Aggregation-induced emission platinum complex, preparation method and application of aggregation-induced emission platinum complex as photodynamic antitumor drug

Abstract

The invention relates to an aggregation-induced emission platinum complex, a preparation method and application of the aggregation-induced emission platinum complex as a photodynamic antitumor drug in the field of biological medicine. According to the aggregation-induced emission platinum complexes c-Pt-TPE and t-Pt-TPE, the platinum complexes are combined with the aggregation-induced emission photosensitizer and combined with PDT for use, the defects of platinum drugs are effectively overcome, the complexes have a strong photo-assisted inhibition effect on tumor cells, a new molecular basis is provided for development of cancer treatment drugs, and the aggregation-induced emission platinum complexes have good application prospects. The defects of existing platinum drugs are overcome, and the compound has excellent medicinal performance in the aspects of drug resistance and cytotoxicity resistance.

Description

Technical Field

[0001] The present invention belongs to the field of biomedicine, and particularly relates to an aggregation-induced luminescence platinum complex, a preparation method and an application thereof as a photodynamic anti-tumor drug, specifically to the design of a tetraphenyl derivative-platinum complex. Background Art

[0002] The occurrence of malignant tumors is a major threat to human life and health today. Researchers have long been committed to the development of highly effective anti-tumor drugs. Cisplatin, as a classic anti-tumor drug, is currently widely used in clinical practice and has achieved good therapeutic effects. The disadvantage of existing platinum compounds is that they are prone to induce tumor resistance and side effects, such as cardiotoxicity, ototoxicity, hepatotoxicity and nephrotoxicity. Therefore, one of the directions for structural modification of platinum compounds is to maintain their good anti-tumor effects while reducing their side effects.

[0003] Photodynamic therapy (PDT) is gradually being used in contemporary medicine, bringing new hope for the treatment of a variety of diseases, such as drug-resistant bacterial infections and malignant tumors. Unlike chemotherapy, PDT therapy uses photosensitizers for treatment. Under the appropriate excitation wavelength, the photosensitizer is excited and produces reactive oxygen species (ROS) through photochemical / physical processes. The generated ROS can inactivate biomacromolecules in the lesion site, thereby causing the death of pathogens or tumor cells. Compared with traditional chemotherapy, the advantage of PDT is that it is not easy to induce drug resistance in bacteria and tumors, and it still has a considerable killing effect on drug-resistant bacteria and tumors. In particular, some photosensitizers in PDT therapy can kill tumor cells by disrupting the blood supply in tumor tissues and activating the immune system in addition to producing ROS to kill tumors. Combined with modern medicine, PDT therapy can achieve selective administration to lesion tissues, avoiding damage to healthy tissues to a certain extent, that is, reducing toxic side effects.

[0004] The three elements of PDT therapy are light source, oxygen and the properties of photosensitizer. The role of photosensitizer is to convert oxygen in tissue into ROS, so the properties of photosensitizer largely determine the therapeutic effect. Photosensitizers can be divided into two types: aggregation quenching (ACQ) and aggregation induced emission (AIE). Among them, ACQ photosensitizers have a relatively low fluorescence quantum yield in a physiological environment, and the process of photoinduced ROS is blocked, with a relatively low ROS yield. AIE photosensitizers have a higher fluorescence quantum yield and photoinduced ROS yield in a physiological environment. In addition, at the molecular structure level of photosensitizers, the introduction of heavy atoms (such as transition metals: platinum, iridium, ruthenium and halogens: bromine, iodine) can increase the ROS yield of photosensitizers. Therefore, combining heavy atoms with AIE photosensitizers is a potential strategy to improve the efficacy of PDT.

[0005] In the prior art, the Chinese patent specification with publication number CN114940691A discloses a bifunctional cisplatin derivative cBBP containing a fluorescent group, cis-bis(fluoroboron dipyrrole)-methylenepyridine-diaminoplatin (II) nitrate (cBBP) made of fluorescent molecules, aromatic heterocycles and cisplatin, which has good photodynamic bactericidal effect and has a certain potential to overcome the drug resistance of tumor cells. However, its photodynamic anti-tumor effect still needs to be further improved, and one of the methods is to replace the photosensitive unit. Aggregation-induced emission building blocks are new photosensitive units in recent years, so the application attempts to use the basic aggregation-induced emission unit to improve the cBBP fluoroboron dipyrrole unit and conduct photodynamic anti-tumor effect tests. Summary of the invention

[0006] In response to the application demand of prior art platinum drugs in photodynamic therapy, the present invention provides an aggregation-induced luminescence platinum complex with excellent cytotoxicity, which has good resistance to tumor cells under photodynamic targeted excitation.

