JP6275042B2 - 有機分子の精製のための脂肪族化合物単位をその表面に含む吸着材 - Google Patents
有機分子の精製のための脂肪族化合物単位をその表面に含む吸着材 Download PDFInfo
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Description
−疎水性相互作用(逆相)
−親水性相互作用(順相)
−陽イオン交換
−陰イオン交換
−サイズ排除
−金属イオンキレート
使用された記号及びパラメータは、以下の意味を有する;
Lは、共有単結合、又は、−C(O)−、−S(O)2−、−CH2CH(OH)−及び−C(O)NH−からなる群より選ばれた2価のユニットを意味する。
Xは、1〜30個の炭素原子を有する1価の直鎖状脂肪族炭化水素基、又は、3〜30個の炭素原子を有する分枝鎖状若しくは環状炭化水素基を意味し、
ここで、前記基における1つ以上の、好ましくは1つのCH2部分は、O、S、−S(O)2−、−C(O)NH−又は−C(S)NH−に置換されていてもよく、
1つ以上の水素原子は、F、Cl、Br、−CN又は−NCに置換されていても良く、
前記基は2つの炭素原子間の二重結合を1つ以上含んでいてもよい。
ここで、
前記基の1つ以上、好ましくは1つのCH2部分は、水素供与体、及び/又は、水素受容体部分、例えば、O、S、−S(O)2−、−C(O)NH−又は−C(S)NH−を有する基によって置換されていてもよく、
そして、1つ以上の水素原子は、F、Cl、Br、−CN又は−NCに置換されていても良く、Fと−CNが好ましい。
ここで、
前記基における1つ以上、好ましくは1つのCH2部分は、O、S、−S(O)2−、−C(O)NH−又は−C(S)NH−に置換されていてもよく、
1つ以上の水素原子は、F、Cl、Br、−CN又は−NCに置換されていても良く、
前記基は2つの炭素原子間の二重結合を1つ以上含んでいてもよい。
ここで、nは1〜22、好ましくは6〜15、より好ましくは8〜13、最も好ましくは11である。
さらに好ましくは、前記支持材料を被覆する前記ポリマーは、親水性ポリマーである。前記ポリマーの親水性能は、前記吸着材と精製される化合物との間の親水性相互作用が起こり得ることを確実にする。
(i)官能基を有するポリマーを提供する;
(ii)担体の表面上に前記ポリマーを吸着させる;
(iii)少なくとも1種の架橋剤により、前記吸着させたポリマーの前記官能基の所定の部分を架橋させる;
(iv)更に、式(I)に従う1つ以上の残基によって、架橋した前記ポリマーの前記官能基の所定の部分を誘導体化する。
(i)本発明に従う吸着材または本発明に従う方法により製造された吸着材を含有するクロマトグラフィーカラムに、液体中に溶解または懸濁した有機分子を含む粗混合物を適用する;
(ii)溶離液を用いて、前記カラムから前記有機分子を溶離させる。
(i)本発明に従う吸着材を用いることによる有機分子の精製方法。
(ii)前記有機分子が薬理活性化合物である、実施形態(i)の方法。
(iii)前記有機分子の有する分子量が、500〜200000g/molの範囲内である、実施形態(i)または(ii)の方法。
(iv)前記有機分子が、エベロリムス、エベロリムスの誘導体、インスリン、インスリンの誘導体及びエンドトキシンからなる群から選択される、実施形態(i)〜(iii)のいずれかの方法。
4−トルエンスルホン酸を用いた漏出測定法(break-through measurment)によるアミン基の量の決定(前分析)(滴定方法)
それぞれの吸着材を、33.5×4mm寸法のカラムに充填する(ベッド容積0.42mL)。次に、前記充填されたカラムを、以下の媒体により流速1.0mL/分にて洗い流す。
・水 5mL
・100mM 酢酸アンモニウム水溶液 10mL
・水 1mL
・100mM トリフルオロ酢酸水溶液 10mL
・水 10mL
ポリビニルアミン水溶液(4.5g(水300g中)、トリフルオロ酢酸(TFA)を加えてpH8に調整される)を、Daisogel SP120 10 P 300gに加えた。該混合物を振動篩において5時間撹拌した後、真空中にて50℃で乾燥させた。重量が一定となった後、該吸着材をイソプロパノール900mLに懸濁し、更に、エチレングリコールジグリシジルエーテル3.64g(50mL中)を加えた。該混合物を70℃で6時間撹拌した。その後、前記吸着材を濾過し、イソプロパノール600mL、0.5M TFA(水中)2400mL、水600mL、ジメチルホルムアミド(DMF)600mL、0.1M トリエチルアミン(TEA)(DMF中)1800mL及びDMF600mLにより洗浄した。
実施例1にて製造された吸着材を、ベットサイズ250×25.4mmの軸圧縮ModColスチール製カラムに充填した。酢酸エチル/ジクロロメタン 1/1の移動相を40mL/分にて用いて、1.0%のサンプルロードを適用した。実質的にエベロリムス80〜85重量%及びラパマイシン15〜20重量%からなる粗混合物を、図1に従い分画した。図2は、該粗混合物(実線)と比較した際の精製エベロリムス(破線)の分析クロマトグラムを示す。該結果を、以下の表1にも示す。
