JP5654493B2 - 重合プロテオリポソームを用いたナノ加工膜 - Google Patents
重合プロテオリポソームを用いたナノ加工膜 Download PDFInfo
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- JP5654493B2 JP5654493B2 JP2011549234A JP2011549234A JP5654493B2 JP 5654493 B2 JP5654493 B2 JP 5654493B2 JP 2011549234 A JP2011549234 A JP 2011549234A JP 2011549234 A JP2011549234 A JP 2011549234A JP 5654493 B2 JP5654493 B2 JP 5654493B2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- JJAHTWIKCUJRDK-UHFFFAOYSA-N succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate Chemical compound C1CC(CN2C(C=CC2=O)=O)CCC1C(=O)ON1C(=O)CCC1=O JJAHTWIKCUJRDK-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
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Description
本発明のナノ加工膜を得るために、タンパク質(6)をUV架橋性リポソーム(1)に組み込むことによって、重合プロテオリポソームが最初に形成された。該UV架橋性リポソーム(1)は、天然脂質の構造を模倣した材料を用いた合成物である。図1に示すように、該UV架橋性リポソーム(1)(例えば1−パルミトイル−2−(10Z,12Z−トリコサジイノイル)−sn−グリセロ−3−ホスホコリン、1−パルミトイル−2−(10Z,12Z−トリコサジイノイル)−sn−グリセロ−3−ホスホエタノールアミン、1,2−ジ−(10Z,12Z−トリコサジイノイル)−sn−グリセロ−3−ホスホコリン、1−2−(10Z,12Z−トリコサジイノイル)−sn−グリセロ−3−ホスホエタノールアミン)は、疎水部(3)にUV架橋性の化学構造(2);10,12−ペンタコサイジン酸(PCDA)およびその親水部の官能基誘導体(蛍光性ジアセチレンモノマー)を持つ。UV架橋性の化学構造が疎水尾部(5)の一つまたは全てに含まれてよいことは理解される。また該UV架橋性リポソームは、親水部(4)を含む。実施形態の一つにおいては、UV架橋性の化学構造(2)は内部架橋のためのジアセチレンを含んでよい。しかし、通常の当業者は本発明の範囲から逸脱すること無くさらなるUV架橋性の化学構造(2)を選択し得るため、本発明はこの特定のUV架橋性の化学構造(2)に限定されない。図1は、疎水部(3)に1−パルミトイル−2−(10Z,12Z−トリコサジイノイル)−sn−グリセロ−3−ホスホエタノールアミン(Diyne PE)の構造図を含む本発明の実施形態の一つを示す。この内部UV架橋によって、物理的ストレスに対して強い機械的耐性を持つリポソームが提供される。UV架橋性リポソーム(1)が形成された後、既知の方法を用いて、タンパク質(6)がリポソームの壁に組み込まれる。本発明の実施形態の一つにおいては、組み込むタンパク質(6)としてアクアポリンが使用される。しかし、当業者に既知のように、UV架橋性リポソーム(1)に他のタンパク質(6)が組み込まれ得ることは理解される。ひとたび該タンパク質(6)がUV架橋性リポソーム(1)に組み込まれると、重合プロテオリポソーム(7)を形成するために、該プロテオリポソームはUV照射を用いて重合化される。図2はUV架橋前のプロテオリポソーム(7)を示す。該プロテオリポソームがUV照射された後、リポソーム(1)の疎水部(3)中のUV架橋性官能基(2)によって重合プロテオリポソーム(8)が形成される。
UV架橋性の化学基(例えばポリアセチレン)を疎水部に持つUV反応性の重合性脂質(例えば、16:0−23:2ジインPC(アバンティ・ポーラ・リピッド社カタログ番号790146)または23:2ジインPC(アバンティ・ポーラ・リピッド社カタログ番号870016)または10−12−ペンタコサイジン酸、ポリジアセチレン等)を、濃度5mg/mlでクロロホルムまたはt−ブタノールに溶解した。薄膜は二つの方法で作製し得る:
a.溶解した脂質溶液を、完全に乾燥したガラス製吸引フラスコに移した。ガラス器内に薄膜フィルムを形成するために、重質ガス(アルゴンまたは窒素ガス)噴流下で緩やかに振とうして該溶液を乾燥した。溶媒を完全に除去するために、乾燥した薄膜フィルムを4時間またはさらに長時間浄化した。
b.t−ブタノールに溶解した脂質溶液が入った丸底フラスコをロータリー・ベーパーに取り付け、約40℃から70℃、減圧下で該溶剤を除去した。該フィルムを約60分、または完全に乾かすためにさらに長時間、乾燥した。該フィルムは直ちに使用するか、または不活性ガス中で−80℃で保存し得る。