[0007] The present invention first provides an aggregation-induced luminescence platinum complex, including a tetraphenylethylene derivative-cisplatin complex c-Pt-TPE and / or a tetraphenylethylene derivative-transplatinum complex t-Pt-TPE, the structural formulas of which are as follows: .

[0008] The aggregation-induced luminescence platinum complexes c-Pt-TPE and t-Pt-TPE of the present invention have the following advantages: (1) Compared with traditional photosensitizers, the aggregation-induced fluorescent complex of the present invention has a higher reactive oxygen species (ROS) yield and higher light-assisted anti-tumor activity, and is not prone to induce tumor resistance. It is a new type of photosensitizing active unit, which can increase the ROS yield to a certain extent, thereby improving the photodynamic anti-tumor effect.

[0009] To further achieve the purpose of the present invention, the present invention also provides a method for preparing the above-mentioned aggregation-induced emission platinum complex, characterized in that the platinum complex c-Pt-TPE and t-Pt-TPE are prepared by the following steps: Step 1) 1,1,2-triphenyl-2-(4-bromophenyl)ethylene and 4-phenylboronic acid pyridine are reacted in a mixed solvent of tetrahydrofuran, methanol and water under the catalysis of tetrakistriphenylphosphine palladium and with potassium carbonate as an acid-binding agent, and then heated and separated by silica gel chromatography to obtain the intermediate product 1,1,2-triphenyl-2-(4-(4-pyridyl)phenyl)ethylene. The reaction formula is as follows: ; Step 2) Dissolve cis-diamminedichloroplatinum and trans-diamminedichloroplatinum in N,N-dimethylformamide respectively, then add silver nitrate, and after the reaction at room temperature, centrifuge to remove the precipitate. The obtained supernatant is the activated platinum salt. The reaction formula is as follows: ; Step 3) The products of step 1) and step 2) are dissolved in N,N-dimethylformamide at room temperature, reacted overnight under nitrogen protection, and purified to obtain c-Pt-TPE and t-Pt-TPE, respectively. The reaction formula is as follows: .

[0010] Compared with platinum photosensitizer complexes with the same function, the preparation and separation processes of the two complexes of the invention are simple and the yield is considerable.

[0011] Furthermore, in step 1), the volume ratio of solvent tetrahydrofuran (THF), methanol (MeOH), and water in the reaction solution is 1:1:2; the molar ratio of 1,1,2-triphenyl-2-(4-bromophenyl)ethylene, 4-phenylboronic acid pyridine, tetrakistriphenylphosphine palladium, and potassium carbonate is 100:110:5:100, wherein the concentration of 1,1,2-triphenyl-2-(4-bromophenyl)ethylene relative to the mixed solvent is 0.010M.

[0012] Furthermore, in step 1), the reaction temperature is 115-125° C., and the reaction time is 18-24 hours; after the reaction, the reaction solvent is removed using a rotary evaporator, and the crude product is separated and purified by a silica gel column, wherein the silica gel powder has a specification of 200-300 mesh, and the chromatographic eluent is petroleum ether:ethyl acetate in a volume ratio of 10:1.

[0013] Further, in step 2), N,N-dimethylformamide is the reaction solvent, silver nitrate is the activator, the concentration of cis-diamminedichloroplatinum or trans-diamminedichloroplatinum relative to N,N-dimethylformamide is 0.01M, and the molar ratio of silver nitrate to cis-diamminedichloroplatinum or trans-diamminedichloroplatinum is 220:100; the reaction temperature in this step is 20-30°C, and the reaction time is 24-36 hours; the supernatant after the reaction is completed is taken to obtain the activated platinum salt.

[0014] Furthermore, in step 3), the molar ratio of 1,1,2-triphenyl-2-(4-(4-pyridyl)phenyl)ethylene to activated platinum salt is 50:100, N,N-dimethylformamide is used as solvent, and the final concentration of platinum salt in this step is 0.005M.

[0015] Step 3) The reaction time is 24-36 hours. After the reaction is completed, the solvent is removed by distillation under reduced pressure. The crude product is recrystallized from a methanol-ether mixed solution with a volume ratio of 1:2-3 to obtain c-Pt-TPE or t-Pt-TPE.

