JP2014512426A - 星型ポリマー・ナノシェルおよびその調製方法 - Google Patents
星型ポリマー・ナノシェルおよびその調製方法 Download PDFInfo
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- JP2014512426A JP2014512426A JP2013558280A JP2013558280A JP2014512426A JP 2014512426 A JP2014512426 A JP 2014512426A JP 2013558280 A JP2013558280 A JP 2013558280A JP 2013558280 A JP2013558280 A JP 2013558280A JP 2014512426 A JP2014512426 A JP 2014512426A
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- polymer
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Abstract
【解決手段】i)6つ以上の独立したポリマー・アームに共有結合した架橋コアを有する両親媒性単分子星型ポリマー、およびii)星型ポリマーに内包されたカーゴ材料を含む星型ポリマー内包複合体;および星型ポリマー内包複合体の外側表面と接触した無機材料を含むシェル、を含むナノシェルを開示する。
【選択図】図5
Description
本発明は、インターナショナル・ビジネス・マシーンズ・コーポレーションとサンノゼ州立大学研究財団との間の共同研究契約に基づきなされた。
i)6つ以上の独立したポリマー・アームに共有結合した架橋コアを有する両親媒性単分子星型ポリマー、およびii)星型ポリマーに内包されたカーゴ材料を含む星型ポリマー内包複合体;および
星型ポリマー内包複合体の外側表面と接触した無機材料を含むシェル
を含むナノシェルを開示する。
カーゴ材料の非溶媒である第2の溶媒に混合物を注入することにより、星型ポリマーに内包されたカーゴ材料を含む星型ポリマー内包複合体を形成するステップ;および
1つまたは複数の連続的プロセスを用いて星型ポリマー内包複合体の外側表面にシェル形成無機材料を付着させることにより、1つまたは複数の無機シェル層を含むシェルを含むナノシェルを形成するステップ
を含む方法を開示する。
カーゴ材料の非溶媒である第2の溶媒に混合物を注入することにより、星型ポリマー、カーゴ材料、および酸化鉄粒子を含むナノシェルを形成するステップ
を含む別の方法も開示する。
ビニル重合の方法はよく知られており、フリーラジカル重合、リビングアニオン付加重合およびリビングフリーラジカル重合(たとえば、ニトロキシド媒介ラジカル重合(NMP)、原子移動ラジカル重合(ATRP)、ならびに可逆的付加開裂連鎖移動(RAFT))があるが、これに限定されるものではない。
スキーム1
実施形態の1つでは、星型ポリマーは生分解性である。好ましくは、こうした星型ポリマーの多分散性指数は1.35以下である。生分解性星型ポリマーは、好ましくは化学式に制限金属を含む触媒ではなく、有機触媒の使用を含む重合方法を用いて形成される。実施形態の1つでは、星型ポリマーのコアは、その後合成変換することができる6つ以上の部位を含み、その部位は、アルコール、アミン、カルボン酸、アジド、アルキン、アルケン、ハロゲン基およびこれらの組み合わせからなる群から選択される官能基を含む。
スキーム2。
ポリエーテル鎖は、星型ポリマーに親水性を与える重要な手段となり得る。上記のように、モノ・エンド・キャップしたポリエーテルアルコール(たとえば、ポリ(アルキレングリコール)は、環状カルボニル・モノマーの開環重合の開始剤として利用することで、得られたポリマー・アーム前駆体に主鎖親水性ブロックを導入することができる。
HO−[C(R7)2(C(R7)2)a’C(R7)2O]n−H (4)、
式中、a’は0〜8であり、nは2〜10000の整数であり、R7は各々独立に水素および1〜30個の炭素のアルキル基からなる一価ラジカルである。このため、エーテル繰り返し単位は、各骨格酸素との間に2〜10個の骨格炭素を含む。より詳細には、ポリ(アルキレングリコール)は、下記式(5)で表される、モノ・エンド・キャップしたポリ(アルキレングリコール)であってもよい:
