KR101622545B1 - Acne treatment composition and method for manufacturing acne treatment preparation using the same - Google Patents
Acne treatment composition and method for manufacturing acne treatment preparation using the same Download PDFInfo
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Abstract
The present invention discloses a composition comprising a nano-ion complex for photodynamic therapy and a method for preparing a composition comprising a nano-ion complex for photodynamic therapy. One embodiment of the present invention is a composition comprising a nano-ion complex for photodynamic therapy comprising a copolymer of a hydrophilic cationic polymer and a photosensitizer combined and a conjugate of an anionic substrate polymer and a photoinitiator, wherein the copolymer comprises polyethylene glycol - polyethylenimine-pheophorbide A, said conjugate being a chondroitin sulfate-blackhole quencher (BHQ), wherein said photodynamic therapy nano-ion complex is present in excess of 0 and 1 milligram Or less.
Description
One embodiment of the present invention relates to a composition comprising a nanocomposite for photodynamic therapy and a method for preparing a composition comprising a nanocomposite for photodynamic therapy.
Although skin diseases do not interfere with life, they occur frequently, and modern people are becoming more and more common due to various causes, climate, and stress.
In particular, acne is an intractable skin disease caused by fungal and bacterial infections, which requires a long term treatment period and is difficult to treat.
As a method for treating acne, hormones and antibiotics for suppressing sebum production are prescribed. These methods are somewhat effective in the prevention and treatment of acne, but side effects are questioned in terms of satisfactory efficacy and skin safety.
In the case of hormone drugs, it may cause adverse effects in long-term administration such as erythema and dryness of skin. Antibiotics such as benzoyl peroxide and retinoic acid cause problems of carcinogenicity and contact dermatitis have. In addition, tetracyclin, erythromycin, and clindamycin have been used for the treatment of acne, but it has been reported that there is a possibility of the occurrence of resistant bacteria.
On the other hand, photodynamic therapy (PDT) is a curative method such as a chemotherapeutic agent that can treat lesions without surgery using a photosensitizer with selectivity and photosensitivity to various lesions. For example, the photo-sensitive material is administered to a subject by intravenous injection, and a suitable light is irradiated to activate the photo-sensitive substance to convert oxygen molecules into singlet oxygen or to create new radicals The lesion is selectively attacked and collapsed.
As such photosensitizers, porphyrin compounds are representative, and porphyrin compounds extracted from dips, mulberry leaves, and green algae have spectroscopic properties suitable for use as photosensitizers, and red light having a relatively high cell permeability (700-900 nm) is known to be capable of efficiently generating the electron transferring property and thus the excited state.
One embodiment of the present invention is to provide a composition comprising a nano-ion complex for photodynamic therapy, which is harmless to the human body and does not cause side effects, and a method for producing a composition comprising the nano-ion complex for photodynamic therapy.
One embodiment of the present invention also relates to a composition comprising a nano-ion complex for photodynamic therapy comprising a photo-sensitive material having optical and disease target properties, and a method for preparing a composition comprising a nano-ion complex for photodynamic therapy .
One embodiment of the present invention is a composition for treating acne comprising a nano-ion complex for photodynamic therapy, which comprises a copolymer of a hydrophilic cationic polymer and a photosensitizer, and a combination of an anionic substrate polymer and a photoinitiator, Wherein the cohesion is polyethylene glycol-polyethyleneimine-pheophorbide A, and the conjugate is a chondroitin sulfate-blackhole quencher (BHQ), and the photodynamic therapy nano ion Lt; RTI ID = 0.0 > 0 < / RTI > and 1 milligram or less.
Wherein the composition comprises 0.1-10% by weight of an emulsifier, 0.1-10% by weight of a primary alcohol, 0.1-10% by weight of a secondary alcohol, 0.1-10% by weight of a fatty acid, 1-40% by weight of an oil %, And a remaining amount of purified water.
The emulsifier may be a nonionic surfactant having a structure of hydroxyl group (-OH), ether group (-O-), amide group (-CONH) and ester group (-COO-) in the molecule. Polyoxyethylene type, polyhydric alcohol ester type, ethylene oxide and propylene oxide block copolymer, polymeric surfactant of alkyl acrylate copolymer; Lecithin, lanolin, cholesterol, natural surfactants of saponin, and the like.
