Photosensitive lipid nanoparticle containing phenanthrosulfonyl diimine structure, preparation method and tumor phototherapy application

Abstract

The invention discloses a photosensitive lipid nanoparticle containing a phenanthrosulfonyl diimine structure, a preparation method and tumor phototherapy application, and belongs to the technical field of biomedical materials. The I-type photosensitizer with near-infrared two-region luminescence is constructed by taking phenanthrosulfonyl diimine with strong electron-withdrawing capability as a new acceptor skeleton and tetraphenyl ethylene bridged diphenylamine as a donor. Due to the relatively small singlet state and triplet state energy level difference and the strong charge transfer effect, the intersystem crossing process between excited states can be accelerated, and the generation of active oxygen can be promoted. The ultraviolet-visible absorption wavelength of the lipid nanoparticles CTGU-1 (at) NPs prepared by ultrasound is 500 to 900 nm, and the maximum fluorescence emission wavelength is 1046 nm. Under the irradiation of a light source with the wavelength of 808 nm, I-type active oxygen (hydroxyl free radicals) can be efficiently generated, and excellent photo-thermal performance is achieved. The novel acceptor group with strong electron withdrawing capability provides a novel molecular design strategy for constructing a novel near-infrared second-region biological diagnosis and treatment type I photosensitizer molecule.

Description

Technical Field

[0001] The invention relates to a method for preparing near-infrared II luminescent lipid nanoparticles based on a novel phenanthrenesulfonyl diimide receptor structure, which can simultaneously achieve efficient photothermal and type I photodynamic effects, belonging to the field of modern phototherapy. Background Technology

[0002] Phototherapy is a non-invasive, spatiotemporally resolved precision medicine that can simultaneously achieve real-time diagnosis and in-situ treatment, thus attracting significant attention in the clinical intervention of malignant tumors. In recent years, the integrated phototherapy and diagnostic system has developed rapidly, its core consisting of photothermal therapy (PTT) and photodynamic therapy (PDT). PTT generates localized high temperatures in the tumor area through efficient light-thermal conversion, selectively ablating tumor cells, offering advantages such as high specificity, strong controllability, and minimal damage to normal tissues. Simultaneously, the accelerated blood flow induced by PTT can improve tumor oxygenation levels and promote the accumulation of photosensitizers within the tumor, creating favorable conditions for subsequent PDT. PDT, on the other hand, utilizes photosensitizers to generate reactive oxygen species (ROS) under light irradiation, causing irreversible oxidative damage to biological macromolecules such as DNA, proteins, and lipids, thereby inducing tumor cell apoptosis or necrosis. Traditional type II PDT is heavily dependent on oxygen, while solid tumors are generally in a hypoxic state, severely weakening its efficacy. In contrast, type I PDT uses photosensitizers to stimulate the generation of highly cytotoxic free radicals (such as •O2). − •OH) has low oxygen concentration requirements and can still exert a significant killing effect in hypoxic microenvironments.

[0003] Fluorescence imaging, due to its real-time tracking, high resolution, and high sensitivity, is gradually becoming a promising imaging technique in disease diagnosis. However, compared with traditional magnetic resonance imaging, positron emission tomography (PET), and ultrasound imaging, the clinical application of fluorescence imaging is still in its early stages, mainly limited by insufficient penetration depth into biological tissues. Compared with fluorescent dyes in the visible and near-infrared I regions, near-infrared II (NIR-II, 1000 ~ 1700 nm) fluorescent dyes can more effectively reduce interference from light scattering, absorption, and autofluorescence in biological tissues, significantly increasing imaging depth and resolution. To date, most reported NIR-II fluorescent dyes are cyanine, bodily, and benzothiadiazole derivatives; NIR-II dyes with novel molecular skeleton characteristics are rarely reported, which severely limits their practical biomedical applications.

[0004] Therefore, developing novel multifunctional type I photosensitizers with NIR-II fluorescence imaging capabilities and efficient photothermal properties is of great significance for research on tumor phototherapy and integrated diagnosis and treatment. Summary of the Invention

[0005] The purpose of this invention is to design and prepare a photosensitive lipid nanoparticle that simultaneously possesses NIR-II luminescence, efficient photothermal, and photodynamic effects. Under 808 nm laser irradiation, this nanoparticle can rapidly convert triplet oxygen into hydroxyl groups, simultaneously generating heat that raises the local temperature by 26-38 °C. This effect is superior to commercially available photosensitizers used in photodynamic and photothermal therapy, and can be applied to near-infrared II fluorescence imaging-guided photodynamic and photothermal synergistic therapy for tumors.

