A triphenylamine-modified metal iridium (III) complex and its preparation method and application

Abstract

The present invention belongs to the field of chemical pharmaceuticals and specifically relates to a triphenylamine-modified metal iridium (III) complex, its preparation method, and application. The metal iridium (III) complex is TPA-Ir1 or TPA-Ir2, with the structural formula: The metal iridium complex prepared by the present invention, the metal complex provided by the present invention, exhibits excellent anticancer activity. The compounds of the present invention have excellent fluorescence properties, facilitate the study of anticancer mechanisms, and provide a new approach for the subsequent research of anticancer drugs. The preparation method provided by the present invention has high substrate utilization, low difficulty coefficient in product separation and purification, and broad application prospects.

Description

Technical Field

[0001] The present invention belongs to the field of chemical pharmacy, and specifically relates to a triphenylamine-modified metal iridium (III) complex, a preparation method thereof, and an application thereof. Background Art

[0002] Cancer is a genetic disease characterized by invasiveness and metastasis, caused by malignant cell proliferation. When the body is exposed to long-term exposure to chemical, physical, and viral carcinogens, cells can undergo a series of genetic changes, including inactivation of tumor suppressor genes and activation of proto-oncogenes into oncogenes, ultimately leading to the formation of malignant tumors. To treat cancer, research teams both domestically and internationally are dedicated to discovering or synthesizing highly effective, low-toxicity anticancer drugs. Among the complex array of metallo-based drugs, organometallic iridium complexes have become a hot topic in anticancer drug research due to their excellent anticancer activity, targeting, and luminescent properties.

[0003] Currently, research on cyclometallated iridium(III) complexes primarily focuses on their luminescence properties. These excellent properties facilitate the study of the targeting, transport, and mechanism of action of anticancer drugs. However, most cyclometallated iridium(III) complexes suffer from low solubility and poor activity. Therefore, the search for cyclometallated iridium(III) complexes with excellent anticancer activity is of great significance.

[0004] Ir(III) anti-tumor complexes primarily have two structural types: cyclic and half-sandwich. Half-sandwich Ir(III) complexes typically lack suitable fluorescence, making them difficult to detect and subsequently investigate for anti-cancer mechanisms such as targeting and uptake. Therefore, developing half-sandwich Ir(III) complexes with suitable fluorescence properties for anti-cancer activity is of great significance. Summary of the Invention

[0005] In view of the problems existing in the prior art, the present invention provides a triphenylamine-modified metal iridium (III) complex.

[0006] The present invention also provides a method for preparing the triphenylamine-modified metal iridium (III) complex.

[0007] Another object of the present invention is to provide the use of triphenylamine-modified metal iridium (III) complexes in the preparation of anti-cancer targeted drugs.

[0008] The technical solutions adopted by the present invention to achieve the above-mentioned purpose are as follows:

[0009] The present invention provides a triphenylamine-modified iridium (III) complex. The iridium (III) complex is TPA-Ir1 or TPA-Ir2, and has the structural formula:

[0010] .

[0011] The present invention also provides a method for preparing the above-mentioned metal iridium (III) complex, comprising the following steps:

[0012] (1) Weigh the iridium dimer and ligand, add sodium acetate solution, evacuate the solution, fill it with nitrogen, and inject anhydrous methanol as solvent. Mix the solution and stir at room temperature to react. Then, heat it under reflux and detect the reaction by thin layer chromatography.

[0013] (2) After the reaction is completed, the solvent is removed by rotary evaporation under reduced pressure, dichloromethane is added to dissolve the precipitate and the precipitate is filtered, and n-hexane is added to the precipitate. After the solution evaporates completely, a reddish-brown solid powder TPA-Ir1 or a brownish-black solid powder TPA-Ir2 is obtained.

[0014] The structural formula of the ligand used in the synthesis of the target complex of the present invention is:

[0015] .

[0016] The structural formula of the metal iridium dimer used in the synthesis of the target complex of the present invention is:

[0017] .

[0018] Furthermore, in step (1), the mass ratio of the metal iridium dimer to the ligand is 26:57; and the ratio of the metal iridium dimer to the sodium acetate solution is 0.030 g:15-20 mL.

[0019] Furthermore, in step (1), the ligand is pre-dissolved in benzene, and the concentration in benzene is 1.7 mg / mL; the concentration of the sodium acetate solution is 0.4 mol / L.