[0016] The present invention also provides a use of the aggregation-induced luminescence platinum complex as a photodynamic anti-tumor drug. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of the c-Pt-TPE prepared in Example 1 of the present invention.

[0018] Figure 2 This is the hydrogen nuclear magnetic resonance spectrum of the t-Pt-TPE prepared in Example 1 of the present invention.

[0019] Figure 3 It is the UV-visible absorption spectrum of c-Pt-TPE and t-Pt-TPE in Example 2 of the present invention in the range of 300-600nm.

[0020] Figure 4 300-400 nm fluorescence emission spectra of c-Pt-TPE and t-Pt-TPE in Example 2 of the present invention.

[0021] Figure 5 The c-Pt-TPE and t-Pt-TPE in Example 2 of the present invention are at a light intensity of 40 mW / cm at 365 nm. 2 Fluorescence intensity change of DCFH solution at 488nm under irradiation, with a test time interval of 30.

[0022] Figure 6 The c-Pt-TPE and t-Pt-TPE in Example 2 of the present invention are at a light intensity of 40 mW / cm at 365 nm. 2 Absorption intensity change of ABDA solution at 378nm under irradiation, with a test time interval of 30s.

[0023] Figure 7 The c-Pt-TPE and t-Pt-TPE in the embodiment 2 of the present invention are prepared in different proportions of DMSO / H 2 O mixed solution.

[0024] Figure 8 This is a schematic diagram of incubating c-Pt-TPE and Panc-02 cells in Example 3 of the present invention for 24 hours and detecting cell viability using the CCK-8 kit.

[0025] Fig. 9The t-Pt-TPE in Example 3 of the present invention was incubated with Panc-02 cells for 4 h at 365 nm with a light intensity of 40 mW / cm 2 Schematic diagram of using the CCK-8 kit to detect cell viability after 15 minutes of irradiation and continued incubation for 20 hours.

[0026] Fig.10 For the comparative example c BBP was co-incubated with Panc-02 cells for 24 h and the cell survival rate was detected using the CCK-8 kit.

[0027] Fig.11 For comparative example c BBP was co-incubated with Panc-02 cells for 4 h under the light intensity of 40 mW / cm2 of white LED (300-800 nm). 2 Schematic diagram of using the CCK-8 kit to detect cell viability after 15 minutes of irradiation and continued incubation for 20 hours.

[0028] Fig.12 This is a schematic diagram of the comparative example in which tBBP was co-incubated with Panc-02 cells for 24 hours and the cell survival rate was detected using the CCK-8 kit.

[0029] Fig.13 In the comparative example, tBBP was co-incubated with Panc-02 cells for 4 h under a white light LED (300-800 nm) with a light intensity of 40 mW / cm 2 Schematic diagram of using the CCK-8 kit to detect cell viability after 15 minutes of irradiation and continued incubation for 20 hours. DETAILED DESCRIPTION

[0030] The technical solution of the present invention is further described below in conjunction with the accompanying drawings, but the present invention is not limited to the embodiments. Example 1

[0031] Preparation of c-Pt-TPE and t-Pt-TPE.

[0032] In this embodiment, two aggregation-induced emission platinum complexes were prepared, and their chemical structural formulas were: .

[0033] The specific preparation process of the complex of the above structural formula is as follows.

