JP2021504096A - 活性化表面に結合した接着層 - Google Patents
活性化表面に結合した接着層 Download PDFInfo
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- JP2021504096A JP2021504096A JP2020548869A JP2020548869A JP2021504096A JP 2021504096 A JP2021504096 A JP 2021504096A JP 2020548869 A JP2020548869 A JP 2020548869A JP 2020548869 A JP2020548869 A JP 2020548869A JP 2021504096 A JP2021504096 A JP 2021504096A
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Abstract
Description
本出願は2017年11月30日に出願された米国仮出願第62/592,880号の利益を主張し、その開示全体は、あらゆる目的のために参照により本明細書に組み込まれる。
本発明は、そうでなければ非反応性の表面の活性化の分野に関し、それらをコーティングの化学結合に対して感受性にし、コーティングは表面特性の改変を可能にする。このようなコーティングされた表面は、細胞増殖、再建医療、および医療デバイスのための足場としての有用性を有する。
定義
ここでいう「共有結合」とは原子間の電子対の共有を伴う化学結合のことを指す。「配位」、「配位子」または「配位共有」結合の用語は金属イオンのリガンドへの結合など、両方の電子が同じ原子に由来する2中心2電子共有結合をいう。反対に、「イオン」結合は、反対に帯電したイオン間の静電引力をいい、電子は共有されないが、1つ以上の電子が原子の一方(アニオン)に局在し、他方の原子(カチオン)から除去される。
本発明の方法は、そうでなければ反応性金属アルコキシドと非反応性であるポリマーまたは金属表面上で使用することができる。したがって、コーティングの結合に反応しないホスホネートまたはシロキサンのようなポリマーおよび他の材料の酸化またはアミノ化は、過マンガン酸塩、亜塩素酸塩、クロム酸、クロム酸塩、他のクロム酸誘導体、四酸化オスミウム、四酸化ルテニウム、ヨウ素酸塩、過酸塩、過酸化物、フェントン試薬(過酸化水素/Fe(II))、四酢酸鉛、四酢酸鉛/Mn(II)、オゾン、および酸素のような化学酸化剤を用いる化学酸化法を含む酸化法を通して活性化することができる。他の方法には、酸素または窒素プラズマ放電およびコロナ放電が含まれる。酸素プラズマ活性化はDongらの米国特許出願公開第2013/0005660号に記載されているように、またはClevengerらの米国特許第9,655,992号に記載されているように達成することができ、その両方は、その全体が参照により本明細書に組み込まれる。これらの化学試薬および方法は、表面上に水酸基(−OH)、オキシ(−O−)、オキソ(=O)、カルボニル(C=O)、カルボン酸(−C(=O)−OH)またはカルボン酸(−C(=O)−O−)官能基、または窒素プラズマではアミノ基(−NH2)を生成することができる。次いで、このような官能基は無機アルコキシド(例えば、ZrアルコキシドまたはTiアルコキシド)と反応して、化学的に結合した無機接着層を形成し得る。適切な非反応性ポリマーは、ポリマー表面上に適切な反応性官能基、例えば前述のヒドロキシル、オキシ、オキソ、カルボニル、カルボン酸またはカルボン酸塩官能基を欠いているために非反応性である。好適な不活性化ポリマーには、以下が含まれる:
C−H結合酸化によって反応性であるC−OHまたはCOOH基(アルコールまたは酸)を生じる、ポリシロキサンのような末端アルキル基を有するポリアルカンまたは他のポリマー;
