WO2019045248A2 - 주름 개선 활성을 나타내는 펩타이드 및 이의 용도 - Google Patents
주름 개선 활성을 나타내는 펩타이드 및 이의 용도 Download PDFInfo
- Publication number
- WO2019045248A2 WO2019045248A2 PCT/KR2018/007515 KR2018007515W WO2019045248A2 WO 2019045248 A2 WO2019045248 A2 WO 2019045248A2 KR 2018007515 W KR2018007515 W KR 2018007515W WO 2019045248 A2 WO2019045248 A2 WO 2019045248A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- seq
- skin
- amino acid
- acid sequence
- peptide
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 132
- 230000000694 effects Effects 0.000 title claims description 16
- 230000001747 exhibiting effect Effects 0.000 title 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims abstract description 85
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 230000006872 improvement Effects 0.000 claims abstract description 28
- 208000017520 skin disease Diseases 0.000 claims abstract description 24
- 239000002537 cosmetic Substances 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- 235000013305 food Nutrition 0.000 claims abstract description 13
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims description 22
- 230000036560 skin regeneration Effects 0.000 claims description 12
- 230000037303 wrinkles Effects 0.000 claims description 10
- 230000009759 skin aging Effects 0.000 claims description 7
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 6
- 206010000496 acne Diseases 0.000 claims description 6
- 201000008937 atopic dermatitis Diseases 0.000 claims description 6
- 230000008929 regeneration Effects 0.000 claims description 6
- 238000011069 regeneration method Methods 0.000 claims description 6
- 230000037394 skin elasticity Effects 0.000 claims description 6
- 230000002087 whitening effect Effects 0.000 claims description 6
- 230000001629 suppression Effects 0.000 claims description 4
- 206010012434 Dermatitis allergic Diseases 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 206010013786 Dry skin Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 230000037336 dry skin Effects 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 14
- 230000002265 prevention Effects 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 210000003491 skin Anatomy 0.000 description 27
- 210000002950 fibroblast Anatomy 0.000 description 23
- 210000004027 cell Anatomy 0.000 description 22
- 230000035755 proliferation Effects 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 210000002510 keratinocyte Anatomy 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 102000008186 Collagen Human genes 0.000 description 16
- 108010035532 Collagen Proteins 0.000 description 16
- 229920001436 collagen Polymers 0.000 description 16
- 102000016942 Elastin Human genes 0.000 description 14
- 108010014258 Elastin Proteins 0.000 description 14
- 102000016359 Fibronectins Human genes 0.000 description 14
- 108010067306 Fibronectins Proteins 0.000 description 14
- 229920002549 elastin Polymers 0.000 description 13
- 102000004196 processed proteins & peptides Human genes 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000003757 reverse transcription PCR Methods 0.000 description 10
- 102000004363 Aquaporin 3 Human genes 0.000 description 9
- 108090000991 Aquaporin 3 Proteins 0.000 description 9
- 102000043136 MAP kinase family Human genes 0.000 description 9
- 108091054455 MAP kinase family Proteins 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000026731 phosphorylation Effects 0.000 description 9
- 238000006366 phosphorylation reaction Methods 0.000 description 9
- 239000013641 positive control Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 8
- 102000004218 Insulin-Like Growth Factor I Human genes 0.000 description 8
- -1 MTT assay Proteins 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 239000000796 flavoring agent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 238000002965 ELISA Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 102100024785 Fibroblast growth factor 2 Human genes 0.000 description 7
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 7
- 230000032683 aging Effects 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 230000001737 promoting effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 5
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 108010041191 Sirtuin 1 Proteins 0.000 description 4
- 102000000344 Sirtuin 1 Human genes 0.000 description 4
- 210000004899 c-terminal region Anatomy 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 108020004999 messenger RNA Proteins 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000011191 terminal modification Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- NDKDFTQNXLHCGO-UHFFFAOYSA-N 2-(9h-fluoren-9-ylmethoxycarbonylamino)acetic acid Chemical compound C1=CC=C2C(COC(=O)NCC(=O)O)C3=CC=CC=C3C2=C1 NDKDFTQNXLHCGO-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 238000008157 ELISA kit Methods 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 102100031181 Glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000011543 agarose gel Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000010805 cDNA synthesis kit Methods 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- 235000012241 calcium silicate Nutrition 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 239000013592 cell lysate Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 210000004207 dermis Anatomy 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000015203 fruit juice Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000003102 growth factor Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 230000011664 signaling Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 230000008591 skin barrier function Effects 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 238000001262 western blot Methods 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- MGHMWKZOLAAOTD-DEOSSOPVSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-(1h-indol-3-yl)propanoic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)N[C@H](C(=O)O)CC1=CNC2=CC=CC=C12 MGHMWKZOLAAOTD-DEOSSOPVSA-N 0.000 description 1
- JAUKCFULLJFBFN-VWLOTQADSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoic acid Chemical compound C1=CC(OC(C)(C)C)=CC=C1C[C@@H](C(O)=O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 JAUKCFULLJFBFN-VWLOTQADSA-N 0.000 description 1
- UMRUUWFGLGNQLI-QFIPXVFZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 UMRUUWFGLGNQLI-QFIPXVFZSA-N 0.000 description 1
- HNICLNKVURBTKV-NDEPHWFRSA-N (2s)-5-[[amino-[(2,2,4,6,7-pentamethyl-3h-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-(9h-fluoren-9-ylmethoxycarbonylamino)pentanoic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)N[C@H](C(O)=O)CCCN=C(N)NS(=O)(=O)C1=C(C)C(C)=C2OC(C)(C)CC2=C1C HNICLNKVURBTKV-NDEPHWFRSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 238000000116 DAPI staining Methods 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 239000001512 FEMA 4601 Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004378 Glycyrrhizin Substances 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 238000000134 MTT assay Methods 0.000 description 1
- 231100000002 MTT assay Toxicity 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- HELXLJCILKEWJH-SEAGSNCFSA-N Rebaudioside A Natural products O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@]1(C)[C@@H]2[C@](C)([C@H]3[C@@]4(CC(=C)[C@@](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@H](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 HELXLJCILKEWJH-SEAGSNCFSA-N 0.000 description 1
- 244000228451 Stevia rebaudiana Species 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 229960001714 calcium phosphate Drugs 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229960003340 calcium silicate Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229940014259 gelatin Drugs 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 1
- 229960004949 glycyrrhizic acid Drugs 0.000 description 1
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 description 1
- 235000019410 glycyrrhizin Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 230000006303 immediate early viral mRNA transcription Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 125000001151 peptidyl group Chemical group 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 235000019203 rebaudioside A Nutrition 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000012679 serum free medium Substances 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000037373 wrinkle formation Effects 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/17—Amino acids, peptides or proteins
- A23L33/18—Peptides; Protein hydrolysates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
-
- 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
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- 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
-
- 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
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/318—Foods, ingredients or supplements having a functional effect on health having an effect on skin health and hair or coat
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Definitions
- the present invention relates to a peptide comprising the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4, a pharmaceutical composition for preventing or treating skin diseases containing the peptide, a cosmetic composition for improving skin condition comprising the peptide, A method for preventing or treating skin diseases using the peptide, and a method for preventing, treating or improving a skin disease of the peptide.
