WO2017222108A1 - Composition de liposomes antibactériens contenant un conjugué de phéophorbide a et un dérivé lipidique de polyéthylène glycol - Google Patents

Composition de liposomes antibactériens contenant un conjugué de phéophorbide a et un dérivé lipidique de polyéthylène glycol Download PDF

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WO2017222108A1
WO2017222108A1 PCT/KR2016/008636 KR2016008636W WO2017222108A1 WO 2017222108 A1 WO2017222108 A1 WO 2017222108A1 KR 2016008636 W KR2016008636 W KR 2016008636W WO 2017222108 A1 WO2017222108 A1 WO 2017222108A1
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weight
oil
liposome composition
pheophorbide
liposome
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PCT/KR2016/008636
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English (en)
Korean (ko)
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지홍근
유효경
우영롱
김정동
조세희
나건
박형
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주식회사 에이치엔에이파마켐
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Priority to CN201680087101.4A priority Critical patent/CN109414377B/zh
Publication of WO2017222108A1 publication Critical patent/WO2017222108A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/14—Liposomes; Vesicles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/413—Nanosized, i.e. having sizes below 100 nm

Definitions

  • the present invention relates to an antimicrobial liposome composition containing a combination of a pheophorbide A and a lipid derivative of polyethylene glycol, more particularly 1,2-distearoyl-sn-glycero-3-phosphoethanolamine- 0.0001 to 5% by weight of the combination of N- [amino (polyethylene glycol) -2000] and pheophorbide A, 1 to 10% by weight of polyglyceryl-3-methylglucose distearate, 1 to 10% by weight of polysorbate 80
  • an antibacterial liposome composition comprising 5 to 40% by weight of cetyl palmitate, 1 to 10% by weight of vegetable oil, 2 to 15% by weight of N-methyl-2-pyrrolidone and a balance of water.
  • transdermal delivery systems are mainly applied to make vesicles containing agonists with materials such as surfactants, lipids, and polymers.
  • lipids are used as cosmetic materials because of the advantages of lipids as components of biological membranes.
  • Photodynamic therapy is a technique for treating incurable diseases such as cancer or acne or the like without surgery using a photo-sensitizer.
  • These photodynamic therapies have been actively researched since the early 20th century, and have been used to increase immunity in the diagnosis and treatment of cancer, autologous bone marrow transplantation, antibiotics, AIDS treatment, skin transplantation, and arthritis. The range is gradually expanding.
  • Photodynamic therapy is a singlet oxygen or free radical when a photosensitive substance is administered to the body and the light is irradiated from the outside. (Free radical) is produced, and this single therapy is a treatment method using the principle that oxygen or free radicals induce and destroy various lesion sites or cancer cells.
  • Photosensitive materials used in photodynamic therapy include porphyrin derivatives, chlorin, bacteriochlorin, phthalocyanine, and 5-aminolevulinic acid derivatives. Known.
  • Chlorophylls are the most abundant in plants, and in general there are two types of a and b in higher plants in the ratio of 3: 1 or 3: 2. Chlorophyll has an excellent anti-inflammatory effect and has been used for the treatment of wounds, burns and ulcers. In addition, plant extracts containing chlorophyll are used as cosmetic raw materials for skin damage management.
  • Chlorophylls exist in a variety of derivatives, including pheophytin, pheophorbide, chlorin and phytanic acid.
  • magnesium in the chlorophyll molecule escapes and changes to yellow-green pheophytin, and when the enzyme chlorophyllase acts, the phytol group is released by hydrolysis. It is yellowish brown pheophorbide.
  • chlorophyllase first acts on chlorophyll, it becomes green pheophorbide, and when heat is applied under acidic conditions, it becomes pheophorbide.
  • Korean Patent Application No. 10-2014-0067083 discloses a composition for improving skin condition comprising chlorophyll a or pheophorbide a.
  • previous studies have confirmed that chlorophyll, pheophytin, pyropheophytin and pheophorbide derivatives have potential tumor suppressor effects.
  • Patent Document 1 Korean Patent Application No. 10-2014-0067083
  • the present invention is to provide a composition that can be effectively used in the treatment of acne by effectively delivering a photosensitive material, Peoform bead A into the skin to show an excellent antibacterial action.
