Highly conjugated photosensitizer, its preparation method and application in photodynamic therapy

Abstract

The application discloses a high-conjugated photosensitizer with high ROS generation capacity and a preparation method thereof. The photosensitizer is prepared from halogenated BOPYIN as raw material, and is coupled with 4-diphenylaminophenylboronic acid under the catalysis of tetrakis(triphenylphosphine)palladium(0) and K2CO3 under the protection of N2. The synthesis method is simple, separation and purification are convenient, and the yield is high. An aromatic ring is introduced on the parent structure, so that the absorption spectrum is red-shifted and has strong stability. The compound has long-wavelength absorption characteristics due to the extended conjugated structure, and the optical characteristics enable the compound to be effectively applied in the field of photodynamic therapy.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of fine chemicals, and more particularly, to a high conjugated photosensitizer with high ROS generation capacity and a preparation method thereof. BACKGROUND

[0002] Photodynamic therapy (PDT) as a new tumor treatment method, its treatment effect is highly dependent on the performance of photosensitizer. The ideal photosensitizer should have high active oxygen (ROS) generation capacity, suitable light absorption characteristics and good biocompatibility. However, the existing photosensitizer still faces many challenges in clinical application. Although traditional porphyrin and phthalocyanine photosensitizers are widely studied, due to their inherent molecular structure limitations, they often have problems such as insufficient ROS yield and poor light stability. The metal complex photosensitizer developed in recent years has improved the ROS yield to some extent, but it introduces potential metal toxicity risk.

[0003] With the in-depth study of organic photosensitizer, high conjugated organic molecules show unique advantages due to their controllable electronic structure and excellent optical properties. This kind of molecule can effectively enhance the light capture ability by expanding the π conjugated system, and reasonable molecular design can optimize the excited state energy transfer process. However, the existing high conjugated photosensitizer still has the problems of complicated synthesis method, low yield and other deficiencies, which restricts its practical application.

[0004] In view of the above problems, the present application develops a new type of high conjugated photosensitizer YB-D and its efficient preparation method. The photosensitizer realizes the significant improvement of ROS generation efficiency through unique molecular design, and its optimized synthesis process solves the problem that the yield and purity are difficult to be considered in the prior art, providing a better choice for photodynamic therapy. SUMMARY

[0005] The main purpose of the present application is to provide a high conjugated photosensitizer with high ROS generation capacity and a preparation method thereof.

[0006] The technical scheme of the present application is as follows:

[0007] A high conjugated photosensitizer with high ROS generation capacity, the chemical structural formula of the photosensitizer is:

[0008]

[0009] YB-D.

[0010] The preparation method of the high conjugated photosensitizer with high ROS generation capacity, the method comprises the following synthesis path:

[0011]

[0012] YBYB-D

[0013] The method comprises the following steps:

[0014] (1) Under the protection of inert atmosphere, compound YB, 1,4-dioxane, 4-diphenylaminoboronic acid are placed in a reaction container, and a homogeneous system is formed by magnetic stirring; then, a catalyst, potassium carbonate and deionized water are sequentially added, and after the reaction system is replaced by nitrogen, a coupling reaction is carried out at room temperature to reflux temperature, and a target reaction mixture is obtained;

[0015] (2) The reaction mixture obtained in step (1) is washed with water, extracted with an organic solvent, dried with anhydrous sodium sulfate, concentrated under reduced pressure, and then purified by column chromatography to obtain the target product YB-D, which is confirmed by structure characterization to be a high conjugated photosensitizer.

[0016] In step (1), the feeding ratio of compound YB, 4-diphenylaminoboronic acid, catalyst and potassium carbonate is 1:1-8:0.01-0.1:2-5.

[0017] The catalyst includes one of tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0) and bis(tricyclohexylphosphine)palladium(0).

[0018] In step (1), the volume ratio of 1,4-dioxane and deionized water is 6-9:1.

[0019] In step (1), the feeding order of first adding compound YB, 1,4-dioxane and 4-diphenylaminoboronic acid, and then adding the catalyst and potassium carbonate, can ensure that the reactants are fully dissolved and prevent the catalyst from being inactivated under alkaline conditions. If the feeding order is changed, the catalyst may be decomposed or the substrate may have a side reaction.