- the human skin constantly undergoes changes, the most typical of which is degradation of the skin caused by aging and a reduction in the visual beauty.
- Skin aging is largely divided into endogenous aging by genetic factors and exogenous aging by external environmental factors such as sunlight.
- Aging forms wrinkles of the skin, and examples of typical wrinkle formation include reduction of active oxygen, ultraviolet rays, and biosynthesis of collagen.
- active oxygen ultraviolet rays
- biosynthesis of collagen In the case of endogenous aging of skin, it is impossible to control artificially, but in the case of extrinsic aging, aging can be prevented, treated or delayed by removing active oxygen, promoting fibroblast proliferation and promoting biosynthesis of collagen.
- peptides containing the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4 can be usefully used for improving skin wrinkles, .
- an object of the present invention is to provide a peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4.
- Another object of the present invention is to provide a pharmaceutical composition for preventing or treating skin diseases comprising at least one peptide selected from the group consisting of peptides consisting of the amino acid sequence of SEQ ID NO: 1 or 2.
- Another object of the present invention is to provide a cosmetic composition for improving skin condition comprising at least one peptide selected from the group consisting of peptides consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4.
- Yet another object of the present invention is to provide a food composition for improving skin condition comprising at least one peptide selected from the group consisting of peptides consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4.
- Another object of the present invention is to provide a method for preventing or treating skin diseases using a peptide consisting of the amino acid sequence of SEQ ID NO: 1 or 2.
- Another object of the present invention relates to a skin condition improving use of a peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4.
- Another object of the present invention relates to the use of a peptide consisting of the amino acid sequence of SEQ ID NO: 1 or 2 for the prevention or treatment of skin diseases.
- the present invention relates to a peptide comprising the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4, a pharmaceutical composition for preventing or treating skin diseases containing the peptide, a cosmetic composition for improving skin condition comprising the peptide, A method for preventing or treating skin diseases using the peptide, and a method for preventing, treating or improving a skin disease of the peptide.
- a representative feature of the skin wrinkles is collagen, elastin, and fibronectin level inhibition, extracellular matrix proteins (ECM) that constitute the dermis.
- ECM extracellular matrix proteins
- One aspect of the invention relates to a peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4.
- the peptide may be one in which an N-terminal and / or C-terminal modification is induced to select a portion of the amino acid sequence and increase its activity.
- N-terminal and / or C-terminal modifications can significantly improve the stability of the peptide of the present invention, for example, increase the half-life in vivo administration of the peptide.
- the N-terminal modification may be carried out at the N-terminus of the peptide using an acetyl group, a fluorenylmethoxycarbonyl group, a formyl group, a palmitoyl group, a myristyl group, ), A stearyl group, and a polyethylene glycol (PEG).
- the C-terminal modification may be a combination of a hydroxyl group (-OH), an amino group (-NH 2), an azide (-NHNH 2), or the like at the C-terminal of the peptide, but not limited thereto .
- the protecting group acts to protect the peptide of the present invention against attack of a protein cleaving enzyme in vivo.
- Another embodiment of the present invention relates to a pharmaceutical composition for preventing or treating skin diseases comprising at least one peptide selected from the group consisting of peptides consisting of the amino acid sequence of SEQ ID NO: 1 or 2.
- the skin disease may be psoriasis, atopic dermatitis, non-allergic dermatitis, and dry skin, but is not limited thereto.
- the pharmaceutical composition may comprise a pharmaceutically effective amount of at least one peptide selected from the group consisting of peptides consisting of the amino acid sequence of SEQ ID NO: 1 or 2.
- the pharmaceutical composition may further comprise a pharmaceutically acceptable carrier.
- the pharmaceutically acceptable carriers are those conventionally used in the formulation and include lactose, dextrose, sucrose, sorbitol, mannitol, starch, acacia rubber, calcium phosphate, alginate, gelatin, calcium silicate, microcrystalline cellulose, But are not limited to, polyvinylpyrrolidone, cellulose, water, syrup, methylcellulose, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil. Suitable pharmaceutically acceptable carriers and formulations are described in detail in Remington ' s Pharmaceutical Sciences (19th ed., 1995).
- the pharmaceutical composition of the present invention may further include, but is not limited to, lubricants, wetting agents, sweetening agents, flavoring agents, emulsifying agents, suspending agents, preservatives, etc. in addition to the above components.
- the pharmaceutical composition may be administered orally or parenterally, preferably parenterally.
- parenteral administration the pharmaceutical composition may be administered by intramuscular injection, intravenous injection, subcutaneous injection, intraperitoneal injection, topical administration, transdermal administration or the like , But is not limited thereto.
- the dosage of the pharmaceutical composition may be from 0.0001 to 1000 ug per day (microgram, 0.001 to 1000 ug, 0.01 to 1000 ug, 0.1 to 1000 ug, or 1.0 to 1000 ug, but not limited to, , The mode of administration, the age, weight, sex, pathological condition, food, administration time, route of administration, excretion rate, and responsiveness of the patient.
- the pharmaceutical composition may be prepared in the form of a unit dose by formulating it with a pharmaceutically acceptable carrier and / or excipient according to a method which can be easily carried out by those having ordinary skill in the art to which the present invention belongs. Into a multi-dose container.
- the formulations may be in the form of solutions, suspensions or emulsions in oils or aqueous media, or in the form of excipients, powders, granules, tablets or capsules, and may additionally contain dispersing agents and / or stabilizers.
- Another aspect of the present invention relates to a food composition for improving skin condition comprising at least one peptide selected from the group consisting of peptides consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4 as an active ingredient.
- the skin condition improvement may be wrinkle improvement, skin regeneration, skin elasticity improvement, skin aging suppression, wound regeneration, acne improvement, skin regeneration or skin whitening, but is not limited thereto.
- the food may be various foods, beverages, food additives, and the like.
- the content of the peptide as an active ingredient contained in the food composition is not particularly limited depending on the form of the food and the intended use, and may be, for example, 0.01 to 15% by weight of the total food, Can be added at a ratio of 0.02 to 10 g, preferably 0.3 to 1 g, based on 100 ml.
- the liquid ingredient other than the peptide when the food is a beverage, there is no particular restriction on the liquid ingredient other than the peptide as an essential ingredient at the indicated ratio, and it may contain various flavors or natural carbohydrates as an additional ingredient such as ordinary beverages.
- the natural carbohydrate may be selected from the group consisting of monosaccharides such as disaccharides such as glucose and fructose such as maltose and sucrose and polysaccharides such as dextrin and cyclodextrin, , Sorbitol, and erythritol.
