JP6246230B2 - インプリントポリマーおよびその製造方法 - Google Patents
インプリントポリマーおよびその製造方法 Download PDFInfo
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- JP6246230B2 JP6246230B2 JP2015548869A JP2015548869A JP6246230B2 JP 6246230 B2 JP6246230 B2 JP 6246230B2 JP 2015548869 A JP2015548869 A JP 2015548869A JP 2015548869 A JP2015548869 A JP 2015548869A JP 6246230 B2 JP6246230 B2 JP 6246230B2
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- polymer
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- redox probe
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- monomer
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- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 238000004832 voltammetry Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- UXUXNGMSDNTZEC-UHFFFAOYSA-N zethrene Chemical compound C1=CC(C=2C(C=3C=CC=C4C=CC=C(C=2)C4=3)=C2)=C3C2=CC=CC3=C1 UXUXNGMSDNTZEC-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
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- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
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- B01D15/3852—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36 using imprinted phases or molecular recognition; using imprinted phases
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- 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
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
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- C08F2/00—Processes of polymerisation
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- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
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- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
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- C08F234/00—Copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain and having one or more carbon-to-carbon double bonds in a heterocyclic ring
- C08F234/02—Copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain and having one or more carbon-to-carbon double bonds in a heterocyclic ring in a ring containing oxygen