R8O−[C(R7)2(C(R7)2)a’C(R7)2O]n−H (5)、
式中、R8は1〜20個の炭素を含む一価炭化水素ラジカルである。
Z’−[C(R7)2(C(R7)2)a’C(R7)2O]n−1−H (6)、
式中、Z’は末端繰り返し単位の骨格炭素および酸素を含む一価ラジカルであり、2〜100個の炭素を有してもよい。以下の非限定的な例は、ポリ(エチレングリコール)(PEG)のモノ・エンド誘導体化を説明する。上記のように、モノメチルPEG(MPEG)などのPEGの繰り返し単位の片末端を、1〜20個の炭素を有する一価炭化水素基でキャップしてもよく、Z’は、上記のスキーム2のMPEGで詳細に示したようにMeOCH2CH2O−である。MeOCH2CH2O−の末端のダッシュは、ポリエーテル鎖に対する結合点を示す。別の例では、Z’は、HSCH2CH2O−などのチオール基、またはMeSCH2CH2O−などのチオエーテル基を含む。別の例では、PEGの片末端単位はアルデヒドであり、式中、Z’はOCHCH2CH2O−であってもよい。アルデヒドを第一級アミンで処理すると、Z’がR9N=CHCH2CH2O−であるイミンが得られる。R9は水素、1〜30個の炭素のアルキル基、または6〜100個の炭素を含むアリール基から選択される一価ラジカルである。続いて、イミンを、Z’がR9NHCH2CH2CH2O−であるアミンに還元する。別の例では、PEGの片末端繰り返し単位を、Z’がHOOCCH2O−であるカルボン酸に酸化してもよい。既知の方法を用いて、カルボン酸をエステルに変換することができ、Z’はR9OOCCH2O−になる。あるいは、カルボン酸はアミドに変換することもでき、Z’はR9NHOCCH2O−になる。多くの他の誘導体も可能である。特定の実施形態では、Z’は、特定の細胞型と相互作用する生物活性部分を含む基である。たとえば、Z’基は、肝細胞を特異的に認識するガラクトース部分を含んでもよい。この例では、Z’は下記構造を有する。
環状カルボニル・モノマーは、下記一般式(7)を有してもよい。
R2−C(CF3)2OH (14)
R2は、水素、または1〜20個の炭素を有する一価ラジカル、たとえばアルキル基、置換アルキル基、シクロアルキル基、置換シクロアルキル基、ヘテロシクロアルキル基、置換ヘテロシクロアルキル基、アリール基、置換アリール基、またはこれらの組み合わせである。例示的な1つの水素結合を供与する触媒を表3に示す。
星型ポリマー内包複合体は、星型ポリマーおよびそれに内包された好適なカーゴ材料を含む。実施形態の1つでは、カーゴ材料は、薬剤、遺伝子、色素、画像コントラスト向上材料、およびこれらの組み合わせからなる群から選択される。カーゴ材料は、上述の制限金属の1種または複数種を含む金属を含んでもよい。カーゴ材料は、放射性金属をさらに含んでもよい。星型ポリマー内包複合体は、pH5.0〜8.0の水溶液での平均粒度が、動的光散乱により測定した場合、2nm〜500nm、2nm〜250nm、2nm〜150nm、2nm〜120nm、より詳細には10nm〜120nm、20nm〜120nm、30nm〜120nm、なおより詳細には50nm〜120nmである。星型ポリマー内包複合体は、たとえば星型ポリマー内包複合体の総乾燥重量に対して0.1〜90wt%、より詳細には5〜50wt%、なおより詳細には15〜50wt%の生物活性材料を含んでもよい。実施形態の1つでは、生物活性カーゴ材料は薬剤である。別の実施形態では、生物活性材料はコントラスト増強剤である。
ナノシェルは、電子顕微鏡(SEMおよびTEM)もしくは光散乱測定またはその両方で測定した場合、好ましくは約15nm〜約300nm、約20nm〜約300nm、またはより詳細には約20nm〜約100nmの平均粒度を有する。
他に記載がない限り、本明細書の「シリカ・ナノシェル」という用語は、四価ケイ素材料を含むシェルを含むナノシェルをいう。四価ケイ素は、酸化ケイ素(たとえば、シリカ)の形態もしくは別の四価ケイ素材料の形態またはその両方の形態であってもよい。シリカ・ナノシェルを形成する再現性の高い方法を2つ開示し、これらを図20Aおよび図20Bの反応スキームに図示する。
