JP2014501786A - 疎水性分子に誘起された分岐ポリマー凝集体及びその使用 - Google Patents
疎水性分子に誘起された分岐ポリマー凝集体及びその使用 Download PDFInfo
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- JP2014501786A JP2014501786A JP2013548584A JP2013548584A JP2014501786A JP 2014501786 A JP2014501786 A JP 2014501786A JP 2013548584 A JP2013548584 A JP 2013548584A JP 2013548584 A JP2013548584 A JP 2013548584A JP 2014501786 A JP2014501786 A JP 2014501786A
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Abstract
Description
[0003]最近、スターバーストデンドリマー(Starburst dendrimers)(又は高密度星型ポリマー(Dense Star polymers))及びコームバーストデンドリグラフト(Combburst dendrigrafts)(又は超櫛型分岐ポリマー(hyper comb−branched polymers))を含む、樹状ポリマーと呼ばれる新規な種類のポリマーが開発され、種々の工業用途に研究された。これらのポリマーは、多くの場合、ポリアミドアミン(PAMAM)系分岐ポリマー並びに米国特許第4,435,548号、第4,507,466号、第4,568,737号、第4,587,329号、第5,338,532号、第5,527,524号及び第5,714,166号に記載されるデンドリマーのように、(a)輪郭が明確なコア分子、(b)対称な(同一の長さの)分枝及び分岐点を有する少なくとも2つの同心円状の樹状層(世代)、及び(c)外表面基を有する。その他の例としては、米国特許第4,631,337号に開示されるもののような、ポリエチレンイミン(PEI)デンドリマー、米国特許第5,530,092号、第5,610,268号、及び第5,698,662号に開示されるもののような、ポリプロピレンイミン(PPI)デンドリマー、例えば、「Dendritic Molecules」Newkomeら編、VCH Weinheim、1996、「デンドリマー及びその他の樹状ポリマー」(「Dendrimers and Other Dendritic Polymers」)Frechet及びTomalia編、John Wiley & Sons,Ltd.2001、及び米国特許第7,754,500号に記載されるような、フレッシェ型のポリエーテル及びポリエステルデンドリマー、コア・シェル・テクトデンドリマー並びにその他が挙げられる。
非対称分岐ポリマー
[0007]SBPと異なり、非対称分岐ポリマー(ABP)、特に非対称分岐デンドリマー又は規則性ABP(reg−ABP)は、多くの場合、米国特許第4,289,872号、第4,360,646号、及び第4,410,688号に記載されるように、コア、制御され明確に規定された非対称(不均等な長さ)の分枝及び非対称の分岐点を有する。
ホモポリマー
[0010]ホモポリマーは、同一の繰り返し単位からなるポリマー又はポリマー主鎖に関することができる、すなわち、ホモポリマーは同じモノマーから生成する(例えば、ポリエチレンイミンデンドリマー、ポリアミドアミンデンドリマー又はポリオキサゾリンデンドリマー)。モノマーは、単純な化合物でもよく、又は複数の化合物の複合体若しくは組合せでもよく、その場合、当該組合せ若しくは複合体がホモポリマー中の繰り返し単位となる。このように、仮に組合せが3つの化合物A、B及びCからなるとした場合、複合体はABCと表記し得る。(ABC)−(ABC)−(ABC)・・・からなるポリマーは、本開示の目的のためのホモポリマーである。ホモポリマーは直鎖状であってもよいし、分岐状であってもよい。このように、ランダムに分岐したPEIの場合、異なる長さの分枝があり、分枝がランダムに起こるが、その分岐ポリマーは単一のモノマー、すなわちエチレンイミン又はアジリジンからなるので、その分子は本開示の目的のためのホモポリマーである。また、モノマー又は複合モノマーの構成成分の1種又は複数は、修飾、置換、誘導体化などを行うことができ、例えば、官能基をもつように修飾し得る。そのような分子は、主鎖が単純な又は複合した単一モノマーからなるので、本開示の目的のホモポリマーである。
