CN115282298B - Preparation method and application of monodisperse yttrium-90 polymer microspheres - Google Patents
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Abstract
The invention discloses a preparation method and application of monodisperse yttrium-90 polymer microspheres, wherein the preparation method of the monodisperse yttrium-90 polymer microspheres comprises the following steps: s1) preparing microspheres with surface chelated carboxyl functional groups by using polymer microspheres; s2) mixing yttrium chloride [90Y ] solution with the microsphere with the surface chelated carboxyl functional group, uniformly stirring, reacting for 0.5-2h at 40-50 ℃, and cleaning with normal saline after the reaction is finished to obtain the monodisperse yttrium-90 polymer microsphere. The high molecular polymer microsphere has high-capacity surface functional groups, and can fully react with more yttrium chloride (90Y), so that the chelating efficiency of the monodisperse yttrium-90 high molecular microsphere is improved.
Description
Technical Field
The invention relates to the field of tumor radiotherapy drug microspheres, in particular to a preparation method and application of monodisperse yttrium-90 polymer microspheres.
Background
Interventional radiotherapy technology is a method for effectively treating tumors, and radioactive microspheres have been widely used due to dual interventional therapy of tumors such as internal radiation and vascular embolism.
Yttrium [90Y ] has the following advantages as a selective internal radiation therapy: the pure beta rays are emitted, the energy is high, the half-life period is short, the in-vivo penetration distance is short, and the protection is easy; the stability is good, decay products are harmless, and 95% of energy is released within two weeks. At present, the microspheres for radioactive tumor treatment mainly comprise yttrium [90Y ] glass microspheres and yttrium [90Y ] resin microspheres, but the glass microspheres have the risk of being deposited on the wall of a blood vessel and not being capable of more accurately selecting tumor parts because of the too heavy specific gravity; the resin microsphere has lighter specific gravity, easy dispersion and better operability, can reach each corner of the tumor along with arterial capillaries of liver cancer, has good application, but the resin microsphere usually adsorbs yttrium (90Y) through sulfonic groups, has low adsorption efficiency, and is unstable in adsorption and drops off the solution.
Disclosure of Invention
The invention aims to provide a preparation method and application of monodisperse yttrium-90 polymer microspheres, so as to solve the technical problems.
In order to achieve the above purpose, the invention adopts the following technical scheme: a method for preparing monodisperse yttrium-90 polymer microspheres, which comprises the following steps,
s1) preparing microspheres with surface chelated carboxyl functional groups by using polymer microspheres;
s2) mixing yttrium chloride [90Y ] solution with the microsphere with the surface chelated carboxyl functional group, uniformly stirring, reacting for 0.5-2h at 40-50 ℃, and cleaning with normal saline after the reaction is finished to obtain the monodisperse yttrium-90 polymer microsphere.
As further optimization, S1 comprises the following steps of S11) preparing polymer microspheres with chloroacetyl chloride functional groups on the surfaces by using high molecular microspheres; s12) preparing hydroxyl polymer microspheres by using chloracetyl chloride functional group polymer microspheres; s13) preparing surface grafting GMA polymer microspheres by using hydroxyl polymer microspheres; s14) preparing surface-grafted GMA polymer microspheres by using hydroxyl polymer microspheres to prepare surface-chelated carboxyl functional group microspheres.
As further optimization, adding chloroacetyl chloride and anhydrous aluminum trichloride into the polymer microspheres in the step S11, and washing and drying after the reaction to obtain polymer microspheres with the surface containing chloroacetyl chloride functional groups; wherein the reaction temperature is 30-40 ℃, the reaction time is 12-24h, and the drying temperature is 80-100 ℃.
As further optimization, S12 is to add the chloracetyl chloride functional group polymer microsphere into sodium hydroxide solution, reflux, cleaning and drying to obtain the hydroxyl polymer microsphere.
As further optimization, in S13, adding the hydroxyl polymer microsphere into ceric ammonium nitrate solution, then adding glycidyl methacrylate for reaction for 5-10h, and cleaning after the reaction to obtain the surface grafting GMA polymer microsphere.