[0034] (1) Place 1,1,2-triphenyl-2-(4-bromophenyl)ethylene (41.01 mg, 0.1 mmol), 4-phenylboronic acid pyridine (13.54 mg, 0.11 mmol) and acid-binding agent potassium carbonate (13.80 mg, 0.1 mmol) in a 50 mL pressure bottle, add 2.5 mL of methanol solvent, 2.5 mL of tetrahydrofuran, and 5 mL of water, and fill the pressure bottle with nitrogen to expel oxygen, then add the catalyst tetrakistriphenylphosphine palladium (5.77 mg, 0.005 mmol). Under the protection of nitrogen atmosphere, heat the reaction mixture to 120°C and maintain for 24 hours. After the reaction is completed, pour the reaction mixture into 100 mL of water and extract with 30 mL of dichloromethane. The organic phase was collected and dried with anhydrous magnesium sulfate (300 mg), and then the organic phase was removed by rotary evaporator. The crude product was purified by chromatography on silica gel (200-300 mesh) with a volume ratio of 10:1 petroleum ether:ethyl acetate as the eluent. After purification, the product 1,1,2-triphenyl-2-(4-(4-pyridyl)phenyl)ethylene was obtained as a light yellow powder. The yield of this step was 79.60%; (2) Take cisplatin and reverse platinum (30.00 mg each, 0.1 mmol) (the following reaction process is carried out separately for cisplatin and reverse platinum) and place them in 50 ml round-bottom flasks. Add 10 ml of solvent N,N-dimethylformamide to each flask. After cisplatin (reverse platinum) is dissolved, add silver nitrate (37.16 mg, 0.22 mmol) to each flask. Stir at room temperature in the dark for 24 hours. After the reaction is completed, centrifuge to remove the silver chloride precipitate. The supernatant activated platinum salt is directly used for the next reaction without further treatment. (3) 1,1,2-Triphenyl-2-(4-(4-pyridyl)phenyl)ethylene (20.46 mg, 0.05 mmol) was placed in a 50 mL round-bottom flask, 10 mL of N,N-dimethylformamide solvent was added, and then 10 mL of the activated platinum salt solution in step (2) was added. The mixture was stirred at room temperature for 24 hours in the dark. After the reaction was completed, the solvent was removed by distillation under reduced pressure. The crude product was recrystallized from a methanol-ether mixed solution (methanol-ether volume ratio of 1:2-1:3) to separate the product. The product c-PT-TPE was a yellow solid powder, i.e., aggregation-induced emission platinum complexes c-Pt-TPE and t-Pt-TPE. The yield was 63.72%. Its H NMR spectrum was as follows: Figure 1 and Figure 2 shown. Figure 1 In the figure, the signals at 8.71, 7.87, 7.71, 7.14, and 6.99 ppm represent hydrogen signals in the aromatic region, and their integrated areas are consistent with the number of hydrogen atoms in the compound structure. The signal at 4.75 ppm is the hydrogen signal in the amino group, and its integrated area is consistent with the number of hydrogen atoms in the compound structure. Similarly, Figure 2Among them, the signals at 8.74, 8.04, 7.79, 7.17, and 7.0 ppm represent hydrogen signals in the aromatic region, and their integrated areas are consistent with the number of hydrogen atoms in the compound structure. The signal at 4.72 ppm is the hydrogen signal in the amino group, and its integrated area is consistent with the number of hydrogen atoms in the compound structure. Example 2

[0035] Detection of Photophysical / Chemical Properties of Aggregation-Induced Emission Platinum Complexes c-Pt-TPE and t-Pt-TPE In this example, the UV-visible absorption spectrum, fluorescence emission spectrum, and aggregation-induced luminescence properties were first characterized, and the DCFH and ABDA reactive oxygen species probes were used to perform photodynamic detection of c-Pt-TPE and t-Pt-TPE, i.e., the reactive oxygen species generation capacity. In the photodynamic detection and cytotoxicity experiments, the two complexes were prepared into a 1 mg / mL concentrated working solution, and the solvent was DMSO:H 2 O=1:9, it should be diluted accordingly in actual use.

[0036] (1) Characterization of UV-Vis absorption spectrum: The concentrated working solutions of the two complexes were diluted with dichloromethane to a final concentration of 10 μM and a volume of 2.5 mL. The solutions were placed in a 3 mL quartz cuvette and their UV-Vis absorption spectra were measured using a UV spectrophotometer with a detection wavelength range of 300-600 nm. The results are shown in Table 1. Figure 3 shown.

[0037] (2) Characterization of UV-Vis absorption spectrum: The concentrated working solutions of the two complexes were diluted with water to a final concentration of 11 μM and a volume of 2.5 mL. They were placed in a 3 mL quartz cuvette and their UV-Vis absorption spectra were measured using a UV spectrophotometer with a detection wavelength range of 300-400 nm. The results are shown in Table 1. Figure 4 shown.

[0038] (3) DCFH detection: First, add 0.5mL of 1mM DCFH-DA ethanol solution to 2ml of 0.01N NaOH and stir at room temperature for 30min. Then adjust the pH of the solution with 10ml of 25mM PBS with pH=7.4. During the test, take 10μL of 1mg / ml concentrated working solution of the complex and add it to 990μl of DCFH solution. After mixing, take 100μL to a 96-well plate and measure the fluorescence intensity at 0s with an enzyme-labeled instrument. Use 365nm (40mW / cm 2 ) and record the value every 30 seconds until 5 minutes have passed. Figure 5 As shown in the attached figure. DCFH is a ROS probe that can reflect the generation of ROS in the system. Figure 5As shown in the figure, both potential photosensitizer platinum complexes can generate ROS under the corresponding light source, and within the irradiation time range, t-Pt-TPE generates more ROS than c-Pt-TPE. When the illumination time is 5 minutes, the amount of ROS generated by t-Pt-TPE is about twice that of t-Pt-TPE.

