Tetramethylpiperidine oxide functionalized metalloporphyrin nanoparticles as well as preparation method and application thereof
Through Tempol functional modification, efficient metalporphyrin nanoparticles were prepared, which solved the shortcomings of existing materials in water solubility, imaging performance, ROS removal capability and visual monitoring, and achieved efficient ROS removal and accurate therapeutic effects.
Patent Information
- Application Number
- CN202510297885.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-03-13
- Publication Date
- 2025-06-13
AI Technical Summary
Existing metalporphyrin nanomaterials have shortcomings in water solubility, imaging performance, ROS clearance capability and visual monitoring of ROS clearance processes, resulting in blurred treatment decisions and risk of excessive intervention.
Through functional modification, Tempol functionalized metalporphyrin nanoparticles were prepared, and a simple and efficient preparation method was adopted to improve their water dispersion, MRI imaging performance and ROS removal efficiency, and a diagnosis and treatment integrated material was constructed to achieve visual chemotherapy effect monitoring.
It improves the chelation stability and imaging performance of metalporphyrin nanoparticles, enhances ROS clearance, ensures the accuracy and safety of treatment, and avoids the risks of fuzzy treatment decisions and excessive intervention.
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Figure CN120131946A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the field of medicine, and specifically to a preparation method and application of a multifunctional metal porphyrin nanoparticle. Background Art
[0002] Theranostics integration is an important development direction in the field of biomedicine in recent years. By integrating diagnostic and therapeutic functions into a single material or system, it can achieve real-time monitoring and precise intervention of diseases, significantly improving the treatment efficiency. Compared with the traditional diagnosis and treatment separation mode, the theranostics integration technology can dynamically optimize the treatment plan, reduce repeated examinations and over-medical treatment. At the same time, it can track the drug distribution and efficacy through visualization means, providing technical support for personalized medicine. Especially in complex pathological scenarios such as tumors, cardiovascular diseases and inflammation, materials with both imaging and therapeutic functions can simultaneously complete lesion localization, efficacy evaluation and targeted treatment, thus shortening the diagnosis and treatment cycle and improving the prognosis of patients. However, existing theranostics integration materials still face challenges such as insufficient functional integration, limited biocompatibility and low multimodal synergistic efficiency, and there is an urgent need to develop new multifunctional nanoplatforms to meet clinical needs.
[0003] Reactive oxygen species (ROS), as key molecules in the occurrence and development of various diseases, play important roles in tumor microenvironment regulation, inflammatory cascade reactions and tissue oxidative damage. Studies have shown that scavenging excessive ROS can effectively alleviate the pathological process, such as reducing ischemia-reperfusion injury and delaying the deterioration of neurodegenerative diseases. However, existing ROS scavenging strategies still have obvious limitations: on the one hand, small molecule antioxidants are prone to rapid degradation and poor targeting, resulting in low scavenging efficiency; on the other hand, ROS scavengers based on nanomaterials often face problems such as complex preparation processes and poor chelation stability of metal ions. More prominently, most scavengers lack real-time efficacy feedback functions and cannot dynamically monitor changes in ROS levels, resulting in difficult-to-precisely control treatment doses and prone to over-intervention or insufficient efficacy. Therefore, developing intelligent nanomaterials with both high-efficiency ROS scavenging ability and multimodal imaging functions has become the key path to breaking through the bottleneck of theranostics integration.
[0004] Metal porphyrin is a functional nanomaterial with both multimodal imaging and ROS scavenging abilities, showing great potential in cancer diagnosis and treatment. However, metal porphyrin has the following key limitations: first, poor water solubility affects its stability and imaging performance in vivo; second, its ROS scavenging ability has not been fully exerted and needs to be enhanced through functional modification; finally, there is a lack of effective visualization monitoring means during the ROS scavenging process, leading to ambiguous treatment decisions and risks of over-intervention.