難水溶性の薬剤
[0011]特定の目的のため又は特定の特性をもたせるために修飾することができる低分子の薬剤候補及び薬剤は、生体分子と同様に、水に対して難溶又は不溶である場合がある。一般的に、分子が循環器又は組織空間中で残存するためには親水性が必要であり、これにより薬理活性のある疎水性の薬剤候補又は薬剤の使用が制限され得る。それ故、難水溶性の医薬活性剤(PAA)のための効果的な製剤の開発は、薬剤の開発と使用において重要である。現在の解決策としては、例えば、化学的な修飾又は物理的な製剤によって薬剤の溶解性を向上させるか、又は薬剤の粒子径を低減することが挙げられる。
表面修飾された分岐ポリマーによる難水溶性薬剤の送達
[0023]SBP及びABPを含む分岐ポリマーが薬物送達に使用されてきたが、それらの試みは、主として、薬剤を化学的にポリマーに付着すること、又は、単分子カプセル化を通じて、そのような薬剤を内部に物理的にカプセル化することに注目したものである(米国特許第5,773,527号、第5,631,329号、第5,919,442号、及び第6,716,450号)。
対象とする薬剤
[0073]本開示に記載されるPAAは、任意の、化学的/低分子系薬剤、無機系薬剤、生物学的/高分子系薬剤、それらの修飾体及び/又は誘導体、及びそれらの組み合わせを包含し、ここで薬剤は水に対して難溶又は不溶である。従って、対象とする薬剤は、分子が非水溶性又は難水溶性となるように修飾された低分子、その塩であることができ、又は、非水溶性又は難水溶性となるように修飾された生体分子であることができる。
レドニゾロンコハク酸エステルナトリウム、ヒドロコルチゾンコハク酸エステルナトリウム、メチルプレドニゾロンコハク酸エステルナトリウム、トリアムシノロン・ヘキサカトニド、ヒドロコルチゾン、ヒドロコルチゾンシピオン酸エステル、プレドニゾロン、フルオロコーチゾン酢酸エステル、パラメタゾン酢酸エステル、プレドニゾロンテブレート(prednisolone tebulate)、プレドニゾロン酢酸エステル、プレドニゾロンリン酸エステルナトリウム、ヒドロコルチゾンコハク酸エステルナトリウムなど)、甲状腺ホルモン(例えばレボチロキシンナトリウムなど)など)、血糖降下剤(例えば、ヒトインスリン、精製ウシインスリン(beef insulin)、精製ブタインスリン(pork insulin)、グリブリド、クロルプロパミド、グリピジド、トルブタミド、トラザミドなど)、抗高脂血症薬(例えば、クロフィブレート、デキストロチロキシンナトリウム、プロブコール、ロバスタチン、ナイアシンなど)、タンパク質(例えば、DNアーゼ、アルギナーゼ、スーパーオキシドジスムターゼ、リパーゼなど)、核酸(例えば、ここに記載される任意のタンパク質を含む、任意の治療上有用なタンパク質をコードする、センス又はアンチセンス核酸など)、赤血球生成に有用な薬剤(例えばエリトロポイエチン)、抗潰瘍薬又は抗逆流薬(例えば、ファモチジン、シメチジン、ラニチジン塩酸塩など)、抗嘔吐薬又は鎮吐薬(例えば、メクリジン塩酸塩、ナビロン、プロクロルペラジン、ジメンヒドリナート、プロメタジン塩酸塩、チエチルペラジン、スコポラミンなど)、油溶性ビタミン(例えばビタミンA、D、E、Kなど)、及び、ミトタン、ビサジン(visadine)、ハロニトロソ尿素、アントロサイクリン(anthrocyclines)、エリプチシンなどのようなその他の薬剤を、同様に挙げることができる。
ナノ複合体すなわちナノ凝集体
[0079]ナノ複合体は、2種又はそれ以上の材料又は成分(例えばポリマー及びPAA分子)の物理的な混合物である。本開示において、そのような混合物は、固体状態又は液体状態の何れであっても、PAAと分岐ホモポリマー分子との間で形成される、異なったナノ領域の相又はドメインを含有することが可能である。ナノ複合体は、バルクのマトリックス(例えば、分岐ホモポリマー及びPAA)及び、構造及び化学の相違に起因して異なる特性を示し得る大きさがナノである相(複数可)(例えば、PAA及び分岐ポリマーの表面基により形成されるドメイン、同様に、分岐ポリマーの内部によって形成されるドメイン)の組み合わせを含むことができる。ドメイン/相の溶解性は異なり得るため、ナノ複合体を水性溶液に溶解すると、相の内の1つが、1つ又は複数のその他の相よりも速やかに溶解し、これにより複合凝集体が徐々に分解することとなり、結果として、勾配をもって、且つ制御された状態で複合体成分を放出する、及び任意に、成分の1つ又は複数を、新しい凝集体などの、新規な形態に再形成することとなり得る。
