CN110734762A - near-infrared photosensitizers, and preparation method and application thereof - Google Patents
near-infrared photosensitizers, and preparation method and application thereof Download PDFInfo
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Abstract
The invention belongs to the field of medicines, and discloses near-infrared photosensitizers, and a preparation method and application thereof.
Description
Technical Field
The invention belongs to the field of medicines, and particularly relates to near-infrared photosensitizers, a preparation method thereof, and application thereof in preparation of photodynamic tumor treatment medicines and imaging agents.
Background
The therapy has high specificity, small damage to normal cells and no toxic and side effects of chemotherapy and radiotherapy, so that the therapy has wide prospect .
The photosensitizer is a core drug for photodynamic therapy, can be enriched in tumor cells, can generate photodynamic sensitization reaction under the excitation of light with the wavelength of so as to destroy the tumor cells, can play a role in treatment and also can play a role in fluorescence diagnosis.
The near infrared light has strong tissue penetrability, almost has no damage to cell tissues and has no background fluorescence. However, the energy of near infrared light is low, and the tumor killing effect by photodynamic cannot be generated. The upper conversion luminescence is adopted to convert the near infrared light with lower energy into the visible light with higher energy, so that the near infrared photosensitizer is developed by utilizing the upper conversion luminescent material, and the photodynamic therapy of deep tumors can be realized.
The carbon dots are kinds of fluorescent carbon nano-particles, and compared with the traditional organic dye and semiconductor quantum dots, the carbon dots have the characteristics of low toxicity, good water solubility, good biocompatibility, easy modification, rich and cheap raw materials, good light stability and the like.
Disclosure of Invention
In order to overcome the defects and shortcomings in the prior art, the invention aims to provide near-infrared photosensitizers prepared from carbon dots and pheophorbide.
Another object of of the present invention is to provide a method for preparing the above-mentioned near-infrared photosensitizer.
The invention further aims to to provide the application of the near-infrared photosensitizer in preparing a photodynamic tumor treatment medicament and a tumor cell imaging agent.
The purpose of the invention is realized by the following technical scheme:
near infrared photosensitizer with molecular structure:
The preparation method of the near-infrared photosensitizer specifically comprises the following steps:
1) reacting cinnamaldehyde and urea in an organic solvent at 180-220 ℃ for 6-12 h, centrifuging, dialyzing supernate, and drying to obtain carbon dots;
2) activating the pheophorbide by an activating agent in an organic solvent to obtain activated pheophorbide; dispersing carbon dots in an organic solvent to obtain a carbon dot dispersion liquid; and dripping the carbon dot dispersion liquid into activated pheophorbide, reacting, centrifuging, dialyzing, and drying to obtain the near-infrared photosensitizer.
The molar ratio of the cinnamaldehyde to the urea in the step 1) is 1: 1-3;
the organic solvent in the step 1) is more than of dimethyl sulfoxide, dimethylformamide or tetrahydrofuran;
the dialysis in the step 1) refers to dialysis membrane dialysis with the molecular weight cutoff of 2000-6000 Da;
the mass ratio of the volume of the organic solvent to the mass of the cinnamaldehyde and the urea in the step 1) is (1-20) to 1 (mL/g).
The amount of the carbon points in the step 2) is 1/5-1/10 of the mass of the pheophorbide.
The activating agents in step 2) are EDC (1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride) and NHS (N-hydroxysuccinimide). The dosage of the EDC is 1-3 times of the molar weight of the pheophorbide; the dosage of the NHS is 1-3 times of the molar weight of the pheophorbide.
The reaction condition in the step 2) is room temperature reaction for 12-18 h; the activating condition in the step 2) is room temperature reaction for 20-60 min;
in the step 2), the organic solvent in the activated pheophorbide is more than of dimethyl sulfoxide, dimethyl formamide or tetrahydrofuran, and the organic solvent in the carbon point dispersion liquid is more than of dimethyl sulfoxide, dimethyl formamide or tetrahydrofuran.