C−H結合の活性化が酸化的に起こるポリアルキルアレーンやポリアルデヒド;
酸化によってグリコールを生じるポリオレフィン;
酸化によってスルホン酸を生じるポリチオール;および
酸化によってホスホン酸、ホスフィン酸またはリン酸を生じるポリホスフィン。
ポリジメチルシロキサン(PDMS)試験片を片側で酸素プラズマ酸化し、10μL/mLの濃度でトルエン中のチタンイソプロポキシドの溶液に浸漬した。試料を溶液中に15分間浸漬した。試験片を溶液から取り出したところ、これらのPDMS試験片の表面はわずかに半透明性が低くなったことが認められた。試験片を35℃で1分間加熱し、エタノールでリンスし、次いで、0.5mg/mLの濃度のトルエン中のオクタデシルホスホン酸(ODPA)の溶液中に置いた。試験片をこの溶液中に数時間保持し、溶液から取り出し、35℃で1分間加熱し、エタノールでリンスした。試験片表面の外観は、この手順の間に変化しなかった。赤外スペクトル分析は、PDMS表面上にオクタデシルホスホネートの単層の存在を示した(図1)。大きなピークはPDMSメチル基に起因する;2921及び2851cm−1のピークは、オクタデシルホスホネート(ODPA)の自己集合単分子層に特徴的である。対照的に、接着層を形成するためにチタンイソプロポキシドで前処理されなかった対照PDMS試験片は、類似のODPA処理後にホスホネートSAMの証拠を示さなかった。同様の結果が、11−ヒドロキシウンデシルホスホン酸を用いて観察された。
一般.全ての材料は、商業的供給源から調達した。溶媒および化学試薬としては、無水トルエン(Sigma Aldrich)、tert−ブタノール(Fisher Scientific)、200プルーフエタノール(Acros Organics)、試薬アルコール(Fisher Scientific)、チタン(IV)ブトキシド(Sigma Aldrich)、モノアミン官能化トリアルコキシシランおよびホスホネート(Gelest, Sikemia)、ヘパリンナトリウム塩(Sigma Aldrich)が挙げられる。
上記の説明から、当業者は本発明の本質的な特徴を容易に確認することができ、本発明の精神および範囲から逸脱することなく、本発明を様々な用途および条件に適応させるために、本発明の様々な変更および修正を行うことができる。したがって、他の実施形態も本特許請求の範囲内である。
Claims (45)
- a)化学的にアクセス可能な反応性官能基を含む活性化表面;
およびb)前記活性化表面の前記反応性官能基に化学的に結合した無機アルコキシド接着層を備え、
ここで、前記反応性官能基は無機アルコキシドと反応して前記無機接着層を形成し;そして前記無機接着層は、全体の表面特性を改変する部分のさらなる付着のためのさらなる官能基を提供する、構造体。 - 前記活性化表面が無機接着層の化学結合に対して本質的に非反応性な表面を含み、本質的に非反応性な表面が前記表面上に化学的に接近可能な反応性官能基を生成し、それによって活性化を提供するように処理されている、請求項1に記載の構造体。
- 前記表面が、ポリマー、ステンレス鋼、またはステンレス鋼合金を含む、請求項1または2に記載の構造体。
- 前記ポリマーが、ポリアルカン、ポリシロキサン、ポリアルキルアレーン、ポリオレフィン、ポリチオールおよびポリホスフィンからなる群から選択される、請求項3に記載の構造体。
- 前記表面反応性官能基が、ヒドロキシル基、オキシ基、オキソ基、カルボニル基、カルボン酸基、カルボキシレート基、およびアミノ基からなる群から選択される、請求項1〜4のいずれか1項に記載の構造体。
- 前記表面反応性官能基が化学酸化によって生成される、請求項5に記載の構造体。
- 前記化学酸化が、過マンガン酸塩、亜塩素酸塩、クロム酸、クロム酸塩、四酸化オスミウム、四酸化ルテニウム、ヨウ素酸塩、過酸、過酸化物、フェントン試薬、四酢酸鉛、鉛四酢酸塩/Mn(II)、オゾン、および酸素からなる群から選択される酸化剤による処理を含む、請求項6に記載の構造体。
