KR20110128335A - pH 응답성 리포솜 - Google Patents
pH 응답성 리포솜 Download PDFInfo
- Publication number
- KR20110128335A KR20110128335A KR1020117023505A KR20117023505A KR20110128335A KR 20110128335 A KR20110128335 A KR 20110128335A KR 1020117023505 A KR1020117023505 A KR 1020117023505A KR 20117023505 A KR20117023505 A KR 20117023505A KR 20110128335 A KR20110128335 A KR 20110128335A
- Authority
- KR
- South Korea
- Prior art keywords
- zwitterionic
- responsive
- liposomes
- liposome
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 239000002502 liposome Substances 0.000 title claims abstract description 155
- 150000002632 lipids Chemical class 0.000 claims abstract description 47
- 125000002091 cationic group Chemical group 0.000 claims abstract description 41
- 239000006185 dispersion Substances 0.000 claims abstract description 34
- 125000000129 anionic group Chemical group 0.000 claims abstract description 27
- 239000000470 constituent Substances 0.000 claims abstract description 23
- 230000002378 acidificating effect Effects 0.000 claims abstract description 21
- 239000012736 aqueous medium Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 25
- 125000000524 functional group Chemical group 0.000 claims description 24
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 17
- 150000002634 lipophilic molecules Chemical class 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 9
- 235000012000 cholesterol Nutrition 0.000 claims description 8
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 230000000717 retained effect Effects 0.000 claims description 2
- 239000013077 target material Substances 0.000 claims description 2
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 63
- 239000013076 target substance Substances 0.000 description 33
- DEGAKNSWVGKMLS-UHFFFAOYSA-N calcein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(O)=O)CC(O)=O)=C(O)C=C1OC1=C2C=C(CN(CC(O)=O)CC(=O)O)C(O)=C1 DEGAKNSWVGKMLS-UHFFFAOYSA-N 0.000 description 24
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 24
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- 230000008859 change Effects 0.000 description 23
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 description 20
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- -1 cationic lipid Chemical class 0.000 description 14
- 235000021314 Palmitic acid Nutrition 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 12
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- WLNARFZDISHUGS-MIXBDBMTSA-N cholesteryl hemisuccinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 WLNARFZDISHUGS-MIXBDBMTSA-N 0.000 description 10
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- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 2
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- 125000001165 hydrophobic group Chemical group 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
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- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
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- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 1
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- 125000003827 glycol group Chemical group 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Preparation (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009058063A JP5588619B2 (ja) | 2009-03-11 | 2009-03-11 | pH応答性リポソーム |
| JPJP-P-2009-058063 | 2009-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110128335A true KR20110128335A (ko) | 2011-11-29 |
Family
ID=42728416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117023505A Ceased KR20110128335A (ko) | 2009-03-11 | 2010-03-10 | pH 응답성 리포솜 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8871252B2 (enExample) |
| EP (1) | EP2407158A4 (enExample) |
| JP (1) | JP5588619B2 (enExample) |
| KR (1) | KR20110128335A (enExample) |
| WO (1) | WO2010104128A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6339884B2 (ja) * | 2014-07-17 | 2018-06-06 | 富士フイルム株式会社 | イミダゾール化合物およびそれを含有するリポソーム |
| GB201614120D0 (en) * | 2016-08-18 | 2016-10-05 | Univ Of Kwazulu-Natal | pH-responsive lipids |
| JP6462073B1 (ja) * | 2017-09-04 | 2019-01-30 | 一丸ファルコス株式会社 | pH感受性リポソームの製造方法 |
| JP6399530B1 (ja) * | 2017-09-04 | 2018-10-03 | 一丸ファルコス株式会社 | pH感受性リポソーム |
| WO2019045097A1 (ja) * | 2017-09-04 | 2019-03-07 | 一丸ファルコス株式会社 | pH感受性リポソームおよびその製造方法 |
| JP7406057B2 (ja) | 2021-03-03 | 2023-12-27 | 東洋ビューティ株式会社 | 外用微粒子カプセル製剤及び皮膚外用剤 |
| CN119552796A (zh) * | 2024-11-29 | 2025-03-04 | 艾美行动生物制药有限公司 | 一种用于细胞培养添加物包载的pH敏感脂质体及制备方法 |
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| US8382004B2 (en) * | 2001-04-04 | 2013-02-26 | Graftech International Holdings Inc. | Flexible graphite flooring heat spreader |
| JP5093547B2 (ja) * | 2001-08-24 | 2012-12-12 | 日本ケミカルリサーチ株式会社 | 両イオン性脂質およびその用途 |
| DE10207177A1 (de) | 2002-02-19 | 2003-09-04 | Novosom Ag | Fakultativ kationische Lipide |
| CA2821167C (en) * | 2004-05-03 | 2016-06-28 | Merrimack Pharmaceuticals, Inc. | Drug delivery liposomes containing anionic polyols or anionic sugars |
| US8658203B2 (en) | 2004-05-03 | 2014-02-25 | Merrimack Pharmaceuticals, Inc. | Liposomes useful for drug delivery to the brain |
| AU2005300638A1 (en) | 2004-11-05 | 2006-05-11 | Novosom Ag | Improvements in or relating to pharmaceutical compositions comprising an oligonucleotide as an active agent |
| US7838685B2 (en) | 2005-04-27 | 2010-11-23 | Shinji Takeoka | Cationic amino acid type lipid |
| JP5571308B2 (ja) * | 2005-09-15 | 2014-08-13 | マリーナ バイオテック,インコーポレイテッド | 両性リポソームにおけるまたはそれに関する改善 |
| EP1764089A1 (en) | 2005-09-15 | 2007-03-21 | Novosom AG | Serum stable liposomes comprising amphoter II lipid mixtures |
| EP1957044B1 (en) * | 2005-12-01 | 2013-03-13 | Pronai Therapeutics, Inc. | Amphoteric liposome formulation |
| JP5253716B2 (ja) * | 2006-02-09 | 2013-07-31 | 日本ケミカルリサーチ株式会社 | pH応答性分子集合体 |
| US8193246B2 (en) * | 2006-12-19 | 2012-06-05 | Marina Biotech, Inc. | Lipids and lipid assemblies comprising transfection enhancer elements |
| US20080145413A1 (en) | 2006-12-19 | 2008-06-19 | Steffen Panzner | Lipids and lipid assemblies comprising transfection enhancer elements |
| US8241647B2 (en) * | 2007-05-17 | 2012-08-14 | Waseda University | Amphiphilic molecule, molecular assembly comprising the amphiphilic molecule, and use of the molecular assembly |
| AU2008309880B2 (en) * | 2007-10-12 | 2014-07-10 | Biontech Delivery Technologies Gmbh | Amphoteric liposomes comprising neutral lipids |
| WO2009051712A1 (en) * | 2007-10-15 | 2009-04-23 | Pronai Therapeutics, Inc. | Dnai amphoteric liposome formulation |
| US20100129430A1 (en) * | 2008-11-24 | 2010-05-27 | Stavroula Sofou | Liposome drug carriers with ph-sensitivity |
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| JP5588619B2 (ja) | 2014-09-10 |
| US8871252B2 (en) | 2014-10-28 |
| WO2010104128A1 (ja) | 2010-09-16 |
| EP2407158A4 (en) | 2013-09-04 |
| JP2010209012A (ja) | 2010-09-24 |
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