[0020] The heating reflux reaction temperature of step (1) is 30-90℃, and the heating time is 1-5 hours.

[0021] In another aspect, the high conjugated photosensitizer or the high conjugated photosensitizer prepared by the method is used in the preparation of a drug for the photodynamic treatment of cancer tumor cells.

[0022] The YB-D combined culture medium group obtained after the high conjugated photosensitizer is incubated in the culture medium for 3-5 hours.

[0023] The high conjugated photosensitizer or YB-D combined culture medium group produces reactive oxygen species (ROS) under 600-700nm light irradiation, induces apoptosis of cancer cells, and achieves treatment of tumor cells.

[0024] The cancer tumor cells include human cervical cancer cells, and the human cervical cancer cells include Hela cells.

[0025] The maximum absorption wavelength of the photosensitizer in dimethyl sulfoxide is 641 nm.

[0026] The present application has the following advantages:

[0027] (1) The present application provides a high conjugated photosensitizer based on halogenated BOPYIN and a preparation method thereof. The photosensitizer realizes high efficient ROS generation ability and excellent light stability through precise molecular design, and shows significant photodynamic killing effect on Hela tumor cells under 600-700 nm (preferably 635 nm) laser irradiation. At the same time, the photosensitizer has very low toxicity to normal cells under no light condition, and has good biological safety and tumor selective accumulation characteristics. The photosensitizer not only solves the problem that ROS yield and biological safety are difficult to be considered in the prior art, but also provides a convenient site for subsequent development of series of derivatives in the molecular structure, which shows important clinical application value and broad industrialization prospect in the field of tumor photodynamic therapy.

[0028] (2) The synthesis reaction condition of the high conjugated photosensitizer with high efficient ROS generation ability is easy to control, and the preparation method realizes preparation of the target product with high yield and high purity by optimizing the reaction condition, and the process flow is simple and has industrialization advantages. BRIEF DESCRIPTION OF DRAWINGS

[0029] Figure 1 is a hydrogen spectrum of compound YB-D obtained in Example 9.

[0030] Figure 2 is a single crystal graph of compound YB-D obtained in Example 9.

[0031] Figure 3 is an ultraviolet absorption spectrum graph of compound YB-D obtained in Example 9.

[0032] Figure 4 is a cell live and dead staining image of compound YB-D obtained in Example 9.

[0033] Figure 5 is a cell level ROS generation ability detection image of compound YB-D obtained in Example 9. DETAILED DESCRIPTION

[0034] The present application will be further described below in combination with examples, but the scope of protection required by the present application is not limited to the scope expressed by the examples.

[0035] Example 1

[0036] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (289.14 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (11.56 mg, 0.01 mmol), potassium carbonate (276.00 mg, 2.0 mmol) and deionized water (3.00 mL) were added in turn. The system was replaced with nitrogen for three times, then stirred at 30 °C oil bath for 5 hours (TLC monitoring reaction complete). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, it was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5:1, v / v) to obtain the target product YB-D (210.14 mg, black solid), yield 27 %.

[0037]

[0038] YB-D

[0039] Example 2

[0040] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (1156.56 mg, 4.0 mmol), tetrakis(triphenylphosphine)palladium(0) (11.56 mg, 0.01 mmol), potassium carbonate (276.00 mg, 2.0 mmol) and deionized water (3.00 mL) were added in turn. The system was replaced with nitrogen for three times, then stirred at 30 °C oil bath for 5 hours (TLC monitoring reaction complete). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, it was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5:1, v / v) to obtain the target product YB-D (264.63 mg, black solid), yield 34 %. When the amount of 4-diphenylaminophenylboronic acid is increased by 3.0 mmol compared with Example 1, the yield of product YB-D is increased by 7 %.