[0006] The photosensitizer CTGU-1, which simultaneously possesses NIR-II fluorescence, photodynamic, and photothermal therapeutic properties, is structurally characterized by a donor-receptor-donor (DAD) structure, using phenanthroline sulfonyl diimide as the novel acceptor backbone and tetraphenylethylene-bridged diphenylamine as the donor. Its structure is as follows:

[0007] The method for preparing the NIR-II photosensitizer CTGU-1 includes the following steps: (1) Synthesis route

[0008] (2) Synthesis steps Step 1: Using 3,6-dibromophenanthroquinone and sulfonamide as raw materials and glacial acetic acid as the reaction solvent, a heating dehydration cyclization reaction is carried out to prepare compound 1; Step 2: Using compound 1 and tetraphenylethylene-bridged diphenylamine borate (compound 2) as raw materials, a palladium catalyst and a base are used to carry out a Suzuki coupling reaction to prepare the target molecule CTGU-1.

[0009] The solvent for the dehydration condensation reaction in step one is glacial acetic acid, and the reaction temperature is 100-120℃; the Suzuki reaction temperature in step two is 80-100℃, and the palladium catalyst includes any one of tetraphenylphosphine palladium, 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride, palladium dichloride, triphenylphosphine palladium dichloride, etc.; the base includes any one of potassium phosphate, potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, etc.

[0010] In step one, it is inevitable for those skilled in the art that post-processing of the product is included. Specifically, the product obtained after the reaction is cooled to room temperature and extracted four times with chloroform and water. The combined organic phases are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product is purified by silica gel column chromatography using dichloromethane / petroleum ether (v / v = 1 / 20) as the eluent to obtain a solid product.

[0011] In step two, it is inevitable for those skilled in the art that post-processing of the product is involved. Specifically, the product obtained after the reaction is cooled to room temperature and extracted four times with chloroform and water. The combined organic phases are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product is purified by silica gel column chromatography using dichloromethane / petroleum ether (v / v = 1 / 1) as the eluent to obtain a solid product.

[0012] In some embodiments, in step two, compound 1, compound 2, palladium catalyst and base are added to a pressure-resistant bottle under argon protection, with tetrahydrofuran and water as solvents, and the temperature is raised to 80-100°C for 20-24 hours.

[0013] In step three, it is inevitable for those skilled in the art that post-processing of the product is involved. Specifically, the product obtained after the reaction is cooled to room temperature, the reaction mixture is filtered through diatomaceous earth, and extracted four times with chloroform and water. The combined organic phases are dried over anhydrous sodium sulfate and concentrated under reduced pressure. Then, silica gel column chromatography is performed to separate the product into a black solid.

[0014] This invention provides lipid nanoparticles CTGU-1@NPs, wherein the NIR-II fluorescent, photodynamic, and photothermal CTGU-1 is subjected to distearate phosphatidylethanolamine-polyethylene glycol 2000 (DSPE-PEG). 2000 Lipid nanoparticles CTGU-1@NPs were prepared by sonicating amino-polyethylene glycol folic acid (NH2-PEG-FA) in tetrahydrofuran (THF) solution.

[0015] The specific steps are as follows: CTGU-1, DSPE-PEG, and NH2-PEG-FA are dissolved in THF to obtain a mixed solution; this mixed solution is injected into deionized water and sonicated for 10-15 min to obtain a lipid microemulsion; the lipid microemulsion is transferred into a dialysis bag (8KD-14KD) and dialyzed with deionized water for 30-35 h, with the deionized water being replaced every 2-3 h, so that the photosensitizer is encapsulated by the polymer material and self-assembled into nanoparticles; at the same time, after removing THF, it is lyophilized and stored for later use to obtain lipid nanoparticles CTGU-1@NPs.

[0016] The mass ratio of the NIR-II fluorescence, photodynamic, and photothermal therapy organic molecule (CTGU-1), distearate phosphatidylethanolamine-polyethylene glycol 2000, and aminopolyethylene glycol folic acid is 1:6-10:3-5, and more preferably 1:6.6:3.7.