As further optimization, preparing sodium iminodiacetate in S14, then adding surface grafting GMA polymer microspheres, and cleaning after reaction to obtain the surface chelating carboxyl functional group microspheres, wherein the reaction temperature is 50-60 ℃ and the reaction time is 12-24h.
As a further optimization, the polymer microsphere in S1 is one or more of polystyrene/divinylbenzene copolymer microsphere, polystyrene/triallyl isocyanurate microsphere, polymethyl methacrylate/divinylbenzene copolymer microsphere or polymethyl methacrylate/triallyl isocyanurate microsphere.
As a further optimization, the particle size of the polymer microsphere in S1 is 100nm-100 μm, and the pore size is 50-2000 angstroms.
The application of monodisperse yttrium-90 polymer microsphere is that the monodisperse yttrium-90 polymer microsphere is used in tumor radiotherapy.
As a further optimization, the chelating efficiency of the monodisperse yttrium-90 polymer microsphere is more than 99.5%, and the release rate of the monodisperse yttrium-90 polymer microsphere to yttrium-90 is less than 0.001%.
Compared with the prior art, the invention has the beneficial effects that:
1. the high molecular polymer microsphere prepared by the invention has higher-capacity surface functional groups, can improve the adsorption capacity of yttrium-90, can fully react with more yttrium chloride [90Y ] to prepare the monodisperse yttrium-90 high molecular microsphere, and improves the chelating efficiency of the monodisperse yttrium-90 high molecular microsphere.
2. The preparation process is simple and easy to industrialize.
Drawings
FIG. 1 is an SEM image of monodisperse yttrium-90 polymer microspheres prepared in example 1 of the invention.
Detailed Description
The following are specific examples of the present invention, and the technical solutions of the present invention are further described, but the present invention is not limited to these examples.
Example 1
A monodisperse yttrium-90 polymer microsphere and a preparation method thereof comprise the following steps:
s1) weighing 10g of polystyrene/divinylbenzene microspheres (30 mu m) and 120g of dichloroethane, adding 4.4g of chloroacetyl chloride and 2g of anhydrous aluminum trichloride, reacting for 24 hours at 30 ℃, sequentially cleaning with ethanol and deionized water, and drying at 90 ℃ to obtain polymer microspheres with chloroacetyl chloride functional groups on the surfaces;
s2) weighing 5g of the chloracetyl chloride functional group microsphere in the S1, adding 10% sodium hydroxide solution, refluxing for 12h, washing with water for 3 times, and drying at 90 ℃ for later use;
s3) weighing 5g of the microspheres in S2, adding 100ml of deionized water, and heating at 60 DEG CMixing and stirring, introducing nitrogen to remove oxygen for 1h, adding 10ml of 0.1M ammonium cerium nitrate solution (dissolved in 1M HNO) 3 After 30min, 10ml of Glycidyl Methacrylate (GMA) was added, the reaction was carried out for 6h, and after the completion of the reaction, the product was repeatedly washed with deionized water to obtain polymer microspheres with surface grafted with GMA, which was expressed as Poly-g-GMA.
S4) 1.6g iminodiacetic acid (IDA) and 1g NaOH were added to 50ml water to form the sodium salt of IDA, and then Poly-g-GMA microspheres 1g and 2M Na were added thereto 2 CO 3 The pH of the solution is regulated to 10-11, the mixed solution is stirred at 60 ℃ for reaction for 12 hours, after the reaction is finished, the particles are repeatedly washed by deionized water, and the product is expressed by Poly-g-GMA-IDA.
S5) weighing 20g of 1M yttrium chloride [90Y ] solution, fully mixing with Poly-g-GMA-IDA microspheres, uniformly stirring and mixing for 40-80 minutes at 40-50 ℃, and repeatedly cleaning with normal saline water for 5 times after the reaction is finished, thus preparing the monodisperse yttrium-90 polymer microspheres.
By detection, the particle size of the microspheres prepared in this example was 30 μm, cv=3%; the maximum radioactivity of the single yttrium-90 polymer microsphere is 2000Bq.
