CN110698665A - Preparation method of oxazoline-based near-infrared material - Google Patents
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Abstract
The invention relates to the field of pharmacy, and discloses a preparation method of a Lelinyl-based near-infrared material aiming at the problems of weak gene bearing capacity and poor biocompatibility of a tumor targeted therapy drug carrier in the prior art, wherein the preparation method comprises the following steps of (1) synthesizing a Lelinyl monochloro substituted perylene dianhydride compound: a. dissolving perylene dianhydride in concentrated sulfuric acid, wherein the mass ratio is 0.7-1.2: 2.2-2.4; b. slowly dripping TBCA solution of concentrated sulfuric acid into the mixed solution; c. when an alcohol phase appears, dialyzing and purifying with deionized water, keeping out of the sun during the period, and freeze-drying to obtain PDI; (2) and preparing the oxazoline-based near-infrared material nano-drug: the PDI and the polyethylene glycol are dissolved in deionized water according to the mass ratio of 0.8-1:1.4-1.8 and are subjected to ultrasonic stirring treatment. The invention has larger topological branched chain structure, stronger drug bearing capacity and certain sterilization capacity, and the obtained product has better thermal stability and simple preparation process.
Description
Technical Field
The invention relates to the field of pharmacy, in particular to a preparation method of a Leolin-based near-infrared material.
Background
Near-infrared light-excited photothermal therapy can effectively make up for the defects of the traditional cancer treatment means, but the currently commonly used near-infrared organic photothermal molecules (such as cyanine and the like) have poor light stability, and the light degradation of the near-infrared organic photothermal molecules can influence the stability of the nano structure and the photothermal conversion efficiency. Therefore, a novel near-infrared organic photothermal reagent with high stable nanostructure and high photothermal conversion efficiency is developed, so that the treatment efficiency and the medical safety of tumors are effectively improved. In addition, the infrared material is used as a carrier for in vivo tumor targeted therapy, so the antibacterial performance of the material is also essential.
The patent number CN201810246008.4 is named as 'a photo-thermal tumor drug and synthesis and application thereof in tumor treatment', and provides the photo-thermal tumor drug, which takes a phase-change material as a shell and is internally packaged with a target drug, a near-infrared probe and CuS nano particles. The experiment of the primary laser irradiation temperature rise curve of the photothermal tumor medicament proves that the photothermal material has higher photothermal conversion efficiency, and electron microscope and particle size analysis show that the photothermal material has the characteristic of passively targeting tumors by nano materials, and can be used for combined treatment of chemotherapy and thermotherapy of tumor parts.
The disadvantages are that the hydrophilicity, the biocompatibility and the gene bearing capacity are weak, and the antibacterial performance is poor.
Disclosure of Invention
The invention aims to overcome the problems of weak gene bearing capacity and poor biocompatibility of tumor targeted therapy drug carriers in the prior art, and provides a preparation method of a Leolin-based near-infrared material.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of a Leolin-based near-infrared material comprises the following steps:
(1) synthesizing a Lelinyl monochloro substituted perylene dianhydride compound:
a. dissolving perylene dianhydride in concentrated sulfuric acid, wherein the mass ratio is 0.7-1.2: 2.2-2.4 until all the components are dissolved, and mixing uniformly;
b. slowly dripping TBCA solution of concentrated sulfuric acid into the mixed solution obtained in the step a, keeping reaction, and then detecting the reaction degree;
c. when an alcohol phase appears, separating a high molecular weight product by a chromatographic column, dialyzing and purifying by deionized water, keeping out of the sun during the dialysis and purification, and freeze-drying to obtain green powder, namely the Lelinyl monochloro substituted perylene dianhydride compound;
(2) and preparing the oxazoline-based near-infrared material nano-drug: dissolving the quantitative green powder PDI and polyethylene glycol in deionized water in a mass ratio of 0.8-1:1.4-1.8, and performing ultrasonic stirring treatment to obtain a finished product, and storing the finished product.