[0088]本開示の別な実施形態において、修飾SBPは、例えば、ホモポリマー上の好適な部位との反応になじむことが知られている種々の合成スキームの任意のものを用いて製造され得る。更に、種々の修飾すなわちホモポリマー主鎖への付加をもたらすための選択した合成スキームにおいて、任意の種々の反応剤が使用され得る。このように、例えば、上述のアミンに対するマイケル付加反応の場合、例えば、アルキル化の段階において、例えば、1〜約22の炭素を含み、置換された、脂肪族の、芳香族の、環状の、1つ又は複数の結合において飽和であり、又はそれらの組み合わせである飽和又は不飽和の炭化水素などの炭化水素置換基を含むアクリルエステルなどの任意の種々のアクリル反応剤を用いて、任意の種々の置換基の付加を用いることができる。このように、好適な反応原料としては、アクリル酸メチル、アクリル酸エチル、アクリル酸プロピル、アクリル酸ブチル、アクリル酸ペンチル、アクリル酸ヘキシル、アクリル酸ヘプチル、アクリル酸オクチル、アクリル酸ノニル、アクリル酸デシル、アクリル酸ウンデシル、アクリル酸ドデシルなど、及びそれらの混合物を挙げることができる。同様に、上記に例示した例におけるアミド化においては、任意の種々のアミンを用いることができる。例えば、エチレンジアミン、モノエタノールアミン、トリス(ヒドロキシメチル)アミノメタン、アルキルアミン、アリルアミン、又は、PEG、PEO、全フッ素化ポリマー、ポリスチレン、ポリエチレン、ポリジメチルシロキサン、ポリアクリル酸エステル、ポリメタクリル酸メチルなど、及びそれらの組み合わせを含むものを包含する、任意のアミノ修飾ポリマーを用いることができる。
[0094]ABPを製造するための合成プロセスは、多くの場合、高分子中に種々の分岐点を生成する。換言すると、末端分岐点及び連鎖分岐点の混合物が分子構造を通じて分布している。デンドリマー及びデンドリグラフトと比較すると、ランダムABPの分岐密度はより低くでき、分子構造はよりオープンにすることができる。分枝様式はランダムであるにもかかわらず、Dickら、J.Macromol.Sci.Chem.、A4(6)、1301−1341(1970)及びLukovkin、Eur.Polym.J.9、559(1973)に記載されるように、第一級アミン基、第二級アミン基及び第三級アミン基の平均比は、約1:2:1の比に比較的一致することができる。
[00109]従って、診断薬は、対象とするナノ複合体の表面上に定着させ得る、又はその中に封入され得る金属含有物質又は常磁性材料、例えば磁気共鳴画像診断用材料、であることができ、ナノ粒子は診断薬及び治療薬の両方として使用することができる。本開示の更に別な態様において、ナノ粒子を含有する画像診断用材料は、更に、そのようなナノ粒子を、治療処置が必要な特定の位置、例えば腫瘍部位に向けることを可能にする、標的部分/基を含むことができる。
薬剤の製剤化及びナノ粒子の調製
[00114]PAA及び修飾ホモポリマーは、それぞれ、緩衝液、アセトン、エタノールなどの好適な緩衝液及び/又は溶媒に、一般的にはミリグラム又はナノグラムの量である、生体内での使用に対して確立された濃度などの好適な濃度において、懸濁され得る。次に、2つの溶液を、室温又はPAA及びホモポリマーを完全な状態で維持することが許容されることが知られている別の温度などの好適な温度にて、1時間、2時間などの好適な時間、混合する。対象とする凝集体は一旦形成された後は安定であるため、その他のインキュベーション時間は数分から数時間の間で変化し得る。凝集体は、ろ過、遠心分離、蒸発、凍結乾燥、透析などの本技術分野で公知の方法を実施することにより、濃縮又は収集することができる。凝集体は保存可能期間を延長するために、乾燥することができる。
[00137]対称分岐PPIデンドリマーは、Sigma−Aldrichより購入した。対称分岐PEIデンドリマー及びデンドリグラフトは、米国特許第4,631,337号、第5,773,527号、第5,631,329号及び第5,919,442号に提示される操作に従って調製した。全ての抗体はSigma−Aldrich、Biodesign又はFitzgeraldより購入した。異なる世代のPAMAMデンドリマーはDendritech,Inc.より購入した。
修飾したアミノ官能基を有する対称分岐PPI(m−SB−PPI−NH2−1.0)の合成
[00138]対称分岐PPIデンドリマー(SB−PPI−4、8、16、32、64、MW 316、773、1,687、3,514及び7,168)、アクリル酸メチル(MA、FW=86.09)、エチレンジアミン(EDA、FW=60.10)及びメタノールを利用した。
