JP4266377B2 - アニオン性置換基を有する物質の捕捉剤 - Google Patents
アニオン性置換基を有する物質の捕捉剤 Download PDFInfo
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- JP4266377B2 JP4266377B2 JP2005503096A JP2005503096A JP4266377B2 JP 4266377 B2 JP4266377 B2 JP 4266377B2 JP 2005503096 A JP2005503096 A JP 2005503096A JP 2005503096 A JP2005503096 A JP 2005503096A JP 4266377 B2 JP4266377 B2 JP 4266377B2
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- anionic substituent
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Images
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/0203—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of metals not provided for in B01J20/04
- B01J20/024—Compounds of Zn, Cd, Hg
- B01J20/0244—Compounds of Zn
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Description
{式中、Rは、相互に同一又は異なっていてもよく、水素原子;炭素数が1〜16であるアルキル基;アシル基、アルコキシカルボニル基、アシルアルキル基、アルコキシカルボニルアルキル基、カルボキシアルキル基、カルバモイルアルキル基、シアノアルキル基、ヒドロキシアルキル基、アミノアルキル基又はハロアルキル基(ここで、これらの基のアルキル部分の炭素数は、1〜16である);カルボキシル基;カルバモイル基;シアノ基;ヒドロキシル基;アミノ基;或いはハロゲノ基である}で示される亜鉛錯体基が直接又はスペーサーを介して結合したポリマー担体である。
や、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したArgoGel(登録商標):
や、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したTSKgel(登録商標):
や、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したSepharose(商標):
等を挙げることができる。
や、Zn2+−サイクレン基が結合したArgoGel(登録商標):
や、Zn2+−サイクレン基を結合したTentaGel(登録商標):
等を挙げることができる。
TOYOPEARL(登録商標) AF−Epoxy−650M 10gとサイクレン6.9gと炭酸カリウム2.2gのエタノール溶液75mLを、40℃で4日間撹拌した。反応液を濾過洗浄した後、得られたビーズと硝酸亜鉛六水和物12gの水溶液75mLを、40℃で2日間撹拌した。反応液を濾過洗浄した後、減圧乾燥を行うと、Zn2+−サイクレン基が結合したTOYOPEARL(登録商標)12g(0.3mmol Zn2+/g)が得られた。
ポリエチレン製のフィルターが付いたカラムに、Zn2+−サイクレン基が結合したTOYOPEARL(登録商標)100mg(0.3mmol Zn2+/g)を充填して、Zn2+−サイクレン基が結合したTOYOPEARL(登録商標)カラムを作製した。
Zn2+−サイクレン基が結合したTOYOPEARL(登録商標)カラムを、50mMトリス−塩酸緩衝液(pH 7.0)で膨潤させた。カラムに50mMトリス−塩酸緩衝液(pH 7.0)で調整した10mM 4−ニトロ安息香酸ナトリウム溶液1.0mLを添加し、その後50mMトリス−塩酸緩衝液(pH 7.0)2.0mLを添加し流出させた。流出液を収集し、紫外可視分光光度計を用いて流出液から1価の4−ニトロ安息香酸アニオンの捕捉率を測定したところ、100%であった。
Zn2+−サイクレン基が結合したTOYOPEARL(登録商標)カラムを、50mMトリス−塩酸緩衝液(pH 7.0)で膨潤させた。カラムに50mMトリス−塩酸緩衝液(pH 7.0)で調整した10mM 4−ニトロフェニルリン酸二ナトリウム溶液1.0mLを添加し、その後50mMトリス−塩酸緩衝液(pH 7.0)2.0mLを添加し流出させた。流出液を収集し、紫外可視分光光度計を用いて流出液から2価の4−ニトロフェニルリン酸アニオンの捕捉率を測定したところ、98%であった。
1,3−ジアミノ−2−プロパノール33gと2−ピリジンカルボキシアルデヒド116gとシアノトリヒドロほう酸ナトリウム50gのメタノール溶液500mLを、室温で3日間撹拌した。後処理をした後、カラムクロマトグラフィーで精製すると、合成中間体34gが得られた。
