A binuclear ruthenium photocatalyst, a preparation method thereof and application thereof in photocatalytic anti-triple negative breast cancer

Abstract

The application discloses a binuclear ruthenium photocatalyst, a preparation method thereof and application of the binuclear ruthenium photocatalyst in photocatalytic anti-triple negative breast cancer, and a structural formula of the binuclear ruthenium photocatalyst is shown in the following formula: the binuclear ruthenium catalyst containing the structure of the application scheme has a strong photocatalytic effect on a triple negative breast cancer cell strain; under near-infrared light irradiation conditions, a mouse triple negative breast cancer cell strain has a strong growth and proliferation inhibition ability (IC 50 is 0.015 muM), and under dark conditions, the cytotoxicity is greater than 100 muM, and a photo treatment index PI is as high as 6666, which has important significance for research on metal drugs for anti-breast cancer, and is expected to be used for preparing near-infrared excitation anti-tumor photocatalytic drugs.

Description

Technical Field

[0001] This invention relates to the field of medicinal chemistry, and in particular to a binuclear ruthenium photocatalyst, its preparation method, and its application in photocatalytic anti-triple-negative breast cancer. Background Technology

[0002] Breast cancer is a common malignant tumor in women. Triple-negative breast cancer accounts for a large proportion of breast cancers, and it is highly invasive, prone to metastasis, and has an extremely poor prognosis, presenting many challenges in its treatment. Treatment methods for breast cancer include surgery, radiotherapy and chemotherapy, endocrine therapy, and targeted therapy. Because triple-negative breast cancer lacks expression of estrogen receptor (ER), progesterone receptor (PR), and human epidermal factor receptor 2 (Her-2), there are very few targeted drugs available for it. Endocrine therapy and Her-2-targeted therapy are largely ineffective against this type of cancer. Although triple-negative breast cancer is relatively sensitive to chemotherapy, it usually responds well to treatment. Therefore, developing more treatment methods and applying them clinically as early as possible will give patients with triple-negative breast cancer more hope.

[0003] Photocatalysis is a non-invasive / minimally invasive cancer treatment method. It's a relatively gentle approach that delivers light to specific lesion areas with minimal damage to healthy tissue. Photocatalysis is also easier to design to meet specific patient needs, aligning with the requirements of precision medicine. Therapies based on photocatalytic materials have become a new trend in cancer treatment research in recent years, and some photosensitizing drugs have begun to be used in clinical treatment. Photocatalysis targets the tumor microenvironment, inputting photon energy to trigger a photocatalytic reaction that disrupts the redox balance in the tumor region, delivering a fatal blow to tumor cells.

[0004] However, there are relatively few drugs currently available that are effective in photocatalytic therapy for triple-negative breast cancer, and further development is urgently needed. Summary of the Invention

[0005] This invention aims to at least solve one of the technical problems existing in the prior art. To this end, this invention proposes a binuclear ruthenium photocatalyst, which shows promising application prospects in the treatment of triple-negative breast cancer.

[0006] The present invention also proposes a method for preparing the above-mentioned binuclear ruthenium photocatalyst.

[0007] This invention also proposes the application of the aforementioned binuclear ruthenium photocatalyst.

[0008] According to one aspect of the present invention, a binuclear ruthenium photocatalyst is provided, the structural formula of which is shown below:

[0009]

[0010] According to a preferred embodiment of the present invention, at least the following beneficial effects are achieved: the binuclear ruthenium catalyst containing the structure of the present invention exhibits strong photocatalytic effects in triple-negative breast cancer cell lines; under near-infrared light irradiation, mouse triple-negative breast cancer cell lines demonstrate strong growth and proliferation inhibition ability (IC50). 50 The concentration was 0.015 μM, while under dark conditions, its cytotoxicity was >100 μM, and the phototherapy index (PI) was as high as 6666. This is of great significance for the research of metal drugs for anti-breast cancer and is expected to be used to prepare near-infrared excited anti-tumor photocatalytic drugs.