修飾した混合した水酸及びアミノ官能基を有する対称分岐PPI(mix−SB−PPI−64−NH2/OH−2)の合成
[00142]アミノ基で官能化された対称分岐PPI(m−SB−PPI−NH2−1.0)、MA、EDA、モノエタノールアミン(MEA、FW=61.08)及びメタノールを利用した。
修飾したアミノ官能基を有するランダム非対称分岐PEI(m−ran−AB−PEI−NH2−1.0)の合成
[00147]ランダム非対称分岐PEI(ran−AB−PEI、MW 2,000、25,000、及び75,000)、MA、EDA及びメタノールを利用した。
炭化水素連鎖を有する分岐ポリマーの修飾
[00151]10%の炭化水素連鎖を有するランダム分岐PEIの修飾を例として用いた。1グラムの分岐PEI(FW=25000)を10mLのメタノールに溶解した。この溶液に、0.23gの1,2−エポキシヘキサン(FW=100.16)を添加し、混合物を40℃で2時間加熱した。次に溶媒をロータリーエバポレータで除去し、残渣を水に再溶解した。透析(3,500カットオフ)した後、修飾されたPEIが生成した。種々の比率(%)及び長さ(例えば、C4、C12、C18及びC22)の炭化水素連鎖を有するPAMAM、PEI、及びPPIデンドリマー並びにデンドリグラフトその他のMBP、並びに非対称PLLを同様の手順によって調製した。
修飾した、混合した水酸及びアミノ官能基を有するランダム非対称分岐PEI(m−ran−AB−PEI−NH2/OH−2)の合成
[00152]アミノ基で官能化されたランダム非対称分岐PEI(m−ran−AB−PEI−NH2−1.0)、MA、EDA、モノエタノールアミン(MEA、FW=61.08)及びメタノールを利用した。
アルキル修飾した、第一アミン連鎖末端基を有するランダム非対称分岐ポリ(2−エチルオキサゾリン)(PEOX)の合成
[00156]CH3−(CH2)11−PEOX−ABP100(ABP100は独自に付した名称であり、反応開始時におけるモノマーの開始剤に対する比を与える)の合成を、コア・シェル構造調製の一般的な手法として提供する。CH3−(CH2)11−Br(2.52g)を500mlのトルエンに加えた混合物を、蒸留のための上部器具を取り付けて、N2下、約15分間、共沸処理して水を除去した。2−エチルオキサゾリン(100g)を滴下ロートを通して滴下して添加し、混合物を24〜48時間還流した。重合が完結したところで、12.12gのEDAを反応性ポリマー溶液(A)に添加し、アミン官能基を導入した。ポリオキサゾリン連鎖末端のEDAに対するモル比は、1〜20であった。
混合表面修飾対称分岐ポリマー−IgGコンジュゲートの合成
[00158]混合表面(OH/NH2混合)修飾対称分岐PPI−IgGコンジュゲート(mix−m−SB−PPI−64−NH2/OH−2−IgGコンジュゲート)の調製を、ポリマー・抗体コンジュゲート及びポリマー・ストレプトアビジンコンジュゲートを調製する一般的な手法として提供する。m−SB−PPI−4−NH2−1−IgG、m−SB−PPI−8−NH2−1−IgG、m−SB−PPI−16−NH2−1−IgG、m−SB−PPI−32−NH2−1−IgG、m−SB−PPI−4−NH2−2−IgG、m−SB−PPI−8−NH2−2−IgG、m−SB−PPI−16−NH2−2−IgG、m−SB−PPI−32−NH2−2−IgG、m−SB−PPI−4−NH2−3−IgG、m−SB−PPI−8−NH2−3−IgG、m−SB−PPI−16−NH2−3−IgG、m−SB−PPI−32−NH2−3−IgG、mix−m−SB−PPI−4−NH2/OH−1(OH/NH2混合)−IgG、mix−m−SB−PPI−8−NH2/OH−1(OH/NH2混合)−IgG、mix−m−SB−PPI−16−NH2/OH−1(OH/NH2混合)−IgG、mix−m−SB−PPI−32−NH2/OH−1(OH/NH2混合)−IgG、mix−m−SB−PPI−4−NH2/OH−2(OH/NH2混合)−IgG、mix−m−SB−PPI−8−NH2/OH−2(OH/NH2混合)−IgG、mix−m−SB−PPI−16−NH2/OH−2(OH/NH2混合)−IgG、mix−m−SB−PPI−32−NH2/OH−2(OH/NH2混合)−IgG、mix−m−SB−PPI−4−NH2/OH−3(OH/NH2混合)−IgG、mix−m−SB−PPI−8−NH2/OH−3(OH/NH2混合)−IgG、mix−m−SB−PPI−16−NH2/OH−3(OH/NH2混合)−IgG、mix−m−SB−PPI−32−NH2/OH−3(OH/NH2混合)−IgGなどのその他のコンジュゲート、並びに第一級アミン及び混合OH/NH2修飾コームバーストPEIデンドリグラフト(0〜5世代)もまた、同様の手順で得た。その他の対象とする修飾SBPに付加されたタンパク質の合成もまた、同様の手順でなし遂げられた。ビオチン化IgGコンジュゲートを、Bioconjugate Techniques(G,Hermanson、Academic Press、1996)に提示される方法で合成した。