[0005] In view of the above reasons, the present invention is specifically proposed. Summary of the Invention
[0006] The object of the present invention is to overcome the deficiencies of the prior art, meet the actual needs, and provide a kind of tempol-functionalized metal porphyrin nanoparticles, a preparation method and an application thereof. The tempol-functionalized metal porphyrin nanoparticles of the present invention have high chelation stability, imaging performance and reactive oxygen species scavenging ability, and the preparation method is simple, efficient and has greater potential for clinical transformation. The present invention aims to solve the problems in the prior art such as poor water solubility of metal porphyrin, poor imaging performance, insufficient ROS scavenging ability and lack of effective visualization monitoring means for the ROS scavenging process, so as to avoid the ambiguity of treatment decisions and the risk of over-intervention.
[0007] In order to achieve the object of the present invention, the technical scheme adopted by the present invention is as follows:
[0008] The first object of the present invention provides a kind of tempol-functionalized metal porphyrin nanoparticles, and the chemical formula of the tempol-functionalized metal porphyrin nanoparticles is shown in Formula I:
[0009]
[0010] The second object of the present invention provides a preparation method of the tempol-functionalized metal porphyrin nanoparticles, which comprises the following steps: mixing a metal porphyrin derivative, 1-ethyl-(3-dimethylaminopropyl)carbodiimide, N-hydroxysuccinimide, PEG and tempol, reacting in N,N-dimethylformamide, dialyzing successively with N,N-dimethylformamide and water, and freeze-drying to obtain the tempol-functionalized metal porphyrin polymer.
[0011] Further, the porphyrin derivatives in the tempol-functionalized metal porphyrin nanoparticles include tetracarboxyphenyl porphyrin, tetraaminophenyl porphyrin, tetraaldehydephenyl porphyrin, tetrahydroxyphenyl porphyrin, etc. The metal ions in the metal porphyrin derivatives are selected from at least one of paramagnetic metal ions, radioactive metal ions and lanthanide luminescent metal ions. The paramagnetic metal ions include Gd 3+ , Mn 2+ or Fe 3+ , the radioactive metal ions include 64 Cu, 68 Ga, 89 Zr or 99 Tc, and the lanthanide luminescent metal ions include Tb, Nd or Eu.
[0012] Further, the molar ratio of the metal porphyrin derivative, 1-ethyl-(3-dimethylaminopropyl)carbodiimide, N-hydroxysuccinimide, PEG and tempol is 1:1:1:1-10.
[0013] Further, the reaction sequence is as follows: after the metal porphyrin derivative, 1-ethyl-(3-dimethylaminopropyl)carbodiimide, N-hydroxysuccinimide, and PEG are mixed and reacted, the excess unreacted reactants are removed by dialysis, freeze-dried, and then the above product is mixed and reacted with 1-ethyl-(3-dimethylaminopropyl)carbodiimide, N-hydroxysuccinimide, and Tempol.
[0014] Further, the reaction temperature is 20 - 60 °C, and the reaction time is 1 - 5 days.
[0015] Further, the dialysis is carried out by first dialyzing with N,N-dimethylformamide for 3 days and then with distilled water for 3 days.
[0016] The third object of the present invention provides a method for preparing Tempol-functionalized metal porphyrin nanoparticles, which is characterized by including the following steps: dissolving the Tempol-functionalized metal porphyrin polymer in an organic reagent, and under the condition of room temperature and with the assistance of probe sonication, dropping it into a distilled water solution, dialyzing to remove unassembled molecules and solvents, and rotary evaporating and concentrating to obtain the Tempol-functionalized metal porphyrin nanoparticles.
[0017] Further, the organic reagent is N,N-dimethylformamide, dimethyl sulfoxide, methanol, ethanol, chloroform, or acetone.
[0018] Further, the concentration of the Tempol-functionalized metal porphyrin nanoparticles is 0.1 - 100 mg / mL; the mass ratio of the Tempol-functionalized metal porphyrin polymer to distilled water is 5:100.