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Description
−光学ソリューション(optical solution)は、概して非常に高感度であり、ノイズ/信号比(noise/signal ratio)が大きいために小型化するのが困難である(非特許文献3、4)。
−圧電手段は、液状媒体中で分析を行う場合に使用するには依然として問題が多い(非特許文献5)。
−電気化学センサは、それらに関する限り、ノイズ/信号比が小さいために感度の損失なく小型化が可能であるという利点を呈する。更に、製造コストが低い。しかしながら、複雑なマトリクスの場合、それらを分析し得るには、検体を認識するための特定部位を電気化学センサに導入してその検出および/または定量を向上させる必要があり、これに関連して、分子インプリント電気化学センサ(非特許文献6)およびイオンインプリント電気化学センサ(非特許文献7)が開発されている。
−第一手段では、架橋剤を含まない導電性ポリマー内にインプリントが生成される。導電性ポリマーは認識とトランスデューサ(transducer)の2つの役割を有しており、認識の現象は測定可能な電気信号に変換される。この手段は多数の利点、とりわけ、使用しやすさ、電界生成フィルムの厚さ制御および所与の表面上に検出系を精密に被着させる可能性、を呈する(非特許文献10)。にもかかわらず、それらの使用には電気化学的測定の適用が含まれ、その結果として、例えば、導電性ポリマー内での対イオンの進入/退去が起こり得る。特にポリマー網状体が架橋していない結果として、これらの測定は、インプリントに、そして最終的には、標的を特異的に追跡するセンサの能力に、有害な影響を及ぼす。
−第二手段では、MIPおよびトランスデューサは別個の要素である。この手段は、導電性ポリマーであり得る導電相(非特許文献11)または炭素ペーストをベースとする電極(非特許文献12)内に、事前に調製および架橋されたMIPまたはIIP粒子を配合することからなる。この場合、インプリントを変性させる危険性は低下するが、標的を追跡したMIPまたはIIPと、電極の導電相との間の情報の伝達がより困難になるという不利な点がある。
0個の重合部位を有する場合、重合可能でない形態で存在し、
1つの重合部位を有する場合、重合可能な形態で存在し、モノマーとして作用し、または、
少なくとも2つの重合部位を有する場合、重合可能な形態で存在し、架橋剤として作用する、
化学的実体であり得る。
−アルキルは、少なくとも1つの炭素原子、好ましくは1〜30の炭素原子を有する飽和した直鎖または分岐鎖脂肪族炭化水素基を意味するものと理解される。有利には、用語「アルキル」は、1〜12の炭素原子、好ましくは1〜6の炭素原子を有する直鎖または分岐鎖脂肪族炭化水素基を示す。用語「分岐鎖」は、少なくとも1つの低級アルキル基、例えばメチルまたはエチルが線状アルキル鎖によって担持されることを意味する。アルキル基として、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、t−ブチルおよびn−ペンチル基などが挙げられる。
−アリールは、少なくとも1つの芳香環に由来する官能基または置換基を意味するものと理解される。芳香環は、非局在化π系を含む平坦な単環または多環基に相当し、ここで当該環の各原子はp軌道を含み、p軌道は互いに重なり合っている。
(i)標的および重合可能な形態または重合可能でない形態のいずれかで提供されるレドックスプローブの存在下で架橋剤とモノマーを重合する工程であって、前記レドックスプローブが重合可能な形態で存在するときには前記モノマーが前記レドックスプローブであることができ、レドックスプローブが2つ以上の重合可能部位を呈するときには前記架橋剤が前記レドックスプローブであることができる、工程と、
(ii)工程(i)の終わりに得られたポリマー内に存在する該標的を除去する工程と
を含む方法である。
(i’)標的を含むサンプルを本発明に従って規定されるようなインプリントポリマーと接触させる工程と、
(ii’)好ましくは電気的測定(導電性、インピーダンス)によってまたは電気化学的方法(クロノポテンショメトリ(chronopotentiometry)、クロノアンペロメトリもしくはボルタンメトリ(voltammetry))によって、該標的を検出する工程と
を少なくとも含む。
センサとして、好ましくはインプリントセンサとして、より具体的には分子および/またはイオンの検出分野におけるセンサ内の認識領域として、
(バイオ)センサを製造するための活性インターフェースとして、
分子およびイオンの固相抽出用カラムを製造するための固相抽出支持体として、
クロマトグラフィーのために、
疑似免疫測定(pseudo−immunoassay)のために、
人工抗体を製造するために、
エナンチオマーを分離するために、
有機合成のために、
