JP4112499B2 - 複素環窒素を含む重合体からなるバイオセンサ・メンブラン - Google Patents
複素環窒素を含む重合体からなるバイオセンサ・メンブラン Download PDFInfo
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Description
本発明の重合体は、次の一般式,式1aを有し、
[表1]反応基、および得られる結合の例
例えば、Aは、6−ブロモヘキサン酸を用いて複素環窒素を4級化し、続いてカルボジイミド結合剤の存在下で3−アミノ−1−プロパンスルホネートのアミン基にカルボキシ基を結合してAを重合体の複素環窒素基に結合することができる。
以下、本発明による種々のポリビニルピリジン重合体の合成例を示す。数値は概略の値である。
実例として、上記式3の重合体の合成例を提示する。ポリ(4−ビニルピリジン−co−スチレン)溶液(スチレン含有量約10%)(20g、アルドリッチ)を100mLのジメチルホルムアミド(DMF)中90℃で撹拌し、次いで6−ブロモヘキサン酸(3.7g)と15〜20mLのDMFの溶液を加えた。得られた溶液を90℃で24時間撹拌し、次いで1.5Lのエーテルに注入し、生成物から溶媒を移した。残りのゴム状固体をMeOH(150〜200mL)に溶解し、中間サイズの孔のあるフリットガラス漏斗で溶液を吸引ろ過し、未溶解の固体を除去した。ろ液をビーカー中のエーテル(1.5L)に撹拌しながら初めはゆっくりと入れ、次いで次第に速く入れた。得られた沈殿物を吸引ろ過により集め、高真空下、50℃で2日間乾燥した。重合体のパラメータは、[n/(n+l+p)]×100%≒10%、[l/(n+l+p)]×100%≒80%、および[p/(n+l+p)]×100%≒10%であった。
実例として、上記式5の重合体の合成例を提示する。ポリ(4−ビニルピリジン−co−スチレン)溶液(スチレン含有量約10%)(20g、アルドリッチ)を100mLの無水DMF中90℃で撹拌し、スルホン酸メタン(約80mg)を加え、次いで15〜20mLの無水DMF中2gのメトキシ−PEG−エポキシド(分子量5,000)(シェアウォーター・ポリマーズ・インコーポレイテッド (Shearewater Polymers, Inc.) )を加えた。得られた溶液を90℃で24時間撹拌し、10mLの無水DMF中1、3−プロパンスルトン(2.32g)を加えた。溶液を連続的に90℃で24時間撹拌し、次いで室温まで冷却し、800mLのエーテルに注入した。溶媒を移し、残りの沈殿をホットMeOH(約200mL)に溶解し、吸引ろ過し、1Lのエーテルから再度沈殿させ、高真空下50℃で48時間乾燥した。得られた重合体のパラメータは、[n/(n+m+l+p)]×100%≒10%、[m/(n+m+l+p)]×100%≒10%、[l/(n+m+l+p)]×100%≒70%、および[p/(n+m+l+p)]×100%≒10%であった。
実例として、以下に概略図として示したポリヒドロキシ変性剤Bを有する重合体の合成の実施例を提示する。生物適合性を有する種々のポリヒドロキシ化合物が知られている。(米国特許第6,011,077号(特許文献10))次の合成図は、望ましい特性を有する変性剤基を結合剤を介して重合体主鎖に結合する方法を説明している。
1,3−プロパンスルトン(0.58g、4.8ミリモル)および6−ブロモヘキサン酸(1.85g、9.5ミリモル)を、60mLの無水DMFに溶解したポリ(4−ビニルピリジン−co−スチレン)(スチレン約10%)(10g)の溶液に添加する。得られた溶液を90℃で24時間撹拌し、次いで室温まで冷却する。O−(N−サクシンイミジル)−N,N,N’,N’−テトラメチル−ウロニウム テトラフロロボレート(TSTU)(2.86g、9.5ミリモル)およびN,N−ジイソプロピルエチルアミン(1.65mL、9.5ミリモル)を溶液に連続的に添加する。