JP2008120718A - 薬物担体 - Google Patents
薬物担体 Download PDFInfo
- Publication number
- JP2008120718A JP2008120718A JP2006305410A JP2006305410A JP2008120718A JP 2008120718 A JP2008120718 A JP 2008120718A JP 2006305410 A JP2006305410 A JP 2006305410A JP 2006305410 A JP2006305410 A JP 2006305410A JP 2008120718 A JP2008120718 A JP 2008120718A
- Authority
- JP
- Japan
- Prior art keywords
- drug carrier
- drug
- inhibitors
- formula
- polyglycidol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical group OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims abstract description 9
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Abstract
【解決手段】(A)特定構造のアミジン誘導体および/またはその塩と、(B)3−メチルグルタリル変性グリシドール単位を含むポリグリシドールと、で修飾された脂質膜の担体粒子に、薬物を担持した薬物担体。
【選択図】なし
Description
したがって本発明は、腎ガン、肺ガン、肝ガン、膵ガンなどの癌、リンパ腫、肺炎、肝炎、腎炎、血管内皮損傷部位などの病巣部位を確実にターゲッティングし、病患部もしくは標的細胞内に治療および/または診察するための薬物を安全にかつ効率良く送達することができ、特に、核酸、ポリヌクレオチド、遺伝子およびその類縁体などの細胞内で薬理作用を示す生理活性物質の細胞へのトランスフェクションを、安全にかつ効率良く行うことができるDDSの達成に有効な薬物担体を提供することを目的としている。
(1)(A)後述する一般式1で示されるアミジン誘導体および/またはその塩と、(B)後述する式2および3で示される3−メチルグルタリル変性グリシドール単位を含むポリグリシドールと、で修飾された脂質膜の担体粒子に、薬物を担持した薬物担体。
このため、薬学的に許容し得る薬理的活性物質、生理的活性物質または診断用物質を封入した本発明の薬物担体は、治療および診断目的のDDS、特に遺伝子DDSとして有効的である。
脂質は、膜形成能を有するものであれば、リン脂質であってもリン脂質以外の脂質であってもよく、それらの誘導体、さらにはそれらの組み合わせであってもよい。リン脂質としては、ホスファチジルコリン(=レシチン)、ホスファジルグリセロール、ホスファチジン酸、ホスファチジルコリン、ホスファチジルエタノールアミン、ホスファチジルセリン、ホスファチジルイノシトール、スフィンゴミエリン、カルジオリピン等の天然あるいは合成のリン脂質、またはこれらの部分または完全水素添加物など、およびこれらの組み合わせを挙げることができる。他の脂質としては、脂肪酸などが挙げられる。
式1中、Aは芳香環である。
R1およびR2は互いに独立に炭素数10〜25、好ましくは1〜18のアルキル基またはアルケニル基である。
X1およびX2は互いに独立にO、S、COO、OCO、CONHまたはNHCOである。
mは0または1、nは0または1〜6の自然数である。
アミジン誘導体の塩は、塩酸塩、スルホン酸塩などの形態が挙げられる。以下、アミジン誘導体の語は塩の形態も含めた意味で使用されることがある。