[0019] Further, the dialysis medium is deionized water, the dialysis time is 2 - 3 days, and the molecular weight cut-off of the dialysis bag is 3 - 50 kDa.
[0020] The fourth object of the present invention provides an application of the described Tempol-functionalized metal porphyrin nanoparticles in imaging probes and reactive oxygen species scavenging therapy.
[0021] Compared with the prior art, the beneficial effects of the present invention are as follows:
[0022] 1. The Tempol-functionalized metal porphyrin nanoparticles of the present invention have high chelation stability. Functional modification can improve the water dispersibility and in vivo circulation time of metal porphyrins; improve the imaging performance of MRI contrast agents; improve the ROS scavenging efficiency; and construct a diagnostic and therapeutic integrated material for visualizing the efficacy monitoring.
[0023] 2. The preparation method of the Tempol-functionalized metalloporphyrin nanoparticles of the present invention is simple, efficient, and has clinical transformation potential, and is extremely promising in the fields of MRI, PET, SPECT, and fluorescence imaging and their integrated diagnosis and treatment research. BRIEF DESCRIPTION OF THE DRAWINGS
[0024] Figure 1 This is a transmission electron microscopy image of the Tempol-functionalized metalloporphyrin nanoparticles prepared in Example 1 of the present invention.
[0025] Figure 2 This is a time-of-flight mass spectrum of the Tempol-functionalized metalloporphyrin nanoparticles prepared in Example 1 of the present invention.
[0026] Figure 3 This is a diagram of the T1 relaxation efficiency of the Tempol-functionalized metal porphyrin nanoparticles prepared in Example 1 of the present invention.
[0027] Figure 4 This is a graph showing the ROS scavenging efficiency of the Tempol-functionalized metalloporphyrin nanoparticles prepared in Example 1 of the present invention.
[0028] Figure 5 The Tempol-functionalized metalloporphyrin nanoparticles prepared in Example 1 of the present invention were used for in vivo cardiac magnetic resonance imaging images of a diabetic cardiomyopathy model. DETAILED DESCRIPTION
[0029] The present invention is further described below in conjunction with the accompanying drawings and embodiments:
[0030] Example 1
[0031] Preparation of Tempol Functionalized Manganese Porphyrin Nanoparticles
[0032] step:
[0033] S1. Carboxyl activation and PEG modification
[0034] 1 mmol tetracarboxylporphyrin manganese (TCPP(Mn)) was dissolved in 10 mL of anhydrous dimethyl sulfoxide, and 0.5 mmol 1-ethyl-(3-dimethylaminopropyl)carbodiimide (EDC) and N-hydroxysuccinimide (NHS) were added in sequence, and magnetic stirring was performed at room temperature for 1 hour to activate the carboxyl group. Subsequently, 0.5 mmol amino-terminated polyethylene glycol (NHS) was added. 2-(mPEG), and continue stirring the reaction for 24 hours. After the reaction is completed, transfer the mixed solution into a dialysis bag with a molecular weight cut-off of 1000 Da, and dialyze it with N,N-dimethylformamide (DMF) for 3 days to remove unreacted TCPP(Mn), EDC, and NHS; then continue to dialyze it with distilled water for 3 days to remove DMF. The product is concentrated by rotary evaporation and then freeze-dried to obtain TCPP(Mn)-PEG.
[0035] S2. Functional modification with Tempol
[0036] Dissolve 1 mmol of TCPP(Mn)-PEG in 10 mL of anhydrous dimethyl sulfoxide, add 10 mmol of EDC and NHS (molar ratio 1:1), and stir at room temperature for 1 hour to activate the carboxyl group twice. Then add 10 mmol of aminotetramethylpiperidine 1-oxyl (NH 2 -Tempol), and continue the reaction for 24 hours. The product is dialyzed with DMF and distilled water for 3 days each in turn, concentrated, and then freeze-dried to obtain Tempol-TCPP(Mn)-PEG.