この溶液を5時間撹拌後、N−メチル−D−グルカミン(2.4g、12.4ミリモル)を添加し、得られた溶液を室温で24時間撹拌する。この溶液を500mLのエーテルに注入し、吸引ろ過により沈殿物を集める。次いで、集めた沈殿物をMeOH/H2Oに溶解し、得られた溶液を同じMeOH/H2Oを用いて限外メンブランろ過にかけて小さな分子を除去する。透析した溶液を蒸発乾燥して、次のパラメータ、[n/(n+m+l+p)]×100%≒10%、[m/(n+m+l+p)]×100%≒10%、[l/(n+m+l+p)]×100%≒70%、および[p/(n+m+l+p)]×100%≒10%を有する重合体を得る。
本発明の架橋剤は、ビー、トリー、またはテトラー官能基などの少なくとも2つの反応基を有する分子であり、複素環窒素基、ピリジン基、または重合体のA、BまたはDを含むその他の反応基と反応しうる。好ましくは、架橋剤の反応基は、ゆっくり反応するアルキル化基であり、これらは重合体のピリジン基などの複素環窒素基を4級化することができる。適当なアルキル化剤には、ポリ(エチレングリコール)またはポリ(プロピレングリコール)の誘導体、エポキシド(グリシジル基)、アジリジン、ハロゲン化アルキル、およびスルホン酸エステルがあるが、これらに限定されるものではない。架橋剤のアルキル化基は、好ましくはグリシジル基である。好ましくは、グリシジル架橋剤の分子量は、約200〜約2,000で、且つ水溶性またはアルコールなどの水と混和する溶媒に可溶である。適当な架橋剤の例には、分子量約200〜約600のポリ(エチレングリコール)ジグリシジルエーテルやN,N−ジグリシジル−4−グリシジルオキシアニリンがあるが、これらに限定されるものではない。
メンブラン溶液の調合中、架橋反応を遅くするように、メンブランコーティング溶液は大規模生産の場合ポットライフが適度であることが望ましい。架橋反応が速いと、コーティング溶液の粘度が急速に変化し、コーティングを困難にする。理想的には、架橋反応はメンブラン溶液の調合中は遅く、常温または常温より高い温度ではメンブランの硬化中加速する。
本発明のメンブラン製造プロセスの実施例について説明する。この実施例では、本発明の重合体および適切な架橋剤が、緩衝剤含有溶媒、通常、緩衝剤混合アルコール溶媒に溶解され、メンブラン溶液をつくる。好ましくは、この緩衝剤のpHは約7.5〜約9.5であり、アルコールはエタノールである。より好ましくは、緩衝剤は10ミリモルの(2−(4−(2−ヒドロキシエチル)−1−ピペラジン)スルホン酸エタン)(HEPES)緩衝剤(pH8)であり、且つエタノールと緩衝剤の容積比は約95:5〜約0:100である。架橋の化学、特にエポキシドまたはアジリジン架橋剤が使われた場合は、最小量の緩衝剤が必要である。重合体と架橋剤を溶解するのに必要な溶媒の量は、重合体と架橋剤の特性によって変動する。例えば、相対的に疎水性である重合体および/または架橋剤を溶解するには高い割合のアルコールが必要である。
センサの製作は、通常、作用電極上への酵素含有感知層の堆積および感知層および好ましくは随意に対向兼参照電極上への拡散制限メンブラン層のキャスティングからなる。以下の手順は、図2A〜2Cに描かれた2電極からなるセンサの製作に関する。例えば、3電極からなるその他のセンサは、類似の方法を用いてつくることができる。
感知層溶液を炭素インク作用電極上に堆積し、室温で2日間硬化させ、多数のセンサをつくった。メンブラン溶液は、EtOH80%とHEPES緩衝剤(10mM、pH8)20%からなる溶液に64mg/mLにて溶解した上記式4の4容積の重合体を、エタノール80%とHEPES緩衝剤(10mM、pH8)20%からなる溶液に4mg/mLにて溶解したポリ(エチレングリコール)ジグリシジルエーテル(分子量200)の1容積を混合して調製した。上述したセンサをメンブラン溶液に10分間隔で1回に約5秒間3回浸漬した。次いで、このセンサを室温と普通の湿度で24時間硬化させた。