Example 2
A preparation method and application of monodisperse yttrium-90 polymer microspheres comprise the following steps:
s1) weighing 10g of polystyrene/triallyl isocyanurate microspheres (25 mu m) and 120g of dichloroethane, adding 4.4g of chloroacetyl chloride and 2g of anhydrous aluminum trichloride, reacting for 24 hours at 30 ℃, sequentially cleaning with ethanol and deionized water, and drying at 90 ℃ to obtain polymer microspheres with chloroacetyl chloride functional groups on the surfaces;
s2) weighing 5g of the chloracetyl chloride functional group microsphere in the S1, adding 10% sodium hydroxide solution, refluxing for 12h, washing with water for 3 times, and drying at 90 ℃ for later use;
s3) weighing 5g of microspheres in S2, adding 100ml of deionized water, mixing and stirring at 60 ℃, introducing nitrogen to remove oxygen for 1h, and adding 10ml of 0.1M ammonium cerium nitrate solution (dissolved in 1M HNO) 3 After 30min, 10ml of Glycidyl Methacrylate (GMA) is added for reaction for 6h, and after the reaction is finished, the product is repeatedly washed by deionized water to obtain the surfaceThe polymer microsphere grafted with GMA is expressed by Poly-g-GMA;
s4) first 1.6g iminodiacetic acid (IDA) and 1g NaOH were added to 50ml water to form the sodium salt of IDA, then Poly-g-GMA microspheres 1g and 2M Na were added thereto 2 CO 3 The pH value of the solution is regulated to 10-11, the mixed solution is stirred and reacts for 12 hours at 60 ℃, after the reaction is finished, the particles are repeatedly washed by deionized water, and the product is expressed by Poly-g-GMA-IDA;
s5) weighing 20g of 1M yttrium chloride [90Y ] solution, fully mixing with Poly-g-GMA-IDA microspheres, uniformly stirring and mixing for 40-80 minutes at 40-50 ℃, and repeatedly cleaning with normal saline water for 5 times after the reaction is finished, thus preparing the monodisperse yttrium-90 polymer microspheres.
By detection, the particle size of the microspheres prepared in this example was 25 μm, cv=2.9%; the maximum radioactivity of the single yttrium-90 polymer microsphere is 2100Bq.
Example 3
A preparation method and application of monodisperse yttrium-90 polymer microspheres comprise the following steps:
s1) weighing 10g of polystyrene/divinylbenzene microspheres (50 mu m) and 120g of dichloroethane, adding 4.4g of chloroacetyl chloride and 2g of anhydrous aluminum trichloride, reacting for 24 hours at 30 ℃, sequentially cleaning with ethanol and deionized water, and drying at 90 ℃ to obtain polymer microspheres with chloroacetyl chloride functional groups on the surfaces;
s2) weighing 5g of the chloracetyl chloride functional group microsphere in the S1, adding 10% sodium hydroxide solution, refluxing for 12h, washing with water for 3 times, and drying at 90 ℃ for later use;
s3) weighing 5g of microspheres in S2, adding 100ml of deionized water, mixing and stirring at 60 ℃, introducing nitrogen to remove oxygen for 1h, and adding 10ml of 0.1M ammonium cerium nitrate solution (dissolved in 1M HNO) 3 After 30min, 10ml of Glycidyl Methacrylate (GMA) is added for reaction for 6h, and after the reaction is finished, the product is repeatedly washed by deionized water, and the obtained polymer microsphere with the surface grafted with the GMA is expressed as Poly-g-GMA;
s4) first 1.6g iminodiacetic acid (IDA) and 1g NaOH were added to 50ml water to form the sodium salt of IDA, then Poly-g-GMA microspheres 1g and 2M Na were added thereto 2 CO 3 The pH value of the solution is regulated to 10-11, the mixed solution is stirred and reacts for 12 hours at 60 ℃, after the reaction is finished, the particles are repeatedly washed by deionized water, and the product is expressed by Poly-g-GMA-IDA;
s5) weighing 20g of 1M yttrium chloride [90Y ] solution, fully mixing with Poly-g-GMA-IDA microspheres, uniformly stirring and mixing for 40-80 minutes at 40-50 ℃, and repeatedly cleaning with normal saline water for 5 times after the reaction is finished, thus preparing the monodisperse yttrium-90 polymer microspheres.