  • the present invention provides a combination of 1,2-dstearoyl-sn-glycero-3-phosphoethanolamine-N- [amino (polyethylene glycol) -2000] and pheophorbide A 0.0001 To 5% by weight, polyglyceryl-3 methylglucose distearate 1 to 10% by weight, polysorbate 80 1 to 10% by weight, cetyl palmitate 5 to 40% by weight, vegetable oil 1 to 10% by weight, N- It provides an antimicrobial liposome composition comprising 2 to 15% by weight of methyl-2-pyrrolidone and a balance of water.
  • the present invention also provides a cosmetic composition comprising the antimicrobial liposome composition.
  • Pheophorbide A in the present invention forms a conjugate with a lipid derivative of polyethylene glycol.
  • a lipid derivative of polyethylene glycol 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N- [amino (polyethylene glycol) -2000] (1,2-distearoyl-sn -glycero-3-phosphoethanolamine-N- [amino (polyethylene glycol) -2000]; DSPE-PEG (2000) amine is used.
  • the combination of pheophorbide A with DSPE-PEG (2000) amine may help stabilize the pheophorbide A and efficiently deliver it into the skin.
  • Formation of a combination of pheophorbide A and DSPE-PEG (2000) amine is, for example, in the presence of the catalysts dicyclohexylcarbodiimide (DCC) and N-hydroxysulfosuccinimide (sulfo-NHS). It is obtained by reacting Pheophorbide A with DSPE-PEG (2000) amine, which is shown in Scheme 1 below.
  • DSPE-PEG_PheoA the combination of the pheophorbide A and DSPE-PEG (2000) amine is abbreviated as "DSPE-PEG_PheoA”.
  • the DSPE-PEG_PheoA synthesized in the present invention is used to make a liposome because there is some lack in stability, solubility, skin permeability, etc. to use as a raw material of cosmetics.
  • the liposome composition of the present invention comprises 0.0001 to 5% by weight, preferably 0.001 to 4% by weight, more preferably 0.005 to 3% by weight of DSPE-PEG_PheoA.
  • DSPE-PEG_PheoA when included in less than 0.0001% by weight, the antimicrobial effect of DSPE-PEG_PheoA may be weakened, and when included in excess of 5% by weight, it may be difficult to form liposomes.
  • the liposome composition of the present invention comprises 1 to 10% by weight of polyglyceryl-3 methylglucose distearate, preferably 1.5 to 8% by weight, more preferably 2 to 2, as a nonionic surfactant. 6 weight percent.
  • polyglyceryl-3 methylglucose distearate when polyglyceryl-3 methylglucose distearate is included in an amount of less than 1 wt% or more than 10 wt%, there may be a problem in liposome formation.
  • the liposome composition of the present invention comprises 1 to 10% by weight, preferably 1.5 to 8% by weight, more preferably 2 to 6% by weight of polysorbate 80 (polysorbate 80, polyoxyethylene (20) sorbitan monooleate) as a nonionic surfactant Contains%
  • polysorbate 80 polyoxyethylene (20) sorbitan monooleate
  • Contains% when polysorbate 80 is included in an amount of less than 1 wt% or more than 10 wt%, there may be a problem in liposome formation.
  • the liposome composition of the present invention comprises 5 to 40% by weight, preferably 8 to 35% by weight, more preferably 10 to 30% by weight of cetyl palmitate.
  • Cetyl palmitate in the present invention may increase the affinity of the liposomes with the skin, and may help to penetrate the skin.
  • cetyl palmitate is included in the present invention, less than 5% by weight of the skin affinity and skin penetration of liposomes may be weak, if included in excess of 40% by weight may be a problem in liposome formation.
  • the liposome composition of the present invention comprises 1 to 10% by weight of vegetable oil, preferably 1.5 to 8% by weight, more preferably 2 to 7% by weight.
  • Vegetable oil in the present invention serves to help the skin penetration of liposomes, for example, macadamia oil, sunflower seed oil, olive oil, camellia oil, castor oil, jojoba oil, almond oil, apricot seed oil, green tea oil, meadowfoam seed (meadowfoam seed) oil, argan oil or mixtures thereof may be used, but is not limited thereto.
  • the vegetable oil when the vegetable oil is included in less than 1% by weight may be a problem in the skin penetration of liposomes, when contained in more than 10% by weight may be a problem in liposome formation.
  • the liposome composition of the present invention contains N-methyl-2-pyrrolidone and water as a solvent.
  • the liposome composition of the present invention comprises 2 to 15% by weight, preferably 4 to 13% by weight, more preferably 5 to 10% by weight of N-methyl-2-pyrrolidone.
