An aggregation-induced luminescence anticancer photosensitizer and its preparation method and application

Abstract

The present invention discloses an aggregation-induced luminescence anticancer photosensitizer and its preparation method and application, which belong to the field of photodynamic therapy technology. The aggregation-induced luminescence anticancer photosensitizer provided by the present invention has significant aggregation-induced luminescence characteristics, and its unique rotor structure can overcome the fluorescence quenching effect caused by aggregation. In addition, the rotor structure characteristics of the aggregation-induced luminescence photosensitizer can effectively avoid the strong Π-Π effect between molecules in the aggregation state, which causes the active oxygen to be quenched, thereby causing the problem of poor photodynamic therapy effect. Secondly, the aggregation-induced luminescence anticancer photosensitizer has the ability to generate active oxygen, has a significant effect on killing cancer cells, can be used to prepare anticancer drugs, and has an application prospect for clinical photodynamic therapy. The preparation method of the aggregation-induced luminescence anticancer photosensitizer provided by the present invention is simple in process, low in raw material price, and low in production cost; low in temperature requirement, easy to control reaction process; easy to separate products, high in purity, and high in yield.

Description

Technical Field

[0001] The present invention relates to the technical field of photodynamic therapy, and in particular to an aggregation-induced luminescence anticancer photosensitizer and a preparation method and application thereof. Background Art

[0002] The causes of cancer are complex, including genetic factors, environmental factors, and lifestyle. Traditional cancer treatments mainly include surgical resection, chemotherapy, and radiotherapy, which have achieved certain results in treating cancer, but also have some limitations, such as damage to normal cells, side effects during treatment, and insensitivity to certain types of cancer.

[0003] Photodynamic therapy (PDT) is an emerging cancer treatment that combines photosensitizers, light of a specific wavelength, and oxygen molecules in tissues to selectively destroy tumor cells through photochemical reactions. The advantages of PDT lie in its unique mechanism and low side effects. It also has a synergistic effect and can be used in combination with other treatments such as chemotherapy, radiotherapy, or immunotherapy to produce a synergistic effect and improve the therapeutic effect. In addition, PDT has a wide range of indications and is suitable for many types of cancer, including skin cancer, lung cancer, esophageal cancer, and brain cancer. Although PDT has many advantages and is expected to become an important branch in the field of cancer treatment, providing patients with more treatment options. But it still faces some challenges, such as the selectivity of photosensitizers, the penetration depth of light, and the precise control of treatment. Therefore, the development of high-performance, highly selective photosensitizers remains the focus of research for those skilled in the art. Summary of the invention

[0004] The purpose of the present invention is to provide an aggregation-induced luminescence anticancer photosensitizer and its preparation method and application to solve the problems existing in the above-mentioned prior art. The aggregation-induced luminescence anticancer photosensitizer provided by the present invention can generate a large amount of active oxygen to kill cancer cells after light exposure, and has a very excellent anticancer effect.

[0005] To achieve the above object, the present invention provides the following solutions:

[0006] One of the technical solutions of the present invention: an aggregation-induced luminescence anticancer photosensitizer, the structural formula of which is shown in Formula I or Formula II:

[0007] , ;

[0008] Wherein, R1 is -H, -OCH3 (methoxy) or -C(CH3)3 (tert-butyl);

[0009] R2 is -F, -Cl, -Br, -I (halogen substituent) or -CN (cyano);

[0010] R3 is -C6H5 (phenyl), -CN (cyano), -COOH (carboxyl), -NH2 (amino), -CH3 (methyl), (including ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecayl, thirteencayl, tetradecyl, pentadecyl, hexadecyl, heptadecayl, octadecyl, nonadecayl, twenty-onecayl, twenty-twocayl) or (alkyl with quaternary ammonium salt at the end), n=0-20, take an integer;

[0011] X - Cl - Br - ,I - PF6 - CF3SO3 - or CF3SO2O - .

[0012] The aggregation-induced luminescence anticancer photosensitizer has a killing effect on cancer cells under light.

