CN112057617B - Preparation method of core-shell structured porphyrin MOFs/scintillator composite nano material, product and application thereof - Google Patents
Preparation method of core-shell structured porphyrin MOFs/scintillator composite nano material, product and application thereof Download PDFInfo
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Abstract
The invention relates to a preparation method of porphyrin MOFs/scintillator composite nano-material with a core-shell structure, which comprises the steps of firstly preparing NaLuF4Gd is Eu scintillator, carboxyl modification is carried out by 3- (3, 4-dihydroxyphenyl) propionic acid, MESO-tetra (4-carboxyphenyl) porphyrin solution and zirconium chloride solution dispersion are added for reaction to generate Sc @ ZrTCPP, and finally, dicarboxyl polyethylene glycol solution is added for surface modification. The preparation method is simple, the reaction conditions are not harsh, and the obtained porphyrin MOFs/scintillator composite nano material with the core-shell structure is suitable for X-ray-induced radiotherapy/photodynamic combined treatment to promote tumor cell apoptosis and delay the tumor growth speed. The system can maintain the photosensitive activity of porphyrin, improve the stability of porphyrin, overcome the problem of poor penetration depth of the traditional photodynamic therapy and improve the treatment effect of deep solid tumors.
Description
Technical Field
The invention belongs to the technical field of metal organic framework nano materials, and relates to a preparation method of a core-shell structured porphyrin MOFs/scintillator composite nano material, and a product and application thereof.
Background
Photodynamic therapy (PDT) has been a long-standing advance in cancer therapy as a non-invasive treatment. In photodynamic therapy, photosensitizers are excited by light of a specific wavelength to produce reactive oxygen species that are cytotoxic. However, photosensitizers such as porphyrins, which are typically excited by ultraviolet or visible light, have poor penetration properties, impairing the killing of deep tumors by photodynamic therapy.
To solve this problem, a method of exciting a photosensitizer with X-rays (X-PDT) has been developed because X-rays have a stronger tissue penetrating power. X-PDT utilizes a scintillator material to convert X-ray photons downward into visible light to excite a nearby photosensitizer to produce singlet oxygen, thereby triggering PDT. The X-ray induced photodynamic therapy (RDT) combines the advantages of Radiotherapy (RT) and PDT, and has wide application prospect in the treatment of solid tumors in the deep layer of an organism. However, how to combine the nano-scintillator with photosensitizer organically and efficiently to improve the effect of X-ray guided RT/RDT still remains a great problem.
Metal-organic frameworks (MOFs) materials are a class of ordered, porous, crystalline materials formed by covalent coordination of metal ions (clusters) and organic ligands. Not only has very high porosity and surface area, but also has strong controllability of the skeleton structure, and is easy to realize functionalization. In recent years, the nanometer photosensitizer porphyrin-like metal organic framework Materials (MOFs) has attracted more and more attention in the field of photodynamic therapy. The MOFs nano photosensitizer is formed by combining porphyrin ligands and metal ions through coordination bonds, so that the MOFs nano photosensitizer has higher photosensitizer loading rate, enhances the stability of the MOFs nano photosensitizer and solves the problems of reduced photosensitive activity and the like caused by self aggregation. Meanwhile, the pore channels of the MOFs can promote the diffusion of Reactive Oxygen Species (ROS), so that the PDT curative effect is enhanced. Therefore, the organic combination of the nano-scintillator and the porphyrin-like MOFs to construct a novel RT/RDT system is a problem to be solved urgently.
Disclosure of Invention
In view of the above, the present invention provides a preparation method of a novel core-shell structured porphyrin MOFs/scintillator composite nanomaterial, and also provides a core-shell structured porphyrin MOFs/scintillator composite nanomaterial obtained by the preparation method, which can improve the problem of poor penetration depth of the existing PDT, maintain the photosensitive activity of porphyrin, and improve the stability of porphyrin.
