WO2023186193A1 - Hexapeptide, composition comprising thereof and topical use thereof - Google Patents
Hexapeptide, composition comprising thereof and topical use thereof Download PDFInfo
- Publication number
- WO2023186193A1 WO2023186193A1 PCT/CZ2023/050016 CZ2023050016W WO2023186193A1 WO 2023186193 A1 WO2023186193 A1 WO 2023186193A1 CZ 2023050016 W CZ2023050016 W CZ 2023050016W WO 2023186193 A1 WO2023186193 A1 WO 2023186193A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hexapeptide
- group
- fwahkk
- extract
- composition according
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 62
- 230000000699 topical effect Effects 0.000 title claims abstract description 43
- 125000002811 oleoyl 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])=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])[H] 0.000 claims abstract description 7
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims abstract description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000004472 Lysine Substances 0.000 claims abstract description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 3
- 125000004057 biotinyl group Chemical group [H]N1C(=O)N([H])[C@]2([H])[C@@]([H])(SC([H])([H])[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims abstract description 3
- 210000004899 c-terminal region Anatomy 0.000 claims abstract description 3
- 125000003074 decanoyl group Chemical group [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(*)=O 0.000 claims abstract description 3
- 125000004016 elaidoyl 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])=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])[H] 0.000 claims abstract description 3
- 125000000400 lauroyl 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])[H] 0.000 claims abstract description 3
- 125000003977 lipoyl group Chemical group S1SC(C([H])([H])C(C(C(C(=O)[*])([H])[H])([H])[H])([H])[H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000001419 myristoyl 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])[H] 0.000 claims abstract description 3
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims abstract description 3
- 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 claims abstract description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003696 stearoyl 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])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 45
- 206010000496 acne Diseases 0.000 claims description 45
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 44
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 23
- 239000000284 extract Substances 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 18
- 108090000623 proteins and genes Proteins 0.000 claims description 18
- -1 buter Substances 0.000 claims description 14
- 239000002537 cosmetic Substances 0.000 claims description 11
- 239000003755 preservative agent Substances 0.000 claims description 11
- 230000002335 preservative effect Effects 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 235000014121 butter Nutrition 0.000 claims description 10
- 239000006071 cream Substances 0.000 claims description 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 10
- 210000002966 serum Anatomy 0.000 claims description 10
- 241000894006 Bacteria Species 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 claims description 8
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 241000235070 Saccharomyces Species 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 229940014041 hyaluronate Drugs 0.000 claims description 8
- 102000004169 proteins and genes Human genes 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 7
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 6
- 240000007594 Oryza sativa Species 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- 229920002385 Sodium hyaluronate Polymers 0.000 claims description 6
- 241000209140 Triticum Species 0.000 claims description 6
- 235000021307 Triticum Nutrition 0.000 claims description 6
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- 235000009566 rice Nutrition 0.000 claims description 6
- 229940010747 sodium hyaluronate Drugs 0.000 claims description 6
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 5
- 229940024606 amino acid Drugs 0.000 claims description 5
- 239000003995 emulsifying agent Substances 0.000 claims description 5
- 229920002674 hyaluronan Polymers 0.000 claims description 5
- 229960003160 hyaluronic acid Drugs 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 5
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 5
- 229960004889 salicylic acid Drugs 0.000 claims description 5
- 239000001993 wax Substances 0.000 claims description 5
- WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 claims description 4
- LUEWUZLMQUOBSB-FSKGGBMCSA-N (2s,3s,4s,5s,6r)-2-[(2r,3s,4r,5r,6s)-6-[(2r,3s,4r,5s,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5s,6r)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 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]2[C@H](O[C@@H](OC3[C@H](O[C@@H](O)[C@@H](O)[C@H]3O)CO)[C@@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-FSKGGBMCSA-N 0.000 claims description 4
- AJLNZWYOJAWBCR-OOPVGHQCSA-N (4s)-4-acetamido-5-[[(2s)-1-[[(2s)-1-[[(2s)-5-amino-1-[[(2s)-1-[[(2s)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-car Chemical compound OC(=O)CC[C@H](NC(C)=O)C(=C)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCN=C(N)N)C(N)=O AJLNZWYOJAWBCR-OOPVGHQCSA-N 0.000 claims description 4
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 claims description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 4
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 claims description 4
- 240000001538 Agaricus subrufescens Species 0.000 claims description 4
- 235000008610 Agaricus subrufescens Nutrition 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 4
- 241000186000 Bifidobacterium Species 0.000 claims description 4
- BYUQATUKPXLFLZ-UIOOFZCWSA-N CCCCCCCCCCCCCCCC(=O)NCC(=O)N[C@H](C(=O)N[C@@H](CCCCN)C(O)=O)CC1=CN=CN1 Chemical compound CCCCCCCCCCCCCCCC(=O)NCC(=O)N[C@H](C(=O)N[C@@H](CCCCN)C(O)=O)CC1=CN=CN1 BYUQATUKPXLFLZ-UIOOFZCWSA-N 0.000 claims description 4
- 240000006162 Chenopodium quinoa Species 0.000 claims description 4
- 241000180254 Choiromyces Species 0.000 claims description 4
- 241000195493 Cryptophyta Species 0.000 claims description 4
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 claims description 4
- 235000001637 Ganoderma lucidum Nutrition 0.000 claims description 4
- 240000008397 Ganoderma lucidum Species 0.000 claims description 4
- 229920002581 Glucomannan Polymers 0.000 claims description 4
- 235000007710 Grifola frondosa Nutrition 0.000 claims description 4
- 240000001080 Grifola frondosa Species 0.000 claims description 4
- 241000205062 Halobacterium Species 0.000 claims description 4
- 241001534813 Hypsizygus Species 0.000 claims description 4
- 241000186660 Lactobacillus Species 0.000 claims description 4
- 240000000599 Lentinula edodes Species 0.000 claims description 4
- 235000001715 Lentinula edodes Nutrition 0.000 claims description 4
- 241001248610 Ophiocordyceps sinensis Species 0.000 claims description 4
- 244000025272 Persea americana Species 0.000 claims description 4
- 235000008673 Persea americana Nutrition 0.000 claims description 4
- 241000222640 Polyporus Species 0.000 claims description 4
- 229920002305 Schizophyllan Polymers 0.000 claims description 4
- 241000222481 Schizophyllum commune Species 0.000 claims description 4
- 241000425108 Thalassospira Species 0.000 claims description 4
- 241000222355 Trametes versicolor Species 0.000 claims description 4
- 241000908178 Tremella fuciformis Species 0.000 claims description 4
- 229940000957 acai extract Drugs 0.000 claims description 4
- 235000015800 acai extract Nutrition 0.000 claims description 4
- 229940095094 acetyl hexapeptide-8 Drugs 0.000 claims description 4
- 108010006338 acetyl-glutamyl-glutamyl-methionyl-glutaminyl-arginyl-argininamide Proteins 0.000 claims description 4
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 4
- 235000014104 aloe vera supplement Nutrition 0.000 claims description 4
- 235000001014 amino acid Nutrition 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- QMIFIFIYYPUVNU-ACMTZBLWSA-L copper (2S)-6-amino-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-imidazol-1-id-4-ylpropanoyl]amino]hexanoate Chemical compound [Cu+2].NCCCC[C@@H](C([O-])=O)NC(=O)[C@@H](NC(=O)CN)CC1=C[N-]C=N1 QMIFIFIYYPUVNU-ACMTZBLWSA-L 0.000 claims description 4
- 235000020237 cranberry extract Nutrition 0.000 claims description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 claims description 4
- 229940046240 glucomannan Drugs 0.000 claims description 4
- 150000004676 glycans Chemical class 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 229940094952 green tea extract Drugs 0.000 claims description 4
- 235000020688 green tea extract Nutrition 0.000 claims description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-UHFFFAOYSA-N hexopyranose Chemical compound OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 claims description 4
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940039696 lactobacillus Drugs 0.000 claims description 4
- 239000000787 lecithin Substances 0.000 claims description 4
- 235000010445 lecithin Nutrition 0.000 claims description 4
- 229940067606 lecithin Drugs 0.000 claims description 4
- 240000004308 marijuana Species 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- 229940093441 palmitoyl oligopeptide Drugs 0.000 claims description 4
- 229940101267 panthenol Drugs 0.000 claims description 4
- 235000020957 pantothenol Nutrition 0.000 claims description 4
- 239000011619 pantothenol Substances 0.000 claims description 4
- 239000000419 plant extract Substances 0.000 claims description 4
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 4
- 229920001282 polysaccharide Polymers 0.000 claims description 4
- 239000005017 polysaccharide Substances 0.000 claims description 4
- 229940068968 polysorbate 80 Drugs 0.000 claims description 4
- 229920000053 polysorbate 80 Polymers 0.000 claims description 4
- 125000001444 retinoyl group Chemical group O=C([*])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 208000017520 skin disease Diseases 0.000 claims description 4
- 229940047670 sodium acrylate Drugs 0.000 claims description 4
- 229940088594 vitamin Drugs 0.000 claims description 4
- 229930003231 vitamin Natural products 0.000 claims description 4
- 235000013343 vitamin Nutrition 0.000 claims description 4
- 239000011782 vitamin Substances 0.000 claims description 4
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 claims description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 239000004287 Dehydroacetic acid Substances 0.000 claims description 3
- 241000414067 Inonotus obliquus Species 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 159000000032 aromatic acids Chemical class 0.000 claims description 3
- 229960002255 azelaic acid Drugs 0.000 claims description 3
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 229960004365 benzoic acid Drugs 0.000 claims description 3
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 3
- 235000019258 dehydroacetic acid Nutrition 0.000 claims description 3
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 claims description 3
- 229940061632 dehydroacetic acid Drugs 0.000 claims description 3
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 3
- 229940091173 hydantoin Drugs 0.000 claims description 3
- 150000002460 imidazoles Chemical class 0.000 claims description 3
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 claims description 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 3
- 239000006166 lysate Substances 0.000 claims description 3
- 229960005323 phenoxyethanol Drugs 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000004302 potassium sorbate Substances 0.000 claims description 3
- 235000010241 potassium sorbate Nutrition 0.000 claims description 3
- 229940069338 potassium sorbate Drugs 0.000 claims description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 3
- 239000004299 sodium benzoate Substances 0.000 claims description 3
- 235000010234 sodium benzoate Nutrition 0.000 claims description 3
- 229960003885 sodium benzoate Drugs 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229960005349 sulfur Drugs 0.000 claims description 3
- WTVHAMTYZJGJLJ-UHFFFAOYSA-N (+)-(4S,8R)-8-epi-beta-bisabolol Natural products CC(C)=CCCC(C)C1(O)CCC(C)=CC1 WTVHAMTYZJGJLJ-UHFFFAOYSA-N 0.000 claims description 2
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 claims description 2
- IHRKJQSLKLYWBQ-QKDODKLFSA-N (2s)-2-[[(2s)-1-[(2s)-5-amino-2-[[2-(hexadecanoylamino)acetyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(O)=O IHRKJQSLKLYWBQ-QKDODKLFSA-N 0.000 claims description 2
- WSGCRSMLXFHGRM-DEVHWETNSA-N (2s)-2-[[(2s)-6-amino-2-[[(2s,3r)-2-[[(2s,3r)-2-[[(2s)-6-amino-2-(hexadecanoylamino)hexanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-3-hydroxypropanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(O)=O WSGCRSMLXFHGRM-DEVHWETNSA-N 0.000 claims description 2
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 claims description 2
- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 claims description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 2