触媒作用のために、
使用可能である。
本発明の分子インプリントポリマー(MIP)は、多環芳香族炭化水素(PAH)、ベンゾ[a]ピレン(BaP)のファミリーから選択される標的の存在下、ビニルフェロセン(VFc)(レドックスモノマー)とエチレングリコールジメタクリレート(EDMA)(架橋剤)から調製される(スキーム1)。
本発明のインプリントポリマーは、蒸留−沈殿重合によって調製される(F.Bai et al.,Macromolecules,2004,Vol.37,9746−9752)。
[(1). 赤外線分析]
分子インプリントポリマーMIP6および非インプリントポリマーNIP6を赤外線(Nexus−ThermoNicolet装置)で特性決定する。サンプルをKBrペレットの形態で調製する。MIP6およびNIP6のFTIRスペクトルをポリEDMAおよびフェロセンのFTIRスペクトルと比較することにより、EDMAをベースとするポリマーマトリクス中にVFcレドックスプローブが正しく配合されたことを実証することができる。EDMAおよびフェロセンのピーク特性はMIP6およびNIP6の両方にみられる(図3)。
MIP5/NIP5およびMIP6/NIP6ポリマーの粒子を走査電子顕微鏡法(SEM)(Gemini(登録商標)Supra 40VP装置)によって観察する。図4は、左側にMIP5ポリマー粒子(平均サイズ:2.45μm;変動係数:25%)を、右側にNIP5ポリマー粒子(平均サイズ:1.7μm;変動係数:39%)を示す。図5は、左側にMIP6ポリマー粒子(平均サイズ:1.5μm;変動係数:26%)を、右側にNIP6ポリマー粒子(平均サイズ:1.8μm;変動係数:45%)を示す。変動係数(CV)は、粒子サイズ分布に関する情報を与えるものであり、
すなわち、
CV(%)=(標準偏差×100)/平均サイズ(100個を超える粒子)
である。
[II−1. MIPの吸着特性:吸着等温線]
原理:
インプリントポリマーの標的分子(BaP)に関する吸着能力は、吸着等温線によって評価される。この方法は、既知量のポリマーを、標的分子を含む溶液と接触させ、ポリマーにより吸着される量を測定することからなる。吸着能力(結合能力、Qと表す)は、ポリマーにより吸着される標的分子の最大量(標的のmg(ミリグラム)/ポリマー樹脂のg(グラム)、または標的のμ(マイクロ)mol(モル)/ポリマー樹脂のg(グラム)で表す)である。この値は、インプリント効果を決定するべく非インプリントポリマーに関して得られる値と比較されるものである。
10mgのポリマーを30mLのガラスフラスコに導入する。その後、0.1mg.L−1から20.0mg.L−1までの間で様々である濃度を有する10mLのBaP溶液を加える。接触操作を24時間200rpmの速度でオービタルスターラを用いて行う。上澄みを0.45μmPTFEフィルターでろ過し、UV可視分光法によって分析して、ポリマーにより吸着されるBaP量を測定する。吸着量/ポリマーのg(グラム)を平衡濃度(上澄みの濃度)の関数としてプロットする。
[(1). トルエン中での吸着(Absorption)等温線(図6)]
合成されたMIP5ポリマーおよび対応するNIP5ポリマーのトルエン中での吸着等温曲線を図6に示す。図中、Ceは平衡でのBaP濃度を表す。
(一) 吸着能力は低BaP濃度で大幅に増大し、平衡濃度がBaPのおよそ5mg.L−1に達するとその最大値に到達すること。
(二) MIP5ポリマーの最大吸着能力は0.31±0.01mg.L−1であり、NIP5ポリマーの最大吸着能力は0.08±0.1mg.L−1であり、よって、本発明のインプリントポリマーは非インプリントポリマーよりも吸着能力が高いこと。
(三) MIP5/NIP5インプリント係数は3.9であり、よってMIP5ポリマーはNIP5ポリマーよりも3.9倍多くBaPを吸着すること。
本発明のインプリントポリマーの性能を、適用媒体と同様の媒体、すなわち水中で評価した。BaPはそれほど水に可溶性ではないため、試験は99/1(v/v)水/アセトニトリル混合物中で行う。
文献に提示された結果と本発明のMIP5ポリマーによって得られた結果を以下の表2において比較する。
[(1). 示差パルスボルタンメトリ(differential pulse voltammetry,DPV)による電気化学的試験]
原理:
示差パルスボルタンメトリ(differential pulse voltammetry,DPV)において、低振幅の線状電位勾配を、典型的には50ms(ミリ秒)の短期間、毎150〜200ms印加する。各パルスの印加直前および短期間(10〜20ms)の各パルスの直後に電流を測定する。記録された信号は、電位Eの関数としての、これら2つの測定間の電流差であり、結果として、ピークの出現を有する微分曲線が得られる。この技術により、ファラデー電流/容量性電流比が増大し得、故に感度が増大し得る。