本発明の重合体にはピリジン基などの複素環窒素基があるが、メンブラン形成中に架橋に使われているのはその内の数%に過ぎない。したがって、このメンブランはメンブラン・マトリックス内とメンブラン表面の両方に存在する過剰のこれらの基がある。随意に、このメンブランは複素環窒素基に富むメンブラン表面またはピリジンに富むメンブラン表面にもう一つの物質層を置くことによりさらに変性することができる。例えば、メンブラン表面は、ポリ(エチレングリコール)の層を添加することにより生物適合性を高めることができる。一般に、変性は、アルキル化反応基を有する望ましい分子を含む溶液のような変性溶液でメンブラン表面をコーティングし、次いで過剰の分子を除去するために適当な溶媒でコーティング溶液を洗浄することからなる。この変性により望ましい分子の単層を生じる。
図2に示したグルコースセンサ10のメンブラン20は、上述した方法で変性することができる。
本発明による拡散制限メンブランを有するセンサの特性および/または有効性を示す実験例を以下に提示する。数値は近似的なものである。
第1の実施例では、較正実験を行った。この実験では、メンブランのない15個のセンサを同時にテスト(セット1)し、別に本発明による拡散制限メンブランを有する8個のセンサを同時にテスト(セット2)した。実験はすべて37℃で行った。セット2では、メンブランは、上記式4の重合体と約200の分子量を有するポリ(エチレングリコール)ジグリシジルエーテル(PEGDGE)架橋剤からつくった。セット1とセット2の各々に関する較正実験では、センサはPBS緩衝溶液(pH7)に置き、グルコース濃度を上げた時の各センサの出力電流を測定した。測定した出力電流(セット1のμA、セット2のnA)をセット1とセット2の各々について平均化し、次いで図3の較正グラフに示したようにグルコース濃度(mM)に対してプロットした。
第2の実施例では、安定性に関する実験を行った。この実験では、メンブランのないセンサと本発明による拡散制限メンブランを有するセンサを同時に37℃でテストした。メンブランを備えたセンサのメンブランは、較正実験において上述したセット2のセンサと同じ重合体および同じ架橋剤からつくられた。この安定性に関する実験では、各センサを30mMという固定したグルコース濃度を有するPBS緩衝溶液(pH7)に入れ、各センサの出力電流を測定した。測定した出力電流(メンブランのないセンサではμA、メンブランを備えたセンサではnA)は、図4の安定性グラフに示したように、時間(時間)に対してプロットした。
理想的には、電気化学センサのメンブランは、センサの感知層と検体を含む流体と生物流体の間の連通を妨害してはならない。すなわち、メンブランは検体の濃度変化に迅速に応答する。
理想的には、電気化学センサのメンブランは、検体を含む流体または生物流体の運動または動作の影響を受けてはならない。これは、人体などの生体に移植されているセンサの場合、生体の運動は頻繁に運動に関連したノイズを生じるので、特に重要である。
メンブランの浸漬コーティングやキャスティングは、通常、英国のNIMAテクノロジーのDSG DIL−160などの浸漬機械を用いて行う。メンブランのキャスティングを再現性よく作ることは困難であると考えられていた。(チェン,T.ら,「in situの組み立てられ質量輸送制御マイクロメンブランおよび移植された電流測定グルコースセンサにおけるマイクロメンブランの利用」,アナリティカル・ケミストリ,Vol.72,No.16,3757〜3763ページ (2000年) (Chen, T., et al., In Situ Assembled Mass-Transport Cocntrolling Micromembranes and Their Application Implanted in Amperometric Glucose Sensors), Anal. Chem., Vol. 72, No. 16, Pp. 3757-3763 (2000))(非特許文献11)驚いたことに、本発明のセンサは、次に説明する実験で証明されるように、非常に再現性よく作ることができる。