- NKEQOUMMGPBKMM-UHFFFAOYSA-N 2-hydroxy-2-[2-(2-hydroxy-3-octadecanoyloxypropoxy)-2-oxoethyl]butanedioic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CC(O)(C(O)=O)CC(O)=O NKEQOUMMGPBKMM-UHFFFAOYSA-N 0.000 claims description 2
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims description 2
- 244000247812 Amorphophallus rivieri Species 0.000 claims description 2
- 235000001206 Amorphophallus rivieri Nutrition 0.000 claims description 2
- 244000144725 Amygdalus communis Species 0.000 claims description 2
- 235000011437 Amygdalus communis Nutrition 0.000 claims description 2
- 244000125300 Argania sideroxylon Species 0.000 claims description 2
- 241000454552 Astrocaryum murumuru Species 0.000 claims description 2
- LFYJSSARVMHQJB-UHFFFAOYSA-N Backuchiol Natural products CC(C)=CCCC(C)(C=C)C=CC1=CC=C(O)C=C1 LFYJSSARVMHQJB-UHFFFAOYSA-N 0.000 claims description 2
- 235000004936 Bromus mango Nutrition 0.000 claims description 2
- 244000025254 Cannabis sativa Species 0.000 claims description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 2
- 244000060011 Cocos nucifera Species 0.000 claims description 2
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims description 2
- 235000010919 Copernicia prunifera Nutrition 0.000 claims description 2
- 244000180278 Copernicia prunifera Species 0.000 claims description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims description 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
- 229920002907 Guar gum Polymers 0.000 claims description 2
- 244000020551 Helianthus annuus Species 0.000 claims description 2
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
- 229920002752 Konjac Polymers 0.000 claims description 2
- 239000004166 Lanolin Substances 0.000 claims description 2
- 241001072282 Limnanthes Species 0.000 claims description 2
- 241000208467 Macadamia Species 0.000 claims description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 2
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 claims description 2
- 235000014826 Mangifera indica Nutrition 0.000 claims description 2
- 240000007228 Mangifera indica Species 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- 235000008753 Papaver somniferum Nutrition 0.000 claims description 2
- 240000001090 Papaver somniferum Species 0.000 claims description 2
- 239000004264 Petrolatum Substances 0.000 claims description 2
- 235000009827 Prunus armeniaca Nutrition 0.000 claims description 2
- 244000018633 Prunus armeniaca Species 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 239000004373 Pullulan Substances 0.000 claims description 2
- 229920001218 Pullulan Polymers 0.000 claims description 2
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 claims description 2
- 240000003935 Sclerocarya birrea Species 0.000 claims description 2
- 235000001836 Sclerocarya caffra Nutrition 0.000 claims description 2
- 241001558929 Sclerotium <basidiomycota> Species 0.000 claims description 2
- 235000003434 Sesamum indicum Nutrition 0.000 claims description 2
- 244000040738 Sesamum orientale Species 0.000 claims description 2
- 244000044822 Simmondsia californica Species 0.000 claims description 2
- 235000004433 Simmondsia californica Nutrition 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims description 2
- 108010073771 Soybean Proteins Proteins 0.000 claims description 2
- 235000009184 Spondias indica Nutrition 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 2
- 229930003270 Vitamin B Natural products 0.000 claims description 2
- 229930003268 Vitamin C Natural products 0.000 claims description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims description 2
- 229960000458 allantoin Drugs 0.000 claims description 2
- 235000020224 almond Nutrition 0.000 claims description 2
- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 claims description 2
- 201000008937 atopic dermatitis Diseases 0.000 claims description 2
- LFYJSSARVMHQJB-GOSISDBHSA-N bakuchinol Natural products CC(C)=CCC[C@@](C)(C=C)C=CC1=CC=C(O)C=C1 LFYJSSARVMHQJB-GOSISDBHSA-N 0.000 claims description 2
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 claims description 2
- 229940117895 bakuchiol Drugs 0.000 claims description 2
- KXXXNMZPAJTCQY-UHFFFAOYSA-N bakuchiol Natural products CC(C)CCCC(C)(C=C)C=Cc1ccc(O)cc1 KXXXNMZPAJTCQY-UHFFFAOYSA-N 0.000 claims description 2
- 235000013871 bee wax Nutrition 0.000 claims description 2
- 239000012166 beeswax Substances 0.000 claims description 2
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 2
- 229940036350 bisabolol Drugs 0.000 claims description 2
- HHGZABIIYIWLGA-UHFFFAOYSA-N bisabolol Natural products CC1CCC(C(C)(O)CCC=C(C)C)CC1 HHGZABIIYIWLGA-UHFFFAOYSA-N 0.000 claims description 2
- 235000009120 camo Nutrition 0.000 claims description 2
- 235000013868 candelilla wax Nutrition 0.000 claims description 2
- 239000004204 candelilla wax Substances 0.000 claims description 2
- 229940073532 candelilla wax Drugs 0.000 claims description 2
- 229960001631 carbomer Drugs 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 229940081733 cetearyl alcohol Drugs 0.000 claims description 2
- 229960000541 cetyl alcohol Drugs 0.000 claims description 2
- 235000005607 chanvre indien Nutrition 0.000 claims description 2
- 229940110456 cocoa butter Drugs 0.000 claims description 2
- 235000019868 cocoa butter Nutrition 0.000 claims description 2
- 235000017471 coenzyme Q10 Nutrition 0.000 claims description 2
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims description 2
- 229940110767 coenzyme Q10 Drugs 0.000 claims description 2
- 229910001431 copper ion Inorganic materials 0.000 claims description 2
- 229960000735 docosanol Drugs 0.000 claims description 2
- 229930182478 glucoside Natural products 0.000 claims description 2
- 150000008131 glucosides Chemical class 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 229940049654 glyceryl behenate Drugs 0.000 claims description 2
- 229940087068 glyceryl caprylate Drugs 0.000 claims description 2
- 229940075529 glyceryl stearate Drugs 0.000 claims description 2
- 239000000665 guar gum Substances 0.000 claims description 2
- 235000010417 guar gum Nutrition 0.000 claims description 2
- 229960002154 guar gum Drugs 0.000 claims description 2
- 229920000591 gum Polymers 0.000 claims description 2
- 239000011487 hemp Substances 0.000 claims description 2
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 claims description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 229940071826 hydroxyethyl cellulose Drugs 0.000 claims description 2
- 206010021198 ichthyosis Diseases 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 229960000448 lactic acid Drugs 0.000 claims description 2
- 235000019388 lanolin Nutrition 0.000 claims description 2
- 229940039717 lanolin Drugs 0.000 claims description 2
- 229910001425 magnesium ion Inorganic materials 0.000 claims description 2
- 229910001437 manganese ion Inorganic materials 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 2
- 229940094946 palmitoyl tetrapeptide-7 Drugs 0.000 claims description 2
- 201000003042 peeling skin syndrome Diseases 0.000 claims description 2
- 235000019271 petrolatum Nutrition 0.000 claims description 2
- 229940066842 petrolatum Drugs 0.000 claims description 2
- 229920000136 polysorbate Polymers 0.000 claims description 2
- 229950008882 polysorbate Drugs 0.000 claims description 2
- 235000019423 pullulan Nutrition 0.000 claims description 2
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 claims description 2
- 235000021283 resveratrol Nutrition 0.000 claims description 2
- 229940016667 resveratrol Drugs 0.000 claims description 2
- 229950004959 sorbitan oleate Drugs 0.000 claims description 2
- 229940001941 soy protein Drugs 0.000 claims description 2
- 229940114926 stearate Drugs 0.000 claims description 2
- 229960004274 stearic acid Drugs 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 235000001508 sulfur Nutrition 0.000 claims description 2
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims description 2
- 235000019155 vitamin A Nutrition 0.000 claims description 2
- 239000011719 vitamin A Substances 0.000 claims description 2
- 235000019156 vitamin B Nutrition 0.000 claims description 2
- 239000011720 vitamin B Substances 0.000 claims description 2
- 235000019154 vitamin C Nutrition 0.000 claims description 2
- 239000011718 vitamin C Substances 0.000 claims description 2
- 229920001285 xanthan gum Polymers 0.000 claims description 2
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 claims 1
- 201000004700 rosacea Diseases 0.000 claims 1
- 210000004927 skin cell Anatomy 0.000 abstract description 5
- 239000003623 enhancer Substances 0.000 abstract description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 70
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 66
- 239000011701 zinc Substances 0.000 description 47
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 35
- 229960003471 retinol Drugs 0.000 description 35
- 235000020944 retinol Nutrition 0.000 description 35
- 239000011607 retinol Substances 0.000 description 35
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 34
- 229910052725 zinc Inorganic materials 0.000 description 33
- 230000014509 gene expression Effects 0.000 description 23
- 210000002510 keratinocyte Anatomy 0.000 description 22
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 21
- 229910000368 zinc sulfate Inorganic materials 0.000 description 21
- 239000011686 zinc sulphate Substances 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 19
- 241000186427 Cutibacterium acnes Species 0.000 description 18
- 210000003491 skin Anatomy 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 210000002374 sebum Anatomy 0.000 description 12
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 230000000845 anti-microbial effect Effects 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 235000009529 zinc sulphate Nutrition 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 7
- 230000004054 inflammatory process Effects 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000008506 pathogenesis Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000010972 statistical evaluation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 206010040954 Skin wrinkling Diseases 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
- 239000003098 androgen Substances 0.000 description 6
- 230000003712 anti-aging effect Effects 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 230000003833 cell viability Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229940068196 placebo Drugs 0.000 description 6
- 239000000902 placebo Substances 0.000 description 6
- 230000000770 proinflammatory effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 102100022289 60S ribosomal protein L13a Human genes 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 102000008186 Collagen Human genes 0.000 description 5
- 108010035532 Collagen Proteins 0.000 description 5
- 101000681240 Homo sapiens 60S ribosomal protein L13a Proteins 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- 102000015696 Interleukins Human genes 0.000 description 5
- 108010063738 Interleukins Proteins 0.000 description 5
- 230000003255 anti-acne Effects 0.000 description 5
- 229920001436 collagen Polymers 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000004069 differentiation Effects 0.000 description 5
- 238000003633 gene expression assay Methods 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 101000640855 Homo sapiens 3-oxo-5-alpha-steroid 4-dehydrogenase 1 Proteins 0.000 description 4
- 102000004890 Interleukin-8 Human genes 0.000 description 4
- 108090001007 Interleukin-8 Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000000638 stimulation Effects 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 3
- UOFGSWVZMUXXIY-UHFFFAOYSA-N 1,5-Diphenyl-3-thiocarbazone Chemical compound C=1C=CC=CC=1N=NC(=S)NNC1=CC=CC=C1 UOFGSWVZMUXXIY-UHFFFAOYSA-N 0.000 description 3
- 108700042778 Antimicrobial Peptides Proteins 0.000 description 3
- 102000044503 Antimicrobial Peptides Human genes 0.000 description 3
- 240000005528 Arctium lappa Species 0.000 description 3
- 235000003130 Arctium lappa Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 206010015150 Erythema Diseases 0.000 description 3
- 239000003875 Wang resin Substances 0.000 description 3
- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002730 additional effect Effects 0.000 description 3
- 229940030486 androgens Drugs 0.000 description 3
- 239000006143 cell culture medium Substances 0.000 description 3
- 231100000433 cytotoxic Toxicity 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 3
- IJMVGIBIGDBVLY-FIFJRYGNSA-N epinecidin-1 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCSC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)CC)C1=CN=CN1 IJMVGIBIGDBVLY-FIFJRYGNSA-N 0.000 description 3
- 210000002950 fibroblast Anatomy 0.000 description 3
- 229940047122 interleukins Drugs 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 229940055019 propionibacterium acne Drugs 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229960003604 testosterone Drugs 0.000 description 3
- 239000001974 tryptic soy broth Substances 0.000 description 3
- 108010050327 trypticase-soy broth Proteins 0.000 description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 101150084750 1 gene Proteins 0.000 description 2
