JP2019073561A - 経皮薬物送達のためのイオン性液体 - Google Patents
経皮薬物送達のためのイオン性液体 Download PDFInfo
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- JP2019073561A JP2019073561A JP2019030302A JP2019030302A JP2019073561A JP 2019073561 A JP2019073561 A JP 2019073561A JP 2019030302 A JP2019030302 A JP 2019030302A JP 2019030302 A JP2019030302 A JP 2019030302A JP 2019073561 A JP2019073561 A JP 2019073561A
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Abstract
Description
本願は、2013年11月3日に出願した仮出願である米国出願第61/899,294号に対する優先権を主張する。この出願の開示は、その全体が本明細書中に参考として援用される。
本発明の分野は、経皮薬物送達製剤と、感染症の処置などのために局所的に投与される製剤と、これらの製剤およびデバイスを作製し使用するための方法である。
局所的および経皮的薬物送達は、経口、皮下、および静脈内のような他の一般的な送達経路に勝る、多くの利点をもたらす。これらの利点には、GI管に関連した主要な分解経路の回避、全身毒性に関連した副作用の低減、および無針薬物投与が含まれる。Brownら、「Dermal and transdermal drug delivery systems: current and future prospects」、Drug Delivery、13巻:175〜87頁(2006年)。残念ながら、皮膚の最外層、角質層(SC:stratum corneum)は、ほとんどの異物に対する障壁として機能し、多くの分子の受動的拡散を厳しく制限する。この障壁を克服するために、化学浸透増強剤(CPE:chemical penetration enhancers)の使用を含めたいくつかの戦略が用いられてきた。CPEは、SC内の脂質組成物および組織を破壊することにより、様々な分子に関して皮膚を通る輸送を増強することが示されてきた。Karandeら、「Design principles of chemical penetration enhancers for transdermal drug delivery」、Proceedings of the National Academy of Sciences of the United States of America、102巻:4688〜93頁(2005年)。しかし、脂質破壊の程度は、皮膚の刺激にしばしば密接に相関する。Karande 2005年。したがって、輸送の増強と皮膚の刺激との間のバランスは、CPEをベースにした薬物製剤を商業化することができる前に、しばしば必要とされる。
特定の実施形態では、例えば以下が提供される:
(項目1)
イオン性液体と、送達される薬物とを含む、経皮薬物送達のための組成物であって、皮膚の表面に適用するときに非刺激性である組成物。
(項目2)
イオン性液体を含む、細菌性感染症を処置するための組成物であって、皮膚の表面に適用するときに非刺激性である組成物。
(項目3)
前記イオン性液体が、少なくとも1つのアニオン成分と少なくとも1つのカチオン成分とを含む、項目1から2のいずれか一項に記載の組成物。
(項目4)
送達される薬物または項目1に記載の組成物をさらに含み、該薬物がイオン性である、項目2に記載の組成物。
(項目5)
前記アニオン成分およびカチオン成分の少なくとも1つが、他の成分の非存在下で適用するときに前記皮膚に対して刺激性である、項目3に記載の組成物。
(項目6)
エマルジョンまたはマイクロエマルジョンの形態をとらない、項目1から5のいずれか一項に記載の組成物。
(項目7)
液体の形態をとる、項目1から6のいずれか一項に記載の組成物。
(項目8)
前記イオン性液体中の前記成分が、好ましくは1:1のモル比にある、[P(C14H29)(C6H13)3]+(「PR4」)と脂肪酸塩、好ましくはオレイン酸ナトリウムまたはヘキサン酸ナトリウムである、項目1から7のいずれか一項に記載の組成物。
(項目9)
前記イオン性液体中の前記成分が、好ましくは1:1から1:2(カチオン成分対アニオン成分)に及ぶモル比にある、カチオン成分と、ゲラン酸の塩とである、項目1から7のいずれか一項に記載の組成物。
(項目10)
前記イオン性液体中の前記成分が、好ましくは1:1のモル比にある、PR4と、ゲラン酸の塩とである、項目1から7のいずれか一項に記載の組成物。
(項目11)
送達される前記薬物が、前記イオン性液体の非存在下よりも該イオン性液体の存在下でより安定である、項目1および3から10のいずれか一項に記載の組成物。
(項目12)