[0037] S3. Nanoparticle assembly
[0038] Slowly drop 1 mL of the methanol solution of Tempol-TCPP(Mn)-PEG (10 mg / mL) into 10 mL of distilled water at a rate of 1 drop per second, and simultaneously perform self-assembly with the assistance of a probe ultrasonic (power 35 W, on / off cycle 5 s / 5 s). Then remove methanol and excess water by rotary evaporation to obtain Tempol-functionalized manganese porphyrin nanoparticles, and store them at 4 °C for later use.
[0039] The results are as Figure 1 shown, the time-of-flight mass spectrometry results of Tempol-TCPP(Mn)-PEG.
[0040] Example 2
[0041] Preparation of Tempol-functionalized gadolinium porphyrin nanoparticles
[0042] Steps:
[0043] S1. Carboxyl activation and PEG modification
[0044] Dissolve 1 mmol of gadolinium tetracarboxyl porphyrin (TCPP(Gd)) in 10 mL of anhydrous dimethyl sulfoxide, add 0.5 mmol of EDC and NHS in sequence, and stir magnetically at room temperature for 1 hour to activate the carboxyl group. Then add 0.5 mmol of NH 2-mPEG, continue stirring the reaction for 24 hours. Transfer the reaction solution into a dialysis bag with a molecular weight cut-off of 1000 Da, and dialyze with DMF for 3 days to remove unreacted TCPP(Gd), EDC and NHS, then dialyze with distilled water for 3 days to remove DMF. The product is concentrated by rotary evaporation and then freeze-dried to obtain TCPP(Gd)-PEG.
[0045] S2, Tempol functionalization modification
[0046] Dissolve 1 mmol of TCPP(Gd)-PEG in 10 mL of anhydrous dimethyl sulfoxide, add 10 mmol of EDC and NHS (molar ratio 1:1), and stir at room temperature for 1 hour to activate the carboxyl group. Then add 10 mmol of NH 2 -Tempol, continue the reaction for 24 hours. The product is dialyzed with DMF and distilled water for 3 days in turn, concentrated and then freeze-dried to obtain Tempol-TCPP(Gd)-PEG.
[0047] S3, nanoparticle assembly
[0048] Slowly add 1 mL of the methanol solution of Tempol-TCPP(Gd)-PEG (10 mg / mL) drop by drop at a rate of 1 drop per second into 10 mL of distilled water, and at the same time use probe ultrasound (power 35 W, on / off cycle 5 s / 5 s) to assist self-assembly. After removing methanol and excess water by rotary evaporation, Tempol-functionalized gadolinium porphyrin nanoparticles are obtained and stored at 4 °C for later use.
[0049] Example 3
[0050] Preparation of Tempol-functionalized terbium porphyrin nanoparticles
[0051] Steps:
[0052] S1, carboxyl activation and PEG modification
[0053] Dissolve 1 mmol of tetracarboxyl porphyrin terbium (TCPP(Tb)) in 10 mL of anhydrous dimethyl sulfoxide, add 0.5 mmol of EDC and NHS in sequence, and stir magnetically at room temperature for 1 hour to activate the carboxyl group. Then add 0.5 mmol of NH 2 -mPEG, continue stirring the reaction for 24 hours. Transfer the reaction solution into a dialysis bag with a molecular weight cut-off of 1000 Da, and dialyze with DMF for 3 days to remove unreacted TCPP(Tb), EDC and NHS, then dialyze with distilled water for 3 days to remove DMF. The product is concentrated by rotary evaporation and then freeze-dried to obtain TCPP(Tb)-PEG.