[0020] Furthermore, in step (1), the stirring reaction time is 6 hours; and the heating reflux is reflux at 65° C. for 6 hours.

[0021] The present invention also provides the use of the triphenylamine-modified metal iridium (III) complex in the preparation of anticancer drugs.

[0022] The present invention also provides the use of the triphenylamine-modified metal iridium (III) complex in detecting the number of cells at different stages.

[0023] Furthermore, in step (1), the mass ratio of the metal iridium dimer to the ligand is 26:57; the concentration of the ligand in benzene is 1.9 mg / mL; and the ratio of the metal iridium dimer to sodium acetate is 0.030 g:15-20 mL.

[0024] The specific reaction scheme of the present invention is as follows:

[0025] .

[0026] In the present invention, a triphenylamine-containing ligand is reacted with a half-sandwich iridium dimer, Dimer 1, and a cyclometallated iridium dimer, Dimer 2, respectively, to obtain two triphenylamine-modified iridium (III) complexes, TPA-Ir1 and TPA-Ir2. The antiproliferative activities of the cyclometallated iridium complex and the half-sandwich iridium complex under the same ligand are compared, providing a reference for the subsequent research on triphenylamine-modified iridium (III) anticancer complexes.

[0027] To investigate the potential anticancer activity and biosafety of TPA-Ir1 and TPA-Ir2, the MTT assay was used to assess the in vitro proliferation of A549 cells, A549-DDP cells (cisplatin-resistant human lung adenocarcinoma cells), and Base-2B cells after 24 hours of treatment. The half-sandwich iridium complex exhibited antiproliferative activity comparable to that of cisplatin and significantly superior to the cycloiridium complex. Further investigation of the complex TPA-Ir1 revealed that it enters A549 cells via an energy-dependent pathway. Once inside, it targets the mitochondria, leading to a decrease in mitochondrial membrane potential and a surge in reactive oxygen species. Furthermore, TPA-Ir1 promotes late apoptosis by arresting the cell cycle in the S phase. Furthermore, TPA-Ir1 effectively inhibits A549 cell migration.

[0028] The beneficial effects of the present invention are:

[0029] (1) The metal iridium complex prepared by the present invention exhibits excellent anticancer activity, which is significantly better than that of platinum-based anticancer drugs;

[0030] (2) The metal iridium complex prepared by the present invention has good fluorescence properties, which is convenient for studying the anti-cancer mechanism;

[0031] (3) The preparation method provided by the present invention has high substrate utilization rate, low difficulty coefficient of product separation and purification, and broad application prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] Figure 1 is the H NMR spectrum of the complex TPA-Ir1 of the present invention;

[0033] Figure 2 is the mass spectrum of the complex TPA-Ir1 of the present invention;

[0034] Figure 3 is the H NMR spectrum of the complex TPA-Ir2 of the present invention;

[0035] Figure 4 is the mass spectrum of the complex TPA-Ir2 of the present invention;

[0036] Figure 5 This is a cell tissue targeting test diagram of the complex TPA-Ir1 of the present invention;

[0037] Figure 6 Figure 1 is a cell cycle test diagram of the complex TPA-Ir1 of the present invention, in which (a) a cell cycle detection diagram of A549 cells treated with different concentrations of the complex TPA-Ir1 for 24 hours; (b) a statistical diagram of cell cycle arrest induced by the complex TPA-Ir1;

[0038] Figure 7 This is a study on the effect of the complex TPA-Ir1 of the present invention on reducing mitochondrial membrane potential. In the figure, (a) a graph showing changes in mitochondrial membrane potential after 24 hours of treatment with different concentrations of the complex TPA-Ir1 in A549 cells; (b) a statistical graph showing changes in mitochondrial membrane potential after 24 hours of treatment with different concentrations of the complex TPA-Ir1 in A549 cells;

[0039] Figure 8 This is a study on the production of reactive oxygen species in cells induced by the complex TPA-Ir1 of the present invention. In the figure, (a) a graph showing the changes in reactive oxygen species content in A549 cells after 24 hours of treatment with different concentrations of the complex TPA-Ir1; (b) a statistical graph showing the production of reactive oxygen species in A549 cells induced by the complex TPA-Ir1;

[0040] Figure 9 This is a study on the apoptosis induced by the complex TPA-Ir1 of the present invention;

[0041] Figure 10 This is a study on the inhibition of cell migration by the complex TPA-Ir1 of the present invention. In the figure, (a) scratch healing image of A549 cells after 24 hours of treatment with different concentrations of complex TPA-Ir1; (b) statistical graph of scratch healing after 24 hours of treatment with complex TPA-Ir1 on A549 cells. DETAILED DESCRIPTION

[0042] The present invention is further illustrated with reference to the following examples of some representative compounds, but these illustrations are not intended to limit the present invention.