共有結合による化学的架橋を構築するために、光反応性架橋剤、ゼロ距離架橋剤、ホモ二官能性架橋剤、ヘテロ二官能性架橋剤、三官能性架橋剤、四官能性架橋剤、デンドリマー、およびその他のような、多様な種類の化学コンジュゲーションを使用した。光反応性架橋剤には、NHS−アクリル酸およびNHS−ASA(NHS−4−アジドサリチル酸)のようなアクリル酸誘導体およびアジ化アクリル誘導体、ならびにビス−[β−(4−アジドサリチルアミド)エチル]ジスルフィド(BASED)がある。アミド結合のためのゼロ距離架橋剤には、EDC(1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド)塩酸塩、スルホ−NHS(N−ヒドロキシスルホスクシンイミド)を含むEDC、CMS(1−シクロヘキシル−3−(2−モルホリノエチル)カルボジイミド)、DCC(ジシクロヘキシルカルボジイミド)、DIC(ジイソプロピルカルボジイミド)、ウッドワード試薬K(N−エチル−3−フェニルイソオキサゾリウム−3’−スルホナート)、CDI(N,N’−カルボニルジイミダゾール)のようなカルボジイミドがある。従来のタンパク質結合法において、EDCはペプチド結合(アミド結合)を作るための生体適合性のメディエータである。この反応では、EDCによって活性化されたカルボキシル酸基またはリン酸基を介する共有結合による架橋(ペプチド結合)に、アミン基が必要である。ホモ官能性架橋剤には、ホモ官能性NHSエステルである、ジチオビス(スクシンイミジルプロピオナート)(DSP)、3,3’−ジチオビス(スルホスクシンイミジルプロピオナート)(DTSSP)、スベリン酸ジスクシンイミジル(DSS)、スベリン酸ビス(スルホスクシンイミジル)(BS3)、酒石酸ジスクシンイミジル(DST)、酒石酸ジスルホスクシンイミジル(スルホ−DST)、ビス[2−(スクシンイミジルオキシカルボニルオキシ)エチル]スルホン(BSOCOES)、ビス[2−(スルホスクシンイミジルオキシカルボニルオキシ)エチル]スルホン(スルホ−BSOCOES)、エチレングリコールビス(スクシンイミジルスクシネート)(EGS)、エチレングリコールビス(スルホスクシンイミジルスクシネート)(スルホ−EGS)、グルタル酸ジスクシンイミジル(DSG)、炭酸N,N’−ジスクシンイミジル(DSC)、およびビスNHS(PEG)n、ならびにアジポイミド酸ジメチル(DMA)、ピメルイミド酸ジメチル(DMP)、スベルイミド酸ジメチル(DMS)、ジメチル3,3−ジチオビスプロピオンイミダート(DTBT)のようなホモ官能性イミドエステルがある。ヘテロ官能性架橋剤には、NHS−ヒドラジン基(SANH)、NHS−アルデヒド基(SFB)等がある。三官能性架橋剤には、4−アジド−2−ニトロフェニルビオシチン−4−ニトロフェニルエステル(ABNP)、スルホスクシンイミジル−2−[6−(ビオチンアミド)−2−(p−アジドベンズアミド)ヘキサノアミド]エチル−1,39−ジチオプロピオナート(スルホ−SBED)がある。
重合プロテオリポソームは、溶解性溶剤および他の反応に対して耐性が高い。従って、UV架橋性脂質(またはリポソーム。次では脂質に関してのみ例示する)自体を、ミオシン−アクチン繊維間の構造と同様に、重合性プロテオリポソームとポリアミド薄層との間の優良なリンカーとして使用し得ることが明らかになった。UV架橋性脂質をポリアミド薄層に植え込むために、エタノールアミンを含有する天然脂質およびUV架橋性脂質を使用した。該エタノールアミン基はポリアミド・マトリクスを形成するために追加のアミン源として使用し、疎水部がマトリクス面の反対側に向くことを予想した。この工程を行うために、MCE(セルロース混合エステル)およびナイロン多孔膜(デュラポアおよびアイソポア膜のような他の膜も使用し得る)を、脂質溶剤溶液中に浸した。続いて該溶剤を蒸発させ、m−フェニレンジアミンのようなジアミン化合物または他の何らかの多官能性アミン中でインキュベーションした。過剰量のアミン源を除去し乾燥した後、ヘキサンのような無極性溶媒に溶解したトリメソイルクロリド(TMC)のような多官能性ハロゲン化アシル(または、アミド結合を形成し得る他の何らかのアシル誘導体)で処理した。該反応は数秒で終了し、過剰量のTMCを脱イオン水中で完全に洗い流した。図4に示す構造が予想された。水接触角測定試験によって、脂質の親水部について予想されるよりも、疎水性が上昇していることが示された。この反応後、脂質含有マトリクスの疎水性が上昇していると考えられた。このことは、予想された通り親水部が外側に向いていることを意味する。
インタースティシャル・マトリクスへの重合プロテオリポソームのイン・シチュ組み込みのためには、生体適合性の材料が必要である。ポリエチレングリコール(PEG)およびアミン・デンドリマーは該目的のための優良な候補である。
重合プロテオリポソーム技術のさらなる適用においては、重合プロテオリポソームで被覆した加水分解ナイロン糸を生産し得る。高温(80℃)における該加水分解ナイロン糸は、その表面にカルボキシル基およびアミン基を含む。以前に言及したゼロ距離結合法と同様に、図7(a)に示すようにEDCを介するアミド結合形成によって、重合プロテオリポソームを活性化された糸上に共有結合で架橋し得る。またはAPTESで活性化されアミン架橋剤と相互作用するセルロース糸を使用してもよい。
Claims (14)
- リポソーム壁に組み込まれたタンパク質(6)を有する複数のリポソーム(8)を含む膜であって、
前記複数のリポソームは内部UV架橋されており、前記複数のリポソーム間、あるいは前記複数のリポソームとインタースティシャル・マトリクス、または支持膜間には、前記複数のリポソームの親水部(4)による外部架橋が存在する、