[0011] According to another aspect of the present invention, a method for preparing the above-mentioned catalyst is provided, comprising the following steps:

[0012] S1. 4'-Bromo-2,2':6',2”-terpyridine is reacted with ruthenium(III) salt to generate a precursor compound;

[0013] S2. The precursor compound is reacted with 2,6-bis(quinolin-8-yl)pyridine, and after conversion with hexafluorophosphate ions, a ruthenium complex is generated;

[0014] S3. The ruthenium complex is reacted with 1,3-bis(2-ethylhexyl)-5,7-bis(5-(trimethyltinyl)thiophen-2-yl)-4H,8H-benzo[1,2-c:4,5-c']dithiophen-4,8-dione to obtain the product.

[0015] The preparation method according to a preferred embodiment of the present invention has at least the following beneficial effects: the preparation process of the present invention is simple, easy to operate, and has good prospects for industrial application.

[0016] In some embodiments of the present invention, the reaction conditions of step S1 include at least one of the following conditions:

[0017] (1) The reaction is carried out in an alcohol solvent system; preferably a lower alcohol, such as a C1 to C6 alcohol;

[0018] (2) The reaction temperature is 75-95℃; preferably 80-90℃; more preferably 85℃;

[0019] (3) The reaction time is 8-16 h; preferably 10-14 h; more preferably 12 h;

[0020] (4) The molar ratio of 4'-bromo-2,2':6',2”-terpyridine to ruthenium(III) salt is 1:1-1.2.

[0021] In some embodiments of the present invention, the reaction conditions of step S2 include at least one of the following conditions:

[0022] (1) The reaction is carried out in an alcohol solvent system; preferably, the alcohol solvent is ethylene glycol;

[0023] (2) The reaction temperature is 180-220℃; preferably 190-210℃; more preferably 200℃;

[0024] (3) The reaction time is 3-6 hours; preferably 3-5 hours; more preferably 4 hours;

[0025] (4) The molar ratio of the precursor compound to 2,6-bis(quinolin-8-yl)pyridine is 1:0.8-1.2.

[0026] In some embodiments of the present invention, the reaction conditions of step S3 include at least one of the following conditions:

[0027] (1) The reaction is carried out under a protective atmosphere;

[0028] (2) The reaction is carried out in a mixture of toluene and N,N-dimethylformamide; preferably, the volume ratio of toluene to N,N-dimethylformamide is 1:1;

[0029] (3) The reaction temperature is 100-135℃; preferably 110-120℃; more preferably 115℃;

[0030] (4) The reaction time is 18-24 h; preferably 18-22 h; more preferably 20 h;

[0031] (5) The molar ratio of the ruthenium complex to 1,3-bis(2-ethylhexyl)-5,7-bis(5-(trimethyltinyl)thiophen-2-yl)-4H,8H-benzo[1,2-c:4,5-c']dithiophen-4,8-dione is 1:(1.8-2.2); preferably, the molar ratio of the ruthenium complex to 1,3-bis(2-ethylhexyl)-5,7-bis(5-(trimethyltinyl)thiophen-2-yl)-4H,8H-benzo[1,2-c:4,5-c']dithiophen-4,8-dione is 1:1.9-2.1;

[0032] (6) The reaction is carried out under the catalysis of a catalyst, which includes tetra(triphenylphosphine)palladium.

[0033] According to another aspect of the present invention, the use of the above-described catalyst in the preparation of anti-triple-negative breast cancer drugs is proposed.

[0034] The application of a preferred embodiment of the present invention has at least the following beneficial effects: the present invention has good application prospects in the field of preparation of anti-triple-negative breast cancer drugs.

[0035] In some embodiments of the present invention, the anti-triple-negative breast cancer drug is a near-infrared photocatalytically activated antitumor drug.

[0036] According to another aspect of the present invention, an anti-triple-negative breast cancer drug is provided, wherein the active ingredient of the drug comprises the aforementioned binuclear ruthenium photocatalyst.

[0037] In some embodiments of the present invention, the anti-triple-negative breast cancer drug is an anti-mouse triple-negative breast cancer drug.

[0038] According to another aspect of the present invention, a near-infrared light-excited antitumor drug is provided, wherein the active ingredient of the drug comprises the aforementioned binuclear ruthenium photocatalyst.

[0039] According to another aspect of the present invention, an antitumor metal photosensitizer is provided, wherein the active ingredient of the antitumor metal photosensitizer comprises the above-mentioned binuclear ruthenium photocatalyst.