上記式中、R1およびR2は、同一または異なっていてもよい炭素数10〜18のアルキル基であり、好ましくはR1およびR2が同一である。
ポリグリシドール(B)が両方の作用効果を充分に発揮するには、各単位を1分子とみなす組成として、ポリグリシドール(B)の総量100モル%に対し、式2で示されるカルボン酸単位は60モル%以上、式3の単位は5モル%以上で存在することが望ましい。一方、複合化作用を発揮するには、式2の単位は95モル%以下であることが望ましく、また弱酸性下で生体膜との相互作用を発揮するには、式3で示される長鎖アルキル基含有単位は40モル%以下であることが望ましい。したがって本発明におけるポリグリシドール(B)は、ポリグリシドール(B)の総量を100モル%とするとき、上記式2で示されるカルボン酸単位を60〜95モル%、好ましくは80〜90モル%、上記式3で示される長鎖アルキル基含有単位を5〜40モル%、好ましくは5〜10モル%含有する。
後者の方法は本発明の好ましい態様例であり、たとえばBiochim Biophys Acta 1994;1193:1-9に記載された方法に準拠して調製することができる。具体的には、PGと、3−メチルグルタル酸無水物とを反応させることにより、式2で示される単位を生成させる。この反応は、N,N-ジメチルホルムアミドなどの溶媒中で行うことができる。
次に、該当するアミンR3NH2と反応させ、式3で示される単位を生成させる。
各段階での変性量は、3−メチルグルタル酸無水物またはアミンの使用量によって調整することができる。式2で示される3-MGluG単位の導入量は、pHメーターを用いる電位差滴定により決定することができる。
上記J. Polym. Sci.およびBiochim Biophys Actaの各記載は、これを引用することにより本明細書中にも記載されているものとするが、本発明におけるポリグリシドール(B)の製造方法は、これら方法に限定されるものではない。
酸化防止剤としては、トコフェロール同族体すなわちビタミンEなどが挙げられる。コトフェロールには、α、β、γ、δの4個の異性体が存在するが本発明においてはいずれも使用できる。
本発明の薬物担体が、薬物として特に遺伝子を担持する場合には、膜構成成分にトランスフェリンを結合させ、薬物担体をトランスフェリンレセプターとの特異的な結合を介して細胞に取り込ませれば、優れた遺伝子導入活性を発現することができる。
治療のための薬剤の種類としては、薬物担体の形成および安定性を損ねない限り特に制限されないが、核酸、ポリヌクレオチド、遺伝子およびその類縁体、グリコサミノグリカンおよびその誘導体、オリゴ糖、多糖およびそれらの誘導体、タンパク質およびペプチドなどの生理活性的物質;抗癌剤、抗生物質、酵素剤、抗酸化剤、脂質取り組み阻害剤、ホルモン剤、抗炎症剤、ステロイド剤、血管拡張剤、アンジオテンシン受容体拮抗剤、アンジオテンシン変換酵素阻害剤、平滑筋細胞の増殖・遊走阻害剤、血小板凝集阻害剤、抗凝固剤、ケミカルメディエーターの遊離抑制剤、血管内皮細胞の増殖または抑制剤、アルドース還元酵素阻害剤、メサンギウム細胞増殖阻害剤、リポキシゲナーゼ阻害剤、免疫抑制剤、免疫賦活剤、抗ウィルス剤、メイラード反応抑制剤、アミロイドーシス阻害剤、NOS阻害剤、AGEs(Advanced glycation endproducts)阻害剤およびラジカルスカベンジャーの薬理的活性物質などが挙げられる。