[0017] The prepared lipid nanoparticles CTGU-1@NPs have a particle size of 110–120 nm. The absorption wavelength is 500–900 nm, and the maximum fluorescence emission wavelength is 1030–1060 nm.

[0018] In some preferred embodiments, irradiation with a near-infrared laser (e.g., at 700-808 nm) can rapidly convert triplet oxygen into hydroxyl radicals, while simultaneously generating heat that raises the local temperature by approximately 26-38 °C. The nanoparticles remain stable for more than a week.

[0019] Another technical solution of the present invention provides a catalytic degradation agent for dye organic compounds, comprising the aforementioned lipid nanoparticles CTGU-1@NPs. Specifically, the NIR-II fluorescent, photodynamic, and photothermal therapeutic lipid nanoparticles CTGU-1@NPs are used as a photodynamic therapeutic agent in the degradation of 2,7-dichlorofluorescein diacetate (DCFH-DA) and hydroxyphenylfluorescein (HPF). The photodynamic effect of this compound is investigated using total reactive oxygen species (ROS) yield and hydroxyl radicals, and the degradation kinetics curves of the ROS indicators DCFH-DA and HPF are tested.

[0020] Another technical solution of the present invention is to provide a photothermal therapy photosensitizer, wherein the photothermal therapy photosensitizer comprises the aforementioned lipid nanoparticles CTGU-1@NPs. The application of the aforementioned NIR-II fluorescence, photodynamic, and photothermal therapy lipid nanoparticles CTGU-1@NPs as a photothermal therapy photosensitizer is described. The photothermal effect of this compound is investigated using real-time temperature monitoring.

[0021] Another technical solution of the present invention is the application of the aforementioned NIR-II fluorescent, photodynamic, and photothermal lipid nanoparticles CTGU-1@NPs as a photothermal photosensitizer in the preparation of a drug for treating breast cancer, wherein the breast cancer is human breast cancer MCF-7 cells.

[0022] Adding lipid nanoparticles CTGU-1@NPs to tumor cells and culturing them for 48 h showed no significant cytotoxicity. However, irradiation with an 808 nm near-infrared laser resulted in significant cytotoxicity to tumor cells. 30 μM CTGU-1@NPs could efficiently kill tumor cells under light irradiation, demonstrating superior phototherapy effects.

[0023] The tumor cell toxicity described in this invention is achieved through the synergistic effect of photodynamic and photothermal processes.

[0024] The photosensitizer provided by this invention is relatively simple to synthesize and has a high yield. The prepared lipid nanoparticles have small particle size, high stability, and can achieve NIR-II fluorescence emission; the yield of hydroxyl radicals is significantly higher than that of commercial photosensitizers, with excellent photothermal properties and good stability, achieving a three-in-one tumor phototherapy effect. Attached Figure Description

[0025] Figure 1The image shows the UV absorption spectrum of CTGU-1@NPs in aqueous solution in Example 2.

[0026] Figure 2 The fluorescence emission spectrum of CTGU-1@NPs in aqueous solution in Example 3 is shown.

[0027] Figure 3 Example 4 was performed at 808 nm and 0.5 W / cm. 2 The fluorescence intensity of the total reactive oxygen species indicator DCFH-DA induced by CTGU-1@NPs at 525 nm as a function of time increases under laser irradiation.

[0028] Figure 4 Example 5 was performed at 808 nm and 0.5 W / cm. 2 The fluorescence intensity of HPF, a hydroxyl radical indicator induced by CTGU-1@NPs, increases over time at 515 nm under laser irradiation.

[0029] Figure 5 Example 6 was performed at 808 nm and 0.5 W / cm. 2 Temperature variation curve of CTGU-1@NPs over time under laser irradiation.

[0030] Figure 6 This is a stability performance diagram of the photothermal conversion of CTGU-1@NPs in Example 7.

[0031] Figure 7 The figures show the results of the tumor cell toxicity and phototoxicity experiments of CTGU-1@NPs in Examples 8 and 9. Detailed Implementation

[0032] The ultrasonic instrument used for the preparation of the lipid nanoparticles is a probe-type ultrasonic generator.

[0033] The absorption spectroscopy test was performed using a UV-Vis spectrophotometer.

[0034] The particle size and potential were measured using a nanoparticle size potentiometer.

[0035] The laser used for the photodynamic and photothermal effect test is an 808 nm semiconductor laser lamp.

