JP6918276B2 - キトサン−プルロニック複合体、及びこれを含むナノ運搬体 - Google Patents
キトサン−プルロニック複合体、及びこれを含むナノ運搬体 Download PDFInfo
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- JP6918276B2 JP6918276B2 JP2020520410A JP2020520410A JP6918276B2 JP 6918276 B2 JP6918276 B2 JP 6918276B2 JP 2020520410 A JP2020520410 A JP 2020520410A JP 2020520410 A JP2020520410 A JP 2020520410A JP 6918276 B2 JP6918276 B2 JP 6918276B2
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- 229920001983 poloxamer Polymers 0.000 title claims description 46
- 239000003814 drug Substances 0.000 claims description 51
- 229940079593 drug Drugs 0.000 claims description 45
- 229920001661 Chitosan Polymers 0.000 claims description 39
- 229920000642 polymer Polymers 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 16
- 231100000245 skin permeability Toxicity 0.000 claims description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 14
- 239000002539 nanocarrier Substances 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 9
- 238000011068 loading method Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000012153 distilled water Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 230000003796 beauty Effects 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 2
- 210000003491 skin Anatomy 0.000 description 23
- 238000005259 measurement Methods 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VOFUROIFQGPCGE-UHFFFAOYSA-N nile red Chemical compound C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=O)C2=C1 VOFUROIFQGPCGE-UHFFFAOYSA-N 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 210000000434 stratum corneum Anatomy 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000003013 cytotoxicity Effects 0.000 description 4
- 231100000135 cytotoxicity Toxicity 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
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- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 125000003275 alpha amino acid group Chemical group 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
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- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- -1 whitening Substances 0.000 description 2
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000004520 agglutination Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229920001992 poloxamer 407 Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- VSIVTUIKYVGDCX-UHFFFAOYSA-M sodium;4-[2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)tetrazol-2-ium-5-yl]benzene-1,3-disulfonate Chemical compound [Na+].COC1=CC([N+]([O-])=O)=CC=C1[N+]1=NC(C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)=NN1C1=CC=C([N+]([O-])=O)C=C1 VSIVTUIKYVGDCX-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
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Description
(PEO)a−(PPO)b−(PEO)a
Claims (11)
- 経皮透過用ナノ運搬体であって、
プルロニック高分子の両末端にキトサンが置換された、キトサン−プルロニック複合体、及びプルロニック高分子を含み、
前記プルロニック高分子が、下記化1で表され、
前記キトサン−プルロニック複合体とプルロニック高分子の重量比が、8:2である、
ナノ運搬体。
(化1)
(PEO) a −(PPO) b −(PEO) a
(前記PEOはポリエチレンオキシド、前記PPOはポリプロピレンオキシドであり、前記a及びbはそれぞれ独立に1乃至300の整数である。) - 前記キトサン−プルロニック複合体における、キトサンの分子量が3乃至760kDaである、請求項1に記載のナノ運搬体。
- 前記ナノ運搬体は、大きさが500nm以下である、請求項1に記載のナノ運搬体。
- 前記ナノ運搬体は、表面電荷が0乃至50mVである、請求項1に記載のナノ運搬体。
- 前記ナノ運搬体は肌透過率の低い薬物又は活性成分を運搬する、請求項1に記載のナノ運搬体。
- 前記ナノ運搬体は、肌透過率の低い薬物又は活性成分のローディング(loading)効率が90%以上である、請求項5に記載のナノ運搬体。
- 前記肌透過率の低い薬物又は活性成分は、化粧品、医薬品、医薬外品、又は美容用品に使用される機能性の物質である、請求項5に記載のナノ運搬体。
- 前記ナノ運搬体は、化粧品、医薬品、医薬外品、又は美容用品に用いられる、請求項1に記載のナノ運搬体。
- 前記ナノ運搬体は、肌透過率の低い薬品又は活性成分を含有する薬物複合体に用いられる
、請求項1に記載のナノ運搬体。 - (a)プルロニック高分子とキトサンとを混合し、プルロニック高分子の末端にキトサン
が置換された複合体を製造する段階と、
(b)前記複合体を溶媒としてのアセトンの存在下でプルロニック高分子と混合して混合物を製造する段階と、
(c)前記混合物を蒸留水に滴下する段階と、
(d)前記混合物が滴下した蒸留水を攪拌する段階と、を含み、
前記プルロニック高分子が、下記化1で表され、
前記キトサン−プルロニック複合体とプルロニック高分子の重量比が、8:2である、
請求項1に記載の経皮透過用ナノ運搬体の製造方法。
(化1)
(PEO) a −(PPO) b −(PEO) a
(前記PEOはポリエチレンオキシド、前記PPOはポリプロピレンオキシドであり、前記a及びbはそれぞれ独立に1乃至300の整数である。) - 前記(a)段階で、3乃至760kDaの分子量のキトサンを混合する、請求項10に記
載のナノ運搬体の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020170078481A KR102009240B1 (ko) | 2017-06-21 | 2017-06-21 | 키토산-플루로닉 복합체 및 이를 포함하는 나노운반체 |
KR10-2017-0078481 | 2017-06-21 | ||
PCT/KR2018/006706 WO2018236090A2 (ko) | 2017-06-21 | 2018-06-14 | 키토산-플루로닉 복합체 및 이를 포함하는 나노운반체 |
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US8486528B2 (en) * | 2008-01-22 | 2013-07-16 | Gwangju Institute Of Science And Technology | Temperature-sensitive nano-carriers |
US20100016450A1 (en) * | 2008-07-21 | 2010-01-21 | Otonomy, Inc. | Controlled release delivery devices for the treatment of otic disorders |
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US9433699B2 (en) | 2011-11-21 | 2016-09-06 | Innotherapy Inc. | Hydrogel comprising catechol group-coupled chitosan or polyamine and poloxamer comprising thiol group coupled to end thereof, preparation method thereof, and hemostat using same |
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CN110799177B (zh) | 2022-06-17 |
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CN110799177A (zh) | 2020-02-14 |
US11471534B2 (en) | 2022-10-18 |
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EP3643300A2 (en) | 2020-04-29 |
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