[0043] The starting compounds used in the synthesis of the compounds are commercial products or can be prepared by known synthetic methods. The preparation methods of all organic compounds are available from the literature.

[0044] Example 1

[0045] (1) The structural formula of the ligand used in the present invention is:

[0046] .

[0047] The synthesis process is as follows:

[0048] Weigh 62.7 mg of 4-aminotriphenylamine and 41.7 mg of 8-hydroxyquinoline-2-carboxaldehyde into an eggplant-shaped flask, add 30 mL of methanol to dissolve, add two drops of formic acid, and stir at 65°C for 4-6 h. Remove the solvent under reduced pressure, and vacuum filter and dry to obtain 67.3 mg of a brown-black solid powder, which is the triphenylamine-modified ligand.

[0049] The synthesis process of triphenylamine-modified ligands is as follows:

[0050]

[0051] (2) The structural formula of the metal iridium dimer used in the present invention is:

[0052]

[0053] The synthesis process is as follows:

[0054] (1) Synthesis of half-sandwich metal iridium dimer (Dimer 1)

[0055] ① Weigh 0.5 g of hydrated iridium trichloride into a clean, dry microwave digestion vessel. Add 0.75 mL of 1,2,3,4,5-pentamethylcyclopentadiene and 20 mL of anhydrous methanol as the reaction solvent. Mix the above ingredients thoroughly, then fill the microwave digestion vessel with nitrogen and place it in the microwave digester.

[0056] ② After digestion, pour the supernatant into a clean beaker. Rinse the digestion tank with ice-cold methanol and pour the solution into the beaker. Add 10 mL of dichloromethane to the digestion tank to dissolve the remaining crystals. Then filter to remove the remaining iridium trichloride. Spin the solution to dryness to obtain the product.

[0057] ③ The solution in the beaker was spin-dried and washed with ice methanol. Dichloromethane was added to dissolve it, and then the remaining iridium trichloride was filtered out. 16 mL of a 1:1 mixture of n-hexane and anhydrous ether was added to the filtrate. The mixture was placed in a refrigerator for crystallization to obtain a pure half-sandwich metal iridium dimer (Dimer 1). The product was 0.41 g (yield: 66.7%). 1 H NMR (500 MHz, CDCl3): 1.60 ppm (s, J = 1.4 Hz, 15H), details as follows:

[0058] Table 1 Synthesis procedure

[0059]

[0060] Synthesis flow chart of half-sandwich metal iridium dimer (Dimer 1):

[0061]

[0062] (2) Synthesis of cyclometallated iridium dimer (Dimer 2)

[0063] ① Take a clean and dry Shrek bottle, add 0.63 g of trichlorohydrate, seal it, fill it with nitrogen, and inject 0.68 g of 2-phenylpyridine and 30 mL of a mixed solution of ethylene glycol monoethyl ether and ultrapure water in a ratio of 3:1 into the Shrek bottle using a syringe. Mix well and heat under reflux at 110 °C for 24 h.

[0064] ② The solution in the bottle initially appears dark yellow with a black suspension of hydrated iridium trichloride. The solution then turns orange-yellow and a precipitate forms. The orange-yellow suspension is filtered through a Büchner funnel, and the filter cake is washed several times with ethanol and acetone, dried, and stored. The filtrate is placed in the refrigerator for recrystallization (a small amount of product will precipitate, which requires repeated washing). A light yellow solid powder is obtained. Using a 10:1 dichloromethane:methanol solution as a developing solvent, a plate is formed (to test the purity of the crystals and the filter cake). The powder is then combined with the filter cake, dried, and stored to yield 0.74 g of pure base metal iridium dimer product (yield: 69%). The details are as follows:

[0065] The synthesis process of cyclometallated iridium dimer (Dimer 2) is as follows:

[0066]

[0067] Example 2 TPA-Ir1

[0068] (1) Weigh 39.8 mg of iridium dimer 1 and 87.3 mg of ligand (pre-dissolved in benzene at a concentration of 1.7 mg / mL) and add them to a clean and dry Shrek bottle. Add 25 mL of 0.4 mol / L sodium acetate solution to the bottle, evacuate the bottle, fill it with N2, and inject 25 mL of anhydrous methanol as the solvent. Mix the solution and stir at room temperature for 6 h, then reflux at 65 °C for 6 h. Detect the reaction by thin layer chromatography.