In order to achieve the purpose, the invention provides the following technical scheme:
1. the preparation method of the core-shell structured porphyrin MOFs/scintillator composite nano material specifically comprises the following steps:
1) preparation of a scintillator: lu (NO)3)3·6H2O solution, Gd (NO)3)3·6H2O solution, Eu (NO)3)3·6H2Mixing the solution O uniformly, and marking as a solution A; mixing oleic acid and absolute ethyl alcohol, adding a NaOH solution, and uniformly mixing and stirring; then dropwise adding the solution A, and continuously stirring uniformly; adding NaF solution, and continuously stirring uniformly; reacting for 8-12 h at 180-200 ℃; centrifuging the product, and washing the solid with an organic solvent for later use, and recording as Sc NPS;
2) carboxyl modified Sc: dispersing Sc NPS in tetrahydrofuran, then adding the Sc NPS into a tetrahydrofuran solution of 3- (3, 4-dihydroxyphenyl) propionic acid, and reacting the mixed solution at 50-70 ℃ for 3-5 h; cooling to room temperature after the reaction is finished, and adding NaOH solution; centrifuging the product, washing the solid with an organic solvent, and dispersing the solid in a mixed solution of N, N-dimethylformamide and ethanol for later use, and marking as a solution B;
3) preparing Sc @ ZrTCPP: dropwise adding the MESO-tetra (4-carboxyphenyl) porphyrin solution into a zirconium chloride solution, performing ultrasonic dispersion, dropwise adding the solution into the solution B, and reacting for 2-4 h at 120-150 ℃; centrifuging the product, washing the solid with an organic solvent, and dispersing in DMF for later use, and marking as a solution C;
4) surface modification of Sc @ ZrTCPP: dropwise adding the dicarboxy polyethylene glycol solution into the solution C, and stirring the mixed solution for more than 24 hours; centrifuging the product, washing the solid with organic solvent and drying.
Further, Lu (NO) in step 1) of the preparation method3)3·6H2O、Gd(NO3)3·6H2O、Eu(NO3)3·6H2The quantitative ratio of O and NaF reaction substances is 7.5: 2: 0.5: 0.08.
further, the reaction at 180-200 ℃ in step 1) of the preparation method is a solvothermal reaction.
Further, in the step 2) of the preparation method, the mass ratio of Sc NPS to 3- (3, 4-dihydroxyphenyl) propionic acid is 3: 4-6.
Further, in the step 2) of the preparation method, the volume ratio of the mixed solution of N, N-dimethylformamide and ethanol is DMF: EtOH is a 1:3 mixture.
Further, the concentration of the MESO-tetra (4-carboxyphenyl) porphyrin solution in the step 3) of the preparation method is 1-1.2 mg/ml; the concentration of the zirconium chloride solution is 1-1.2mg/ml, and the solution solvent is a mixed solution of N, N-dimethylformamide and ethanol.
Further, the solvent of the solution is DMF: mixed solution of EtOH 1:3
Further, in step 3) of the preparation method, the mass ratio of MESO-tetrakis (4-carboxyphenyl) porphyrin to zirconium chloride is 4-6: 12.
further, the concentration of the MESO-tetrakis (4-carboxyphenyl) porphyrin solution is 1 to 2 mg/ml.
2. The core-shell structured porphyrin MOFs/scintillator composite nano-material product prepared by any one of the preparation methods.
3. Application of core-shell structured porphyrin MOFs/scintillator composite nano-material products in preparation of products for treating tumors.
The invention has the beneficial effects that: animal experiments show that compared with a control group, the obtained core-shell structured porphyrin MOFs/scintillator composite nanomaterial greatly enhances the photodynamic effect, promotes cancer cell apoptosis and reduces the growth rate of tumors. The problem of poor penetration depth of the existing PDT is solved, the photosensitive activity of porphyrin is kept, and the stability of the porphyrin is improved. The practical application of MOFs in tumor treatment can be promoted.
Drawings
In order to make the object, technical scheme and beneficial effect of the invention more clear, the invention provides the following drawings for explanation:
FIG. 1 is a transmission electron micrograph of Sc-COOH NPs and Sc @ ZrTCPP, where A is Sc-COOH NPs and B is Sc @ ZrTCPP.
FIG. 2 is a Sc @ ZrTCPP element surface distribution diagram.
FIG. 3 is a graph of the tumor growth of GL261 tumor mice under various treatment conditions.
FIG. 4 is a graph of the staining of live and dead cells of GL261 under different treatment conditions.
Detailed Description
Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the accompanying drawings. The experimental procedures, in which specific conditions are not specified in the examples, are generally carried out under conventional conditions or under conditions recommended by the manufacturers.