TOYOPEARL(登録商標) AF−Amino−650M 1.2gとN−(5−カルボキシ−2−ピリジル)メチル−N,N’,N’−トリス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロパノール450mgとジシクロヘキシルカルボジイミド210mgと1−ヒドロキシベンゾトリアゾール150mgのN,N−ジメチルホルムアミド溶液10mLを、40℃で18時間撹拌した。反応液を濾過洗浄した後、得られたビーズと酢酸亜鉛二水和物480mgと10M水酸化ナトリウム水溶液0.10mLのエタノール溶液7.0mLを、40℃で18時間撹拌した。反応液を濾過洗浄した後、得られたビーズと1.0M過塩素酸ナトリウム水溶液3.0mLの水溶液7.0mLを、40℃で18時間撹拌した。反応液を濾過洗浄した後、減圧乾燥を行うと、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したTOYOPEARL(登録商標)1.0g(0.5mmol Zn2+/g)が得られた。
ポリエチレン製のフィルターが付いたカラムに、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したTOYOPEARL(登録商標)100mg(0.5mmol Zn2+/g)を充填して、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したTOYOPEARL(登録商標)カラムを作製した。
Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したTOYOPEARL(登録商標)カラムを、50mMトリス−塩酸緩衝液(pH 7.0)/アセトニトリル(1/1)溶液で膨潤させた。カラムに50mMトリス−塩酸緩衝液(pH 7.0)/アセトニトリル(1/1)溶液で調整した10mM 4−ニトロ安息香酸ナトリウム溶液1.0mLを添加し、その後50mMトリス−塩酸緩衝液(pH 7.0)/アセトニトリル(1/1)溶液2.0mLを添加し流出させた。流出液を収集し、紫外可視分光光度計を用いて流出液から1価の4−ニトロ安息香酸アニオンの捕捉率を測定したところ、100%であった。続いて、50mMリン酸緩衝液(pH 3.0)/アセトニトリル(1/1)溶液50mLを添加し流出させた。流出液を収集し、紫外可視分光光度計を用いて流出液から1価の4−ニトロ安息香酸アニオンの回収率を測定したところ、100%であった。
Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したTOYOPEARL(登録商標)カラムを、50mMトリス−塩酸緩衝液(pH 7.0)で膨潤させた。カラムに50mMトリス−塩酸緩衝液(pH 7.0)で調整した10mM 4−ニトロフェニルリン酸二ナトリウム溶液1.0mLを添加し、その後50mMトリス−塩酸緩衝液(pH 7.0)2.0mLを添加し流出させた。流出液を収集し、紫外可視分光光度計を用いて流出液から2価の4−ニトロフェニルリン酸アニオンの捕捉率を測定したところ、100%であった。続いて、溶離液として50mMリン酸緩衝液(pH 3.0)50mLを添加し流出させ、流出液を収集し、紫外可視分光光度計を用いて流出液から2価の4−ニトロフェニルリン酸アニオンの回収率を測定したところ、89%であったが、溶離液として50mMトリス−塩酸酸緩衝液(pH 7.0)50mLを添加し流出させ、流出液を収集し、紫外可視分光光度計を用いて流出液から2価の4−ニトロフェニルリン酸アニオンの回収率を測定したところ、0%であった。
1,3−ジアミノ−2−プロパノール33gと2−ピリジンカルボキシアルデヒド116gとシアノトリヒドロほう酸ナトリウム50gのメタノール溶液500mLを、室温で3日間撹拌した。後処理をした後、カラムクロマトグラフィーで精製すると、合成中間体34gが得られた。
メチルエステル体10gとエチレンジアミン23gのメタノール溶液100mLを、室温で3日間撹拌した。後処理をした後、カラムクロマトグラフィーで精製すると、N−{5−[N−(2−アミノ)エチル]カルバモイル−2−ピリジル}メチル−N,N’,N’−トリス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロパノール10gが得られた。
NHS−activated Sepharose(商標) 4FFの20mMアセトニトリル溶液5.0mLとN−{5−[N−(2−アミノ)エチル]カルバモイル−2−ピリジル}メチル−N,N’,N’−トリス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロパノールの5.0mMアセトニトリル溶液5.0mLを、50℃で1時間撹拌した。反応液を濾過洗浄した後、20mM炭酸ナトリウム水溶液で洗浄すると、N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロパノール基が結合したSepharose(商標)5.0mLが得られた。
