Benzo-C phenanthrene eutectic crystal and application thereof

Abstract

The invention discloses a benzo C phenanthrene eutectic material and an application thereof. The benzo C phenanthrene eutectic material is a benzo C phenanthrene-F4TCNQ eutectic. When the benzo-C phenanthrene eutectic material is used as a photo-thermal imaging and treatment reagent, a photo-thermal phenomenon can be generated under the excitation of infrared light, the benzo-C phenanthrene eutectic material has obvious response to lasers with different powers, the heating rate is high, the heating rate is relatively high, and in addition, an area with relatively high temperature can be visualized through a photo-thermal effect. The co-crystal material can be excited in an infrared band, has obvious response to a magnetic field, is favorable for developing a more effective magnetic response type photo-thermal treatment reagent, can be excited in the infrared band, is favorable for deep imaging of tumor tissues, and can provide a new thought and method for research in the photo-thermal and magnetic diagnosis and treatment fields.

Description

Technical Field

[0001] The invention relates to a benzophenanthrene eutectic and application thereof, belonging to the technical field of organic eutectic. Background Art

[0002] The photothermal effect refers to the phenomenon that when a material is irradiated with light, photons interact with the electrons inside the material, causing the material to generate heat. This process involves the exchange of energy between photons and matter, in which the energy of the photons is absorbed by the material and converted into thermal energy of the material molecules or atoms, thereby causing the temperature of the material to rise. In photothermal imaging technology, this photothermal effect occurs when the sample is excited by pulsed pump light, causing the temperature of the sample to change. Photothermal imaging technology and its related thermal imaging technology are non-invasive detection methods. Because they can detect small changes in temperature, they have broad application potential and important practical value in fields such as biomedicine.

[0003] Currently, the medical field has begun to use photothermal effects and photothermal imaging technology to diagnose and treat diseases, and photothermal therapy has become the focus of research. The current photothermal materials have a low temperature rise, which limits their application in the medical field. The magnetic field is a physical field that describes a physical phenomenon that exists in the space around a magnet or a moving charge. The magnetic field exerts a magnetic force on the magnet placed in it, and also exerts a force on the moving charge. Therefore, the temperature of photothermal therapy can be increased by the magnetic field. At present, there are few organic eutectics that are magnetic and can generate heat, which limits their application in biomedicine. Therefore, an organic crystal that can increase the temperature under magnetic field conditions is needed to enhance its photothermal effect. Summary of the invention

[0004] Purpose of the invention: The purpose of the present invention is to provide a benzophenanthrene eutectic material and its application.

[0005] Technical solution: The present invention provides a benzophenanthrene eutectic material, wherein the benzophenanthrene eutectic material is a benzophenanthrene-F4TCNQ eutectic.

[0006] The present invention also provides a method for preparing the above-mentioned benzo[C]phenanthrene eutectic material. The eutectic material is prepared by dissolving F4TCNQ and benzo[C]phenanthrene in organic solvents respectively, mixing the two solvents and then volatilizing the solvents.

[0007] Furthermore, the organic solvent is acetonitrile.

[0008] Furthermore, the mixing ratio of the two solvents is 1:1.

[0009] The present invention also provides the use of the above-mentioned benzophenanthrene eutectic material in the preparation of photothermal imaging agents.

[0010] The present invention also provides the use of the benzophenanthrene eutectic material in the preparation of radioactive imaging agents.

[0011] The present invention also provides the use of the benzophenanthrene eutectic material in the preparation of magnetic imaging agents.

[0012] The present invention also provides the use of the benzophenanthrene eutectic material in preparing a biological tissue depth imaging agent.

[0013] The present invention also provides the use of the above-mentioned benzophenanthrene eutectic material in the preparation of photothermal therapy agents.

[0014] Furthermore, the photothermal therapy agent includes magnetic field responsive photothermal therapy.

[0015] Beneficial effects: Compared with the prior art, the present invention has the following outstanding and significant advantages: when the benzophenanthrene eutectic material of the present invention is used as a photothermal imaging and therapeutic agent, it can produce photothermal phenomena under infrared light excitation, and has obvious response to lasers of different powers, fast heating rate, and high heating rate. In addition, it can visualize the area with higher temperature through the photothermal effect. It also has obvious response to magnetic field, which is conducive to the development of more effective magnetic responsive photothermal therapeutic agents. The material can also be excited in the infrared band, which is helpful for the deep imaging of tumor tissue. The eutectic material can provide new ideas and methods for the research in the field of photothermal and magnetic diagnosis and treatment. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figure 1 Absorption spectra of monomer and terephthalate-F4TCNQ eutectic solid.