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- 235000008078 Arctium minus Nutrition 0.000 description 2
- 101800001873 Bombinin-like peptide 7 Proteins 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 101000702089 Homo sapiens Small proline-rich protein 2E Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000134 MTT assay Methods 0.000 description 2
- 231100000002 MTT assay Toxicity 0.000 description 2
- 241001608711 Melo Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 206010040844 Skin exfoliation Diseases 0.000 description 2
- 102100030319 Small proline-rich protein 2E Human genes 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 102000001307 androgen receptors Human genes 0.000 description 2
- 108010080146 androgen receptors Proteins 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000001153 anti-wrinkle effect Effects 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 230000001815 facial effect Effects 0.000 description 2
- 230000003325 follicular Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 238000010191 image analysis Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 230000000485 pigmenting effect Effects 0.000 description 2
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 230000001172 regenerating effect Effects 0.000 description 2
- 230000003716 rejuvenation Effects 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
- 230000004936 stimulating effect Effects 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- 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
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- NGEZPLCPKXKLQQ-VOTSOKGWSA-N (e)-4-(3-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=CC(\C=C\C(C)=O)=C1 NGEZPLCPKXKLQQ-VOTSOKGWSA-N 0.000 description 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 1
- 102100034254 3-oxo-5-alpha-steroid 4-dehydrogenase 1 Human genes 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 101710099705 Anti-lipopolysaccharide factor Proteins 0.000 description 1
- 108010050820 Antimicrobial Cationic Peptides Proteins 0.000 description 1
- 102000014133 Antimicrobial Cationic Peptides Human genes 0.000 description 1
- 101710174584 Ascaphin-8 Proteins 0.000 description 1
- 108010062877 Bacteriocins Proteins 0.000 description 1
- 241000269340 Bombina orientalis Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241000272081 Bungarus fasciatus Species 0.000 description 1
- 101000741302 Bungarus fasciatus Cathelicidin-related antimicrobial peptide Bf-CRAMP Proteins 0.000 description 1
- 101150008656 COL1A1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 108010004103 Chylomicrons Proteins 0.000 description 1
- 102100033601 Collagen alpha-1(I) chain Human genes 0.000 description 1
- 244000117499 Colubrina elliptica Species 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 101100075837 Drosophila melanogaster Mabi gene Proteins 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 108010037349 Epinephelus coioides epinecidin-1 Proteins 0.000 description 1
- 102100024785 Fibroblast growth factor 2 Human genes 0.000 description 1
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 1
- 102100021186 Granulysin Human genes 0.000 description 1
- 101710168479 Granulysin Proteins 0.000 description 1
- 241000589989 Helicobacter Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101001002634 Homo sapiens Interleukin-1 alpha Proteins 0.000 description 1
- 101000975474 Homo sapiens Keratin, type I cytoskeletal 10 Proteins 0.000 description 1
- 101100181426 Homo sapiens LCE2C gene Proteins 0.000 description 1
- 101001086785 Homo sapiens Occludin Proteins 0.000 description 1
- 101150097648 Il1a gene Proteins 0.000 description 1
- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 1
- 102100023970 Keratin, type I cytoskeletal 10 Human genes 0.000 description 1
- 102100024560 Late cornified envelope protein 2C Human genes 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101710164547 Moronecidin Proteins 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 102100032604 Occludin Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 238000011529 RT qPCR Methods 0.000 description 1
- NCYCYZXNIZJOKI-OVSJKPMPSA-N Retinaldehyde Chemical compound O=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 description 1
- 241000194024 Streptococcus salivarius Species 0.000 description 1
- 241000258185 Strongylocentrotus droebachiensis Species 0.000 description 1
- 239000012163 TRI reagent Substances 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 108010057266 Type A Botulinum Toxins Proteins 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 241001135917 Vitellaria paradoxa Species 0.000 description 1
- OGQICQVSFDPSEI-UHFFFAOYSA-N Zorac Chemical compound N1=CC(C(=O)OCC)=CC=C1C#CC1=CC=C(SCCC2(C)C)C2=C1 OGQICQVSFDPSEI-UHFFFAOYSA-N 0.000 description 1
- KPFBUSLHFFWMAI-HYRPPVSQSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-6-formyl-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1C[C@@H]2[C@](CCC(OC)=C3)(C)C3=C(C=O)C[C@H]2[C@@H]2CC[C@](OC(C)=O)(C(C)=O)[C@]21C KPFBUSLHFFWMAI-HYRPPVSQSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229960002916 adapalene Drugs 0.000 description 1
- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 108010029483 alpha 1 Chain Collagen Type I Proteins 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000058 anti acne agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 229940124340 antiacne agent Drugs 0.000 description 1
- 239000000051 antiandrogen Substances 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- HKSIJFPILGFPDG-GAQAHWELSA-N ascaphin-8 Chemical compound C([C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)CN)C1=CC=CC=C1 HKSIJFPILGFPDG-GAQAHWELSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000002368 bacteriocinic effect Effects 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007698 birth defect Effects 0.000 description 1
- 229940089093 botox Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000006037 cell lysis Effects 0.000 description 1
- PQJQFLNBMSCUSH-SBAJWEJLSA-N chembl2364632 Chemical compound O=C1C2=C(O)[C@@](C(C(C(N)=O)=C(O)[C@H]3N(C)C)=O)(O)[C@H]3C[C@@H]2CC2=C1C(O)=CC=C2CN(C)OC PQJQFLNBMSCUSH-SBAJWEJLSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229960002227 clindamycin Drugs 0.000 description 1
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
- 230000037319 collagen production Effects 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000035618 desquamation Effects 0.000 description 1
- JIONSDIFUGDYLD-UHFFFAOYSA-N diaminomethylideneazanium;phenol;thiocyanate Chemical compound [S-]C#N.NC([NH3+])=N.OC1=CC=CC=C1 JIONSDIFUGDYLD-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229960003722 doxycycline Drugs 0.000 description 1
- XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- LCFXLZAXGXOXAP-DAXSKMNVSA-N ethyl (2z)-2-cyano-2-hydroxyiminoacetate Chemical compound CCOC(=O)C(=N/O)\C#N LCFXLZAXGXOXAP-DAXSKMNVSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 0.000 description 1
- 210000003780 hair follicle Anatomy 0.000 description 1
- 229940076153 heptahydrate zinc sulfate Drugs 0.000 description 1
- 238000010842 high-capacity cDNA reverse transcription kit Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960005280 isotretinoin Drugs 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- DYKFCLLONBREIL-KVUCHLLUSA-N minocycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O DYKFCLLONBREIL-KVUCHLLUSA-N 0.000 description 1
- 229960004023 minocycline Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 239000007908 nanoemulsion Substances 0.000 description 1
- 239000002121 nanofiber Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000002077 nanosphere Substances 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000013800 negative regulation of keratinocyte differentiation Effects 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 108010075334 omiganan pentahydrochloride Proteins 0.000 description 1
- WTNSIKUBZJCPLJ-IQOWARLESA-N omiganan pentahydrochloride Chemical compound Cl.Cl.Cl.Cl.Cl.C1=CC=C2C(C[C@H](NC(=O)[C@@H]3CCCN3C(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H]3CCCN3C(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)[C@@H](C)CC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(N)=O)=CNC2=C1 WTNSIKUBZJCPLJ-IQOWARLESA-N 0.000 description 1
- 229940127249 oral antibiotic Drugs 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000007030 peptide scission Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000003753 real-time PCR Methods 0.000 description 1
- 235000020945 retinal Nutrition 0.000 description 1
- 239000011604 retinal Substances 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- 238000010839 reverse transcription Methods 0.000 description 1
- 238000003757 reverse transcription PCR Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229950000534 sarecycline Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000004378 sebocyte Anatomy 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 230000036620 skin dryness Effects 0.000 description 1
- 244000005714 skin microbiome Species 0.000 description 1
- 230000036555 skin type Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960000565 tazarotene Drugs 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- 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
-
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
-
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/27—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/99—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from microorganisms other than algae or fungi, e.g. protozoa or bacteria
-
- 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
- A61P17/06—Antipsoriatics
-
- 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
- A61P17/10—Anti-acne agents
-
- 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
-
- 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
Definitions
- the present invention relates to the artificially designed peptide of the sequence X-Phe- Trp-Ala-His-Lys-Lys-Z, derivatives or complexes with metal ions thereof, a topical composition comprising thereof and topical use thereof. It relates more particularly to use of the peptides for the treatment of the skin of humans or animals for cosmetic or dermo- pharmaceutical purposes.
- Acne vulgaris (henceforth acne) is a very common chronic skin disease of the pilosebaceous unit with profound negative psychosocial impact on the quality of life of patients. Although it affects individuals of all ages, it usually appears during adolescence and frequently persists into the adulthood (Yentzer et al. 2010).
- the pathogenesis of acne vulgaris is multifactorial with four core events: hyperseborrhoea, epithelial hyperproliferation and hyperkeratinization, Cutibacterium acnes colonization, and inflammation.
- Another typical event in acne pathogenesis is hyperproliferation of follicular keratinocytes and their abnormal differentiation (Thiboutot 2000).
- the latter is associated with increased cohesiveness of comeocytes leading to their impaired desquamation (Thiboutot 2000).
- the accumulated mass of keratinized comeocytes together with sebum partially obstructs follicles resulting in their extension and creating favorable conditions for the growth of C. acnes (Thiboutot 2000).
- C. acnes is a bacterium living in and on the human skin as part of the normal human skin microbiome. It predominantly resides deep within the sebaceous follicle in contact with keratinocytes.
- C. acnes plays a significant role in the pathogenesis of acne (McLaughlin et al. 2019). It seems, that for acne development the overall C. acnes number is not as important as the presence of certain C. acnes strains (Dreno et al. 2018). These acne- associated strains were shown to be more virulent and produce a large number of various pro- inflammatory factors (Dreno et al. 2018). Inflammation
- Inflammation is regarded as a key part in the pathogenesis of acne.
- inflammation was thought to be a secondary event induced by C. acnes colonization.
- Recently, inflammatory processes are suggested to be involved in all stages of acne development and acne is nowadays considered as genuinely inflammatory disease (Tanghetti 2013).
- a combination of a topical retinoid tretinoin, isotretinoin, adapalene, tazarotene, retinol, retinaldehyde etc.
- an antimicrobial agent e.g. benzoyl peroxide
- Hormonal, anti-androgen therapy oral contraceptives, spironolactone is often given to women to reduce sebum production.
- Topical or oral antibiotics are used in treatment of moderate-to-severe acne usually in combination with benzoyl peroxide or retinoids.
- topical anti-acne agents salicylic acid, azelaic acid, zinc, sulfur, niacinamide, glycolic acid and antimicrobial peptides can be mentioned (Liu et al. 2020).
- Zinc level in acne patients is often significantly lower and its supplementation (oral or topical) have been shown to improve acne (Yee et al. 2020). Although its exact mechanism of action is not fully understood, current knowledge suggests multiple mechanisms including anti- inflammatory, antioxidant effects, inhibition of C. acnes proliferation and inhibition of 5 a- reductase leading to reduced sebum production in vivo (Abendrot and Kalinowska-Lis 2018; Cervantes et al. 2018).