[0036] The tumor cells used in the tumor cell lethality experiment were MCF-7, etc.

[0037] The following experiments and examples are used to further illustrate, but are not limited to, the present invention.

[0038] Example 1 (1) Synthesis route

[0039] (2) Synthesis steps Preparation of Compound 1: In a 150 mL two-necked flask, 3,6-dibromophenanthroline (3.66 g, 10 mmol), sulfonamide (1.92 g, 20 mmol), and 20 mL of glacial acetic acid were added under argon protection. The mixture was refluxed at 120 °C for 6 hours. After cooling to room temperature, the mixture was extracted with chloroform and water. The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / petroleum ether (v / v = 1 / 20) as eluent to give 3.79 g of an orange solid, yielding 89%. 1 H NMR (400 MHz, CDCl3) δ [ppm]: 8.12 (d, J = 8.3 Hz, 2H), 8.08 (d, J = 1.6 Hz, 2H), 7.81 (dd, J = 8.4, 1.8 Hz, 2H).

[0040] Preparation of CTGU-1: In a 100 mL pressure-resistant bottle, under argon protection, compound 1 (2.13 g, 5 mmol), compound 2 (6.25 g, 10 mmol), tetraphenylphosphine palladium (0.56 g, 0.05 mmol), potassium phosphate (4.24 g, 20 mmol), 50 mL tetrahydrofuran, and 20 mL water were added. The mixture was heated to 85 °C and reacted for 22 hours. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth and extracted with chloroform and water. The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Separation was then performed by silica gel column chromatography to give 3.92 g of a black solid, yield 62%. 1 H NMR (400 MHz, CD2Cl2) δ [ppm]: 8.41 - 8.22(m, 4H), 7.89 (dd, J = 8.1, 1.6 Hz, 2H), 7.62 (d, J = 8.6 Hz, 4H), 7.28 - 7.22(m, 4H), 7.08 - 6.96 (m, 40H), 6.88 - 6.15 (m, 4H), 6.79 - 6.76 (m, 4H). 13 CNMR (100 MHz, CD2Cl2) δ[ppm]: 160.01, 150.46, 150.11, 146.80, 145.01, 143.99,143.42, 141.02, 139.84, 135.99, 132.63, 132.41, 132.33, 129.50, HRMS: (ESI) m / z calcd for C 90 H 62 N4O2S [M+H] + :1263.46662; found: 1263.46118.

[0041] Example 2 A lipid nanoparticle CTGU-1@NPs was prepared by dissolving the compound CTGU-1, DSPE-PEG, and NH2-PEG-FA obtained in Example 1 in THF to obtain a mixed solution. The mixed solution was injected into deionized water and sonicated for 10-15 min to obtain a lipid microemulsion. The lipid microemulsion was transferred into a dialysis bag (8KD-14KD) and dialyzed with deionized water for 30-35 h, with the deionized water being replaced every 2-3 h. This allowed the photosensitizer to be encapsulated by the polymer material and self-assembled into nanoparticles. After removing THF, the nanoparticles were lyophilized and stored for later use, thus obtaining the lipid nanoparticles CTGU-1@NPs.

[0042] The mass ratio of the NIR-II fluorescence, photodynamic, and photothermal therapy organic molecule (CTGU-1), distearate phosphatidylethanolamine-polyethylene glycol 2000, and aminopolyethylene glycol folic acid is 1 / 6.6 / 3.7.

[0043] A 20.0 μM aqueous solution of CTGU-1@NPs was prepared, and the absorption spectrum of the aqueous solution of nanoparticles was measured using a UV spectrophotometer.

[0044] Example 3 The near-infrared II fluorescence emission spectrum of the CTGU-1@NPs nanoparticle aqueous solution in Example 2 was measured using a near-infrared II photoluminescence spectrometer.

[0045] Example 4 Experiment on total ROS production by lipid nanoparticles CTGU-1@NPs in aqueous solution: Using DCFH-DA as the total reactive oxygen species indicator, the test solution was prepared with a concentration of 20.0 μM for the photosensitizer CTGU-1@NPs and 5.0 μM for DCFH-DA. The test was conducted at 808 nm and 0.5 W / cm². 2 The PDT effect of CTGU-1@NPs was evaluated by the extent to which DCFH-DA was degraded to DCF under laser irradiation. The results are shown in the figure. Under laser irradiation, the total reactive oxygen species indicator DCFH-DA induced by CTGU-1@NPs was converted to DCF, and the fluorescence signal at 525 nm at an excitation wavelength of 488 nm increased over time. Figure 3 This indicates that CTGU-1@NPs can generate reactive oxygen species and has good potential for photodynamic therapy.

