JP4607760B2 - トリアジン化合物及びアフィニティークロマトグラフィー用の多次元ライブラリーを形成するためのその使用 - Google Patents
トリアジン化合物及びアフィニティークロマトグラフィー用の多次元ライブラリーを形成するためのその使用 Download PDFInfo
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- JP4607760B2 JP4607760B2 JP2005502337A JP2005502337A JP4607760B2 JP 4607760 B2 JP4607760 B2 JP 4607760B2 JP 2005502337 A JP2005502337 A JP 2005502337A JP 2005502337 A JP2005502337 A JP 2005502337A JP 4607760 B2 JP4607760 B2 JP 4607760B2
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Description
本発明は、単一のトリアジン環に基づくリガンドに比べて化学的多様性のより大きなそしてより選択性の亢進した大きなリガンドを提供するために有用なアフィニティーライブラリーが、2つ以上のトリアジン環を組み合わせて、一つのリガンド構造とすることによって得られることに基づく。
各Zは、同じか又は異なり、そして以下の:
各Xは、同じか又は異なり、そして多価(二価を含む)アミニル基又はジアミニル末端を有するスペーサーであり;
各Yは、同じか又は異なるアミニル基であり;そして
Mは、支持マトリックスである。}
を有する。
支持体材料Mは、粒子状又は非粒子状、可溶性又は不溶性、多孔質又は非多孔質のいかなる好適な化合物又は物質であることもできる。それは、定義されたアフィニティーリガンドに関しては、アフィニティーリガンドと接触させられる溶液中の溶質からアフィニティーリガンドを分離する便利な手段を提供する。
A=B=C(i)(μモル/安定化させたゲルのg)となり、
第二塩素イオン、C(ii)が除去されると、以下の:
A=B=C(i)=C(ii);そして
C(i)+C(ii)=2A=2Bとなる。
この実施例は、エポキシド‐活性化PuraBead樹脂の製造を例解する。PuraBeadは耐久性を助けるために架橋された多孔質ビーズ状のアガロース支持体である。
この実施例は、エポキシド活性化ゲルからのアミノ化ゲルの製造方法を例解する。
この実施例は、アミン化樹脂と塩化シアヌルとの反応がジクロロトリアジン‐活性化ゲルを生じさせたことを例解する。
この実施例は、ジクロロトリアジンゲルへの第1のアミンの付加を例解する。
この実施例は、高温におけるジアミンスペーサーによる第二塩素イオンの置換を例解する。
この実施例は、第二トリアジン環への第1のアミンの付加を例解する。
この実施例は、最終的なアミン(Y3)の第二トリアジン環への付加の組み合わせによって、式VIIIによる3Dリガンドのライブラリーが得られることを例解する。
3Dライブラリーの合成のために選ばれるアミンは、一級、二級、脂肪族、芳香族、複素環、アリール、キラル、荷電したもの又はこれらの組み合わせのいかなるものであってもよい。反応条件は、選ばれるアミンの溶解度によって変化することができる。溶媒は水、50%DMF及び純粋のDMFから選ばれる。塩酸塩として又はカルボン酸塩部分を含むものとして得られるアミンはすべて、必要なモル量のNaOHで反応前に中和する。
この実施例は、他の3‐Dリガンドの使用を例解し、それは、細胞培地からのモノクローナル抗体並びに血漿及び血漿画分からのポリクローナル抗体の単離及び精製に特に有用であることがわかった。それは以下の式XV:
この実施例は、芳香族、疎水性、陽性、及び極性の4つの広いアミンのクラスにグループ分けされたアミンを使用した「ライブラリーのライブラリー」のコンビナトリアル合成を例解する。表4に詳解されたアミンY1、Y2及びY3を用いて、12のライブラリーのそれぞれを、実施例1〜7において記載されたライブラリーと同一の方法で合成した。
この実施例は、その合成方法が実施例9に記載された「ライブラリーのライブラリー」の、Cohn IV-Iペーストからの(アルファ‐1‐プロテイナーゼ阻害剤としても知られる)アルファ‐1‐アンチトリプシンタンパク質の結合のスクリーニングにおける使用を記載する。Cohn-IV-Iペーストを−80℃で凍結したペースト(20g)を、25℃の水浴中で一夜連続的に攪拌しながら15mMのリン酸ナトリウム緩衝液、pH8.1(300mL)に溶解することによって調製した。そして、この混合物を25℃で15,000rpmで15分間遠心分離し、1.0mm及び0.45mmのフィルターを通してろ過した。一回分0.5mLの10mMトリス、20mMクエン酸ナトリウム、150mM塩化ナトリウム、pH7.5を4回ゲル床の一番上に添加することによって、エタノール保存剤を各ライブラリー中の各位置から洗い出した。20%エタノール保存剤と交換するように、各1回分を重力によってゲル中を流れさせた。そして、各ライブラリー要素の一番下を密封し、Cohn IV-Iペースト(0.25mL)の調製物を各ゲル床の一番上に添加し、平衡化されたゲルと混合した。ライブラリーを負荷したCohn-VI-Iとともに30分間インキュベートした。この後、ライブラリーを開封し、各ライブラリー要素からのフロースルー(FT)を個別に集めた。1回分0.25mLの10mMトリス、20mMクエン酸ナトリウム、150mM塩化ナトリウム、pH7.5で各ゲル床を3回洗浄して、未結合のタンパク質を除去した。洗浄画分(W)を各ライブラリー要素から個別に集めた。1回の溶出ステップにおいて、8M尿素、25mMトリス、150mM塩化ナトリウム、pH7.5を各ゲル床の一番上に添加し(3×0.25mL)、各ライブラリー要素からの溶出液(E)を個別に集めた。最後に、1mLの0.2M水酸化ナトリウム/30%イソプロパノールを含む、(ゲル上に結合して残ったいかなる物質も除去するように設計された)衛生化ステップ(San)を各ゲル床の一番上に加え、重力によって流れるようにし、個別に集めた。各ライブラリー要素からのFT及びE画分をSDS PAGEゲルに流し、FT画分中のアルファ‐1‐アンチトリプシンの消失及びE画分中でのアルファ‐1‐アンチトリプシンの出現を目で分析した。有望な候補中のアルファ‐1‐アンチトリプシンの存在又はアルファ‐1‐アンチトリプシンの消失もまた、比濁分析によって確認した。