[0054] S2, Tempol functionalization modification
[0055] Dissolve 1 mmol of TCPP(Tb)-PEG in 10 mL of anhydrous dimethyl sulfoxide, add 10 mmol of EDC and NHS (molar ratio 1:1), and stir at room temperature for 1 hour to activate the carboxyl group. Subsequently, add 10 mmol of NH 2 -Tempol and continue the reaction for 24 hours. The product is dialyzed against DMF and distilled water for 3 days each in turn, concentrated and then freeze-dried to obtain Tempol-TCPP(Tb)-PEG.
[0056] S3. Nanoparticle assembly
[0057] Slowly drop 1 mL of the methanol solution of Tempol-TCPP(Tb)-PEG (10 mg / mL) into 10 mL of distilled water at a rate of 1 drop per second, and at the same time use probe ultrasound (power 35 W, on / off cycle 5 s / 5 s) to assist self-assembly. After removing methanol and excess water by rotary evaporation, Tempol-functionalized terbium porphyrin nanoparticles are obtained and stored at 4 °C for later use in fluorescence imaging.
[0058] Example 4
[0059] Tempol functionalization 99 Preparation of Tc porphyrin nanoparticles
[0060] Steps:
[0061] Carboxyl activation and PEG modification:
[0062] Dissolve 1 mmol of tetracarboxyl porphyrin (TCPP) in 10 mL of anhydrous dimethyl sulfoxide, and successively add 0.5 mmol of EDC and NHS, and stir magnetically at room temperature for 1 hour to activate the carboxyl group. Subsequently, add 0.5 mmol of NH 2 -mPEG and continue stirring for 24 hours. Transfer the reaction solution to a dialysis bag with a molecular weight cut-off of 1000 Da, dialyze against DMF for 3 days to remove unreacted TCPP, EDC and NHS, and then dialyze against distilled water for 3 days to remove DMF. The product is concentrated by rotary evaporation and then freeze-dried to obtain TCPP-PEG.
[0063] Tempol functionalization modification:
[0064] Dissolve 1 mmol of TCPP-PEG in 10 mL of anhydrous dimethyl sulfoxide, add 10 mmol of EDC and NHS (molar ratio 1:1), and stir at room temperature for 1 hour to activate the carboxyl group. Subsequently, add 10 mmol of NH 2 -Tempol and continue the reaction for 24 hours. The product is dialyzed against DMF and distilled water for 3 days each in turn, concentrated and then freeze-dried to obtain Tempol-TCPP-PEG.
[0065] Nanoparticle assembly and99 Tc Chelation:
[0066] A 1 mL methanol solution of Tempol-TCPP-PEG (10 mg / mL) was slowly added dropwise to 10 mL of distilled water at a rate of 1 drop per second, while probe sonication (power 35 W, on / off cycle 5 s / 5 s) was used to assist self-assembly. After removing methanol and excess water by rotary evaporation, the nanoparticles were stored at 4 °C for later use. Subsequently, the Tempol-TCPP-PEG nanoparticles were chelated with 99 Tc for SPECT imaging.
[0067] Experimental Example 1
[0068] Transmission Electron Microscopy (TEM) Detection of Tempol-TCPP(Mn)-PEG
[0069] An appropriate amount of the dispersion of Tempol-functionalized metal porphyrin nanoparticles was diluted, and 10 μL was dropped onto the surface of a copper grid and dried at room temperature. The sample was placed under a transmission electron microscope for observation and photography. The results are as Figure 1 shown. The crystal nucleus size of the Tempol-functionalized metal porphyrin nanoparticles is in the range of 5 - 10 nanometers.
