CN101703786A - Natural macromolecular ultrafine fibrous membrane marked with radioactive nuclide and preparation method thereof - Google Patents
Natural macromolecular ultrafine fibrous membrane marked with radioactive nuclide and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a natural macromolecular ultrafine fibrous membrane marked with radioactive nuclide and a preparation method thereof. The preparation method mainly comprises the following steps: firstly, electrostatially spinning biodegradable and absorbable natural biological macromolecules to prepare a natural macromolecular ultrafine fibrous membrane; carrying out a crosslinking reaction on the surface of the natural macromolecular ultrafine fibrous membrane; introducing a bifunctional group binder to the natural macromolecular ultrafine fibrous membrane by a coupling reaction; and finally, realizing the load of radioactive nuclides in a natural macromolecular ultrafine fibrous membrane material by a chelation reaction. The natural macromolecular ultrafine fibrous membrane material marked with radioactive nuclide has favorable biocompatibility, can be implanted in a tumor in a human body or a lesion site after the resection of the tumor for killing residual tumor cells by the inner radiation action of the radioactive nuclides to realize the effect of adjuvant therapy; and the natural macromolecular ultrafine fibrous membrane material marked with radioactive nuclide can be biodegraded and absorbed on the other hand, thereby being a biological material with wide application prospects.
Description
Technical field
The invention belongs to the macromolecular ultrafine fibrous membrane field of containing radionuclide, particularly relate to natural macromolecular ultrafine fibrous membrane of a kind of radioisotope labeling and preparation method thereof.
Background technology
Generally diameter is called superfine fibre at the fiber below 5 microns, superfine fibre has characteristics such as porosity height, specific surface area height, is specially adapted to biomedical sector.Electrostatic spinning is that a kind of effect that utilizes high voltage electric field is prepared into yardstick in the processing technique of micron order to nano level superfine fibre with polymer solution or melt spinning, it is the most common means for preparing macromolecular ultrafine fibrous membrane at present, medical high polymer is processed into superfine fibre film, can be widely used in various fields such as tissue repair, cytoskeleton, pharmaceutical carrier, artificial skin.The nucleic internal-radiation therapy is a kind of very promising neoplasm targeted therapy means, but does not occur having the target administration carrier of generally acknowledged clinical efficacy so far yet.The super-fine fiber material of electrospinning is combined with the nucleic irradiation technology, can prepare the superfine fibre film of radioisotope labeling, the latter not only has super-fine fiber material light weight softness, prevents the effect of adhesion, and can excise the position by implantation tumour, the realization radionuclide is killed for the tumors remaining cell, at biomedical sector very wide application prospect is arranged.
Summary of the invention
The object of the present invention is to provide natural macromolecular ultrafine fibrous membrane of a kind of radioisotope labeling and preparation method thereof.
Above-mentioned purpose is achieved by the following technical solution:
A kind of natural macromolecular ultrafine fibrous membrane of radioisotope labeling is made up of the component of following weight portion: natural macromolecular ultrafine fibrous 100, double-functional group bridging agent 0～0.01, radionuclide 0～0.005; The double-functional group bridging agent by with natural macromolecular ultrafine fibrous membrane in amino coupled be incorporated into natural macromolecular ultrafine fibrous membrane; Radionuclide is fixed in the surface of natural macromolecular ultrafine fibrous membrane by sequestration by the double-functional group bridging agent.
Described natural macromolecular ultrafine fibrous molecular weight is 5～200,000, and diameter is 50nm～5000nm, is selected from collagen, gelatin, chitosan, the chitin any one.
Described double-functional group links agent and is selected from ethylenediaminetetraacetic acid (EDTA), diethylene triamine pentacetic acid (DTPA) (DTPA), diethylene triamine pentacetic acid (DTPA) dianhydride (DTPA dianhydride), four nitrogen tetraacethyl cyclododecanes (DOTA), vinyl phosphoric acid hydrogen diammonium diacetate (EDDA), three (an iodic acid base phenyl) phosphine (TPPTS), between dicarboxylic acids pyrimidine (PDA), to carboxylic acid pyrimidine (ISONIC), amino acid modified (right-succinamide) diethylamino phenyl alkene pentaacetic acid (DTPA-Bz-NH-SA-c (KRGDf)), amino acid modified in the aminocarbonyl phenyl diethylene triamine pentacetic acid (DTPA) (DTPA-Bz-NH-c (ERGDf)) any one.