初期電位 −0.100V
頂点電位 0.000V
最終電位 1.000V
パルス振幅 0.05V
パルス期間 50ms
高さ 1mV
期間 100ms
走査速度 0.01mV/秒
点の数 およそ2100
炭素ペーストを、MIP5ポリマーまたはNIP5ポリマーと、4:1の重量比で混合する。混合物を少量の溶媒(ジクロロメタン)で均質化する。混合物がかなり流動性である場合、中空の作用電極(メトローム電極)内に入れ、真空で乾燥させる。余剰分を、電極表面を研磨することによって取り除く。
作用電極 表面積0.070cm2の固体電極(炭素ペースト+ポリマー比4/1w/w電極)
参照電極 飽和塩化第一水銀電極(KCl:0.242V)
対電極 白金電極(直径1cm)
炭素ペースト/MIP5ポリマー(またはNIP5ポリマー)混合物を含む電極を、5mLの電界液(アセトニトリル中0.1mg.L−1のテトラブチルアンモニウムヘキサフルオロホスフェート)を含有する電気化学セル内に置く。フェロセンのレドックス信号を、両タイプの作用電極(MIP5ポリマーおよびNIP5ポリマー)について、およそ0.43Vで観察する(図8および図9)。この信号の安定化を得るには、4時間30分という正常な期間が必要である(作用電極と溶液との平衡のための時間)。4時間30分後、BaP標的を溶液に直接加え、次いで規則的な間隔で測定を行う。
「NIPのみ」は、4時間30分の安定化後の炭素ペースト中のNIP5ポリマーのボルタモグラムを表す。
「添加直後NIP+BaP」は、BaP標的添加直後に記録されたボルタモグラムを表す。
「0.5時間後NIP+BaP」は、BaP標的添加から30分後に記録されたボルタモグラムを表す。
炭素ペーストと混合したMIP5ポリマーを電極中に導入することによって同じ実験を行う。フェロセンのレドックス信号はおよそ0.43Vで観察される。
2つの特性、干渉分子の存在下での標的分子の吸着および感度を比較する。
吸着は、既知量のポリマーと既知濃度の標的の溶液とを接触させることによって行われる(吸着試験の場合にはBaPのみ、感度試験の場合にはBaP+別のPAH)。混合物を250rpmの速度でオービタルスターラにより撹拌する。5時間の接触時間の後、上澄みをHPLC−UVによって分析して、残存する各実体の量と吸着量を測定する。本試験で使用される8種のPAHをスキーム2に示す。
カラム Lichrospher(登録商標)PAH(5μm)(Merck KGaA)
検出器 Hitachi L−2455 DAD
オーブン温度 30℃
射出容量 50μL
流速 0.5ml/分
MIP6ポリマーを、1.25mg.L−1(すなわち、5μmol.L−1)に等しい濃度のBaP溶液と接触させる。接触時間の間、上澄みを分析する。およそ4時間(参照時間)の接触時間の後、吸着は最大かつ一定である(図10)。
BaP濃度の関数としての吸着の増大、次いでプラトー(plateau)が観察され、このプラトーは吸着能力(Q)に相当する(図11)。インプリント係数(非インプリントポリマーの吸着能力に対するインプリントポリマーの吸着能力の比)も測定する。MIP5、MIP6、NIP5およびNIP6ポリマーに関して得られる結果を表4に要約する。
上記で生成された等温線をモデル化して吸着現象を解釈することができる(E.Corton et al.,Journal of NonCrystalline Solids,2007,Vol.353,No.8−10,pp974−980;G.Limousin et al.,Applied Geochemistry,2007,Vol.22,No.2,pp249−275)。均一な吸着の場合、吸着パラメータを直接評価することができる。均一でない吸着の場合、評価は、低濃度での高アフィニティの吸着の寄与と高濃度での低アフィニティの吸着の寄与とを一般化することに基づく。最初の工程では、2つのモデル、単純なラングミュア(Langmuir)およびフロイントリッヒ(Freundlich)、を試験する。
このモデルは以下の5つの仮定に基づく。
仮定1: 吸着能力が最大値(Qmax)を有し得ること。
仮定2: 全ての部位が等価であること。
仮定3: 各部位が1つの分子だけに占有されること。
仮定4: エネルギーと立体障害が吸着量に依存しないこと。
仮定5: 表面活性係数が1に等しい(均一な吸着である)こと。
このモデルは、不均一な表面上での非理想的多層吸着に関する経験的関数、すなわち、
に基づくものであり、ここで、a=フロイントリッヒ吸着係数、m=不均一性指数(0<m<1)である。
およそ0.45μmol.L−1の各実体の濃度でBaPおよび他のPAHを含む溶液とポリマーを接触させることによって、選択性の測定を行い、吸着能力を測定する。