[0013] The second technical solution of the present invention: The preparation method of the above-mentioned aggregation-induced luminescence anticancer photosensitizer comprises the following steps:

[0014] Compound 1 and compound 2 are subjected to Suzukii coupling reaction to obtain compound 3, wherein compound 3 is reacted with 4-(4-pyridyl)phenylboronic acid (structural formula: ) The aggregation-induced luminescence anticancer photosensitizer (DFTBPPy for short) shown in formula I is obtained by Suzukii coupling reaction;

[0015] The aggregation-induced luminescence anticancer photosensitizer shown in formula I reacts with compound 4 to obtain the aggregation-induced luminescence anticancer photosensitizer shown in formula II (abbreviated as cDFTBPPy);

[0016] The structural formula of compound 1 is shown in formula III, the structural formula of compound 2 is shown in formula IV, the structural formula of compound 3 is shown in formula V, and the structural formula of compound 4 is shown in formula VI:

[0017] , , , ;

[0018] Wherein, R1 is -H, -OCH3 or -C(CH3)3;

[0019] R2 is -F, -Cl, -Br, -I or -CN;

[0020] R3 is -C6H5, -CN, -COOH, -NH2, -CH3, or , n=0-20, take integer;

[0021] X is Cl, Br, I, PF6, CF3SO3 or CF3SO2O.

[0022] Furthermore, the Suzukii coupling reaction uses tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) as a catalyst, potassium carbonate (K2CO3) as a promoter, and toluene and water as solvents.

[0023] Furthermore, the compound 1 and compound 2 are reacted by Suzukii coupling reaction to obtain compound 3, which includes: the molar ratio of compound 1, compound 2, tetrakis(triphenylphosphine)palladium and K2CO3 is 1:1:0.04:4; the volume ratio of toluene and water is 3:1; the amount ratio of compound 1 and solvent (toluene + water) is 0.9 mmol:40 mL; the conditions of the Suzukii coupling reaction are heating the reaction at 90-120°C for 8-12 h.

[0024] Furthermore, the compound 3 and 4-phenylpyridine boronic acid are reacted through a Suzukii coupling reaction to obtain an aggregation-induced luminescence anticancer photosensitizer shown in formula I, which includes: the molar ratio of the compound 3, 4-phenylpyridine boronic acid, tetrakis(triphenylphosphine)palladium and K2CO3 is 1:1:0.03:8; the volume ratio of toluene and water is 3:1; the amount ratio of the compound 3 and the solvent (toluene + water) is 0.9 mmol:40 mL; the conditions of the Suzukii coupling reaction are heating the reaction at 90-120°C for 8-12 h.

[0025] Furthermore, the aggregation-induced luminescence anticancer photosensitizer shown in formula I reacts with compound 4 to obtain the aggregation-induced luminescence anticancer photosensitizer shown in formula II, including: the molar ratio of the aggregation-induced luminescence anticancer photosensitizer shown in formula I to compound 4 is 1:1; acetonitrile is used as solvent for the reaction; and the reaction conditions are heating the reaction at 60-80°C for 10-12h.

[0026] Furthermore, the synthetic route of the preparation method is as follows:

[0027] .

[0028] The third technical solution of the present invention: the use of the above-mentioned aggregation-induced luminescence anticancer photosensitizer in the preparation of anticancer drugs.

[0029] Furthermore, the anticancer drug is an anticancer drug that has inhibitory activity on cancer cells.

[0030] Technical solution 4 of the present invention: Application of the above-mentioned aggregation-induced luminescence anticancer photosensitizer in the preparation of photodynamic therapy drugs.

[0031] Furthermore, the photodynamic therapy drug is a drug that has an inhibitory effect on cancer cells under light conditions.

[0032] The present invention discloses the following technical effects:

[0033] The aggregation-induced luminescence anticancer photosensitizer provided by the present invention has significant aggregation-induced luminescence characteristics, and its unique rotor structure (such as containing triphenylamine groups) can overcome the fluorescence quenching effect caused by aggregation. In addition, the rotor structure characteristics of the aggregation-induced luminescence photosensitizer can effectively avoid the problem that the strong π-π effect between molecules in the aggregated state causes the active oxygen to be quenched, thereby making the photodynamic therapy effect poor. Secondly, the aggregation-induced luminescence anticancer photosensitizer has the ability to generate active oxygen, which has a significant effect on killing cancer cells. In summary, the aggregation-induced luminescence anticancer photosensitizer provided by the present invention has good lethality to cancer cells, can be used to prepare anticancer drugs, and has the potential to be used as a photosensitizer for effective photodynamic therapy.