バッチ1:平均傾斜=1.10nA/mM(CV= 5%)
バッチ2:平均傾斜=1.27nA/mM(CV=10%)
バッチ3:平均傾斜=1.15nA/mM(CV= 5%)
バッチ4:平均傾斜=1.14nA/mM(CV= 7%)
さらに、各バッチについて、図7Aに示すように、バッチ内でセンサの出力電流を平均化し、グルコース濃度に対してプロットした。バッチ1〜4の平均傾斜は、1.17nA/mM(CV=7.2%)であった。
Claims (89)
- Aは、負に帯電している請求項1記載のメンブラン。
- Aは、スルホン酸、カルボキシレート、およびホスフェートからなる群から選択される請求項1記載のメンブラン。
- Aは、スルホプロピル、スルホブチル、カルボキシプロピル、およびカルボキシペンチルからなる群から選択される請求項1記載のメンブラン。
- Aは、式L−Gからなり、ここで、LはC2−C12直鎖または分岐アルキル結合剤であり、Gは負に帯電したカルボキシまたはスルホン酸である請求項1記載のメンブラン。
- Lは、アリール、アルコキシ、アルケニル、アルキニル、−F、−Cl、−OH、アルデヒド、ケトン、エステル、またはアミドで置換されている請求項5記載のメンブラン。
- Dは、スチレンまたはC1−C18アルキルメタクリレートである請求項1記載のメンブラン。
- 前記重合体の平均分子量が、50,000を上回る請求項1記載のメンブラン。
- 前記重合体の平均分子量が、200,000を上回る請求項1記載のメンブラン。
- 前記重合体の平均分子量が、1,000,000を上回る請求項1記載のメンブラン。
- Bは、キレート化剤、負に帯電した成分、疎水性炭化水素成分、親水性ヒドロキシルまたはポリヒドロキシ成分、珪素重合体、およびポリ(エチレングリコール)からなる群から選択される請求項12記載のメンブラン。
- Bは、100〜20,000の分子量を有するポリ(エチレングリコール)である請求項12記載のメンブラン。
- [n/(n+m+l+p)]×100%が、1%〜25%である請求項12記載のメンブラン。
- [m/(n+m+l+p)]×100%が、1%〜15%である請求項12記載のメンブラン。
- [l/(n+m+l+p)]×100%が、20%〜90%である請求項12記載のメンブラン。
- [p/(n+m+l+p)]×100%が、1%〜50%である請求項12記載のメンブラン。
- 前記重合体の少なくとも一つの複素環窒素成分は独立して、ピリジン、イミダゾール、オキサゾール、チアゾール、ピラゾール、およびそれらの誘導体からなる群から選択される請求項1または12記載のメンブラン。
- 前記重合体の少なくとも一つの複素環窒素成分は独立して、2−ビニルピリジン、3−ビニルピリジン、4−ビニルピリジン、1−ビニルイミダゾール、2−ビニルイミダゾール、および4−ビニルイミダゾールからなる群から選択される請求項1または12記載のメンブラン。
- グルコースまたはラクテートの流束が、メンブランを横断するのを制限するのに十分な請求項1または12記載のメンブラン。
- グルコースまたはラクテートの流束が、メンブランを生体内で横断するのを制限するのに十分な請求項1または12記載のメンブラン。
- 前記架橋剤に少なくとも一つのエポキシド反応基が含まれている請求項1または12記載のメンブラン。
- 前記架橋剤の分子量が、200〜2,000である請求項1または12記載のメンブラン。
- 前記架橋剤が、ポリ(エチレングリコール)またはポリ(プロピレングリコール)の誘導体である請求項1または12記載のメンブラン。
- 前記重合体対前記架橋剤の重量比が、4:1〜32:1である請求項1または12記載のメンブラン。