表面での微生物成長を阻害するための方法であって、該表面に、項目2から11のいずれか一項に記載の組成物を、微生物成長を防止するまたは低減させるのに有効な量で適用するステップを含む方法。
(項目13)
前記表面が、埋め込み可能な医療用デバイス上にある、項目12に記載の方法。
(項目14)
薬物を経皮的に送達するための方法であって、皮膚部位の表面に、項目1および3から11のいずれか一項に記載の組成物を投与するステップを含む方法。
(項目15)
前記イオン性液体が、ドデシルジメチルアンモニオプロパンスルホネート、N−ラウリルサルコシネート、およびゲラニオールからなる群から選択されるアニオン成分を含む、項目14に記載の方法。
(項目16)
前記イオン性液体が、ベンジルピリジニウムクロリド、コリン、およびホスホニウムからなる群から選択されるカチオン成分を含む、項目14に記載の方法。
(項目17)
皮膚感染症を処置するための方法であって、処置を必要とする皮膚部位の表面に、項目2から11のいずれか一項に記載の組成物を、該皮膚からバイオフィルムを除去するのに有効な量で投与するステップを含む方法。
(項目18)
前記イオン性液体が、ビストリフルイミド、ゲラン酸の塩、オレイン酸の塩、およびヘキサン酸の塩からなる群から選択されるアニオン成分を含む、項目17に記載の方法。
(項目19)
前記イオン性液体が、テトラアルキルホスホニウム、ベンゼトニウム、および亜鉛からなる群から選択されるカチオン成分を含む、項目17に記載の方法。
(項目20)
皮膚の疾患または障害を処置するための方法であって、処置を必要とする皮膚部位の表面に、項目2から11のいずれか一項に記載の組成物を有効量で投与するステップを含み、該皮膚の疾患または障害が、アトピー性皮膚炎、にきび、創傷、発疹、毛包炎、フルンケル症、カルブンケル症、真菌感染症、および感染症由来のその他の疾患からなる群から選択される方法。
組成物は、ニートのイオン性液体を含有し、これは標準的な貯蔵および適用条件下(例えば、室温および圧力)でエマルジョンもマイクロエマルジョンも形成せずまたは含有しない。イオン性液体は、典型的には、少なくとも1つのカチオン成分および少なくとも1つのアニオン成分を含有する。好ましくは、イオン性液体の成分の少なくとも1つは、化学浸透増強剤であり、好ましくはカチオン成分およびアニオン成分の両方が化学浸透増強剤である。組成物は、好ましくは、送達される薬物も含有する。任意選択で、イオン成分の1つは、送達される薬物でもある。
組成物は少なくとも2つの成分を含有し、それは少なくとも2つのイオン成分であり得るか、または少なくとも1つのイオン成分および送達される薬物であり得る。好ましくは、イオン性液体は、2つまたはそれ超の、より好ましくは2つのイオン成分を含有する。一部の実施形態では、組成物は、経皮的に送達される薬物も含有する。組成物は、広範な薬物を投与するのに使用されてもよい。一部の実施形態では、ILは、細菌性バイオフィルムを皮膚部位から除去する際に有効である。これらの実施形態では、任意選択で、組成物は、送達される追加の薬物を含有しない。一部の実施形態では、組成物は、微生物の成長を阻害するために、医療用デバイスの表面などの合成表面に適用する。
本明細書で使用される「イオン性液体(IL:ionic liquid)」という用語は、室温
で液体状態にある、有機塩または有機塩の混合物を指す。この種類の溶媒は、工業的な処理、触媒、医薬品、および電気化学を含めた様々な分野で有用であることが示されてきた。イオン性液体は、少なくとも1種のアニオン成分および少なくとも1種のカチオン成分を含有する。任意選択で、ILは、追加の水素結合ドナー(即ち、−OH基または−NH基を提供することができる任意の分子)を含有し、その例には、アルコール、脂肪酸、およびアミンが含まれるが、これらに限定するものではない。
に対する国際特許出願公開番号WO07/124397に記載されている。抗菌特性を有する例示的なイオン性液体は、参照によりその全体が本明細書に組み込まれるGrinstaff
らに対するWO2011/056545に記載されている。
ノリン、タジン、オキサジン、およびアザアンヌレンからなる群から選択される複素環を、出現するごとに独立して含有する有機カチオンを含んでいてもよい。イオン性液体は、非環式有機カチオン、例えばアミン、例えばアミジン、イミン、グアニジン、ホスフィン、例えばホスフィニミン、アルシン、スチビン、エーテル、チオエーテル、およびセレノエーテルを含んでいてもよい。
る。DESは、融点が個々の成分のいずれかよりも非常に低い共晶物を形成する混合物で構成される、特殊な性質を持つイオン性溶媒の一種である。例示的なDESには、オレイン酸コリン、ヘキサン酸コリン、ゲラン酸コリン、マロン酸コリン(choline malonate
)(マロン酸コリン二ナトリウム(choline disodium malonate))、および尿素−コ
リンが含まれるが、これらに限定するものではない。これらの中で、製剤はDESであり真のイオン性液体ではないが、それは過剰なカルボキシレートが1:1のイオン対を排除するからである。