- 前記表面反応性官能基が、酸素プラズマ放電、窒素プラズマ放電、またはコロナ放電によって生成される、請求項5に記載の構造体。
- 前記無機接着層が、Ti、Zr、Al、Mg、Si、Zn、Mo、Nb、Ta、Sn、W、V、およびそれらの2つ以上の混合物の酸化物からなる群から選択される無機酸化物を含む、請求項1〜4のいずれか1項に記載の構造体。
- 前記無機酸化物接着層が、Al、Ti、Zr、Si、Mg、Znの酸化物、およびそれらの2つ以上の混合物からなる群から選択される、請求項9に記載の構造体。
- 前記無機接着層の付加官能基に結合した自己集合単分子層(SAM)をさらに含み、前記SAMが、ホスホン基、カルボン酸基、スルホン酸基、ホスフィン酸基、リン酸基、スルフィン酸基、またはヒドロキサム酸基を含む有機化合物から選択される、請求項1〜10のいずれか一項に記載の構造体。
- 前記SAMが、ホスホネートの自己集合単分子層(SAMP)を含む、請求項11に記載の構造体。
- 前記ホスホネートが、疎水性ホスホネートおよび細胞接着性ホスホネートからなる群から選択される、請求項12に記載の構造体。
- 前記疎水性および細胞接着性ホスホネートは以下の構造のホスホン酸からなる群から選択され、
ここで、R基は任意に置換されたアルキル、任意に置換されたヘテロアルキル、任意に置換されたアルケニル、任意に置換されたヘテロアルケニル、任意に置換されたアルキニル、任意に置換されたヘテロアルキニル、任意に置換されたアリール、任意に置換されたアリールアルキル、任意に置換されたヘテロアリール、および任意に置換されたヘテロアリールアルキルからなる群から選択することができ、ここで、ヘテロアルキル、ヘテロアルケニル、ヘテロアルキニル、ヘテロアリール、およびヘテロアリールアルキルはO、NおよびSからなる群から選択される1つ以上のヘテロ原子を含有する、請求項13に記載の構造体。 - 前記疎水性ホスホネートがR=C3−C30アルキルからなる群から選択され、前記細胞接着性ホスホネートがさらなるホスホネート基で置換されたR=C3−C30アルキルからなる群から選択される、請求項14に記載の構造体。
- 前記細胞接着性ホスホネートが、C3−C30α,ω−ジホスホネートからなる群から選択される、請求項15に記載の構造体。
- 前記SAMまたはSAMPが、それに共有結合した抗感染剤または抗血栓形成剤をさらに含む、請求項11〜16のいずれか1項に記載の構造体。
- 前記抗感染剤が、アミカシン、ゲンタマイシン、カナマイシン、ネオマイシン、ネチルマイシン、トブラマイシン、パロモマイシン、ゲルダナマイシン、ハービマイシン、ロラカルベフ、エルタペネム、ドリペネム、イミペネム/シラスタチン、メロペネム、セファドロキシル、セファゾリン、セファロチン、セファレキシン、セファクロル、セファマンドール、セフォキシチン、セフプロジル、セフロキシム、セフジトレン、セフォペラゾン、セフォタキシム、セフポドキシム、セフタジジム、セフチブテン、セフチゾキシム、セフトリアキソン、セフェピム、セフタロリンフォサミル、セフトビプロール、テイコプラニン、バンコマイシン、テラバンシン、クリンダマイシン、リンコマイシン、ダプトマイシン、アジスロマイシン、クラリスロマイシン、ジリスロマイシン、エリスロマイシン、ロキシスロマイシン、トロレアンドマイシン、テリスロマイシン、スペクチノマイシン、スピラマイシン、アズトレオナム、フラゾリドン、ニトロフラントイン、アモキシシリン、アンピシリン、アズシシリン、カルベニシリン、クロキサシリン、ジクロキサシリン、フルクロキサシリン、メゾシリン、メチシリン、ナフシリン、オキサシリン、ペニシリンG、ペニシリンV、ピペラシリン、テモシリン、チカルシリン、アモキシシリン/クラブラン酸、アンピシリン/スルバクタム、ピペラシリン/タゾバクタム、チカルシリン/クラブラン酸、バシトラシン、コリスチン、ポリミキシンb、シプロフロキサシン、エノキサシン、ガチフロキサシン、レボフロキサシン、ロメフロキサシン、モキシフロキサシン、ノルリジキシ酸、ノルフロキサシン、オフロキサシン、トロバフロキサシン、グレパフロキサシン、スパルフロキサシン、テマフロキサシン、マフェニド、スルフォナミドクリソイジン、スルファセタミド、スルファジアジン、銀、スルファジアジン、スルファメチゾール、スルファメトキサゾール、スルファニルイミド、スルファサラジン、スルフィソキサゾール、トリメトプリム、トリメトプリム−スルファメトキサゾール、デメクロサイクリン、ドキシサイクリン、ミノサイクリン、オキシテトラサイクリン、テトラサイクリン、クロファジミン、ダプソン、カプレオマイシン、シクロセリン、エタンブトール、エチオナミド、イソニアジド、ピラジナミド、リファンピシン、リファブチン、リファペンチン、ストレプトマイシン、アルスフェナミン、クロラムフェニコール、フォスフォマイシン、フシジン酸、リネゾリド、メトロニダゾール、ムピロシン、プラテンシマイシン、キヌプリスチン/ダルフォプリスチン、リファキシミン、チアムフェニコール、チゲサイクリン、チニダゾール、それらの許容される塩、およびそれらの2つ以上の混合物からなる群から選択される抗菌剤である、請求項17に記載の構造体。
- 前記抗感染剤が、多糖類、キトサン、部分的にアセチル化されたキトサン、ポリグルコサミン、キトサンジオール、ポリオール、アミノアルコール、およびそれらの2つ以上の混合物からなる群から選択される、請求項17に記載の構造体。
- 前記抗感染剤が、クロルヘキシジン、ビグアニド、カチオン性アンモニウム化合物、カチオン性アンモニウムデンドリマー、銀、銅、カチオン種、およびそれらの2つ以上の混合物からなる群から選択される、請求項17に記載の構造体。
- 前記カチオン性アンモニウム化合物が、コリンおよびコリン誘導体からなる群から選択される、請求項20に記載の構造体。
- 前記構造体の被覆表面に付着した細胞をさらに含み、前記細胞は、線維芽細胞、内皮細胞、ケラチノサイト、骨芽細胞、軟骨芽細胞、軟骨細胞、肝細胞、マクロファージ、心筋細胞、平滑筋細胞、骨格筋細胞、腱細胞、靭帯細胞、上皮細胞、幹細胞、神経細胞、PC12細胞、神経支持細胞、シュワン細胞、放射状グリア細胞、神経球を形成する細胞、神経腫瘍細胞、膠芽細胞腫細胞および神経芽細胞腫細胞からなる群から選択される、請求項16に記載の構造体。
- 前記線維芽細胞がNIH 3T3線維芽細胞を含む、請求項22に記載の構造体。
- 細胞外マトリックス(ECM)をさらに含む、請求項22または23に記載の構造体。
- 脱細胞化されてECMを残す、請求項24に記載の構造体。
- a)無機接着層の化学結合に対して本質的に非反応性である表面を提供する工程;
b)前記非反応性である表面を処理して前記表面上に反応性官能基を生成し、それによって活性化表面を提供することによって、無機接着層の化学結合に対する前記本質的に非反応性である表面を活性化する工程;およびc)前記活性化表面の前記反応性官能基に無機接着層を化学結合する工程を含み、
ここで、前記反応性官能基は無機アルコキシドと反応し、前記無機接着層を形成し;そして前記無機接着層は、全体の表面特性を改変する部分のさらなる付着のためのさらなる官能基を提供する、請求項1または2に記載の構造体を形成する方法。 - 前記表面がポリマーを含む、請求項26に記載の方法。
- 前記ポリマーが、ポリアルカン、ポリシロキサン、ポリアルキルアレーン、ポリオレフィン、ポリチオールおよびポリホスフィンからなる群から選択される、請求項27に記載の方法。
- 前記表面官能基が、ヒドロキシル基、オキシ基、オキソ基、カルボニル基、カルボン酸基、カルボキシレート基、およびアミノ基からなる群から選択される、請求項26〜28のいずれか1項に記載の方法。