スクリーニングされた768個のライブラリー要素から4つを選び、実施例1〜7においてライブラリー合成について記載されたのと同一の化学及びアッセイを用いて、個別に30mLスケールで合成した。これらの4つの樹脂のアミン組成(Y1、Y2、Y3)を表6に示す。アミンの番号は表5と同じである。
約10mL容量、及び高さ12cmのカラム(詳細は表7を参照のこと)をカラム4つ分の体積の10mMトリス、20mMクエン酸ナトリウム、150mM塩化ナトリウム、pH7.5を用いて平衡化した。実施例9に記載のとおりに調製したCohn IV-Iペースト(体積については表7を参照のこと)を50cmh-1の流速でカラムに導入した。負荷後、カラム4つ分の体積の10mMトリス、20mMクエン酸ナトリウム、150mM塩化ナトリウム、pH7.5を200cmh-1で用いて未結合のタンパク質を洗い出した。2つの溶出液を使用した:はじめはカラム4つ分の体積の100mMリン酸ナトリウム、20mMクエン酸ナトリウム、pH6.1、そして第二はカラム4つ分の体積の8M尿素、25mMトリス、150mM塩化ナトリウム、pH7.5である。それぞれを200cmh-1の流速で流す。
この実施例は、3つのトリアジン基及び4つの独立して可変なY基を含む「4次元」ライブラリーの合成を記載する。PuraBead支持マトリックスを、実施例1に記載のようにエポキシド‐活性化して最終的なエポキシド負荷が5.6ミリモル/安定化させたゲルのgとし、そして実施例5に記載のスペーサー付加に類似の方法でエチレンジアミンを使用してエポキシド樹脂を処理することによってスペーサーX1を取り込ませた。
Claims (14)
- 2以上のトリアジン環、及び3個の独立したY基を含む、請求項1に記載の化合物。
- 3以上のトリアジン環、及び4個の独立したY基を含む、請求項1に記載の化合物。
- 各ZがYである、請求項4に記載の化合物。
- 各Xが、ジアミノアルカンスペーサーである、請求項1〜5のいずれか1項に記載の化合物。
- 各Yが、場合により置換された脂肪族及び芳香族一級アミンから独立して選ばれる、請求項1〜6のいずれか1項に記載の化合物。
- 共通の支持体M上の、請求項1〜8のいずれか1項に記載の化合物のライブラリー。
- 請求項9に記載のライブラリーの生成方法であって、中間体構造を一つ又は複数合成するステップ、上記構造をより小さな部分に分割するステップ、及び好適なその後の反応ステップを含む、前記方法。
- ペプチド及びタンパク質の分離、単離、精製、特徴づけ、同定、定量又は発見のための、請求項1〜8のいずれか1項に記載の化合物の使用。
- タンパク質様物質の分離、精製、又は発見のための方法であって、上記物質を含む試料を、請求項1〜8のいずれか1項に記載の化合物を用いるアフィニティークロマトグラフィーにかけることを含む、前記方法。
- 上記タンパク質様物質が、天然又は組換えの供給源由来の融合タンパク質を含む、イムノグロブリン或いはそのサブクラス、断片、前駆体又は誘導体である、請求項12に記載の方法。
- 請求項1〜8のいずれか1項に記載の化合物を用いて、生物学的化合物又は医薬化合物の調製物から、毒性又は病原性の物質を含む夾雑物を除去する方法。
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GBGB0228724.1A GB0228724D0 (en) | 2002-12-09 | 2002-12-09 | Multidimensinal libraries |
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PCT/GB2003/005368 WO2004052870A1 (en) | 2002-12-09 | 2003-12-09 | Triazine compounds and their use in forming multidimensional libraries for affinity chromatography |
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GB0416699D0 (en) | 2004-07-27 | 2004-09-01 | Prometic Biosciences Ltd | Prion protein ligands and methods of use |
EP1869230B1 (en) * | 2005-03-23 | 2017-08-30 | Bio-Rad Laboratories, Inc. | Method for purifying proteins |
MY144344A (en) | 2005-04-08 | 2011-09-15 | Ciba Holding Inc | Adsorbents comprising anthraquinone dye-ligands for the separation of biological materials |
GB0509442D0 (en) * | 2005-05-09 | 2005-06-15 | Prometic Biosciences Ltd | Affinity adsorbents for fibrinogen |
US8501939B2 (en) | 2005-06-10 | 2013-08-06 | Prometic Biosciences Limited | Triazines and pyrimidines as protein binding ligands |
US20080220968A1 (en) * | 2005-07-05 | 2008-09-11 | Ge Healthcare Bio-Sciences Ab | [1, 2, 4] Triazolo [1, 5-A] Pyrimidine Derivatives as Chromatographic Adsorbent for the Selective Adsorption of Igg |