Described radionuclide is selected from any one or a few among 111In, 64Cu, 67Cu, 90Y, 131I, 188Re, 153Sm, 161Tb, 177Lu, 153Sm, 165Dy, 123I, 99Tc, the 68Ga.
The preparation method of the natural macromolecular ultrafine fibrous membrane of above-mentioned radioisotope labeling: earlier the natural biological macromolecule is carried out electrostatic spinning and prepare natural macromolecular ultrafine fibrous membrane, carry out cross-linking reaction on the natural macromolecular ultrafine fibrous membrane surface again, through coupling reaction double-functional group is linked agent then and introduce natural macromolecular ultrafine fibrous membrane, realize the load of radionuclide in the natural macromolecular ultrafine fibrous membrane material by chelatropic reaction at last, prepare the natural macromolecular ultrafine fibrous membrane of radioisotope labeling.
Concrete step is as follows:
(1) natural polymer is dissolved in the corresponding spin solvent, is mixed with mass percentage concentration and is 1%～100% natural polymer electrostatic spinning solution;
The pairing solvent of different natural macromolecular materials is respectively: collagen water-soluble or the mixed liquor of water and dimethyl acetylamide or the mixed liquor of water and dimethyl formamide, gelatin water-soluble or the mixed liquor of water and alcoholic acid mixed liquor or water and acetone or the mixed liquor of water and oxolane, chitosan is dissolved in aqueous formic acid or acetic acid aqueous solution, and chitin is dissolved in aqueous formic acid or acetic acid aqueous solution;
(2) electrostatic spinning solution of step (1) is packed in the charging gear of electrospinning device, distance to 5～25cm between the spinning head of adjustment charging gear and the catcher of ground connection, the ambient temperature of spinning is 20 ℃～70 ℃, and the air velocity in the environment is 0～8.5m
3/ hr; Opening high voltage power supply and charging gear pump, is that 15～30KV, feeding rate are to carry out electrostatic spinning under the condition of 5～300ul/min at voltage, and the injection stream of spinning solution is ejected on the catcher, promptly obtains natural macromolecular ultrafine fibrous membrane on catcher;
(3) natural macromolecular ultrafine fibrous membrane of step (2) being immersed concentration is that (consumption of every 1g natural macromolecular ultrafine fibrous membrane correspondence ethanol water or dehydrated alcohol is 20～2000ml) in the ethanol water or dehydrated alcohol 80% or more, add cross-linking agent, making the concentration of cross-linking agent in mixed solution is 1～200mmol/L, in 0～40 ℃ of cross-linking reaction 10～48 hours, a large amount of deionized water wash of reuse was until removing remaining cross-linking agent fully;
(4) natural macromolecular ultrafine fibrous membrane behind step (3) crosslinked is immersed in the special solution I that contains the double-functional group bridging agent, make double-functional group link agent and natural macromolecular ultrafine fibrous in amino carry out coupling reaction, reaction temperature is 0～50 ℃, and the response time is 10～120min; After finishing, reaction use deionized water wash until removing remaining double-functional group bridging agent fully, drier 1～5h in vacuum drying oven (room temperature);
(5) (radioactivity of every 20ul buffer solution is among the 0.005mCi～5mCi), every 2.25cm the natural macromolecular ultrafine fibrous membrane that contains the double-functional group bridging agent of step (4) to be immersed in acetic acid-sodium acetate buffer solution of the pH5.4 that contains radionuclide
2The amount of the corresponding buffer solution of the natural macromolecular ultrafine fibrous membrane that contains the double-functional group bridging agent be 20ul, under 0～50 ℃ condition, carry out sequestration reaction 10min～3h, radionuclide is fixed on natural macromolecular ultrafine fibrous surface by the double-functional group bridging agent by sequestration, the isotope superfine fibre film that taken out sequestration, earlier with acetic acid-sodium acetate buffer solution flushing, a large amount of deionized water rinsings of reuse, promptly obtain the natural macromolecular ultrafine fibrous membrane of radioisotope labeling of the present invention, thickness is 10～200 microns.
The spin solvent of described step (1) is any mixed solvent that two or more is formed according to any proportioning in water, formic acid, acetic acid, ethanol, acetone, dimethyl formamide, dimethyl acetylamide, the oxolane.