金属ナノシェルを形成する方法は、i)第1の金属を含む予め形成したシード粒子で星型ポリマー内包複合体を処理することにより、シード系内包複合体を形成するステップ、もしくはii)シード系内包複合体に第2の金属の塩由来の第2の金属を無電解めっきにより付着させることにより、金属ナノシェルを形成するステップ、またはその両方を含む。金属ナノシェルは、1つまたは複数の星型ポリマー内包複合体巨大分子に塗布された金属含有シェルを含む。第1の金属および第2の金属は、同じ金属でも、または別の金属でもよい。予め形成したシードおよびシェルは、金属のイオン形態もしくは非イオン形態またはその両方を含む。金属含有シェルは、連続した多孔性もしくは非多孔性シェルでも、または非連続の多孔性もしくは非多孔性シェルでもよい。
酸化鉄ナノシェルを形成する第1の方法は、星型ポリマー内包複合体を予め形成した酸化鉄粒子で処理することで、星型ポリマー内包複合体の親水性鎖セグメントとの非共有結合性相互作用により結合した酸化鉄ナノ粒子を含む酸化鉄ナノシェルを形成するステップを含む。
以下の例に使用した星型ポリマーは19nmの流体力学的半径を有し、各ポリマーは、ポリスチレン・コア(3kDa)およびジメチルアミノエチルメタクリレート・アーム(6kDaあるいは8kDa)から作られた約33のアームを含んでいた。疎水性ポリスチレン・コアは疎水性有機色素を隔離することができ、ポリアミン・シェルは、鋳型に水溶性部位および核形成部位の両方を与える。この作業では、広い範囲のUV−VISスペクトルにおいて強い吸収特性があるため、非凝集のポルフィリン色素の使用を選択した。
(A)。「保護された」3−(tert−ブチルジメチルシリルオキシ)−1−プロピルを末端に持つポリスチレン星型ポリマー、前駆体1の合成(典型的な手順)。
上述のSP−1の手順を用いて、DMAEMA(2.6g)を使用し、60分の反応時間で星型ポリマーSP−2を調製した。
上述のSP−1の手順を用いて、DMAEMA(2.6g)を使用し、85分の反応時間で星型ポリマーSP−3を調製した。
図5の反応模式図に示すように、星型ポリマー内包複合体は、星型ポリマーに内包されたカーゴ材料を含む。カーゴ材料は、非共有結合性相互作用により結合していても、または共有結合性相互作用により結合していてもよい。この例ではカーゴは疎水性色素である。限定を意図するものではなく、例示のため、図5に示した分子構造は、星型ポリマーに内包された色素の3つの分子を示す。内包されたカーゴ材料の分子数は1つでも、または複数でもよい。疎水性色素は、ポリマー・アームの内側疎水性セグメントおよび疎水性コアと接触していると考えられる。
上述の手順を使用して、星型ポリマーSP−1および下記5,10,15,20−(3,5−ジテルトブチルフェニル)ポルフィリン(M=2H)(DTBP)から星型ポリマー内包複合体OC−1を調製した。
I.金ナノシェルの一般的な調製:
Pham等、Langmuir 2002,18,pages 4915−4920に従い、金シード(平均直径1nm〜3nm)を調製した。要約すると、NaOH(4.5mL、0.2M)を45.5mLのミリポア水に加え、この溶液を2分間600rpmで撹拌した。その後、混合物に、1mLのミリポア水で希釈した80%テトラキス(ヒドロキシメチル)ホスホニウムクロリド(THPC)12マイクロリットルを加え、さらに2分間撹拌した。溶液のpHは約12であった。最終ステップで金(III)クロリド(2mL、0.029M)を速やかに添加した。金(III)クロリドを加えると、溶液は無色から淡褐色に変化した。得られた金シードの溶液をさらに5分間撹拌した。次いで星型ポリマー内包複合体を含む水溶液(5mL)を金シードの水溶液(5mL)と混合した。合わせた溶液を水(10mL)で希釈し、一晩撹拌した。分画分子量(MWCO)12,000Da〜14,000Daのセルロース透析膜を使用して、溶液を水に対して24時間透析した。透析した溶液を4℃で保存することにより、金シード内包複合体が生成された。この方法で形成された金シード内包複合体の三次元図を図5に示す。金(III)クロリド溶液(0.0955M、1.74mL)を98.2mLのミリポア水で希釈し、炭酸カリウム(100mg)を加えた。