[0034] The aggregation-induced luminescence anticancer photosensitizer provided by the present invention has good selectivity and has a good selective killing effect on cancer cells, but has no significant killing effect on normal cells.

[0035] The preparation method of the aggregation-induced luminescence anticancer photosensitizer provided by the present invention has a simple process, low raw material price, low production cost, low temperature requirement, and easy control of the reaction process; the product is easy to separate, high in purity and high in yield. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0037] Figure 1 The H NMR spectrum of the aggregation-induced luminescence anticancer photosensitizer (DFTBPPy) prepared in Example 1;

[0038] Figure 2 The aggregation-induced luminescence curve of the aggregation-induced luminescence anticancer photosensitizer (DFTBPPy) prepared in Example 1; wherein a is an ultraviolet absorption spectrum, b is a fluorescence emission spectrum, and c is an aggregation-induced luminescence curve;

[0039] Figure 3 The results of the ROS production efficiency test of the photosensitizer;

[0040] Figure 4The results of the toxicity test of the aggregation-induced luminescence anticancer photosensitizer (DFTBPPy) prepared in Example 1 on cancer cells, where ac is a 450 nm laser (30 mW / cm 2 The effects of different concentrations of DFTBPPy on the viability (cell survival rate) of cancer cells 5637, SW780 and normal cells NIH-3T3 under irradiation (15 min, 25 min). de is the fluorescent staining image of cancer cells 5637 and SW780 after light irradiation. DETAILED DESCRIPTION

[0041] Various exemplary embodiments of the present invention will now be described in detail. This detailed description should not be considered as limiting the present invention, but should be understood as a more detailed description of certain aspects, features, and embodiments of the present invention.

[0042] It should be understood that the terms described in the present invention are only for describing a particular embodiment and are not intended to limit the present invention. In addition, for the numerical range in the present invention, it should be understood that each intermediate value between the upper and lower limits of the scope is also specifically disclosed. The intermediate value in any stated value or stated range, and each smaller range between any other stated value or intermediate value in the described range is also included in the present invention. The upper and lower limits of these smaller ranges can be independently included or excluded in the scope.

[0043] Unless otherwise indicated, all technical and scientific terms used herein have the same meanings as those generally understood by those skilled in the art. Although the present invention describes only preferred methods and materials, any methods and materials similar or equivalent to those described herein may also be used in the implementation or testing of the present invention. All documents mentioned in this specification are incorporated by reference to disclose and describe the methods and / or materials associated with the documents. In the event of a conflict with any incorporated document, the content of this specification shall prevail.

[0044] It will be apparent to those skilled in the art that various modifications and variations may be made to the specific embodiments of the present invention description without departing from the scope or spirit of the present invention. Other embodiments derived from the present invention description will be apparent to the skilled artisan. The present invention description and examples are exemplary only.

[0045] The words “include,” “including,” “have,” “contain,” etc. used in this document are open-ended terms, meaning including but not limited to.

[0046] All raw materials and reagents used in the specific embodiments of the present invention are common commercially available products.

[0047] Example 1

[0048] An aggregation-induced luminescence anticancer photosensitizer (DFTBPPy), the synthesis route is:

[0049] ;

[0050] Among them, R1 is -H and R2 is -F.

[0051] The specific preparation steps are as follows:

[0052] (1) Preparation of compound 3

[0053] Compound 1 (1.5 g, 4.5 mmol), compound 2 (1.3 g, 4.5 mmol), potassium carbonate (2.49 g, 18 mmol) and tetrakis(triphenylphosphine)palladium (197 mg, 0.17 mmol) were added to a 500 mL double-necked round-bottom flask, and 150 mL of distilled toluene and 50 mL of water were added to obtain a mixture. The mixture was then heated to reflux at 110°C under nitrogen for 10 h. After cooling to room temperature, the product was poured into water and extracted three times with dichloromethane. The organic phase was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration and solvent evaporation, it was purified by silica gel column chromatography using a mixture of ethyl acetate / petroleum ether (1 / 8, v / v) as the eluent to obtain compound 3, which was a yellow solid with a yield of 51% (1.13 g).

[0054] The nuclear magnetic resonance hydrogen spectrum analysis data of compound 3 is:

[0055] 1 H NMR (400 MHz, CDCl3): δ 7.67-7.65 (m, 2H), 7.33-7.29 (m, 4H), 7.21-7.17 (m, 6H), 7.12-7.08 (m, 2H).