- 前記重合体対前記架橋剤の重量比が、8:1〜16:1である請求項1または12記載のメンブラン。
- ポリ(エチレングリコール)の層をさらに含む請求項1記載のメンブラン。
- Aが、負に帯電している請求項30記載の電気化学センサ。
- Aは、スルホン酸、カルボキシレート、およびホスフェートからなる群から選択される請求項30記載の電気化学センサ。
- Aは、スルホプロピル、スルホブチル、カルボキシプロピル、およびカルボキシペンチルからなる群から選択される請求項30記載の電気化学センサ。
- Aは、式L−Gからなり、ここでLはC2−C12直鎖または分岐アルキル結合剤であり、Gは負に帯電したカルボキシまたはスルホン酸である請求項30記載の電気化学センサ。
- Lは、アリール、アルコキシ、アルケニル、アルキニル、−F、−Cl、−OH、アルデヒド、ケトン、エステル、またはアミドで置換されている請求項34記載の電気化学センサ。
- Dは、スチレンまたはC1−C18アルキルメタクリレートである請求項30記載の電気化学センサ。
- 前記重合体の平均分子量が、50,000を上回る請求項30記載の電気化学センサ。
- 前記重合体の平均分子量が、200,000を上回る請求項30記載の電気化学センサ。
- 前記重合体の平均分子量が、1,000,000を上回る請求項30記載の電気化学センサ。
- Bは、キレート化剤、負に帯電した成分、疎水性炭化水素成分、親水性ヒドロキシルまたはポリヒドロキシ成分、珪素重合体、およびポリ(エチレングリコール)からなる群から選択される請求項41記載の電気化学センサ。
- Bは、100〜20,000の分子量を有するポリ(エチレングリコール)である請求項41記載の電気化学センサ。
- [n/(n+m+l+p)]×100%が、1%〜25%である請求項41記載の電気化学センサ。
- [m/(n+m+l+p)]×100%が、1%〜15%である請求項41記載の電気化学センサ。
- [l/(n+m+l+p)]×100%が、20%〜90%である請求項41記載の電気化学センサ。
- [p/(n+m+l+p)]×100%が、1%〜50%である請求項41記載の電気化学センサ。
- 前記重合体の少なくとも一つの複素環窒素成分は独立して、ピリジン、イミダゾール、オキサゾール、チアゾール、ピラゾール、およびそれらの誘導体からなる群から選択される請求項30または41記載の電気化学センサ。
- 前記重合体の少なくとも一つの複素環窒素成分は独立して、2−ビニルピリジン、3−ビニルピリジン、4−ビニルピリジン、1−ビニルイミダゾール、2−ビニルイミダゾール、および4−ビニルイミダゾールからなる群から選択される請求項30または41記載の電気化学センサ。
- 前記メンブランは、グルコースまたはラクテートの流束がメンブランを横断するのを制限するのに十分なものである請求項30または41記載の電気化学センサ。
- 前記メンブランは、グルコースまたはラクテートの流束がメンブランを生体内で横断するのを制限するのに十分なものである請求項30または41記載の電気化学センサ。
- 前記架橋剤に少なくとも一つのエポキシド反応基が含まれている請求項30または41記載の電気化学センサ。
- 前記架橋剤の分子量が、200〜2,000である請求項30または41記載の電気化学センサ。
- 前記架橋剤が、ポリ(エチレングリコール)またはポリ(プロピレングリコール)の誘導体である請求項30または41記載の電気化学センサ。
- 前記重合体対前記架橋剤の重量比が、4:1〜32:1である請求項30または41記載の電気化学センサ。
- 前記重合体対前記架橋剤の重量比が、8:1〜16:1である請求項30または41記載の電気化学センサ。
- 前記メンブランが、ポリ(エチレングリコール)の層をさらに含む請求項30記載の電気化学センサ。
- 前記感知層に酵素、酵素安定剤、および架橋剤が含まれている請求項30記載の電気化学センサ。