ポリプロピレン製のフィルターが付いたカラムにN,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロパノール基が結合したSepharose(商標)1.0mLを充填し、100mM 2−(N−モルホリノ)エタンスルホン酸(MES)緩衝液(pH6.0)と20mM酢酸亜鉛水溶液の混合溶液5.0mL、100mM 2−(N−モルホリノ)エタンスルホン酸(MES)緩衝液(pH6.0)と0.1mM酢酸亜鉛水溶液の混合溶液5.0mL、トリス−塩酸緩衝液(pH 7.0)と0.5M塩化ナトリウム水溶液の混合溶液5.0mLで平衡化させて、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したSepharose(商標)カラムを作製した。
Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したSepharose(商標)カラムに、ウシ血清アルブミン(分子量66,000 リン酸化セリン残基×0)50μgとニワトリ卵白アルブミン(分子量45,000 リン酸化セリン残基×2)50μgとウシαS1−カゼイン(分子量24,000 リン酸化セリン残基×8)50μgとウシαS1−カゼイン非リン酸化型(分子量24,000 リン酸化セリン残基×0)50μgとウシβ−カゼイン(分子量25,000 リン酸化セリン残基×5)50μgを添加した。続いて、トリス−塩酸緩衝液(pH 7.0)と0.5M塩化ナトリウム水溶液の混合溶液1.0mLを2回、トリス−酢酸緩衝液(pH 7.0)1.0mLを4回、10mMリン酸緩衝液(pH 7.0)1.0mL、15mMリン酸緩衝液(pH 7.0)1.0mL、20mMリン酸緩衝液(pH 7.0)1.0mL、25mMリン酸緩衝液(pH 7.0)1.0mL、30mMリン酸緩衝液(pH 7.0)1.0mL、35mMリン酸緩衝液(pH 7.0)1.0mL、40mMリン酸緩衝液(pH 7.0)1.0mL、45mMリン酸緩衝液(pH 7.0)1.0mL、50mMリン酸緩衝液(pH 7.0)1.0mL、60mMリン酸緩衝液(pH 7.0)1.0mL、70mMリン酸緩衝液(pH 7.0)1.0mL、80mMリン酸緩衝液(pH 7.0)1.0mL、90mMリン酸緩衝液(pH 7.0)1.0mL、100mMリン酸緩衝液(pH 7.0)1.0mL、200mMリン酸緩衝液(pH 7.0)1.0mL、300mMリン酸緩衝液(pH 7.0)1.0mL、400mMリン酸緩衝液(pH 7.0)1.0mL、500mMリン酸緩衝液(pH 7.0)1.0mLの順に添加し流出させた。流出液を濃縮した後にスポットし、ドデシル硫酸ナトリウム−ポリアクリルアミドゲル電気泳動(SDS−PAGE)で分離した後、クマシーブリリアントブルー(CBB)染色した。電気泳動図の前半を図1、後半を図2に示す。図1及び図2において、始めにリン酸化セリン残基を有さないウシ血清アルブミン、続いてリン酸化セリン残基の数が少ない順に、ニワトリ卵白アルブミン、ウシβ−カゼイン、ウシαS1−カゼインの流出が確認できた。
マイクロピペットチップにセルロース製のフィルターを詰め、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したSepharose(商標)カラムから取り出した、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したSepharose(商標)10μLを充填し、その後セルロース製のフィルターで蓋をして、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したSepharose(商標)チップを作製した。
Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したSepharose(商標)チップを取りつけたマイクロピペットで、0.50M硝酸ナトリウム含有100mMトリス−酢酸緩衝液(pH7.4)で調整した0.22mM p60c−srcペプチド521−533と0.18mMリン酸化p60c−srcペプチド521−533の混合溶液10μLを吸入し、5分間平衡化させた後、吐き出した。その後、0.50M硝酸ナトリウム含有100mMトリス−酢酸緩衝液(pH7.4)10μLで5回洗浄した。続いて、10mMリン酸緩衝液(pH7.0)10μLで6回洗浄し、洗液を収集して、高速液体クロマトグラフィーを用いて純度を測定したところ、リン酸化p60c−srcペプチド521−533が100%、p60c−srcペプチド521−533が0%であった。