[0040] Other features and advantages of the invention will be set forth in the description which follows, and will be apparent in part from the description, or may be learned by practicing the invention. Attached Figure Description

[0041] The above and / or additional aspects and advantages of the present invention will become apparent and readily understood from the description of the embodiments taken in conjunction with the following drawings, in which:

[0042] Figure 1 The ultraviolet absorption spectrum of the binuclear ruthenium photocatalyst prepared in the embodiments of the present invention;

[0043] Figure 2 The figure shows the experimental results of the ability of the binuclear ruthenium photocatalyst prepared in the embodiments of the present invention to generate singlet oxygen.

[0044] Figure 3 The figure shows the experimental results of the photocatalytic oxidation of NADH by the dual-nuclear ruthenium photocatalyst prepared in the embodiments of the present invention.

[0045] Figure 4 The figure shows the results of dark toxicity and phototoxicity tests of the binuclear ruthenium photocatalyst prepared in the embodiments of the present invention against mouse triple-negative breast cancer cells (4T1) under near-infrared excitation. Detailed Implementation

[0046] The following will clearly and completely describe the concept and technical effects of the present invention in conjunction with embodiments, so as to fully understand the purpose, features and effects of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, not all of them. Other embodiments obtained by those skilled in the art based on the embodiments of the present invention without creative effort are all within the scope of protection of the present invention. Unless otherwise specified, the experimental methods used in the embodiments are conventional methods; the materials and reagents used, unless otherwise specified, are commercially available. Unless otherwise specified, the same parameter value is the same in all embodiments. The embodiments described below are exemplary and are only used to explain the present invention, and should not be construed as limiting the present invention.

[0047] The term "room temperature" as used in this invention refers to any temperature between 25 and 5°C, and specifically 25°C in the embodiments.

[0048] Example

[0049] This embodiment prepares a dual-core ruthenium photocatalyst, the structural formula of which is as follows:

[0050]

[0051] The specific process is as follows:

[0052] (1) Ru(tpy-Br)Cl3 is generated by the reaction of 4'-bromo-2,2':6',2”-terpyridine with ruthenium(III) trichloride hydrate.

[0053] 4'-bromo-2,2':6',2”-terpyridine (312 mg, 1 mmol) and ruthenium(III) trichloride hydrate (225 mg, 1.1 mmol) were dissolved in 20 mL of ethanol solution. The mixture was refluxed at 85 °C for 12 h and then cooled to room temperature. The reaction solution was filtered, and the filter cake was washed with ethanol and n-hexane and then dried under vacuum to obtain a brown solid powder Ru(tpy-Br)Cl3.

[0054] The chemical reaction equations for the above reactions are shown below:

[0055]

[0056] (2) Ru(tpy-Br)Cl3 reacts with 2,6-bis(quinolin-8-yl)pyridine to generate [Ru(dqp)(tpy-Br)](PF6)2

[0057] The precursor Ru(tpy-Br)Cl3 (260 mg, 0.5 mmol) and 2,6-bis(quinolin-8-yl)pyridine (167 mg, 0.5 mmol) were dissolved in 20 mL of ethylene glycol solution. After stirring at 200 °C for 4 h, the mixture was cooled to room temperature, and a saturated NH4PF6 aqueous solution was added. After stirring at room temperature for 1 h, the mixture was filtered, and the filter cake was washed with water and ethanol and dried under vacuum to obtain the ruthenium complex [Ru(bnp)(tpy-Br)](PF6)2 purple powder.

[0058] The chemical reaction equations for the above reactions are shown below:

[0059]

[0060] (3) The reaction of [Ru(bnp)(tpy-Br)](PF6)2 with 1,3-bis(2-ethylhexyl)-5,7-bis(5-(trimethyltinyl)thiophen-2-yl)-4H,8H-benzo[1,2-c:4,5-c']dithiophene-4,8-dione produces a binuclear ruthenium photocatalyst.

[0061] [Ru(bnp)(tpy-Br)](PF6)2 (124.63 mg, 0.12 mmol), 1,3-bis(2-ethylhexyl)-5,7-bis(5-(trimethyltinyl)thiophen-2-yl)-4H,8H-benzo[1,2-c:4,5-c']dithiophene-4,8-dione (46.7 mg, 0.05 mmol), and tetra(triphenylphosphine)palladium (6 mg, 0.005 mmol) were dissolved in 12 mL of toluene / N,N-dimethylformamide (V / V = 1:1). The mixture was stirred at 115 °C for 20 h under argon protection. After the reaction was completed, the mixture was cooled to room temperature, saturated brine was added, the precipitate was collected by filtration, washed with water and toluene, and dried under vacuum to obtain a blue solid powder.