インプリントポリマーの電気化学特性を評価するために、MIP6およびNIP6ポリマーの粒子を導電性マトリクス(炭素ペースト)と混合し、次いでこの混合物を直径5mmの中空作用電極内に載置する。使用する技術は矩形波ボルタンメトリ(square wave voltammetry,SWV)である。
ポテンショスタット: ポテンショスタット/ガルバノスタットモデル273A(EG&G Princeton Applied Research社製)
30秒間0.000Vで平衡
初期電位 0.000V
頂点電位 1.000V
パルス振幅 0.15V
パルス期間 50ms
高さ 2mV
期間 100ms
走査速度 20mV/秒
Claims (22)
- 標的(インプリント実体)の存在下で少なくとも1つの架橋剤と少なくとも1つのモノマーを重合することによって得られ、前記標的の形状を有する少なくとも1つの空洞をその構造内に呈する非導電性インプリントポリマーであって、
重合可能な形態または重合可能でない形態のいずれかで提供される少なくとも1つのレドックスプローブをその構造内に含み、
前記インプリントポリマーは、該ポリマーの構造内に存在する前記レドックスプローブからなる伝達物質を含み、レドックスプローブ以外の他の伝達手段を含まない、非導電性インプリントポリマー。 - 前記レドックスプローブが少なくとも1つの重合可能部位を呈し、この場合のモノマーが前記レドックスプローブである、請求項1に記載のインプリントポリマー。
- 前記モノマーが、重合可能部位を有するフェロセン型の少なくとも1つの官能基を担持するレドックスモノマーである、請求項2に記載のインプリントポリマー。
- 前記レドックスモノマーがビニルフェロセンである、請求項3に記載のインプリントポリマー。
- 前記レドックスプローブが、少なくとも2つの重合可能部位を呈し、かつ、架橋剤として作用する、請求項1に記載のインプリントポリマー。
- 前記架橋剤が、二官能基、三官能基または四官能基から選択される(メタ)アクリル酸モノマー、ビニルモノマー、スチレンモノマーまたはアリルモノマーである、請求項5に記載のインプリントポリマー。
- 前記レドックスプローブが、標的の形状を有する前記空洞に近接して位置している、請求項1〜6の一項に記載のインプリントポリマー。
- 前記標的が分子またはイオンである、請求項1〜7のいずれか一項に記載のインプリントポリマー。
- 前記標的が、多環芳香族炭化水素(PAH)、ステロイド、活性成分、殺虫剤、除草剤、界面活性剤、食用色素または生物活性分子から選択される分子である、請求項8に記載のインプリントポリマー。
- 前記標的がイオンであり、前記ポリマーが重合可能な形態または重合可能でない形態のいずれかで提供される少なくとも1つのリガンドもその構造内に含むことができる、請求項8に記載のインプリントポリマー。
- 前記レドックスプローブと標的の形状を有する前記空洞との最小距離が、前記レドックスプローブが前記標的と相互作用しかつ検出信号を発する距離である、請求項1〜10のいずれか一項に記載のインプリントポリマー。
- 前記レドックスプローブが、標的の形状を有する前記空洞内に位置している、請求項11に記載のインプリントポリマー。
- 請求項1〜12の一項に記載のインプリントポリマーの調製方法であって、
(i)標的と、重合可能な形態または重合可能でない形態のいずれかで提供されるレドックスプローブとの存在下で、架橋剤とモノマーを重合する工程と、
(ii)工程(i)の終わりに得られたポリマー内に存在する前記標的を除去する工程と
を含む方法。 - 前記レドックスプローブが少なくとも1つの重合可能部位を呈し、この場合のモノマーがレドックスプローブである、請求項13に記載の方法。
- 前記レドックスプローブが少なくとも2つの重合可能部位を呈し、この場合の架橋剤が前記レドックスプローブである、請求項13に記載の方法。
- 前記工程(i)が蒸留−沈殿によって行われる、請求項13〜15のいずれか一項に記載の方法。
- 標的の検出方法であって、
(i’)標的を含むサンプルを請求項1〜12のいずれか一項に記載のインプリントポリマーと接触させる工程と、
(ii’)該標的を検出する工程と
を少なくとも含む方法。 - 前記検出工程(ii’)が、電気的測定または電気化学方法によって行われる、請求項17に記載の方法。
- 請求項1〜12のいずれか一項に記載のインプリントポリマーの、センサとしての使用。
- 請求項1〜12のいずれか一項に記載のインプリントポリマーの、(バイオ)センサまたは固相抽出支持体を製造するための活性インターフェースとしての使用。
- 請求項1〜12のいずれか一項に記載のインプリントポリマーを少なくとも1つ包含する装置。
- 前記装置が電気化学センサまたは抽出カラムである、請求項21に記載の装置。
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