The first alcohol may be at least one selected from the group consisting of glycerin, propylene glycol, butyleneglycol, dipropylene glycol, polyethylene glycol, sorbitol, and combinations thereof.
The second alcohol is selected from the group consisting of lauryl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, linolenyl alcohol, arachidonyl An alcohol, an alcohol, an alcohol, or a combination thereof.
The fatty acid may be at least one selected from the group consisting of stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid, or a combination thereof.
Wherein the oil is selected from the group consisting of cyclodymethicone, dimethicone, diethylhexylcarbonate, hydrogenated polyhedrin, isopropyl myristate, liquid paraffin, vegetable squalane, macadamia nut oil, jojoba oil, avocado oil, olive oil, camellia oil, And combinations thereof.
In another embodiment of the present invention, there is provided a method for producing a therapeutic agent comprising a composition comprising the above-mentioned nano-ion complex for photodynamic therapy, which comprises heating an emulsifier, a primary alcohol and purified water to prepare a water- ; Heating the first alcohol, fatty acid, and oil to produce an oily raw material; Mixing the heated water raw material and the oil raw material; Neutralizing and cooling the mixture; And homogenizing the cooled mixture with a nanomechanical complex for photodynamic therapy.
According to one embodiment of the present invention, there can be provided a composition comprising a nano-ion complex for photodynamic therapy, which is harmless to the human body and does not cause side effects, and a method for producing a composition comprising the nano-ion complex for photodynamic therapy.
Also, according to one embodiment of the present invention, there is provided a composition comprising a nano-ion complex for photodynamic therapy (PDT) including a photosensitizing substance having optical characteristics and disease target characteristics, A method for producing a composition comprising a nano-ion complex for epidemiological therapy can be provided.
Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.
One embodiment of the present invention is a composition comprising a nano-ion complex for photodynamic therapy comprising a copolymer of a hydrophilic cationic polymer and a photosensitizer combined, and a combination of an anionic substrate polymer and a photoinitiator, wherein the copolymer is polyethylene Wherein the conjugate is a chondroitin sulfate-blackhole quencher (BHQ), wherein the photomechanical therapeutic nano-ion complex is greater than 0 and less than 1 < RTI ID = 0.0 > Milligrams or less.
The hydrophilic cationic polymer is selected from the group consisting of glycol chitosan, chitosan, poly-L-lysine (PLL), poly-beta-amino ester polymer, polyethyleneimine (PEI), polyamidoamine (PAMAM) dendrimer, , And the hydrophilic cationic polymer can form an ion complex nanoparticle by an electrostatic attraction with an anionic substrate polymer to be described later.
For example, the hydrophilic cationic polymer may include polyethylene glycol and polyethyleneimine.
At this time, the polyethylene glycol (PEG) has a structural formula represented by HO- (CH 2 CH 2 O) nH, and in this case, due to the structural characteristic of ethylene oxide ((CH 2 CH 2 O) -) It shows strong hydrophilicity. In addition, when such a property is combined with a protein or a compound, it has a characteristic of giving biocompatibility.
Also, polyethylene glycol is present in the form of methoxypolyethylene glycol (mPEG) in which one end is substituted with a methoxy group (CH 3 O-), and its structural formula is represented by CH 3 O- (CH 2 CH 2 O) n H do. Particularly, in the case of a preparation having a form of polyethylene glycol-protein, most methoxypolyethylene glycol derivatives are used as polyethylene glycol. This is because the terminal of the polyethylene glycol is protected by a methoxy group, so that the stability of the structure can be maintained.
In one embodiment of the present invention, the polyethylene glycol may be a polyethylene glycol having a terminal carboxyl group with a molecular weight of 300 to 50,000. Also, the polyethylene glycol may be methoxypolyethylene glycol having one terminal substituted with a methoxy group.
On the other hand, the polyethyleneimine is a cationic polymer electrolyte which has been used for a long time in the field of paper making. In general, polyethylene imine is divided into linear and branched depending on its structure, and the synthesis methods of the two are different. Commonly used polyethyleneimine is branched, and the number of primary amines, secondary amines, and tertiary amines is present in a ratio of 1: 2: 1. It is known that one branch of the branched polyethyleneimine exists in the range of about 3 to 3.5 of the main chain nitrogen atoms. Such polyethyleneimine is soluble in water, alcohol, glycol, dimethylformamide, tetrahydrofuran, It is known that it is not soluble in high molecular weight hydrocarbons, oleic acid and diethyl ether.
