KR20150007051A - Injectable agent comprising biocompatible polymers for tissue repair treatment - Google Patents
Injectable agent comprising biocompatible polymers for tissue repair treatment Download PDFInfo
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- KR20150007051A KR20150007051A KR20130080932A KR20130080932A KR20150007051A KR 20150007051 A KR20150007051 A KR 20150007051A KR 20130080932 A KR20130080932 A KR 20130080932A KR 20130080932 A KR20130080932 A KR 20130080932A KR 20150007051 A KR20150007051 A KR 20150007051A
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- polyethylene glycol
- polycaprolactone
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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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
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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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/60—Materials for use in artificial skin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/16—Compositions of unspecified macromolecular compounds the macromolecular compounds being biodegradable
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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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
Abstract
Description
More particularly, the present invention relates to a material for tissue repair, and more particularly, to a tissue-repairing material which is biodegradable, which is capable of thermosensitive phase transition at a room temperature or at a temperature below a refrigeration temperature, A polymeric aqueous solution, or an injectable injecting agent comprising an aqueous biocompatible polymer solution which maintains an injectable level of gel state. It maintains its volume after injection and can show efficacy immediately after the procedure, and the polymer induces tissue formation in vivo, and has the advantage of sustaining tissue restoration effect for a long time.
Many materials have been used as materials for skin repair. Collagen suspension was started to be used in 1981 as collagen was extracted and cultured in cattle. This product showed the efficacy of tissue repair by re-supplying collagen that disappeared in the body, but its effect was very limited because it was reabsorbed in the body within 1 month to 3 months due to the nature of collagen. Also, collagen extracted from animal Because of this, allergic reactions were observed in about 2% of the patients, and as a result, they are not in the limelight.
Currently, products using hyaluronic acid gel are forming the mainstream of the market. Hyaluronic acid was originally widely used as a raw material for ophthalmic solutions in ophthalmology. However, it has excellent biocompatibility even in the case of tissue regeneration.
However, since hyaluronic acid rapidly reabsorbs in vivo within 2 weeks to 2 months, it has recently been shown that a product that bridges hyaluronic acid and a cross-linking substance and extends the resorption time in vivo for up to 6 months, It is mainstream. However, such crosslinked products are also reported to have problems due to toxicity of crosslinked materials.
Although tissue repair techniques have been developed for extracting and re-transplanting adipocytes obtained from patients themselves, adipocytes also have problems because they are reabsorbed in vivo within a few weeks.
Recently, a number of products for tissue repair using a polymer that is not decomposed in vivo have been developed. One of them is a polymethylmethacrylate (PMMA) microsphere having a diameter of 20 to 40 쨉 m suspended in a gelatin solution or a collagen solution, PMMA has been reported to have many side effects due to long exposure in vivo.
Sanofi has developed a sculptor, a biodegradable biocompatible polymer microparticle, which is a biodegradable biodegradable product, which is mainly composed of polylactic acid. The biodegradation rate of the polymer is about 2 years, The restoration effect lasts about two years. This product is distinguished in that the injected polylactic acid exerts its effect on the patient's own tissue cells, while the hyaluronic acid or collagen product exerts its effects due to the hydrated volume of the inserted material. The polylactic acid microspheres or microparticles are suspended and injected into carboxymethylcellulose, wherein the microspheres or microparticles should have a diameter of 20 占 퐉 or more so as not to be attracted to the macrophage-phagocytic cells. On the other hand, the microspheres or fine particles must be less than 40 mu m in diameter so that they can be injected by fine needles and do not form granules under the fingers. Polylactic acid has been used as a material for facial trauma treatment in 1981 and has been used in various medical fields and its safety has been well proven. Carboxymethyl cellulose, which is used as a carrier gel, is not derived from animals and causes allergies It is unnecessary to confirm whether or not it is necessary. However, unlike collagen and hyaluronic acid products, this product does not exhibit its efficacy immediately after injection, and has a drawback that it exhibits its efficacy after about three months.
The biocompatible polymer aqueous solution, which is a technical field to which the present invention belongs, has been actively studied in the field of drug delivery systems. Particularly, the aqueous solution of a copolymer of polyethylene glycol and polypropylene oxide is a material in which a sol-gel gel phase is formed according to temperature and is developed and sold under the trade name of Pluronic and Poloxamer have.