[0017] Figure 2 This is the photothermal spectrum of benzophenanthrene-F4TCNQ eutectic at different laser powers of 808nm laser.

[0018] Figure 3 This is the photothermal spectrum of benzophenanthrene-F4TCNQ eutectic at different powers of 1064nm laser.

[0019] Figure 4 The benzophenanthrene-F4TCNQ eutectic was exposed to 808nm laser (1.6W / cm 2 ) and 1064nm(0.60W / cm 2 )Photothermal imaging image under laser.

[0020] Figure 5 (a) shows the temperature rise of the eutectic under different powers of 808nm laser irradiation and the change of magnetic field, (b) shows the temperature rise of the eutectic under 808nm laser (1.6W / cm 2 ) under irradiation, the temperature changes with the switching magnetic field. DETAILED DESCRIPTION

[0021] The technical solution of the present invention is further described below in conjunction with the accompanying drawings.

[0022] The testing instrument for the absorption spectrum is a UV-visible spectrophotometer; the photothermal imaging device used is a photothermal imager.

[0023] Example 1. Synthesis of benzophenanthrene eutectic material

[0024] Use acetonitrile to prepare 2mM benzophenanthrene and F4TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanodimethyl-p-benzoquinone), mix the two solvents in equal proportions, and prepare an organic eutectic (dark black solid) by a slow reaction method. The synthesis route is as follows:

[0025]

[0026] Example 2 Eutectic Absorption Spectrum Test Experiment

[0027] Weigh 40 mg of benzophenanthrene, F4TCNQ and benzophenanthrene-F4TCNQ cocrystal, and collect the UV-visible absorption spectra at 200-2500 nm. Figure 1 .

[0028] from Figure 1 It can be seen that the absorbance of benzo[C]phenanthrene and F4TCNQ at 200-2500nm is weak, while the absorbance of benzo[C]phenanthrene-F4TCNQ cocrystal is strong before 1800nm. The absorbance of benzo[C]phenanthrene-F4TCNQ cocrystal is about 4 times that of benzo[C]phenanthrene and F4TCNQ at 808nm and 1064nm, which indicates that the absorption efficiency of benzo[C]phenanthrene-F4TCNQ cocrystal for 808nm and 1064nm laser is stronger than that of benzo[C]phenanthrene and F4TCNQ, which helps the cocrystal to produce photothermal effect under illumination conditions.

[0029] Example 3 Photothermal test experiment of eutectic under 808nm infrared light excitation with different powers

[0030] Weigh 40 mg of benzophenanthrene-F4TCNQ eutectic and irradiate the eutectic with 808 nm laser. Adjust the laser power to 0.4 mW / cm 2 , 0.7mW / cm 2 , 1.3mW / cm 2 、1.6mW / cm 2 , and then measured the temperature of the eutectic when it was periodically turned on and off at different powers. The results are shown in Figure 2 .

[0031] The results show that the organic eutectic has a 2The temperature can be raised to 55℃ ( Figure 2 (a)); at 0.7 mW / cm 2 The temperature can be raised to 70℃ under laser power ( Figure 2 (b)); at 1.3 mW / cm 2 The temperature can be raised to about 110℃ under laser power ( Figure 2 (c)); at 1.6 mW / cm 2 The temperature can be raised to 140℃ under laser power ( Figure 2 (d)). It can be seen from the figure that the organic eutectic has a fast heating rate and a high heat generation temperature, which helps to quickly eliminate tumor tissue. In addition, the degree of temperature rise of the organic eutectic at different powers does not change much, indicating that it has strong stability.

[0032] Example 4 Photothermal test experiment of eutectic under 1064nm infrared light excitation with different powers

[0033] Weigh 40 mg of benzophenanthrene-F4TCNQ eutectic and irradiate the eutectic with a 1064 nm laser. Adjust the laser power to 0.2 mW / cm 2 , 0.3mW / cm 2 , 0.4mW / cm 2 , 0.5mW / cm 2 , 0.6mW / cm 2 , and then measured the temperature of the eutectic when it was periodically turned on and off at different powers. The results are shown in Figure 3 .