Example 1
1、NaLuF4Preparation of Gd, Eu scintillator (Sc)
①1.5ml 0.5M Lu(NO3)3·6H2O solution, 0.4ml 0.5M Gd (NO)3)3·6H2O solution, 0.25ml of 0.2M Eu (NO)3)3·6H2Mixing the solution O uniformly, and marking as a solution A;
② 5ml of oleic acid is mixed with 10ml of absolute ethyl alcohol, then 1.5ml of solution containing 0.3g of NaOH is added, and the mixture is mixed and stirred for 10 min; dropwise adding the solution A, and continuously stirring for 15 min;
③ 2ml of solution containing 4mmol of NaF is added into the solution II and stirred for 15 min;
fourthly, transferring the mixed solution in the third step to a reaction kettle, and reacting for 8 hours at 180 ℃;
fifthly, centrifuging the product (marked as Sc NPS), and washing the product with ethanol for three times for standby.
2. Carboxyl modified Sc (Sc-COOH)
Dispersing 30mg of Sc NPS in 2ml of tetrahydrofuran, then adding the Sc NPS into 8ml of tetrahydrofuran solution containing 50mg of 3- (3, 4-dihydroxyphenyl) propionic acid, and reacting the mixed solution at 50 ℃ for 3 hours;
② cooling the reaction solution to room temperature, adding 200 mul of 0.2M NaOH solution;
③ the product Sc NPS-COOH is obtained by centrifugation, washed and precipitated by ethanol for three times, and finally redispersed in 1ml of a mixture of N, N-Dimethylformamide (DMF) and ethanol (EtOH) (volume ratio DMF: EtOH is 1: 3) for later use, and is recorded as Sc NPS-COOH mixture.
3. Preparation of Sc @ ZrTCPP
Solution B: 12mg of zirconium chloride (ZrCl)4) Dissolved in 12ml DMF EtOH ═ 1:3 in the mixed solution; solution C: 4.5mg of MESO-tetrakis (4-carboxyphenyl) porphyrin (TCPP) was dissolved in 4ml of a mixture of DMF: EtOH 1: 3;
dropwise adding the solution C into the solution B, ultrasonically dispersing for 5min, then dropwise adding the Sc NPS-COOH mixed solution obtained in the step 2, and finally reacting the mixed solution at 120 ℃ for 2 h; in the step, the solution C is dropwise added into the solution B, so that the uniformity of the product is favorably controlled; the reaction temperature cannot be too high, is controlled to be 120-130 ℃, and the reaction time can be prolonged;
③ the product is obtained by centrifugation and washed three times with DMF, and the product is redispersed in 1ml DMF.
4. Sc @ ZrTCPP surface modification
Dissolving 10mg of dicarboxyl polyethylene glycol (HOOC-PEG-COOH) in 10ml of DMF, then dropwise adding the product obtained in the step 3, and stirring the mixed solution for 24 hours; the water solubility of the product can be further improved;
② centrifuging the product, washing the product for 3 times by using ethanol, finally drying the product in vacuum to obtain the product, and displaying the size of the product to be about 60-80nm by a transmission electron microscope picture.
FIG. 1 is a transmission electron micrograph of Sc-COOH NPs and Sc @ ZrTCPP, where A is Sc-COOH NPs and B is Sc @ ZrTCPP. FIG. 2 is a Sc @ ZrTCPP element surface distribution diagram.
Example 2
1、NaLuF4Preparation of Gd, Eu scintillator (Sc)
①6ml 0.5M Lu(NO3)3·6H2O solution, 2.5ml of 0.5M Gd (NO)3)3·6H2O solution, 1ml of 0.2M Eu (NO)3)3·6H2Mixing the solution O uniformly, and marking as a solution A;
② 20ml of oleic acid is mixed with 40ml of absolute ethyl alcohol, then 6ml of solution containing 0.3g of NaOH is added, and the mixture is mixed and stirred for 20 min; dropwise adding the solution A, and continuously stirring for 20 min;
③ adding 10ml of NaF solution containing 4mmol into the mixture, and continuing stirring for 15 min;
fourthly, transferring the mixed solution in the third step to a reaction kettle, and reacting for 8 hours at 200 ℃;
fifthly, centrifuging the product (marked as Sc NPS), and washing the product with ethanol for three times for standby.