The perylene dianhydride is a carrier without biological toxicity, has higher dendritic molecular algebra, has a larger dendritic structure and more positive charges ionized by the tail end amino group, and has stronger gene loading capacity.
PDI (Lelinyl monochloro substituted perylene dianhydride compound) is an organic molecule with strong near-infrared energy absorption, can keep chemical structure stability in acid-base, strong light, high heat and other environments, and has the characteristics of high extinction coefficient and easiness in chemical modification. Therefore, a shell-core topological molecular structure with PDI as a molecular core is introduced to realize the multifunctional biological application of the perylene imide macromolecule, the shell structure is polyethylene glycol (PEG), and the PDI and the polyethylene glycol are subjected to esterification reaction to obtain the polyimide modified perylene imide macromolecule.
The polyethylene glycol has good water solubility, good intermiscibility with a plurality of organic matter components, good hygroscopicity, lubricity, cohesiveness and chemical stability.
Due to the hydrophobicity of polyimide and the hydrogen bond driving force of polyethylene glycol, the photo-thermal nano-drug with good biocompatibility is prepared by self-assembly of macromolecules in aqueous solution, and has stable photo-thermal performance and higher photo-thermal conversion efficiency.
Preferably, step a is carried out under magnetic stirring in a nitrogen atmosphere.
The nitrogen atmosphere can prevent the reactants from being oxidized, and the magnetic stirring is used for fully dissolving the perylene dianhydride and the concentrated sulfuric acid to better form a uniform mixed solution.
Preferably, the volume concentration of the concentrated sulfuric acid in the step a is 65-70%.
The perylene dianhydride cannot be well dispersed when the concentration of the concentrated sulfuric acid is too low, and the perylene dianhydride is easily oxidized when the concentration of the concentrated sulfuric acid is too high, so that a solution with the concentration required by the reaction cannot be obtained.
Preferably, the reaction time in step b is kept at 2.5 ~ 3 h.
Preferably, step b is carried out dropwise at-1 ~ 0 ℃.
Preferably, the dialysis membrane cut-off at said dialysis purification in step c is Mw =2000-2500 Da.
Preferably, the dialysis purification time in step c is 24-30 h.
Preferably, the storage temperature in step (2) is 2 to 8 ℃.
Preferably, the polyethylene glycol in the step (2) is modified polyethylene glycol, the modified polyethylene glycol is prepared by mixing the polyethylene glycol and the flavanone compound according to the mass ratio of 4.8-5.0:1.3-1.6, heating and stirring, wherein the heating temperature is 90 ~ 110 ℃, the heating time is 2.5-3.5h, the stirring speed is 1000-.
The modified polyethylene glycol has antibacterial property while ensuring the hydrophilic property, dispersibility and photo-thermal stability, and can prevent the surrounding part from being infected when the drug carrier is injected into the body, in the process of killing tumor cells or reaches the inflamed part.
The polyethylene glycol and the flavanone compound must have a proper mass ratio, excessive flavanone compound components can excessively consume hydrogen on a polyethylene glycol molecular chain, and if the proportion of the flavanone compound is too low, the antibacterial capability of the obtained modified polyethylene glycol is insufficient, so that an ideal antibacterial effect cannot be achieved.
Introducing the flavanone compound to carry out copolymerization reaction with polyethylene glycol, and carrying out reaction between 4-position hydroxyl on a molecular chain of the flavanone compound and hydrogen on a molecular chain of the polyethylene glycol to obtain modified polyethylene glycol with antibacterial property, wherein pentenyl substitutes on the molecular chain of the flavanone compound have stronger antibacterial and bactericidal capabilities.
The heating energy provides power for the copolymerization reaction to promote the reaction to occur, and the heating, the heat preservation for a period of time and the stirring at a certain stirring speed are carried out to ensure that the reaction is fully carried out, so as to obtain the polyethylene glycol with better antibacterial property.
Preferably, the concentration of diethyl ether is 95 ~ 98% by volume.