The cross-linking agent of described step (3) is the mixture that carbodiimide or carbodiimide and N-hydroxy-succinamide are formed according to 1: 1 mol ratio, perhaps is in glutaraldehyde, formaldehyde, diepoxides, the divinylsulfone any one.
The solution I of described step (4) is that concentration is the NaHCO of 50mM
3Aqueous solution or the mixed solution that is configured to according to 1: 1 volume ratio of the concentration dehydrant aqueous solution that is 50mM～200mM or aforementioned two kinds of solution; Also contain the double-functional group bridging agent that concentration is 1mg/ml～10mg/ml in the solution I simultaneously.
Further, described dehydrant is mixture or three chloro cyanuric acids (TCICA) or (2 that carbodiimide class and N-hydroxy-succinamide (NHS) are formed according to 1: 1 mol ratio, 4,6-three chloros)-1,3,5-triazines or (2,4,6-three chloros)-derivant of 1,3,5-triazines.
Preferably, described carbodiimide class is dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC).
Preferably, described (2,4,6-three chloros)-derivant of 1,3,5-triazines is a 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) or fluoridize (2-chloro-4, two (heptadecane fluoro oxygen in the ninth of the ten Heavenly Stems bases)-1 of 6-, 3,5-triazine (FCDMT) or (4-(4, the 6-dimethoxy-triazine)-4-methyl morpholine chloride (DMTMM) or (4-(4, the 6-dimethoxy-triazine)-4-methyl morpholine tetrafluoro is for borate.
The present invention combines electrostatic spinning process, radiobiology, cytobiology, oncology's ultimate principle, with the natural polymer that has good biocompatibility and be easy to chelating is primary raw material, by a kind of simple, efficient, practical, safe method, prepare the natural macromolecular ultrafine fibrous membrane material of radioisotope labeling.The natural macromolecular ultrafine fibrous membrane material of radioisotope labeling of the present invention in can implant into body tumor or the lesions position behind the tumor resection, by the residual tumor cell of the internal radiation action kill of lonizing radiation nucleic, and biodegradable and absorption, thereby playing the effect of auxiliary treatment, is a kind of biomaterial with broad prospect of application.
Description of drawings
Fig. 1 is the SEM figure of the chitosan superfine fibre film that obtains behind embodiment 1 electrostatic spinning.
The specific embodiment
Below in conjunction with embodiment the present invention is described in further detail, but is not to be limitation of the invention further, foregoing according to the present invention is made other forms of change, replacement etc. and is all belonged to scope of the present invention.
Embodiment 1:
(1) 0.5g chitosan (deacetylation greater than 97%, molecular weight 200,000) is dissolved in the mixed solvent of 10ml acetic acid and water (volume ratio of acetic acid and water is 9: 1), is mixed with the chitosan mass percentage concentration and is 5% electrostatic spinning solution;
(2) electrostatic spinning solution of step (1) is packed in the feed injector of electrospinning device, select the double-spinneret device that is connected with syringe for use, select for use swing roller as catcher; The distance of regulating between double-spinneret and the swing roller is 12cm, and the ambient temperature of spinning is 25 ℃, and the air velocity in the environment is controlled at 0.5～0.8m
3/ hr; Open high voltage power supply and feed injector pump, under the condition of voltage 20KV, feeding rate 20ul/min, carry out electrostatic spinning, on swing roller, obtain the chitosan superfine fibre film, it is carried out electron-microscope scanning to observe its microscopic appearance, gained SEM picture as shown in Figure 1, fibre structure homogeneous as can be seen, diameter is between 200nm～500nm;
(3) the chitosan superfine fibre film of step (2) being cut into area is 2.25cm
2Fritter, be immersed in 10ml concentration and be in 80% the ethanol water, add the cross-linking agent carbodiimide again in solution, making the concentration of carbodiimide in mixed solution is 100mM, in 4 ℃ of cross-linking reactions 10 hours, then with a large amount of deionized water wash until removing remaining carbodiimide fully;
(4) the chitosan superfine fibre film behind step (3) crosslinked is immersed in the NaHCO that 5ml concentration is 50mM
3In the aqueous solution (wherein containing 50mg DTPA), make amino and DTPA in the chitosan superfine fibre carry out coupling, be to react 2h under 0 ℃ the condition in temperature, then with deionized water wash until removing remaining DTPA, dry 3h in vacuum drying oven (room temperature) more fully;
(5) the chitosan superfine fibre film that contains DTPA of step (4) is immersed in acetic acid-sodium acetate buffer solution (wherein containing the active isotope 99YC13 of 3mCi that is) of 20ulpH5.4, isotope 99YC13 is fixed on chitosan superfine fibre surface by DTPA by sequestration after reacting 30min under the room temperature, the chitosan superfine fibre film of isotope 99YC13 that taken out sequestration, with acetic acid-sodium acetate buffer solution flushing, a large amount of deionized water rinsings of reuse, promptly obtain the chitosan superfine fibre film of isotope 99YC13 labelling earlier.