[0056] (2) Preparation of aggregation-induced emission anticancer photosensitizer (DFTBPPy)

[0057] Compound 3 (1.0 g, 2.02 mmol), 4-(4-pyridyl)phenylboronic acid (0.4 g, 2.02 mmol), potassium carbonate (2.23 g, 16 mmol) and tetrakis(triphenylphosphine)palladium (70.03 mg, 0.06 mmol) were added to a 500 mL double-necked round-bottom flask, and 150 mL of distilled toluene and 50 mL of water were added to obtain a mixture. The mixture was then heated to reflux at 110°C under nitrogen for 10 h. After cooling to room temperature, the product was poured into water and extracted three times with dichloromethane. The organic phase was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration and solvent evaporation, the product was purified by silica gel column chromatography using a mixture of ethyl acetate / petroleum ether (1 / 10, v / v) as the eluent to obtain a solid compound DFTBPPy with a yield of 60% (689 mg).

[0058] The hydrogen nuclear magnetic resonance spectrum of DFTBPPy prepared in this example is as follows: Figure 1 As shown, the parsed data is:

[0059] 1 H NMR (400 MHz, CDCl3, δ ppm): δ 8.74 (d, 2H, J = 3.5 Hz), 8.01 (d, 2H, J =7.4 Hz), 7.88 (d, 2H, J = 8.4 Hz), 7.76-7.73 (m, 2H), 7.72-7.67 (m, 2H), 7.34-7.30 (m, 4H), 7.23-7.20 (m, 6H), 7.12 (t, 2H, J = 4.9 Hz). 13 C NMR (100 MHz,CDCl3): δ 150.2, 149.5, 149.4, 148.8, 148.7, 148.6, 148.5, 147.1, 131.8, 131.4,131.3, 129.4, 128.8, 127.2, 125.4, 123.8, 122.1, 121.5.

[0060] Example 2

[0061] Same as Example 1, except that R1 in the synthesis route is -OCH3 and R2 is -F. The yield of DFTBPPy prepared in this example is 58% (735 mg). The H NMR spectrum analysis data is:

[0062] 1 H NMR (400 MHz, CDCl3, δ ppm): δ 8.84 (d, 2H, J = 3.2 Hz), 8.01 (d, 2H, J =7.2 Hz), 7.81 (d, 2H, J = 8.2 Hz), 7.75-7.72 (m, 2H), 7.70-7.65 (m, 2H), 7.32-7.30 (m, 4H), 7.13-7.10 (m, 6H), 3.77 (s, 6H).

[0063] Example 3

[0064] An aggregation-induced luminescence anticancer photosensitizer (cDFTBPPy), the synthesis route is:

[0065] ;

[0066] Wherein, R1 is -H, R2 is -F, R3 is -CH3, and X is I (X - For I - ).

[0067] The specific preparation steps are as follows:

[0068] DFTBPPy (568 mg, 1 mmol) and iodomethane (141 mg, 1 mmol) prepared in Example 1 were added to a 250 mL double-necked round-bottom flask, and 100 mL of acetonitrile was added to obtain a mixture. The mixture was then heated at 70 °C under nitrogen for 10 h. After cooling to room temperature, the product was poured into water and extracted three times with dichloromethane. The organic phase was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration and solvent evaporation, the product was purified by silica gel column chromatography using a methanol / dichloromethane mixture (1 / 10, v / v) as the eluent to obtain a solid compound cDFTBPPy with a yield of 80% (568 mg).

[0069] The nuclear magnetic resonance hydrogen spectrum analysis data of cDFTBPPy prepared in this example is:

[0070] 1 H NMR (400 MHz, CDCl3, δ ppm): δ 8.94 (d, 2H, J = 3.6 Hz), 8.51 (d, 2H, J =7.4 Hz), 7.85 (d, 2H, J= 8.4 Hz), 7.77-7.72 (m, 2H), 7.73-7.66 (m, 2H), 7.36-7.30 (m, 4H), 7.25-7.20 (m, 6H), 7.10 (t, 2H, J = 4.9 Hz), 4.39 (s, 3H).