酸(henatriacontylic acid)、ラセロイン酸、プシリン酸、ゲダ酸、セロプラスチン酸、またはヘキサトリアコンチル酸(hexatriacontylic acid)が含まれるが、これらに限定するものではない。好ましい脂肪酸塩には、オレイン酸ナトリウム、ゲラン酸ナトリウム、またはヘキサン酸ナトリウムが含まれる。
好ましくは、経皮送達剤として使用される材料は、Viscolab 3000粘度計(Cambridge Viscosity、Medford、MA)などの標準的な粘度計を使用して測定した場合、室温で約1500cPよりも低い粘度を有する。
置付けられるように選択されてもよい。
本明細書で使用される「化学浸透増強剤」または「CPE」は、一般に、例えば細胞膜の構造(経細胞経路)および/または角質層の細胞間の密接な接合(傍細胞経路)を変化させることによって、皮膚の上皮(角質層)を横断する輸送を補助する化学物質を意味する。
組成物は、薬物を、特定の部位、例えば、角質層、表皮、および/または真皮内に、あるいは皮膚の層の全てを通してかつ超えて、送達するように選択されてもよい。実施例に示されるように、種々のILは、用いられるILに応じて3つの異なる輸送レジームを実証した:1)ドナー溶液中での薬物保持。2)SC、表皮、および真皮内での増強された局在化および保持。3)皮膚の全ての層を通る、およびアクセプター溶液中への、増強された経皮浸透。実施形態の全てにおいて、組成物は皮膚に対して非刺激性であるが、成分の1つまたは複数は、それ自体では刺激性である可能性がある。
経皮的に送達される薬物は、治療効果、診断効果、または予防効果をin vivoでもたらす任意の化学的または生物学的分子であってもよい。薬物含有組成物は、任意の適切な薬物を含有していてもよい。薬物は、処置しまたは予防する疾患または障害に基づいて選択される。薬物は、小分子または高分子、例えばタンパク質またはペプチドであり得る。好ましい実施形態では、薬物は、タンパク質またはペプチドである。しかし、広範な薬物が組成物中に含まれてもよい。本明細書に記述される製剤で使用するのに企図される薬物には、下記のカテゴリーおよび薬物の例、ならびにこれらの薬物の代替形態、例えば代替の塩形態、遊離酸形態、遊離塩基形態、および水和物が含まれるが、これらに限定するものではない:
鎮痛剤/解熱剤(例えば、アスピリン、アセトアミノフェン、イブプロフェン、ナプロキセンナトリウム、ブプレノルフィン、塩酸プロポキシフェン、プロポキシフェンナプシレート、塩酸メペリジン、塩酸ヒドロモルホン、モルヒネ、オキシコドン、コデイン、重酒石酸ジヒドロコデイン、ペンタゾシン、重酒石酸ヒドロコドン、レボルファノール、ジフルニサル、サリチル酸トロラミン、塩酸ナルブフィン、メフェナム酸、ブトルファノール、サリチル酸コリン、ブタルビタール、クエン酸フェニルトロキサミン、クエン酸ジフェンヒドラミン、メトトリメプラジン、塩酸シンナメドリン、およびメプロバメート);
抗喘息薬(例えば、ケトチフェンおよびトラキサノクス);
抗生物質(例えば、ネオマイシン、ストレプトマイシン、クロラムフェニコール、セファロスポリン、アンピシリン、ペニシリン、テトラサイクリン、およびシプロフロキサシン);
抗うつ薬(例えば、ネホパム、オキシペルチン、ドキセピン、アモキサピン、トラゾドン、アミトリプチリン、マプロチリン、フェネルジン、デシプラミン、ノルトリプチリン、トラニルシプロミン、フルオキセチン、ドキセピン、イミプラミン、パモ酸イミプラミン、イソカルボキサジド、トリミプラミン、およびプロトリプチリン);
抗糖尿病薬(例えば、ビグアニドおよびスルホニル尿素誘導体);
抗真菌剤(例えば、グリセオフルビン、ケトコナゾール、イトラコニゾール、アムホテリシンB、ナイスタチン、およびカンジシジン);
降圧剤(例えば、プロプラノロール、プロパフェノン、オキシプレノロール、ニフェジピン、レセルピン、トリメタファン、フェノキシベンザミン、塩酸パルギリン、デセルピジン、ジアゾキシド、モノ硫酸グアネチジン(guanethidine monosulfate)、ミノキシジル、レシナミン、ニトロプルシドナトリウム、rauwolfia serpentina、アルセロキシロン、およびフェントラミン);抗炎症薬(例えば、(非ステロイド系)インドメタシン、ケトプロフェン、フルルビプロフェン、ナプロキセン、イブプロフェン、ラミフェナゾン、ピロキシカム、(ステロイド系)コルチゾン、デキサメタゾン、フルアザコルト、セレコキシブ、ロフェコキシブ、ヒドロコルチゾン、プレドニゾロン、およびプレドニゾン);
抗腫瘍薬(例えば、シクロホスファミド、アクチノマイシン、ブレオマイシン、ダウノルビシン、ドキソルビシン、エピルビシン、マイトマイシン、メトトレキセート、フルオロウラシル、カルボプラチン、カルムスチン(BCNU)、メチル−CCNU、シスプラチン、エトポシド、カンプトテシンおよびその誘導体、フェネステリン、パクリタキセルおよびその誘導体、ドセタキセルおよびその誘導体、ビンブラスチン、ビンクリスチン、タモキシフェン、ならびにピポスルファン);
抗不安剤(例えば、ロラゼパム、ブスピロン、プラゼパム、クロルジアゼポキシド、オキサゼパム、クロラゼプ酸二カリウム、ジアゼパム、パモ酸ヒドロキシジン、塩酸ヒドロキシジン、アルプラゾラム、ドロペリドール、ハラゼパム、クロルメザノン、およびダントロレン);