[0062] The chemical reaction equations for the above reactions are shown below:

[0063]

[0064] The mass spectrum of the product is: ESI-MS [CH3OH, m / z]: 486 [M-4PF6] - ] 4+ ;

[0065] The 1H NMR spectrum of the product is as follows: 1H NMR(500MHz,DMSO-d6)δ9.50(d,J=7.4Hz,4H),9.40(s,3H),9.13(d,J=7.8Hz,4H),8. 87(d,J=6.9Hz,4H),8.77–8.71(m,6H),8.63(s,2H),8.44(d,J=6.9Hz,4H),8.31(d,J= 22.0Hz,6H),7.87(s,5H),7.56(s,3H),7.41(s,4H),7.11(s,5H),3.50(s,4H),1.85(s ,1H),1.39(s,12H),1.26(s,6H),0.96(s,5H),0.90(s,1H),0.76(s,4H),0.67(s,1H).

[0066] Application examples

[0067] The performance of the binuclear ruthenium photocatalyst prepared in the examples was tested, as follows:

[0068] 1. Absorption spectroscopy determination of near-infrared binuclear ruthenium photocatalyst

[0069] Using anhydrous ethanol (CH3OH) as a solvent, a 10 μM sample solution of the binuclear ruthenium photocatalyst from the examples was prepared. The ultraviolet absorption spectrum of the binuclear ruthenium photocatalyst was then recorded using a double-beam UV-Vis spectrophotometer. The results are as follows: Figure 1 As shown. Figure 1 The figure represents the absorbance of the catalyst in ethanol. As can be seen from the figure, it has good light absorption capacity in both organic and aqueous solvents.

[0070] 2. Determination of the ability of binuclear ruthenium complexes to generate singlet oxygen

[0071] To detect the photocatalytic ability of the binuclear ruthenium complex synthesized in the examples to generate singlet oxygen, the singlet oxygen probe 9,10-anthrayl-bis(methylene)dimalonic acid (ABDA) was used to determine the ability of the binuclear ruthenium complex to generate singlet oxygen. When singlet oxygen is generated in the solution, ABDA immediately captures the singlet oxygen in the solution and reacts to generate an endogenous oxidation product, causing the characteristic absorption peak of ABDA to decrease. The rate of decrease of the ABDA absorption peak is the singlet oxygen generation rate. Therefore, the singlet oxygen generation ability can be reflected by monitoring the changes in the UV-Vis absorption spectra of the test sample and the ABDA mixture solution under different illumination times using a UV-Vis spectrophotometer.

[0072] Two aqueous solutions containing the same binuclear ruthenium complex (5 μM) and ABDA reagent (200 μM) were placed in cuvettes, and their singlet oxygen generation capacity under 635 nm illumination was measured. The results are as follows: Figure 2As shown. From Figure 2 As can be seen from the data, this binuclear ruthenium complex has the ability to generate singlet oxygen after being exposed to light.

[0073] 3. Determination of the photocatalytic oxidation ability of binuclear ruthenium complexes for NADH

[0074] Because under light irradiation, metal complexes can oxidize reduced coenzyme I (NADH) to its oxidized form NAD. ++ Therefore, the ruthenium-containing complex (5 μM) and NADH (A 339nm =1.0) mixed in a cuvette, its ability to oxidize NADH under 635nm light irradiation can be measured, and the results are as follows. Figure 3 As shown. From Figure 3 As can be seen, ruthenium complexes have significant photocatalytic oxidation capabilities for NADH.

[0075] 4. Photodynamic therapy effect of dual-nuclear ruthenium photocatalyst on mouse triple-negative breast cancer cell line

[0076] Resazurin solution is blue and is commonly used as an acid-base indicator (orange to deep purple at pH 3.8) and a redox indicator. In cell viability assays, resazurin can penetrate cells and be irreversibly reduced to pink by living cells, while resorufin, a red fluorescent reagent, appears. The absorbance or fluorescence intensity of resorufin is positively correlated with cell number and reducing capacity; therefore, cell proliferation can be analyzed using an enzyme-linked immunofluorescence assay (ELISA).