- monosaccharides such as disaccharides such as glucose and fructose such as maltose and sucrose
- polysaccharides such as dextrin and cyclodextrin, , Sorbitol, and erythritol.
- Natural flavors can be advantageously used as flavors other than those described above
- the ratio of the natural carbohydrate is generally about 1 to 20 g, preferably about 5 to 12 g per 100 ml of the composition of the present invention.
- the food composition of the present invention can be used as a flavoring agent such as a variety of nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors, coloring agents and thickening agents (cheese, chocolate etc.), pectic acid and its salts, A salt thereof, an organic acid, a protective colloid thickener, a pH adjusting agent, a stabilizer, a preservative, a glycerin, an alcohol, a carbonating agent used in a carbonated drink, and the like.
- a flavoring agent such as a variety of nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors, coloring agents and thickening agents (cheese, chocolate etc.), pectic acid and its salts, A salt thereof, an organic acid, a protective colloid thickener, a pH adjusting agent, a stabilizer, a preservative, a glycerin, an alcohol, a carbonating agent used in a carbonated drink, and the like.
- the food composition of the present invention may contain natural fruit juice and pulp for the production of fruit juice drinks and vegetable drinks. These components may be used independently or in combination. The proportion of such additives is not so critical, but is generally selected in the range of 0 to about 20 parts by weight per 100 parts by weight of the composition of the present invention.
- Another aspect of the present invention relates to a cosmetic composition for improving skin condition comprising at least one selected from the group consisting of peptides consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4.
- the skin condition improvement may be wrinkle improvement, skin regeneration, skin elasticity improvement, skin aging suppression, wound regeneration, acne improvement, skin regeneration or skin whitening, but is not limited thereto.
- the cosmetic composition comprises: (a) a cosmetically effective amount of the peptides of the invention described above; And / or (b) a cosmetically acceptable carrier.
- a cosmetically effective amount means an amount sufficient to achieve the skin condition improving effect of the composition of the present invention described above.
- the cosmetic composition may be in any form conventionally prepared in the art and may be in the form of, for example, a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant- , A powder foundation, an emulsion foundation, a wax foundation, and a spray, but is not limited thereto. More specifically, it can be manufactured in the form of a soft lotion, a nutritional lotion, a nutritional cream, a massage cream, an essence, an eye cream, a cleansing cream, a cleansing foam, a cleansing water, a pack, a spray or a powder.
- the formulation of the cosmetic of the present invention is a paste, a cream or a gel, an animal oil, a vegetable oil, a wax, a paraffin, a starch, a tracer, a cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, Can be used.
- lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component, and in the case of a spray, additionally a chlorofluorohydrocarbon , Propane / butane or dimethyl ether.
- a solvent, a dissolving agent or an emulsifying agent is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, , 1,3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or fatty acid esters of sorbitan.
- the formulation of the cosmetic composition of the present invention is a suspension
- a carrier such as water, a liquid diluent such as ethanol or propylene glycol, a suspension such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, Microcrystalline cellulose, aluminum metahydroxide, bentonite, agar or tracant, etc. may be used.
- the carrier component may include aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, Fatty acid amide ether sulfate, alkylamidobetaine, aliphatic alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, lanolin derivative, or ethoxylated glycerol fatty acid ester.
- ingredients contained in the cosmetic composition of the present invention include, in addition to the peptide and carrier component as the active ingredient, components commonly used in cosmetic compositions, such as antioxidants, stabilizers, solubilizers, vitamins, And may contain the same conventional adjuvants.
- improvement of skin condition encompasses a process of treating, alleviating, or alleviating damage to the skin caused by intrinsic or extrinsic factors of the skin or its effect. For example, But it is not limited thereto.
- Another aspect of the present invention relates to a skin condition improving use of a peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4.
- the skin condition improvement may be wrinkle improvement, skin regeneration, skin elasticity improvement, skin aging suppression, wound regeneration, acne improvement, skin regeneration or skin whitening, but is not limited thereto.
- Another aspect of the present invention relates to the use of a peptide consisting of the amino acid sequence of SEQ ID NO: 1 or 2 for the prevention or treatment of skin diseases.
- the skin disease may be psoriasis, atopic dermatitis, non-allergic dermatitis, and dry skin, but is not limited thereto.
- the peptide consisting of the amino acid sequence of SEQ ID NO: 1 or 2 is the same as described above.
- peptide refers to a linear molecule formed by peptide bonds and amino acid residues joined together.
- the peptides of the present invention can be synthesized by chemical synthesis methods known in the art, especially solid-phase synthesis techniques (Merrifield, J. Amer. Chem. Soc. 85: 2149-54 (1963); Stewart, Solid Phase Peptide Synthesis, 2nd ed., Pierce Chem. Co .: Rockford, 111 (1984)) or liquid phase synthesis technology (US Patent No. 5,516,891).
- stability means not only stability in vivo but also storage stability (e.g., room temperature storage stability).
- the term " pharmaceutically effective amount” means an amount sufficient to achieve efficacy or activity of the peptides described above.
- the present invention relates to a peptide comprising the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4, a pharmaceutical composition for preventing or treating skin diseases containing the peptide, a cosmetic composition for improving skin condition comprising the peptide, A method for preventing or treating skin diseases using the peptide, and a method for preventing, treating or improving a skin disease of the peptide.
- Fig. 1 is a graph showing the results of evaluating the proliferation of fibroblasts of a peptide consisting of the amino acid sequence of SEQ ID NO: 1 according to an embodiment of the present invention.
- FIG. 2 is a graph showing the results of evaluating the proliferation of fibroblasts of the peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to the embodiment of the present invention.
- FIG. 3 is a graph showing the results of evaluating the proliferation of fibroblasts of a peptide consisting of the amino acid sequence of SEQ ID NO. 3 according to an embodiment of the present invention.
- FIG. 4 is a graph showing the results of evaluating the proliferation of fibroblasts of a peptide consisting of the amino acid sequence of SEQ ID NO: 4 according to an embodiment of the present invention.
- FIG. 5 is a graph showing the results of evaluating promotion of proliferation of keratinocytes of a peptide consisting of the amino acid sequence of SEQ ID NO: 1 according to an embodiment of the present invention.
- FIG. 6 is a graph showing the results of evaluating promotion of proliferation of keratinocytes of a peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to an embodiment of the present invention.
- FIG. 7 is a graph showing a result of evaluating promotion of proliferation of keratinocytes of a peptide consisting of the amino acid sequence of SEQ ID NO. 3 according to an embodiment of the present invention.
- FIG. 8 is a graph showing the results of evaluating promotion of proliferation of keratinocytes of a peptide consisting of the amino acid sequence of SEQ ID NO: 4 according to an embodiment of the present invention.