免疫抑制剤(例えば、シクロスポリン、アザチオプリン、ミゾリビン、およびFK506(タクロリムス));
抗片頭痛剤(例えば、エルゴタミン、プロプラノロール、ムチン酸イソメテプテン(isometheptene mucate)、およびジクロラルフェナゾン);
鎮静薬/催眠薬(例えば、ペントバルビタール、ペントバルビタール、およびセコバルビタールなどのバルビツレート;ならびに塩酸フルラゼパム、トリアゾラム、およびミダゾラムなどのベンゾジアザピン);
抗狭心症剤(例えば、ベータ−アドレナリン作用遮断薬;ニフェジピンおよびジルチアゼムなどのカルシウムチャネル遮断薬;ならびにニトログリセリン、二硝酸イソソルビド、四硝酸ペンタエリスリトール、および四硝酸エリスリチルなどの硝酸薬);
抗精神病剤(例えば、ハロペリドール、コハク酸ロキサピン、塩酸ロキサピン、チオリダジン、塩酸チオリダジン、チオチキセン、フルフェナジン、デカン酸フルフェナジン、エナント酸フルフェナジン、トリフルオペラジン、クロルプロマジン、ペルフェナジン、クエン酸リチウム、およびプロクロルペラジン);
抗躁剤(例えば、炭酸リチウム);
抗不整脈薬(例えば、トシル酸ブレチリウム、エスモロール、ベラパミル、アミオダロン、エンカイニド、ジゴキシン、ジギトキシン、メキシレチン、リン酸ジソピラミド、プロカインアミド、硫酸キニジン、グルコン酸キニジン、ポリガラクツロン酸キニジン、酢酸フレカイニド、トカイニド、およびリドカイン);
抗関節炎剤(例えば、フェニルブタゾン、スリンダク、ペニシラミン、サルサレート、ピロキシカム、アザチオプリン、インドメタシン、メクロフェナメート、金チオリンゴ酸ナトリウム、ケトプロフェン、オーラノフィン、アウロチオグルコース、およびトルメチンナトリウム);
抗痛風剤(例えば、コルヒチンおよびアロプリノール);
抗凝固薬(例えば、ヘパリン、ヘパリンナトリウム、およびワルファリンナトリウム);血栓溶解剤(例えば、ウロキナーゼ、ストレプトキナーゼ、およびアルテプラーゼ);
抗線維素溶解剤(例えば、アミノカプロン酸);
血行動態学的薬剤(hemorheologic agent)(例えば、ペントキシフィリン);
抗血小板剤(例えば、アスピリン);
抗痙攣薬(例えば、バルプロ酸、ジバルプロエクスナトリウム、フェニトイン、フェニトインナトリウム、クロナゼパム、プリミドン、フェノバルビトール、カルバマゼピン、アモバルビタールナトリウム、メトスクシミド、メタルビタール、メホバルビタール、メフェニトイン、フェンスクシミド、パラメタジオン、エトトイン、フェナセミド、セコバルビトールナトリウム、クロラゼペート二カリウム、およびトリメタジオン);
抗パーキンソン剤(例えば、エトスクシミド);
抗ヒスタミン薬/鎮痒薬(例えば、ヒドロキシジン、ジフェンヒドラミン、クロルフェニラミン、マレイン酸ブロムフェニラミン、塩酸シプロヘプタジン、テルフェナジン、フマル酸クレマスチン、トリプロリジン、カルビノキサミン、ジフェニルピラリン、フェニンダミン、アザタジン、トリペレナミン、マレイン酸デキスクロルフェニラミン、メトジラジン、および);
カルシウム調節に有用な薬剤(例えば、カルシトニンおよび副甲状腺ホルモン);
抗細菌剤(例えば、硫酸アミカシン、アズトレオナム、クロラムフェニコール、パルミチン酸クロラムフェニコール、シプロフロキサシン、クリンダマイシン、パルミチン酸クリンダマイシン、リン酸クリンダマイシン、メトロニダゾール、塩酸メトロニダゾール、硫酸ゲンタマイシン、塩酸リンコマイシン、硫酸トブラマイシン、塩酸バンコマイシン、硫酸ポリミキシンB、コリスチメテートナトリウム、および硫酸コリスチン);
抗ウイルス剤(例えば、インターフェロンアルファ、ベータ、またはガンマ、ジドブジン、塩酸アマンタジン、リバビリン、およびアシクロビル);
抗菌薬(例えば、セファゾリンナトリウム、セフラジン、セファクロル、セファピリンナトリウム、セフチゾキシムナトリウム、セフォペラゾンナトリウム、セフォテタン二ナトリウム、セフロキシムeアゾチル(cefuroxime e azotil)、セフォタキシムナトリウ
ム、セファドロキシル一水和物、セファレキシン、セファロチンナトリウム、塩酸セファレキシン一水和物、セファマンドールナフェート、セフォキシチンナトリウム、セフォニシドナトリウム、セフォラニド、セフトリアキソンナトリウム、セフタジジム、セファドロキシル、セフラジン、およびセフロキシムナトリウムなどのセファロスポリン;アンピシリン、アモキシシリン、ペニシリンGベンザチン、シクラシリン、アンピシリンナトリウム、ペニシリンGカリウム、ペニシリンVカリウム、ピペラシリンナトリウム、オキサシリンナトリウム、塩酸バカンピシリン、クロキサシリンナトリウム、チカルシリン二ナトリウム、アズロシリンナトリウム、カルベニシリンインダニルナトリウム、ペニシリンGプロカイン、メチシリンナトリウム、およびナフシリンナトリウムなどのペニシリン;エチルコハク酸エリスロマイシン、エリスロマイシン、エリスロマイシンエストレート、ラクトビオン酸エリスロマイシン、ステアリン酸エリスロマイシン、およびエチルコハク酸エリスロマイシンなどのエリスロマイシン;ならびにテトラサイクリン、例えば塩酸テトラサイクリン、ドキシサイクリンヒクレート、および塩酸ミノサイクリン、アジスロマイシン、クラリスロマイシン);