In order to ensure that the modified polyethylene glycol in the mixed solution can be fully precipitated and separated out, the component purity of the modified polyethylene glycol is ensured.
Therefore, the invention has the following beneficial effects:
(1) the nano-composite material has a larger topological branched chain structure, stronger drug carrying capacity, stronger photo-thermal performance and photo-thermal conversion rate;
(2) the antibacterial agent has stronger antibacterial capacity, and the obtained product has better thermal stability and stronger biocompatibility;
(3) the ultra-small, controllable and stable nanostructure is beneficial to deep penetration of tumor tissues and effective metabolism from the body, can penetrate deeper tissues and reduce the secondary damage to organisms caused by drug dosage and laser radiation.
Drawings
FIG. 1 is a graph showing cytotoxicity data of PDI-NPs of various concentrations according to the present invention (the left side of the graph represents 10% PDI-NP, the middle represents 5% PDI-NP, and the right side represents Control).
FIG. 2 is a graph showing the effect of photothermal therapy at the cellular level of PDI-NP at various concentrations according to the present invention.
Detailed Description
The invention is further described with reference to specific embodiments.
Example 1
A preparation method of a Leolin-based near-infrared material comprises the following steps: (1) synthesizing a Lelinyl monochloro substituted perylene dianhydride compound: a. dissolving perylene dianhydride in concentrated sulfuric acid, wherein the mass ratio is 1: 2.3 until all the components are dissolved, uniformly mixing, and completing the reaction under the condition of magnetic stirring in a nitrogen atmosphere, wherein the volume concentration of concentrated sulfuric acid is 67 percent, b, slowly dripping TBCA solution of the concentrated sulfuric acid into the mixed solution obtained in the step a at the temperature of-0.5 ℃, keeping the reaction for 2.7h, and then detecting the reaction degree; c. when an alcohol phase appears, separating a high molecular weight product by using a chromatographic column, dialyzing and purifying by using deionized water for 28h, wherein the molecular weight cut-off Mw of a dialysis membrane at the dialysis and purification position is =2300Da, and keeping out of the sun during the dialysis and purification period, and freeze-drying to obtain green powder, namely the Lelinyl monochloro substituted perylene dianhydride compound; (2) and preparing the oxazoline-based near-infrared material nano-drug: dissolving the quantitative green powder PDI and polyethylene glycol in deionized water in a mass ratio of 0.9:1.6, performing ultrasonic stirring treatment to obtain a finished product, and storing at 5 ℃.
Example 2
The difference from the embodiment 1 is that the preparation method of the oxazoline-based near-infrared material comprises the following steps: (1) synthesizing a Lelinyl monochloro substituted perylene dianhydride compound: a. dissolving perylene dianhydride in concentrated sulfuric acid, wherein the mass ratio is 0.7: 2.2 until all the components are dissolved, uniformly mixing, and completing the reaction under the condition of magnetic stirring in a nitrogen atmosphere, wherein the volume concentration of concentrated sulfuric acid is 65 percent, b, slowly dropwise adding the TBCA solution of the concentrated sulfuric acid into the mixed solution obtained in the step a at the temperature of-1 ℃, keeping the reaction for 2.5 hours, and then detecting the reaction degree; c. when an alcohol phase appears, separating a high molecular weight product by using a chromatographic column, dialyzing and purifying by using deionized water for 24h, wherein the molecular weight cut-off of a dialysis membrane at the dialysis and purification position is Mw =2000Da, and keeping out of the sun during the dialysis and purification period, and freeze-drying to obtain green powder, namely the Lelinyl monochloro substituted perylene dianhydride compound;
(2) and preparing the oxazoline-based near-infrared material nano-drug: dissolving the quantitative green powder PDI and polyethylene glycol in deionized water in a mass ratio of 0.8:1.4, performing ultrasonic stirring treatment to obtain a finished product, and storing at 2 ℃.
