JP5379806B2 - 皮膚の保護ケア用テトラペプチド - Google Patents
皮膚の保護ケア用テトラペプチド Download PDFInfo
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- JP5379806B2 JP5379806B2 JP2010531066A JP2010531066A JP5379806B2 JP 5379806 B2 JP5379806 B2 JP 5379806B2 JP 2010531066 A JP2010531066 A JP 2010531066A JP 2010531066 A JP2010531066 A JP 2010531066A JP 5379806 B2 JP5379806 B2 JP 5379806B2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
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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
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- A61Q19/08—Anti-ageing preparations
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- 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
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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Description
PXQXX-(芳香族/酸性)(SEQ ID NO: 16)ペプチドに関するペプチドの設計と合成
1.ペプチドは長さが4アミノ酸だけである(即ち、500ダルトン未満のテトラペプチド)。
2.配列は、TRAF6-結合蛋白質の保存された結合ドメイン[PXQXX-(芳香族/酸性)](SEQ ID NO: 16)から選択される。
3.テトラペプチド配列は、PXQXX-(芳香族/酸性)(SEQ ID NO: 16)の1位置にプロリン、3位置にグルタメートを保存する。
4.2位置及び4位置は、自然発生形態のPXQXX-(芳香族/酸性)(SEQ ID NO: 16)のこれら部位に存在するアミノ酸残基が割り当てられる。
a.2位置:Q, T, L, G, E, V 又は P
b.4位置: I, M, D, V, N, S 又は T
5.追加の変異を作るために、正電荷残基を4位置に用いた。このようなアミノ酸配置は天然アミノ酸では回避されていた。
全てのペプチドは、多重ペプチド合成装置Apex 396(Advanced ChemTech(Louisville, KY))における標準のFmoc化学を用いて合成された。Rinkアミド樹脂は、最初に洗浄し、DMFで予め膨張させた。Fmoc保護基はピペリドン25%を含むDMFで取り除いた。その後、樹脂を洗浄して、微量のピペリドンを除去した。Fmocアミノ酸モノマーは、HOAt又はHOBtの等モル(0.5 M)溶液のDMF中で予め活性化させた。アミド結合は、また束縛塩基(ジイソプロピルエチルアミン)を用いた塩基性条件下にて、HATU、PyBop又はHBTU及び2.5-5倍過剰モルのアミノ酸を用いて行なった。結合効率は、標準のカイザーテストを用いてモニタリングした。
IL-6及びMMP-1の細胞培養及び検出
抗炎症活性に対するペプチドのスクリーニング:ヒト皮膚上皮細胞におけるUV誘発IL-6発現の阻害
抗炎症活性に対するペプチドのスクリーニング:ヒト皮膚の角化細胞及び線維芽細胞におけるUV誘発IL-6発現の阻害
抗炎症活性に対するペプチドのスクリーニング:ヒト皮膚の線維芽細胞におけるUV誘発MMP-1発現の阻害
プロテアーゼ阻害剤を含む本発明の実施例
なお、表2中の省略語は次のとおりである:ACE…アンギオテンシンI変換酵素; ECM…細胞外マトリックス; HA…ヒアルロン酸; HGF…ヘパトサイト増殖因子; MMP…マトリックスメタロプロテイナーゼ; MSH…メラノサイト刺激ホルモン; SNARE…可溶性NSF付着受容体(NSF, N-エチルマレイミド感受性因子); TGF-β…形質転換成長因子-β; TIMP…MMPの組織阻害剤
また、表2中、製造者の所在地は次のとおりである:Atrium Biotechnologies(カナダ、ケベックシティ); Grant Industries(ニュージャージー、エルムウッド); Lipotec(スペイン、バルセロナ); Pentapharm(スイス、バーゼル); Procyte(ペンシルベニヤ、モントゴメリビル、フォトメディックス); Sederma(フランス、Le Perray en Yvelines)
A.TICトレース(全イオンカウント)。これは、特定時間中にカラム/質量分析計を通過する全ての分子重量(全分子)の読み出しである。
B.XICトレース(抽出イオンカウント)。これは、TICトレースからの読み出しで、特定分子重量からのプリング(pulling)を表している。
C.質量スペクトル。これは、TICトレース又はXICトレースから選択されるピーク内における分子的実態の範囲である。
なお、表3の全てのペプチドの最終濃度は1mg/mLである。
(1) Bernard D他(2003), Analysis of proteins with caseinolytic activity in a human stratum corneum extract revealed a yet unidentified cysteine protease and identified the co-called "stratum corneum thiol protease" as cathepsin L2, J. Invest. Dermatol. 120:592-600.
(2) Borgono CA他(2007), A potential role for multiple tissue kallikrein serine proteases in epidermal desquamation, J. Biol. Chem. 282: 3640-3652.
(3) Brattsand M and Egelrud T(1999), Purification, molecular cloning, and expression of a human stratum corneum trypsin-like serine protease with possible function in desquamation, J. Biol. Chem. 274:30033-30040.
(4) Hansson L他(1994), Cloning, expression, and characterization of stratum corneum chymotryptic enzyme. A skin-specific human serine proteinase, J. Biol. Chem. 269:19420-19426.
(5) Horikoshi T他(1998), Isoforms of cathepsin D and human epidermal differentiation, Biochimie 80:605-612.
(6) Johansson J他(1998), Conformation-dependent antibacterial activity of the naturally occurring human peptide LL-37, J. Biol. Chem. 273:3718-3724.
(7) Pampalakis and Sotiropoulou(2007), Tissue kallikrein proteolytic cascade pathways in normal physiology and cancer, Biochim. Biophys. Acta. 1776:22-31.