抗感染症薬(例えば、GM−CSF);
気管支拡張薬(例えば、塩酸エピネフリン、硫酸メタプロテレノール、硫酸テルブタリン、イソエタリン、メシル酸イソエタリン、塩酸イソエタリン、硫酸アルブテロール、アルブテロール、ビトルテロルメシレート、塩酸イソプロテレノール、硫酸テルブタリン、重酒石酸エピネフリン、硫酸メタプロテレノール、エピネフリン、および重酒石酸エピネフリンなどの交感神経作用薬;臭化イプラトロピウムなどの抗コリン作用剤;アミノフィリン、ジフィリン、硫酸メタプロテレノール、およびアミノフィリンなどのキサンチン;クロモリンナトリウムなどの肥満細胞安定化薬;ジプロピオン酸ベクロメタゾン(BDP)およびジプロピオン酸ベクロメタゾン一水和物などの吸入コルチコステロイド;サルブタモール;臭化イプラトロピウム;ブデソニド;ケトチフェン;サルメテロール;キシナホエート;硫酸テルブタリン;トリアムシノロン;テオフィリン;ネドクロミルナトリウム;硫酸メタプロテレノール;アルブテロール;フルニソリド;プロピオン酸フルチカゾン(fluticasone proprionate);
ステロイド系化合物、ホルモン、およびホルモン類似体(例えば、GLP−1およびエキセナチドなどのインクレチンおよびインクレチン模倣体、ダナゾール、シピオン酸テストステロン、フルオキシメステロン、エチルテストステロン、エナント酸テストステロン(testosterone enathate)、メチルテストステロン、フルオキシメステロン、およびシピオン酸テストステロンなどのアンドロゲン;エストラジオール、エストロピペート、および結合型エストロゲンなどのエストロゲン;酢酸メトキシプロゲステロンおよび酢酸ノルエチンドロンなどのプロゲスチン;トリアムシノロン、ベタメタゾン、リン酸ベタメタゾンナトリウム、デキサメタゾン、リン酸デキサメタゾンナトリウム、酢酸デキサメタゾン、プレドニゾン、酢酸メチルプレドニゾロン懸濁液、トリアムシノロンアセトニド、メチルプレドニゾロン、リン酸プレドニゾロンナトリウム、コハク酸メチルプレドニゾロンナトリウム、コハク酸ヒドロコルチゾンナトリウム、トリアムシノロンヘキサアセトニド、ヒドロコルチゾン、シピオン酸ヒドロコルチゾン、プレドニゾロン、酢酸フルドロコルチゾン、酢酸パラメタゾン、テブト酸プレドニゾロン、酢酸プレドニゾロン、リン酸プレドニゾロンナトリウム、およびコハク酸ヒドロコルチゾンナトリウムなどのコルチコステロイド;ならびにレボチロキシンナトリウムなどの甲状腺ホルモン);
血糖降下剤(例えば、ヒトインスリン、精製したウシのインスリン、精製したブタのインスリン、組換え生成したインスリン、インスリン類似体、グリブリド、クロルプロパミド、グリピジド、トルブタミド、およびトラザミド);
脂質低下剤(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、プラバスタチン(pravastitin)、アトルバスタチン、ロバスタチン、およびナイア
シン);
ペプチド;
タンパク質(例えば、DNase、アルギナーゼ、スーパーオキシドジスムターゼ、およびリパーゼ);
核酸(例えば、本明細書に記述されるタンパク質のいずれかを含めた任意の治療上有用なタンパク質をコードするセンスまたはアンチセンス核酸、およびsiRNA);
赤血球新生刺激に有用な薬剤(例えば、エリスロポイエチン);
抗潰瘍/抗逆流剤(例えば、ファモチジン、シメチジン、およびラニチジン塩酸塩);
制吐薬/抗嘔吐薬(例えば、塩酸メクリジン、ナビロン、プロクロルペラジン、ジメンヒドリナート、塩酸プロメタジン、チエチルペラジン、およびスコポラミン);
油溶性ビタミン(例えば、ビタミンA、D、E、およびKなど);
ならびにミトタン、ハロニトロソ尿素、アンスロサイクリン、およびエリプチシンなどの他の薬物。
0版(The Pharmaceutical Press、London 1993年)に見出すことができる。
皮膚への送達に適した任意の剤形を使用してもよい。組成物は、フィルム、デポー、パッチ、またはニートの液体、クリーム、ローションの形態をとってもよい。
本明細書に記述される組成物は、経皮薬物送達に使用されてもよい。
塩化トリヘキシルテトラデシルホスホニウムまたはCYPHOS 101(CY101)は、Cytec Specialty Chemicals(Niagara Falls、Ontario)から寄贈されたものであり、使用する前に、1M重炭酸ナトリウムおよび水で洗浄し、300nmを超えるUV−Vis吸収が消失しかつ2mLの水のpHが2mLのイオン性液体と共に振盪させた際に変化しなくなるまでヘキサンで抽出することによって精製した。次いでCY101を、真空下80℃で24時間乾燥させた。
250mLの体積のn−オクタノールを、100mLのddH2Oと共に振盪させ、一晩放置した。飽和オクタノールを使用して、5mLの容量フラスコ内に各ILの0.01M溶液を調製し、ならびに水に溶かした0.01M溶液も調製した。コリン−オレエートおよびBZBN材料の場合、アッセイを行った濃度はそれぞれ0.0005Mおよび0.0001Mであったが、それは0.01Mでの吸収が検出器にとって高過ぎたからであった。BMP−NTf2 ILを0.2Mでアッセイしたが、それはより低い濃度での吸収が、許容可能な検出限界よりも低いからであった。205から215nmの間の吸収最大値を、全ての場合に観察した。