  • Water in the present invention includes, for example, 10 to 89.9999 weight percent or 38 to 78.995 weight percent.
  • the liposome composition of the present invention may further include additives such as excipients, sweeteners, fragrances as necessary.
  • the particle diameter of the liposomes in the present invention is preferably 100 to 400 nm.
  • a cosmetic composition comprising the liposome composition of the present invention.
  • the cosmetic composition may be, for example, formulated into a skin, lotion, body lotion, cream, essence, hair mist, etc., but is not limited thereto.
  • the cosmetic composition preferably contains 1 to 30% by weight of the liposome composition according to the present invention.
  • the antimicrobial effect may be inadequate, and even if it contains more than 30% by weight, the treatment effect such as acne due to the antimicrobial activity is increased in proportion to the addition thereof. It is hard to expect that anymore and is not economically desirable.
  • the liposome composition of the present invention can effectively treat acne and the like by delivering a photosensitive material, Peoform Bead A, stably and efficiently, into the skin and showing excellent antibacterial activity.
  • Figure 3 is the result of measuring the liposome stability of the present invention.
  • Figure 4 is an enlarged photograph of the liposome composition of the present invention using a frozen electron microscope.
  • FIG. 6 is a graph showing the antimicrobial activity of DSPE-PEG_PheoA of the present invention in comparison with erythromycin.
  • Polyglyceryl-3 methylglucose distearate, cetyl palmitate, macadamia oil and DSPE-PEG_PheoA were dissolved in N-methyl-2-pyrrolidone and heated to 80 ° C.
  • Polysorbate 80 and purified water were heated to 80 ° C. or higher, and then passed through five times at 1,000 bar in a high pressure microemulsifier, followed by cooling and defoaming to obtain a liposome composition.
  • each component was introduced into a container and dissolved at a temperature of 80 ° C., followed by mixing for 5 minutes using a homo mixer, followed by cooling and defoaming to obtain an emulsion.
  • the skin containing the liposome of the present invention was prepared in the following composition of Table 3.
  • the lotion containing the liposome of this invention was prepared with the composition of following Table 4.
  • Particle distribution of the liposomes prepared in Example 1 was measured using Photal ELS-Z and shown in FIG. 1. The measurement showed that the average particle size was 211.23 nm.
  • the liposomes prepared in Example 1 were taken.
  • the particle size of the liposomes was too small to measure by a general optical microscope, and thus, they were photographed using freeze-fracture scanning electron microscopy (FIG. 4). It can be seen from FIG. 4 that the liposomes were well formed in uniform size.
  • mice Female hairless guinea pigs (strain IAF / HA-hrBR) of about 8 weeks were used.
  • the abdominal skin of the guinea pig was cut and then mounted in a Franz-type diffusion cell (Lab fine instruments, Korea).
  • 50 mM phosphate buffer (pH 7.4, 0.1M NaCl) was added to the receptor vessel (5 ml) of the Franz-type diffusion cell, and then the diffusion cell was mixed and dispersed at 32 ° C. and 600 rpm.
  • 50 ⁇ l of the general emulsion of the comparative example was put in a donor container. Absorption and diffusion were carried out according to the scheduled time, and the skin where absorption and diffusion occurred was 0.64 cm 2 .
  • the liposomes of the present invention was found to be superior to the percutaneous absorption compared to the general emulsion.
  • DSPE-PEG_PheoA was dissolved in dimethylsulfoxide (DMSO) to prepare a sample at a concentration of 0.0001%.
  • DMSO dimethylsulfoxide
  • a representative acne-producing bacterium to 2 ⁇ 10 5 CFU / ml, 100 ⁇ l of each sample was added to each test tube, and 4, 8, and 12, respectively, at 37 ° C.
  • the viable cell count of propionibacterium acnes was measured at an absorbance of 625 nm for each sample, and the results are shown in FIG. 6.
  • Staphylococcus sapropicus Staphylococcus hominis, Staphylococcus xyloses, Staphylococcus hemoritisus, Staphylococcus warneri, Staphylococcus auree of DSPE-PEG_PheoA Minimum concentrations indicating antimicrobial activity against Us, Staphylococcus epidermidis and Micrococcus luteus were measured, and the results are shown in Table 10 below.