得られた溶液を暗所で24時間熟成し、以下の成長ステップのための水酸化金(III)溶液を形成した。金成長ステップは、650rpmで1分間ボルテックス撹拌しながら、金シード内包複合体溶液(9mL)の水酸化金溶液(14.8mL)を混合することにより開始した。次いでこの混合物にヒドロキシルアミンヒドロクロリド溶液(0.026%で新たに調製、20mL)を45秒かけて加えた。最終溶液をさらに15分間撹拌し、その後の精製ステップの前に4℃で保存した。金ナノシェル溶液を水に対して24時間、その後メタノールに対して24時間透析した(MWCO12,000Da〜14,000Daのセルロース膜)。金ナノシェル粒子は、凍結乾燥により単離した。
上述の手順を使用して、星型ポリマー内包複合体OC−1から金ナノシェルAuNS−1を調製した。SEM画像から測定したところ、平均粒子直径は110nmであった。図7Aおよび図7Bはそれぞれ、市販されている固体金粒子と金ナノシェルAuNS−1とを比較したSEM画像である。各写真の粒度は同様で、約110nmである。この粒度は、たとえば、薬剤などの生物活性材料のインビボでの全身送達に好適である。AuNS−1ナノ粒子は各々、図7Bの三次元図に示すように、星型ポリマー内包複合体の複数の巨大分子を包み込むと考えられる。図7Aおよび図7BのTEM画像に挿入した画像は、それぞれ固体金ナノ粒子およびAuNS−1ナノ粒子の水溶液である。図7Aの固体金ナノ粒子溶液は、マゼンタである。図7BのAuNS−1溶液は、ダークブルーである。図8は、固体金ナノ粒子とAuNS−1との吸収スペクトルを比較する。固体金ナノ粒子は586nmにピーク吸光度を有したのに対し、AuNS−1は420nm(ポルフィリンDTBP)および778nmにピーク吸光度を有する。AuNS−1溶液のみが、約600nm〜1000nmを超える生体の光学窓で吸収する。
合成条件(たとえば、成長溶液の濃度、星型ポリマー当たりのシードの量もしくは成長時間またはそれらすべて)を変更することにより、様々な金ナノシェル粒度および近赤外(NIR)吸収を達成することができる。以下の実施例2および3は、様々に異なる反応条件パラメータの作用を立証する。
星型ポリマーSP−1(その内包複合体OC−1ではなく)を鋳型として使用し、さらに6mLの金シード星型ポリマーSP−1溶液(9mlのOC−1溶液ではなく)、半分量のヒドロキシルアミン溶液、およびヒドロキシルアミン溶液の添加時間20分を使用した以外は、AuNS−1の形成に使用した上記の手順をAuNS−2の形成にも使用した。
6mLの金シード星型ポリマー内包複合体OC−1溶液、半分量のヒドロキシルアミン溶液、およびヒドロキシルアミン溶液の添加時間5分を使用した以外は、AuNS−3の形成にも、AuNS−1の形成に使用した上記の手順を使用した。表8に、形成される金ナノシェルの平均粒子直径に対する様々に異なる反応パラメータの作用をまとめてある。
金ナノシェルはそれ自体、最初の金ナノシェルを囲む追加シェルを与える第2の成長ステップを開始させるために使用してもよい。たとえば、金ナノシェルAuNS−4については、金「シードした」鋳型OC−1の代わりに金ナノシェルAuNS−2を使用した以外は、AuNS−1の形成に使用した上記の手順を使用して、AuNS−4に第2の追加金ナノシェルを設けて形成した(粒度は、AuNS−2の平均90nmからAuNS−4の平均220nmに増加した)。
図12は、金ナノシェル表面の周りに官能性有機材料の追加表面コーティングを有する星型ポリマー内包複合体の周囲の金ナノシェルの構造を示す三次元図である。
星型ポリマー内包複合体の凝集および金ナノシェルの大きさは、以下の実施例6および7、ならびに図14の三次元図に示すようにpHにより制御することができる。単分子星型ポリマー内包複合体OC−1は、20nm〜25nmの平均粒度を有する。
成長ステップの前に水性HClを添加してpH3.18に調整した金シード溶液を用いた以外は、AuNS−1の形成に使用した上記の手順を用いて、AuNS−6を形成した。
成長ステップの前に水性NaOHを添加してpH8.4に調整した金シード溶液を用いた以外は、AuNS−1の形成に使用した上記の手順を用いて、AuNS−7を形成した。
