CN108236736A - A kind of synthetic method of Polyvinyl Alcohol Embolization microballoon for carrying chemotherapeutic epirubicin - Google Patents
A kind of synthetic method of Polyvinyl Alcohol Embolization microballoon for carrying chemotherapeutic epirubicin Download PDFInfo
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- CN108236736A CN108236736A CN201611231190.3A CN201611231190A CN108236736A CN 108236736 A CN108236736 A CN 108236736A CN 201611231190 A CN201611231190 A CN 201611231190A CN 108236736 A CN108236736 A CN 108236736A
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- epirubicin
- polyvinyl alcohol
- microballoon
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
- A61L24/0015—Medicaments; Biocides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
Abstract
A kind of Polyvinyl Alcohol Embolization microballoon synthetic method for carrying chemotherapeutic epirubicin by studying the formula and synthesis technology of synthetic reaction, improves drugloading rate of the Polyvinyl Alcohol Embolization microballoon to epirubicin, including following drip irrigation device：Polyvinyl alcohol is completely dissolved postcooling and is cooled to 10~15 DEG C, the ratio of 2 methyl propane sulfonic acid sodium of Calli B and 2 acrylamide is 1.00: 0.15, agitating paddle selects axial flow type agitating valve, mixing speed control temperature of reaction system in 400rpm, polymer monomer solution addition is controlled at 40~50 DEG C.This method is by studying formula, agitating mode, mixing speed and the reaction temperature of synthetic reaction, solve the problems, such as that Polyvinyl Alcohol Embolization microballoon is relatively low to the medicine-carried amount of epirubicin, increase drugloading rate of the microballoon to epirubicin, carry the microballoon of medicine constantly can discharge epirubicin in tumor locus to cancer target area.
Description
Technical field
The present invention relates to a kind of Polyvinyl Alcohol Embolization microballoon synthetic methods for carrying chemotherapeutic epirubicin, belong to medical material
Expect technical field.
Background technology
Minimally Interventional Therapy method is particularly rich in blood vessel in field of medical technology in such as liver cancer, kidney and fibroid etc.
Cancer treatment in terms of just have been more and more widely used, and have become treatment and can not carry out the swollen of operation excision
The preferred alternative solution of knurl.Its principle is by high-definition medical image instrument, and guiding catheter is reached by artery in human body
Tumor locus, then reach the blood supply for blocking tumor tissues by the suppository of catheter perfusion antitumor drug, so as to make tumour
The therapeutic purposes of atrophy, necrosis in a short time.The key of minimally invasive interventional therapy is to select suitably to be used to that tissue to be blocked to supply
The suppository of blood, the physical characteristic of suppository is most important to the final curative effect of interventional therapy operation, oversized or size point
Cloth is wide, and suppository product in irregular shape can cause intervention following problems occur in performing the operation：(1) obstruction conduit；(2) accidentally
Bolt, i.e. embolism point cause the damage of normal tissue apart from tumor tissues too far；(3) it drifts about, i.e., suppository leaves after surgery
Scheduled embolism position enters other blood vessels；It (4) cannot embolism target blood completely.And embolic agents are reached using micro catheter
The end blood supply capilary of tumour then further improves Minimally Interventional Therapy to realize that the super choosing of Minimally Interventional Therapy is treated
Curative effect reduces the optimal path of the injury of normal tissue caused by due to missing bolt and drift, special to the type of suppository
It is not that the size of particle and the uniformity of shape have strict requirements.
Embolism microball is widely applied as a kind of novel particle suppository, and existing microballoon can be divided by material therefor
It is micro- for polyvinyl alcohol microparticles, spherex, albumin microsphere, gelatine microsphere, polylactic acid microsphere, sodium alginate micro ball, chitosan
Ball and ethyl cellulose microballoon etc..Although the shape of these microballoons is relatively more unified, surface is smooth, size is more uniform, and hydrophily,
Suspension is preferable, is easy to be oriented to blood flow, can the total cross-section of occluding vascular and it is uneasy to recur, but the microballoon wherein having does not have and stretches
Contracting and elasticity can be restored to original state it is difficult to deform and pass through micro catheter, can cause incomplete embolism quickly again, and have
Microsphere expansion coefficient is excessive, is difficult selection microballoon size, and without the visuality of X-ray examination, using effect is very not in application
Ideal can not meet to the super needs for selecting interventional treatment.