抗炎症剤の例としては、サリチル酸コリン、サザピリン、サリチル酸ナトリウム、アスピリン、ジフルニサル、フルフェナム酸、メフェナム酸、フロクタフェニン、トルフェナム酸、ジクロフェナクナトリム、トルメチンナトリウム、スリンダク、フェンブフェン、フェルビナクエチル、インドメタシン、インドメタシンファルネシル、アセメタシン、マレイン酸プログルメタシン、アンフェナクナトリウム、ナブメトン、イブプロフェン、フルルビプロフェン、フルルビプロフェンアキセチル、ケトプロフェン、ナプロキセン、プロチジン酸、プラノプロフェン、フェノプロフェンカルシウム、チアプロフェン酸、オキサプロジン、ロキソプロフェンナトリウム、アルミノプロフェン、ザルトプロフェン、フェニルブタゾン、クロフェゾン、ケトフェニルブタゾン、ピロキシカム、テノキシカム、アンピロキシカム、塩酸チアラミド、塩酸チノリジン、塩酸ベンジダミン、エピリゾール、エルモファゾンなどが挙げられる。
抗ウイルス剤の例としては、アシクロビル、ガンシクロビル、ジダノシン、ジドブジン、ソリブジン、ビダラビンなどが挙げられる。
上記カチオン性リポソームに遺伝子を内包した態様はリポプレックスと称される。この3-MGluPG修飾リポソーム・カチオン性リポプレックス複合体は、本発明の薬物担体の好ましい態様例として例示される。
この場合、3-MGluPGのカルボン酸単位に由来して負電荷(−)を帯びたリポソームと、正電荷(+)を帯びたリポプレックスとが双方の構造を保ったまま穏やかに電荷で結合するような比で複合体が形成され、かつ病巣部位を確実にターゲッティングし、細胞内への高い薬物導入率を発現することができるような電荷比で、アミジンカチオン性リポプレックスと3-MGluPG修飾リポソームとの複合体を構成することが望ましい。この際、アミジン誘導体と3-MGluPGとの複合比は、複合体成分のリポプレックスそのものの電荷比によっても異なり一概にはいえないが、DNAを基準にアミジンカチオン性リポプレックスおよび3-MGluPG修飾リポソームの電荷比を設定することができる。
まず、フラスコ内に、リン脂質等の担体膜構成材料を、クロロホルム等の有機溶媒により混合し、有機溶媒を留去後真空乾燥することによりフラスコ内壁に薄膜を形成させる。次にポリグリシドール(B)のメタノール溶液を加え、有機溶媒を留去後、真空乾燥させることによりフラスコ内壁に脂質−ポリグリシドール(B)混合薄膜を形成させる。当該フラスコ内に、PBSを加え、激しく撹拌することにより、3-MGluPG修飾リポソームを形成する。
3-MGluPG修飾リポソームは、上記方法以外にも上記の各構成成分を混合し、高圧吐出型入乳化機により高圧吐出させる方法によっても得ることができる。
薬物封入カチオン性リポソームは、上記方法以外にも、上記各構成成分を混合し、高圧吐出型入乳化機により高圧吐出させることにより得ることもできる。
上記において、カチオン性リポソームに遺伝子を担持させた場合にはリポプレックスが形成される。
本発明で調製されるリポプレックスは、3-MGluPG修飾リポソームとの複合後も安定に小粒径を保持することができる。
以下の実施例において、粒子径および表面電位は、粒度分布・ゼータ電位測定装置(Particle Sizing Systems 社製 型式NICOMP 380ZSL)にて測定した。
ポリグリシドールの分子量は高速液体クロマトグラフィー(Asahipak GS-510 カラム)で測定した。
pHメーターは、堀場製作所社製M−8を用いた。
ポリグリシドール(分子量8700)1.44gと、3−メチルグルタル酸無水物(ALDRICH社,Mw=128)7.6gとを、予め精製したN,N-ジメチルホルムアミド中、130℃で6時間反応させ、3−メチルグルタル酸基を導入した(収量2.6g)。
次に、上記3−メチルグルタル酸変性ポリグリシドール500mgを、約20mLの水に溶解した後、EDC(1-Ethyl-3-(3dimethylaminopropyl)carbodiimide)(Dojindo Mw=191.7)67.8mgを加え、氷冷下にて撹拌した後、n-デシルアミン(東京化成 Mw=157.3)39.8mgを加えた。HClを用いて反応溶液のpHをおよそ6に調整し、3日間氷冷中にて反応させ、式3で示される長鎖アルキル(n-デシル)基を導入し、510mgの3-MGluPGを得た。