The dialysis in the step 2) refers to dialysis membrane dialysis with the molecular weight cutoff of 2000-6000 Da;
the mass ratio of the volume of the organic solvent in the activated pheophorbide to the pheophorbide in the step 2) is (1-20): 1 (mL/g); the mass ratio of the volume of the organic solvent to the carbon dots in the carbon dot dispersion liquid is (1-20) to 1 (mL/g).
The dialysis time in the steps 1) and 2) is 12-48 h respectively;
the drying conditions in the steps 1) and 2) are respectively 0.01-0.1 MPa, and the drying is carried out for 4-8 h at the temperature of 50-80 ℃;
the centrifugation conditions in the steps 1) and 2) are respectively 4000-10000 rpm for 20-60 min;
the activation in the step 2) is carried out under the condition of stirring, and the stirring speed is 500-1500 rpm;
the reaction is carried out under the condition of stirring, and the stirring speed is 500-2000 rpm.
The near-infrared photosensitizer can emit blue light and red light under near-infrared illumination, can kill tumor cells and tissues, and has photodynamic tumor treatment and optical diagnosis effects.
The near-infrared photosensitizer is applied to the preparation of photodynamic tumor treatment medicines and tumor cell imaging agents.
The principle of the invention is that cinnamaldehyde is made into a carbon point with up-conversion function, under the action of urea, the carbon point is coupled with amino, and then the carbon point and carboxyl of the pheophorbide are subjected to amide reaction to prepare a covalent compound of the up-conversion carbon point and the pheophorbide. The carbon dots convert near infrared light energy and transmit the near infrared light energy to the pheophorbide through the action of fluorescence energy resonance transfer, so that the pheophorbide generates photodynamic action.
Compared with the prior art, the invention has the following advantages and effects:
(1) the near-infrared photosensitizer overcomes the defect that the conventional photosensitizer cannot perform photodynamic therapy on deep tumors because the exciting light is visible light. The near-infrared photosensitizer has a very good inhibition effect on tumor cells.
(2) The preparation process is simple and easy to realize industrialization.
Detailed Description
The present invention is further described in detail with reference to the following examples, but the embodiments of the present invention are not limited thereto.
Example 1
(1) Dissolving 0.1mol of cinnamaldehyde and 0.1mol of urea in 100mL of dimethyl sulfoxide, transferring into a reaction kettle, reacting at 180 ℃ for 12h (solvent thermal reaction), centrifuging at 4000rpm for 60min, dialyzing the supernatant by a dialysis membrane with the molecular weight cutoff of 2000Da for 48h, and drying at 50 ℃ for 4h under 0.01MPa to obtain 14g of carbon dots.
(2) Dissolving 0.1mol of pheophorbide in 300mL of dimethyl sulfoxide, stirring uniformly, then adding 19.2g of EDC and 11.5g of NHS, stirring at room temperature of 500rpm, and reacting for 60min to obtain an activated pheophorbide solution; dispersing 5.97g of carbon dots in 30mL of dimethyl sulfoxide, then dropwise adding the carbon dots into a pheophorbide solution, stirring and reacting for 18h at the room temperature of 500rpm, centrifuging for 60min at 4000rpm, dialyzing the supernatant by a dialysis membrane with the molecular weight cutoff of 2000Da for 48h, and drying at 50 ℃ for 4h to obtain 65g of the near-infrared photosensitizer.
Example 2
(1) Dissolving 0.1mol of cinnamaldehyde and 0.3mol of urea in 620mL of dimethylformamide, transferring into a reaction kettle, reacting at 220 ℃ for 6h, centrifuging at 10000rpm for 20min, dialyzing the supernatant by a dialysis membrane with the molecular weight cutoff of 6000Da for 12h, drying at 0.1MPa at 80 ℃ for 8h to obtain 21g of carbon dots.
(2) Dissolving 0.1mol of pheophorbide in 1190mL of tetrahydrofuran, stirring uniformly, then adding 57.5g of EDC and 34.5g of NHS, stirring at room temperature of 1500rpm, and reacting for 20min to obtain an activated pheophorbide solution; dispersing 11.93g of carbon dots in 230mL of tetrahydrofuran, then dropwise adding the mixture into a pheophorbide solution, stirring and reacting for 12h at the room temperature of 2000rpm, centrifuging for 20min at 10000rpm, dialyzing the supernatant for 12h by a dialysis membrane with the molecular weight cutoff of 6000Da, and drying for 8h at the temperature of 80 ℃ to obtain 71g of the near-infrared photosensitizer.