(8) Voegeli R他(2007), Profiling of serine protease activities in human stratum comeum and detection of a stratum corneum tryptase-like enzyme, Int. J. Cosmet. Sci. 29:191-200.
(9) Yamasaki K他(2007), Increased serine protease activity and cathelicidin promotes skin inflammation in rosacea, Nat. Med. 13:975-980.
Claims (11)
- ペプチドのアミノ酸配列が、プロリン-グルタミン-グルタメート-X(P-Q-E-X)からなり、Xはリジン(K)又はイソロイシン(I)である、単離ペプチド。
- アミノ酸配列は、SEQ ID NO: 14又はSEQ ID NO: 15からなる請求項1のペプチド。
- ペプチドは、SEQ ID NO: 1又はSEQ ID NO: 2である請求項2のペプチド。
- ペプチドは、アミド化されるか、脂質化されるか、担体分子に結合されるか、又はD-鏡像異性体形態のアミノ酸残基を有する請求項1のペプチド。
- 請求項1乃至4の何れかに記載のペプチドと、薬剤として許容される担体とを含んでいる組成物。
- ペプチドは、0.1μg/mL〜50μg/mLの範囲の濃度で存在する請求項5の組成物。
- 組成物は、プロテアーゼ阻害剤をさらに含んでいる請求項5の組成物。
- 組成物は、エアロゾル、エマルジョン、液体、ローション、クリーム、ペースト、軟膏、粉末又はフォームの形態である請求項5の組成物。
- 哺乳動物の皮膚又は該皮膚に関連する粘膜組織の炎症部位に対して、治療に有効な量を有効時間投与することにより、哺乳動物の皮膚又は該皮膚に関連する粘膜組織における炎症を治療するのに有用である、請求項5乃至8の何れかに記載の組成物。
- 炎症は、擦り傷、水膨れ、火傷、裂傷、潰瘍、打撲、発疹若しくはび瘢痕であるか、又は紫外線照射に曝露されることで生じる請求項9の組成物。
- 請求項1乃至4の何れかに記載のペプチドを含む組成物であって、紫外線により損傷した上皮細胞、角化細胞又は線維芽細胞を、前記ペプチドに曝露することにより、前記細胞中におけるインターロイキン(IL)-6又はマトリックスメタロプロテイナーゼ(MMP)-1の発現量を減少させるのに有用である、組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81507P | 2007-10-29 | 2007-10-29 | |
US61/000,815 | 2007-10-29 | ||
PCT/US2008/012191 WO2009058244A1 (en) | 2007-10-29 | 2008-10-28 | Protective skin care tetrapeptides |
Publications (3)
Publication Number | Publication Date |
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JP2011502121A JP2011502121A (ja) | 2011-01-20 |
JP2011502121A5 JP2011502121A5 (ja) | 2011-10-13 |
JP5379806B2 true JP5379806B2 (ja) | 2013-12-25 |
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Application Number | Title | Priority Date | Filing Date |
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JP2010531066A Active JP5379806B2 (ja) | 2007-10-29 | 2008-10-28 | 皮膚の保護ケア用テトラペプチド |
Country Status (10)
Country | Link |
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US (1) | US8071555B2 (ja) |
EP (1) | EP2205623B1 (ja) |
JP (1) | JP5379806B2 (ja) |
KR (1) | KR101668803B1 (ja) |
CN (1) | CN101855235B (ja) |
CA (1) | CA2701420C (ja) |
ES (1) | ES2567706T3 (ja) |
HK (1) | HK1146070A1 (ja) |
PL (1) | PL2205623T3 (ja) |
WO (1) | WO2009058244A1 (ja) |
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WO2014200651A1 (en) | 2013-06-14 | 2014-12-18 | Helix Biomedix Inc. | Tetrapeptides derived from human c-x-c chemokines useful for treatment of various skin conditions |
KR20150130616A (ko) * | 2014-05-13 | 2015-11-24 | (주)케어젠 | 피부상태 개선 활성을 갖는 펩타이드 및 이의 용도 |
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IT201900008364A1 (it) * | 2019-06-07 | 2020-12-07 | Espikem S R L | Peptidi bioattivi e composizioni che li comprendono |
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DE102005063062A1 (de) | 2005-12-29 | 2007-07-05 | Henkel Kgaa | Synergistische Proteinhydrolysat-Kombinationen zur Behandlung reifer Haut |
US7807625B2 (en) * | 2006-01-18 | 2010-10-05 | Grant Industries, Inc | Anti-wrinkle composition |
US9051564B2 (en) * | 2006-02-21 | 2015-06-09 | President And Fellows Of Harvard College | Compositions for and methods of identifying antigens |
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2008
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- 2008-10-28 PL PL08844747.9T patent/PL2205623T3/pl unknown
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KR20100083828A (ko) | 2010-07-22 |
WO2009058244A1 (en) | 2009-05-07 |
US8071555B2 (en) | 2011-12-06 |
CN101855235B (zh) | 2013-04-24 |
KR101668803B1 (ko) | 2016-10-24 |
CA2701420A1 (en) | 2009-05-07 |
JP2011502121A (ja) | 2011-01-20 |
US20090142280A1 (en) | 2009-06-04 |
EP2205623B1 (en) | 2016-03-16 |
ES2567706T3 (es) | 2016-04-26 |
HK1146070A1 (zh) | 2011-05-13 |
CN101855235A (zh) | 2010-10-06 |
CA2701420C (en) | 2016-02-09 |
EP2205623A1 (en) | 2010-07-14 |
PL2205623T3 (pl) | 2016-09-30 |
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