金ナノシェルの大きさは、以下の実施例8および9に示すように星型ポリマーのペンダント・アミン含有量(DMAEMA)により制御することができる。単分子星型ポリマー内包複合体OC−1からOC−3は、18nm〜24nmの平均粒度を有する。
鋳型が星型ポリマーSP−2(表7)から形成した内包複合体OC−2である以外は、AuNS−1の形成に使用した上記の手順を用いて、AuNS−8を形成した。
鋳型が星型ポリマーSP−3(表7)から形成した内包複合体OC−3である以外は、AuNS−1の形成に使用した上記の手順を用いて、AuNS−9を形成した。AuNS−9は、平均で1〜2個のOC−2の巨大分子を含むと考えられる。
図17〜図18Cは、金ナノシェルAuNS−1に使用した様々な特性評価技術により得られた画像である。図17は、AuNS−1の電子エネルギー損失スペクトル(EELS)であり、挿入画像に示した線に沿ってサンプル中の炭素および金の周期的存在が示され、ナノ粒子の明部は比較的高比率の金を含み、暗い方の領域は、比較的に高比率の炭素を含むことが確認される。暗い方の領域は、直径が約16nm〜18nmである。図18Aは、小塊状の表面トポグラフィを拡大倍率で示す明視野透過型電子顕微鏡写真(BF−TEM)である。図18Bは、走査透過型電子顕微鏡(HAADF−STEM)で取得した高角度散乱暗視野顕微鏡写真であり、AuNS−1ナノシェルの別の詳細なトポグラフィ写真を示す。小塊は約18nmの直径を有し、約16nmの間隔がある。図18Cは、AuNS−1の断面の走査型電子顕微鏡写真である(集束イオンビーム(FIB)ミリングにより生成された断面サンプル)。
図19Aは、星型ポリマー内包複合体OC−1(423nmの単一ピーク)と金ナノシェルAuNS−1(419nmおよび790nmのピーク)とのUV−VIS吸収スペクトルを比較する。図19Bは、420nm励起のOC−1と金ナノシェルAuNS−1との蛍光発光スペクトルを比較する。内包複合体に内包されたポルフィリン色素の蛍光は、金ナノシェル内に保持されている。色素は、星型ポリマー内包複合体および金ナノシェル内で実質的に非凝集状態である。
開示された星型ポリマーは、それらの外側に核形成部位を有するように設計してもよい。そうした星型ポリマーは種々の有機色素と内包複合体を形成できるため、複雑な構造のケイ素系ナノシェルを形成する別の多用途の鋳型となる。
図20Aは、ケイ素ナノシェルを形成する「2ポット」法を分子モデルを用いて図示する。第1のステップでは、適切な星型ポリマー(20mg)およびポルフィリン色素DTPB(2mg)をTHF(20マイクロリットル)に溶解させた。急速撹拌しながら、この混合物をエタノール(4mL)に滴下して加えることにより、内包複合体を作った。図21Aは、この方法で形成した星型ポリマー内包複合体OC−4(Z=10nm)の原子間力顕微鏡画像(AFM)である。この混合物をポリ(テトラフルオロエチレン)(PTFE)フィルタ(0.2マイクロメートル)を使用して濾過し、アリコート(2mL)を、水酸化アンモニウム(30%w/v)をエタノール(1:19v/v、20mL)に溶かした水溶液に加えた。この溶液に、0.15mLの第1のケイ素剤(たとえば、TEOS)を加え、反応物を室温で2時間撹拌した。反応は、粒子の凝集を防ぐため2時間を超えて進行させなかった。ステップ2では、トルエン(300mL)の導入により反応を止めた。溶媒容量を真空下、60℃で濃縮し、最終容量を約10mLとした。次いで官能性オルガノシラン(たとえば、ヘキサメチルジシラザン(HMDS))を加え(1.5mL)、反応物を16時間室温で撹拌した。こうして形成された官能性ケイ素ナノシェルを、メタノールに対する透析(7kDaカットオフ)を繰り返して精製した。ステップ1の図20Aに示すヒドロキシル基は、ナノ粒子のシリケート・ナノシェルに残留する表面結合シラノールOH基である。
星型ポリマー内包複合体OC−4、および上記のような官能性オルガノシリケートとしてのHMDSを出発物質として、上記の「2ポット」手順を使用して、シリカ・ナノシェルを調製した。図21Bは、約25nmの粒度を示すSiSN−1のTEMである。
比較例として、2ポット手順を用いて星型ポリマー内包複合体を使用せずに、固体シリカ粒子を調製した。こうした粒子を図22Aに示す。粒子直径は、約50nm〜250nmの範囲である。