In recent years, tumour is treated using embolotherapy and anticancer drug chemotherapy combined, is connect extensively by interventional treatment field
By.Combination therapy is typically carried out with chemotherapeutics solution and suppository, it is dense by improving lesion and surrounding topical remedy
The effect of spending, while reduce Systemic drug concentrations, reducing toxic side effect, improve tumour.But the chemotherapeutic clinically used at present
The local drug delivery slow release of chemotherapeutics can not be completely secured due to being limited by suppository for object perfusion.
The tumour that embolism microball Intra-arterial embolization treats the excision that can not perform the operation has been considered as middle and advanced stage richness blood vessel in foreign countries
The preferred therapy of liver cancer.Polyvinyl Alcohol Embolization microballoon is the first generation production domesticization microspheric embolism of the permanent auspicious character used in proper names and in rendering some foreign names clever life in Suzhou
Agent, unique reticular structure, make it have quick adsorption simultaneously can slow release chemotherapeutics in vivo design function.Chemotherapeutic
Epirubicin is suitable for Several Kinds of Malignancy of the treatment including liver cancer.Embolism microball is made to adsorb chemotherapeutic epirubicin, is led to
The artery that super selection vessel catheter merging obstruction dominates tumor tissues is crossed, required for making microballoon that can not only block tumor cell proliferation
Blood supply source, and carry the microballoon of medicine tumor locus can constantly to cancer target area release anti-cancer medicine, targeting is strong,
It is minimally invasive, small to the toxic side effect of whole body other organs, to improving mid and late liver cancer disease quality of life of patients, extending life cycle, subtract
Few whole body toxic side effect is of great significance.
Invention content
The object of the present invention is to provide a kind of Polyvinyl Alcohol Embolization microballoon synthetic methods for carrying chemotherapeutic epirubicin, should
Method is by studying the formula and synthesis technology of synthetic reaction, to increase drugloading rate of the microballoon to epirubicin.
The present invention is achieved through the following technical solutions：
Polyvinyl alcohol is added in into the flask for fill pure water, is dispersed with stirring uniformly.96 DEG C are heated to, in polyvinyl alcohol
It after being completely dissolved, cools to 10~15 DEG C, adds in intermediate acrylamido alkyl dialkoxy acetal, N- third thereto
Acrylamide base dimethoxy-ethyl acetal, stirring after ten minutes, concentrated hydrochloric acid are added dropwise into solution, are reacted after completion of dropwise addition and continue to stir
It mixes 6 hours, then collects crude product, required function macromolecule hydrogel (abbreviation Calli-B) is obtained after washed drying.
2- acrylamide-2-methyl propane sulfonics sodium, potassium peroxydisulfate are sequentially added in water, dissolved, after mixing, is added in
Calli-B is simultaneously stirred evenly, and obtains polymer monomer solution.Acetic acid fourth vinegar, cellulose acetate are added in reaction vessel successively,
It is passed through N simultaneously2Gas stirs, and heating sequentially adds above-mentioned polymer monomer solution and tetramethylethylenediamine, forms grease
Hybrid reaction system, heating, stirring 3 hours.After reaction, microballoon is collected by filtration in reaction mixture, then uses second successively
Acid butyl ester, ethyl acetate and acetone washing, by being dried in vacuo, obtain microsphere type embolic agent.
Epirubicin is dissolved in pure water, above-mentioned microsphere type embolic agent is taken to be put into container, epirubicin solution is added in, makes
Microballoon is soaked in epirubicin solution, shakes mixing frequently, and after the reaction was complete, mixture is collected by filtration microballoon, is being passed through
After vacuum drying, the Polyvinyl Alcohol Embolization microballoon of loading drug epirubicin is obtained.
In above-mentioned technical proposal, after polyvinyl alcohol is completely dissolved, cool to 10~15 DEG C.
In above-mentioned technical proposal, the ratio of Calli-B and 2- acrylamide-2-methyl propane sulfonic sodium is 1.00: 0.15.
In above-mentioned technical proposal, agitating paddle selects axial flow type agitating valve.
In above-mentioned technical proposal, mixing speed is controlled in 400rpm.
In above-mentioned technical proposal, temperature of reaction system control is at 40~50 DEG C when polymer monomer solution adds in.