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  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
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Abstract

La présente invention concerne une composition de liposomes antibactériens contenant un conjugué de phéophorbide A et un dérivé lipidique de polyéthylène glycol et, plus spécifiquement, à une composition de liposome antibactérien contenant de 0,0001 à 5 % en poids d'un conjugué de 1,2-distéaroyl-sn-glycéro-3-phosphoéthanolamine-N-[amino(polyéthylène glycol)-2000] et phéophorbide A, de 1 à 10 % en poids de polyglycéryle-3-méthylglucose distéarate, de 1 à 10 % en poids de polysorbate 80, de 5 à 40 % en poids de palmitate de cétyle, de 1 à 10 % en poids d'une huile végétale, de 2 à 15 % en poids de N-méthyl-2-pyrrolidone, et l'équilibre en eau.
PCT/KR2016/008636 2016-06-24 2016-08-05 Composition de liposomes antibactériens contenant un conjugué de phéophorbide a et un dérivé lipidique de polyéthylène glycol WO2017222108A1 (fr)

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CN201680087101.4A CN109414377B (zh) 2016-06-24 2016-08-05 含有脱镁叶绿酸a及聚乙二醇的脂质衍生物的结合物的抗菌脂质体组合物

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KR1020160079214A KR102630617B1 (ko) 2016-06-24 2016-06-24 페오포르비드 a 및 폴리에틸렌글리콜의 지질 유도체의 결합체를 함유하는 항균 리포좀 조성물
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CN111920773A (zh) * 2020-08-21 2020-11-13 滁州植兀生物科技有限公司 一种纳米载体及其制备方法和应用
KR102578603B1 (ko) * 2022-12-26 2023-09-15 (주)심플스틱 나노복합체, 이의 제조방법 및 용도

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR970007303B1 (ko) * 1992-02-05 1997-05-07 콰드라 로직 테크놀로지스 인코오퍼레이티드 포르피린 광감광제의 리포솜 조성물
KR20050042140A (ko) * 2002-07-31 2005-05-04 파팍 악티엔게젤샤프트 약학 제제 및 내이 질환 치료제로서의 그 용도
US20140234428A1 (en) * 2013-02-15 2014-08-21 Cymbiotics, Inc. Topical dermal delivery compositions using self assembling nanoparticles with cetylated components
WO2015081117A2 (fr) * 2013-11-25 2015-06-04 Echogen, Inc. Complexes de métal thérapeutiques

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR0149564B1 (ko) * 1995-07-25 1998-12-01 최훈 저수호안공사 시의 수중측량점 표시기 설치방법 및 수중측량점 지시기
JP6336703B2 (ja) 2011-10-05 2018-06-06 日産自動車株式会社 耐熱絶縁層付セパレータ
KR101838336B1 (ko) * 2014-09-04 2018-04-26 가톨릭대학교 산학협력단 지질-광감작제 나노결합체 및 이의 제조 방법
KR102251078B1 (ko) * 2014-10-28 2021-05-12 (주) 에이치엔에이파마켐 리조포스파티딜콜린과 클로린 e6의 결합체를 함유하는 여드름 치료용 리포좀 조성물
CN105534724A (zh) * 2016-01-19 2016-05-04 上海应用技术学院 一种包覆白藜芦醇的纳米固体脂质载体及其制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR970007303B1 (ko) * 1992-02-05 1997-05-07 콰드라 로직 테크놀로지스 인코오퍼레이티드 포르피린 광감광제의 리포솜 조성물
KR20050042140A (ko) * 2002-07-31 2005-05-04 파팍 악티엔게젤샤프트 약학 제제 및 내이 질환 치료제로서의 그 용도
US20140234428A1 (en) * 2013-02-15 2014-08-21 Cymbiotics, Inc. Topical dermal delivery compositions using self assembling nanoparticles with cetylated components
WO2015081117A2 (fr) * 2013-11-25 2015-06-04 Echogen, Inc. Complexes de métal thérapeutiques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KRAATZ, MAREIKE ET AL.: "Effects of Chlorophyll-Derived Efflux Pump Inhibitor Pheophorbide a and Pyropheophorbide a on Growth and Macrolide Antibiotic Resistance of Indicator and Anaerobic Swine Manure Bacteria", INTERNATIONAL JOURNAL OF ANTIBIOTICS, vol. 2014, 11 February 2014 (2014-02-11), pages 1 - 14, XP055447386 *

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CN109414377B (zh) 2022-02-08
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KR102630617B1 (ko) 2024-01-29

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