[0069] (2) After the reaction is completed, the flask is connected to a rotary evaporator and the solvent is removed by vacuum rotary evaporation. Dichloromethane is added to dissolve the precipitate at the bottom of the flask and filtered with a filter. N-hexane is added and a reddish-brown solid powder (TPA-Ir1) is obtained after the solution is completely evaporated.

[0070] The H NMR and mass spectra of TPA-Ir1 are as follows Figure 1 and Figure 2 shown.

[0071] Example 3 TPA-Ir3

[0072] (1) Weigh 40.2 mg of iridium dimer 2 and 88.1 mg of ligand (pre-dissolved in benzene at a concentration of 1.7 mg / mL) into a clean and dry Shrek bottle. Add 25 mL of 0.4 mol / L sodium acetate solution to the bottle. After evacuating the bottle and filling it with N2, inject 25 mL of anhydrous methanol as the solvent. Mix the solution and stir the reaction at room temperature for 6 h, then reflux at 65 °C for 6 h. Detect the reaction by thin layer chromatography.

[0073] (2) After the reaction is completed, the flask is connected to a rotary evaporator and the solvent is removed by vacuum rotary evaporation. Dichloromethane is added to dissolve the precipitate at the bottom of the flask and filtered with a filter. N-hexane is added and a brown-black solid powder (TPA-Ir2) is obtained after the solution is completely evaporated.

[0074] The H NMR and mass spectra of TPA-Ir2 are as follows Figure 3 and Figure 4 shown.

[0075] Effect embodiment

[0076] (I) Experiment on the inhibition of cancer cell proliferation by organometallic iridium complexes:

[0077] (1) Preparation of the complex to be tested: Weigh the prepared complex and dissolve it in 600 μL DMSO to a drug concentration of 10 mM as a stock solution. The stock solution is then diluted with DMEM to different concentrations.

[0078] (2) Cell growth inhibition assay (MTT assay):

[0079] 1) Add different concentrations of drugs to the culture medium of cells in the logarithmic growth phase and incubate them. Add 5µL to each well. Set up 4 parallel experiments for each concentration.

[0080] 2) After 24 hours of incubation, add 15 µL of MTT solution (5 mg / mL) to each well. After 4 hours of incubation in the dark, discard the culture medium and add 100 µL of DMSO solution to each well. Vortex for 2 minutes and measure the absorbance at 570 nm using a microplate reader.

[0081] 3) The cell survival curves at different concentrations were fitted using Origin software (V 2021) to obtain the half-lethal concentration (IC 50 ).

[0082] The MTT assay was used to detect the in vitro proliferation of A549 cells, A549-DDP (human lung adenocarcinoma cisplatin-resistant cells) cells, and Base-2B cells after 24 h of treatment with these two complexes. The IC values ​​of TPA-Ir1 and TPA-Ir2 were calculated. 50The results are shown in Table 2.

[0083] Table 2 IC values ​​of complexes in different cells after 24h treatment 50

[0084]

[0085] As shown in Table 2, although the TPA-Ir2 complex with iridium ring structure showed certain antiproliferative activity against A549 cells in vitro (IC 50 =56.4±5.1 μM), but compared with them, the TPA-Ir1 complex with a half-sandwich iridium structure had a better in vitro antiproliferative activity against A549 cells (IC 50 =19.1±1.3 μM), even compared with cisplatin (IC 50 =21.3±1.7 μM).