[0071] Test Example 1

[0072] Aggregation-induced emission performance test of photosensitizer

[0073] The aggregation-induced luminescence anticancer photosensitizer DFTBPPy prepared in Example 1 was tested for aggregation-induced luminescence performance, and the test method was as follows: 11 sample tubes were taken, and 0 μL, 270 μL, 570 μL, 870 μL, 1170 μL, 1470 μL, 1770 μL, 2070 μL, 2370 μL, 2670 μL and 2970 μL tetrahydrofuran were added respectively. In the above sample tubes, 30 μL of 1 mmol / L DFTBPPy dispersion was added respectively and mixed evenly. In the above sample tubes, 2970 μL, 2670 μL, 2370 μL, 2070 μL, 1770 μL, 1470 μL, 1170 μL, 870 μL, 570 μL, 270 μL and 0 μL water were added respectively. Each time one was added, it was mixed evenly in time, and the fluorescence spectrum was tested after one minute of standing.

[0074] Figure 2 The aggregation-induced luminescence curve of the aggregation-induced luminescence anticancer photosensitizer DFTBPPy prepared in Example 1, wherein a is the ultraviolet absorption spectrum, b is the fluorescence emission spectrum, and c is the aggregation-induced luminescence curve. Figure 2 It can be seen that the aggregation-induced luminescence anticancer photosensitizer prepared in Example 1 has good visible light absorption and can be applied to photodynamic therapy excited by visible light.

[0075] Test Example 2

[0076] Detection of reactive oxygen species (ROS) generation efficiency of photosensitizers

[0077] The ROS generation efficiency of the aggregation-induced luminescence anticancer photosensitizer DFTBPPy prepared in Example 1 was evaluated using the DCFH-DA probe, with commercial photosensitizers Ce6 and RB as controls. Under alkaline conditions, DCFH-DA is converted into 2,7-dichlorofluorescein (DCFH), and in the presence of ROS, it is converted into 2,7-dichlorofluorescein (DCF, excitation wavelength 488 nm, emission wavelength 525 nm, quantum yield 90%) with high fluorescence quantum yield. The photosensitizer to be tested was added to a solution of DCFH (40 µM) activated by NaOH, and the amount of photosensitizer added was 5 µM. At 5 mW / cm 2 The solution was irradiated under white light for 5 min, and the fluorescence emission intensity of the DCF solution at 525 nm was measured by a fluorescence meter every 30 s, with an excitation wavelength of 488 nm.

[0078] Test results such as Figure 3 As shown by Figure 3 It can be seen that under light, in the presence of photosensitizer, the fluorescence intensity of DCF increases rapidly, indicating that the photosensitizer has a strong efficiency in generating reactive oxygen species. Compared with commercial photosensitizers Ce6 and RB, the aggregation-induced luminescence anticancer photosensitizer DFTBPPy prepared in Example 1 has a stronger ability to generate reactive oxygen species.

[0079] Test Example 3

[0080] Toxicity test of photosensitizer on 5637 human bladder cancer cells, SW780 human bladder transitional cell carcinoma cells and normal cells NIH-3T3

[0081] Cells (5637, SW780 or NIH-3T3, all at a concentration of 1×10 5 / mL) were plated in a 96-well plate (100 μL per well), and each cell type was repeated in multiple wells for 24 hours. After the cells adhered to the wall, the culture medium was aspirated, and then 100 μL of the aggregation-induced luminescence anticancer photosensitizer DFTBPPy prepared in Example 1 was added to the multiple wells of each cell type at different concentrations (the concentrations were 0 μM, 0.31 μM, 0.63 μM, 1.25 μM, 2.5 μM, and 5.0 μM, respectively). After 30 minutes of action, 100 μL of culture medium (10wt% fetal bovine serum) was added to each well and cultured in a constant temperature incubator at 37°C, 5% CO2, and 95% humidity for 24 hours. Then, the supernatant was removed, 100 μL of CCK-8 was added, and cultured for 2 hours. The OD value at 450 nm was detected by a microplate reader.