[0046] Example 5 Experiment on the generation of hydroxyl radicals by lipid nanoparticles CTGU-1@NPs in aqueous solution: Using HPF as a hydroxyl radical indicator, the test solution was prepared with a concentration of 20.0 μM for the photosensitizer CTGU-1@NPs and 5.0 μM for HPF. The test was conducted at 808 nm and 0.5 W / cm². 2 Laser irradiation was used to evaluate the effect of CTGU-1@NPs in producing type I reactive oxygen species (ROS), based on the degree of HPF oxidation. The results are shown in the figure. Under laser irradiation, the hydroxyl reactive oxygen species indicator HPF induced by CTGU-1@NPs was converted into highly fluorescent HPF, with a fluorescence signal at 515 nm increasing over time at an excitation wavelength of 490 nm. Figure 4 This indicates that CTGU-1@NPs can generate hydroxyl reactive oxygen species and has good potential for type I photodynamic therapy.

[0047] Example 6 Photothermal effect experiment of lipid nanoparticles CTGU-1@NPs: A certain amount of CTGU-1N@NPs was taken and diluted with water to a photosensitizer concentration of 15, 25, 50, and 100 μM. The photosensitizers were then tested at 808 nm and 0.5 W / cm². 2 Under laser irradiation, a temperature probe was inserted to monitor the system's temperature change in real time over 10 minutes, and a temperature-time curve was plotted. Experimental results (e.g.) Figure 5 Under light irradiation, the temperature of CTGU-1@NPs rises rapidly, from room temperature to 55 ℃ in 5 minutes and to 62 ℃ in 10 minutes, demonstrating excellent photothermal conversion effect.

[0048] Example 7 Photothermal cycling experiment of lipid nanoparticles CTGU-1@NPs: Example 6 was subjected to repeated light-cool-light cycle tests, and the temperature change of the system was monitored. The experimental results are as follows: Figure 6As shown, CTGU-1@NPs were heated by light, cooled, and then heated again. The temperature rise range was 25-67℃. Over five experimental cycles, the temperature rise was relatively stable, indicating that the system has a stable photothermal effect and can repeatedly produce a highly efficient photothermal conversion effect.

[0049] Example 8 Dark cytotoxicity assay of lipid nanoparticles CTGU-1@NPs: Using human breast cancer cell line MCF-7 as an example, the dark cytotoxicity of lipid nanoparticles CTGU-1@NPs was investigated. MCF-7 cells were cultured in 10 wells per well. 5 Cells were seeded at a density of 100 μL in 96-well plates. After 24 hours of culture, 100 μL of fresh culture medium containing lipid nanoparticles was added to each well (the photosensitizer concentration in each well after adding the culture medium was 10 μM, 20 μM, 30 μM, 40 μM, and 50 μM, respectively). After 48 hours of culture, 20 μL of MTT solution (prepared from sterile PBS buffer at a concentration of 5 mg / mL) was added to each well. After 4 hours of incubation, the culture medium was removed from each well, and 150 μL of DMSO was added to each well. The absorbance at 490 nm was recorded using a microplate reader to evaluate the cytotoxicity of CTGU-1@NPs. The experimental results showed that ( Figure 7 When the photosensitizer concentration in the lipid nanoparticles reached 50 μM, the survival rate of MCF-7 cells and HepG-2 cells still reached over 80%, indicating that the CTGU-1@NPs of the lipid nanoparticles had low cytotoxicity.