- 前記活性化工程が化学酸化を含む、請求項29に記載の方法。
- 前記化学酸化は、過マンガン酸塩、亜塩素酸塩、クロム酸、クロム酸塩、四酸化オスミウム、四酸化ルテニウム、ヨウ素酸塩、過酸塩、過酸化物、フェントン試薬、四酢酸鉛、四酢酸鉛/Mn(II)鉛、オゾン、および酸素からなる群から選択される酸化剤による処理を含む、請求項30に記載の方法。
- 前記活性化工程が、酸素プラズマ放電、窒素プラズマ放電、またはコロナ放電を含む、請求項29に記載の方法。
- 前記無機接着層が、Ti、Zr、Al、Mg、Si、Zn、Mo、Nb、Ta、Sn、W、V、およびそれらの2つ以上の混合物の酸化物からなる群から選択される無機酸化物を含む、請求項26〜29のいずれか1項に記載の方法。
- 前記無機酸化物接着層が、Al、Ti、Zr、Si、Mg、Zn、およびそれらの2つ以上の混合物の酸化物からなる群から選択される、請求項33に記載の方法。
- 非活性な基材表面を活性化し、無機酸化物接着層でコーティングする方法であって、
a)活性化された基材を形成するために前記表面上に反応性官能基を生成させることによって、無機接着層の化学結合に非活性な基材の表面を活性化する工程;
b)溶媒中に溶解および/または分散される反応性無機化合物を含有する有機溶媒を含むコーティング混合物を提供する工程;および
c)前記反応性官能基を前記無機化合物と反応させ、前記基材の活性化表面上に無機酸化物コーティングを形成するのに十分な時間および温度で、前記コーティング混合物中に前記活性化基材を懸濁させて、無機酸化物接着層でコーティングされた基材を提供する工程を含み、
ここで、前記無機化合物は、Ti、Zr、Al、Mg、Si、Zn、Mo、Nb、Ta、Sn、W、及びVのアルコキシドからなる群から選択される、方法。 - 前記活性化工程が化学酸化を含む、請求項35に記載の方法。
- 前記化学酸化が、過マンガン酸塩、亜塩素酸塩、クロム酸、クロム酸塩、テトロキシドオスミウム、テトロキシドルテニウム、ヨウ素酸塩、過酸塩、過酸化物、フェントン試薬、四酢酸鉛、四酢酸鉛/Mn(II)鉛、オゾン、および酸素からなる群から選択される酸化剤による処理を含む、請求項36に記載の方法。
- コーティング工程b)およびc)が、前記活性化基材の表面上への無機アルコキシドの蒸着、および前記反応性官能基と前記無機アルコキシドとの反応によって置き換えられ、それに結合された無機酸化物接着層を形成する、請求項35に記載の方法。
- 前記活性化工程が、酸素プラズマ放電、窒素プラズマ放電またはコロナ放電を含む、請求項35に記載の方法。
- d)コーティング溶液からコーティングされた基材を除去し;
e)溶媒でリンスして、リンス、コーティングされた基材を提供し;および
f)リンス、コーティングされた基材を35〜40℃に加熱する、をさらに含む、請求項35〜37または39のいずれか1項に記載の方法。 - 前記R基がドデシル−9−イニルであり、金属触媒反応を用いてアルキン官能基でさらにカップリングされる、請求項14に記載の構造体。
- 前記R基がドデシル−9−イニルであり、クリック反応を用いてアルキン官能基でさらにカップリングされる、請求項14に記載の構造体。
- 前記無機接着層が電気化学的に活性な部分、光化学的に活性な部分、細胞誘引性部分、細胞接着性部分および抗感染性部分からなる群から選択される有機部分に、介在SAMまたはSAMP層なしで直接付着される、請求項1または2に記載の構造体。
- 前記抗感染性部分が、多糖類、キトサン、部分的にアセチル化されたキトサン、ポリグルコサミン、キトサンジオール、ポリオール、アミノアルコール、およびそれらの2つ以上の混合物からなる群から選択される、請求項43に記載の構造体。
- 前記抗血栓剤がヘパリンである、請求項17に記載の構造体。
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