「2ポット」方法は有効であったが、サンプルの処理時間を大幅に短縮した1ポット形態にさらに最適化した。さらに、より反応性の高いケイ素剤を使用した場合、反応時間も大幅に短縮された。
星型ポリマー内包複合体OC−4、および官能性オルガノシリケートとしての3−アミノプロピルジメチルエトキシシランを用い、上述の手順を使用して、シリカ・ナノシェルSiNS−2を調製した。図22Bは、約30nmの平均粒度を有するSiSN−2ナノシェルのSEMである。
以下の実施例13〜16は、シリカ・ナノシェルの粒度を、コーティング時間、コーティング試薬の濃度もしくは星型ポリマーの大きさまたはそれらすべて(こうした様々なパラメータから得られる混合例が示される)により制御することができることを立証する。
第2のオルガノシリケート材料としてDPDSを用い、上記のようなSiNS−1の2ポット法を使用して、SiNS−3を生成した。図23Aは、約25nmの平均粒度を有するSiNS−3ナノシェルのTEMである。
第2のオルガノシリケート材料としてのDPDSおよび伸長反応時間を用い、上記のような1ポット法を使用して、SiNS−4を生成した。図23Bは、約50nmの平均粒度を有するSiNS−4ナノシェルのTEMである。
第2のオルガノシリケート材料としてのDPDSおよび1mlの水酸化アンモニウム溶液を用い、上記のような1ポット法を使用して、SiNS−5を生成した。図24Aは、約75nmの平均粒度を有するSiNS−5ナノシェルのTEMである。
第2のオルガノシリケート材料としてのDPDSおよび1.15mlの水酸化アンモニウム溶液を用い、上記のような1ポット法を使用して、SiNS−2を生成した。図24Bは、約100nmの平均粒度を有するSiNS−6ナノシェルのTEMである。
以下の例は、シリカ・ナノシェルの表面タグ化を立証する。TEOSを用いて1ポット・プロセスで、ポルフィリン内包星型ポリマーをケイ素含有シェルでコーティングし、粒子の表面をアミノプロピルトリメトキシシラン(APTMS)で処理して表面アミン基を導入した。得られた粒子を、代表的な細胞標的化剤としてα−メトキシ−ω−カルボン酸スクシニミジルエステルポリ(エチレングリコール)および塩化ダンシルで連続処理することにより、表面タグ化した。表面機能化は、水に対する十分な透析の前後にUV−VISスペクトルのダンシル成分とポルフィリン成分とを比較して点検した。図25は、連続的なタグ化反応を模式的に示す。
ナノシェルの表面を修飾するには、有機タグ化剤を使用してもよい。アミノ官能性SiNS−2(20mg)をジクロロメタンとトリエチルアミンとの溶液(9:1)に溶解させてから、この反応液に、有機タグ化剤として750DaのPEG平均分子量(0.2g)を有するα−メトキシ−ω−カルボン酸スクシニミジルエステルポリ(エチレングリコール)を加えた。次いで反応液を室温で24時間撹拌してから、第2の有機タグ化剤として塩化ダンシル(0.2g)を加え、次いで反応液をさらに24時間撹拌した後、MeOH、次いで水に対する透析(MWCO=15kDa)により精製した。得られた溶液を凍結乾燥してSiSN−7を粉末として得た。
2000DaのPEG平均分子量を有するα−メトキシ−ω−カルボン酸スクシニミジルエステルポリ(エチレングリコール)を有機タグ化剤として用い、SiNS−7の上述の手順を使用して、タグ化シリカ・ナノシェル、SiNS−8を調製した。
5,000DaのPEG鎖平均分子量を有するα−メトキシ−ω−カルボン酸スクシニミジルエステルポリ(エチレングリコール)を有機タグ化剤として用い、SiNS−7の上述の手順を使用して、タグ化シリカ・ナノシェル、SiNS−9を調製した。
10,000DaのPEG平均分子量を有するα−メトキシ−ω−カルボン酸スクシニミジルエステルポリ(エチレングリコール)を有機タグ化剤として用い、SiNS−7の上述の手順を使用して、タグ化シリカ・ナノシェル、SiNS−10を調製した。
以下の例は、ダンシル化シリカ・ナノシェルが薄いケイ素含有シェル(20nmの粒子)を有する場合、ポルフィリンがタグ化シリカ・ナノシェルから漏出し得、ケイ素含有シェルが厚い(30nmの粒子)場合、ポルフィリン色素が保持され得ることを立証する。