PS20 ProteinChip(登録商標) Arrayに、100mM炭酸水素ナトリウム水溶液/アセトニトリル(1/3)溶液で調整した0.38M N−{5−[N−(2−アミノ)エチル]カルバモイル−2−ピリジル}メチル−N,N’,N’−トリス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロパノール溶液3.0μLを載せ、室温で4時間反応した。更に、100mM炭酸水素ナトリウム水溶液で調整した0.50M 2−アミノエタノール溶液3.0μLを載せ、室温で4時間反応した。洗浄した後、100mM 2−(N−モルホリノ)エタンスルホン酸(MES)緩衝液(pH6.0)で調整した0.50M酢酸亜鉛溶液で洗浄すると、Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したProteinChip(登録商標) Arrayが得られた。
Zn2+ 2−N,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロポキシド基が結合したProteinChip(登録商標) Arrayに、100mMトリス−酢酸緩衝液(pH7.4)で調整した0.94mM 4−メチルウンベリフェリルリン酸二ナトリウム溶液3.0μLを載せ、室温で1時間平衡化させた後、回収した。回収液を収集し、紫外可視分光光度計を用いて回収液から2価の4−メチルウンベリフェリルリン酸アニオンの捕捉率を測定したところ、16%であった。
ポリエチレン製のフィルターが付いたカラムにTOYOPEARL(登録商標) AF−Epoxy−650M 100mgを充填し、50mMトリス−塩酸緩衝液(pH 7.0)で膨潤させた。カラムに50mMトリス−塩酸緩衝液(pH 7.0)で調整した10mM 4−ニトロフェニルリン酸二ナトリウム溶液1.0mLを添加し、その後50mMトリス−塩酸緩衝液(pH 7.0)2.0mLを添加し流出させた。流出液を収集し、紫外可視分光光度計を用いて流出液から2価の4−ニトロフェニルリン酸アニオンの捕捉率を測定したところ、0.5%であった。
ポリプロピレン製のフィルターが付いたカラムにN,N,N’,N’−テトラキス[(2−ピリジル)メチル]−1,3−ジアミノ−2−プロパノール基が結合したSepharose(商標)1.0mLを充填し、トリス−塩酸緩衝液(pH 7.0)と0.5M塩化ナトリウム水溶液の混合溶液5.0mLで平衡化させた。カラムにウシ血清アルブミン(分子量66,000 リン酸化セリン残基×0)50μgとニワトリ卵白アルブミン(分子量45,000 リン酸化セリン残基×2)50μgとウシαS1−カゼイン(分子量24,000 リン酸化セリン残基×8)50μgとウシαS1−カゼイン非リン酸化型(分子量24,000 リン酸化セリン残基×0)50μgとウシβ−カゼイン(分子量25,000 リン酸化セリン残基×5)50μgを添加した。続いて、トリス−塩酸緩衝液(pH 7.0)と0.5M塩化ナトリウム水溶液の混合溶液1.0mLを2回、トリス−酢酸緩衝液(pH 7.0)1.0mLを4回、10mMリン酸緩衝液(pH 7.0)1.0mL、15mMリン酸緩衝液(pH 7.0)1.0mL、20mMリン酸緩衝液(pH 7.0)1.0mL、25mMリン酸緩衝液(pH 7.0)1.0mL、30mMリン酸緩衝液(pH 7.0)1.0mL、35mMリン酸緩衝液(pH 7.0)1.0mL、40mMリン酸緩衝液(pH 7.0)1.0mL、45mMリン酸緩衝液(pH 7.0)1.0mL、50mMリン酸緩衝液(pH 7.0)1.0mL、60mMリン酸緩衝液(pH 7.0)1.0mL、70mMリン酸緩衝液(pH 7.0)1.0mL、80mMリン酸緩衝液(pH 7.0)1.0mL、90mMリン酸緩衝液(pH 7.0)1.0mL、100mMリン酸緩衝液(pH 7.0)1.0mL、200mMリン酸緩衝液(pH 7.0)1.0mL、300mMリン酸緩衝液(pH 7.0)1.0mL、400mMリン酸緩衝液(pH 7.0)1.0mL、500mMリン酸緩衝液(pH 7.0)1.0mLの順に添加し流出させた。流出液を濃縮した後にスポットし、ドデシル硫酸ナトリウム−ポリアクリルアミドゲル電気泳動(SDS−PAGE)で分離した後、クマシーブリリアントブルー(CBB)染色した。電気泳動図の前半を図3、後半を図4に示す。図3及び図4において、始めからウシ血清アルブミン、ニワトリ卵白アルブミン、ウシβ−カゼイン、ウシαS1−カゼインの流出が確認できた。
Claims (9)
- 請求の範囲第1項記載のポリマー担体を含有する、アニオン性置換基を有する物質の捕捉剤。
- アニオン性置換基がリン酸基である、請求の範囲第2項記載の捕捉剤。
- 捕捉剤がビーズの形態である、請求の範囲第2項記載又は第3項記載の捕捉剤。
- 捕捉剤がプレートの形態である、請求の範囲第2項記載又は第3項記載の捕捉剤。
- 捕捉剤が繊維の形態である、請求の範囲第2項記載又は第3項記載の捕捉剤。
- 請求の範囲第2項〜第4項又は第6項のいずれか一項記載の捕捉剤を充填し、フィルターで濾別する機能を持つ、アニオン性置換基を有する物質の捕捉器具。
- アニオン性置換基を有する物質を、請求の範囲第2項〜第6項のいずれか一項記載の捕捉剤に結合させることによって捕捉する工程を含む、アニオン性置換基を有する物質の捕捉方法。
- 該捕捉工程の後、アニオン性置換基を有する物質を捕捉剤から解離させる工程を更に含む、請求の範囲第8項記載の方法。
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