[0077] The experimental steps for the azure blade are as follows:

[0078] (1) First, revive one tube of 4T1 tumor cells (commercially available), and culture them in fresh complete culture medium (DMEM medium + 10 vol% fetal bovine serum + 1 vol% penicillin-streptomycin mixture, the fetal bovine serum and penicillin-streptomycin mixture were commercially available). After passage 2 times, start the experiment.

[0079] (2) When the cells reach the logarithmic growth phase, seed them into two 96-well plates at a density of 5000 cells / well (each well is cultured with 100 μL of culture medium, one plate is the light group and the other is the dark control group), and incubate them in a 37°C, 5 vol% CO2 incubator.

[0080] (3) After the culture medium adheres to the wall, remove the original culture medium and add 100 μL of binuclear ruthenium photocatalyst at seven concentrations of 100, 50, 10, 1, 0.1, 0.01 and 0.001 mM to each well. Shake gently and incubate in a carbon dioxide incubator (37℃, 5 vol% CO2) in the dark.

[0081] (4) After incubation for 6 hours, the cell culture plates of the light-illuminated group were placed under a 635nm light source for 45 minutes (light dose of 63.7 J / cm²). 2 Then, the cells were returned to the incubator and incubated in the dark for another 42 hours (the cells in the dark control group were kept in the incubator in the dark throughout the incubation).

[0082] (5) After incubation for 40 h, discard the culture medium from each well, then add 80 μL of resazurin (100 mg / mL) to each well, and continue incubation at 37℃ for 4 h. Then, use the fluorescence plate of an ELISA reader to detect EX540 / EM590, calculate the cell proliferation inhibition rate, and determine the IC50. 50 Value (drug concentration when the inhibition rate is equal to 50%).

[0083] Figure 4 This study investigated the cytotoxic effects of different concentrations of binuclear ruthenium photocatalysts on mouse triple-negative breast cancer cell line (4T1 cells) under both dark and light-treated conditions (near-infrared light) using the resazurite assay. The figure shows that, under dark conditions, the IC50 value for the cytotoxic effect on mouse triple-negative breast cancer cell line (4T1 cells) was significantly lower. 50 >100 μM, IC50 against cisplatin-resistant human non-small cell lung cancer cell lines under light conditions 50 The concentration was 0.015 μM, and the phototherapy index (PI) was as high as 6666, indicating that the dual-core ruthenium photocatalyst of the present invention has a strong photodynamic therapy effect.

[0084] In summary, the dual-nuclear ruthenium photocatalyst provided by this invention exhibits a strong photocatalytic effect on the mouse triple-negative breast cancer cell line (4T1 cells). Under illumination (near-infrared light), it strongly inhibits the growth and proliferation of the mouse triple-negative breast cancer cell line (4T1 cells) (IC50). 50 The concentration was 0.015 μM, while under dark conditions, its cytotoxicity was >100 μM, and the phototherapy index (PI) was as high as 6666. This indicates that the present invention has important significance for the preparation of metal drugs for near-infrared induced anti-drug-resistant tumors.

[0085] The embodiments of the present invention have been described in detail above, but the present invention is not limited to the above embodiments. Within the scope of knowledge possessed by those skilled in the art, various changes can be made without departing from the spirit of the present invention.

Claims

1. A dual-nuclear ruthenium photocatalyst, characterized in that: The structural formula of the dual-nuclear ruthenium photocatalyst is shown below:

2. The method for preparing the binuclear ruthenium photocatalyst according to claim 1, characterized in that: Includes the following steps: S1. 4'-Bromo-2,2':6',2”-terpyridine is reacted with ruthenium(III) salt to generate a precursor compound; S2. The precursor compound is reacted with 2,6-bis(quinolin-8-yl)pyridine, and after conversion with hexafluorophosphate ions, a ruthenium complex is generated; S3. The ruthenium complex is reacted with 1,3-bis(2-ethylhexyl)-5,7-bis(5-(trimethyltinyl)thiophen-2-yl)-4H,8H-benzo[1,2-c:4,5-c']dithiophen-4,8-dione to obtain the product.