[0041]

[0042] YB-D

[0043] Example 3

[0044] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (2313.12 mg, 8.0 mmol), tetrakis(triphenylphosphine)palladium(0) (11.56 mg, 0.01 mmol), potassium carbonate (276.00 mg, 2.0 mmol), and deionized water (3.00 mL) were added in sequence. The system was replaced with nitrogen three times, and then stirred at 30 °C in an oil bath for 5 hours (TLC monitoring reaction completion). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the target product YB-D (365.81 mg, black solid) was obtained by silica gel column chromatography purification (eluent: petroleum ether / dichloromethane = 5:1, v / v), with a yield of 47 %. When the amount of 4-diphenylaminophenylboronic acid was increased by 4.0 mmol compared to Example 2, the yield of product YB-D increased by 13 %.

[0045]

[0046] YB-D

[0047] Example 4

[0048] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (2313.12 mg, 8.0 mmol), tetrakis(triphenylphosphine)palladium(0) (11.56 mg, 0.01 mmol), potassium carbonate (276.00 mg, 2.0 mmol), and deionized water (3.00 mL) were added in sequence. The system was replaced with nitrogen three times, and then stirred at 60 °C in an oil bath for 4 hours (TLC monitoring reaction completion). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the target product YB-D (381.38 mg, black solid) was obtained by silica gel column chromatography purification (eluent: petroleum ether / dichloromethane = 5:1, v / v), with a yield of 49 %. When the reaction temperature was increased by 30 °C compared to Example 3, the yield of product YB-D increased by 2 %, and the reaction time decreased by 1 hour.

[0049]

[0050] YB-D

[0051] Example 5

[0052] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (2313.12 mg, 8.0 mmol), tetrakis(triphenylphosphine)palladium(0) (11.56 mg, 0.01 mmol), potassium carbonate (276.00 mg, 2.0 mmol), and deionized water (3.00 mL) were added in sequence. The system was replaced with nitrogen three times, and then stirred at 90 °C for 2 hours (TLC monitoring reaction completion). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the target product YB-D (428.07 mg, black solid) was obtained by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5:1, v / v) with a yield of 55 %. When the reaction temperature was increased by 30 °C compared to Example 4, the yield of product YB-D increased by 6 %, and the reaction time decreased by 2 hours.

[0053]

[0054] YB-D

[0055] Example 6

[0056] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (2313.12 mg, 8.0 mmol), tetrakis(triphenylphosphine)palladium(0) (34.68 mg, 0.03 mmol), potassium carbonate (276.00 mg, 2.0 mmol), and deionized water (3.00 mL) were added in sequence. The system was replaced with nitrogen three times, and then stirred at 90 °C for 2 hours (TLC monitoring reaction completion). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the target product YB-D (490.34 mg, black solid) was obtained by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5:1, v / v) with a yield of 63 %. When the amount of tetrakis(triphenylphosphine)palladium(0) was increased by 0.02 mmol compared to Example 5, the yield of product YB-D increased by 8 %.

[0057]

[0058] YB-D

[0059] Example 7

[0060] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (2313.12 mg, 8.0 mmol), tetrakis(triphenylphosphine)palladium(0) (57.80 mg, 0.05 mmol), potassium carbonate (276.00 mg, 2.0 mmol), and deionized water (3.00 mL) were added in sequence. The system was replaced with nitrogen three times, and then stirred at 90 °C for 2 hours (TLC monitoring reaction completion). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the target product YB-D (505.90 mg, black solid) was obtained by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5:1, v / v) with a yield of 65 %. When the amount of tetrakis(triphenylphosphine)palladium(0) was increased by 0.02 mmol compared to Example 6, the yield of product YB-D increased by 2 %.

[0061]

[0062] YB-D

[0063] Example 8

[0064] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (2313.12 mg, 8.0 mmol), tetrakis(triphenylphosphine)palladium(0) (57.80 mg, 0.05 mmol), potassium carbonate (552.00 mg, 4.0 mmol), and deionized water (3.00 mL) were added in sequence. The system was replaced with nitrogen three times, and then stirred at 90 °C for 2 hours (TLC monitoring reaction completion). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the target product YB-D (505.90 mg, black solid) was obtained by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5:1, v / v) with a yield of 65 %. When the amount of tetrakis(triphenylphosphine)palladium(0) was increased by 0.02 mmol compared to Example 6, the yield of product YB-D increased by 2 %.