[0070] Experimental Example 2
[0071] 1. Evaluation of the Relaxation Efficiency of Tempol-TCPP(Mn)-PEG Nanoparticles
[0072] Using a 1.5 T clinical magnetic resonance device (Siemens), the T1 relaxation parameters of the Tempol-functionalized manganese porphyrin nanoparticles prepared in Example 1 were measured by an inversion recovery sequence. The specific steps are as follows: The sample was fixed in the head coil of the magnetic resonance instrument, and the scanning parameters (TE = 11.7 ms, TR = 30 - 3300 ms) were set for gradient echo scanning to obtain T1-weighted images. The measured values were analyzed using data processing software, the T1 relaxation times of samples at different concentrations were calculated, and a linear regression analysis was performed with 1 / T1 (s-1) as the ordinate and the sample concentration (mM) as the abscissa. The slope of the fitted curve is the T1 relaxation efficiency (r 1 , unit: mM-1·s-1). The experimental results show that the T1 relaxation parameters of the Tempol-functionalized manganese porphyrin nanoparticles are significantly improved compared with commercial gadolinium contrast agents.
[0073] 2. Evaluation of the ROS Scavenging Ability of Tempol-TCPP(Mn)-PEG Nanoparticles
[0074] Superoxide Anion (O 2 · -)Scavenging efficiency: Using electron paramagnetic resonance (EPR) spectroscopy, O 2 · - was generated through the xanthine / xanthine oxidase system (10 mM xanthine, 1 U / mL xanthine oxidase), and 100 mM DMPO was used to capture it to form a stable DMPO / ·OOH spin adduct. After adding Tempol-functionalized nanoparticles to the system, the EPR spectrum was recorded, and the results showed that the signal intensity of O 2 · - decreased significantly.
[0075] Hydroxyl radical (·OH) scavenging ability: In PBS buffer (25 mM) at pH 7.4, ·OH was catalytically generated through the Fenton reaction (1 mM Fe 2+ and 4 mM H 2 O 2 ), and DMPO was used as a spin trap to form a DMPO / ·OH adduct. By comparing the EPR spectra of the system without and with Tempol-functionalized nanoparticles (10 μg Mn / mL) added, a significant attenuation of the ·OH signal was observed, indicating its high scavenging ability.
[0076] 3. In vivo cardiac magnetic resonance imaging of Tempol-TCPP(Mn)-PEG nanoparticles
[0077] The Tempol-TCPP(Mn)-PEG nanoparticles prepared in Example 1 (dose: 0.05 mmol Mn / kg) were injected into diabetic cardiomyopathy model mice (body weight ~40 g) through the tail vein to evaluate their in vivo MRI imaging effect. The specific operation is as follows: An indwelling needle was pre-implanted in the model mice, and cardiac MRI images before injection were collected on a 7.0 T MRI; then the nanoparticles were injected through the indwelling needle, and cardiac MRI images were collected again. The results are as Figure 5 shown. After injection, the signal intensity in the myocardial region increased significantly, confirming that the nanoparticles have excellent cardiac magnetic resonance imaging performance.
[0078] In addition, the components designed in the present invention are all common standard components or components known to those skilled in the art. Their structures and principles can all be known by those skilled in the art through technical manuals or through conventional experimental methods. Those skilled in the art can fully implement them without further elaboration. The content protected by the present invention does not involve improvements to the internal structure and method either.
[0079] The embodiments disclosed in the present invention are preferred embodiments, but not limited thereto. Those of ordinary skill in the art can easily understand the spirit of the present invention based on the above embodiments and make different extensions and changes. However, as long as they do not depart from the spirit of the present invention, they are all within the protection scope of the present invention.
Claims
1. A Tempol functionalized metalloporphyrin nanoparticle, characterized in that: The chemical formula of the Tempol functionalized metal porphyrin nanoparticles is shown in Formula I: The metal porphyrin nanoparticles contain porphyrin derivatives and chelated metal ions, and the metal ions are selected from at least one of paramagnetic metal ions, radioactive metal ions or lanthanide luminescent metal ions.