For example, the polyethyleneimine may be a branched polyethylenimine having no toxicity. When the molecular weight of the polyethyleneimine is less than 100, the copolymer produced according to the present invention can not bind to a useful physiologically active substance and has a molecular weight of 25,000 , There is a problem that it is difficult to be discharged from the body through the kidney in the body. Therefore, the polyethyleneimine may have a molecular weight of 100 to 25,000, preferably 100 to 2000.
The photosensitizer may be selected from the group consisting of a phorphyrins compound, a chlorins compound, a bacteriochlorins compound, a phthalocyanine compound, a naphthalocyanines compound, and a 5- 5-aminoevuline esters) compounds may be used. For example, the photosensitizer may be Chlorin e6, Zinc Phthalocyanine, or pheophorbide A.
The complex is formed in the form that the quencher is bonded to the anionic substrate polymer.
More specifically, the anionic substrate polymer is selected from the group consisting of chondroitin-6-sulfate (C6S), heparan sulfate (HS), heparan sulfate proteoglycan (HSPG), heparin, chondroitin- C6S), dermatan sulfate (DS), keratan sulfate (KS), and hyaluronic acid (HA).
The quencher may be selected from the group consisting of a blackhole quencher (BHQ), a blackberry quencher (BBQ), and derivatives thereof.
Accordingly, in the present invention, the cationic polymer, that is, the hydrophilic cationic polymer is used to impart hydrophilicity to the photosensitizer having hydrophobicity, so that it is well dissolved in a solution or water during optical treatment, so that no precipitate is formed.
Meanwhile, the composition comprising the nano-ion complex for photodynamic therapy according to an embodiment of the present invention comprises 0.1-10% by weight of an emulsifier; 0.1-10% by weight of primary alcohol; 0.1 to 10% by weight of a secondary alcohol; 0.1-10% by weight fatty acid; 1-40% by weight of oil; And a purified water of the remaining amount.
More specifically, the emulsifier is a nonionic surfactant having a structure of a hydroxyl group (-OH), an ether group (-O-), an amide group (-CONH) and an ester group (-COO-) in the molecule. Polyoxyethylene type, polyhydric alcohol ester type, ethylene oxide and propylene oxide block copolymer, polymeric surfactant of alkyl acrylate copolymer; Lecithin, lanolin, cholesterol, natural surfactants of saponin, and the like.
The first alcohol may be at least one selected from the group consisting of glycerin, propylene glycol, butyleneglycol, dipropylene glycol, polyethylene glycol, sorbitol, and combinations thereof.
The second alcohol is selected from the group consisting of lauryl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, linolenyl alcohol, arachidonyl An alcohol, an alcohol, an alcohol, or a combination thereof.
The fatty acid may be at least one selected from the group consisting of stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid, or a combination thereof.
Wherein the oil is selected from the group consisting of cyclodymethicone, dimethicone, diethylhexylcarbonate, hydrogenated polyhedrin, isopropyl myristate, liquid paraffin, vegetable squalane, macadamia nut oil, jojoba oil, avocado oil, olive oil, camellia oil, And combinations thereof.
Another embodiment of the present invention is a method for producing a therapeutic agent comprising a composition comprising the above-mentioned nanotechnology complex for photodynamic therapy, comprising the steps of: heating an emulsifier, a first alcohol, and purified water to prepare an aqueous raw material; Heating the first alcohol, fatty acid, and oil to produce an oily raw material; Mixing the heated water raw material and the oil raw material; Neutralizing and cooling the mixture; And homogenizing the cooled mixture with a nanomechanical complex for photodynamic therapy.
In still another embodiment of the present invention, there is provided a therapeutic agent prepared according to the above-described method for preparing a composition comprising a nano-ion complex for photodynamic therapy, wherein the therapeutic agent is an emulsion, a gel, a liquid, to provide.
Hereinafter, examples and comparative examples of the present invention will be described. However, the following examples are only illustrative of the present invention and are not intended to limit the scope of the present invention.