- FIG. 9 is a photograph showing the result of measuring the phosphorylation level of MAPK (AKT elimination) in fibroblasts of a peptide consisting of the amino acid sequence of SEQ ID NO: 1 according to an embodiment of the present invention.
- FIG. 10 is a photograph showing the result of measuring the phosphorylation level of MAPK (AKT elimination) in fibroblasts of a peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to an embodiment of the present invention.
- FIG. 11 is a photograph showing the results of measurement of the phosphorylation level of MAPK and AKT in fibroblasts of the peptide consisting of the amino acid sequence of SEQ ID NO: 3 according to the embodiment of the present invention.
- FIG. 12 is a photograph showing the results of measuring the phosphorylation level of MAPK and AKT in fibroblasts of a peptide consisting of the amino acid sequence of SEQ ID NO: 4 according to an embodiment of the present invention.
- FIG. 13 is a photograph showing the results of measuring the phosphorylation level of MAPK (AKT elimination) in keratinocytes of the peptide consisting of the amino acid sequence of SEQ ID NO: 1 according to the embodiment of the present invention.
- FIG. 14 is a photograph showing the result of measuring the phosphorylation level of MAPK (AKT elimination) in keratinocytes of the peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to the embodiment of the present invention.
- FIG. 15 is a photograph showing the results of collagen 1a, fibronectin and elastin RT-PCR of the peptide consisting of the amino acid sequence of SEQ ID NO: 1 according to the embodiment of the present invention.
- 16 is a photograph showing the results of collagen 1a, fibronectin and elastin RT-PCR of the peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to the embodiment of the present invention.
- 17 is a photograph showing the results of collagen 1a, fibronectin and elastin RT-PCR of the peptide consisting of the amino acid sequence of SEQ ID NO: 3 according to the embodiment of the present invention.
- FIG. 18 is a photograph showing the results of collagen 1a, fibronectin and elastin RT-PCR of the peptide consisting of the amino acid sequence of SEQ ID NO: 4 according to the embodiment of the present invention.
- FIG. 19 is a photograph showing the result of AQP3 (Aquaporin 3) RT-PCR of the peptide consisting of the amino acid sequence of SEQ ID NO: 1 according to the embodiment of the present invention.
- 20 is a photograph showing the SIRT1 RT-PCR result of the peptide consisting of the amino acid sequence of SEQ ID NO: 1 according to the embodiment of the present invention.
- 21 is a photograph showing the result of AQP3 (Aquaporin 3) RT-PCR of the peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to the embodiment of the present invention.
- FIG. 22 is a photograph showing the result of measuring the amount of collagen 1a expression of the peptide consisting of the amino acid sequence of SEQ ID NO. 1 according to the embodiment of the present invention.
- FIG. 22 is a photograph showing the result of measuring the amount of collagen 1a expression of the peptide consisting of the amino acid sequence of SEQ ID NO. 1 according to the embodiment of the present invention.
- FIG. 23 is a photograph showing the result of measurement of the amount of fibronectin expressed in the peptide consisting of the amino acid sequence of SEQ ID NO: 1 according to the embodiment of the present invention.
- FIG. 24 is a photograph showing the measurement result of the amount of elastin expressed in the peptide consisting of the amino acid sequence of SEQ ID NO: 1 according to the embodiment of the present invention.
- FIG. 25 is a photograph showing the result of measuring the amount of collagen 1a expression of the peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to the embodiment of the present invention.
- FIG. 26 is a photograph showing the result of measurement of the amount of fibronectin expressed in the peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to the embodiment of the present invention.
- FIG. 27 is a photograph showing the measurement result of elastin expression amount of a peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to the embodiment of the present invention.
- 29 is a photograph showing the result of Procollagen1a ELISA of the peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to the embodiment of the present invention.
- FIG. 30 is a photograph showing the result of Procollagen1a ELISA of the peptide consisting of the amino acid sequence of SEQ ID NO: 3 according to the embodiment of the present invention.
- FIG. 31 is a photograph showing the result of Procollagen1a ELISA of the peptide consisting of the amino acid sequence of SEQ ID NO: 4 according to the embodiment of the present invention.
- FIG. 32 is a photograph showing an HA ELISA result of a peptide consisting of the amino acid sequence of SEQ ID NO: 2 according to an embodiment of the present invention.
- the present invention relates to a peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4.
- chlorotrityl chloride resin (CTC resin, Nova biochem Cat No. 01-64-0021) was placed in a reaction vessel, and 490 ml of methylene chloride (MC) was added and stirred for 3 minutes. Then, the solution was removed, 490 ml of dimethylformamide (DMF) was added, stirred for 3 minutes, and then the solvent was removed. 200 ml of Fmoc-Tyr (tBu) -OH (Bachem, Swiss) and 400 mmole of diisopropylethylamine (DIEA) were added to the reactor, 700 ml of dichloromethane solution was added, stirred well and dissolved for 1 hour The reaction was carried out with stirring.
- CTC resin chlorotrityl chloride resin
- MC methylene chloride
- DMF dimethylformamide
- DIEA diisopropylethylamine
- Peptidyl resin was washed three times each with DMF, MC and methanol, dried slowly by flowing nitrogen air, and then completely dried by vacuum reduction under P 2 O 5 , followed by filtration (Trifluroacetic acid 81.5 , 1,900 ml of distilled water 5.0%, Thioanisole 5.0%, Phenol 5.0%, EDT, Ethanedithiol 2.5%, TIS (Triisopropylsilane 1.0%) and the mixture was shaken at room temperature The reaction was maintained for 2 hours. The resin was filtered and the resin was washed with a small amount of TFA solution and then combined with the mother liquor.
- the combined mother liquor (2,090 ml) was added with cold ether to induce precipitation, and the precipitate was collected by centrifugation and washed twice with cold ether.
- the mother liquor was removed and sufficiently dried under nitrogen to synthesize 79.8 g of the peptide consisting of SEQ ID NO: 1 before purification (yield: 97.0%).
- the molecular weight was 822.9 (theoretical value: 822.9) when the molecular weight was measured using a molecular weight analyzer.
- the peptide consisting of the amino acid sequence of SEQ ID NO: 2, SEQ ID NO: 3 or SEQ ID NO: 4 was synthesized as described above.
- SEQ ID NO Sequence List Analytical value (mass spectrometer) Analytical value Theoretical value One KWGGGRY 822.9 822.9 2 ILGRWCG 803.9 803.9 3 GPVH 408.4 408.4 4 EDEFKPPAAGR 1216.3 1216.3
- Mouse fibroblast NIH3T3 was seeded in a 96-well plate at a density of 5 x 10 3 cells / well and then cultured overnight. Subsequently, the cells were changed to 0.05% serum-containing media. Then, the positive control 100 nM bFGF and the peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4 were treated with 10 uM or 50 uM for 3 days, / ml MTT solution and reacted for 4 hours. Then, the resulting formazan glass was dissolved by treatment with dimethyl sulfoxide (hereinafter referred to as DMSO), and the absorbance at 560 nm was measured using a microplate reader. The results are shown in Figs. 1 to 4 And Table 2.