In the case of these products, as the temperature of the triple polymer of hydrophilic polyethylene glycol and hydrophobic polypropylene oxide increases, the hydrogen bond between the polymer and the solvent is weakened, resulting in dehydration and the hydrophobic attraction between the polymers As a result, the sol-gel phase transition occurs depending on the temperature. When a hydrophilic group such as polyethylene glycol is introduced into a general polymer to dissolve in water, the hydrophilic group increases the solubility in water as the temperature increases. However, when a hydrophobic group such as polypropylene is introduced, And has a low critical solution temperature (LCST) in which water solubility is decreased. Therefore, a polymer composed of a hydrophilic part and a hydrophobic part has a hydrogen bonding force between a hydrophilic group and a water molecule of a polymer at a low temperature and dissolves in water to become a sol state. However, when the temperature is increased, the bonding power of the hydrophobic part of the polymer is dominant The hydrophobic part of the polymer coagulates and phase transition occurs in the gel state.
On the other hand, there is a disadvantage in that an aqueous solution prepared by using polyethylene glycol and a polypropylene oxide copolymer is injected into a living body and is not released to the outside of the body through biodegradation by metabolism. Therefore, polylactide as a biodegradable polymer chain A variety of polymers have been developed that incorporate polyglycolide copolymers (PLGA) and polycaprolactone (PCL).
The biocompatible polymer aqueous solution developed so far has been developed as a delivery material for gradually releasing drugs from the body. In the present invention, the biocompatible polymer aqueous solution was developed as a tissue repair material.
The inventors of the present invention have developed a biocompatible polymer aqueous solution capable of thermally responsive phase transformation or a biocompatible polymer aqueous solution maintaining an injectable gel state, which complement the disadvantages of existing tissue repair products described above Injection injecting agent was developed.
The injecting agent according to the present invention has an advantage of being excellent in biocompatibility, expecting the effect of restoration immediately after implantation of the organism, inducing tissue regeneration, and sustaining the tissue restoration effect for a long time.
In order to solve the above problems, the present invention provides a scanning injector for tissue repair comprising a biocompatible polymer aqueous solution, wherein the biocompatible polymer aqueous solution is in a sol state at room temperature or below a refrigeration temperature, Wherein the biocompatible polymer aqueous solution is a biocompatible polymer aqueous solution capable of maintaining temperature-responsive phase transition, or a biocompatible polymer aqueous solution maintaining an injectable level of gel state.
In the present invention, the biocompatible polymer may be a polyethylene glycol-polyester copolymer (poly (ethyleneglycol) / polyester); Chitosan / glycerol phosphate; Polyphosphazene; Polycaprolactone; Polycarbonate; Poly (ethylene glycol) / poly (propylene glycol), (PEG / PPG)) copolymer, Polycyanoacrylate; Polyorthoesters; Poly (N- (2-hydroxyethyl) methacrylamide-lactate)); Poly (propylene phosphate)); Polymers developed using Polypeptides; Polyethylene glycol- (polylactic-glycolic acid) -polyethylene glycol triple polymer; (Polylactic-glycolic acid) -polyethylene glycol- (polylactic-glycolic acid) triple polymer; Polyethylene glycol-polycaprolactone-polyethylene glycol triple polymer; Polycaprolactone-polyethylene glycol-polycaprolactone triple polymers; Polyethylene glycol-polycaprolactone copolymers; And a methoxypolyethylene glycol-polycaprolactone copolymer, or a multiblock copolymer thereof.
More preferably, the biocompatible polymer according to the present invention is a polyethylene glycol- (polylactic-glycolic acid) -polyethylene glycol triple polymer; (Polylactic-glycolic acid) -polyethylene glycol- (polylactic-glycolic acid) triple polymer; Polyethylene glycol-polycaprolactone-polyethylene glycol triple polymer; Polycaprolactone-polyethylene glycol-polycaprolactone triple polymers; Polyethylene glycol-polycaprolactone copolymers; And a methoxypolyethylene glycol-polycaprolactone copolymer, or a multiblock copolymer thereof.
In addition, the biocompatible polymer according to the present invention has an average molecular weight of 1,000 to 1,000,000 g / mol. When the average molecular weight is less than 1,000 g / mol, decomposition in vivo is too rapid to be suitable for use as a tissue repair material. When the molecular weight exceeds 1,000,000 g / mol, the thermosensitive phase transition is difficult to occur. Is not formed.