ポリビニルアミン水溶液(30g(水400g中)、塩化水素酸(HCl)を加えてpH8に調整される)を、Daisogel SP120−10 P 600gに加えた。該混合物を振動篩において6時間撹拌した後、真空中にて50℃で乾燥させた。重量が一定となった後、該吸着材をイソプロパノール3000mLに懸濁し、更にエチレングリコールジグリシジルエーテル12.1g(150mLイソプロパノール中)を加えた。該混合物を55℃で6時間撹拌した。その後、前記吸着材を濾過し、イソプロパノール3000mL、0.1M HCl(水中)9000mL、水3000mL及びメタノール4500mLにより洗浄した。以後の使用まで、前記吸着材を乾燥させた。
インスリンと、主な不純物としての脱アミド(desamido)−インスリン−A21を含む粗試料(3mg/mL、水/アセトニトリル/トリフルオロ酢酸(95/5/0.1)中)を、Dionex HPLC装置を用いて分離した。該装置は、4チャンネル低圧グラジエントポンプ(LPG 580、LPG 680またはLPG 3400)、オートサンプラー(Gina 50,ASI−100またはWPS−300)、6チャンネルカラム切替バルブ(Besta製)、カラムオーブン及びダイオードアレイUV検出器(UVD 170U、UVD 340SまたはVWD 3400)により構成される。該吸着材を、250×4mmのスチール製カラムに充填した。精製のため、以下の表2に示される3つの溶離液の異なるグラジエントを用いた。第1の溶離液は10mM NaKHPO4(水中)であり、第2の溶離液は10mM NaKHPO4/1M NaCl(水中)であり、第3の溶離液は1−プロパノールである。流速は1mL/分であった。注入容積は1mLであった。分画の推移を図4に示す。
Claims (8)
- 固体支持材料を含む吸着材であって、表面に以下の一般式(I)の残基を含む吸着材:
前記ポリマーフィルムのポリマーは、共有結合により互いに架橋しているが前記固体支持材料の表面には共有結合によって結合されていない個々の鎖を含み、又は、それらにより構成され、前記ポリマーは、親水基を含むポリマーである;
使用された記号及びパラメータは、以下の意味を有する;
Lは、共有単結合、又は、−C(O)−、−S(O)2−、−CH2CH(OH)−及び−C(O)NH−からなる群より選ばれた2価のユニットを意味する。
Xは、6〜15個の炭素原子を有する1価の直鎖状C 6 −C 15 −アルキル基を意味し、
ここで、
前記基における1つ以上のCH2部分は、O、S、−S(O)2−、−C(O)NH−又は−C(S)NH−に置換されていてもよく、
1つ以上の水素原子は、F、Cl、Br、−CN又は−NCに置換されていても良く、
前記基は2つの炭素原子間における二重結合を1つ以上含んでいてもよい。
- Lが、−C(O)−、−S(O)2−、−CH2CH(OH)−である、請求項1に記載の吸着材。
- Lが、−C(O)−である、請求項2に記載の吸着材。
- 前記ポリマーが、ポリアミン、ポリビニルアミン、またはポリアミンを含むコポリマーもしくはポリマー混合物である、請求項1〜3のいずれか1項に記載の吸着材。
- 有機分子の精製のための、請求項1〜4のいずれか1項に記載の吸着材の使用。
- 前記有機分子が薬理活性化合物である、請求項5に記載の使用。
- 前記有機分子が、親水性の部分及び疎水性の部分の両方を有している、請求項5または6に記載の使用。
- 前記有機分子が、エベロリムス、エベロリムスの誘導体、インスリン、インスリン及びびエンドトキシンの誘導体からなる群から選択される、請求項5〜7のいずれか1項に記載の使用。
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EP11181413.3 | 2011-09-15 | ||
EP11181413A EP2570183A1 (en) | 2011-09-15 | 2011-09-15 | Sorbent comprising on its surface an aliphatic unit for the purification of organic molecules |
PCT/EP2012/068197 WO2013037993A1 (en) | 2011-09-15 | 2012-09-17 | Sorbent comprising on its surface an aliphatic unit for the purification of organic molecules |
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JP2014534411A JP2014534411A (ja) | 2014-12-18 |
JP6275042B2 true JP6275042B2 (ja) | 2018-02-07 |
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JP2014530253A Expired - Fee Related JP6275042B2 (ja) | 2011-09-15 | 2012-09-17 | 有機分子の精製のための脂肪族化合物単位をその表面に含む吸着材 |
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US (1) | US9370766B2 (ja) |