[0065]

[0066] YB-D

[0067] Example 9

[0068] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (2313.12 mg, 8.0 mmol), tetrakis(triphenylphosphine)palladium(0) (57.80 mg, 0.05 mmol), potassium carbonate (690.00 mg, 5.0 mmol), and deionized water (3.00 mL) were added in turn. The system was replaced with nitrogen three times, and then stirred at 90 °C in an oil bath for 2 hours (TLC monitoring reaction completion). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), and the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the target product YB-D (575.95 mg, black solid) was obtained by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5:1, v / v), with a yield of 74 %. When the amount of potassium carbonate was increased by 1.0 mmol compared to Example 8, the yield of product YB-D increased by 2 %.

[0069] The mother liquor was prepared by dissolving black solid YB-D (7.78 mg, 0.01 mmol) in 1 mL of dichloromethane, and 3 μL of the mother liquor was added to 3 mL of toluene, dichloromethane, ethyl acetate, acetone, methanol, and dimethyl sulfoxide, respectively, to measure the absorption wavelength of the compound (see Table 1). Figure 3 The compound has a longer absorption wavelength, with the maximum absorption wavelength in toluene solvent (651 nm).

[0070]

[0071] YB-D

[0072] Example 10

[0073] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (2313.12 mg, 8.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (45.79 mg, 0.05 mmol), potassium carbonate (690.00 mg, 5.0 mmol) and deionized water (3.00 mL) were added in turn. The system was replaced with nitrogen for three times, then stirred at 90 °C oil bath for 2 hours (TLC monitoring reaction complete). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, it was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5:1, v / v) to obtain the target product YB-D (575.95 mg, black solid), yield 72 %. When the catalyst was replaced by tris(dibenzylideneacetone)dipalladium(0) instead of palladium(0), tetraphenylphosphine in Example 9, the yield of product YB-D decreased by 2 %.

[0074] Example 11

[0075] In a 50 mL round-bottom flask, compound YB (403.97 mg, 1.0 mmol) and 1,4-dioxane (27.00 mL) were added and stirred until completely dissolved, then 4-diphenylaminophenylboronic acid (2313.12 mg, 8.0 mmol), bis(tri-tert-butylphosphine)palladium(0) (45.79 mg, 0.05 mmol), potassium carbonate (690.00 mg, 5.0 mmol) and deionized water (3.00 mL) were added in turn. The system was replaced with nitrogen for three times, then stirred at 90 °C oil bath for 2 hours (TLC monitoring reaction complete). After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water (3 x 20 mL), extracted with dichloromethane (3 x 30 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, it was purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane = 5:1, v / v) to obtain the target product YB-D (575.95 mg, black solid), yield 70 %. When the catalyst was replaced by bis(tri-tert-butylphosphine)palladium(0) instead of palladium(0), tetraphenylphosphine in Example 9, the yield of product YB-D decreased by 4 %.

[0076] Example 12 Cell live / dead staining experiment of compound YB-D

[0077] The cell live / dead staining experiment was carried out using the Hela cell line. Well-grown cells were seeded at 1.0 x 10 5Cells were seeded in 6-well cell culture plates (Corning Costar) at a density of 1.0 x 10 2 ) and incubated overnight at 37°C in a 5% CO2 incubator. Four groups were set up: (1) control group (fresh medium without Hela cells); (2) light-only group (635 nm, 1.0 W / cm 2 ) for 4 hours.

[0078] Then, each group of cells was stained with 10 μL Calcein-AM (1.0 mM, live cell staining) and 10 μL PI (1.0 mM, dead cell staining). The cells in the second and fourth groups were irradiated with 635 nm laser (1.0 W / cm 5 ) after staining. After incubation for 30 minutes, the results were observed and photographed using a fluorescence microscope (Olympus, BX51). The results showed that the survival rate of the control group was the highest, and a small amount of cell death occurred in the light-only group. Some cell death occurred in the YB-D-only group, and almost all cancer cells were killed in the YB-D and light group, indicating that YB-D had a significant photodynamic therapy effect under 635 nm laser irradiation.