として報告した。オクタノール中のILのパーセントは、抽出後のオクタノール層の吸光度を抽出前のオクタノール中のILの吸光度で割った商として計算した。水/オクタノールの分布係数は、オクタノール中のILのパーセントの対数を水中のILのパーセントで割った商として計算した。
粘度は、1mLの試料に関し、Viscolab 3000粘度計(Cambridge Viscosity、Medford、MA)で測定した。試料を90℃まで加熱し、粘度を50℃から90℃の間において2℃刻みで(in 2 degree increments)記録
し、各温度で8分間の平衡状態を保った。低温示差走査熱量測定(DSC:differential
scanning calorimetry)は、分当たり10℃のランプ速度(ramp rate)かつアルミ
ニウム坩堝中18〜21mgの試料サイズを用いての、−60℃から120℃の温度範囲にわたる2回の完全走査に関して、N2雰囲気下、DSC882e機器(Mettler−Toledo Inc.、Columbus、Ohio)で行った。
伝導率の決定を、ION450ベンチトップメーター(Radiometer Analytical)で、粘性液体に使用するために設計された2極電極(Radiometer Analytical CDC241−9)により行い、KClで較正した。伝導率は、25℃で、撹拌した3mL体積のニートのILに関し、試料当たり3回測定した。密度は、1mLの容量フラスコおよび分析天秤を使用して、IL当たり3回測定した。
吸収スペクトルを、Hewlett−Packard 8453ダイオードアレイ分光光度計(Agilent Technologies,Inc.、Santa Clara、CA)で、1cmの光路長(pathlength)の石英キュベットで収集した。NMRデータ集合を、300MHz Bruker機器で、CDCl3中50mMの試料濃度を使用して収集した。
PR4−オレエートの調製。[P(C14H29)(C6H13)3]+カチオンおよびオレエートアニオンを含有するイオン性液体を、塩メタセシスを介して調製した。オレイン酸ナトリウム(10.0g、0.035mol)をクロロホルムに溶かした溶液50mLに、塩化トリヘキシルテトラデシルホスホニウム(CY101、18.39g、0.35mol)をクロロホルムに溶かした溶液50mLを添加した。50mLの水を5回に分けて撹拌溶液に添加し、そして除去した。その後、除去した水の硝酸銀による試験は、クロリドの存在に関してもはや陽性ではなかった。溶媒をクロロホルム層から取り除き、得られたILを、真空オーブン内で、80℃で48時間乾燥させた。
を2時間撹拌した。CY101層を、ddH2Oで3回洗浄し、回転蒸発により乾燥させ、かつ真空オーブン内で、65℃で48時間乾燥させた。
コリン−NTf2の調製。コリン−NTf2の合成は、Nockemannら[1]によって記
載されたように行い、密度(1.5g/mL)、NMR(1Hおよび13C)、および融点(30℃)は、公表された値に一致することがわかった。25℃での物理特性:水への溶解度=1.7M;密度=1.53g/mL;伝導率=1.46mS/cm;粘度=125cP。
3巻(20号):4164〜4170頁(1999年)に記載されているように行い、Baker, S.N.ら、「Fluorescence studies of protein thermostability in ionic liquids」、Chemical Communications、(8巻):940〜1頁(2004年)に記載
されるように改変した。
Ionic Liquids」、Crystal Growth & Design、12巻(11号):5357〜5364頁(2012年)に記載されるように、塩化ベンゼトニウムと2当量の無水塩化亜鉛との混合物から行い、その後、BMP−NTf2と合わせた。
63〜1264頁(1982年)に記載されるように、1−メチルイミダゾール(11.9g、0.122mol)を過剰なクロロヘキサン(20.98g、0.146mol)とともに3時間還流するか、または数滴の反応混合物をCu(SO4)の水溶液に添加すると青色が消えることによる試験のとおり反応が終了するまで還流した。Carson, L.ら
、「Antibiofilm activities of 1-alkyl-3-methylimidazolium chloride ionic liquids」、Green Chemistry、11巻(4号):492〜497頁(2009年)。クロロヘキサンを、回転蒸発によって除去した。
コリン/カルボン酸比の決定。3、2、1、0.5、または0.33当量の重炭酸コリン(80重量%溶液)に、ニートのヘキサン酸(2g、0.007mol)を、20mLのシンチレーションバイアル内に添加した。混合物を、CO2の発生が消えるまで室温で撹拌した。溶媒を60℃で20分間の回転蒸発によって除去し、各生成物を、真空オーブン内で60℃で48時間乾燥させた。融点を、記述されるようにDSCにより決定し、好ましい組成を、最低融点を有するものになるように決定した。