ナノシェルの厚さを制御する伸長反応時間を用い、SiNS−2の上述の手順を使用して、前駆体シリカ・ナノシェルを調製した。前駆体ナノシェル溶液を、ジクロロメタンに対する透析(MWCO=14kDa)によりジクロメタンと溶媒交換してから、塩化ダンシル(0.2g)およびトリエチルアミン(0.2mL)を加えた。反応液を室温で24時間撹拌してから、MeOH、次いで水に対する透析(MWCO=15kDa)により精製した。ナノシェルSiNS−11は、図28AのTEMに示すように30nmの直径を有した。
ナノシェルの厚さを制御する短い反応時間を用い、SiNS−11の上述の手順を使用して、SiNS−12を調製した。SiNS−12のナノシェルは、図28BのTEMに示すように20nmの直径を有した。
オレイル酸およびオレイルアミンの存在下でベンジルエーテル中の鉄(III)アセチルアセトンの熱分解により酸化鉄(Fe3O4、6nm)ナノ粒子を合成し、この界面活性剤安定化酸化鉄ナノ粒子を、S.J.Sun等、J.Am.Chem.Soc.2004,126,273に記載されているようにヘキサンに沈殿させて単離した。
星型ポリマーSP−1を使用した上述の手順を用いて、酸化鉄ナノシェルSPIONNS−1水を生成した。図30Aは、SPIONNS−1のTEMである。図30Bは、赤錆色の色合いを有する水溶液(左)および褐色の凍結乾燥粉末(右)のSPIONNS−1の一対の写真である。この溶液は、図31の吸収曲線に示すように420nmおよび550nmにUV−VISのピークを有し、650nmおよび720nmの発光ピーク(420nmの励起)を有する。
Claims (40)
- i)6つ以上の独立したポリマー・アームに共有結合した架橋コアを有する両親媒性単分子星型ポリマー、およびii)前記星型ポリマーに内包されたカーゴ材料を含む星型ポリマー内包複合体;および
前記星型ポリマー内包複合体の外側表面と接触した無機材料を含むシェル
を含むナノシェル。 - i)前記コアは疎水性であり、ii)前記カーゴ材料は疎水性であり、かつiii)前記6つ以上のポリマー・アームは別々に、a)前記コアに共有結合した疎水性鎖セグメントおよびb)前記疎水性鎖セグメントに結合した外側親水性鎖セグメントを含む、請求項1に記載の組成物。
- 前記ナノシェルは前記星型ポリマー内包複合体の2つ以上の巨大分子を含む、請求項1に記載の組成物。
- 前記シェルは1つまたは複数のシェル層を含む、請求項1に記載の組成物。
- 前記1つまたは複数のシェル層は多孔性である、請求項4に記載の組成物。
- 前記シェルは四価ケイ素材料もしくは金属またはその両方を含む、請求項1に記載の組成物。
- 前記ナノシェルは約15nm〜約300nmの平均直径を有する、請求項1に記載の組成物。
- 前記カーゴ材料は造影剤である、請求項1に記載の組成物。
- 前記造影剤はポルフィリノイド化合物であり、前記ポルフィリノイド化合物は実質的に非凝集である、請求項8に記載の組成物。
- 前記カーゴ材料は生物活性化合物である、請求項1に記載の組成物。
- 前記生物活性化合物は薬剤である、請求項10に記載の組成物。
- 前記シェルは連続している、請求項1に記載の組成物。
- 前記シェルは金を含む、請求項1に記載の組成物。
- 前記シェルはシリカを含む、請求項1に記載の組成物。
- 前記シェルは酸化鉄を含む、請求項1に記載の組成物。
- 前記シェルに共有結合した有機表面基をさらに含む、請求項1に記載の組成物。
- 前記有機表面基は色素、ポリ(アルキレンオキシド)鎖セグメント、ポリ(アルキレンイミン)鎖セグメント、生物活性部分、およびこれらの組み合わせからなる群から選択される化学部分を含む、請求項16に記載の組成物。
- 両親媒性単分子星型ポリマーであって、6つ以上の独立したポリマー・アームに共有結合した架橋コアを有する前記星型ポリマーとカーゴ材料との混合物を第1の溶媒中で形成するステップ;
前記カーゴ材料の非溶媒である第2の溶媒に前記混合物を注入することにより、前記星型ポリマーに内包された前記カーゴ材料を含む星型ポリマー内包複合体を形成するステップ;および
1つまたは複数の連続的プロセスを用いて前記星型ポリマー内包複合体の外側表面にシェル形成無機材料を付着させることにより、1つまたは複数の無機シェル層を含むシェルを含むナノシェルを形成するステップ