[0039] (4) Aggregation-induced emission performance test: The concentrated working solutions of the two complexes were mixed with DMSO-H 2 O mixed solution dilution, where H 2 The volume of O was 1%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 99%, the final concentration of the complex was 1μM, the total volume of the mixed solution was 2.5mL, placed in a 3mL quartz cuvette, and the fluorescence spectra of the two complexes at different water contents were recorded using a fluorescence spectrometer in the range of 400-700nm. The results are shown in Figure 6 As shown, the fluorescence emission intensity of the two potential platinum complexes increases with the increase of water content in the system, which fully demonstrates its aggregation-induced emission effect. Example 3

[0040] Tumor cell cytotoxicity of complexes c-Pt-TPE and t-Pt-TPE (1) Dark toxicity test of c-Pt-TPE and t-Pt-TPE: First, add 3 mL of trypsin digestion solution to the Panc-02 cell (human pancreatic cancer cell) culture dish and wait for 4 minutes. After digestion, place the cells in a centrifuge tube and take 10 μL to a cell counting plate for counting. After centrifugation, add culture medium to make the cell count 10. 5 / mL cell suspension; 100 μL of cells were plated in each well of a 96-well plate. 5 / mL Panc-02 cells, incubate for 24 hours; add the two complex concentrated working solutions to the cells and incubate for 24 hours, then add CCK-8 and incubate for 1 hour, use an ELISA reader to measure the absorbance of each well in the 96-well plate at 450nm to detect the cell survival rate. The cell survival rate calculation formula is: .

[0041] The above experiment was repeated three times, and the results are as follows Figure 7 The experimental results were analyzed to obtain the half inhibitory concentration (IC) of c-Pt-TPE on Panc-02 cells under dark conditions. 50 ) was 51.52 μg / mL, and the corresponding IC of t-Pt-TPE on Panc-02 cells in the dark 50 >100 μg / mL.

[0042] (2) Dark toxicity test of c-Pt-TPE and t-Pt-TPE: According to the operation in step (1) of this embodiment, Panc-02 cells were seeded in a 96-well plate and incubated for 4 hours; the concentrated working solutions of the two complexes were added respectively, and after incubation with the cells for 4 hours, the light intensity was 40 mW / cm at 365 nm. 2 After irradiation for 15 min and incubation for 20 h, CCK-8 was added and incubated for 1 h. The absorbance of each well in the 96-well plate at 450 nm was measured using an ELISA instrument, and the cell survival rate was calculated using the same formula as in step (1) of this embodiment. The experimental results were analyzed to obtain the half inhibitory concentration (IC) of c-Pt-TPE on Panc-02 cells under light conditions. 50 ) was 0.13 μg / mL, and the results were as follows Figure 8 As shown; correspondingly, the IC of t-Pt-TPE on Panc-02 cells under illumination 50 is 2.01μg / mL. Figure 8 and 9 shown. Comparative Example

[0043] This comparative example conducted a comparative experiment on the cytotoxicity of the cisplatin complex cBBP disclosed in CN114940691A and the trans-platinum complex tBBP prepared by the same method, wherein the chemical structural formulas of the cisplatin complex cBBP and the trans-platinum complex tBBP are as follows: .

[0044] The light / toxicity test was conducted in Panc-02 cells. The only difference between the dark toxicity test and step (1) of Example 3 is the different complexes used. The difference between the light toxicity test and step (2) of Example 3 is that 1. the type of complex is different, 2. c The light source used by BBP and tBBP is white light LED (wavelength range is 300-800nm, light intensity is 40mW / cm 2 , illumination time is 15min). c Effect of BBP on the dark IC of Panc-02 cells 50 The value was 28.69 μg / mL, and the light IC 50 The value is 0.63μg / mL. c The dark cytotoxicity of BBP to Panc-02 cells is shown in Fig.10 , phototoxicity see Fig.11 . t Effect of BBP on the dark IC of Panc-02 cells 50 Value>100μg / mL, light IC 50 The value is 18.88μg / mL. t The dark cytotoxicity of BBP to Panc-02 cells is shown in Fig.12 , phototoxicity see Fig.13 A conclusive explanation is given for the toxicity results of the comparative experiment and the results of Example 3 to show that the complex of the present application has better performance.