EP (2) | EP2570183A1 (ja) |
JP (1) | JP6275042B2 (ja) |
KR (1) | KR20140103898A (ja) |
CN (1) | CN103974765B (ja) |
AR (1) | AR088157A1 (ja) |
CA (1) | CA2846683A1 (ja) |
SG (1) | SG11201400472UA (ja) |
WO (1) | WO2013037993A1 (ja) |
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DE102014012566A1 (de) * | 2014-08-29 | 2016-03-03 | Instraction Gmbh | Sorbens zur Bindung von Metallen und dessen Herstellung |
DE102014016412A1 (de) * | 2014-11-07 | 2016-05-12 | Instraction Gmbh | Chromatographisches Sorbens mit lipophilem aliphatischen Rest und anionischem oder deprotonierbarem Rest |
JP2016144774A (ja) * | 2015-02-06 | 2016-08-12 | 株式会社クラレ | 逆イオン浸透性の低いイオン交換膜及びその製造方法 |
DE102015115359B4 (de) | 2015-09-11 | 2023-07-27 | Bpc Arnold Gmbh Biopharma Consulting | Biosensorchip |
EP3290111A1 (en) * | 2016-08-31 | 2018-03-07 | InstrAction GmbH | Sorbent for the separation of insulin from a solution |
US11059856B2 (en) | 2016-09-15 | 2021-07-13 | Klawego Gmbh & Co. Kg | Use of a polymeric mesh for the purification of macromolecules |
CN112661957A (zh) * | 2020-12-22 | 2021-04-16 | 国网安徽省电力有限公司电力科学研究院 | 一种呋喃基聚酰胺的绿色合成方法 |
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US4920152A (en) * | 1986-05-13 | 1990-04-24 | Purdue Research Foundation | Reversed-phase packing material and method |
DE4028120C2 (de) | 1990-09-05 | 1996-09-19 | Hoechst Ag | Verfahren zur Reinigung von Insulin und/oder Insulinderivaten |
US5100547A (en) * | 1991-03-04 | 1992-03-31 | Monsanto Company | Chromatography supports consisting of an inorganic susbstrate coated with polybutadiene with alkyl side chains |
DE4130475A1 (de) * | 1991-09-13 | 1993-03-18 | Merck Patent Gmbh | Modifizierte chromatographische traegermaterialien |
EP1027121A4 (en) | 1997-04-25 | 2001-07-11 | Transgenomic Inc | IMPROVED LIQUID CHROMATOGRAPHIC MEDIUM FOR THE SEPARATION OF POLYNUCLEOTIDES |
US8163302B2 (en) * | 1998-04-29 | 2012-04-24 | Nanomimetics, Inc. | Methods of making and using surfactant polymers |
US20020164712A1 (en) * | 2000-12-11 | 2002-11-07 | Tonghua Gantech Biotechnology Ltd. | Chimeric protein containing an intramolecular chaperone-like sequence |
US7250214B2 (en) * | 2001-08-09 | 2007-07-31 | Waters Investments Limited | Porous inorganic/organic hybrid monolith materials for chromatographic separations and process for their preparation |