[0086] (II) Use two-photon laser confocal microscopy to visually detect the targeting of target complexes after they enter cells

[0087] A549 cells were pretreated at 37°C, CCCP, CQ, and 4°C for 1 h, and then 100 μL of 1.0×IC 50 The cells were co-incubated with TPA-Ir1 for 1 h, and the fluorescence intensity of the different treatment groups was detected by laser confocal microscopy. Compared with the control group pretreated at 37°C, the fluorescence intensity in A549 cells pretreated with CCCP or 4°C was weaker, while the fluorescence intensity in A549 cells pretreated with CQ was not much different from that in the control group. This indicates that there is more TPA-Ir1 in the cells of the 37°C group and the CQ group, but less in the CCCP group and the 4°C group, that is, the complex TPA-Ir1 enters the A549 cells through an energy-dependent pathway.

[0088] A549 cells were incubated with DAPI, LTDR and MTDR probes and 100 μL 1.0×IC 50 The co-localization coefficients of different treatment groups were detected by laser confocal microscopy. Figure 5 As shown, the colocalization coefficient of the complex TPA-Ir1 with the cell nucleus is 0, that is, the complex TPA-Ir1 basically does not enter the cell nucleus; the colocalization coefficient with the mitochondria is 0.82, and the colocalization coefficient with the lysosome is 0.25, that is, the main target organelle of the complex TPA-Ir1 entering A549 cells is the mitochondria.

[0089] (III) Cell cycle testing of complexes

[0090] A549 cells were seeded in 6-well plates and cultured to the logarithmic growth phase.50 and 1.00×IC 50 ) and incubate with drugs for 24 h, then collect the cells. Add 1 mL of 70% ice ethanol solution to a new centrifuge tube, resuspend the cell pellet with 50 µL of PBS, slowly inject it into ethanol, shake to mix, and fix it at -20 °C overnight. After fixation, centrifuge and discard the supernatant, wash twice with PBS, resuspend with 500 µL PBS, add RNase (2.5 µL), mix well, add PI (25 µL), and mix again. Incubate in a 37 °C water bath in the dark for 30 min. After incubation, keep it in a dark ice bath and wait for detection by flow cytometry. As the drug concentration increases, more and more cells are blocked in the S phase, as shown in the following figure. Figure 6 shown.

[0091] (IV) Mitochondrial membrane potential level detection

[0092] A549 cells were seeded in 6-well plates and cultured until the logarithmic growth phase. Different concentrations of drugs (0.5×IC50, 1.0×IC50, 1.5×IC50, and 2.0×IC50) were added and incubated for 24 hours before cell collection. A positive control group was pretreated with CCCP (2 µL, 5 µM) 2 hours before cell collection. 1 mL of JC-1 staining working solution was added to each well, mixed, and incubated at 37°C in a dark-proof water bath for 20 minutes. After incubation, the cells were centrifuged at 1000 rpm for 5 minutes, the supernatant discarded, and the cells were washed twice with 1 mL of JC-1 staining buffer. The cells were resuspended in 0.5 mL of JC-1 staining buffer and kept on ice in the dark until analysis by flow cytometry. The results were analyzed using FlowJo software (V10).

[0093] from Figure 7 It can be seen that with the increase of drug concentration, the green fluorescence in mitochondria gradually increases, that is, the mitochondrial membrane potential gradually decreases, thereby affecting the normal metabolism of cells.

[0094] (V) Determination of intracellular reactive oxygen species content

[0095] A549 cells were seeded in 6-well plates and cultured to the logarithmic growth phase. Different concentrations (0.5×IC50, 1.0×IC 50 , 1.5×IC 50 and 2.0×IC 50) for 24 hours. For the positive control group, pretreatment with 2 µL of R-Rosup (1:1000 dilution) was added 1-2 hours before cell collection. Cells were trypsinized and harvested, and the supernatant was discarded by centrifugation. Cells were washed twice with 1 mL of serum-free DMEM (high-glucose medium) and centrifuged. The supernatant was discarded and resuspended in 0.5 mL of probe solution (DCFH-DA probe: serum-free DMEM = 1:1000) and placed in a 37°C water bath for 20 minutes. At the end of the incubation period, the cells were centrifuged and the supernatant discarded. Cells were washed three times with 1 mL of serum-free DMEM and resuspended in 0.5 mL of serum-free DMEM. The cells were kept on ice until flow cytometry analysis was performed. The cells were protected from light throughout the experiment. Results were analyzed using FlowJo software (V10).

[0096] like Figure 8 As shown, as the concentration of the complex TPA-Ir1 increases, the content of intracellular reactive oxygen species also increases continuously, which indicates that the complex TPA-Ir1 exerts its anti-cancer activity by inducing the transitional production of ROS.