LC−SPDP−混合表面m−SB−PPI−64−NH2/OH−2
[00159]400μlのリン酸緩衝液(20mMリン酸塩及び0.1M NaCl、pH7.5)中の混合表面ランダム分岐mix−m−SB−PPI−64−NH2/OH−2(4×10−7モル)に、400μlの水中の4.0×10−6モルのスルホ−LC−SPDP(Pierce、IL)を添加した。この混合物をボルテックス混合し、30℃にて30分間インキュベートした。LC−SPDP−mix−m−SB−PPI−64−NH2/OH−2をゲルろ過クロマトグラフィーにて精製し、緩衝液A(0.1M リン酸塩、0.1M NaCl及び5mM EDTA、pH6.8)にて平衡化した。生成物を更に濃縮して、約0.77nmolの濃度を有する465μLの溶液を得た。
LC−SPDP mix−m−SB−PPI−64−NH2/OH−2からのチオール化mix−m−SB−PPI−64−NH2/OH−2
[00160]LC−SPDP mix−m−SB−PPI−64−NH2/OH−2(65μlの緩衝液A中に50nmol)を100μLのジチオトレイトール(DTT)(緩衝液A中に50mM)と混合し、室温にて15分間インキュベートした。緩衝液Aと共にゲルろ過して、過剰のDTT及び副生成物を除去した。生成物を10KのCentricon Concentrator中で濃縮して、390μLのチオール化mix−m−SB−PPI−64−NH2/OH−2を得て、これを活性化された抗体とのコンジュゲーションに使用した。
マレイミドR(MAL−R)−活性化された抗体
[00161]PBS中の抗体(310μL、5.1mgすなわち34nmol)に、20.4μLのMAL−R−NHS(N−ヒドロキシスクシンイミド)溶液(10mMの水中)を添加した。この混合物をボルテックス混合し、30℃にて15分間インキュベートした。生成物を緩衝液Aと共にゲルろ過して精製した。マレイミド−R−活性化された抗体をチオール化したmix−m−SB−PPI−64−NH2/OH−2とのコンジュゲーションに使用した。
mix−m−SB−PPI−64−NH2/OH−2−抗体コンジュゲート
[00162]チオール化したmix−m−SB−PPI−64−NH2/OH−2(310μLすなわち35.7nmol)に、MAL−R−活性化された抗体(4.8mLすなわち34nmol)を添加した。反応混合物を約800μLまで濃縮し、4℃にて一晩及び/又は室温にて約1時間インキュベートした。インキュベーションが完了したところで、反応を100μLのエチルマレイミド(50mmolの溶液)によってクエンチし、コンジュゲートをカルボキシメチルセルロースカラム(5mL)上、20mMリン酸塩緩衝液中、pH6で、塩化ナトリウムによる段階的勾配により、分別を行った。コンジュゲートは、塩化ナトリウム勾配と共に流出し、カチオン交換クロマトグラフィー、UV分光分析及びポリアクリルアミドゲル電気泳動によってこれを同定した。
還元的カップリングによるコンジュゲーション
抗体の還元
[00163]160μLの緩衝液B(0.1Mリン酸ナトリウム、5mM EDTA及び0.1M NaClを含み、pH6.0)中2.1mgすなわち14nmolの抗体に対して、40μLのDTT(緩衝液B中50mM)を添加した。この溶液を室温にて30分間静置した。緩衝液Bにて平衡化したSephadex G−25カラム中でのゲルろ過により、生成物を精製した。還元された抗体を220μLまで濃縮し、コンジュゲーションに使用した。
MAL−R−混合表面修飾SBP
[00164]pH7.4、400μL中の混合表面修飾SBP(400×10−9モル)に対して、400μLのMAL−R−NHS(水中10mM)を添加した。これを混合して、30℃にて15分間インキュベートした。終了後、緩衝液Bにて平衡化したSephadex G−25カラム上で、生成物を精製した。MAL−R−混合表面修飾SBPを収集し、同一の緩衝液中、分割して−40℃にて保存した。
混合表面修飾SBP−抗体コンジュゲート