SE0303532D0 (sv) * | 2003-12-23 | 2003-12-23 | Amersham Biosciences Ab | Purification of immunoglobulins |
JP4907514B2 (ja) * | 2005-01-28 | 2012-03-28 | 株式会社リバース・プロテオミクス研究所 | 効率的にターゲット分子を探索する方法 |
KR20080059265A (ko) * | 2005-09-30 | 2008-06-26 | 일립사, 인코포레이티드 | 포유동물의 위장관으로부터 칼륨 이온을 선택적으로제거하기 위한 방법 및 조성물 |
US20100136072A1 (en) * | 2006-11-08 | 2010-06-03 | Massachusetts Institute Of Technology | Polymeric Coatings that Inactivate Viruses and Bacteria |
US7815803B2 (en) * | 2007-06-14 | 2010-10-19 | Roche Diagnostics Operations, Inc. | Preparation of samples for LC-MS/MS using magnetic particles |
US20090218276A1 (en) * | 2008-02-29 | 2009-09-03 | Brigham Young University | Functionalized diamond particles and methods for preparing the same |
SG178173A1 (en) * | 2009-07-28 | 2012-03-29 | Instraction Gmbh | Specific sorbent for binding proteins and peptides, and separation method using the same |
US20110151493A1 (en) * | 2009-12-09 | 2011-06-23 | Amgen Inc. | Polypeptide disulfide bond analysis |
-
2011
- 2011-09-15 EP EP11181413A patent/EP2570183A1/en not_active Withdrawn
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2012
- 2012-09-17 KR KR1020147008608A patent/KR20140103898A/ko active IP Right Grant
- 2012-09-17 WO PCT/EP2012/068197 patent/WO2013037993A1/en active Application Filing
- 2012-09-17 AR ARP120103426A patent/AR088157A1/es unknown
- 2012-09-17 JP JP2014530253A patent/JP6275042B2/ja not_active Expired - Fee Related
- 2012-09-17 CA CA2846683A patent/CA2846683A1/en not_active Abandoned
- 2012-09-17 EP EP12759442.2A patent/EP2755754A1/en not_active Withdrawn
- 2012-09-17 US US14/344,425 patent/US9370766B2/en not_active Expired - Fee Related
- 2012-09-17 SG SG11201400472UA patent/SG11201400472UA/en unknown
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KR20140103898A (ko) | 2014-08-27 |
CN103974765B (zh) | 2016-08-24 |
US9370766B2 (en) | 2016-06-21 |
CA2846683A1 (en) | 2013-03-21 |
JP2014534411A (ja) | 2014-12-18 |
CN103974765A (zh) | 2014-08-06 |
WO2013037993A1 (en) | 2013-03-21 |
US20150045533A1 (en) | 2015-02-12 |
EP2755754A1 (en) | 2014-07-23 |
SG11201400472UA (en) | 2014-04-28 |
EP2570183A1 (en) | 2013-03-20 |
AR088157A1 (es) | 2014-05-14 |
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