[0034] in, Figure 3 The different colored curves in the figure represent the eutectic temperature at different laser powers. 2 Under the power, the temperature of the eutectic can be raised to 145°C, and the organic eutectic can reach the highest temperature in a short time, which shows that the organic eutectic has the characteristics of fast heating rate and high temperature rise, which is helpful to quickly eliminate tumor tissue, and the excitation of infrared band (1064nm) laser is helpful for deep imaging of biological tissue. In addition, in the periodic test of the eutectic under different power irradiation, the degree of temperature rise does not change much, indicating that the organic eutectic can still maintain stable existence at different temperatures in this laser band.

[0035] Example 5 Photothermal imaging experiment of eutectic under different excitation light

[0036] Weigh 40 mg of benzophenanthrene-F4TCNQ eutectic and irradiate the eutectic with 808 nm or 1064 nm laser, adjusting the laser power to 1.6 W / cm 2 and 0.6mW / cm 2Then the photothermal image of the eutectic during the heating process was observed. Figure 4 .

[0037] in, Figure 4 (a) Organic eutectic under 808nm laser (1.6mW / cm 2 ) at different time points. It can be seen from the figure that at this power, the eutectic can quickly heat up to 141°C. (b) Under 1064nm laser (0.6mW / cm 2 ) at different time points under irradiation. It can be seen from the figure that at this power, the eutectic can quickly heat up to 145°C. This shows that the organic eutectic can be used for photothermal imaging, and under 1064nm laser irradiation, the heat generation efficiency of the organic eutectic is higher. Compared with 808nm laser, 1064nm laser can heat up to the highest temperature in a short time at a lower power, which is helpful for photothermal imaging of biological tissues and rapid ablation of tumor tissues.

[0038] Example 6 Photothermal performance test experiment of eutectic under different excitation light

[0039] Weigh 40 mg of benzophenanthrene-F4TCNQ cocrystal and irradiate the cocrystal with 808 nm laser. 2 , 0.7mW / cm 2 、1.0mW / cm 2 , 1.3mW / cm 2 、1.6mW / cm 2 ) add a magnetic field, and then measure the temperature rise and magnetic field strength curves of the eutectic at different powers. Figure 5 a. To prove that the magnetic field has a temperature-raising effect on the synthesized eutectic, the temperature-time curves in the presence and absence of the magnetic field were tested. Figure 5 b.

[0040] in, Figure 5 (a) shows the temperature of the organic eutectic under different powers of 808nm laser irradiation and the change of magnetic field. It can be seen from the figure that the magnetic field has a heating effect on the synthesized eutectic. (b) shows the temperature of the organic eutectic under different powers of 808nm laser irradiation and the change of magnetic field. 2 ) Photothermal temperature curve of switching magnetic field under irradiation. As can be seen from the figure, the magnetic field can increase the photothermal temperature of the synthesized eutectic. This shows that the magnetic field can be increased to increase the photothermal temperature of the synthesized eutectic, which helps to quickly eliminate tumor tissue.

[0041] As described above, although the present invention has been shown and described with reference to specific preferred embodiments, it should not be construed as limiting the present invention itself. Various changes in form and details may be made without departing from the spirit and scope of the present invention as defined in the appended claims.

Claims

1. A benzophenanthrene eutectic material, characterized in that: The benzophenanthrene eutectic material is benzophenanthrene-F4TCNQ eutectic.

2. The method for preparing the benzophenanthrene eutectic material according to claim 1, characterized in that: The eutectic material is prepared by dissolving F4TCNQ and benzophenanthrene in organic solvents respectively, mixing the two solvents and then volatilizing the solvents.

3. The preparation method according to claim 2, characterized in that: The organic solvent is acetonitrile.

4. The preparation method according to claim 2, characterized in that: The mixing ratio of the two solvents is 1:

1.

5. Use of the benzophenanthrene eutectic material according to claim 1 in the preparation of photothermal imaging agents.

6. Use of the benzophenanthrene eutectic material according to claim 1 in the preparation of radioactive imaging agents.

7. Use of the benzophenanthrene eutectic material according to claim 1 in the preparation of magnetic imaging agents.

8. Use of the benzophenanthrene eutectic material according to claim 1 in the preparation of biological tissue depth imaging reagents.

9. Use of the benzophenanthrene eutectic material according to claim 1 in the preparation of photothermal therapy agents.

10. The use according to claim 9, characterized in that: The photothermal therapy agent includes magnetic field responsive photothermal therapy.

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