- AMP antimicrobial
- Frog skin-derived AMP [D4k]ascaphin-8, [G4K]XT-7, [T5k]temporin-DRa, brevinin- 2GU, and B2RP-Era (Popovic et al. 2012)
- Bombinin-like peptide 7 (BLP-7) from Bombina orientalis (Wu et al. 2020)
- Cathelicidin-BF has been purified from the snake venoms of Bungarus fasciatus (Wang et al. 2011)
- Bacteriocin-like inhibitory substance produced by Streptococcus salivarius (Bowe et al. 2006)
- KR20200101767A Peptide having anti-microbial activity and compositions for anti- microbial comprising the same KTTKS
- the subject-matter of the invention concerns a hexapeptide having a general formula I
- X is -NHX 1 group of phenylalanine at the N-terminal end of the hexapeptide, wherein
- X 1 is selected from a group comprising H, acetyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, elaidoyl, oleoyl, biotinoyl or lipoyl.
- X 1 is H.
- Z is -COZ 1 group of lysine at the C-terminal end of the hexapeptide, wherein Z 1 is selected from a group comprising OH, OCH 3 , OCH 2 CH 3 or NH 2 .
- Z 1 is OH.
- the hexapeptide according to the present invention is preferably the enhancer of the skin cells so that it can be applied topically in the skin and it can be called also the topical hexapeptide.
- the hexapeptide of the general formula I according to the present invention is preferably in a form of a complex with a metal ion selected from a group comprising zinc ion, copper ion, manganese ion or magnesium ion.
- the metal ion is bound by a coordination covalent bond in the complex.
- metal ion is zinc ion (Zn 2+ ) and the complex is schematically stated below as Zn-FWAHKK complex or simply as Zn-FWAHKK.
- the hexapeptide of the general formula I according to the present invention may be optically pure or be composed of L- or D-isomers or a mixture thereof. L-isomers, which are those found in nature, are preferred.
- the hexapeptide of the present invention may be in the form of salts, especially salts of hydrochloric acid, formic acid or acetic acid, or any salts commonly used in cosmetics.
- Another embodiment according to the present invention is a topical composition comprising at least one hexapeptide of the general formula I as defined above.
- a concentration of the hexapeptide of the general formula I is in the range of 0.0001 to 0.135 % (w/w), preferably in the range of 0.001 to 0.05 % (w/w), more preferably from 0.001 to 0.0135 % (w/w).
- Amount of the hexapeptide depends on the purpose of the composition and the desired final effect.
- This invention also includes the topical composition, that contains at least one hexapeptide according to the invention in a form for the topical skin application that may be selected from a group comprising cream, serum, anhydrous gel, paste, dispersion of vesicles, powder, nanofibers, macro-, micro-, or nano-capsules, macro-, micro- or nano-spheres, liposomes, oleosomes or chylomicrons, macro-, micro-, or nanoparticles or macro-, micro- or nano-sponges, which may be adsorbed on organic polymer powders, talcs, bentonites and other inorganic or organic supports.
- a group comprising cream, serum, anhydrous gel, paste, dispersion of vesicles, powder, nanofibers, macro-, micro-, or nano-capsules, macro-, micro- or nano-spheres, liposomes, oleosomes or chylomicrons, macro-, micro-, or nanoparticles
- the topical composition according to the present invention is in the form of the cream selected from a group comprising a water-in-oil or oil-in-water emulsion, a micro- or nano- emulsion.
- the topical composition according to the present invention is in the form of the serum selected from a group comprising sterile or nonsterile aqueous or hydro-alcoholic solution or gel.
- the composition is in a form selected from a group comprising cream or serum.
- the concentration of the hexapeptide of the general formula I is in the range of 0.0001 to 0.135 % (w/w), preferably 0.001 % to 0.0135 % (w/w).
- composition in the form of cream additionally comprises at least one cosmetic or dermo-pharmaceutical auxiliary ingredient selected from a group comprising oil, wax, butter, emulsifier, auxiliary active ingredient and preservative.
- cosmetic or dermo-pharmaceutical auxiliary ingredient selected from a group comprising oil, wax, butter, emulsifier, auxiliary active ingredient and preservative.
- the amount of oil, wax, butter or a mixture thereof in the composition according to the present invention is in the range of 20 to 55 % (w/w), preferably 20 to 40 % (w/w), more preferably 20 to 30 % (w/w).
- the amount of emulsifier in the composition according to the present invention is in the range of 1 to 20 % (w/w), preferably 2-15 % (w/w), more preferably 2-10 % (w/w).
- the amount of auxiliary active ingredient in the composition according to the present invention is in the range of 0.001 to 20 % (w/w), preferably 0.001 to 10 % (w/w), more preferably 0.001 to 5 % (w/w).
- the amount of preservative in the composition according to the present invention is in the range of 0.1 to 2.5 % (w/w), preferably 0.1 to 1.5 % (w/w), more preferably 0.8 to 1.2 % (w/w).
- the oil is selected from a group comprising argan, coconut, avocado, almond, sesame, olive, sunflower, hemp, jojoba, macadamia, wheat germ, marula, meadowfoam, rice, poppy, rosehip, apricot, castor oil, caprylic/capric triglyceride;
- the butter is selected from a group comprising cocoa butter, shea butter, illipe butter, kokum butter, murumuru butter, mango butter, cupuacu butter, avocado butter; and the wax is selected from a group comprising lanolin, beeswax, carnauba, candelilla wax and petrolatum.
- the emulsifier is selected from a group comprising glyceryl stearate, glyceryl caprylate, behenyl alcohol, glyceryl behenate, cetearyl glucoside, methyl glucose sequistearate, glyceryl stearate citrate, polyglyceryl-3 stearate, cetearyl olivate, lecithin, stearyl alcohol, sorbitan oleate, polysorbate, stearic acid, cetyl alcohol and cetearyl alcohol, sodium acrylate, sodium acryloyldimethyl taurate copolymer, isohexadecane, polysorbate 80 or mixtures thereof.
- the topical composition according to the present invention in the form of cream containing at least one hexapeptide according to the invention may also be combined with other auxiliary active ingredients that can have synergistic or additional effect to enhance or extend the desired activity described in the invention.
- the auxiliary active ingredient is selected from a group comprising following agents: anti-acne, anti-aging, anti- wrinkle, lightening, whitening, anti-spots, pro-pigmenting, hydrating, moisturizing, humectants, slimming, exfoliating, anti- redness, anti-inflammatory, antioxidants, radical scavengers, anti-glycation, volumizing, restructuring, rejuvenating, regenerating, anti-carbonylation, dermo-relaxing, improving stratum corneum, dermo-epidermal junction, firmness, elasticity, collagen boosters, eye contours (dark circles and under eye bags), promoting blood circulation etc.
- auxiliary active ingredients may be synthetic or obtained from plant, bacteria, fungi, cell cultures or their products.
- the auxiliary active ingredient is selected from a group comprising vitamins A, D, E, K, C, B-group vitamins, coenzyme Q10, allantoin, bisabolol, bakuchiol, resveratrol, lactic acid, amino acids, benzoyl peroxide, sulfur, azelaic acid, peptides preferably acetyl hexapeptide-8, palmitoyl tripeptide- 1, palmitoyl tetrapeptide-7, copper tripeptide- 1, hexapeptide- 1, palmitoyl pentapeptide-4, saccharomyces peptides, and proteins, preferably rice, soy, quinoa or wheat protein; polysaccharides preferably hyaluronic acid or its pharmaceutically and cosmetically acceptable salt or derivative preferably sodium oleoyl hyaluronate, sodium retinoyl hyaluronate, sodium hyaluronate crosspolymer-3; carb
- the preservative is selected from the group comprising aromatic acids and derivatives thereof preferably benzoic acid, sodium benzoate, salicylic acid, dehydroacetic acid, potassium sorbate, parabens; alcohols preferably ethanol, isopropanol, benzyl alcohol, phenoxyethanol, phenethyl alcohol; imidazole derivatives preferably hydantoin, imidazolidinyl urea; cationic surfactants preferably benzalkonium chloride.
- aromatic acids and derivatives thereof preferably benzoic acid, sodium benzoate, salicylic acid, dehydroacetic acid, potassium sorbate, parabens
- alcohols preferably ethanol, isopropanol, benzyl alcohol, phenoxyethanol, phenethyl alcohol
- imidazole derivatives preferably hydantoin, imidazolidinyl urea
- cationic surfactants preferably benzalkonium chloride.
- the concentration of the hexapeptide of the general formula I is in the range of 0.001 to 0.135 % (w/w), preferably 0.001 % to 0.0135 % (w/w).
- composition in the form of serum additionally comprises at least one cosmetic or dermo-pharmaceutical auxiliary ingredient selected from a group comprising thickener, auxiliary active ingredient and preservative as defined above.
- the amount of thickener in the composition according to the present invention is in the range of 0.1 to 20 % (w/w), preferably 0.1 to 5 % (w/w), more preferably 0.2 to 0.5 % (w/w).
- the amount of auxiliary active ingredient in the composition according to the present invention is in the range of 0.001 to 20 % (w/w), preferably 0.001 to 10 % (w/w), more preferably 0.001 to 5 % (w/w).
- the amount of preservative in the composition according to the present invention is in the range of 0.1 to 2.5 % (w/w), preferably 0.1 to 1.5 % (w/w), more preferably 0.8 to 1.2 % (w/w).
- the thickener is selected from a group comprising xantham gum, sclerotium gum, guar gum, cellulose gum, carbomer, hydroxy ethylcellulose, Amorphophallus konjac root extract, karagenan, pullulan, lecithin, lysolecithin, sodium acrylate, sodium acryloyldimethyl taurate copolymer, isohexadecane, polysorbate 80 or mixtures thereof.
- the topical composition according to the present invention containing at least one hexapeptide according to the invention may also be combined with other auxiliary active ingredients that can have synergistic or additional effect to enhance or extend the desired activity described in the invention.
- the auxiliary active ingredient is selected from a group comprising following agents: anti-acne, anti-aging, anti-wrinkle, lightening, whitening, anti- spots, pro-pigmenting, hydrating, moisturizing, humectants, slimming, exfoliating, anti- redness, anti-inflammatory, antioxidants, radical scavengers, anti-glycation, volumizing, restructuring, rejuvenating, regenerating, anti-carbonylation, dermo-relaxing, improving stratum comeum, dermo-epidermal junction, firmness, elasticity, collagen boosters, eye contours (dark circles and under eye bags), promoting blood circulation etc.
- auxiliary active ingredients may be synthetic or obtained from plant, bacteria, fungi, cell cultures or their products.
- the auxiliary active ingredient is selected from a group comprising vitamin C and B-group vitamins; amino acids, peptides preferably acetyl hexapeptide-8, palmitoyl tripeptide- 1, copper tripeptide- 1, Saccharomyces peptides, hexapeptide- 1, and proteins preferably rice protein, soy protein, quinoa or wheat protein; further polysaccharides preferably hyaluronic acid or its pharmaceutically and cosmetically acceptable salt or derivative preferably sodium oleoyl hyaluronate, sodium retinoyl hyaluronate, sodium hyaluronate crosspolymer-3; carboxymethyl glucan, schizophyllan, glucomannan; panthenol; urea; glycerin; plant extracts preferably aloe vera extract, cammomile extract, acai extract, green tea extract, algae extract, oat extract, cannabis extract, cranberry extract; extracts, ferment, ferment
- the preservative is selected from the group comprising aromatic acids and derivatives thereof preferably benzoic acid, sodium benzoate, salicylic acid, dehydroacetic acid; potassium sorbate, parabens; alcohols preferably ethanol, isopropanol, benzyl alcohol, phenoxyethanol, phenethyl alcohol; imidazole derivatives preferably hydantoin, imidazolidinyl urea; cationic surfactants preferably benzalkonium chloride.
- aromatic acids and derivatives thereof preferably benzoic acid, sodium benzoate, salicylic acid, dehydroacetic acid; potassium sorbate, parabens
- alcohols preferably ethanol, isopropanol, benzyl alcohol, phenoxyethanol, phenethyl alcohol
- imidazole derivatives preferably hydantoin, imidazolidinyl urea
- cationic surfactants preferably benzalkonium chloride.