Example 3
(1) Dissolving 0.1mol of cinnamaldehyde and 0.2mol of urea in 450mL of tetrahydrofuran, transferring into a reaction kettle, reacting at 200 ℃ for 10h, centrifuging at 8000rpm for 30min, dialyzing the supernatant by a dialysis membrane with the molecular weight cutoff of 4000Da for 24h, drying at 0.05MPa at 70 ℃ for 5h to obtain 18g of carbon dots.
(2) Dissolving 0.1mol of pheophorbide in 800mL of dimethylformamide, stirring uniformly, then adding 40g of EDC and 25g of NHS, stirring and reacting for 30min at room temperature and 1000rpm to obtain an activated pheophorbide solution; dispersing 8g of carbon dots in 160mL of dimethylformamide, then dropwise adding the dimethylformamide into a pheophorbide solution, stirring and reacting for 15h at the room temperature of 1000rpm, centrifuging for 30min at 8000rpm, dialyzing the supernatant by a dialysis membrane with the molecular weight cutoff of 4000Da for 24h, and drying at the temperature of 70 ℃ for 6h to obtain 68g of the near-infrared photosensitizer.
Example 4
(1) Dissolving 0.1mol of cinnamaldehyde and 0.15mol of urea in 300mL of dimethyl sulfoxide, transferring into a reaction kettle, reacting at 190 ℃ for 8h, centrifuging at 6000rpm for 40min, dialyzing the supernatant by a dialysis membrane with the molecular weight cutoff of 5000Da for 36h, drying at 0.02MPa at 60 ℃ for 5h to obtain 16g of carbon dots.
(2) Dissolving 0.1mol of pheophorbide (pheophorbide A) in 500mL of dimethylformamide, stirring uniformly, then adding 30g of EDC and 20g of NHS, stirring and reacting at room temperature of 800rpm for 40min to obtain an activated pheophorbide solution; dispersing 6g of carbon dots in 100mL of dimethyl sulfoxide, then dropwise adding the carbon dots into a pheophorbide solution, stirring and reacting for 16h at the room temperature of 800rpm, centrifuging for 40min at 6000rpm, dialyzing the supernatant for 36h by a dialysis membrane with the molecular weight cutoff of 5000Da, and drying for 5h at the temperature of 60 ℃ to obtain 67g of the near-infrared photosensitizer.
Example 5
Upconversion photometry of carbon dots and near infrared photosensitizers prepared in examples 1-4.
The method comprises the following steps: the carbon dots prepared in examples 1 to 4 and the near-infrared photosensitizer were respectively detected in their emission peak positions under 780nm laser excitation on a photometer. And performing hydrothermal reaction on chitosan at 200 ℃ for 10 hours, cooling, centrifuging, filtering and drying to obtain carbon dots, wherein the chitosan carbon dots and the pheophorbide conjugate are prepared as a comparison by the method in the step (2) in the example 1.
As a result: the maximum emission wavelengths of the carbon dots prepared in examples 1 to 4 were 410nm, 413nm, 415nm, and 411nm, respectively, indicating that they can up-convert near infrared light into visible light. The maximum emission wavelengths of the near-infrared photosensitizers prepared in examples 1 to 4 had emission peaks at 667nm, 670nm, 672nm, and 671nm, respectively, in addition to the same emission peaks as those of the corresponding carbon sites, indicating that they activated pheophorbide and produced emission peaks of pheophorbide. This indicates that energy is transferred to pheophorbide by the carbon spot in the covalently linked near infrared photosensitizer through the fluorescence energy resonance transfer process, so that the pheophorbide is excited to generate red light. The chitosan carbon dot and pheophorbide conjugate has no emission peak under 780nm laser irradiation, which indicates that other carbon dots have no light conversion function of the carbon dots.
Example 6
Growth inhibition experiments on tumor cells with the near-infrared photosensitizers prepared in examples 1-4.