を含む方法。 - 前記ナノシェルを1つまたは複数の有機タグ化剤で処理することにより、タグ化ナノシェルであって、前記タグ化ナノシェルのシェル表面に共有結合した1つまたは複数の有機表面基を含むタグ化ナノシェルを形成するステップをさらに含む、請求項18に記載の方法。
- i)前記コアは疎水性であり、ii)前記カーゴ材料は疎水性であり、かつiii)前記6つ以上のポリマー・アームは別々に、a)前記コアに共有結合した疎水性鎖セグメントおよびb)前記疎水性鎖セグメントに結合した外側親水性鎖セグメントを含む、請求項18に記載の方法。
- 前記ナノシェルは前記星型ポリマー内包複合体の2つ以上の巨大分子を含む、請求項18に記載の方法。
- 前記星型ポリマーは有機触媒開環重合により形成される、請求項18に記載の方法。
- 前記星型ポリマーはポリカーボネート鎖セグメント、ポリエステル鎖セグメント、またはこれらの組み合わせを含む、請求項22に記載の方法。
- 前記カーゴ材料はポルフィリノイド化合物である、請求項18に記載の方法。
- 前記カーゴ材料は薬剤である、請求項18に記載の方法。
- 前記シェルは金を含む、請求項18に記載の方法。
- 前記星型ポリマー内包複合体の外側表面にシェル形成無機材料を付着させる前記ステップは、i)予め形成した金シードで前記星型ポリマー内包複合体を処理することにより、シード内包複合体を形成するステップ、およびii)無電解付着により前記シード内包複合体に金を付着させることにより、前記ナノシェルを形成するステップを含み、前記ナノシェルは金を含むシェルを含む、請求項18に記載の方法。
- 前記シェルはシリカを含む、請求項18に記載の方法。
- 前記星型ポリマー内包複合体の外側表面にシェル形成無機材料を付着させる前記ステップは、i)第1の溶媒中で前記星型ポリマー内包複合体を第1の四価ケイ素材料で処理することにより、前駆体シリカ・ナノシェルを形成するステップ、ii)第2の溶媒中で前記前駆体シリカ・ナノシェルを第2の四価ケイ素材料で処理することにより、ナノシェルを形成するステップを含み、前記ナノシェルは四価ケイ素材料を含むシェルを含む、請求項18に記載の方法。
- 前記第1の四価ケイ素剤はオルガノシリケートであり、前記第2の四価ケイ素剤はオルガノジシラザンである、請求項29に記載の方法。
- 求核基を含む四価ケイ素化合物で前記ナノシェルを処理することにより、アミン、チオール、アルコール、およびこれらの組み合わせからなる群から選択される求核性表面基を含む修飾シェルを含む修飾ナノシェルを形成するステップをさらに含む、請求項29に記載の方法。
- 反応して前記求核性表面基と共有結合を形成することができる有機タグ化剤で前記修飾ナノシェルを処理することにより、タグ化ナノシェルを形成するステップをさらに含む、請求項31に記載の方法。
- 前記有機タグ化剤は色素、ポリ(アルキレンオキシド)鎖セグメント、ポリ(アルキレンイミン)鎖セグメント、生物活性化合物、およびこれらの組み合わせからなる群から選択される、請求項32に記載の方法。
- 前記シェルは酸化鉄を含む、請求項18に記載の方法。
- 前記星型ポリマー内包複合体の外側表面にシェル形成無機材料を付着させる前記ステップは、前記星型ポリマー内包複合体を酸化鉄ナノ粒子で処理することにより、前記ナノシェルを形成するステップを含み、前記ナノシェルは酸化鉄ナノ粒子を含むシェルを含む、請求項18に記載の方法。
- 前記ナノシェルは約15nm〜約300nmの平均直径を有する、請求項18に記載の方法。
- 好適な溶媒中に両親媒性単分子星型ポリマーであって、6つ以上の独立したポリマー・アームに共有結合した架橋コアを有する前記星型ポリマー、カーゴ材料、および酸化鉄ナノ粒子を含む混合物を形成するステップ;および
前記カーゴ材料の非溶媒である第2の溶媒に前記混合物を注入することにより、前記星型ポリマー、前記カーゴ材料、および前記酸化鉄粒子を含むナノシェルを形成するステップ
を含む方法。 - 前記ナノシェルは約15nm〜約300nmの平均直径を有する、請求項37に記載の方法。
- 請求項1に記載のナノシェルを含む水性混合物。
- 請求項37に記載の水性混合物と細胞を接触させるステップを含む、画像診断法。
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