With the position behind the chitosan superfine fibre film implant surgery tumor resection of above-mentioned isotope 99YC13 labelling, find that this film has good adhesion inhibiting properties and tumor is killed performance, and can biodegradation and absorption.
Claims (7)
1. the natural macromolecular ultrafine fibrous membrane of a radioisotope labeling, it is characterized in that: by natural macromolecular ultrafine fibrous, the double-functional group bridging agent of 0～0.01 weight portion of 100 weight portions and the radionuclide component of 0～0.005 weight portion, the double-functional group bridging agent by with natural macromolecular ultrafine fibrous membrane in amino coupled be incorporated into natural macromolecular ultrafine fibrous membrane, radionuclide is fixed in the surface of natural macromolecular ultrafine fibrous membrane by sequestration by the double-functional group bridging agent;
Described natural macromolecular ultrafine fibrous molecular weight is 5～200,000, and diameter is 50nm～5000nm, is selected from collagen, gelatin, chitosan, the chitin any one;
Described double-functional group links agent and is selected from ethylenediaminetetraacetic acid (EDTA), diethylene triamine pentacetic acid (DTPA) (DTPA), diethylene triamine pentacetic acid (DTPA) dianhydride (DTPA dianhydride), four nitrogen tetraacethyl cyclododecanes (DOTA), vinyl phosphoric acid hydrogen diammonium diacetate (EDDA), three (an iodic acid base phenyl) phosphine (TPPTS), between dicarboxylic acids pyrimidine (PDA), to carboxylic acid pyrimidine (ISONIC), amino acid modified (right-succinamide) diethylamino phenyl alkene pentaacetic acid (DTPA-Bz-NH-SA-c (KRGDf)), amino acid modified in the aminocarbonyl phenyl diethylene triamine pentacetic acid (DTPA) (DTPA-Bz-NH-c (ERGDf)) any one;
Described radionuclide is selected from any one or a few among 111In, 64Cu, 67Cu, 90Y, 131I, 188Re, 153Sm, 161Tb, 177Lu, 153Sm, 165Dy, 123I, 99Tc, the 68Ga.
2. the natural macromolecular ultrafine fibrous membrane of radioisotope labeling according to claim 1 is characterized in that, described double-functional group bridging agent is 0.0002～0.01 weight portion, and described radionuclide is 0.00005～0.005 weight portion.
3. the natural macromolecular ultrafine fibrous membrane of radioisotope labeling according to claim 1 is characterized in that, thickness is 10～200 microns.
4. the preparation method of the natural macromolecular ultrafine fibrous membrane of the described radioisotope labeling of claim 1 is characterized in that, comprises the steps:
(1) natural polymer is dissolved in the corresponding spin solvent, is mixed with mass percentage concentration and is 1%～100% natural polymer electrostatic spinning solution;
(2) electrostatic spinning solution of step (1) is packed in the charging gear of electrospinning device, distance to 5～25cm between the spinning head of adjustment charging gear and the catcher of ground connection, the ambient temperature of spinning is 20 ℃～70 ℃, and the air velocity in the environment is 0～8.5m
3/ hr; Opening high voltage power supply and charging gear pump, is that 15～30KV, feeding rate are to carry out electrostatic spinning under the condition of 5～300ul/min at voltage, and the injection stream of spinning solution is ejected on the catcher, promptly obtains natural macromolecular ultrafine fibrous membrane on catcher;
(3) natural macromolecular ultrafine fibrous membrane of step (2) being immersed concentration is that (consumption of every 1g natural macromolecular ultrafine fibrous membrane correspondence ethanol water or dehydrated alcohol is 20～2000ml) in the ethanol water or dehydrated alcohol 80% or more, add cross-linking agent, making the concentration of cross-linking agent in mixed solution is 1～200mmol/L, in 0～40 ℃ of cross-linking reaction 10～48 hours, a large amount of deionized water wash of reuse was until removing remaining cross-linking agent fully;
(4) natural macromolecular ultrafine fibrous membrane behind step (3) crosslinked is immersed in the special solution I that contains the double-functional group bridging agent, make double-functional group link agent and natural macromolecular ultrafine fibrous in amino carry out coupling reaction, reaction temperature is 0～50 ℃, and the response time is 10～120min; After finishing, reaction use deionized water wash until removing remaining double-functional group bridging agent fully, drier 1～5h in vacuum drying oven (room temperature);