Example 3
The difference from the embodiment 1 is that the preparation method of the oxazoline-based near-infrared material comprises the following steps: (1) synthesizing a Lelinyl monochloro substituted perylene dianhydride compound: a. dissolving perylene dianhydride in concentrated sulfuric acid, wherein the mass ratio is 1.2: 2.4 until all the components are dissolved, uniformly mixing, and completing the reaction under the condition of magnetic stirring in a nitrogen atmosphere, wherein the volume concentration of concentrated sulfuric acid is 70 percent, b, slowly dropwise adding the TBCA solution of the concentrated sulfuric acid into the mixed solution obtained in the step a at the temperature of 0 ℃, keeping the reaction for 3 hours, and then detecting the reaction degree; c. when an alcohol phase appears, separating a high molecular weight product by using a chromatographic column, dialyzing and purifying by using deionized water for 30h, wherein the molecular weight cut-off of a dialysis membrane at the dialysis and purification position is Mw =2500 Da, and keeping out of the sun during the dialysis and purification period, and freeze-drying to obtain green powder, namely the Lelinyl monochloro substituted perylene dianhydride compound;
(2) and preparing the oxazoline-based near-infrared material nano-drug: dissolving the quantitative green powder PDI and polyethylene glycol in deionized water in a mass ratio of 1: 1.8, performing ultrasonic stirring treatment to obtain a finished product, and storing at 8 ℃.
Example 4
A preparation method of a Leolin-based near-infrared material comprises the following steps: (1) synthesizing a Lelinyl monochloro substituted perylene dianhydride compound: a. dissolving perylene dianhydride in concentrated sulfuric acid, wherein the mass ratio is 1: 2.3 until all the components are dissolved, uniformly mixing, and completing the reaction under the condition of magnetic stirring in a nitrogen atmosphere, wherein the volume concentration of concentrated sulfuric acid is 67 percent, b, slowly dripping TBCA solution of the concentrated sulfuric acid into the mixed solution obtained in the step a at the temperature of-0.5 ℃, keeping the reaction for 2.7h, and then detecting the reaction degree; c. when an alcohol phase appears, separating a high molecular weight product by using a chromatographic column, dialyzing and purifying by using deionized water for 28h, wherein the molecular weight cut-off Mw of a dialysis membrane at the dialysis and purification position is =2300Da, and keeping out of the sun during the dialysis and purification period, and freeze-drying to obtain green powder, namely the Lelinyl monochloro substituted perylene dianhydride compound;
(2) and preparing the oxazoline-based near-infrared material nano-drug: dissolving the quantitative green powder PDI and polyethylene glycol in deionized water in a mass ratio of 0.9:1.6, performing ultrasonic stirring treatment to obtain a finished product, and storing at 5 ℃; the polyethylene glycol is modified polyethylene glycol, and the average molecular weight of the modified polyethylene glycol is 3300.
Preparation of the modified polyethylene glycol: mixing polyethylene glycol and flavanone compound according to the mass ratio of 1.9:1.5, wherein the flavanone compound is 3 ', 5' -diisopentenyl-47-hydroxy-2-aryl-chroman-4-one, the concentration is 0.03mol/L, heating and stirring, the heating temperature is 100 ℃, the heating time is 3 hours, the stirring speed is 1100 r/min, cooling to room temperature, filtering, adding ether to precipitate filtrate, the volume concentration of the ether is 96%, and drying to obtain the modified polyethylene glycol.