US20070098676A1 (en) * | 2005-08-10 | 2007-05-03 | Simanek Eric E | Functionally diverse macromolecules and their synthesis |
EP2918641A1 (en) | 2014-03-13 | 2015-09-16 | Basf Se | Method for purification of antibodies, antibody fragments or engineered variants thereof using specific anthraquinone dye-ligand structures |
FR3040994B1 (fr) * | 2015-09-10 | 2019-07-26 | Arkema France | Composes etheramines et son utilisation en tant que collecteur de flottation |
JP2022546901A (ja) * | 2019-09-05 | 2022-11-10 | バイオ-ラッド・ラボラトリーズ・インコーポレーテッド | アニオン交換-疎水性混合モードクロマトグラフィー樹脂 |
GB2609185A (en) | 2021-05-24 | 2023-02-01 | Astrea Uk Services Ltd | Scaffold for isolation of a biomolecule |
CN114100584A (zh) * | 2021-11-23 | 2022-03-01 | 赣江中药创新中心 | 三嗪基键合色谱固定相及其制备方法 |
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GB2053926B (en) * | 1979-07-20 | 1983-02-23 | Atkinson A | Albumin extraction by affinity chromatography |
DE3379050D1 (en) * | 1982-08-11 | 1989-03-02 | Ciba Geigy Ag | Process for the chemical bond between a stabilising compound and a polymer |
DE3475918D1 (en) * | 1983-03-16 | 1989-02-09 | Ciba Geigy Ag | Azo compounds |
US4623625A (en) | 1983-04-21 | 1986-11-18 | La Trobe University | Enzyme extraction and purification processes |
DE3440777C2 (de) * | 1983-11-14 | 1998-09-03 | Clariant Finance Bvi Ltd | Neue sulfonsäuregruppenhaltige, basische Azoverbindungen, deren Herstellung und Verwendung als Farbstoffe |
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GB9519197D0 (en) * | 1995-09-20 | 1995-11-22 | Affinity Chromatography Ltd | Novel affinity ligands and their use |
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GB9910807D0 (en) * | 1999-05-10 | 1999-07-07 | Prometic Biosciences Limited | Novel detoxification agents and their use |
GB9929318D0 (en) | 1999-12-10 | 2000-02-02 | Prometic Biosciences Limited | Macrocyclic compounds and their use |
ITMI20012598A1 (it) * | 2001-12-11 | 2003-06-11 | 3V Sigma Spa | Hals macromolecolari a peso molecolare definito |
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GB0228724D0 (en) | 2003-01-15 |
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NZ541088A (en) | 2009-05-31 |
ATE526317T1 (de) | 2011-10-15 |
AU2003288447A1 (en) | 2004-06-30 |
US7723335B2 (en) | 2010-05-25 |
MXPA05006047A (es) | 2005-11-17 |
CA2508452C (en) | 2014-08-12 |
DK1569918T3 (da) | 2011-11-28 |
EP1569918A1 (en) | 2005-09-07 |
EP1569918B1 (en) | 2011-09-28 |
AU2003288447B2 (en) | 2008-02-21 |
US20060052598A1 (en) | 2006-03-09 |
CA2508452A1 (en) | 2004-06-24 |
JP2006519764A (ja) | 2006-08-31 |
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