[0045] Compare the c-Pt-TPE of this application with c The photodynamic anti-tumor effect of BBP can be found that for human pancreatic cancer cells, the illumination IC value of c-Pt-TPE is 0.13μg / mL, while the IC50 value of cBBP, a compound with the same platinum configuration, under the same illumination measurement conditions is 0.63μg / mL, which is about 21% of c-Pt-TPE. Similarly, the IC50 value of t-Pt-TPE is 2.01μg / mL, while the IC50 value of tBBP is 18.88μg / mL, which is only 11% of t-Pt-TP. Therefore, the platinum drug complex in this application has a significant improvement in the photodynamic anti-tumor effect.

Claims

1. An aggregation-induced emission platinum complex, characterized in that: It includes a tetraphenylethylene derivative-cisplatin complex c-Pt-TPE and / or a tetraphenylethylene derivative-transplatinum complex t-Pt-TPE, and the structural formulas are as follows: 。 2. A method for preparing the aggregation-induced emission platinum complex according to claim 1, characterized in that: The platinum complexes c-Pt-TPE and t-Pt-TPE are prepared by the following steps: Step 1) 1,1,2-triphenyl-2-(4-bromophenyl)ethylene and 4-phenylboronic acid pyridine are reacted in a mixed solvent of tetrahydrofuran, methanol and water under the catalysis of tetrakistriphenylphosphine palladium and with potassium carbonate as an acid-binding agent, and then heated and separated by silica gel chromatography to obtain the intermediate product 1,1,2-triphenyl-2-(4-(4-pyridyl)phenyl)ethylene. The reaction formula is as follows: ； Step 2) Dissolve cis-diamminedichloroplatinum and trans-diamminedichloroplatinum in N,N-dimethylformamide respectively, then add silver nitrate, and after the reaction at room temperature, centrifuge to remove the precipitate. The obtained supernatant is the activated platinum salt. The reaction formula is as follows: ； Step 3) The products of step 1) and step 2) are dissolved in N,N-dimethylformamide at room temperature, reacted overnight under nitrogen protection, and purified to obtain c-Pt-TPE and t-Pt-TPE, respectively. The reaction formula is as follows: 。 3. The preparation method according to claim 2, characterized in that: In step 1), the volume ratio of tetrahydrofuran (THF), methanol (MeOH) and water in the reaction solution is 1:1:2; the molar ratio of 1,1,2-triphenyl-2-(4-bromophenyl)ethylene, 4-phenylboronic acid pyridine, tetrakistriphenylphosphine palladium and potassium carbonate is 100:110:5:100, wherein the concentration of 1,1,2-triphenyl-2-(4-bromophenyl)ethylene relative to the mixed solvent is 0.010M.

4. The preparation method according to claim 2, characterized in that: In step 1), the reaction temperature is 115-125° C., and the reaction time is 18-24 hours. After the reaction is completed, the reaction solvent is removed using a rotary evaporator, and the crude product is separated and purified by a silica gel column, wherein the silica gel powder has a specification of 200-300 mesh, and the chromatographic eluent is petroleum ether:ethyl acetate in a volume ratio of 10:

1.

5. The preparation method according to claim 2, characterized in that: In step 2), N,N-dimethylformamide is the reaction solvent, silver nitrate is the activator, the concentration of cis-diamminedichloroplatinum or trans-diamminedichloroplatinum relative to N,N-dimethylformamide is 0.01M, and the molar ratio of silver nitrate to cis-diamminedichloroplatinum or trans-diamminedichloroplatinum is 220:100; the reaction temperature in this step is 20-30°C, and the reaction time is 24-36 hours; the supernatant after the reaction is completed is taken to obtain the activated platinum salt.

6. The preparation method according to claim 2, characterized in that: In step 3), the molar ratio of 1,1,2-triphenyl-2-(4-(4-pyridyl)phenyl)ethylene to activated platinum salt is 50:100, N,N-dimethylformamide is used as solvent, and the final concentration of platinum salt in this step is 0.005M.

7. The preparation method according to claim 2, characterized in that: Step 3) The reaction time is 24-36 hours. After the reaction is completed, the solvent is removed by distillation under reduced pressure. The crude product is recrystallized from a methanol-ether mixed solution with a volume ratio of 1:2-3 to obtain c-Pt-TPE or t-Pt-TPE.

8. Use of the aggregation-induced emission platinum complex according to claim 1 as a photodynamic anti-tumor drug.

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