Example 5
The difference from the embodiment 4 is that the preparation method of the oxazoline-based near-infrared material comprises the following steps: (1) synthesizing a Lelinyl monochloro substituted perylene dianhydride compound: a. dissolving perylene dianhydride in concentrated sulfuric acid, wherein the mass ratio is 0.7: 2.2 until all the components are dissolved, uniformly mixing, and completing the reaction under the condition of magnetic stirring in a nitrogen atmosphere, wherein the volume concentration of concentrated sulfuric acid is 65 percent, b, slowly dropwise adding the TBCA solution of the concentrated sulfuric acid into the mixed solution obtained in the step a at the temperature of-1 ℃, keeping the reaction for 2.5 hours, and then detecting the reaction degree; c. when an alcohol phase appears, separating a high molecular weight product by using a chromatographic column, dialyzing and purifying by using deionized water for 24h, wherein the molecular weight cut-off of a dialysis membrane at the dialysis and purification position is Mw =2000Da, and keeping out of the sun during the dialysis and purification period, and freeze-drying to obtain green powder, namely the Lelinyl monochloro substituted perylene dianhydride compound;
(2) and preparing the oxazoline-based near-infrared material nano-drug: dissolving the quantitative green powder PDI and polyethylene glycol in deionized water in a mass ratio of 0.8:1.4, performing ultrasonic stirring treatment to obtain a finished product, and storing at 2 ℃; the polyethylene glycol is modified polyethylene glycol, and the average molecular weight of the modified polyethylene glycol is 3500.
Preparation of the modified polyethylene glycol: mixing polyethylene glycol and flavanone compound according to the mass ratio of 1.8:1.3, wherein the flavanone compound is 3 ', 5' -diisopentenyl-47-hydroxy-2-aryl-chroman-4-one, the concentration is 0.02mol/L, heating and stirring, the heating temperature is 90 ℃, the heating time is 2.5 hours, the stirring speed is 1000 r/min, cooling to room temperature, filtering, adding ether to precipitate filtrate, the volume concentration of the ether is 95%, and drying to obtain the modified polyethylene glycol.
Example 6
The difference from the embodiment 4 is that the preparation method of the oxazoline-based near-infrared material comprises the following steps: (1) synthesizing a Lelinyl monochloro substituted perylene dianhydride compound: a. dissolving perylene dianhydride in concentrated sulfuric acid, wherein the mass ratio is 1.2: 2.4 until all the components are dissolved, uniformly mixing, and completing the reaction under the condition of magnetic stirring in a nitrogen atmosphere, wherein the volume concentration of concentrated sulfuric acid is 70 percent, b, slowly dropwise adding the TBCA solution of the concentrated sulfuric acid into the mixed solution obtained in the step a at the temperature of 0 ℃, keeping the reaction for 3 hours, and then detecting the reaction degree; c. when an alcohol phase appears, separating a high molecular weight product by using a chromatographic column, dialyzing and purifying by using deionized water for 30h, wherein the molecular weight cut-off of a dialysis membrane at the dialysis and purification position is Mw =2500 Da, and keeping out of the sun during the dialysis and purification period, and freeze-drying to obtain green powder, namely the Lelinyl monochloro substituted perylene dianhydride compound;
(2) and preparing the oxazoline-based near-infrared material nano-drug: dissolving the quantitative green powder PDI and polyethylene glycol in deionized water in a mass ratio of 1: 1.8, performing ultrasonic stirring treatment to obtain a finished product, and storing at 8 ℃; the polyethylene glycol is modified polyethylene glycol, and the average molecular weight of the modified polyethylene glycol is 4000.
Preparation of the modified polyethylene glycol: mixing polyethylene glycol and flavanone compound according to the mass ratio of 2.0: 1.6, wherein the flavanone compound is 3 ', 5' -diisopentenyl-47-hydroxy-2-aryl-chroman-4-one, the concentration is 0.04mol/L, heating and stirring, the heating temperature is 110 ℃, the heating time is 3.5 hours, the stirring speed is 1200 r/min, cooling to room temperature, filtering, adding ether to precipitate filtrate, the volume concentration of the ether is 98%, and drying to obtain the modified polyethylene glycol.
The finished products obtained in the embodiments 1-3 have good biocompatibility and high permeability, and are beneficial to deep penetration of tumor tissues and effective metabolism from the body; near infrared absorption and high photothermal conversion efficiency, can penetrate deeper tissues and reduce the secondary damage to organisms caused by drug dosage and laser radiation; excellent light stability and strong photoacoustic signal.