- 前記感知層に酵素、重合体媒介物、および架橋剤が含まれている請求項30記載の電気化学センサ。
- Aが結合している複素環窒素は、双性イオン性である請求項61記載のメンブラン。
- Aは、カルボン酸より強い酸である請求項61記載のメンブラン。
- Bは、キレート化剤、負に帯電した成分、疎水性炭化水素成分、親水性ヒドロキシルまたはポリヒドロキシ成分、珪素重合体、およびポリ(エチレングリコール)からなる群から選択される請求項61記載のメンブラン。
- 前記重合体の少なくとも1 つの複素環窒素成分は独立して、2ービニルピリジン、3−ビニルピリジン、4−ビニルピリジン、1−ビニルイミダゾール、2−ビニルイミダゾール、および4−ビニルイミダゾールからなる群から選択される請求項61または64記載のメンブラン。
- グルコースまたはラクテートの流束が、メンブランを横断するのを制限するのに十分な請求項61または64記載のメンブラン。
- グルコースまたはラクテートの流束が、メンブランを生体内で横断するのを制限するのに十分な請求項61または64記載のメンブラン。
- 前記架橋剤に少なくとも一つのエポキシド反応性基が含まれている請求項61または64記載のメンブラン。
- 前記架橋剤の分子量が、200〜2,000である請求項61または64記載のメンブラン。
- 前記架橋剤が、ポリ(エチレングリコール)またはポリ(プロピレングリコール)の誘導体である請求項61または64記載のメンブラン。
- 前記重合体対前記架橋剤の重量比が、4:1〜32:1である請求項61または64記載のメンブラン。
- 前記重合体対前記架橋剤の重量比が、8:1〜16:1である請求項61または64記載のメンブラン。
- Aが結合している複素環窒素は、双性イオン性である請求項74記載の電気化学センサ。
- Aは、カルボン酸より強い酸である請求項74記載の電気化学センサ。
- Bは、キレート化剤、負に帯電した成分、疎水性炭化水素成分、親水性ヒドロキシルまたはポリヒドロキシ成分、珪素重合体、およびポリ(エチレングリコール)からなる群から選択される請求項77記載の電気化学センサ。
- 前記重合体の少なくとも一つの複素環窒素成分は独立して、ピリジン、イミダゾール、オキサゾール、チアゾール、ピラゾール、およびそれらの誘導体からなる群から選択される請求項74または77記載の電気化学センサ。
- 前記重合体の少なくとも一つの複素環窒素成分は独立して、2−ビニルピリジン、3−ビニルピリジン、4−ビニルピリジン、1−ビニルイミダゾール、2−ビニルイミダゾール、および4−ビニルイミダゾールからなる群から選択される請求項74または77記載の電気化学センサ。
- 前記メンブランは、グルコースまたはラクテートの流束がメンブランを横断するのを制限するのに十分なものである請求項74または77記載の電気化学センサ。
- 前記メンブランは、グルコースまたはラクテートの流束がメンブランを生体内で横断するのを制限するのに十分なものである請求項74または77記載の電気化学センサ。
- 前記架橋剤に少なくとも一つのエポキシド反応基が含まれている請求項74または77記載の電気化学センサ。
- 前記架橋剤の分子量が、200〜2,000である請求項74または77記載の電気化学センサ。
- 前記架橋剤が、ポリ(エチレングリコール)またはポリ(プロピレングリコール)の誘導体である請求項74または77記載の電気化学センサ。
- 前記重合体対前記架橋剤の重量比が、4:1〜32:1である請求項74または77記載の電気化学センサ。
- 前記重合体対前記架橋剤の重量比が、8:1〜16:1である請求項74または77記載の電気化学センサ。
- 前記感知層に酵素、酵素安定剤、および架橋剤が含まれている請求項74記載の電気化学センサ。
- 前記感知層に酵素、重合体媒介物、および架橋剤が含まれている請求項74記載の電気化学センサ。
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