- the amount of water in the composition according to the present invention in the form of cream or serum corresponds to the amount of water added up to 100 % (w/w) of the composition.
- Cosmetically and pharmaceutically acceptable salts of hyaluronic acid are said to be those formed from acids which form non-toxic acid anions selected from a group comprising sodium, potassium, calcium, magnesium, zinc.
- New is the hexapeptide of the general formula I according to the present invention and use thereof or use of the cosmetic or dermo-pharmaceutical topical compositions according to the invention containing said hexapeptide to improve oily and acne-prone skin condition and appearance. More specifically, the hexapeptide according to the invention inhibits epidermal keratinization, reduces sebum production by inhibition of a key enzyme 5 ⁇ -reductase, possesses an anti-inflammatory activity by inhibiting pro-inflammatory interleukins, has an antimicrobial effect towards Cutibacterium acnes, and reduces number of acne lesions in vivo. Furthermore, the said hexapeptide according to the present invention also has an anti-ageing effect by stimulating collagen synthesis and reducing wrinkles in vivo.
- the said hexapeptide of the topical composition according to the invention is dedicated for oily and acne-prone skin as well as for normal skin.
- hexapeptide of the general formula I according to the present invention and the topical composition according to the present invention are dedicated for use for treatment of the skin.
- skin diseases selected from a group comprising acne, atopic dermatitis, psoriasis, peeling skin disease, ichthyosis.
- cosmetic treatment of the skin preferably for cosmetic treatment of the skin.
- Fig. 1 Hexapeptide FWAHKK forms a complex with zinc. Spectrophotometric determination of the ability of zinc to form a complex with FWAHKK hexapeptide using dithizone as a free zinc indicator.
- Fig. 2 Zinc penetrates more effectively into the cells when in Zn-FWAHKK complex.
- HaCaT keratinocytes were incubated with Zn-FWAHKK or ZnSO 4 *7H 2 O (Zn) of corresponding concentration for 3 h. Intracellular zinc was visualized using fluorescence microscopy.
- Fig. 3 Hexapeptide FWAHKK increases cell viability and prevents cytotoxic effect of zinc in Zn-FWAHKK complex.
- NIH-3T3 fibroblasts were incubated with FWAHKK, Zn-FWAHKK or ZnSO4*7H 2 O (Zn) of corresponding concentrations for 48 h.
- Cell viability was determined by MTT assay. * p ⁇ 0.05; ** p ⁇ 0.01; *** p0.001 in comparison to control if not stated otherwise
- Fig. 4 Hexapeptide FWAHKK and ZnSO 4 *7H 2 O reduced 5 ⁇ -reductase gene expression in contrast to retinol. Zn-FWAHKK complex was even more effective than its individual components. HaCaT keratinocytes were treated with FWAHKK, Zn-FWAHKK, ZnSO4*7H 2 O (Zn) and retinol for 72 h. Relative gene expression of 5 ⁇ -reductase (gene SRD5A1) was determined by qRT-PCR. * pO.05; ** p ⁇ 0.01; *** p0.001 in comparison to the respective controls
- Fig. 5 Hexapeptide FWAHKK and Zn-FWAHKK significantly reduced UVB-induced ILIA gene expression in contrast to zinc or retinol.
- HaCaT keratinocytes were irradiated with 10 mJ/cm 2 UVB and treated with FWAHKK, Zn-FWAHKK, ZnSO 4 *7H 2 O (Zn) and retinol for 24 h.
- Relative gene expression of IL-la was determined by qRT-PCR. *** p ⁇ 0.001 in comparison to the respective UVB controls
- Fig. 6 Hexapeptide FWAHKK and Zn-FWAHKK reduced expression of genes associated with keratinocyte differentiation similarly to retinol whereas zinc had no such effect.
- HaCaT keratinocytes were treated with FWAHKK, Zn-FWAHKK, ZnSO 4 *7H 2 O (Zn) and retinol for 72 h.
- Relative gene expression of 5 ⁇ -reductase was determined by qRT-PCR. * p ⁇ 0.05; ** p0.01; *** p0.001 in comparison to the respective controls
- Fig. 7 Hexapeptide FWAHKK and Zn-FWAHKK significantly reduced UVB-induced IL6 and IL8 gene expression in contrast to zinc or retinol.
- HaCaT keratinocytes were irradiated with 10 mJ/cm 2 UVB and treated with FWAHKK, Zn-FWAHKK, ZnSO 4 *7H2O (Zn) and retinol for 24 h.
- Relative gene expression of the pro-inflammatory interleukins IL-6 and IL-8 was determined by qRT-PCR. * p ⁇ 0.05; ** p ⁇ 0.01; *** p0.001 in comparison to the respective UVB controls
- Fig. 8 Hexapeptide FWAHKK and zinc have an antimicrobial activity against C. acnes growing in suspension. Zn-FWAHKK has higher activity than individual compounds. C. acnes growing in suspension was cultivated with FWAHKK, Zn-FWAHKK and ZnSO4*7H 2 O (Zn) for 72 h. OD590 was then measured. * p ⁇ 0.05; ** p0.01; *** p0.001 in comparison to control if not stated otherwise
- Fig. 9 Hexapeptide FWAHKK and Zn-FWAHKK stimulated collagen 1 gene expression in contrast to zinc or retinol.
- HaCaT keratinocytes were treated with FWAHKK, Zn-FWAHKK, ZnSO4*7H 2 O (Zn), and retinol for 72 h.
- Relative gene expression of 5 ⁇ -reductase was determined by qRT-PCR. * pO.05; ** p0.01; *** p0.001 in comparison to the respective controls Fig. 10.
- Zn-FWAHKK complex has anti-acne and anti-ageing activity and is more effective than retinol.
- FWAHKK peptide was synthetized by standard solid phase peptide synthesis using Fmoc/tBu strategy on Wang resin (Amblard et al. 2006).
- the FWAHKK peptide was synthetized at 0.1 mmol scale using the CEM Liberty Blue automated micro wave peptide synthesizer (CEM, USA) on Wang resin preloaded with the first Fmoc-AA.
- Fmoc deprotections were performed with 20% piperidine in DMF.
- Coupling reactions were performed using 5 equivalents of Fmoc-AA/DIC/Oxyma Pure® in DMF.
- V-terminus of the synthetized peptide FWAHKK on the resin was acetylated or palmitoylated using 2 meq of acetic or palmitic anhydride/pyridine (1/1, v/v) in DMF for 30 min at room temperature.
- FWAHKK peptide The ability of FWAHKK peptide to form a complex with zinc was evaluated as described previously with slight modifications (Catapano etal. 2018). Briefly, 20 ⁇ L of solution of FWAHKK (0-600 ⁇ M (0-490 ⁇ g/mL; 0-0.049 w/w %), prepared as described in Example 1) and 60 ⁇ M (17.3 ⁇ g/mL; 0.00173 %) ZnSO 4 *7H 2 O in 15 mM HEPES, pH 6.8 was mixed with 20 ⁇ L of 250 ⁇ M dithizone in DMSO and 80 ⁇ L of 15 mM HEPES, pH 6.8. Dithizone was used as an indicator of free zinc. After 30 min incubation at room temperature (RT), the absorbance was measured at 520 nm and percentage of zinc in complex with FWAHKK peptide was calculated.
- RT room temperature
- Fig. 1 confirmed the ability of peptide FWAHKK to form a complex with zinc.
- Zn-FWAHKK prepared as described in Example 1 in which the molar ratio of FWAHKK and zinc is 1 : 1 , approx. 50 % of zinc is in the complex with the hexapeptide.
- HaCaT keratinocytes (CLS collection, Germany) were cultured in Dulbecco’s modified Eagle’s medium (DMEM) supplemented with 10 % fetal bovine serum, 0.3 mg/mL glutamine, lOO U/mL penicillin and 0.1 mg/mL streptomycin (all Sigma- Aldrich, USA) at 37 °C, in a humidified atmosphere with 5 % CO2.
- DMEM Dulbecco’s modified Eagle’s medium
- the cells seeded in appropriate density into 96- well plates were treated with 1352 ⁇ g/mL (0.1352 %) Zn-FWAHKK complex (prepared as described in Example 1) or ZnSO 4 *7H 2 O of corresponding concentration (352 ⁇ g/mL (0.0352 %)) for 3 h. Then, the cells were washed by the cell culture medium and incubated with 1 ⁇ M FluoZinTM-3 AM (Invitrogen, USA), a cell-permeant, Anorogenic Zn 2+ -selective indicator, and 20 ⁇ M Hoechst (Abeam, UK), a fluorescent DNA stain in the cell culture medium for 30 min at 37 °C in the dark. Then, the cells were washed in phosphate-buffered saline (PBS). The fluorescence was observed using an Eclipse 50i fluorescence microscope equipped with a DS-Fil camera (both Nikon, Japan).
- NIH-3T3 mouse embryonic fibroblasts (ATCC collection, USA) were cultured in the same manner as HaCaT keratinocytes as described in Example 3.
- the cells seeded in appropriate density into 96-well plates were treated with FWAHKK (2.5 - 80 ⁇ g/mL (0.00025 - 0.008 %)), Zn-FWAHKK (3.4 - 108 ⁇ g/mL (0.00034 - 0.0108 %)) (both prepared as described in Example 1) and ZnSO 4 *7H 2 O (0.9 - 28.2 ⁇ g/mL (0.00009 - 0.00282 %)) for 48 h. Then, cell viability was determined by MTT assay (Riss et al. 2016).
- MTT 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide
- cell lysis and solubilization of formazan was carried out by incubation of the cells with a solubilizing solution (45 % isopropanol, 45 % DMSO, 10 % Triton-X, 0.3 M HC1) for 30 min at RT, shaking.
- the absorbance was then measured at 570 run by a spectrophotometer (EnVision® 2105 Multimode Plate Reader, PerkinElmer, USA). T-test was used for the statistical evaluation of the results.
- HaCaT keratinocytes (CLS collection, Germany) were cultured as described in Example 3.
- the cells seeded in appropriate density into 6-well plates were treated with FWAHKK (1 ⁇ g/mL (0.0001 %) and 10 ⁇ g/mL (0.001 %)), Zn-FWAHKK (1.35 ⁇ g/mL (0.000135 %) and 13.5 ⁇ g/mL (0.00135 %)) (both prepared as described in Example 1), ZnSO 4 *7H 2 O (Zn, 0.35 ⁇ g/mL (0.000035 %) and 3.5 ⁇ g/mL (0.00035 %)), and 10 ⁇ M retinol (in DMSO, final concentration of DMSO was 0.1 %) for 72 h. Control cells were untreated or treated with 0.1 % DMSO in the case of retinol control.
- 5 ⁇ -reductase gene expression was determined by quantitative, real-time, reverse-transcription PCR (qRT-PCR) as follows.
- the total RNA was isolated from the cells by the acid guanidine thiocyanate-phenol extraction method using TRI Reagent (Sigma Aldrich, USA) according to the instructions provided by the supplier.
- Reverse transcription was performed using High capacity cDNA reverse transcription kit (Thermo Fisher Scientific, MA, USA) in GenePro thermal cycler (Bioer Technology, China) according to the manufacturer’s instructions.
- 5 ⁇ -reductase is a key enzyme involved in the androgens-induced sebum production.
- the enzyme converts testosterone, the most common androgen, into DHT which is several times more potent in stimulation of sebum production.
- the results (Fig. 4) showed that the hexapeptide FWAHKK, Zn-FWAHKK as well as ZnSO4*7H2O significantly reduced gene expression of 5 ⁇ -reductase (gene SRD5AP).