- DMSO dimethyl sulfoxide
- Fibroblast proliferation (%) 1 Control SEQ ID NO: 1 bFGF (100 nM) 10uM 50 uM 100 170 194 279 2 Control SEQ ID NO: 2 bFGF (100 nM) 10uM 50 uM 100 188 253 400 3 Control SEQ ID NO: 3 bFGF (100 nM) 10uM 50 uM 100 194 261 386 4 Control SEQ ID NO: 4 bFGF (100 nM) 10uM 50 uM 100 114 193 386
- the peptide having the amino acid sequence of SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3 or SEQ ID NO: 4 promoted fibroblast proliferation.
- HaCaT a human keratinocyte
- DMSO dimethyl sulfoxide
- NIH3T3 mouse fibroblasts at a density of 5x10 3 cells / well and then seeded in 6-well plates and incubated overnight. Subsequently, the cells were treated with 10 uM or 50 uM of the peptide consisting of the positive control 100 nM bFGF and the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4 for 30 minutes, And cell lysate was prepared. Then, western blotting was performed using P-MAPK (p-Erk, p-JNK, p-p38), p-Akt or Actin antibody (santacruz biotechnology, USA) The results are shown in Figures 9-12.
- the peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4 can be produced by the activation of MAPK (ERK, p38, JNK), a signaling factor involved in the proliferation of fibroblasts, In the case of the present invention.
- MAPK ERK, p38, JNK
- a signaling factor involved in the proliferation of fibroblasts In the case of the present invention.
- HaCaT a human keratinocyte
- a human keratinocyte was seeded in a 6-well plate at a density of 3 x 10 cells / well and then cultured overnight. Subsequently, the cells were treated with 10 uM or 50 uM of the peptide consisting of the positive control 10 nM EGF and the amino acid sequence of SEQ ID NO: 1 or 2 for 30 minutes, and the cells were recovered to obtain cells Cell lysate was prepared. Then, western blotting was performed using P-MAPK (p-Erk, p-JNK, p-p38) and p-Akt antibody (santacruz biotechnology, USA) 13 and 14, respectively.
- P-MAPK p-Erk, p-JNK, p-p38
- p-Akt antibody asantacruz biotechnology, USA
- peptide consisting of the amino acid sequence of SEQ ID NO: 1 or 2 showed an effect of promoting proliferation through activation of ERK and p38, which are signal transduction factors involved in human keratinocyte proliferation.
- Example 4 Collagen 1a, fibronectin and elastin RT-PCR
- NIH3T3 mouse fibroblasts at a density of 5x10 3 cells / well and then seeded in 6-well plates and incubated overnight. Then, the medium containing the 0.05% FBS was replaced with the culture medium for 4 hours, and the positive control 100 nM IGF-1 and the peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4 were treated with 10 uM or 50 uM for 24 hours And the cells were recovered and RNA was isolated.
- the peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4 shows the effect of increasing the expression of collagen, fibronectin, and elastin mRNA as constituents of ECM through promoting fibroblast activity Respectively.
- HaCaT a human keratinocyte
- a human keratinocyte was seeded in a 6-well plate at a density of 3 x 10 cells / well and then cultured overnight. Then, the medium was replaced with 0.05% FBS-containing medium and incubated for 4 hours. Then, positive control 100 nM EGF and 10 uM of peptide consisting of the amino acid sequence of SEQ ID NO: 1 or 2 were treated with 50 uM for 24 hours and cells were recovered RNA was isolated.
- CDNA was synthesized using cDNA synthesis kit (Intron, Korea) after quantification of RNA, and PCR was carried out using primers of AQP3, SIRT1 and GAPDH of PCR premix (Intron, Korea) and Table 5 below. Then, the cells were run on 5% agarose gel to compare the mRNA expression levels of the growth factors under the respective peptide treatment conditions, and the results are shown in FIGS. 19 to 21.
- the peptide consisting of the amino acid sequence of SEQ ID NO: 1 or 2 increased the expression of AQP3, a protein involved in skin barrier enhancement, through promotion of keratinocyte activation.
- NIH3T3 mouse fibroblasts at a density of 5x10 3 cells / well and then seeded in 6-well plates and incubated overnight. Subsequently, the cells were changed to serum-free medium, treated with a positive control 100 nM bFGF, and a peptide consisting of the amino acid sequence of SEQ ID NO: 1 or 2 for 24 hours, and cultured in 4% paraformaldehyde ) For 30 minutes. Then, after washing 3 times, the cells were reacted with 0.5% Triton X-100 for 15 minutes and washed again 3 times.
- the peptide consisting of the amino acid sequence of SEQ ID NO: 1 or 2 exhibited the effect of increasing the expression of collagen, fibronectin, and elastin protein as components of the ECM through promoting fibroblast activity.
- NIH3T3 mouse fibroblasts at a density of 5x10 3 cells / well and then seeded in 6-well plates and incubated overnight. Subsequently, the cells were changed to 0.05% FBS-containing media and cultured for 4 hours. Then, the positive control 100 nM IGF-1 and the peptide consisting of the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4 were treated and cultured for 72 hours Recall. The content in the medium was measured using Procollagen1a ELISA kit (Usbiological lifescience, USA), and the results are shown in Figs. 28 to 31 and Table 6. Fig.
- HaCaT a human keratinocyte
- a human keratinocyte was seeded in a 6-well plate at a density of 3 x 10 cells / well and then cultured overnight. After replacing with 0.05% FBS-containing media and incubating for 4 hours, the peptide consisting of the positive control 100 nM IGF-1 and the amino acid sequence of SEQ ID NO: 2 was cultured for 72 hours and the medium was recovered. The content in the medium was measured using an HA ELISA kit (Echelon, USA), and the results are shown in FIG. 32 and Table 7.
- HA expression (ng / ml) 32 Control SEQ ID NO: 2 IGF-1 (100 nM) 10uM 50 uM 251 286 292 280
- the peptide consisting of the amino acid sequence of SEQ ID NO: 2 increased the expression of HA, a protein involved in skin barrier enhancement, through promotion of keratinocyte activation.