The weight of the polymer in the biocompatible polymer aqueous solution according to the present invention is 1% to 70%, more preferably 5% to 50%. And more preferably 10% to 40%. If the weight of the polymer in the aqueous solution is less than 1%, the sol-gel phase transition according to the temperature does not occur. If the weight of the polymer in the aqueous solution is 70% or more, an injectable gel can not be formed.
The injection injecting agent according to the present invention has an advantage of being excellent in biocompatibility, anticipating the effect of tissue repair immediately after implantation, inducing tissue regeneration, and continuing the tissue restoration effect for a long time. Particularly, it has been newly found that a polymer aqueous solution injected induces the formation of a new tissue to form a capsule in which the tissue is surrounded by an aqueous solution of a polymer (see FIG. 4), that is, a tissue restoration effect is obtained through tissue formation. The injection injecting agent according to the present invention shows a tissue restoration effect after forming a gel after injection and can exhibit the function of inducing tissue formation just like the beauty filler preparation using conventional polymeric fine particles. Thus, the disadvantage of the beauty filler using the conventional polymer fine particles It can be overcome. On the other hand, a gel of a level that can be injected is very useful when it is necessary to form a desired shape by using a high capacity especially because a desired shape can be set simultaneously with the injection.
1 shows Sol-Gel transition according to the temperature of a biocompatible polymer aqueous solution capable of temperature sensitive phase transformation comprising a polymer of polycaprolactone-polyethylene glycol-polycaprolactone having a molecular weight of 3,000 g / mol .
Fig. 2 is a graph showing the sol formation state at 20 캜 and the gel formation state at 35 캜 of a biocompatible polymer aqueous solution capable of thermosensitive phase transformation comprising a polycaprolactone-polyethylene glycol-polycaprolactone block copolymer having a molecular weight of 3,000 g / Lt; / RTI >
Figure 3 is a graphical representation of a sol-gel (Gel) gel according to the temperature of a biocompatible polymer aqueous solution capable of thermosensitive phase transformation comprising a polymer of a polymer of polycaprolactone-polyethylene glycol-polycaprolactone 3 with a molecular weight of about 15,000 g / ) Transition.
Fig. 4 is a graph showing the results of the injection of 0.1 ml of a biocompatible polymer aqueous solution containing a methoxypolyethylene glycol-polycaprolactone block copolymer having a molecular weight of 2,700 g / mol, which is capable of temperature sensitive phase transformation, Restoration effect and tissue regenerated around the polymer.
FIG. 5 shows that a polymer aqueous solution containing a methoxypolyethylene glycol-polycaprolactone block copolymer having a molecular weight of 2,700 g / mol forms a gel which can be injected through a 21 gauge needle at room temperature.
Figure 6 shows the results obtained by injecting 3 ml of a biocompatible polymer aqueous solution, which forms a gelable gel containing a methoxypolyethylene glycol-polycaprolactone block copolymer having a molecular weight of 2,700 g / mol, It shows the effect of restoration of the organization at the time of week.
Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, this is for the purpose of clarifying the implementation of the invention to a person having ordinary skill in the art, and does not mean that the scope of the present invention is limited by these embodiments.
Example One. Polylactic glycolic acid - Polyethylene glycol - Polylactic glycolic acid Triple polymerized Temperature Sensitivity Phase transition Preparation of possible biocompatible polymer aqueous solutions
Polymerization was carried out for one day at a temperature of 120 ° C under catalytic conditions of polyethylene glycol (molecular weight 1,000 g / mol), d, l-lactide and glycolide monomer, and then recrystallized to obtain a purified polylactic glycolic acid -Polyethylene glycol-polylactic glycolic acid triple polymer polymer was obtained.
To make a biocompatible polymer aqueous solution capable of thermally responsive phase transformation, the polymer was added to an aqueous solution so as to have a weight of 15% in an aqueous solution and mixed, followed by stirring at a refrigeration temperature.
When the aqueous solution of the biocompatible polymer capable of allowing the thermosensitive phase transition prepared above to gradually increase in temperature from the refrigeration temperature, it can be observed that the aqueous solution in a sol state is transferred to an aqueous solution in a gel state at about 20 ° C to 25 ° C there was.