Compared with present technology, the beneficial effects of the present invention are：What invention was provided carries chemotherapeutic epirubicin
Polyvinyl Alcohol Embolization microballoon synthetic method be formula and technique by studying synthetic reaction, procedure is succinct, at low cost
It is honest and clean, drugloading rate of the existing Polyvinyl Alcohol Embolization microballoon to epirubicin can be effectively improved.Meanwhile the suppository shape of synthesis connects
Nearly perfect spheroidal, surface is smooth, compression deformation rate up to more than 50%, can be preserved in physiological saline at room temperature 2 years with
On.
Specific embodiment：
With reference to specific embodiment, the invention will be further described.
Embodiment 1：
Polyvinyl alcohol 150g is added in into the flask for fill pure water, is dispersed with stirring uniformly.96 DEG C are heated to, in poly- second
It after enol is completely dissolved, cools to after 10~15 DEG C, adds in the contracting of intermediate acrylamido alkyl dialkoxy thereto
Aldehyde 3.0g, N acrylamide base dimethoxy-ethyl acetal 3.0g, stirring after ten minutes, concentrated hydrochloric acid 100ml are added dropwise into solution,
Reaction continues stirring 6 hours after completion of dropwise addition, then collects crude product, required function macromolecular water is obtained after washed drying
Gel (abbreviation Calli-B).
Embodiment 2：
2- acrylamide-2-methyl propane sulfonic sodium 15g, potassium peroxydisulfate 10g are sequentially added in water, dissolving is uniformly mixed
Afterwards, it adds in functionalization macromolecular gel intermediate (Calli-B) 100.00g prepared by embodiment 1 and stirs evenly, polymerize
Object monomer solution.Acetic acid fourth vinegar 10g, cellulose acetate 5g are added in reaction vessel, while are passed through N2Gas stirs, heating,
Above-mentioned polymer monomer solution and tetramethylethylenediamine are sequentially added, forms oil mixing with water reaction system, heating, stirring 3 are small
When.In the reaction, agitating paddle selects axial flow type agitating valve, and mixing speed control is in 400rpm, polymer monomer solution addition
Temperature of reaction system is controlled at 40~50 DEG C.After reaction, microballoon is collected by filtration in reaction mixture, then uses acetic acid successively
Butyl ester, ethyl acetate and acetone washing, by being dried in vacuo, obtain microsphere type embolic agent.
Embodiment 3：
10mg epirubicins are dissolved in 2.0ml pure water, the microsphere type embolic agent synthesized in Example 2 accurately weighs
0.25g is put into 20ml cillin bottles, is added in above-mentioned epirubicin solution 2ml, microballoon is made to be soaked in epirubicin solution, no
When shake mixing.With micro syringe the 5th, 10,20,40,20 μ L of 60min timing samplings, add in 5.0ml pure water and dilute,
Absorbance is measured at 485nm, absorbance is substituted into calibration curve equation, the concentration of sample contained drug is calculated, so as to calculate
Microballoon is to the drugloading rate of epirubicin：Drugloading rate=(solution content of dispersion after solution content of dispersion-load medicine before load medicine)/microspheres weight.
Measure microballoon load table it is soft than spaceborne dose be every gram of microballoon of 38mg/.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar can understand present disclosure and implement according to this, and it is not intended to limit the scope of the present invention.It is all according to the present invention
The equivalent change or modification that Spirit Essence is made, should be covered by the protection scope of the present invention.
Claims (7)
1. a kind of Polyvinyl Alcohol Embolization microballoon synthetic method for carrying chemotherapeutic epirubicin, it is characterized in that anti-by studying synthesis
The formula and synthesis technology answered improve drugloading rate of the Polyvinyl Alcohol Embolization microballoon to epirubicin.
2. the synthetic method of Polyvinyl Alcohol Embolization microballoon according to claim 1 for carrying chemotherapeutic epirubicin, special
Sign is that the preparation process is as follows：
Polyvinyl alcohol is added in into the flask for fill pure water, is dispersed with stirring uniformly.It is heated to 96 DEG C, it is complete in polyvinyl alcohol
It after dissolving, cools to 10~15 DEG C, adds in intermediate acrylamido alkyl dialkoxy acetal, N- acryloyls thereto
Amido dimethoxy-ethyl acetal, stirring after ten minutes, concentrated hydrochloric acid are added dropwise into solution, are reacted after completion of dropwise addition and continue stirring 6
Hour, crude product is then collected, required function macromolecule hydrogel (abbreviation Calli-B) is obtained after washed drying.