[0050] Example 9 Phototoxicity assay of CTGU-1@NPs lipid nanoparticles in tumor cells: Using human breast cancer cell line MCF-7 as an example, the tumor phototherapy activity of lipid nanoparticles CTGU-1@NPs was investigated. MCF-7 cells were cultured in 10-1 saturated wells. 5 Cells were seeded at a density of 100 μL in 96-well plates; after 24 h of culture, 100 µL of fresh culture medium containing lipid nanoparticles was added to each well (the photosensitizer concentration in each well after adding the culture medium was 10 μM, 20 μM, 30 μM, 40 μM, and 50 μM, respectively); after 24 h of culture, the culture plate was placed at 808 nm (0.8 W / cm²). 2Irradiation under a laser for 5 min was performed, with a light-protected culture plate as a control. After 24 h of culture, 20 μL of MTT solution (prepared from sterile PBS buffer at a concentration of 5 mg / mL) was added to each well. After 4 h of incubation, 150 μL of DMSO was added to each well after removing the culture medium. The absorbance at 490 nm was recorded using a microplate reader to evaluate the phototoxicity of CTGU-1@NPs. The results showed that under light irradiation, the survival rate of MCF-7 cells decreased significantly with increasing CTGU-1 concentration in the lipid nanoparticles. When the CTGU-1 concentration in the lipid nanoparticles reached 30 μM, the survival rate of MCF-7 cells was only about 7%, indicating that the CTGU-1@NPs of the lipid nanoparticles have high phototoxicity and good tumor phototherapy activity.

Claims

1. A photosensitive lipid nanoparticle containing a phenanthrenesulfonyldiimide structure, characterized in that, Using phenanthrenesulfonyl diimide as the acceptor backbone and tetraphenylethylene-bridged diphenylamine as the donor, a molecule with the donor-acceptor-donor DAD structure is constructed, the structure of which is as follows: 。 2. The method for preparing photosensitive lipid nanoparticles containing a phenanthrenesulfonyl diimide structure according to claim 1, characterized in that, Includes the following steps: Step 1: Using 3,6-dibromophenanthroquinone and sulfonamide as raw materials, a heating dehydration cyclization reaction was carried out under reaction solvent conditions to prepare compound 1; Step 2: Using compound 1 and tetraphenylethylene-bridged diphenylamine borate as raw materials, a Suzuki coupling reaction was carried out under palladium catalyst and alkaline conditions to obtain photosensitive lipid nanoparticles containing a phenanthrenesulfonyl diimide structure, namely CTGU-1; the synthetic route is as follows: 。 3. The method for preparing photosensitive lipid nanoparticles containing a phenanthrenesulfonyl diimide structure according to claim 2, characterized in that: The solvent for the dehydration condensation reaction in step one is glacial acetic acid, and the reaction temperature is 100-120℃; the reaction temperature for the Suzuki reaction in step two is 80-100℃.

4. A lipid nanoparticle, characterized in that, This includes the photosensitive lipid nanoparticles containing the phenanthrenesulfonyldiimide structure as described in claim 1, or the photosensitive lipid nanoparticles containing the phenanthrenesulfonyldiimide structure prepared by the method described in claim 2 or 3.

5. The lipid nanoparticles according to claim 4, characterized in that: The lipid nanoparticles also include distearate phosphatidylethanolamine-polyethylene glycol and aminopolyethylene glycol folic acid; Photosensitive lipid nanoparticles containing phenanthrenesulfonyldiimide structure were dissolved in a solvent with distearate phosphatidylethanolamine-polyethylene glycol and aminopolyethylene glycol folic acid. After adding water and sonicating, the lipid nanoparticles were obtained by dialyzing and named CTGU-1@NPs. The mass ratio of photosensitive lipid nanoparticles containing phenanthrenesulfonyl diimide structure, distearate phosphatidylethanolamine-polyethylene glycol, and aminopolyethylene glycol folic acid is 1:6-10:3-5.

6. The lipid nanoparticles according to claim 5, characterized in that: The prepared lipid nanoparticles CTGU-1@NPs had a particle size of 140 ~ 160 nm. z - Potential is -20 ~ 23 mV; absorption wavelength is 500 ~ 900 nm, and maximum fluorescence emission wavelength is 1030 ~ 1060 nm.

7. A catalytic degradation agent for dye organic matter, characterized in that, Including the lipid nanoparticles CTGU-1@NPs as described in any one of claims 4-6.

8. The dye catalytic degradation agent according to claim 7, characterized in that, The dye organics mentioned include 2,7-dichlorofluorescein diacetate or hydroxyphenylfluorescein.

9. A photosensitizer for photothermal therapy, characterized in that, The photothermal therapy photosensitizer includes the lipid nanoparticles CTGU-1@NPs as described in any one of claims 4-6.

10. The application of the photothermal photosensitizer according to claim 9 in the preparation of a drug for treating breast cancer, wherein the breast cancer is human breast cancer MCF-7 cells.

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