- the present invention relates to a peptide comprising the amino acid sequence of SEQ ID NO: 1, 2, 3 or 4, a pharmaceutical composition for preventing or treating skin diseases containing the peptide, a cosmetic composition for improving skin condition comprising the peptide, A method for preventing or treating skin diseases using the peptide, and a method for preventing, treating or improving a skin disease of the peptide.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Birds (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Mycology (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
- Cosmetics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
Description
서열 번호 | 서열 목록 | 분석값(질량분석기) | |
분석치 | 이론치 | ||
1 | KWGGGRY | 822.9 | 822.9 |
2 | ILGRWCG | 803.9 | 803.9 |
3 | GPVH | 408.4 | 408.4 |
4 | EDEFKPPAAGR | 1216.3 | 1216.3 |
Fibroblast proliferation (%) | ||||
도 1 | Control | SEQ ID NO: 1 | bFGF(100nM) | |
10uM | 50uM | |||
100 | 170 | 194 | 279 | |
도 2 | Control | SEQ ID NO: 2 | bFGF(100nM) | |
10uM | 50uM | |||
100 | 188 | 253 | 400 | |
도 3 | Control | SEQ ID NO: 3 | bFGF(100nM) | |
10uM | 50uM | |||
100 | 194 | 261 | 386 | |
도 4 | Control | SEQ ID NO: 4 | bFGF(100nM) | |
10uM | 50uM | |||
100 | 114 | 193 | 386 |
keratinocyte proliferation (%) | ||||
도 5 | Control | SEQ ID NO: 1 | EGF(10nM) | |
10uM | 50uM | |||
100 | 120 | 136 | 142 | |
도 6 | Control | SEQ ID NO: 2 | EGF(10nM) | |
10uM | 50uM | |||
100 | 111 | 119 | 152 | |
도 7 | Control | SEQ ID NO: 3 | EGF(10nM) | |
10uM | 50uM | |||
100 | 183 | 197 | 187 | |
도 8 | Control | SEQ ID NO: 4 | EGF(10nM) | |
10uM | 50uM | |||
100 | 113 | 142 | 187 |
서열번호 | 프라이머 | 서열(5'-3') |
5 | Collagen1a_F | CACCCTCAAGAGCCTGAGTC |
6 | Collagen1a_R | AGACGGCTGAGTAGGGAACA |
7 | Fibronectin_F | CCAGGAACCGAGTACACCAT |
8 | Fibronectin_R | ATACCCAGGTTGGGTGATGA |
9 | Elastin_F | GGACCCCTGACTCGCGACCT |
10 | Elastin_R | GGGGAGGTGGGACTGCCCAA |
11 | GAPDH_F | GGTGTGAACGGATTTGGCCGTATTG |
12 | GAPDH_R | CCGTTGAATTTGCCGTGAGTGGAGT |
서열번호 | 프라이머 | 서열(5'-3') |
13 | AQP3_F | CCTTCTTGGGTGCTGGAATA |
14 | AQP3_R | ACACGATAAGGGAGGCTCTG |
15 | SIRT1_F | TCAGTGGCTGGAACAGTGAG |
16 | SIRT1_R | TCTGGCATGTCCCACTATCA |
Procollagen1a expression(%) | ||||
도 28 | Control | SEQ ID NO: 1 | IGF-1(100nM) | |
10uM | 50uM | |||
100 | 98 | 157 | 140 | |
도 29 | Control | SEQ ID NO: 2 | IGF-1(100nM) | |
10uM | 50uM | |||
100 | 145 | 146 | 140 | |
도 30 | Control | SEQ ID NO: 3 | IGF-1(100nM) | |
10uM | 50uM | |||
100 | 138 | 143 | 113 | |
도 31 | Control | SEQ ID NO: 4 | IGF-1(100nM) | |
10uM | 50uM | |||
100 | 122 | 141 | 113 |
HA expression(ng/ml) | ||||
도 32 | Control | SEQ ID NO: 2 | IGF-1(100nM) | |
10uM | 50uM | |||
251 | 286 | 292 | 280 |
Claims (8)
- 서열번호 1, 2, 3 또는 4의 아미노산 서열로 이루어진 피부 상태 개선 활성을 갖는 펩타이드.
- 제1항에 있어서, 상기 피부 상태 개선은 주름개선, 피부재생, 피부탄력 개선, 피부노화 억제, 상처 재생, 여드름 개선, 피부 재생 또는 피부 미백인 것인, 펩타이드.
- 서열번호 1의 아미노산 서열로 이루어진 펩타이드, 서열번호 2의 아미노산 서열로 이루어진 펩타이드, 서열번호 3의 아미노산 서열로 이루이전 펩타이드 및 서열번호 4의 아미노산 서열로 이루어진 펩타이드로 이루어진 군에서 선택된 1종 이상의 펩타이드를 포함하는 피부 상태 개선용 화장품 조성물.
- 제3항에 있어서, 상기 피부 상태 개선은 주름개선, 피부재생, 피부탄력 개선, 피부노화 억제, 상처 재생, 여드름 개선, 피부 재생 또는 피부 미백인 것인, 피부 상태 개선용 화장품 조성물.
- 서열번호 1의 아미노산 서열로 이루어진 펩타이드 및 서열번호 2의 아미노산 서열로 이루어진 펩타이드로 이루어진 군에서 선택된 1종 이상의 펩타이드를 포함하는 피부 질환 예방 또는 치료용 약제학적 조성물.
- 제5항에 있어서, 상기 피부 질환은 건선, 아토피성 피부염, 비(非)알러지성 피부염 및 피부 건조증인 것인, 피부 질환 예방 또는 치료용 약제학적 조성물.
- 서열번호 1의 아미노산 서열로 이루어진 펩타이드, 서열번호 2의 아미노산 서열로 이루어진 펩타이드, 서열번호 3의 아미노산 서열로 이루이전 펩타이드 및 서열번호 4의 아미노산 서열로 이루어진 펩타이드로 이루어진 군에서 선택된 1종 이상의 펩타이드를 포함하는 피부 상태 개선용 식품 조성물.
- 제7항에 있어서, 상기 피부 상태 개선은 주름개선, 피부재생, 피부탄력 개선, 피부노화 억제, 상처 재생, 여드름 개선, 피부 재생 또는 피부 미백인 것인, 피부 상태 개선용 식품 조성물.