- the complex Zn-FWAHKK was more effective than its individual components of corresponding concentrations.
- retinol did not have any significant effect on 5 ⁇ -reductase gene expression.
- HaCaT keratinocytes (CLS collection, Germany) were cultured as described in Example 3.
- ILIA gene expression was determined by real-time qRT-PCR as described in Example 5 using specific TaqMan gene expression assays for ILIA (qHsaCIP0030471, BioRad, CA, USA), and RPL13A (Hs04194366_gl, Thermo Fisher Scientific, MA, USA) as a reference gene. The data were analyzed using the 2' ⁇ Ct method. The data were normalized to the UVB untreated controls or in the case of retinol to UVB DMSO controls. T-test was used for the statistical evaluation of the results.
- IL-1 ⁇ is a pro-inflammatory interleukin stimulating hyperkeratinization of follicular keratinocytes (Guy and Kealey 1998) in the early phases of acne pathogenesis.
- HaCaT keratinocytes (CLS collection, Germany) were cultured as described in Example 3.
- the cells seeded in appropriate density into 6-well plates were treated with FWAHKK (1 ⁇ g/mL (0.0001 %) and 10 ⁇ g/mL (0.001 %), Zn-FWAHKK (1.35 ⁇ g/mL (0.000135 %) and 13.5 ⁇ g/mL (0.00135 %)) (both prepared as described in Example 1), ZnSO 4 *7H 2 O (Zn; 0.35 ⁇ g/mL (0.000035 %) and 3.5 ⁇ g/mL (0.00035 %)) and 10 ⁇ M retinol (in DMSO, final concentration of DMSO was 0.1 %) for 72 h. Control cells were untreated or treated with 0.1 % DMSO in the case of retinol control.
- Expression of the selected genes involved in keratinocyte differentiation was determined by real-time qRT-PCR as described in Example 5 using specific TaqMan gene expression assays for FLG (Hs00856927_gl), OCLN (Hs00170162_ml), LCE2C (Hs02390636_sl), SPRR2E (qHsaCEP0055677, BioRad, CA, USA), KRT10 (Hs01043114_gl) and RPL13A (Hs04194366_gl) as a reference gene (all except SPRR2E Thermo Fisher Scientific, MA, USA).
- the data were analyzed using the 2' ⁇ Ct method. The data were normalized to the untreated controls or in the case of retinol to DMSO controls. T-test was used for the statistical evaluation of the results.
- hexapeptide FWAHKK as well as Zn-FWAHKK were shown to downregulate genes associated with keratinocyte differentiation in the same manner as 10 ⁇ M retinol whereas zinc of corresponding concentrations had no such effect (Fig. 6).
- HaCaT keratinocytes (CLS collection, Germany) were cultured as described in Example 3.
- IL1A gene expression was determined by real-time qRT-PCR as described in Example 5 using specific TaqMan gene expression assays for IL6 (Hs00174131 ml), IL8 (Hs00174103_ml), and RPL13A (Hs04194366_gl) as a reference gene (all Thermo Fisher Scientific, MA, USA). The data were analyzed using the 2 - ⁇ Ct method. The data were normalized to the UVB untreated controls or in the case of retinol to UVB DMSO controls. T- test was used for the statistical evaluation of the results.
- Inflammation is a key event in acne pathogenesis.
- We induced inflammatory processes such as the overexpression of the pro-inflammatory interleukins IL-6 and IL-8 in HaCaT keratinocytes using UVB irradiation (Fig. 7).
- Cutibacterium acnes (strain DSM 1897, DSZM collection, Germany) was maintained in suspension in tryptic soy broth (TSB) at 37 °C. The bacteria were then inoculated in appropriate density into TSB containing FWAHKK (10 - 80 ⁇ g/mL (0.001 - 0.008 %)), Zn- FWAHKK (13.5 - 108.2 ⁇ g/mL (0.00135 - 0.01082 %)) (both prepared as described in Example 1) and ZnSO4*7H2O (Zn; 3.5 - 28.2 ⁇ g/mL (0.00035 - 0.00282 %)) in 96-well plates.
- FWAHKK 10 - 80 ⁇ g/mL (0.001 - 0.008 %)
- Zn- FWAHKK (13.5 - 108.2 ⁇ g/mL (0.00135 - 0.01082 %)
- ZnSO4*7H2O Zn; 3.5 - 28.
- the bacteria were cultivated for 72 h at 37 °C and then, optical density was measured at 590 nm (OD590) by a spectrophotometer (EnVision® 2105 Multimode Plate Reader, PerkinElmer, USA). T-test was used for the statistical evaluation of the results.
- NIH-3T3 mouse embryonic fibroblasts (ATCC collection, USA) were cultured in the same manner as HaCaT keratinocytes as described in Example 3.
- the cells seeded in appropriate density into 6-well plates were treated with FWAHKK (1 ⁇ g/mL (0.0001 %) and 10 ⁇ g/mL (0.001 %)), Zn-FWAHKK (1.35 ⁇ g/mL (0.000135 %) and 13.5 ⁇ g/mL (0.00135 %)) (both prepared as described in Example 1), ZnSO4*7H2O (Zn, 0.35 ⁇ g/mL (0.000035 %) and 3.5 ⁇ g/mL (0.00035 %)), and 10 ⁇ M retinol (in DMSO, final concentration of DMSO was 0.1 %) for 72 h. Control cells were untreated or treated with 0.1 % DMSO in the case of retinol control.
- COL1A1 gene expression was determined by real-time qRT-PCR as described in Example 5 using specific TaqMan gene expression assays for COL1A1 (Mm00801666_gl), and RPL13A (Mm05910660_gl) as a reference gene (both Thermo Fisher Scientific, MA, USA). The data were analyzed using the 2 - ⁇ Ct method. The data were normalized to the untreated controls or in the case of retinol to DMSO controls. T-test was used for the statistical evaluation of the results.
- Example 11 Zn-FWAHKK improves appearance of acne-prone skin and also has an anti- ageing effect in vivo
- the measurements were performed after 30 min of acclimation of the volunteers in a room with controlled conditions (T: 20-22 °C; RH 40-45 %).
- the number of acne lesions was determined by an image analysis of the whole-face images obtained by VisiaCR high-resolution camera (Canfield Scientific, USA). The quantification was performed using an Image-Pro 10 analysis software (Media Cybernetics, USA). Crow's feet wrinkle depth was determined by a Primos Lite 3D camera (Canfield Scientific, USA). The results showed an improvement of the appearance of the acne-prone skin represented by the reduced number of acne lesions (Fig. 10A). Zn-FWAHKK was also shown to possess an anti-ageing activity by reducing wrinkles (Fig 10B). In both cases, Zn-FWAHKK was more effective than 0.2 % retinol. Table 1. Compositions of the emulsions used in the in vivo study
- Example 12 Compositions of the emulsions with FWAHKK, Zn-FWAHKK, acetyl- FWAHKK, or palmitoyl-FWAHKK
- Oil and water phases were prepared and heated to 70 °C. Next, both phases were mixed and emulsified while stirring (290 rpm/min). Then, the emulsion was cooled to 40 °C and the water-soluble ingredient phase and/or oil-soluble active ingredient phase and/or vitamin E and preservative were added. Finally, pH was measured and adjusted to values between 5.2 and 6.5 with 1-50% citric acid or 1-50 % KOH or NaOH.
- Example 13 Compositions of the serums with FWAHKK, Zn-FWAHKK and acetyl- FWAHKK
- hexapeptide FWAHKK or Zn-FWAHKK or acetyl-FWAHKK and active ingredients except sodium hyaluronate and Crosslinked 114 were added to water and stirred till complete dissolution.
- thickeners and/or sodium hyaluronate and Crosslinked 114 were added and mixed till complete dissolution. Then, a preservative was added.
- pH was measured and adjusted to values between 5.2 and 6.5 with 1-50% citric acid or 1-50 % KOH or NaOH.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biotechnology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Cosmetics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZPV2022-141 | 2022-03-31 | ||
| CZ2022-141A CZ309857B6 (cs) | 2022-03-31 | 2022-03-31 | Hexapeptid, kompozice zahrnující tento hexapeptid a jejich topické použití |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2023186193A1 true WO2023186193A1 (en) | 2023-10-05 |
Family
ID=86095817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CZ2023/050016 WO2023186193A1 (en) | 2022-03-31 | 2023-03-31 | Hexapeptide, composition comprising thereof and topical use thereof |
Country Status (2)
| Country | Link |
|---|---|
| CZ (1) | CZ309857B6 (cs) |
| WO (1) | WO2023186193A1 (cs) |
Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0526192A2 (en) * | 1991-07-30 | 1993-02-03 | TSUMURA & CO. | Hexapeptide |
| DE4127790A1 (de) * | 1991-08-22 | 1993-02-25 | Wank Anna | Verwendung von oligopeptiden mit 2 bis 5 peptidbindungen fuer kosmetische zwecke und einige neue oligopeptid-metallkomplexe |
| WO2003015809A2 (en) | 2001-08-21 | 2003-02-27 | Micrologix Biotech Inc. | Antimicrobial cationic peptides and formulations thereof |
| WO2005025598A1 (ja) | 2003-09-16 | 2005-03-24 | Astellas Pharma Inc. | Ｐｒｏｐｉｏｎｉｂａｃｔｅｒｉｕｍ ａｃｎｅｓに対する抗菌剤 |
| WO2006086321A2 (en) * | 2005-02-09 | 2006-08-17 | Helix Biomedix Inc. | Antimicrobial hexapeptides |
| WO2010091893A1 (en) * | 2009-02-16 | 2010-08-19 | Lipotec, S.A. | Peptides used in the treatment and/or care of the skin, mucous membranes and/or scalp and their use in cosmetic or pharmaceutical compositions |
| WO2016154020A1 (en) * | 2015-03-20 | 2016-09-29 | The Regents Of The University Of California | Methods for reducing sebum production and/or excretion |
| CN107698662A (zh) | 2017-10-24 | 2018-02-16 | 银川利智信知识产权咨询服务有限公司 | 治疗痤疮的肽组合 |