[0082] Then, the phototoxicity of the aggregation-induced luminescence anticancer photosensitizer was studied. The 96-well plate of cells was subjected to 450 nm (30 mW / cm 2) After laser irradiation for 15 minutes, the cells were cultured for 12 hours (37°C, 5% CO2, 95% humidity), the supernatant was removed, and 100 μL CCK-8 was added for 2 hours as the experimental group with different concentrations of DFTBPPy. At the same time, 3 control groups were set up for 5637 and SW780 cells, among which control group 1 was the same as the above experimental steps (the concentration of added DFTBPPy was 5.0 μM), but no illumination was performed (referred to as cell + photosensitizer group); control group 2 was the same as the above experimental steps, and the concentration of added DFTBPPy was 0 μM, that is, only cells were added, no DFTBPPy was added, and no illumination was performed (referred to as cell group); control group 3 was the same as the above experimental steps, and the concentration of added DFTBPPy was 0 μM, that is, only cells were added, no DFTBPPy was added, but illumination was performed (referred to as cell group + illumination); finally, the 450 The OD value at nm was combined with the OD value before light irradiation to calculate the cell survival rate (OD value before light irradiation / OD value after light irradiation × 100%). The results are shown in Figure 4 As shown in ac in the figure, the cancer cells 5637 and SW780 were stained with the dead-live staining kit, and the experimental group (referred to as the cell + light + photosensitizer group) with a DFTBPPy concentration of 5.0 μM and three control groups were stained, and fluorescence images were taken. The results are shown in Figure 4 As shown in de (where calcein acetoxymethyl ester represents the staining of living cells, propidium iodide represents the staining of dead cells, and overlay represents the overlay of live and dead staining images). Figure 4 It can be seen that when the concentration of the aggregation-induced luminescence anticancer photosensitizer DFTBPPy is ≥2.5 μM, the killing effect on cancer cells 5637 and SW780 is obvious after illumination, the survival rate of cancer cells is low, and the phototoxicity of DFTBPPy is strong. In addition, its killing effect on normal cells is very weak, indicating that it has good selectivity.

[0083] In addition, the above method was used to test the DFTBPPy prepared in Example 2 and the cDFTBPPy prepared in Example 3 (both added at a concentration of 5.0 μM) under 450 nm laser (30 mW / cm 2 The effects of irradiation on the viability of cancer cells 5637 and SW780 (i.e., cell survival rate) are shown in Table 1:

[0084] Table 1

[0085]

[0086] As can be seen from Table 1, the DFTBPPy prepared in Example 2 and the cDFTBPPy prepared in Example 3 also have obvious killing effects on cancer cells 5637 and SW780 after irradiation with light, and both have strong phototoxicity.

[0087] The embodiments described above are only descriptions of the preferred modes of the present invention, and are not intended to limit the scope of the present invention. Without departing from the design spirit of the present invention, various modifications and improvements made to the technical solutions of the present invention by ordinary technicians in this field should all fall within the protection scope determined by the claims of the present invention.

Claims

1. An aggregation-induced luminescence anticancer photosensitizer, characterized in that: The structural formula is shown in Formula Ⅰ or Formula Ⅱ: ， ； In formula I, R1 is -H or -OCH3, and R2 is -F; In formula II, R1 is -H, R2 is -F, R3 is -CH3, X - For I - .

2. The method for preparing the aggregation-induced luminescence anticancer photosensitizer according to claim 1, characterized in that: The following steps are involved: Compound 1 and compound 2 are subjected to Suzukii coupling reaction to obtain compound 3, and compound 3 and 4-(4-pyridyl)phenylboronic acid are subjected to Suzukii coupling reaction to obtain an aggregation-induced luminescence anticancer photosensitizer as shown in formula I; The aggregation-induced luminescence anticancer photosensitizer shown in formula I reacts with compound 4 to obtain the aggregation-induced luminescence anticancer photosensitizer shown in formula II; The structural formula of compound 1 is shown in formula III, the structural formula of compound 2 is shown in formula IV, the structural formula of compound 3 is shown in formula V, and the structural formula of compound 4 is shown in formula VI: 、 、 、 ； Wherein, R1 is -H or -OCH3; R2 is -F; R3 is -CH3; X is 1.

3. The preparation method according to claim 2, characterized in that: The Suzukii coupling reaction uses tetrakis(triphenylphosphine)palladium as a catalyst, K2CO3 as a promoter, and toluene and water as solvents.

4. Use of the aggregation-induced luminescence anticancer photosensitizer according to claim 1 in the preparation of photodynamic therapy cancer drugs.

5. The use according to claim 4, characterized in that The photodynamic cancer therapy drug is a drug that has an inhibitory effect on cancer cells under light conditions.

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