ことを特徴とする膜。 - 前記複数のリポソーム(8)は、2つの疎水尾部(5)を有する複数の脂質(1)を備え、前記内部UV架橋は、前記2つの疎水尾部(5)のうちの1つまたは両方に含まれる、
ことを特徴とする請求項1に記載の膜。 - 前記内部UV架橋はジアセチレンより得られる、
ことを特徴とする請求項1または2に記載の膜。 - 前記親水部(4)の前記架橋は、多官能性アミン、カルボキシル酸、および/またはリン酸基より提供される、
ことを特徴とする請求項1から3のいずれかに記載の膜。 - 前記親水部(4)の前記架橋は、カルボジイミドより得られるアミド結合によって提供される、
ことを特徴とする請求項1から3のいずれかに記載の膜。 - 前記外部架橋は、1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド塩酸塩および/またはアミン架橋剤によって提供される、
ことを特徴とする請求項1から3のいずれかに記載の膜。 - 基膜(12)を含む、
ことを特徴とする請求項1から6のいずれかに記載の膜。 - 前記基膜(12)が、セルロース混合エステル、セルロース、および/またはポリアミドである、
ことを特徴とする請求項7に記載の膜。 - 前記基膜(12)がポリアミドである、
ことを特徴とする請求項7に記載の膜。 - 前記複数のリポソーム(8)は、前記複数のリポソーム(8)を形成する前記複数の脂質(1)の前記親水部(4)により前記基膜(12)と結合される、
ことを特徴とする請求項7から9のいずれかに記載の膜。 - 共有結合性架橋のためにカルボキシル基またはアミン基を表面に含む加水分解ナイロン糸および/または3−アミノプロピルトリエトキシシランで活性化されたセルロース糸(16)が、プロテオリポソーム(8)で被覆されている、
ことを特徴とする請求項1から10のいずれかに記載の膜。 - アクアポリン・タンパク質ファミリーのタンパク質(6)が前記複数のリポソーム(8)に組み込まれた、膜が水ろ過膜である、
ことを特徴とする請求項1から11のいずれかに記載の膜。 - 請求項1に記載の膜を調合するための工程であって、当該工程は、
(a)UV架橋性官能基を備えた基膜(12)の提供するステップと、
(b)リポソーム壁に組み込まれたタンパク質(6)を有し、内部および外部の両方のUV架橋性官能基を備えた複数のリポソーム(8)を前記基膜(12)へ適用するステップと、
(c)UV照射を受けさせるステップと、
を含む、工程。 - 請求項1に記載の膜を調合するための工程であって、当該工程は、
(a)UV架橋性官能基を備えた基膜(13)を型(14)内に提供するステップと、
(b)(i)リポソーム壁に組み込まれたタンパク質(6)を有し、内部UV架橋された複数のリポソーム(8)と(ii)UV架橋性PEG溶液を、前記基膜(13)へ適用するステップと、
(c)UV照射を受けさせるステップと、
(d)前記型(14)から形成された膜を取り外すステップと、
を含む、工程。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US14952109P | 2009-02-03 | 2009-02-03 | |
US61/149,521 | 2009-02-03 | ||
PCT/US2010/023043 WO2010091078A2 (en) | 2009-02-03 | 2010-02-03 | Nanofabricated membrane using polymerized proteoliposomes |
Publications (2)
Publication Number | Publication Date |
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JP2012516776A JP2012516776A (ja) | 2012-07-26 |
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EP (1) | EP2393481B1 (ja) |
JP (1) | JP5654493B2 (ja) |
KR (1) | KR101367437B1 (ja) |
CN (1) | CN102395357B (ja) |
AU (1) | AU2010210664B2 (ja) |
CA (1) | CA2751331C (ja) |
DK (1) | DK2393481T3 (ja) |
IL (1) | IL214395A (ja) |
MA (1) | MA33094B1 (ja) |
MX (1) | MX2011008050A (ja) |
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US8505743B2 (en) * | 2009-04-08 | 2013-08-13 | Michigan Molecular Institute | Surface modification of polyamide reverse osmosis membranes |
EA037202B1 (ru) * | 2009-06-26 | 2021-02-18 | Катхолике Университейт Лёвен, К.У. Лёвен Р Энд Д | Слитые белки для лечения инфекций, вызванных грамотрицательными бактериями |