| WO2018102508A1 (en) * | 2016-11-30 | 2018-06-07 | Lubrizol Advanced Materials, Inc. | Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes |
| CN111253469A (zh) | 2020-03-06 | 2020-06-09 | 暨南大学 | 一种自组装短肽及其在治疗痤疮方面的应用 |
| KR20200101767A (ko) | 2019-02-20 | 2020-08-28 | 바이오센서연구소 주식회사 | 피부 항균 활성을 갖는 펩타이드 및 그를 포함하는 피부 항균 조성물 |
| CN112979762A (zh) | 2021-04-26 | 2021-06-18 | 中国医学科学院皮肤病医院(中国医学科学院皮肤病研究所) | 环肽piz及其用途 |
| KR102266613B1 (ko) * | 2020-09-21 | 2021-06-18 | 자안바이오 주식회사 | 항염증 활성을 갖는 신규한 펩티드 및 이의 용도 |
| WO2021175186A1 (zh) | 2020-03-06 | 2021-09-10 | 暨南大学 | 小分子短肽在制备治疗痤疮的产品中的应用 |
| WO2021204309A1 (en) * | 2020-04-09 | 2021-10-14 | Contipro A.S. | Casein-derived pentapeptide and composition comprising thereof and topical use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2541177B1 (es) * | 2014-01-15 | 2016-06-06 | Sani-Red, S.L. | Formulación cosmética de uso tópico con capacidad de regeneración dérmica, epidérmica y antiarrugas |
| JP7100390B2 (ja) * | 2017-09-18 | 2022-07-13 | エニジェン カンパニー．，リミテッド． | 活性物質－ヘキサペプチド複合体、及びこれを含む化粧料組成物 |
| CN110882179A (zh) * | 2019-12-24 | 2020-03-17 | 河南怀雪生物科技有限公司 | 一种六胜钛安瓶精华液及其制备方法 |
| CN113520896A (zh) * | 2021-08-01 | 2021-10-22 | 青海瑞肽生物科技有限公司 | 一种具有祛痘和修复痘印功能的组合物及制备方法 |
-
2022
- 2022-03-31 CZ CZ2022-141A patent/CZ309857B6/cs unknown
-
2023
- 2023-03-31 WO PCT/CZ2023/050016 patent/WO2023186193A1/en active Application Filing
Patent Citations (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0526192A2 (en) * | 1991-07-30 | 1993-02-03 | TSUMURA & CO. | Hexapeptide |
| DE4127790A1 (de) * | 1991-08-22 | 1993-02-25 | Wank Anna | Verwendung von oligopeptiden mit 2 bis 5 peptidbindungen fuer kosmetische zwecke und einige neue oligopeptid-metallkomplexe |
| WO2003015809A2 (en) | 2001-08-21 | 2003-02-27 | Micrologix Biotech Inc. | Antimicrobial cationic peptides and formulations thereof |
| WO2005025598A1 (ja) | 2003-09-16 | 2005-03-24 | Astellas Pharma Inc. | Ｐｒｏｐｉｏｎｉｂａｃｔｅｒｉｕｍ ａｃｎｅｓに対する抗菌剤 |
| WO2006086321A2 (en) * | 2005-02-09 | 2006-08-17 | Helix Biomedix Inc. | Antimicrobial hexapeptides |
| EP1853620A2 (en) | 2005-02-09 | 2007-11-14 | Helix Biomedix, INc. | Antimicrobial hexapeptides |
| WO2010091893A1 (en) * | 2009-02-16 | 2010-08-19 | Lipotec, S.A. | Peptides used in the treatment and/or care of the skin, mucous membranes and/or scalp and their use in cosmetic or pharmaceutical compositions |
| WO2016154020A1 (en) * | 2015-03-20 | 2016-09-29 | The Regents Of The University Of California | Methods for reducing sebum production and/or excretion |
| WO2018102508A1 (en) * | 2016-11-30 | 2018-06-07 | Lubrizol Advanced Materials, Inc. | Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes |
| CN107698662A (zh) | 2017-10-24 | 2018-02-16 | 银川利智信知识产权咨询服务有限公司 | 治疗痤疮的肽组合 |
| KR20200101767A (ko) | 2019-02-20 | 2020-08-28 | 바이오센서연구소 주식회사 | 피부 항균 활성을 갖는 펩타이드 및 그를 포함하는 피부 항균 조성물 |
| CN111253469A (zh) | 2020-03-06 | 2020-06-09 | 暨南大学 | 一种自组装短肽及其在治疗痤疮方面的应用 |
| WO2021175186A1 (zh) | 2020-03-06 | 2021-09-10 | 暨南大学 | 小分子短肽在制备治疗痤疮的产品中的应用 |
| WO2021204309A1 (en) * | 2020-04-09 | 2021-10-14 | Contipro A.S. | Casein-derived pentapeptide and composition comprising thereof and topical use thereof |
| KR102266613B1 (ko) * | 2020-09-21 | 2021-06-18 | 자안바이오 주식회사 | 항염증 활성을 갖는 신규한 펩티드 및 이의 용도 |
| CN112979762A (zh) | 2021-04-26 | 2021-06-18 | 中国医学科学院皮肤病医院(中国医学科学院皮肤病研究所) | 环肽piz及其用途 |
Non-Patent Citations (40)
| Title |
|---|
| ABENDROT, M.U. KALINOWSKA-LIS: "Zinc-Containing Compounds for Personal Care Applications", INTERNATIONAL JOURNAL OF COSMETIC SCIENCE, vol. 40, no. 4, 2018, pages 319 - 27 |
| AMBLARD, MURIEL, JEAN-ALAIN FEHRENTZ, JEAN MARTINEZ, GILLES SUBRA: "Methods and Protocols of Modern Solid Phase Peptide Synthesis", MOLECULAR BIOTECHNOLOGY, vol. 33, no. 3, 2006, pages 239 - 54, XP009116689, Retrieved from the Internet <URL:https://doi.org/10.1385/MB:33:3:239> DOI: 10.1385/MB:33:3:239 |
| ANDERSON, K. M.S. LIAO.: "Selective Retention of Dihydrotestosterone by Prostatic Nuclei", NATURE, vol. 219, no. 5151, 1968, pages 277 - 79, XP037042399, Retrieved from the Internet <URL:https://doi.org/10.1038/219277a0.> DOI: 10.1038/219277a0 |
| ARIF TASLEEM: "Salicylic Acid as a Peeling Agent: A Comprehensive Review.", COSMETIC AND INVESTIGATIONAL DERMATOLOGY, 2015, pages 455 - 61, Retrieved from the Internet <URL:https://doi.org/10.2147/CCID.S84765> |
| BOWE, WHITNEY P., JENNIFER C. FILIP, JOSEPH M. DIRIENZO, ALLA VOLGINA, DAVID J. MARGOLIS: "Inhibition of Propionibacterium Acnes by Bacteriocin-like Inhibitory Substances (BLIS) Produced by Streptococcus Salivarius.", JOURNAL OF DRUGS IN DERMATOLOGY: JDD, vol. 5, no. 9, 2006, pages 868 - 70 |
| CATAPANO, MARIA CARMEN, VACLAV TVRDY, JANA KARLICKOVA, LAURA MERCOLINI, PREMYSL MLADENKA: "A Simple, Cheap but Reliable Method for Evaluation of Zinc Chelating Properties", BIOORGANIC CHEMISTRY, vol. 77, 2018, pages 287 - 92, Retrieved from the Internet <URL:https://doi.org/10.1016/j.bioorg.2018.01.015> |
| CEBRIAN, RUBEN, SERGIO AREVALO, SUSANA RUBINO, SALVADOR ARIAS-SANTIAGO, MARIA DOLORES ROJO, MANUEL MONTALBAN-LOPEZ, MANUEL MARTINE: "Control of Propionibacterium Acnes by Natural Antimicrobial Substances: Role of the Bacteriocin AS-48 and Lysozyme.", SCIENTIFIC REPORTS, vol. 8, no. 1, 2018, pages 11766, Retrieved from the Internet <URL:https://doi.org/10.1038/s41598-018-29580-7> |
| CUNHA, MARISA GONZAGA DA, FERNANDO LUIZ AFFONSO FONSECA, CARLOS D. APARECIDA S. MACHADO: "Androgenic Hormone Profile of Adult Women with Acne", DERMATOLOGY (BASEL, SWITZERLAND), vol. 226, no. 2, 2013, pages 167 - 71, Retrieved from the Internet <URL:https://doi.org/10.1159/000347196.> |
| DOWNING, D. T.M. E. STEWARTP. W. WERTZJ. S. STRAUSS.: "Essential Fatty Acids and Acne", JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY, vol. 14, 1986, pages 221 - 25, XP025596795, Retrieved from the Internet <URL:https://doi.org/10.1016/s0190-9622(86)70025-x> DOI: 10.1016/S0190-9622(86)70025-X |
| DRENO, B., S. PECASTAINGS, S. CORVEC, S. VERALDI, A. KHAMMARI, C. ROQUES: "Cutibacterium Acnes (Propionibacterium Acnes) and Acne Vulgaris: A Brief Look at the Latest Updates", JOURNAL OF THE EUROPEAN ACADEMY OF DERMATOLOGY AND VENEREOLOGY, 2018 |
| FRITSCH, M.C. E. ORFANOSC. C. ZOUBOULIS: "Sebocytes Are the Key Regulators of Androgen Homeostasis in Human Skin", THE JOURNAL OF INVESTIGATIVE DERMATOLOGY, vol. 116, no. 5, 2001, pages 793 - 800, Retrieved from the Internet <URL:https://doi.org/10.1046/).1523-1747.2001.01312.x> |
| GUY, R.T. KEALEY: "The Effects of Inflammatory Cytokines on the Isolated Human Sebaceous Infundibulum", THE JOURNAL OF INVESTIGATIVE DERMATOLOGY, vol. 110, no. 4, 1998, pages 410 - 15, Retrieved from the Internet <URL:https://doi.org/10.1046/j.1523-1747.1998.00143.x> |
| HAN, RUIHANS-MATTI BLENCKEHAO CHENGCHUN LI: "The Antimicrobial Effect of CEN1HC-Br against Propionibacterium Acnes and Its Therapeutic and Anti-Inflammatory Effects on Acne Vulgaris", PEPTIDES, vol. 99, 2018, pages 36 - 43, XP085325567, DOI: 10.1016/j.peptides.2017.11.001 |
| JONETTE E. KERI: "The Role of Zinc in the Treatment of Acne: A Review of the Literature", DERMATOLOGIC THERAPY, vol. 31, no. 1, 2018, Retrieved from the Internet <URL:https://doi.org/10.1111/dth.12576> |
| KANG, BONG SEONJAE-GU SEOGWA-SU LEEJUNG-HWA KIMSEI YEON KIMYE WON HANHOON KANG ET AL.: "Antimicrobial Activity of Enterocins from Enterococcus Faecalis SL-5 against Propionibacterium Acnes, the Causative Agent in Acne Vulgaris, and Its Therapeutic Effect", JOURNAL OF MICROBIOLOGY (SEOUL, KOREA, vol. 47, no. 1, 2009, pages 101 - 9, XP008118833, Retrieved from the Internet <URL:https://doi.org/10.1007/s12275-008-0179-y> DOI: 10.1007/s12275-008-0179-y |
| KUMTORNRUT, CHANAT, TAKESHI YAMAUCHI, SAAYA KOIKE, SETSUYA AIBA, KENSHI YAMASAKI.: "Androgens Modulate Keratinocyte Differentiation Indirectly through Enhancing Growth Factor Production from Dermal Fibroblasts", JOURNAL OF DERMATOLOGICAL SCIENCE, vol. 93, no. 3, 2019, pages 150 - 58, Retrieved from the Internet <URL:https://doi.org/10.1016/j.jdermsci.2019.01.007> |
| LIM, HEE-SUN, SEUNG-MIN CHUN, MIN-GYU SOUNG, JENNY KIM, SEONG-JIN KIM: "Antimicrobial Efficacy of Granulysin-Derived Synthetic Peptides in Acne Vulgaris", INTERNATIONAL JOURNAL OF DERMATOLOGY, vol. 54, no. 7, 2015, pages 853 - 62, Retrieved from the Internet <URL:https://doi.org/10.1111/ijd.12756> |
| LIU, HAIBO, HAIYAN YU, JUN XIA, LING LIU, GUAN J. LIU, HONG SANG, FRANK PEINEMANN: "Topical Azelaic Acid, Salicylic Acid, Nicotinamide, Sulphur, Zinc and Fruit Acid (Alpha-Hydroxy Acid) for Acne", THE COCHRANE DATABASE OF SYSTEMATIC REVIEWS, vol. 5, 2020, Retrieved from the Internet <URL:https://doi.org/10.1002/14651858.CD011368.pub2> |
| MA, ZIYUAN, NIKOLAY KOCHERGIN, OLGA OLISOVA, ELENA SNARSKAYA, DERMATOLOGY, 2021, Retrieved from the Internet <URL:https://doi.org/10.1111/jocd.14300.> |