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US16/642,974 US11103436B2 (en) | 2017-08-31 | 2018-07-03 | Peptide exhibiting wrinkle-improving activity and uses thereof |
CN202311147533.8A CN117186179A (zh) | 2017-08-31 | 2018-07-03 | 一种具有改善皱纹活性的肽及其用途 |
EP24157601.6A EP4349361A2 (en) | 2017-08-31 | 2018-07-03 | Peptide exhibiting wrinkle-improving activity and uses thereof |
EP24157582.8A EP4349359A2 (en) | 2017-08-31 | 2018-07-03 | Peptide exhibiting wrinkle-improving activity and uses thereof |
CN202311152562.3A CN117186180A (zh) | 2017-08-31 | 2018-07-03 | 一种具有改善皱纹活性的肽及其用途 |
EP18850102.7A EP3677590B1 (en) | 2017-08-31 | 2018-07-03 | Peptide exhibiting wrinkle-improving activity and uses thereof |
JP2020512447A JP6944046B2 (ja) | 2017-08-31 | 2018-07-03 | しわ改善活性を示すペプチド及びその用途 |
CN202311147173.1A CN117186175A (zh) | 2017-08-31 | 2018-07-03 | 一种具有改善皱纹活性的肽及其用途 |
BR112020004088-6A BR112020004088A2 (pt) | 2017-08-31 | 2018-07-03 | peptídeo apresentando atividade de melhoria de rugas e usos do mesmo |
EP24157599.2A EP4349360A2 (en) | 2017-08-31 | 2018-07-03 | Peptide exhibiting wrinkle-improving activity and uses thereof |
CN201880056604.4A CN111148751B (zh) | 2017-08-31 | 2018-07-03 | 一种具有改善皱纹活性的肽及其用途 |
US17/389,731 US11672749B2 (en) | 2017-08-31 | 2021-07-30 | Peptide exhibiting wrinkle-improving activity and uses thereof |
US18/308,985 US20230285264A1 (en) | 2017-08-31 | 2023-04-28 | Peptide exhibiting wrinkle-improving activity and uses thereof |
US18/308,908 US20230285263A1 (en) | 2017-08-31 | 2023-04-28 | Peptide exhibiting wrinkle-improving activity and uses thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020170111211A KR101943081B1 (ko) | 2017-08-31 | 2017-08-31 | 주름 개선 활성을 나타내는 펩타이드 및 이의 용도 |
KR10-2017-0111211 | 2017-08-31 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/642,974 A-371-Of-International US11103436B2 (en) | 2017-08-31 | 2018-07-03 | Peptide exhibiting wrinkle-improving activity and uses thereof |
US17/389,731 Continuation US11672749B2 (en) | 2017-08-31 | 2021-07-30 | Peptide exhibiting wrinkle-improving activity and uses thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2019045248A2 true WO2019045248A2 (ko) | 2019-03-07 |
WO2019045248A3 WO2019045248A3 (ko) | 2019-04-18 |
Family
ID=65322932
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2018/007515 WO2019045248A2 (ko) | 2017-08-31 | 2018-07-03 | 주름 개선 활성을 나타내는 펩타이드 및 이의 용도 |
Country Status (7)
Country | Link |
---|---|
US (4) | US11103436B2 (ko) |
EP (4) | EP4349359A2 (ko) |
JP (1) | JP6944046B2 (ko) |
KR (1) | KR101943081B1 (ko) |
CN (4) | CN111148751B (ko) |
BR (1) | BR112020004088A2 (ko) |
WO (1) | WO2019045248A2 (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2023281657A1 (ko) * | 2021-07-07 | 2023-01-12 | ||
EP3611182B1 (en) * | 2017-03-30 | 2024-02-14 | Caregen Co., Ltd. | Peptide having cytoprotective effect against environmental pollutant and use thereof |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101943081B1 (ko) * | 2017-08-31 | 2019-01-29 | (주)케어젠 | 주름 개선 활성을 나타내는 펩타이드 및 이의 용도 |
KR102265430B1 (ko) * | 2019-08-20 | 2021-06-15 | 주식회사 케어젠 | 피부 상태 개선 활성을 갖는 펩타이드 및 이의 용도 |
KR102462330B1 (ko) * | 2020-10-28 | 2022-11-02 | 주식회사 에이엠메딕스 | 피부노화 또는 주름의 예방 또는 개선용 조성물 |
KR102566132B1 (ko) * | 2021-05-18 | 2023-08-14 | 대봉엘에스 주식회사 | 신규 펩타이드 및 이를 포함하는 화장료 조성물 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5516891A (en) | 1992-06-16 | 1996-05-14 | Kinerton, Ltd. | Liquid phase synthesis of peptides and peptide derivatives |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK1064382T3 (da) * | 1998-03-17 | 2008-12-08 | Genentech Inc | Homologe polypeptider til VEGF og BMP1 |
US8344211B2 (en) * | 2008-08-13 | 2013-01-01 | Ceres, Inc. | Plant nucleotide sequences and corresponding polypeptides |
JP4547538B2 (ja) | 2003-10-10 | 2010-09-22 | 独立行政法人産業技術総合研究所 | ダイオキシン結合材料及びダイオキシンの検出又は定量方法 |
TWI496582B (zh) * | 2008-11-24 | 2015-08-21 | 必治妥美雅史谷比公司 | 雙重專一性之egfr/igfir結合分子 |
KR101092915B1 (ko) * | 2009-07-10 | 2011-12-12 | (주)케어젠 | 성장인자―유래 펩타이드 및 이의 용도 |
KR101187871B1 (ko) * | 2009-09-23 | 2012-10-05 | (주)케어젠 | Fgf10-유래 펩타이드 및 그의 용도 |
US20110214205A1 (en) * | 2010-02-26 | 2011-09-01 | Monsanto Technology Llc. | Isolated Novel Nucleic Acid and Protein Molecules from Foxtail Millet and Methods of Using Those Molecules to Generate Transgenic Plants with Enhanced Agronomic Traits |
AU2012208283B2 (en) * | 2011-01-20 | 2017-01-05 | Oneday - Biotech And Pharma Ltd. | Antioxidant, anti-inflammatory, anti-radiation, metal chelating compounds and uses thereof |
KR101363455B1 (ko) | 2011-09-09 | 2014-02-21 | (주)케어젠 | 매트릭스 메탈로프로테아제 활성 억제 펩타이드 및 이의 용도 |
EP2841454A1 (en) * | 2012-04-24 | 2015-03-04 | ThromboGenics N.V. | Anti-pdgf-c antibodies |
KR101573745B1 (ko) | 2013-09-11 | 2015-12-04 | (주)셀아이콘랩 | 콜라겐 합성 촉진 펩타이드, 이의 제조방법, 및, 이를 함유하는 조성물 |
KR20150130616A (ko) | 2014-05-13 | 2015-11-24 | (주)케어젠 | 피부상태 개선 활성을 갖는 펩타이드 및 이의 용도 |
KR101744959B1 (ko) * | 2014-12-05 | 2017-06-12 | (주)케어젠 | 피부상태 개선 활성을 갖는 펩타이드 및 이의 용도 |