The finished products obtained in examples 4-6 have additional antibacterial property, can prevent infection and treat inflammation, and achieve better treatment effect on tumors.
From examples 1 to 6, it is clear that only solutions within the scope of the claims of the present invention are able to satisfy the above requirements in all respects, resulting in an optimized solution and in a battery material with optimal performance. The change of the mixture ratio, the replacement/addition/subtraction of raw materials or the change of the feeding sequence can bring corresponding negative effects.
The raw materials and equipment used in the invention are common raw materials and equipment in the field if not specified; the methods used in the present invention are conventional in the art unless otherwise specified.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and all simple modifications, alterations and equivalents of the above embodiments according to the technical spirit of the present invention are still within the protection scope of the technical solution of the present invention.
Claims (10)
1. A preparation method of a Leolin-based near-infrared material is characterized by comprising the following steps:
(1) synthesizing a Lelinyl monochloro substituted perylene dianhydride compound:
a. dissolving perylene dianhydride in concentrated sulfuric acid, wherein the mass ratio is 0.7-1.2: 2.2-2.4 until all the components are dissolved, and mixing uniformly;
b. slowly dripping TBCA solution of concentrated sulfuric acid into the mixed solution obtained in the step a, keeping reaction, and then detecting the reaction degree;
c. when an alcohol phase appears, separating a high molecular weight product by a chromatographic column, dialyzing and purifying by deionized water, keeping out of the sun during the dialysis and purification, and freeze-drying to obtain green powder, namely the Lelinyl monochloro substituted perylene dianhydride compound;
(2) and preparing the oxazoline-based near-infrared material nano-drug: dissolving the quantitative green powder PDI and polyethylene glycol in deionized water in a mass ratio of 0.8-1:1.4-1.8, and performing ultrasonic stirring treatment to obtain a finished product, and storing the finished product.
2. The method according to claim 1, wherein the step a is performed under magnetic stirring in a nitrogen atmosphere.
3. The method according to claim 1, wherein the concentrated sulfuric acid in step a has a volume concentration of 65-70%.
4. The method of claim 1, wherein the maintaining time in step b is 2.5 ~ 3 hours.
5. The method according to claim 1, wherein the step b is carried out at-1 ~ 0 ℃.
6. The method as claimed in claim 1, wherein the dialysis membrane cut-off molecular weight of the dialysis purification site in step c is Mw =2000-2500 Da.
7. The method according to claim 1, wherein the dialysis purification time in step c is 24-30 h.
8. The method for preparing a lyoline-based near-infrared material according to claim 1, wherein the storage temperature in the step (2) is 2 to 8 ℃.
9. The method according to claim 1, wherein the polyethylene glycol is modified polyethylene glycol, the modified polyethylene glycol is prepared by mixing polyethylene glycol and flavanone compound at a mass ratio of 4.8-5.0:1.3-1.6, heating and stirring at 90 ~ 110 ℃ for 2.5-3.5h at a stirring speed of 1000-.
10. The method of claim 9, wherein the concentration of diethyl ether is 95 ~ 98% by volume.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6166210A (en) * | 1997-12-15 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Perylene imide monocarboxylic acids |
| CN107033267A (en) * | 2017-03-15 | 2017-08-11 | 北京化工大学 | A series of preparation of water-soluble polymers based on Lay quinoline based compound and its as photothermal reagent in biomedical application |
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- 2019-08-07 CN CN201910725560.6A patent/CN110698665A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6166210A (en) * | 1997-12-15 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Perylene imide monocarboxylic acids |
| CN107033267A (en) * | 2017-03-15 | 2017-08-11 | 北京化工大学 | A series of preparation of water-soluble polymers based on Lay quinoline based compound and its as photothermal reagent in biomedical application |
Non-Patent Citations (1)
| Title |
|---|
| 张少博: ""新型莱啉系列近红外光热纳米药物的制备与肿瘤诊疗研究"", 《中国优秀博硕士学位论文全文数据库（博士） 工程科技I辑》 * |
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