[00165]還元された抗体(220μL中14nmol)に対して、MAL−R−mix−m−SB−PPI−64−NH2/OH−2(154μL、16.6nmol)を撹拌下に添加した。12.5μLの炭酸ナトリウム(1.0M溶液)を添加することにより、pHを約6.8に調整し、室温にて1時間、反応を継続し、100μLのシステアミン(0.4mM溶液)を添加して反応を停止した。コンジュゲート混合物をCMセルロースカラム上で塩化ナトリウム濃度勾配流出液を用いて精製した。
IgG−非対称ランダム分岐ポリマーコンジュゲートの調製
[00166]ランダム分岐混合表面(OH/NH2混合)m−ran−AB−PEI−NH2/OH−2−IgGコンジュゲートの調製を、ポリマー−抗体コンジュゲート及びポリマー−ストレプトアビジンコンジュゲートを調製する一般的な手法として提供する。PEI−IgG、m−ran−AB−PEI−NH2−1−IgG、m−ran−AB−PEI−NH2−2−IgG、m−ran−AB−PEI−NH2−3−IgG、m−ran−AB−PEI−NH2−4−IgG、及びm−ran−AB−PEI−NH2/OH−1(OH/NH2混合)−Ig、m−ran−AB−PEI−NH2/OH−2(OH/NH2混合)−IgG、m−ran−AB−PEI−NH2/OH−3(OH/NH2混合)−IgG、規則性ポリリジンポリマー、連鎖末端に第一級アミンを有するアルキル修飾ランダム分岐ポリ(2−エチルオキサゾリン)などの、その他のコンジュゲートの全てを同様の手順で合成した。種々のタンパク質の非対称ランダム分岐PEOXポリマーとのコンジュゲートの合成もまた、同様の手順で行われた。ビオチン化IgGコンジュゲートを、Bioconjugate Techniques(G,Hermanson、Academic Press、1996)に提示される方法で合成した。
LC−SPDP−混合表面m−AB−PEI−NH2/OH−2
[00167]400μLのリン酸緩衝液(20mMリン酸塩及び0.1M NaCl、pH7.5)中の混合表面ランダム分岐m−ran−AB−PEI−NH2/OH−2(4×10−7モル)に対して、400μlの水中の4.0×10−6モルのスルホ−LC−SPDP(Pierce、IL)を添加した。これをボルテックス混合し、30℃にて30分間インキュベートした。LC−SPDP−m−ran−AB−PEI−NH2/OH−2をゲルろ過クロマトグラフィーにて精製し、緩衝液A(0.1M リン酸塩、0.1M NaCl及び5mM EDTA、pH6.8)にて平衡化した。生成物を更に濃縮して、約0.77nmol/μmolの濃度を有する465μlの溶液を得た。
LC−SPDP m−ran−AB−PEI−NH2/OH−2からのチオール化m−ran−AB−PEI−NH2/OH−2
[00168]LC−SPDP m−ran−AB−PEI−NH2/OH−2(65mlの緩衝液A中に50nmol)を100μLのジチオトレイトール(DTT)(緩衝液A中に50mM)と混合し、室温にて15分間インキュベートした。緩衝液Aと共にゲルろ過して、過剰のDTT及び副生成物を除去した。生成物を10KのCentricon Concentrator中で濃縮して、390μLのチオール化m−ran−AB−PEI−NH2/OH−2を得て、これを活性化された抗体とのコンジュゲーションに使用した。
m−ran−AB−PEI−NH2/OH−2−抗体コンジュゲート
[00170]チオール化したm−ran−AB−PEI−NH2/OH−2(310μLすなわち35.7nmol)に対して、MAL−R−活性化された抗体(4.8mLすなわち34nmol)を添加した。反応混合物を約800μLまで濃縮し、4℃にて一晩及び/又は室温にて約1時間インキュベートした。インキュベーションが完了したところで、反応を100μLのエチルマレイミド(50mmolの溶液)によってクエンチし、コンジュゲートをカルボキシメチルセルロースカラム(5ml)上、20mMリン酸塩緩衝液中、pH6で、塩化ナトリウムによる段階的濃度勾配により、分別を行った。コンジュゲートは、塩化ナトリウム濃度勾配と共に流出し、カチオン交換クロマトグラフィー、UV分光分析及びポリアクリルアミドゲル電気泳動によってこれを同定した。
パクリタキセルの製剤化及びナノ粒子の調製
[00171]パクリタキセルをエタノールに溶解し、40mg/mLまで濃縮した。
ナノ粒子の測定
[00178]薬剤誘起ポリマー凝集体のみならず、種々のポリマー、ポリマーのみの凝集体の大きさを、Malvern Zetasizer Naco−ZS Zen3600粒径分析器を用いて、動的光散乱法により測定した。
