reaction solution was subjected to reduced pressure rotary evaporation to remove the solvent, and the compound 2 was obtained by separation through silica gel column chromatography; (2) Compound 2, 4-cyanophenylboronic acid and the catalyst were dissolved in 1,4-dioxane, and K2CO3 solution was added. The mixture was heated and stirred to obtain a reaction solution. The reaction solution was subjected to reduced pressure rotary evaporation to remove the solvent, and the compound I was obtained by separation through silica gel column chromatography.
3. The method according to claim 2, characterized in that In the step (1), the molar ratio of compound 1 to NBS is 1:1 to 3.
4. The method according to claim 2, characterized in that In the step (1), the reaction temperature is 0 to 60°C and the reaction time is 0.1 to 1 h.
5. The optical method according to claim 2, wherein: In the step (1), the order of adding materials is compound 1, tetrahydrofuran, and NBS.
6. The method according to claim 2, characterized in that In the step (2), the molar ratio of compound 2, 4-cyanophenylboronic acid, catalyst, and K2CO3 is 1:1-8:0.01-0.05:1-8.
7. The method according to claim 2, characterized in that In the step (2), the catalyst is selected from tetrakistriphenylphosphine palladium or bis(triphenylphosphine)palladium dichloride.
8. The method for preparing a photosensitizer according to claim 2, wherein In the step (2), the reaction temperature is 50 to 120°C, and the reaction time is 0.5 to 4 h.
9. The method according to claim 2, characterized in that In the step (2), the order of adding materials is compound 2, 4-cyanophenylboronic acid, catalyst, 1,4-dioxane, and K2CO3 aqueous solution.
10. Use of the brominated BODIPY-containing photosensitizer according to claim 1 as a photosensitizer in photodynamic therapy for non-disease diagnosis and treatment.