The method comprises the following steps: tumor cells (gastric cancer RF cell line and rectal cancer LS174T cell line, concentration 2X 106/mL), placing into a sterile 96-well culture plate, adding 50 μ L of tumor cell suspension into each well, adding 50 μ L of 1640 culture solution containing 15% calf serum, adding 10 μ L of 1mg/mL DMF solution of the near-infrared photosensitizer prepared in example 1-4, adding 3 wells into each well, shaking and mixing with equal amount of normal saline, irradiating with 780nm laser (300mW) for 20min, and adding 5% CO2The culture was carried out in an incubator (37 ℃) for 24 hours, tetrazolium salt (MTT) phosphate buffer was added thereto, 10. mu.L/well (MTT 5 mg/mL) was further incubated for 4 hours, and then 100. mu.L of dimethyl sulfoxide was added thereto to terminate the reaction. The result was calculated by measuring the OD at the wavelength of 570nm and 630nm, respectively, using an ELISA in the wells without light as a control.
Calculating the formula:
as a result: the results are shown in Table 1.
TABLE 1 inhibition test of the near-infrared photosensitizers prepared in examples 1 to 4 for gastric and rectal cancer
Gastric cancer RF cell line and rectal cancer LS174T cell line are common digestive tract tumor cell lines. Experiments show that the near-infrared photosensitizer prepared in examples 1-4 has significantly improved inhibition effects on two tumors compared with the single porphyrin compound drug, and the inhibition rate is increased from 45.9-53.8% to 73.6-88.3%, which indicates that the near-infrared photosensitizer formed by carbon dots and pheophorbide of the invention has stronger photosensitization and tumor cell killing effects under 780nm laser irradiation, and the inhibition effect is significantly improved. The effect of chitosan carbon dot and pheophorbide conjugate on tumor is not improved compared with pheophorbide.
Example 7
Experiment for inhibiting tumor growth in mice with the near-infrared photosensitizers prepared in examples 1 to 4.
The method comprises the following steps: taking S180 tumor mass of mouse, homogenizing, diluting and adjusting cell number to 1 × 1070.2mL of the extract is injected into the right axilla of Kunming mice (male, 18-22 g), the subcutaneous administration is carried out after 24h, the administration is carried out in groups at random, the tail vein injection is carried out, the administration dose is 5mg/kg, 1 time every day, and after 30min, the tumor part is irradiated by 780nm laser (300mW) for 30 min. On the eighth day, the mice are weighed, sacrificed, tumor masses are taken out, the tumor weight and the tumor volume are measured, and the tumor inhibition rate is calculated.
Tumor inhibition rate (weight tumor inhibition rate + volume tumor inhibition rate)/2
Tumor inhibition rate (tumor weight in normal saline administration)/tumor weight in normal saline × 100
The tumor volume inhibition rate is (tumor volume in normal saline group-tumor volume in administration group)/tumor volume in normal saline group x 100
As a result: the results are shown in Table 2.
Table 2 animal experiments on the inhibition of S180 sarcoma by the near-infrared photosensitizers prepared in examples 1-4.
The tumor inhibition rate of the near-infrared photosensitizer prepared in the embodiment 1-4 to S180 is obviously higher than that of a single porphyrin compound administration group, and the tumor inhibition rate is improved from 33.1-43.6% to 65.8-69.2%, which shows that the near-infrared photosensitizer formed by carbon dots and pheophorbide generates a photosensitization inhibition effect on tumors in animals when the near-infrared photosensitizer is irradiated by 780nm laser, and the inhibition effect is obviously improved. The effect of chitosan carbon dot and pheophorbide conjugate on tumor is not improved compared with pheophorbide.
The above examples of the present invention are merely examples for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (9)
1, near-infrared photosensitizers, characterized by the molecular structure:
2. The method for producing the near-infrared photosensitizer according to claim 1, characterized in that: the method specifically comprises the following steps:
1) reacting cinnamaldehyde and urea in an organic solvent at 180-220 ℃ for 6-12 h, centrifuging, dialyzing supernate, and drying to obtain carbon dots;
2) activating the pheophorbide by an activating agent in an organic solvent to obtain activated pheophorbide; dispersing carbon dots in an organic solvent to obtain a carbon dot dispersion liquid; and dripping the carbon dot dispersion liquid into activated pheophorbide, reacting, centrifuging, dialyzing, and drying to obtain the near-infrared photosensitizer.