3. The method for preparing the binuclear ruthenium photocatalyst according to claim 2, characterized in that: The reaction conditions for step S1 include at least one of the following conditions: (1) The reaction is carried out in an alcohol solvent system; (2) The reaction temperature is 75-95℃; (3) The reaction time is 8-16 hours; (4) The molar ratio of 4'-bromo-2,2':6',2”-terpyridine to ruthenium(III) salt is 1:1-1.

2.

4. The method for preparing the binuclear ruthenium photocatalyst according to claim 2, characterized in that: The reaction conditions for step S1 include at least one of the following conditions: 1) The reaction temperature is 80-90℃; 2) The reaction time is 10-14 hours.

5. The method for preparing the binuclear ruthenium photocatalyst according to claim 2, characterized in that: The reaction conditions for step S1 include at least one of the following conditions: 1) The reaction temperature is 85℃; 2) The reaction time is 12 hours.

6. The method for preparing the binuclear ruthenium photocatalyst according to claim 2, characterized in that: The reaction conditions for step S2 include at least one of the following conditions: (1) The reaction is carried out in an alcohol solvent system; (2) The reaction temperature is 180-220℃; (3) The reaction time is 3-6 hours; (4) The molar ratio of the precursor compound to 2,6-bis(quinolin-8-yl)pyridine is 1:0.8-1.

2.

7. The method for preparing the binuclear ruthenium photocatalyst according to claim 6, characterized in that: The alcohol solvent is ethylene glycol.

8. The method for preparing the binuclear ruthenium photocatalyst according to claim 6, characterized in that: The reaction conditions for step S2 include at least one of the following conditions: (1) The reaction temperature is 190-210℃; (2) The reaction time is 3-5 hours.

9. The method for preparing the binuclear ruthenium photocatalyst according to claim 6, characterized in that: The reaction conditions for step S2 include at least one of the following conditions: (1) The reaction temperature is 200℃; (2) The reaction time is 4 hours.

10. The method for preparing the binuclear ruthenium photocatalyst according to claim 2, characterized in that: The reaction conditions in step S3 include at least one of the following conditions: (1) The reaction is carried out under a protective atmosphere; (2) The reaction was carried out in a mixture of toluene and N,N-dimethylformamide; (3) Reaction temperature 100-135℃; (4) The reaction time is 18-24 hours; (5) The molar ratio of the ruthenium complex to 1,3-bis(2-ethylhexyl)-5,7-bis(5-(trimethyltinyl)thiophen-2-yl)-4H,8H-benzo[1,2-c:4,5-c']dithiophene-4,8-dione is 1:(1.8-2.2); (6) The reaction is carried out under the catalysis of a catalyst, which includes tetra(triphenylphosphine)palladium.

11. The method for preparing the binuclear ruthenium photocatalyst according to claim 10, characterized in that: The reaction conditions in step S3 include at least one of the following conditions: (1) The volume ratio of toluene to N,N-dimethylformamide is 1:1; (2) Reaction temperature 110-120℃; (3) The reaction time is 18-22 hours; (4) The molar ratio of the ruthenium complex to 1,3-bis(2-ethylhexyl)-5,7-bis(5-(trimethyltinyl)thiophen-2-yl)-4H,8H-benzo[1,2-c:4,5-c']dithiophene-4,8-dione is 1:1.9-2.

1.

12. The method for preparing the binuclear ruthenium photocatalyst according to claim 10, characterized in that: The reaction conditions in step S3 include at least one of the following conditions: (1) Reaction temperature 115℃; (2) The reaction time is 20h.

13. The application of the binuclear ruthenium photocatalyst according to claim 1 in the preparation of anti-triple-negative breast cancer drugs.

14. The application according to claim 13, characterized in that: The anti-triple-negative breast cancer drug is a near-infrared photocatalytically activated anti-tumor drug.

15. A drug for treating triple-negative breast cancer, characterized in that: The active ingredient of the drug comprises the binuclear ruthenium photocatalyst as described in claim 1.

16. The anti-triple-negative breast cancer drug according to claim 15, characterized in that: The anti-triple-negative breast cancer drug is an anti-mouse triple-negative breast cancer drug.

17. A near-infrared light-excited antitumor drug, characterized in that: The active ingredient of the drug comprises the binuclear ruthenium photocatalyst as described in claim 1.

18. An antitumor metal photosensitizer, characterized in that: The active ingredient of the antitumor metal photosensitizer includes the binuclear ruthenium photocatalyst as described in claim 1.

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