JP2009532564A - 生分解性のカチオン性ポリマー - Google Patents
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Abstract
【選択図】 図1
Description
本出願は、2006年4月6日に出願された米国仮特許出願第60/789,842号に基づく優先権を主張し、それは引用によりその全文が全ての図面を含めて本明細書に取り込まれる。さらに、本出願は、2005年8月31日に出願された米国特許出願第11/216,986号に関し、それは引用によりその全文が全ての図面を含めて本明細書に取り込まれる。
本発明は、生理活性薬剤を細胞に送達するための組成物と方法に関する。具体的には、本発明は、ポリ−またはオリゴ−エチレンイミン(PEI)、生分解性基、および比較的疎水性の基を含むカチオン性リポポリマーに関し、またsiRNAおよびアンチセンスなどのオリゴヌクレオチドを送達するためにそのようなリポポリマーを製造し、使用する方法に関する。
ウイルストランスフェクションシステムや非ウイルストランスフェクションシステムの使用を含む多くの技術が、プラスミドDNAなどの生理活性薬剤を細胞に送達するために利用可能である。ウイルスシステムは、概して非ウイルスシステムよりも高いトランスフェクション効率を有するが、ウイルスシステムの安全性に関して疑問があった。Verma I.M および Somia N.,Nature 389(1997),pp.239−242;Marhsall E.Science 286(2000),pp.2244−2245を参照されたい。さらに、ウイルスベクターの調製は、複雑で費用のかかるプロセスになりやすい。非ウイルストランスフェクションシステムは、一般的にウイルスシステムよりも効率が劣るが、それらのシステムは一般的にウイルスシステムよりも安全で、調製しやすいと考えられるので、かなりの注目を集めてきた。
本発明者らは、オリゴヌクレオチドを細胞に送達することのできる幾つかのポリマー組成物を見出した。ある実施形態では、ポリマーは、送達増強剤および/または画像診断用化合物などの他の部分にさらに複合体化することができる。さらに、本発明者らは、ポリマー組成物を使用して、オリゴヌクレオチドを細胞に送達するための方法を見出した。
1実施形態は、ポリエチレンイミン、生分解性基、および比較的疎水性の「リポ」基を含むカチオン性リポポリマーを提供する。好ましいカチオン性リポポリマーは、式(I):
スキームA
カチオン性リポポリマーの合成は、スキームAに従って、分子量232ダルトンを有するペンタエチレンヘキサミン(PEHA)を化合物3と以下のように反応させることにより実施した。PEHA(Sigma−Aldrich)約0.1mmol(23mg)と化合物3約0.2mmol(93mg)を量り、小さいバイアルに入れ、エタノール1mLを加えて、素早く溶解した。反応混合物を室温で3時間攪拌した。次いで、反応混合物をエーテル中2MのHCl(5mL)を加えて中和した。白色の沈殿物YT−10を遠心分離して集め、エーテルで2回洗浄し、室温で減圧乾燥した。
EGFP安定細胞株:HT−1080−EGFPとHeLa−EGFP安定細胞株は、強化緑色蛍光タンパク質(EGFP)遺伝子発現を有するそれぞれHT−1080とHeLa細胞に由来し、それらはpEGFP−N1プラスミドDNA(BD Biosciences Clontech)をHT−1080とHeLa細胞にトランスフェクションさせることによって調製された。トランスフェクションされた細胞は、ネオマイシン耐性能力を用いて選択、クローン化され、pEGFP−N1プラスミド上に担持された。細胞培養は、37℃、5%CO2下で、10%ウシ血清、100単位/mlペニシリンと100μg/mlストレプトマイシンを含むダルベッコ改変イーグル培地(DMEM)で維持された。EGFP発現は、蛍光顕微鏡(Olympus)の下で観察することができる。HT−1080−EGFPとHeLa−EGFP細胞の両方は、青色励起光と緑色発光フィルタ設定の組合せによって、明るい緑の蛍光を示した。
siRNA送達研究:EGFP遺伝子を標的とするsiRNAは、Dharmacon Research Inc.によって合成された。EGFP遺伝子を標的とするsiRNAとルシフェラーゼ遺伝子は、21bpの二本鎖RNAであり、それらのセンス鎖の配列は、NNC GAG AAG CGC GAU CAC AUG(配列番号:2)であった。
Claims (23)
- 式(I):
PEIは、600ダルトン未満の分子量を有するポリエチレンイミン繰り返し単位であり;
Rは、電子対、水素、C2−C10アルキル、C2−C10ヘテロアルキル、C5−C30アリール、およびC2−C30ヘテロアリールから成る群から選択され;
Lは、C2−C50アルキル、C2−C50ヘテロアルキル、C2−C50アルケニル、C2−C50ヘテロアルケニル、C5−C50アリール、C2−C50ヘテロアリール、C2−C50アルキニル、C2−C50ヘテロアルキニル、C2−C50カルボキシアルケニルおよびC2−C50カルボキシヘテロアルケニルから成る群から選択され、;ならびに
mは、約1〜約30の範囲にある整数である)から成る群から選択される繰り返し単位を含むポリマー。 - 生分解性である、請求項1〜2のいずれか1項に記載のポリマー。
- 加水分解、酵素切断、還元、光切断、および超音波処理からなる群から選択される機構により分解性である、請求項1〜3のいずれか1項に記載のポリマー。
- Lが、C2−C50アルキル、C2−C50ヘテロアルキル、C2−C50アルケニル、C2−C50ヘテロアルケニル、C2−C50アルキニルおよびC2−C50ヘテロアルキニルから成る群から選択される、請求項1〜4のいずれか1項に記載のポリマー。
- Lが、C12〜C18の脂肪酸、コレステロールおよびそれらの誘導体から成る群から選択される、請求項1〜4のいずれか1項に記載のポリマー。
- 約500ダルトン〜約1,000,000ダルトンの範囲にある重量平均分子量を有する、請求項1〜6のいずれか1項に記載のポリマー。