3. The method for producing the near-infrared photosensitizer according to claim 2, characterized in that: the molar ratio of the cinnamaldehyde to the urea is 1: (1-3); the amount of the carbon dots is 1/5-1/10 of the mass of the pheophorbide.
4. The method for producing the near-infrared photosensitizer according to claim 2, characterized in that: the activators are EDC and NHS.
5. The method for producing the near-infrared photosensitizer according to claim 4, wherein: the dosage of the EDC is 1-3 times of the molar weight of the pheophorbide; the dosage of the NHS is 1-3 times of the molar weight of the pheophorbide.
6. The method for producing the near-infrared photosensitizer according to claim 2, characterized in that: the reaction condition in the step 2) is room temperature reaction for 12-18 h;
the activating condition in the step 2) is room temperature reaction for 20-60 min;
the organic solvent in the step 1) is more than of dimethyl sulfoxide, dimethylformamide or tetrahydrofuran;
in the step 2), the organic solvent in the activated pheophorbide is more than of dimethyl sulfoxide, dimethyl formamide or tetrahydrofuran, and the organic solvent in the carbon point dispersion liquid is more than of dimethyl sulfoxide, dimethyl formamide or tetrahydrofuran.
7. The method for producing the near-infrared photosensitizer according to claim 2, characterized in that: the dialysis in the step 1) refers to dialysis membrane dialysis with the molecular weight cutoff of 2000-6000 Da;
the dialysis in the step 2) refers to dialysis membrane dialysis with the molecular weight cutoff of 2000-6000 Da;
the mass ratio of the volume of the organic solvent to the mass of the cinnamaldehyde and the urea in the step 1) is (1-20) to 1 (mL/g);
the mass ratio of the volume of the organic solvent in the activated pheophorbide to the pheophorbide in the step 2) is (1-20) mL: 1 g; the mass ratio of the volume of the organic solvent to the carbon dots in the carbon dot dispersion liquid is (1-20) mL: 1 g.
8. The method for producing the near-infrared photosensitizer according to claim 2, characterized in that: the dialysis time in the steps 1) and 2) is 12-48 h respectively;
the drying conditions in the steps 1) and 2) are respectively 0.01-0.1 MPa 50-80 ℃ for 4-8 h;
the centrifugation conditions in the steps 1) and 2) are respectively 4000-10000 rpm for 20-60 min;
the activation in the step 2) is carried out under the condition of stirring, and the stirring speed is 500-1500 rpm;
the reaction in the step 2) is carried out under the stirring condition, and the stirring speed is 500-2000 rpm.
9. The use of the near-infrared photosensitizer of claim 1 in the preparation of a medicament for photodynamic therapy of tumors and in a tumor cell imaging agent.
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| CN103223171A (en) * | 2013-04-03 | 2013-07-31 | 华南理工大学 | Porphyrin and uptransition rare earth nanocomposite, preparation method and application thereof |
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| WO2019010329A1 (en) * | 2017-07-06 | 2019-01-10 | The Trustees Of The University Of Pennsylvania | Amphiphilic dye-coated inorganic nanoparticle clusters |
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| CN103223171A (en) * | 2013-04-03 | 2013-07-31 | 华南理工大学 | Porphyrin and uptransition rare earth nanocomposite, preparation method and application thereof |
| WO2019010329A1 (en) * | 2017-07-06 | 2019-01-10 | The Trustees Of The University Of Pennsylvania | Amphiphilic dye-coated inorganic nanoparticle clusters |
| CN107998389A (en) * | 2017-11-20 | 2018-05-08 | 中国人民解放军军事医学科学院卫生装备研究所 | It is a kind of can bioluminescence triggering upper conversion carbon quantum dot-protoporphyrin IX complex photosensitizer and preparation method thereof |
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