Example
Example 1: Preparation of an emulsion type therapeutic agent
1. Preparation of nano-ion complex
1-1. Synthesis of Copolymer (Polyethylene Glycol-Polyethyleneimine-Photo Sensitive Agent)
After the reflux condenser was installed, 10 g of methoxypolyethylene glycol (mPEG-COOH) (Sigma, 5000 Da) was dissolved in 50 ml of methylene chloride (CHCl 2 ) using a 250 ml flask. Thereafter, the imide was added to 0.52 g of N-hydroxysuccinimide and 0.74 g of dicycloheta, followed by reaction at room temperature for 20 hours. Dicyclohexylurea was removed through a filter process and then precipitated in diethylether to obtain an activated form of polyethylene glycol (mPEG-NHS).
2 g of the obtained polyethylene glycol was dissolved in 200 ml of chloroform. Thereafter, 0.5g of polyethyleneimine (Alfa Aesar, 1800da) was dissolved in 50ml of chloroform, and then the polyethylene glycol dissolved in the solution was dropped one by one to perform covalent bonding reaction of polyethylene glycol and polyethyleneimine.
The reaction was carried out for 24 hours. After completion of the reaction, the reaction mixture was concentrated to a total volume of 30 ml using a vacuum concentrator, and then precipitated in diethyl ether to obtain a covalent bond of polyethylene glycol and polyethyleneimine .
1 g of the obtained polyethylene glycol-polyethyleneimine (mPEG-PEI) was dissolved in a mixture of pheophorbide A (eq, 0.07 mmol), dicyclohexyl carbodiimide (DCC) (1.2 * pheophorbide A in moles) N-hydroxysuccinimide (HOSu) was dissolved in 20 ml of dimethyl sulfoxide (DMSO) and stirred for 3 hours. Thereafter, the two solutions were mixed and reacted at room temperature for 24 hours. After dialyzing with primary distilled water for 2 days using a dialysis membrane (Spectra / Por; mol. Wt. Cutoff size, 1,000), the final reaction product was freeze-dried to obtain polyethylene glycol-polyethyleneimine- Pheophorbide A copolymer was obtained.
1-2. Synthesis of conjugate (quencher conjugated chondroitin sulfate)
0.1 g of chondroitin sulfate was dissolved in 20 ml of distilled water. After dissolving BHQ3 in dried DMSO, N- (3-dimethylaminopropyl) -N'-ethylcarbodiimine hydrochloride (EDC) and 4-dimethylaminopyridine (DMAP) were added at a ratio of 1.5 times with respect to the molar ratio of BHQ . Then, the two solutions were stirred at room temperature for 3 hours, and then mixed and reacted for 24 hours. The removal of the unreacted quencher (BHQ3) was removed by dialysis using primary distilled water for 2 days using a dialysis membrane (Spectra / Por, mol. Wt. Cutoff size, 1,000) Lt; / RTI > to yield a quencher conjugated chondroitin sulfate conjugate.
1-3. Synthesis of Copolymers and Conjugates
1-1. The polyethylene glycol-polyethyleneimine-pheophorbide A copolymer and the quencher-conjugated chondroitin sulfate conjugate prepared in 1-2. Were dissolved in the tertiary distilled water, respectively, and the mass ratio of the polyethylene glycol-polyethyleneimine-pheophorbide A copolymer was 1.0: 0.3, 1.0: 0.6, 1.0: 1.2, 1.0: 2.5, and 1.0: 5.0. After 2 hours, the mixture was filtered using a 0.8 mu m syringe filter to produce a nano-ion complex.
2. Mixing raw materials
Each of the phases was heated to 80 DEG C to dissolve the emulsifier, the polyhydric alcohol, the higher fatty acid and the oil as an oil phase, using purified water, glycerin, and raw materials as the water phase according to the composition shown in Table 1 below. The water phase or the oil phase was slowly added to the oil phase and uniformly mixed with a mixer and emulsified at 80 ° C for 10 minutes. The emulsion was neutralized with a pH adjuster at 70 DEG C or lower and then cooled to 45 DEG C to obtain a mixture of raw materials.