(5) (radioactivity of every 20ul buffer solution is among the 0.005mCi～5mCi), every 2.25cm the natural macromolecular ultrafine fibrous membrane that contains the double-functional group bridging agent of step (4) to be immersed in acetic acid-sodium acetate buffer solution of the pH5.4 that contains radionuclide
2The amount of the corresponding buffer solution of the natural macromolecular ultrafine fibrous membrane that contains the double-functional group bridging agent be 20ul, under 0～50 ℃ condition, carry out sequestration reaction 10min～3h, radionuclide is fixed on natural macromolecular ultrafine fibrous surface by the double-functional group bridging agent by sequestration, promptly obtain the natural macromolecular ultrafine fibrous membrane of radioisotope labeling of the present invention, thickness is 10～200 microns;
The spin solvent of described step (1) is any mixed solvent that two or more is formed according to any proportioning in water, formic acid, acetic acid, ethanol, acetone, dimethyl formamide, dimethyl acetylamide, the oxolane;
The cross-linking agent of described step (3) is the mixture that carbodiimide or carbodiimide and N-hydroxy-succinamide are formed according to 1: 1 mol ratio, perhaps is in glutaraldehyde, formaldehyde, diepoxides, the divinylsulfone any one;
The solution I of described step (4) is that concentration is the NaHCO of 50mM
3Aqueous solution or the mixed solution that is configured to according to 1: 1 volume ratio of the concentration dehydrant aqueous solution that is 50mM～200mM or aforementioned two kinds of solution; Also contain the double-functional group bridging agent that concentration is 1mg/ml～10mg/ml in the solution I simultaneously.
5. the preparation method of the natural macromolecular ultrafine fibrous membrane of radioisotope labeling according to claim 4, it is characterized in that, described dehydrant is mixture or three chloro cyanuric acids (TCICA) or (2,4,6-three chloros)-1 that carbodiimide class and N-hydroxy-succinamide (NHS) are formed according to 1: 1 mol ratio, 3,5-triazine or (2,4,6-three chloros)-1,3, the derivant of 5-triazine.
6. the preparation method of the natural macromolecular ultrafine fibrous membrane of radioisotope labeling according to claim 5, it is characterized in that described carbodiimide class is dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC).
7. the preparation method of the natural macromolecular ultrafine fibrous membrane of radioisotope labeling according to claim 5, it is characterized in that, described (2,4,6-three chloros)-1,3, the derivant of 5-triazine is a 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) or fluoridize (2-chloro-4, two (heptadecane fluoro oxygen in ninth of the ten Heavenly Stems base)-1,3,5-triazines (FCDMT) of 6-or (4-(4, the 6-dimethoxy-triazine)-4-methyl morpholine chloride (DMTMM) or (4-(4, the 6-dimethoxy-triazine)-4-methyl morpholine tetrafluoro is for borate.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101843578B (en) * | 2010-05-14 | 2012-05-23 | 东华大学 | Nanofiber membrane carrying anti-tumor photosensitizer and preparation method thereof |
| CN109853233A (en) * | 2019-02-12 | 2019-06-07 | 中国科学技术大学 | A kind of modified poly ethylene nano fibrous membrane and preparation method thereof |
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| CN101301496B (en) * | 2007-05-08 | 2011-07-20 | 中国科学院化学研究所 | Biodegradable and absorbable polymer superfine fibre film with radioactive nuclide marker and preparation and use thereof |
| CN101358382A (en) * | 2008-08-26 | 2009-02-04 | 东华大学 | Antibacterial nano fiber material and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101843578B (en) * | 2010-05-14 | 2012-05-23 | 东华大学 | Nanofiber membrane carrying anti-tumor photosensitizer and preparation method thereof |
| CN109853233A (en) * | 2019-02-12 | 2019-06-07 | 中国科学技术大学 | A kind of modified poly ethylene nano fibrous membrane and preparation method thereof |
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