得られた3-MGluPGについて、式2で示されるカルボン酸単位量はpHメーターを用いて分析し、式3で示される長鎖アルキル基含有単位量は1H-NMRで分析した。残余を未変性ポリグリシドールとして結果を表1に示す。
分子量8200のポリグリシドールを用い、酸無水物を無水コハク酸または無水グルタル酸に代えた以外は、調製例1と同様の操作を行い、下記式5および6で示される単位を含むスクシニル変性ポリグリシドール(SucpG)、式7および8で示される単位を含むグルタリル変性ポリグリシドール(GluPG)を得た。これらの組成を表1に示す。
表中、組成数値は、各単位を1分子とみなしたときのモル%である。
未変性単位は、式2で示されるグリシドール単位である。
3-MGluPGにおいて、カルボン酸単位は式2で示される単位、長鎖アルキル基含有単位は式3で示される単位である。
SucpGにおいて、カルボン酸単位は下記式5で示される単位、長鎖アルキル基含有単位は下記式6で示される単位である。
GluPGにおいて、カルボン酸単位は下記式7で示される単位、長鎖アルキル基含有単位は下記式8で示される単位である。
下記1)〜3)の工程により、薬物担体として、3-MGluPG修飾リポソーム・カチオン性リポプレックス複合体を調製した。
1)3-MGluPG修飾リポソームの調製
卵黄ホスファチジルコリン(EYPC)(10mg/mL)のクロロホルム溶液700μLをナス型フラスコに装入し、クロロホルムをロータリーエバポレーターで減圧留去してEYPCの薄膜を形成させた。
これに調製例1で得られた3-MGluPGのメタノール溶液(3mg/mL)を1mL加え、再び溶媒を減圧留去し、脂質−3-MGluPG混合薄膜を形成させた。これを約2時間真空乾燥した後、PBSを2mL加え、バス型超音波照射装置を用いて30秒間超音波照射して脂質−3-MGluPG混合膜を分散させた。この分散液のpHを7に調整した後、凍結−融解を3回行って、3-MGluPG修飾リポソーム(懸濁液)を形成した。さらに、エクストルーダーを用いて孔径50nmのポリカーボネート膜を通して、リポソームの粒子径を揃えた。
その後、3-MGluPG修飾リポソームのpHを7.4に調整し、セファデックスG75カラムを用いて遊離トランスフェリンを除去し、さらに、ろ過滅菌して、3-MGluPG修飾リポソームにトランスフェリンを結合させた。
<カチオン性リポソームの調製>
3,5-ジペンタデシロキシベンズアミジン塩酸塩(157μg)、DLPC(ジラウロイルホスファチジルコリン)(165μg)および中性脂質DOPE(ジオレオイルホスファチジルエタノールアミン)(384μg)をクロロホルム(0.25mL)に溶解し、ロータリーエバポレーターを用いて溶媒を留去して混合脂質の薄膜を形成させた。これにPBS(2mL)を加え、バス型超音波照射装置で2分間分散させてカチオン性リポソームを得た。
プラスミドDNA(1μg)を20mM Tris−HCl溶液(50μL)に溶解した溶液と、該溶液のDNA(−)に対する3,5-ジペンタデシロキシベンズアミジン塩酸塩(+)の電荷比(+/−)が6になるように量を調整した上記で調製されたカオチン性リポソームとを混合し、氷冷下で10分間放置することによって各リポプレックスを調製した。
上記で得られたリポプレックス100μLに、3-MGluPG/リポプレックスの電荷比が、0.25、0.5、1、1.5、2となるように2.5〜20μLの3-MGluPG修飾リポソーム(EYPC濃度:0.2mM)を加え、氷冷下で10分間放置して、3-MGluPG修飾リポソーム・リポプレックス複合体を得た。
上記3-MGluPGに代えて、調製例2〜3で得られたSucpGまたはGluPGを用いた以外は、実施例1と同様にして複合体を得た。