[0097] (VI) Study on the apoptosis induced by the complex TPA-Ir1

[0098] A549 cells were seeded into 6-well plates and cultured in a CO2 incubator until the logarithmic growth phase. 50 , 1.0×IC 50 and 1.5×IC 50 After incubation for 24 hours with 100 µL of the drug, cells were trypsinized and harvested. Resuspend the cells in 195 µL of Annexin V-FITC buffer, add 5 µL of Annexin V-FITC and 10 µL of propidium iodide (PI), mix well, and incubate at 37°C in the dark for 10–20 minutes. Place on ice in the dark until flow cytometry is performed and analysis is performed using FlowJo software (V10).

[0099] from Figure 9 As can be seen from the results, the complex TPA-Ir1 can effectively induce apoptosis in A549 cells. In particular, when the concentration of the complex TPA-Ir1 is 1.5×IC50, the apoptosis rate of A549 cells exceeds 36%, and the apoptosis is mainly in the late stage. Therefore, the complex TPA-Ir1 can induce apoptosis in A549 cells, and the increase in a dose-dependent manner.

[0100] (VII) Cell scratch test

[0101] A549 cells seeded in a 6-well plate were allowed to adhere for 4-6 hours. After the culture medium was discarded and the cells were washed once with 1 mL of PBS, 2 mL of PBS was added to each well. A 10 µL pipette tip was used to make a fine, straight scratch perpendicular to the bottom of the 6-well plate (using the 6-well plate lid for assistance). Floating cells were washed with PBS, fresh PBS was added, and the cells were photographed. The position and scratch spacing were recorded for each image. After photography, the PBS was discarded and 2 mL of fresh culture medium containing a specific drug concentration was added. After returning the cells to the incubator and continuing to culture for 12 hours, the culture medium was discarded and the cells were washed once with 1 mL of PBS. After adding 2 mL of PBS to each well, images were acquired at the same location, and the scratch spacing was recorded for each image.

[0102] from Figure 10 It can be seen that the complex TPA-Ir1 can effectively inhibit the migration of A549 cells. The migration rate of the control group is 39.57%, and the concentration of the complex TPA-Ir1 is 0.5×IC 50 and 1.0×IC 50 When , the migration rates of A549 cells were 15.91% and 4.82%, respectively.

Claims

1. A triphenylamine-modified iridium (III) complex, characterized in that: The metal iridium (III) complex is TPA-Ir1 or TPA-Ir2, and the structural formula is: 。 2. A method for preparing the metal iridium (III) complex according to claim 1, characterized in that: The following steps are involved: (1) Weigh the iridium dimer and ligand, add sodium acetate solution, evacuate the solution, fill it with nitrogen, and inject anhydrous methanol as solvent. Mix the solution and stir at room temperature to react. Then, heat it under reflux and detect the reaction by thin layer chromatography. (2) After the reaction is completed, the solvent is removed by rotary evaporation under reduced pressure, dichloromethane is added to dissolve the precipitate and the precipitate is filtered, and n-hexane is added to the precipitate. After the solution evaporates completely, a reddish-brown solid powder TPA-Ir1 or a brownish-black solid powder TPA-Ir2 is obtained.

3. The preparation method according to claim 2, characterized in that In step (1), the structural formula of the ligand is: 。 4. The preparation method according to claim 2, characterized in that In step (1), the structural formula of the metal iridium dimer is: 。 5. The preparation method according to claim 2, characterized in that In step (1), the mass ratio of the metal iridium dimer to the ligand is 26:57; the ratio of the metal iridium dimer to the sodium acetate solution is 0.030 g:15-20 mL.

6. The preparation method according to claim 5, characterized in that In step (1), the ligand is pre-dissolved in benzene at a concentration of 1.7 mg / mL; the concentration of the sodium acetate solution is 0.4 mol / L.

7. The preparation method according to any one of claims 2 to 6, characterized in that In step (1), the stirring reaction time is 6 hours; the heating reflux is reflux at 65°C for 6 hours.

8. Use of the triphenylamine-modified metal iridium (III) complex according to claim 1 in the preparation of anticancer drugs.

9. Use of the triphenylamine-modified iridium (III) complex according to claim 1 in detecting the number of cells at different stages for non-disease diagnosis and treatment purposes.

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