活性試験
[00179]生細胞の代謝は、NADH又はNADPHなどの「還元当量」を生成する。そのような還元性の化合物は、テトラゾリウム生成物MTS(Promega)を、水溶性で可溶であり、着色している生成物であるホルマザンへと還元できる中間的な電子移動剤に電子を渡す。細胞は、死ぬと、急速にテトラゾリウム生成物を還元する能力を失う。従って、着色のあるホルマザン生成物は、培地中に生存する細胞の数に比例する。
CellTiter 96(登録商標)Aqueous製品(Promega)は、培地中の生存する細胞の数を決定するMTSアッセイである。MTSテトラゾリウムはMTTテトラゾリウムと類似するが、MTS還元のホルムザン生成物が細胞の培地中に可溶であり、可溶化のための溶媒を必要としないという利点を有する。アッセイウェルに直接、推奨される培地100μl当たり20μlの比で添加する単一の試薬を使用した。細胞を1〜4時間、37℃で培養し、次に490nmにおける吸光度を測定した。
カンポテシン(Campothecin)の製剤化及びナノ粒子の調製
[00185]カンプトテシン(2.1mg)及びポリマー(10.5mg)を、4:1(v/v)クロロホルム:エタノール混合物に溶解する。完全に混合した後、ロータリーエバポレータ上で溶媒を除去して乾固する。得られた固体混合物を2mLの生理食塩水溶液に再溶解し、混合し、次に0.8umのシリンジフィルターを通してろ過する。ろ液を凍結乾燥用バイアル中で−70℃にて少なくとも2時間凍結し、その後一晩(〜16時間)凍結乾燥する。バイアルに栓をして、すぐに使用可能な白色粉末は−70℃で保存する。この物質は、使用の直前に、2mLの水で再構成する。
Claims (12)
- a)表面基により修飾された分岐ホモポリマーであり、前記表面修飾された分岐ホモポリマーが、対称分岐ポリマー、非対称分岐ポリマー、又はそれらの組み合わせを含む、前記分岐ホモポリマー、及び
b)非水溶性又は難水溶性の医薬活性剤(PAA)
を含む凝集体であって、
前記凝集体の大きさが、前記表面修飾された分岐ホモポリマー単独から形成される凝集体の大きさと異なる、凝集体。 - 前記表面修飾された分岐ホモポリマーが疎水性表面基を含む、請求項1に記載の凝集体。
- 前記PAAが前記分岐ポリマーの表面基と結合している、請求項1に記載の凝集体。
- 前記表面修飾された分岐ポリマーが、ポリオキサゾリン、ポリ(2−置換オキサゾリン)、ポリエチレングルコール、ポリエチレンオキシド、ポリアクリルアミド、ポリリン酸エステル、ポリビニルピロリドン、ポリビニルアルコール、ポリエチレンイミン、ポリプロピレンイミン、ポリアミドアミン、又はそれらの組み合わせを含む、請求項2に記載の凝集体。
- 前記表面修飾された分岐ポリマーが、1〜約22の炭素原子を含む脂肪族及び/又は飽和若しくは不飽和炭化水素、芳香族炭化水素、ポリエチレンポリマー、ポリスチレンポリマー、パーフルオロポリマー、ポリジメチルシロキサン、ポリアクリル酸エステル、ポリメタクリル酸メチル又はそれらの組み合わせを含む、請求項2に記載の凝集体。
- 前記非水溶性又は難水溶性のPAAが、抗感染症薬、又は抗腫瘍薬を含む、請求項1に記載の凝集体。
- 前記非水溶性又は難水溶性のPAAが、パクリタキセル、ドセタキセル、タキソテーレ、ビンブラスチン、ビンクリスチン、ビンデシン、ビノレルビン、イリノテカン、トポテカン、カンプトテシン、カンプトテシン誘導体(イリノテカン、トポテカン他など)、ドキソルビン、シスプラチン、カルボプラチン、オキサリプラチン、サトラプラチン、ドラルジン、ロペラミド、ツボクラリン、イブプロフェン、ジアゼパム、ナプロキセン、カルバマゼピン、グリセオフォルビン、ニフェジピン、フィトステロール、オメプラゾール、ドンペリドン、ジドブジン、アムホテリシンB、クロルメチン、クロラムブシル、ブスルファン、チオテパ、シクロホスファミド、エストラムスチン、イホスファミド、メクリロレタミン、メルファラン、ウラムスチン、ロヌイスチン、ストレプトゾトシン、ダカルバジン、プロカルバジン、テモゾレニド、(SP−4−3)−(cis)−アミンジクロロ−[2−メチルピリジン]−白金(II)、メトトレキサート、ペメトレキセド、ラルチトレキセド、トリメトレキサート、クラドリビン、クロロデオキシアデノシン、クロファラビン、フルダラビン、メルカプトプリン、ペントスタチン、チオグアニン、アザシチジン、カペシタビン、シタラビン、エダトレキサート、フロクスリジン、5 