US8647853B2 (en) | 2009-12-15 | 2014-02-11 | Ensovi, Llc | Foam microreactor for multi-phase shear-sensitive reactions |
DK177307B1 (en) * | 2010-12-17 | 2012-11-12 | Aquaporin As | A liquid membrane |
EP2758156B8 (en) | 2011-09-21 | 2020-06-17 | Nanyang Technological University | Aquaporin based thin film composite membranes |
CN103648625B (zh) * | 2012-05-31 | 2015-12-30 | Lg化学株式会社 | 包含碳二亚胺化合物的高渗透通量的反渗透膜及其制备方法 |
WO2013180659A1 (en) * | 2012-06-01 | 2013-12-05 | National University Of Singapore | Method of making a membrane and a membrane for water filtration |
KR101949125B1 (ko) | 2012-07-04 | 2019-02-18 | 고려대학교 산학협력단 | pH 민감성 형광 발광의 폴리디아세틸렌 리포좀 및 이를 포함하는 약물 전달체 |
GB201300465D0 (en) * | 2013-01-11 | 2013-02-27 | Aquaporin As | A hollow fiber module having tfc-aquaporin modified membranes |
DK177696B1 (en) * | 2013-02-25 | 2014-03-17 | Aquaporin As | Systems for water extraction |
DK179128B1 (en) * | 2014-02-24 | 2017-11-20 | Aquaporin As | Systems for utilizing the water content in fluid from a renal replacement therapy process |
GB201405390D0 (en) | 2014-03-26 | 2014-05-07 | Applied Biomimetic As | Process for making membranes |
GB201405391D0 (en) | 2014-03-26 | 2014-05-07 | Applied Biomimetic As | Novel polymers and process for making membranes |
CN110080960A (zh) | 2014-09-08 | 2019-08-02 | 应用仿生学有限公司 | 发电方法 |
MX2018009617A (es) * | 2016-02-08 | 2019-05-02 | Aquaporin As | Nanoestructuras autoensambladas y membranas de separacion que comprenden canales de agua de acuaporina y metodos de obtencion y uso de las mismas. |
GB201605070D0 (en) | 2016-03-24 | 2016-05-11 | Applied Biomimetic As | Power generation process |
GB201605068D0 (en) | 2016-03-24 | 2016-05-11 | Applied Biomimetic As | Electricity generation process |
EP3219381A1 (de) * | 2016-03-16 | 2017-09-20 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Poröse dünnschichtmembran, verfahren zu ihrer herstellung sowie verwendungsmöglichkeiten |
US20190177756A1 (en) * | 2016-08-18 | 2019-06-13 | The Board Of Trustees Of The Leland Stanford Junior University | Production and use of phosphoethanolamine cellulose and derivatives |
US10842746B1 (en) | 2016-08-25 | 2020-11-24 | Verily Life Sciences Llc | Bi-directionally crosslinked liposomes and method of making same |
US20200188864A1 (en) * | 2016-11-11 | 2020-06-18 | Aquaporin A/S | Self-assembled polymeric vesicular structures with functional molecules |