Example 2 . Polycaprolactone - Polyethylene glycol - Polycaprolactone Triple Polymerized Temperature Sensitivity Phase transition Preparation of possible biocompatible polymer aqueous solutions
Polyethylene glycol (molecular weight: 1,000 g / mol) and ε-caprolactone monomer were polymerized for one day at a temperature of 120 ° C. and then recrystallized to obtain a purified polycaprolactone-polyethylene glycol-polycaprolactone having a molecular weight of 3,000 g / mol To obtain a triple polymer polymer.
To make a biocompatible polymer aqueous solution capable of thermally responsive phase transformation, the polymer was added to an aqueous solution at a weight of 20% in an aqueous solution, and the polymer was dissolved at 70 캜, followed by stirring at a refrigeration temperature.
It can be observed that when the biocompatible polymer aqueous solution capable of the thermosensitive phase transition prepared above is gradually raised from the refrigerating temperature, the aqueous solution in the sol state is transferred to the aqueous gel state in the vicinity of 25 ° C to 30 ° C (Figs. 1 and 2).
Example 3 . Polycaprolactone - Polyethylene glycol - Polycaprolactone Multipopolymerization of the triple polymer Temperature Sensitivity Phase transition Preparation of possible biocompatible polymer aqueous solutions
To prepare a polymer of polycaprolactone-polyethylene glycol-polycaprolactone triplet polymer synthesized in Example 2, 100 g of the above-mentioned triple polymer was dissolved in 100 mL of anhydrous toluene, and 5.1 g Of succinyl chloride was added together with 15 mL of triethylamine and stirred at 60 DEG C for one day. After that, a multi-polymer polymer of a polymer of polycaprolactone-polyethylene glycol-polycaprolactone 3 having a molecular weight of about 15,000 g / mol .
To make a biocompatible polymer aqueous solution capable of thermally responsive phase transformation, the polymer was added to the aqueous solution at a weight ratio of 20%, and the polymer was dissolved at 70 ° C, followed by stirring at the refrigeration temperature.
When the aqueous biocompatible polymer solution capable of temperature-sensitive phase transition prepared above was gradually increased from the refrigerating temperature, it was observed that the aqueous solution in a sol state was transferred to an aqueous solution in a gel state at about 30 ° C.
Example 4 . Methoxypolyethylene glycol - Polycaprolactone block Copolymerized Temperature response castle Phase transition Preparation of possible biocompatible polymer aqueous solutions
A methoxypolyethylene glycol-polycaprolactone block copolymer having a molecular weight of 2,700 g / mol was prepared by polymerizing methoxypolyethylene glycol (molecular weight 750 g / mol) and epsilon -caprolactone monomer at room temperature under a catalyst, and then recrystallized to obtain a purified polymer .
In order to obtain a biocompatible polymer aqueous solution capable of thermally responsive phase transformation, the polymer was added to the aqueous solution at a weight ratio of 10% and stirred well. Then, the aqueous solution was stirred in an oven at 80 ° C for 1 hour and the aqueous solution was immediately lowered to 2 ° C A biocompatible polymer aqueous solution capable of temperature sensitive phase transition was prepared.
It was observed that when the biocompatible polymer aqueous solution capable of the temperature sensitive phase transition prepared above was slowly heated from the refrigeration temperature, it was present as an aqueous solution in a sol state at about 20 ° C and as a gel at about 35 ° C (Fig. 3).
In order to evaluate the safety and the efficacy of the prepared injection injecting agent, 0.1 ml of injection injecting agent was injected subcutaneously in the rat, and after 12 weeks, , And it was confirmed that a regenerated structure was formed around the polymer (Figure 4).
In addition, it was confirmed that the polymer synthesized above was added to water at 80 ° C. to a weight of 30% in an aqueous solution, stirred and mixed to form an injectable gel at room temperature (FIG. 5)
The above-described formulation has the advantage that the gel is formed even at room temperature, and the phenomenon of decomposition of the polymer in an aqueous solution in a sol state can be minimized. The above-mentioned injectable gel was confirmed to be injected through a 21-gauge injection needle as a result of subcutaneous injection of the rat, and it was confirmed that the effect of the tissue restoration was not different compared to injection with the sol state 3 ml of the polymer aqueous solution was injected into the hypodermic area of the rat to evaluate the safety and tissue repair effect of the prepared injectable biocompatible polymer solution. As a result, (Fig. 6). As shown in Fig. 6, the tissue repair effect was maintained even after one week.