フルオロウラシル、ゲムシタビン、トロキサシタビン、ブレオマイシン、ダクチノマイシン、アドリアマイシン、アクチノマイシン、ミタラマイシン、マイトマイシン、ミトキサントロン、ポルフィロマイシン、ダウノルビシン、エピルビシン、イダルビシン、バルルビシン、フェネステリン、タモキシフェン、ピポスルファンカンプトテシン、アムサクリン、エトポシド、テニポシド、フルオキシメステロン、テストラクトン、ビカルタミド、シプロテロン、フルタミド、ニルタミド、アミノグルテチミド、アナストロゾール、エキセメスタン、ホルメスタン、レトロゾール、デキサメタゾン、プレドニゾン、ジエチルスチルベストロール、フルベストラント、ラロキシフェン、トレミフェン、ブセレリン、ゴセレリン、リュープロリド、トリプトレリン、メドロキシプロゲステロン酢酸エステル、メゲストロール酢酸エステル、レボチロキシン、リオチロニン、アルトレタミン、レバミゾール、ミトタン、オクトレオチド、プロカルバジン、スラミン、サリドマイド、メトキサレン、ポリフィマーナトリウム、ボルテゾミブ、エルロチニブ塩酸塩、ゲフィチニブ、イマチニブメシル酸塩、セマキサニブ、アダパレン、ベキサロテン、トランス−レチノイン酸、9−シス−レチノイン酸及びN−(4−ヒドロキシフェニル)レチンアミド又はそれらの組み合わせを含む、請求項1に記載の凝集体。
- 前記ホモポリマーに共有結合した標的指向性部分を更に含み、前記部分が抗体、その抗原結合性部分、抗原、細胞受容体、細胞受容体リガンド又はレクチンリガンドを含む、請求項1に記載の凝集体。
- 更に造影剤を含む、請求項1に記載の凝集体。
- 前記ポリ(2−置換オキサゾリン)が、ポリ(2−メチルオキサゾリン)、ポリ(2−エチルオキサゾリン)、ポリ(2−プロピルオキサゾリン)又はポリ(2−ブチルオキサゾリン)を含む、請求項4に記載の凝集体。
- 前記造影剤が磁気共鳴画像形成用造影剤である、請求項9に記載の凝集体。
- 前記造影剤が放射性核種である、請求項9に記載の凝集体。
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JP2022503696A (ja) * | 2018-10-17 | 2022-01-12 | サンステイト バイオサイエンシーズ, エルエルシー | 治療効果を高めるために単一タンパク質でカプセル化された医薬品 |
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JP2020512448A (ja) * | 2017-03-14 | 2020-04-23 | フリードリヒ−シラー−ユニバーシタット イエナ | ポリ(オキサゾリン)安定化剤を含有する有機ポリマー粒子および有機ポリマー粒子の安定化のためのポリ(オキサゾリン)の使用 |
JP7193470B2 (ja) | 2017-03-14 | 2022-12-20 | フリードリヒ-シラー-ユニバーシタット イエナ | ポリ(オキサゾリン)安定化剤を含有する有機ポリマー粒子および有機ポリマー粒子の安定化のためのポリ(オキサゾリン)の使用 |
JP2022503696A (ja) * | 2018-10-17 | 2022-01-12 | サンステイト バイオサイエンシーズ, エルエルシー | 治療効果を高めるために単一タンパク質でカプセル化された医薬品 |
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WO2012094620A3 (en) | 2012-10-26 |
WO2012094620A2 (en) | 2012-07-12 |
WO2012094620A9 (en) | 2013-01-03 |
US20210059939A1 (en) | 2021-03-04 |
JP6092121B2 (ja) | 2017-03-08 |
EP2661281B1 (en) | 2021-03-10 |
EP2661281A2 (en) | 2013-11-13 |
US20140314664A1 (en) | 2014-10-23 |
CA2824063A1 (en) | 2012-07-12 |
US10688048B2 (en) | 2020-06-23 |
CN103429267A (zh) | 2013-12-04 |
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US20180235884A1 (en) | 2018-08-23 |
CA2824063C (en) | 2020-02-18 |
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