尿素−コリンの調製。Abbott, A.P.ら、「Novel solvent properties of choline
chloride/urea mixtures」、Chem. Commun.(Cambridge、U.K.)、(1巻):70〜71頁 2003年)に記載されるように、尿素(10g、0.167mol)2当量を、塩化コリン(11.6g、0.083mol)1当量と、シンチレーションバイアル内で、アルゴン雰囲気下で混合した。材料を、60℃の真空オーブン内で24時間乾燥させた。DESを、使用前に30℃に加熱した。
細胞の培養および曝露。正常ヒト気管支上皮(NHBE:normal human bronchial epithelial)細胞を購入し(Lonza、Walkersville、MD)、気管支上皮細胞成長培地(BEGM、Clonetics Bullet Kit、Lonza、Walkersville、MD)を使用して、50μg/mLのI型ラット尾部コラーゲン(BD Biosciences、Bedford、MA)がコーティングされた100mmの組織培養処理Petri皿(Santa Cruz Biotechnologies、Santa Cruz、CA)上に培養した。細胞を、37℃および5%CO2の加湿雰囲気を持つインキュベーター内に保存した。細胞には週に2回栄養を与え、トリプシン処理を介して継代した。実験は、3から7回の継代から収集した細胞に関して3連で行った。
8〜67頁(2009年)に概説されるように、LDH細胞毒性キット(Clontech、Mountain View、CA)を使用して、LDH活性を測定することによって評価した。
3H標識したマンニトールおよびセファドロキシルを、American Radiolabeled Chemicals,Inc.およびMoravekからそれぞれ得た。FDCは、既に確立されたプロトコールを使用してイオン性液体の輸送増強を評価するのに使用した。Karandeら、「Discovery of transdermal penetration enhancers by high-throughput screening」、Nat Biotechnol、22巻(2号):192〜7頁(2004年)。簡単に言うと、アクセプターチャンバーを脱気したPBSで満たし、小さい撹拌棒を加えた。解凍したブタの皮膚を、SCを上に向けた状態で、アクセプターチャンバーおよびドナーチャンバーの間の所定位置にクランプ留めした。気泡がアクセプターチャンバー内に確実に存在しなくなるように、注意を払った。イオン性液体またはPBS(対照)に、3H標識した薬物(マンニトールおよびセファドロキシル)をスパイクして、最終濃度10μCi/mlにした。ドナー溶液300μLをドナーチャンバーに加え、SCに接触させて、撹拌しながら37℃で24時間インキュベートした。
*すすぎ、チャレンジ、洗浄、および超音波処理に使用される96ウェルプレートは、蓋付きCostar平底ポリスチレンCat#3370であった。96ウェルプレート
pm:新鮮なLB寒天プレートを画線するのに、グリセロールストックアリコートを使用する。単離したコロニーに関して画線する。37℃で一晩インキュベートする。
am:インキュベーションから成長寒天プレートを除去し、汚染を検査する。寒天プレートを、その日の遅くまで室温または4℃で保存する。
pm:成長プレートからの単一コロニーを使用して、5mL LB液体培養物に接種する。激しく振盪しながら(225〜250rpm)37℃で一晩インキュベートする。
am:新鮮な5mLのLB液体培養物に、一晩の液体培養物(1:100希釈)からの50uLを接種する。培養物が対数期増殖(約0.5OD)に到達するまで、激しく振盪しながら37℃でインキュベートする。これはほとんどの実験室細菌株に関して、およそ3時間である。
、縁部をパラフィルムで封止する。これは、ウェルからの蒸発を防止するのに最良の方法である。プレートを、225RPM、37℃で24時間インキュベートする。
24時間のバイオフィルム成長で、MBECペグ蓋(peg lid)を、新鮮なLB培地が200uL/ウェル入っている新鮮な96ウェルプレート上に配置することにより、バイオフィルムからプランクトン細胞/培地を除去する。プランクトン細胞/培地を含有するウェルプレートを廃棄する。
ステップI:MBECペグ上で成長させたバイオフィルムを室温で短時間すすいで、プランクトン細胞および緩く接着した細菌性細胞を除去した。MBECペグ蓋を、200uL/ウェルのLBが入っている96ウェルプレート上に短時間配置した。プランクトン細胞を、バイオフィルム成長プレートおよびすすぎプレート(MBECペグ蓋ではない)の両方から、10%ブリーチが入っている除染バケットへと廃棄した。
ステップIV:イオン性液体チャレンジの後、室温でバイオフィルムを200uL/ウェル LBで短時間洗浄し、次いで希釈のために確保した。