2. Carboxyl modified Sc (Sc-COOH)
Dispersing 100mg of Sc NPS in 8ml of tetrahydrofuran, then adding the Sc NPS into 30ml of tetrahydrofuran solution containing 200mg of 3- (3, 4-dihydroxyphenyl) propionic acid, and reacting the mixed solution at 50 ℃ for 3 hours;
② cooling the reaction solution to room temperature, adding 800 mul of 0.2M NaOH solution;
③ the product Sc NPS-COOH is obtained by centrifugation, washed and precipitated by ethanol for three times, and finally redispersed in 5ml of a mixture of N, N-Dimethylformamide (DMF) and ethanol (EtOH) (volume ratio DMF: EtOH ═ 1: 3) for later use, and recorded as Sc NPS-COOH mixture.
3. Preparation of Sc @ ZrTCPP
Solution B: 50mg of zirconium chloride (ZrCl)4) Dissolved in 50ml DMF EtOH ═ 1:3 in the mixed solution; solution C: 18mg of MESO-tetrakis (4-carboxyphenyl) porphyrin (TCPP) was dissolved in 16ml of a mixture of DMF: EtOH 1: 3;
dropping the solution C into the solution B dropwise, performing ultrasonic dispersion for 5min, then dropping the Sc NPS-COOH mixed solution obtained in the step 2, and finally reacting the mixed solution at 120 ℃ for 4 h; in the step, the solution C is dropwise added into the solution B, so that the uniformity of the product is favorably controlled; the reaction temperature cannot be too high, is controlled to be 120-130 ℃, and the reaction time can be prolonged;
③ the product is obtained by centrifugation and washed three times with DMF, and the product is redispersed in 5ml DMF.
4. Sc @ ZrTCPP surface modification
Dissolving 40mg of dicarboxyl polyethylene glycol (HOOC-PEG-COOH) in 40ml of DMF, then dropwise adding the product obtained in the step 3, and stirring the mixed solution for 24 hours; the water solubility of the product can be further improved;
② the product is obtained by centrifugation, and is washed 3 times by ethanol, and finally the product is obtained by vacuum drying.
Example 3
The detection method comprises the following steps: GL261 was collected at logarithmic growth phase and Balb/c-nu/nu mice (1X 10) were injected subcutaneously6Only), the volume of the tumor to be treated is about 100mm2Then, tumor-bearing mice were randomly divided into four groups: 1) PBS; 2) PBS + X-ray; 3) ScM, respectively; 4) ScM + X-ray, 6 per group, of which 1) and 2) groups were each injected with 50. mu.L of PBS as a control, 3) and 4) groups were irradiated with 2Gry after intratumoral injection of ScM (referring to the final product prepared in example 1) 12.5mg kg-1, 24h, followed by measurement of tumor size every two days and according to the formula 1/2 length X width2The volume is calculated. FIG. 3 is a graph of the tumor growth curves of GL261 tumor mice under different treatment conditions. As shown in the figure, compared with a control, the result shows that the Sc @ ZrTCPP prepared by the invention greatly enhances the photodynamic effect, promotes the apoptosis of cancer cells, reduces the growth speed of tumors and develops a new way for treating the tumors.
Example 4
Cells GL261 from logarithmic growth phase were plated in 2 12-well plates, 8X 104Culturing in a 5% CO2 incubator at 37 deg.C for 24 hr; ScM treated cells were added at a final concentration of 50ug/mL for 8h while an untreated group was set up; irradiating one plate with 6Gry, washing cells with PBS, replacing fresh culture medium, and culturing for 24 h; the plate medium was discarded, cells were washed with PBS, and then stained with 200uL of Calcein AM/PI staining solution per well (10 uL of Calcein AM and 15uL of PI in 5mL of PBS) at 37 ℃ for 15min, and photographed in a fluorescence/confocal microscope. The cell status of each treatment group is shown in FIG. 4. As can be seen from the figure, the untreated group had substantially no apoptosis after being irradiated with Xray, and a small amount of apoptosis was observed after ScM-treated cells were added, and the number of apoptosis was significantly increased after being irradiated with Xray.