2- acrylamide-2-methyl propane sulfonics sodium, potassium peroxydisulfate are sequentially added in water, dissolved, after mixing, is added in
Calli-B is simultaneously stirred evenly, and obtains polymer monomer solution.Acetic acid fourth vinegar, cellulose acetate are added in reaction vessel successively,
It is passed through N simultaneously2Gas stirs, and heating sequentially adds above-mentioned polymer monomer solution and tetramethylethylenediamine, forms grease
Hybrid reaction system, heating, stirring 3 hours.After reaction, microballoon is collected by filtration in reaction mixture, then uses second successively
Acid butyl ester, ethyl acetate and acetone washing, by being dried in vacuo, obtain microsphere type embolic agent.
Epirubicin is dissolved in pure water, above-mentioned microsphere type embolic agent is taken to be put into container, epirubicin solution is added in, makes microballoon
It is soaked in epirubicin solution, shakes mixing frequently, after the reaction was complete, microballoon is collected by filtration in mixture, by vacuum
After drying, the Polyvinyl Alcohol Embolization microballoon of loading drug epirubicin is obtained.
3. a kind of Polyvinyl Alcohol Embolization microballoon synthetic method for carrying chemotherapeutic epirubicin according to claim 2,
After being characterized in that the polyvinyl alcohol is completely dissolved, cool to 10~15 DEG C.
4. a kind of Polyvinyl Alcohol Embolization microballoon synthetic method for carrying chemotherapeutic epirubicin according to claim 2,
The ratio for being characterized in that Calli-B the and 2- acrylamide-2-methyl propane sulfonics sodium is 1.00: 0.15.
5. a kind of Polyvinyl Alcohol Embolization microballoon synthetic method for carrying chemotherapeutic epirubicin according to claim 2,
It is characterized in that the agitating paddle selects axial flow type agitating valve.
6. a kind of Polyvinyl Alcohol Embolization microballoon synthetic method for carrying chemotherapeutic epirubicin according to claim 2,
It is characterized in that the mixing speed control in 400rpm.
7. a kind of Polyvinyl Alcohol Embolization microballoon synthetic method for carrying chemotherapeutic epirubicin according to claim 2,
It is characterized in that temperature of reaction system control is at 40~50 DEG C when the polymer monomer solution adds in.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611231190.3A CN108236736A (en) | 2016-12-26 | 2016-12-26 | A kind of synthetic method of Polyvinyl Alcohol Embolization microballoon for carrying chemotherapeutic epirubicin |
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| CN201611231190.3A CN108236736A (en) | 2016-12-26 | 2016-12-26 | A kind of synthetic method of Polyvinyl Alcohol Embolization microballoon for carrying chemotherapeutic epirubicin |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108992431A (en) * | 2018-09-30 | 2018-12-14 | 重庆医科大学附属永川医院 | A kind of Doxorubicin embolism microball and preparation method thereof |
| CN110327300A (en) * | 2019-07-23 | 2019-10-15 | 赵修文 | A kind of polyvinyl alcohol microparticles of carrying medicament |
| CN113350298A (en) * | 2021-06-11 | 2021-09-07 | 复旦大学附属中山医院 | Preparation method of drug-loaded microspheres |
-
2016
- 2016-12-26 CN CN201611231190.3A patent/CN108236736A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108992431A (en) * | 2018-09-30 | 2018-12-14 | 重庆医科大学附属永川医院 | A kind of Doxorubicin embolism microball and preparation method thereof |
| CN108992431B (en) * | 2018-09-30 | 2020-10-09 | 重庆医科大学附属永川医院 | Doxorubicin embolism microsphere and preparation method thereof |
| CN110327300A (en) * | 2019-07-23 | 2019-10-15 | 赵修文 | A kind of polyvinyl alcohol microparticles of carrying medicament |
| CN113350298A (en) * | 2021-06-11 | 2021-09-07 | 复旦大学附属中山医院 | Preparation method of drug-loaded microspheres |
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Application publication date: 20180703 |