3. Preparation of Therapeutic Agents Containing Nano-ion Complexes for Photodynamic Therapy
The nano-ion complex prepared by the above-mentioned process was put into a mixture of the raw materials obtained by cooling to 45 ° C as shown in Table 1 below, and homogenized to prepare an emulsion type therapeutic agent.
Example 2: Preparation of a therapeutic agent containing a gel-type photodynamic therapy nano-ion complex
Except that a mixture of raw materials was prepared by heating and dispersing purified water, glycerin, a hydrophilic polymer compound, and ethanol in water phase to 40 ° C according to the composition shown in the following [Table 2] Therapeutic agents containing therapeutic nano-ion complexes were prepared.
Example 3: Preparation of a therapeutic agent comprising a nano-ion complex for liquid photodynamic therapy
Except that a mixture of raw materials was prepared by using purified water, polyhydric alcohol, and ethanol as the water phase in accordance with the composition shown in the following [Table 3], to prepare a therapeutic agent containing a liquid type photodynamic therapy nano- .
Example 4: Preparation of a therapeutic agent containing a nano-ion complex for powdered photodynamic therapy
Except that starch or dextrin or glucose was used as an excipient according to the composition in Table 4 below and homogenized by impregnation with a polyhydric alcohol and a nano-ion complex to prepare a liquid type photodynamic therapy Nano-ion complexes were prepared.
It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.
Claims (8)
Mixing the raw materials,
The step of preparing the nano-
10 g of methoxypolyethylene glycol (mPEG-COOH) (Sigma, 5000 Da) was dissolved in 50 ml of methylene chloride (CHCl 2 ) using a 250 ml flask and 0.52 g of N-hydroxysuccinimide and 0.74 (mPEG-NHS) was obtained by removing dicyclohexylurea through a filter process and precipitating in diethylether for 20 hours at room temperature after addition of the imide from dicyclohexylcarbodiimide , 2 g of the obtained polyethylene glycol was dissolved in 200 ml of chloroform, 0.5 g of polyethyleneimine (Alfa Aesar, 1800 da) was dissolved in 50 ml of chloroform, and a solution of the polyethylene glycol dissolved therein was mixed to obtain a mixture of polyethylene glycol and polyethyleneimine The reaction was carried out for 24 hours. After completion of the reaction, the reaction was carried out using a vacuum concentrator The mixture was concentrated to a total volume of 30 ml and then precipitated in diethyl ether to obtain a covalent bond of polyethylene glycol and polyethyleneimine. 1 g of the obtained polyethylene glycol-polyethyleneimine (mPEG-PEI) (1.2 * pheophorbide A in moles) and N-hydroxysuccinimide (HOSu; 1.2 * pheophorbide A in moles) ) Were dissolved in 20 ml of dimethyl sulfoxide (DMSO), and the solution was stirred for 3 hours. After the two solutions were mixed, the solution was reacted at room temperature for 24 hours, , 1,000), dialyzed for 2 days with primary distilled water, and the final reaction product was dried by lyophilization to obtain a polyethylene glycol-polyethyleneimine-pheophorbide A copolymer Synthetic polymer of step (optical sense the polyethylene glycol-polyethyleneimine);
0.1 g of chondroitin sulfate was dissolved in 20 ml of distilled water and BHQ3 was dissolved in dried DMSO. Then, N- (3-dimethylaminopropyl) -N'-ethylcarbodiimine hydrochloride (EDC), 4-dimethylaminopyridine (BHQ3) was added at a ratio of 1.5 times to the molar ratio of BHQ, and the two solutions were stirred at room temperature for 3 hours, mixed and reacted for 24 hours, and the unreacted BHQ3 was removed using a spectrophotometer (Spectra / Por; and then washed with dialyzed water for 2 days using a distilled water (wt. cutoff size, 1,000), dialyzed and dialyzed to remove the final reaction product by lyophilization to obtain a quencher conjugated chondroitin sulfate conjugate (quencher conjugated chondroitin Sulfate); And
The polyethylene glycol-polyethyleneimine-pheophorbide A copolymer and the quencher-bonded chondroitin sulfate conjugate were dissolved in tertiary distilled water and mixed. After 2 hours, the mixture was filtered using a 0.8 μm syringe filter And a step of synthesizing a copolymer and a conjugate for producing a nano-ion complex,
Wherein the mixing of the raw materials comprises:
Each of the phases was heated to 80 ° C to dissolve the emulsifier, the polyhydric alcohol, the higher fatty acid and the oil as an oil phase, and the water phase was added to the oil phase, and the oil phase was uniformly added to the oil phase with a mixer And emulsified at 80 ° C for 10 minutes to prepare an emulsion. The emulsion was neutralized with a pH adjuster at 70 ° C and cooled to 45 ° C to obtain a mixture,
The mixture may contain,
A nanoparticle complex for photodynamic therapy comprising a copolymer of a hydrophilic cationic polymer and a photosensitizer combined therewith and a combination of an anionic substrate polymer and a photoinitiator,
Wherein the hydrophilic cationic polymer is polyethylene glycol and polyethyleneimine,
The photosensitizer is Chlorin e6, Zinc Phthalocyanine or pheophorbide A,
The anionic substrate polymer is selected from the group consisting of chondroitin-6-sulfate (C6S), heparansulfate (HS), heparan sulfate proteoglycan (HSPG), heparin, chondroitin-4-sulfate (C4S), chondroitin- (DS), keratan sulfate (KS), and hyaluronic acid (HA).