| MCINTURFF, JAMIE E.ROBERT L. MODLINJENNY KIM: "The Role of Toll-like Receptors in the Pathogenesis and Treatment of Dermatological Disease", JOURNAL OF INVESTIGATIVE, vol. 125, no. 1, 2005, pages 1 - 8, Retrieved from the Internet <URL:https://doi.org/10.1111/j.0022-202X.2004.23459.x> |
| MELO, MANUEL N.DOMINIQUE DUGOURDMIGUEL A. R. B. CASTANHO: "Omiganan Pentahydrochloride in the Front Line of Clinical Applications of Antimicrobial Peptides", RECENT PATENTS ON ANTI-INFECTIVE DRUG DISCOVERY, vol. 1, no. 2, 2006, pages 201 - 7, Retrieved from the Internet <URL:https://doi.org/l0.2174/157489106777452638> |
| MIAZGA-KARSKA, MALGORZATAKATARZYNA MICHALAKGRAZYNA GINALSKA: "Anti-Acne Action of Peptides Isolated from Burdock Root-Preliminary Studies and Pilot Testing", MOLECULES (BASEL, SWITZERLAND), vol. 25, no. 9, 2020, Retrieved from the Internet <URL:https://doi.org/10.3390/molecules25092027> |
| MILLS, OTTO H., MARESSA C. CRISCITO, TODD E. SCHLESINGER, ROBERT VERDICCHIO, ERNEST SZOKE: "Addressing Free Radical Oxidation in Acne Vulgaris", THE JOURNAL OF CLINICAL AND AESTHETIC DERMATOLOGY, vol. 9, no. 1, 2016, pages 25 - 30 |
| NAIR, SITHARA S.OLGA Y. ZOLOTARSKAYAMATTHEW J. BECKWITHDENNIS E. OHMANKENNETH J. WYNNE: "A Polycation Antimicrobial Peptide Mimic without Resistance Buildup against Propionibacterium Acnes", MACROMOLECULAR BIOSCIENCE, vol. 17, no. 9, 2017, Retrieved from the Internet <URL:https://doi.org/l0.1002/mabi.201700090> |
| PAN, CHIEH-YUJYH-YIH CHENTAI-LANG LINCHENG-HUI LIN: "In Vitro Activities of Three Synthetic Peptides Derived from Epinecidin-1 and an Anti-Lipopolysaccharide Factor against Propionibacterium Acnes, Candida Albicans, and Trichomonas Vaginalis", PEPTIDES, vol. 30, no. 6, 2009, pages 1058 - 68, XP026127091, Retrieved from the Internet <URL:https://doi.Org/10.1016/j.peptides.2009.02.006.> DOI: 10.1016/j.peptides.2009.02.006 |
| PANCHAUD, ALICECHANTAL CSAJKAPAUL MERLOBCHRISTOF SCHAEFERMAYA BERLINMARCO DE SANTISTHIERRY VIAL ET AL.: "Pregnancy Outcome Following Exposure to Topical Retinoids: A Multicenter Prospective Study", THE JOURNAL OF CLINICAL PHARMACOLOGY, vol. 52, no. 12, 2012, pages 1844 - 51, Retrieved from the Internet <URL:https://doi.org/10.1177/0091270011429566> |
| POPOVIC, SUZANAEDIT URBANMIODRAG LUKICJ. MICHAEL CONLON: "Peptides with Antimicrobial and Anti-Inflammatory Activities That Have Therapeutic Potential for Treatment of Acne Vulgaris", PEPTIDES, vol. 34, no. 2, 2012, pages 275 - 82, XP055255645, Retrieved from the Internet <URL:https://doi.Org/10.1016/j.peptides.2012.02.010.> DOI: 10.1016/j.peptides.2012.02.010 |
| RUBINCHIK, EVELINADOMINIQUE DUGOURDTERESA ALGARACHRISTOPHER PASETKAH. DAVID FRIEDLAND: "Antimicrobial and Antifungal Activities of a Novel Cationic Antimicrobial Peptide, Omiganan, in Experimental Skin Colonisation Models", INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, vol. 34, no. 5, 2009, pages 457 - 61, XP026601928, Retrieved from the Internet <URL:https://doi.org/10.1016/j.ijantimicag.2009.05.003> DOI: 10.1016/j.ijantimicag.2009.05.003 |
| RYU, S.Y. PARKB. KIMS.-M. CHOJ. LEEH.-H. LEEC. GURLEY ET AL.: "Inhibitory and Anti-Inflammatory Effects of the Helicobacter Pylori-Derived Antimicrobial Peptide HPA3NT3 against Propionibacterium Acnes in the Skin", THE BRITISH JOURNAL OF DERMATOLOGY, vol. 171, no. 6, 2014, pages 1358 - 67, Retrieved from the Internet <URL:https://doi.org/10.1111/bjd.13480.> |
| RYU, SUNHYO, HYO MI HAN, PETER I. SONG, CHERYL A. ARMSTRONG, YOONKYUNG PARK: "Suppression of Propionibacterium Acnes Infection and the Associated Inflammatory Response by the Antimicrobial Peptide P5 in Mice", PLOS ONE, vol. 10, no. 7, 2015, pages e0132619 |
| TANGHETTI, EMIL A.: "The Role of Inflammation in the Pathology of Acne", THE JOURNAL OF CLINICAL AND AESTHETIC DERMATOLOGY, vol. 6, no. 9, 2013, pages 27 - 35, XP055891103 |
| THIBOUTOT, D. M.: "The Role of Follicular Hyperkeratinization in Acne", JOURNAL OF DERMATOLOGICAL TREATMENT, vol. 11, 2000, pages 5 - 8, Retrieved from the Internet <URL:https://doi.org/10.1080/095466300750163645> |
| THIELITZ, ANJAHARALD GOLLNICK: "Topical Retinoids in Acne Vulgaris: Update on Efficacy and Safety", AMERICAN JOURNAL OF CLINICAL DERMATOLOGY, vol. 9, no. 6, 2008, pages 369 - 81, XP009523184, Retrieved from the Internet <URL:https://doi.org/10.2165/0128071-200809060-00003> DOI: 10.2165/0128071-200809060-00003 |
| WALSH, TIMOTHY R., JOHN EFTHIMIOU, BRIGITTE DRENO: "Systematic Review of Antibiotic Resistance in Acne: An Increasing Topical and Oral Threat.", INFECTIOUS DISEASES, vol. 16, no. 3, 2016, pages e23 - 33, XP029431752, Retrieved from the Internet <URL:https://doi.org/10.1016/51473-3099(15)00527-7> DOI: 10.1016/S1473-3099(15)00527-7 |
| WOODBURNKATHRYN W.JESSE JAYNESL. EDWARD CLEMENS: "Designed Antimicrobial Peptides for Topical Treatment of Antibiotic Resistant Acne Vulgaris", ANTIBIOTICS, vol. 9, no. 1, 2020, pages 23, Retrieved from the Internet <URL:https://doi.org/10.3390/antibiotics9010023> |
| WU, YUNGUANGXIAN ZHANGMAOJUN ZHOU: "Inhibitory and Anti-Inflammatory Effects of Two Antimicrobial Peptides Moronecidin and Temporin-lDra against Propionibacterium Acnes in Vitro and in Vivo", JOURNAL OF PEPTIDE SCIENCE: AN OFFICIAL PUBLICATION OF THE EUROPEAN PEPTIDE SOCIETY, vol. 26, no. 7, 2020, pages e3255, Retrieved from the Internet <URL:https://doi.org/10.1002/psc.3255> |
| WU, YUNYUANYUAN QIANGKUN CAOWEI ZHANGGUANGXIAN ZHANG: "Inhibitory Effect of the Antimicrobial Peptide BLP-7 against Propionibacterium Acnes and Its Anti-Inflammatory Effect on Acne Vulgaris", TOXICON: OFFICIAL JOURNAL OF THE INTERNATIONAL SOCIETY ON TOXINOLOGY, vol. 184, 2020, pages 109 - 15, XP086234043, Retrieved from the Internet <URL:https://doi.org/10.1016/j.toxicon.2020.06.006> DOI: 10.1016/j.toxicon.2020.06.006 |
| YEE, BRITTANY E.PHILLIP RICHARDSJENNIFER Y. SUIAMANDA FLEMING MARSCH: "Serum Zinc Levels and Efficacy of Zinc Treatment in Acne Vulgaris: A Systematic Review and Meta-Analysis", DERMATOLOGIC THERAPY, vol. 33, no. 6, 2020, pages e14252, Retrieved from the Internet <URL:https://doi.org/l0.1111/dth.14252> |
| YENTZER, BRAD A.JEFF HICKERIN L. REESEADAM UHASSTEVEN R. FELDMANRAJESH BALKRISHNAN: "Acne Vulgaris in the United States: A Descriptive Epidemiology", CUTIS, vol. 86, no. 2, 2010, pages 94 - 99 |
| ZHANG, ZHIYELIXIAN MUJING TANGZILEI DUANFENGYU WANGLIN WEIMINGQIANG RONGREN LAI: "A Small Peptide with Therapeutic Potential for Inflammatory Acne Vulgaris", PIOS ONE, vol. 8, no. 8, 2013, pages e72923, XP055434360, Retrieved from the Internet <URL:https://doi.org/10.1371/journal.pone.0072923.> DOI: 10.1371/journal.pone.0072923 |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ2022141A3 (cs) | 2023-10-11 |
| CZ309857B6 (cs) | 2023-12-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11896704B2 (en) | Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes | |
| EP1638991B1 (fr) | Composition cosmetique ou dermopharmaceutique pour reduire les signes du vieillissement cutane | |
| KR102610786B1 (ko) | 할로모나스 발효 추출물을 함유한 미용 조성물, 및 이의 용도 | |
| US9067967B2 (en) | Peptides useful in the treatment and care of the skin and mucous membranes and their use in cosmetic or pharmaceutical compositions | |
| TWI595894B (zh) | 經改質受應力之酵母菌萃取物及相關組合物之化妝品用途 | |
| JP2025003941A (ja) | 皮膚の健康のための化粧料組成物及びその使用方法 | |
| KR102660303B1 (ko) | 피부, 모발 및 두피 건강을 개선하기 위한 효모 기반 마스크 | |
| EP2498772B1 (en) | Composition and methods for improving skin appearance | |
| CN107106617A (zh) | 包含来自南极假交替单胞菌的细菌细胞外产物的化妆品和/或药物组合物及其用途 | |
| JP6261560B2 (ja) | 抗微生物性の短リポペプチド | |
| MX2010011334A (es) | Composiciones cosmeticas que comprenden exopolisacaridos derivados de esteras microbianas y su uso. | |
| EP2408420A1 (en) | Use of tripeptides | |
| EP3536316A1 (en) | Acne strain-selective antibacterial agent | |
| WO2021204309A1 (en) | Casein-derived pentapeptide and composition comprising thereof and topical use thereof | |
| KR20230048515A (ko) | 천연 스킨케어 조성물 | |
| EP3305370A1 (en) | Algae autophagy activator | |
| WO2023186193A1 (en) | Hexapeptide, composition comprising thereof and topical use thereof | |
| EP3329905A1 (en) | Topical cosmetic compositions comprising an oligopeptide against anti-aging of the skin | |
| KR101252468B1 (ko) | 피부 트러블 개선용 화장품 조성물 | |
| CA3064050A1 (en) | Extracts from arthrospira and uses thereof | |
| EP3336173A1 (en) | A strain of aspergillus versicolor and applications thereof | |
| EP3549638A2 (en) | Pharmaceutical composition for use in treating an age-associated condition | |
| KR101453190B1 (ko) | 아마로젠틴을 포함하는 피부주름 개선용 조성물 | |
| HK1204453B (en) | Short antimicrobial lipopeptides |
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: 23718611 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 23718611 Country of ref document: EP Kind code of ref document: A1 |