[0079] Example 13. Detection of ROS production at the cellular level by compound YB-D

[0080] Hela cells (ATCC CCL-2) in the logarithmic growth phase were digested with 0.25% trypsin-EDTA and seeded in 6-well cell culture plates (Corning Costar) at a density of 1.0 x 10 5 Each well was added with 2 mL of DMEM high-glucose medium (HyClone) containing 10% fetal bovine serum (Gibco). The cells were incubated overnight at 37°C in a 5% CO2, saturated humidity cell incubator (Thermo Scientific). The experimental group was added with complete medium containing 5 μM YB-D (medium containing YB-D), and the control group was added with the same volume of DMSO (final concentration <0.1%). After incubation for 4 hours, the medium was aspirated, and 10 μM DCFH-DA (Sigma-Aldrich, dissolved in serum-free medium) working solution was added, and incubated at 37°C for 30 minutes in the dark. The pre-cooled PBS (pH 7.4) was gently washed for 5 minutes for 3 times to completely remove the extracellular probe.

[0081] A 635 nm near-infrared laser (Beijing Hi-Tech Optoelectronic, power density 1.0 W / cm2 The cells were vertically irradiated with a 3-cm-diameter light spot for 15 min at a distance of 10 cm. Immediately after irradiation, the cells were fixed with 4% paraformaldehyde for 15 min and then washed with PBS. Anti-fluorescence quenching mounting medium (containing 1 μg / mL DAPI, Beyotime) was added to mount the cells.

[0082] The fluorescence microscope (Olympus BX51, equipped with a DP72 digital camera) was used for observation. The U-MNIBA filter set (excitation wavelength 470-495 nm, emission wavelength 510-550 nm) was used to detect the DCFH-DA fluorescence (green), and the U-MWU filter set (excitation wavelength 330-385 nm, emission wavelength 420 nm) was used to detect the DAPI (blue). It was found that the number of cells with green coloration was large, indicating that the photosensitizer had a strong ability to produce reactive oxygen species (ROS).

Claims

1. A highly conjugated photosensitizer, characterized in that, The chemical structural formula of the photosensitizer is: YB-D.

2. The method for preparing the highly conjugated photosensitizer according to claim 1, characterized in that, The method comprises the following synthesis path: (1) under the protection of inert atmosphere, compound YB, 1,4-dioxane, 4-diphenylaminophenyl boronic acid are placed in a reaction container to form a homogeneous system by stirring; then, a catalyst, potassium carbonate and deionized water are sequentially added, and after the reaction system is replaced by nitrogen, a coupling reaction is carried out at room temperature to reflux temperature to obtain a target reaction mixture; (2) the reaction mixture obtained in step (1) is washed with water, extracted with an organic solvent, dried with anhydrous sodium sulfate, concentrated under reduced pressure, and then purified by column chromatography to obtain the target product YB-D.

3. The preparation method according to claim 2, characterized in that, In step (1), the feeding ratio of compound YB, 4-diphenylaminophenyl boronic acid, catalyst and potassium carbonate is 1:1-8:0.01-0.1:2-5.

4. The production method according to claim 2, characterized by, The catalyst in step (1) is one of tetrakis(triphenylphosphine)palladium, tris(dibenzylideneacetone)dipalladium and bis(tricyclohexylphosphine)palladium.

5. The preparation method according to claim 2, characterized in that, The heating temperature of step (1) is 30-90℃, and the heating time is 1-5 hours.

6. Use of the high conjugated photosensitizer of claim 1 or the high conjugated photosensitizer prepared by the method of any one of claims 2-5 in the preparation of a drug for the photodynamic treatment of cancer tumor cells.

7. Use according to claim 6, characterized in that, The YB-D combined culture medium group is obtained after the high conjugated photosensitizer is incubated in the culture medium for 3-5 hours.

8. Use according to claim 7, characterized in that, The high conjugated photosensitizer or the YB-D combined culture medium group generates reactive oxygen species (ROS) under 600-700 nm light irradiation, induces apoptosis of cancer cells, and achieves treatment of tumor cells.

9. Use according to claim 8, characterized in that, The cancer tumor cells are human cervical cancer cells, and the human cervical cancer cells are Hela cells.

10. Use according to claim 9, characterized in that, The photosensitizer absorbs a wavelength of 641 nm.

Images