Claims (7)
The biocompatible polymer may be,
Polyethylene glycol-polyester copolymers (poly (ethyleneglycol) / polyester);
Chitosan / glycerol phosphate;
Polyphosphazene;
Polycaprolactone;
Polycarbonate;
Poly (ethylene glycol) / poly (propylene glycol), (PEG / PPG) copolymer, polyethylene glycol-
Polycyanoacrylate;
Polyorthoesters;
Poly (N- (2-hydroxyethyl) methacrylamide-lactate));
Poly (propylene phosphate));
Polymers developed using Polypeptides;
Polyethylene glycol- (polylactic-glycolic acid) -polyethylene glycol triple polymer;
(Polylactic-glycolic acid) -polyethylene glycol- (polylactic-glycolic acid) triple polymer;
Polyethylene glycol-polycaprolactone-polyethylene glycol triple polymer;
Polycaprolactone-polyethylene glycol-polycaprolactone triple polymers;
Polyethylene glycol-polycaprolactone copolymers; And
Wherein the polymer is at least one polymer selected from the group consisting of methoxypolyethylene glycol-polycaprolactone copolymer, or a multiblock copolymer thereof.
The biocompatible polymer may be,
Polyethylene glycol- (polylactic-glycolic acid) -polyethylene glycol triple polymer;
(Polylactic-glycolic acid) -polyethylene glycol- (polylactic-glycolic acid) triple polymer;
Polyethylene glycol-polycaprolactone-polyethylene glycol triple polymer;
Polycaprolactone-polyethylene glycol-polycaprolactone triple polymers;
Polyethylene glycol-polycaprolactone copolymers; And
Wherein the polymer is at least one polymer selected from the group consisting of methoxypolyethylene glycol-polycaprolactone copolymer, or a multiblock copolymer thereof.
Wherein the biocompatible polymer has an average molecular weight of 1,000 to 1,000,000 g / mol.
Wherein the weight of the polymer in the biocompatible polymer aqueous solution is 1% to 70%.
Wherein the weight of the polymer in the biocompatible polymer aqueous solution is from 5% to 50%.
Wherein the weight of the polymer in the biocompatible polymer aqueous solution is 10% to 40%.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190073916A (en) * | 2017-12-19 | 2019-06-27 | 주식회사 테라시온 바이오메디칼 | Method for manufacturing device of temporary vascular closure |
| WO2019225789A1 (en) * | 2018-05-24 | 2019-11-28 | 주식회사 덱스레보 | Composition for tissue repair and manufacturing method therefor |
| KR102077078B1 (en) * | 2019-06-26 | 2020-02-14 | 주식회사 로즈랩 | Composition for tissue restoration containing biodegradable copolymer |
| WO2021162292A1 (en) * | 2020-02-13 | 2021-08-19 | 주식회사 로즈랩 | Composition for tissue restoration, comprising biodegradable polymeric copolymer |
| CN115317665A (en) * | 2022-08-12 | 2022-11-11 | 济南格莱威医疗科技有限公司 | Polyester particle composite temperature-sensitive in-situ gel subcutaneous implant |
| EP4043044A4 (en) * | 2019-11-22 | 2023-11-01 | Dexlevo Inc. | Tissue restoration composition |
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2013
- 2013-07-10 KR KR20130080932A patent/KR20150007051A/en active Search and Examination
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190073916A (en) * | 2017-12-19 | 2019-06-27 | 주식회사 테라시온 바이오메디칼 | Method for manufacturing device of temporary vascular closure |
| WO2019225789A1 (en) * | 2018-05-24 | 2019-11-28 | 주식회사 덱스레보 | Composition for tissue repair and manufacturing method therefor |
| KR102077078B1 (en) * | 2019-06-26 | 2020-02-14 | 주식회사 로즈랩 | Composition for tissue restoration containing biodegradable copolymer |
| EP4043044A4 (en) * | 2019-11-22 | 2023-11-01 | Dexlevo Inc. | Tissue restoration composition |
| WO2021162292A1 (en) * | 2020-02-13 | 2021-08-19 | 주식회사 로즈랩 | Composition for tissue restoration, comprising biodegradable polymeric copolymer |
| CN115317665A (en) * | 2022-08-12 | 2022-11-11 | 济南格莱威医疗科技有限公司 | Polyester particle composite temperature-sensitive in-situ gel subcutaneous implant |
| CN115317665B (en) * | 2022-08-12 | 2023-08-18 | 济南格莱威医疗科技有限公司 | Polyester particle composite temperature-sensitive instant gel subcutaneous implant |
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