ステップX:全ての試料を希釈した後、希釈物を大型LB寒天プレート上に配置した(プレートは室温であった)。濃厚(A)を使用して、1行の10−2希釈物(C)、10−4希釈物(E)、および10−6希釈物(G)を、ピペッター(ピペットチップを1つおきにつけた8チャネルピペッター)を使用して3〜5回混合し;次いで15uLスポットを大型寒天プレートに移した。これを10−1希釈物(B)、10−3希釈物(D)、10−5希釈物(F)、および10−7希釈物(H)に関して繰り返した。
ステップXII:寒天プレートをインキュベーションから取り除いた。各試料希釈セットについて、20〜200のコロニーを含有するスポットでコロニーをカウントした。コロニーの数および希釈係数を記録した。
a.チャレンジ試料:(コロニーの数)×(希釈係数)/0.015mL×2
b.洗浄/超音波処理試料:(コロニーの数)×(希釈係数)/0.015mL
ステップXVI:チャレンジアッセイを、バイオフィルム成長から開始して繰り返した。2重成長/チャレンジアッセイに関する平均cfu/mLおよびstdev.pを計算
し、次いで2重成長/チャレンジアッセイから得られた6つの試料全てに関する平均cfu/mLおよびstdev.pを計算した。
親油性
表3は、様々なILの親油性データ(date)を、オクタノール/水分配係数に関して示す。
Halide Species Ambiguity to Develop Amorphous, Stabilized Pharmaceutical Agents As Ionic Liquids」、Crystal Growth & Design、12巻(11号):
5357〜5364頁(2012年)。BMP−NTfのlogPo/W(−0.4)とBZBNのそれ(1.34)との間の大きな相違の理由は、BMP−NTf2が、水およびオクタノールと接触すると第3の相を形成したからである。オクタノール中の開始濃度0.2Mでは、水相中のBMP−NTf2のパーセンテージは51%であり、オクタノールまたは水に取り込まれていないパーセンテージは29%であった。親油性は、他の重要な性質、特に、実際には水酸化コリンからの1:1であるコリン−ナフテン系(choline-naphthenic)「IL」を参照することができる。Yu, Y.ら、「Biodegradable naphthenic acid ionic liquids: synthesis, characterization, and quantitative structure-biodegradation relationship」、Chem.--Eur. J.、14巻(35号):11174〜11182頁(2008年)。
表4は、24時間後のWST結果を示す。下限が与えられた場合、材料の溶解度は適正なIC50値を排除した。
初代ヒト細胞における材料の毒性を、正常ヒト気管支上皮(NHBE)細胞で試験した。この研究は、ニートのIL/DESではなくILおよびDES希釈で行ったが、それは血流に吸収された際の毒性をモデル化することが意図されたからであった。全ての材料を、2.0、0.8、0.3、0.1、0.05、0.02、および0.008mMの濃度で試験した。培養培地中でのそれらの高い溶解度により、HMIM−Clおよびコリン−ヘキサノエートは、それぞれ最大500mMおよび30mMの濃度でも試験をした。最も毒性のある材料は、オレイン酸コリン(IC50=0.034mM)およびBZBN(IC50=0.013mM)であり、毒性が最小の材料は尿素−コリン(IC50>10mM)およびHMIM−Cl(IC50=10mM)であった。
トで使用した場合に有効であり、培養培地中のヒト初代細胞に対しては低毒性を有する。これは、IL溶解が急速に生じる大きい開放創の処置に重要と考えられる。あるいは、溶解後の細胞に対して毒性のあるILは、局所的にまたはILの溶解がより遅い状況で、使用されてもよい。オレイン酸コリンおよびBZBNを含めた溶液中の初代ヒト細胞に対して非常に毒性のあるイオン性液体は、オクタノールにも十分に分配され、その傾向は毒物学の文献にも記載されている。
様々なILに関する粘度、伝導率、ならびに容量モル濃度およびイオン強度の計算を表5に示す。
表2に列挙されたイオン性液体(IL)のパネルの輸送増強を、試験した。ILパネルを、3H−マンニトールを使用して最初にスクリーニングした。結果を図2Aに示す。
pseudomonasおよびsalmonellaに対するILの効力を試験した。試験した全てのILは、抗バイオフィルム活性を示したが、その程度は様々であった。72時間のフィルムは、IL(IL2以外)および対照による破壊/死滅化に対してより高い耐性があった。図4および5。いくつかのILは、10%ブリーチよりもバイオフィルムに対して有効である。図4B。種に特異的な弁別的IL効力が存在し得る。これは、Pseudomonas対Salmonellaのプロットに見ることができる。図4Cを参照されたい。データは、イオン性液体が、細菌性バイオフィルムEPSを破壊し病原性細菌を死滅させる潜在性を有することを示唆している。図4および5を参照されたい。
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