CN107667112B (zh) | 2015-05-26 | 2021-12-07 | 珍白斯凯尔有限公司 | 新型肽和含有其的组合物 |
KR101831977B1 (ko) * | 2015-08-25 | 2018-02-23 | (주)피앤피바이오팜 | 상피세포 성장인자의 활성을 가지는 펩타이드 및 그의 용도 |
WO2017043920A1 (ko) * | 2015-09-10 | 2017-03-16 | 한양대학교 산학협력단 | 피부 투과성 펩티드 및 그 이용방법 |
KR101943083B1 (ko) * | 2017-03-30 | 2019-01-29 | (주)케어젠 | 환경오염 물질에 대한 세포 보호 효과를 갖는 펩타이드 및 이의 용도 |
KR101943081B1 (ko) | 2017-08-31 | 2019-01-29 | (주)케어젠 | 주름 개선 활성을 나타내는 펩타이드 및 이의 용도 |
-
2017
- 2017-08-31 KR KR1020170111211A patent/KR101943081B1/ko active IP Right Grant
-
2018
- 2018-07-03 EP EP24157582.8A patent/EP4349359A2/en active Pending
- 2018-07-03 CN CN201880056604.4A patent/CN111148751B/zh active Active
- 2018-07-03 WO PCT/KR2018/007515 patent/WO2019045248A2/ko unknown
- 2018-07-03 US US16/642,974 patent/US11103436B2/en active Active
- 2018-07-03 CN CN202311147533.8A patent/CN117186179A/zh active Pending
- 2018-07-03 CN CN202311152562.3A patent/CN117186180A/zh active Pending
- 2018-07-03 EP EP24157601.6A patent/EP4349361A2/en active Pending
- 2018-07-03 BR BR112020004088-6A patent/BR112020004088A2/pt unknown
- 2018-07-03 CN CN202311147173.1A patent/CN117186175A/zh active Pending
- 2018-07-03 EP EP18850102.7A patent/EP3677590B1/en active Active
- 2018-07-03 EP EP24157599.2A patent/EP4349360A2/en active Pending
- 2018-07-03 JP JP2020512447A patent/JP6944046B2/ja active Active
-
2021
- 2021-07-30 US US17/389,731 patent/US11672749B2/en active Active
-
2023
- 2023-04-28 US US18/308,908 patent/US20230285263A1/en active Pending
- 2023-04-28 US US18/308,985 patent/US20230285264A1/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5516891A (en) | 1992-06-16 | 1996-05-14 | Kinerton, Ltd. | Liquid phase synthesis of peptides and peptide derivatives |
Non-Patent Citations (3)
Title |
---|
"Remington's Pharmaceutical Sciences", 1995 |
MERRIFIELD, J. AMER. CHEM. SOC., vol. 85, 1963, pages 2149 - 54 |
STEWART ET AL.: "Solid Phase Peptide Synthesis", 1984, PIERCE CHEM. CO. |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3611182B1 (en) * | 2017-03-30 | 2024-02-14 | Caregen Co., Ltd. | Peptide having cytoprotective effect against environmental pollutant and use thereof |
JPWO2023281657A1 (ko) * | 2021-07-07 | 2023-01-12 |
Also Published As
Publication number | Publication date |
---|---|
CN117186179A (zh) | 2023-12-08 |
US20230285264A1 (en) | 2023-09-14 |
US20230285263A1 (en) | 2023-09-14 |
WO2019045248A3 (ko) | 2019-04-18 |
US20210369585A1 (en) | 2021-12-02 |
CN111148751B (zh) | 2023-09-05 |
CN117186175A (zh) | 2023-12-08 |
CN111148751A (zh) | 2020-05-12 |
EP4349360A2 (en) | 2024-04-10 |
BR112020004088A2 (pt) | 2020-09-24 |
JP6944046B2 (ja) | 2021-10-06 |
EP3677590B1 (en) | 2024-03-27 |
EP4349361A2 (en) | 2024-04-10 |
EP3677590A4 (en) | 2021-10-06 |
JP2020531558A (ja) | 2020-11-05 |
EP4349359A2 (en) | 2024-04-10 |
US20200197285A1 (en) | 2020-06-25 |
US11103436B2 (en) | 2021-08-31 |
EP3677590A2 (en) | 2020-07-08 |
CN117186180A (zh) | 2023-12-08 |
US11672749B2 (en) | 2023-06-13 |
KR101943081B1 (ko) | 2019-01-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2019045248A2 (ko) | 주름 개선 활성을 나타내는 펩타이드 및 이의 용도 | |
WO2019103203A1 (ko) | 신규 펩티드 및 이를 포함한 조성물 | |
WO2017155232A2 (ko) | 발모 촉진 활성 및/또는 멜라닌 생성 촉진 활성을 나타내는 펩타이드 및 이의 용도 | |
WO2016190660A1 (ko) | 신규 펩티드 및 이를 포함한 조성물 | |
KR101959012B1 (ko) | 주름 개선 활성을 나타내는 펩타이드 및 이의 용도 | |
WO2016088968A1 (ko) | 피부상태 개선 활성을 갖는 펩타이드 및 이의 용도 | |
WO2017105161A2 (ko) | 피부 미백 활성을 갖는 펩타이드 및 이의 용도 | |
WO2017142264A1 (ko) | 멜라닌 생성 촉진 활성을 나타내는 펩타이드 및 이의 용도 | |
WO2017142305A1 (ko) | 발모 촉진 활성 및/또는 멜라닌 생성 촉진 활성을 나타내는 펩타이드 및 이의 용도 | |
WO2017034301A1 (ko) | 상피세포 성장인자의 활성을 가지는 펩타이드 및 그의 용도 | |
WO2017159922A1 (ko) | 피나스테라이드와 펩타이드의 결합체 | |
WO2018199358A1 (ko) | 피부 미백 활성을 갖는 펩타이드 및 이의 용도 | |
WO2018034453A1 (ko) | 미녹시딜과 펩타이드의 결합체 | |
WO2018216884A1 (ko) | 멜라닌 생성 촉진 활성을 나타내는 펩타이드 및 이의 용도 | |
KR101957352B1 (ko) | 주름 개선 활성을 나타내는 펩타이드 및 이의 용도 | |
KR101959020B1 (ko) | 주름 개선 활성을 나타내는 펩타이드 및 이의 용도 | |
WO2018151352A1 (ko) | 살리실산과 펩타이드의 결합체 | |
WO2024106588A1 (ko) | 피부 상태 개선 활성을 갖는 펩타이드 및 이의 용도 | |
WO2024106585A1 (ko) | 피부 상태 개선 활성을 갖는 펩타이드 및 이의 용도 | |
WO2024106587A1 (ko) | 피부 상태 개선 활성을 갖는 펩타이드 및 이의 용도 | |
WO2020226419A2 (ko) | 트롤록스-펩타이드 결합체 및 그의 용도 | |
WO2023127985A1 (ko) | 피부 상태 개선 활성을 갖는 펩타이드 및 이의 용도 | |
WO2023127984A1 (ko) | 피부 상태 개선 활성을 갖는 펩타이드 및 이의 용도 | |
WO2023127986A1 (ko) | 피부 상태 개선 활성을 갖는 펩타이드 및 이의 용도 | |
WO2023127987A1 (ko) | 피부 상태 개선 활성을 갖는 펩타이드 및 이의 용도 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 18850102 Country of ref document: EP Kind code of ref document: A2 |
|
ENP | Entry into the national phase |
Ref document number: 2020512447 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112020004088 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 2018850102 Country of ref document: EP Effective date: 20200331 |
|
ENP | Entry into the national phase |
Ref document number: 112020004088 Country of ref document: BR Kind code of ref document: A2 Effective date: 20200228 |