KR102038282B1 (ko) * | 2016-12-29 | 2019-11-26 | 인하대학교 산학협력단 | 다공성 구조체 및 이의 제조방법 |
CN106928324A (zh) * | 2017-01-20 | 2017-07-07 | 宁波日新恒力科技有限公司 | 一种提高囊泡中水通道蛋白表达活性的方法及反渗透膜 |
GB201711240D0 (en) | 2017-07-12 | 2017-08-23 | Saltkraft Aps | Power generation process |
GB201711238D0 (en) | 2017-07-12 | 2017-08-23 | Saltkraft Aps | Power generation process |
JP7326303B2 (ja) * | 2017-10-25 | 2023-08-15 | アクアポリン エー/エス | 膜貫通タンパク質を組み込んだ小胞 |
WO2019161325A1 (en) * | 2018-02-19 | 2019-08-22 | Boise State University | Radiation-triggered liposomes |
WO2019187870A1 (ja) * | 2018-03-29 | 2019-10-03 | 栗田工業株式会社 | 選択性透過膜、その製造方法及び水処理方法 |
JP6939742B2 (ja) * | 2018-03-29 | 2021-09-22 | 栗田工業株式会社 | 選択性透過膜、その製造方法及び水処理方法 |
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CN112973467B (zh) * | 2019-12-02 | 2022-12-13 | 欧美新材料(浙江)有限公司 | 一种复合纳滤膜的制备方法及复合纳滤膜 |
CN111151137B (zh) * | 2020-01-03 | 2022-03-15 | 浙江工业大学 | 一种高通量高截盐反渗透复合膜及其制备方法 |
WO2023187106A1 (en) * | 2022-03-31 | 2023-10-05 | Illumina Cambridge Limited | Barriers including cross-linked amphiphilic molecules, and methods of making the same |
US20230381718A1 (en) * | 2022-03-31 | 2023-11-30 | Illumina Cambridge Limited | Barriers including molecules covalently bonded to amphiphilic molecules, and methods of making the same |
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WO2007127439A2 (en) * | 2006-04-28 | 2007-11-08 | Children's Hospital Medical Center | Compositions comprising fusogenic proteins or polypeptides derived from prosaposin for application in transmembrane drug delivery systems |
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IL214395A (en) | 2016-02-29 |
SG173165A1 (en) | 2011-08-29 |
DK2393481T3 (da) | 2019-07-15 |
WO2010091078A2 (en) | 2010-08-12 |
KR101367437B1 (ko) | 2014-02-26 |
KR20110117696A (ko) | 2011-10-27 |
IL214395A0 (en) | 2011-09-27 |
US9359230B2 (en) | 2016-06-07 |
EP2393481A4 (en) | 2016-12-07 |
AU2010210664A1 (en) | 2011-08-25 |
CA2751331A1 (en) | 2010-08-12 |
CA2751331C (en) | 2016-04-26 |
MA33094B1 (fr) | 2012-03-01 |
EP2393481A2 (en) | 2011-12-14 |
MX2011008050A (es) | 2011-09-09 |
US20120043275A1 (en) | 2012-02-23 |
CN102395357B (zh) | 2015-08-26 |
WO2010091078A3 (en) | 2011-07-07 |
CN102395357A (zh) | 2012-03-28 |
EP2393481B1 (en) | 2019-04-17 |
JP2012516776A (ja) | 2012-07-26 |
AU2010210664B2 (en) | 2013-10-10 |
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