By detection, the particle size of the microspheres prepared in this example was 50 μm, cv=2.8%; the maximum radioactivity of the single yttrium-90 polymer microsphere is 2000Bq.
Comparative example 1
Resin microspheres and glass microspheres of yttrium [90Y ] on the market were compared with the polymer microspheres of example 2 of the present invention, and the comparison data are shown in the following table.
From the data, the monodisperse yttrium-90 polymer microspheres prepared by the invention have more excellent comprehensive performance, and have smaller microsphere amount per GBq and higher single microsphere radioactivity ratio on the premise of smaller density.
The specific embodiments described herein are offered by way of example only to illustrate the spirit of the invention. Those skilled in the art may make various modifications or additions to the described embodiments or substitutions thereof without departing from the spirit of the invention or exceeding the scope of the invention as defined in the accompanying claims.
Claims (6)
1. A preparation method of monodisperse yttrium-90 polymer microspheres is characterized by comprising the following steps,
s1) preparing a microsphere with a surface chelated carboxyl functional group by using a polymer microsphere, wherein the microsphere comprises the following components:
s11) preparing polymer microspheres with the surface containing chloroacetyl chloride functional groups by using polymer microspheres;
s12) preparing hydroxyl polymer microspheres by using chloracetyl chloride functional group polymer microspheres;
s13) preparing surface grafting GMA polymer microspheres by using hydroxyl polymer microspheres;
s14) preparing surface-grafted GMA polymer microspheres by using hydroxyl polymer microspheres to prepare surface-chelated carboxyl functional group microspheres;
s2) mixing yttrium chloride [90Y ] solution with microspheres with surface chelated carboxyl functional groups, uniformly stirring, reacting at 40-50 ℃ for 0.5-2h, and cleaning with normal saline after the reaction is finished to prepare monodisperse yttrium-90 polymer microspheres;
wherein the polymer microsphere is one or more of polystyrene/divinylbenzene copolymer microsphere, polystyrene/triallyl isocyanurate microsphere, polymethyl methacrylate/divinylbenzene copolymer microsphere or polymethyl methacrylate/triallyl isocyanurate microsphere; the chelating efficiency of the monodisperse yttrium-90 polymer microsphere is more than 99.5%, and the release rate of the monodisperse yttrium-90 polymer microsphere to yttrium-90 is less than 0.001%.
2. The method for preparing monodisperse yttrium-90 polymer microspheres according to claim 1, wherein the polymer microspheres in S11 are added with chloroacetyl chloride and anhydrous aluminum trichloride, and the polymer microspheres with chloroacetyl chloride functional groups on the surfaces are prepared by washing and drying after the reaction; wherein the reaction temperature is 30-40 ℃, the reaction time is 12-24h, and the drying temperature is 80-100 ℃.
3. The method for preparing monodisperse yttrium-90 polymer microspheres according to claim 1, wherein S12 is prepared by adding chloracetyl chloride functional group polymer microspheres into sodium hydroxide solution, refluxing, cleaning and drying.
4. The method for preparing monodisperse yttrium-90 polymer microspheres according to claim 1, wherein in S13, hydroxyl polymer microspheres are added into ceric ammonium nitrate solution, glycidyl methacrylate is added for reaction for 5-10 hours, and after the reaction, surface grafting GMA polymer microspheres are prepared by washing.
5. The method for preparing monodisperse yttrium-90 polymer microspheres according to claim 1, wherein sodium iminodiacetate is prepared in step S14, then surface grafted GMA polymer microspheres are added, and after reaction, the microspheres with surface chelated carboxyl functional groups are prepared by washing, wherein the reaction temperature is 50-60 ℃ and the reaction time is 12-24 hours.
6. The method for preparing monodisperse yttrium-90 polymer microspheres according to claim 1, wherein the polymer microspheres in S1 have a particle size of 100nm-100 μm and a pore size of 50-2000 angstrom.
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