- 約1,000ダルトン〜約200,000ダルトンの範囲にある重量平均分子量を有する、請求項1〜6のいずれか1項に記載のポリマー。
- 架橋されている、請求項1〜8のいずれか1項に記載のポリマー。
- ポリマーに複合体化されているオリゴヌクレオチドをさらに含む、請求項1〜9のいずれか1項に記載のポリマー。
- オリゴヌクレオチドが、RNA−オリゴマーおよびDNA−オリゴマーから成る群から選択される、請求項10に記載のポリマー。
- オリゴヌクレオチドが、siRNAまたはアンチセンスである、請求項10に記載のポリマー。
- 真核細胞に入ることのできる送達増強剤をさらに含む、請求項1〜12のいずれか1項に記載のポリマー。
- ポリマーに複合体化された画像診断用化合物をさらに含む、請求項1〜13のいずれか1項に記載のポリマー。
- 送達増強剤が、受容体認識、細胞内移行、細胞エンドソームからのオリゴヌクレオチドの脱出、核局在化、オリゴヌクレオチドの放出、およびシステムの安定化からなる群から選択される真核細胞における1つ以上の機能を促進する、請求項13〜14のいずれか1項に記載のポリマー。
- オリゴヌクレオチドが、siRNAおよびアンチセンスから成る群から選択される、請求項15に記載のポリマー。
- 送達増強剤がポリマーに結合されている、請求項13〜16のいずれか1項に記載のポリマー。
- 式(I):
PEIは、式(IIb):
Rは、電子対、水素、C2−C10アルキル、C2−C10ヘテロアルキル、C5−C30アリール、およびC2−C30ヘテロアリールから成る群から選択され;
Lは、C2−C50アルキル、C2−C50ヘテロアルキル、C2−C50アルケニル、C2−C50ヘテロアルケニル、C5−C50アリール、C2−C50ヘテロアリール、C2−C50アルキニル、C2−C50ヘテロアルキニル、C2−C50カルボキシアルケニルおよびC2−C50カルボキシヘテロアルケニルから成る群から選択され;ならびに
mは、約1〜約30の範囲にある整数である]から成る群から選択される繰り返し単位を含むポリマー。 - PEIが、600ダルトン未満の分子量を有する、請求項18に記載のポリマー。
- PEIが、600ダルトン未満の分子量を有する、請求項20に記載のポリマー。
- 細胞を請求項10〜17のいずれか1項に記載のポリマーと接触させ、それによりオリゴヌクレオチドを細胞に送達することからなる真核細胞の形質移入方法。
- R、L、PEI、およびmからなる群から選択される少なくとも1つのパラメータが、ポリマーの少なくとも2つに対して異なる請求項1〜21のいずれか1項に記載の複数のポリマーを含むポリマーライブラリー。
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US78984206P | 2006-04-06 | 2006-04-06 | |
PCT/US2007/008106 WO2007120479A1 (en) | 2006-04-06 | 2007-04-03 | Biodegradable cationic polymers |
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EP (1) | EP2007432B1 (ja) |
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KR (1) | KR20080108153A (ja) |
CN (1) | CN101415444A (ja) |
AU (1) | AU2007238965B2 (ja) |
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CA (1) | CA2648386A1 (ja) |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011514423A (ja) * | 2008-03-14 | 2011-05-06 | エーゲン、インコーポレイテッド | 生分解性架橋分枝状ポリ(アルキレンイミン) |
JP2016531591A (ja) * | 2013-09-18 | 2016-10-13 | オーラ バイオサイエンシーズ, インコーポレイテッド | 腫瘍を診断および処置するためのウイルス様粒子結合体 |
US10300150B2 (en) | 2012-02-07 | 2019-05-28 | Aura Biosciences, Inc. | Virion-derived nanospheres for selective delivery of therapeutic and diagnostic agents to cancer cells |
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CN101415444A (zh) | 2009-04-22 |
EP2007432A1 (en) | 2008-12-31 |
US7700541B2 (en) | 2010-04-20 |
HK1128080A1 (en) | 2009-10-16 |
RU2008142416A (ru) | 2010-05-20 |
KR20080108153A (ko) | 2008-12-11 |
DK2007432T3 (da) | 2012-12-03 |
EP2007432B1 (en) | 2012-09-19 |
AU2007238965A1 (en) | 2007-10-25 |
CA2648386A1 (en) | 2007-10-25 |
BRPI0710648A2 (pt) | 2011-08-23 |
WO2007120479A1 (en) | 2007-10-25 |
US20070243157A1 (en) | 2007-10-18 |
MX2008012692A (es) | 2008-10-10 |
AU2007238965B2 (en) | 2012-03-29 |
RU2451525C2 (ru) | 2012-05-27 |
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