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, although the invention has been described in detail with reference to the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the scope of the invention as defined by the appended claims.
Claims (10)
1. The preparation method of the core-shell structured porphyrin MOFs/scintillator composite nano material is characterized by comprising the following steps:
1) flashingPreparation of the body: lu (NO)3)3·6H2O solution, Gd (NO)3)3·6H2O solution, Eu (NO)3)3·6H2Mixing the solution O uniformly, and marking as a solution A; mixing oleic acid and absolute ethyl alcohol, adding a NaOH solution, and uniformly mixing and stirring; then dropwise adding the solution A, and continuously stirring uniformly; adding NaF solution, and continuously stirring uniformly; reacting for 8-12 h at 180-200 ℃; centrifuging the product, and washing the solid with an organic solvent for later use, and recording as Sc NPS;
2) carboxyl modified Sc: dispersing Sc NPS in tetrahydrofuran, then adding the Sc NPS into tetrahydrofuran solution containing 3- (3, 4-dihydroxyphenyl) propionic acid, and reacting the mixed solution at 50-70 ℃ for 3-5 h; cooling to room temperature after the reaction is finished, and adding NaOH solution; centrifuging the product, washing the solid with an organic solvent, and dispersing the solid in a mixed solution of N, N-dimethylformamide and ethanol for later use, and marking as a solution B;
3) preparing Sc @ ZrTCPP: dropwise adding the MESO-tetra (4-carboxyphenyl) porphyrin solution into a zirconium chloride solution, performing ultrasonic dispersion, dropwise adding the solution into the solution B, and reacting for 2-4 h at 120-130 ℃; centrifuging the product, washing the solid with an organic solvent, and dispersing in DMF for later use, and marking as a solution C;
4) surface modification of Sc @ ZrTCPP: dropwise adding the dicarboxy polyethylene glycol solution into the solution C, and stirring the mixed solution for more than 24 hours; centrifuging the product, washing the solid with organic solvent and drying.
2. The preparation method of the core-shell structured porphyrin MOFs/scintillator composite nanomaterial according to claim 1, wherein Lu (NO) is adopted in step 1) of the preparation method3)3·6H2O、Gd(NO3)3·6H2O、Eu(NO3)3·6H2The quantitative ratio of O and NaF reaction substances is 7.5: 2: 0.5: 0.08.
3. the preparation method of the core-shell structured porphyrin MOFs/scintillator composite nanomaterial according to claim 1, wherein the reaction in step 1) is a solvothermal reaction at 180-200 ℃.
4. The preparation method of the core-shell structured porphyrin MOFs/scintillator composite nanomaterial according to claim 1, wherein the mass ratio of Sc NPS to 3- (3, 4-dihydroxyphenyl) propionic acid in the step 2) of the preparation method is 3: 4-6.
5. The preparation method of the core-shell structured porphyrin MOFs/scintillator composite nanomaterial according to claim 1, wherein in the step 2) of the preparation method, a mixed solution of N, N-dimethylformamide and ethanol is DMF (dimethyl formamide): EtOH is a 1:3 mixture.
6. The preparation method of the core-shell structured porphyrin MOFs/scintillator composite nanomaterial according to claim 1, wherein in step 3) of the preparation method, the concentration of the MESO-tetrakis (4-carboxyphenyl) porphyrin solution is 1-1.2 mg/ml; the concentration of the zirconium chloride solution is 1-1.2mg/ml, and the solution solvent is a mixed solution of N, N-dimethylformamide and ethanol.
7. The preparation method of the core-shell structured porphyrin MOFs/scintillator composite nanomaterial according to claim 1, wherein in step 3) of the preparation method, the mass ratio of MESO-tetra (4-carboxyphenyl) porphyrin to zirconium chloride is 4-6: 12.
8. the preparation method of the core-shell structured porphyrin MOFs/scintillator composite nanomaterial according to claim 1, wherein the concentration of the MESO-tetrakis (4-carboxyphenyl) porphyrin solution is 1-2 mg/ml.
9. The product obtained by the preparation method of the core-shell structured porphyrin MOFs/scintillator composite nanomaterial according to any one of claims 1 to 8.
10. Use of a product according to claim 9 for the preparation of a product for the treatment of tumors.
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