The quencher may be any one of a blackhole quencher (BHQ) or a blackberry quencher (BBQ)
The photodynamic therapy nano ion complex comprises 0.1-10% by weight of an emulsifier, 0.1-10% by weight of a primary alcohol, 0.1-10% by weight of a secondary alcohol, 0.1-10% by weight of a fatty acid, 1-40% Of purified water,
The emulsifier may be a nonionic surfactant having a structure of hydroxyl group (-OH), ether group (-O-), amide group (-CONH) and ester group (-COO-) in the molecule. Polyoxyethylene type, polyhydric alcohol ester type, ethylene oxide and propylene oxide block copolymer, polymeric surfactant of alkyl acrylate copolymer; Lecithin, natural surfactants of lanolin, cholesterol, and saponin,
Wherein the first alcohol is at least one selected from the group consisting of glycerin, propylene glycol, butylene glycol, dipropylene glycol, polyethylene glycol, sorbitol,
The second alcohol is selected from the group consisting of lauryl alcohol, cetyl alcohol, stearyl alcohol, cetearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, linolenyl alcohol, arachidonyl At least one selected from the group consisting of an alcohol, an alcohol, or a combination thereof,
Wherein the fatty acid is at least one selected from the group consisting of stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid,
Wherein the oil is selected from the group consisting of cyclodymethicone, dimethicone, diethylhexylcarbonate, hydrogenated polyhedrin, isopropyl myristate, liquid paraffin, vegetable squalane, macadamia nut oil, jojoba oil, avocado oil, olive oil, camellia oil, At least one member selected from the group consisting of
Wherein the photodynamic therapy nano-ion complex is comprised between 0 and 1 milligram per 100 grams of the composition composition.
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| KR1020140130028A KR101622545B1 (en) | 2014-09-29 | 2014-09-29 | Acne treatment composition and method for manufacturing acne treatment preparation using the same |
| PCT/KR2014/009145 WO2016052775A1 (en) | 2014-09-29 | 2014-09-30 | Composition for treating acne, and method for producing therapeutic agent for acne using same |
| CN201480072497.6A CN105899206A (en) | 2014-09-29 | 2014-09-30 | Composition for treating acne, and method for producing therapeutic agent for acne using same |
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| KR101308507B1 (en) * | 2011-07-07 | 2013-09-17 | (주)비알뷰티플레볼루션 | Acne therapeutics and sebum secernent inhibitor which comprise tryptophan, and kits for photodynamic therapy containing the same |
| KR101336501B1 (en) * | 2011-09-28 | 2013-12-03 | 가톨릭대학교 산학협력단 | Nano ion-complex for photodynamic theraphy comprising hydrophile cationic polymer photosensitizer derivatives and anionic polysaccharide quencher derivatives |
| KR20140014443A (en) * | 2012-07-24 | 2014-02-06 | 국립암센터 | Graphene oxide-photosensitizers complex containing disulfide linker and composition for diagonosis and therapy of canncer using the same |
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| CN105899206A (en) | 2016-08-24 |
| KR20160038132A (en) | 2016-04-07 |
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