2. The Tempol functionalized metalloporphyrin nanoparticles according to claim 1, characterized in that: The porphyrin derivative in the Tempol functionalized metal porphyrin nanoparticles is selected from one of tetracarboxylphenylporphyrin, tetraaminophenylporphyrin, tetraaldehydephenylporphyrin or tetrahydroxyphenylporphyrin; The paramagnetic metal ion is Gd 3+ , Mn 2+ or Fe 3+ ; The radioactive metal ion is 64 Cu, 68 Ga, 89 Zr or 99 Tc; the lanthanide luminescent metal ion is Tb, Nd or Eu.
3. The method for preparing Tempol functionalized metal porphyrin nanoparticles according to claim 1 or 2, characterized in that: The functionalized molecules include amino-terminated polyethylene glycol (NH2-PEG), carboxyl-terminated polyethylene glycol COOH-PEG, amino-modified Tempol (NH2-Tempol), and carboxyl-modified Tempol COOH-Tempol; The Mw of NH2-PEG and COOH-PEG are both 200-10000.
4. The preparation method according to claim 3, comprising the steps of: S1, mixing a metal porphyrin derivative, 1-ethyl-(3-dimethylaminopropyl)carbodiimide, N-hydroxysuccinimide, PEG, and Tempol, and reacting them in N,N-dimethylformamide; S2, dialyzing with N,N-dimethylformamide and water in sequence, and freeze-drying to obtain the Tempol functionalized metalloporphyrin nanoparticles; S3, dissolving the Tempol functionalized metal porphyrin nanoparticles in an organic reagent, adding the mixture dropwise to a distilled water solution at room temperature with the assistance of probe ultrasound, dialyzing to remove unassembled molecules and solvent, and concentrating by rotary evaporation to obtain the Tempol functionalized metal porphyrin nanoparticles.
5. The preparation method according to claim 4, characterized in that: The molar ratio of the metal porphyrin derivative, 1-ethyl-(3-dimethylaminopropyl)carbodiimide, N-hydroxysuccinimide, and Tempol in S1 is 1:1:1:1-10; The reaction sequence is: metal porphyrin derivative, 1-ethyl-(3-dimethylaminopropyl) carbodiimide, N-hydroxysuccinimide, PEG are mixed and reacted, excess unreacted reactants are removed by permeation, and then freeze-dried, and then the above product is mixed and reacted with 1-ethyl-(3-dimethylaminopropyl) carbodiimide, N-hydroxysuccinimide, and Tempol.
6. The preparation method according to claim 4, characterized in that: The reaction temperature in S1 is 20-60°C and the reaction time is 1-5 days; The dialysis process in S2 includes: first dialysis with N,N-dimethylformamide for 3 days, and then dialysis with distilled water for 3 days.
7. The preparation method according to claim 4, characterized in that: The organic solvent in S3 is N,N-dimethylformamide, dimethyl sulfoxide, methanol, ethanol, chloroform or acetone; The concentration of the Tempol functionalized metal porphyrin polymer in S3 is 0.1-100 mg / mL; the mass ratio of the Tempol functionalized metal porphyrin nanoparticles to distilled water is 5:100; The particle size of the nanoparticles is 5-500nm; The dialysis medium in S2 is deionized water, the dialysis time is 2 to 3 days, and the molecular weight of the dialysis bag is 3-50 kDa.
8. The use of the Tempol functionalized metalloporphyrin nanoparticles in an imaging probe according to claim 1 or 2, characterized in that: The imaging probe is used for at least one of magnetic resonance imaging (MRI), positron emission tomography (PET), single photon emission computed tomography (SPECT), fluorescence imaging or multimodal imaging.
9. The use of Tempol functionalized metalloporphyrin nanoparticles according to claim 1 or 2 in active oxygen scavenging therapy, characterized in that: Used to treat cardiovascular diseases or inflammation-related diseases.
10. The use according to claim 9, characterized in that: The cardiovascular diseases include myocardial infarction, coronary heart disease, atherosclerotic plaques or thrombi; the inflammation-related diseases include diabetic complications, cardiomyopathy, pneumonia, arthritis, Alzheimer's disease or Parkinson's disease.