上記で得られた各薬物担体およびコントロールとして複合化前のリポプレックスを用いて遺伝子導入試験を行った。
<細胞の調製とトランスフェクション>
HeLa細胞を24穴ディッシュに1穴当たり10万個撒き、10%ウシ胎児血清(FBS)含有ダルベッコ変法イーグル培地(DMEM)1mLを加えて、37℃で一晩培養した。その後PBSで2回洗浄した後、10%FBS含有DMEMを1.8mL加えた後、1穴当たり2μgのプラスミドDNAを含む各薬物担体またはリポプレックスを加え、4時間インキュベーションした。その後、再びPBSで2回洗浄し、取り込まれなかった複合体を除去し、10%FBS含有DMEM 2mLを加えて24 時間培養し、遺伝子発現割合を評価した。評価はフローサイトメトリーを用いて行い、約15000個の細胞をフローし、発現割合を求めた。結果を図2に示す。
<細胞の調整とトランスフェクション>
HeLa細胞を24穴ディッシュの1穴当たり5万個になるように撒き、10%FBS含有DMEMメディウム 1mLを加えて、37℃で一晩培養した。その後PBS(+)で洗浄した後10%FBS含有DMEMメディウム0.9mL を加えて、1穴当たり0.5μgのプラスミドDNA量を含むようにリポプレックスまたは3-MGluPG修飾リポソーム−リポプレックス複合体を細胞に加え、それぞれ4時間インキュベーションした。その際、3-MGluPG/リポプレックスの電荷比(すなわち、カルボン酸単位/DNAの比)は0.25、0.5、1、1.5、2の各5通りについて検討した。その後、再びPBS(+)で洗浄し、10%FBS含有DMEMメディウム1mLを加えて40時間培養した。
遺伝子導入した細胞をPBS(+)で洗浄し、さらにPBS(−)で1回洗浄した後、細胞を1穴当たり50μLの溶解剤に溶かし室温で15分間放置した。そのライセートをエッペンドルフチューブに回収して、12000rpmで2分間遠心分離した。そして、その細胞溶解液のうち10μLを用いて、細胞内のタンパク質の定量を行った。タンパク質の定量は、coomanassie Protein Assay Reagent(Pierce)を用い、波長595nmの吸光度を測定することによって、タンパク質濃度を求めた。また、残りの細胞溶解液20μLを、ルシフェリンを含んだ発光基質溶液95μLと混合し、ルミノメーターを使って20秒間の発光量を測定した。そして、細胞のタンパク質1mg当たりのルシフェラーゼ活性を求めた。結果を図3に示す。
このような特徴から、薬学的に許容し得る薬理的活性物質、生理的活性物質または診断用物質を封入させた本発明の薬物担体は、治療および診断という目的に対して非常に効果的であるといえる。
Claims (7)
- 前記薬物担体の粒子径が、0.02〜250μmである請求項1または2に記載の薬物担体。
- 前記担体粒子がリポソーム、ミセル、リピッドマイクロスフェアおよびエマルションからなる群より選ばれる少なくとも1種である請求項1〜3のいずれかに記載の薬物担体。
- 前記薬物担体が、安定化剤、酸化防止剤および前記(A)および(B)以外の表面修飾剤からなる群より選ばれる少なくとも1種の他の成分をさらに含む請求項1〜4のいずれかに記載の薬物担体。
- 前記薬物が、核酸、ポリヌクレオチド、遺伝子およびその類縁体;グリコサミノグリカンおよびその誘導体、オリゴ糖、多糖およびそれらの誘導体、タンパク質およびペプチド;抗炎症剤、ステロイド剤、抗癌剤、酵素剤、酵素阻害剤、抗生物質、抗酸化剤、脂質取り組み阻害剤、ホルモン剤、アンジオテンシン変換酵素阻害剤、アンジオテンシン受容体拮抗剤、平滑筋細胞の増殖・遊走阻害剤、血小板凝集阻害剤、ケミカルメディエーターの遊離抑制剤、血管内皮細胞の増殖または抑制剤、アルドース還元酵素阻害剤、メサンギウム細胞増殖阻害剤、リポキシゲナーゼ阻害剤、免疫抑制剤、免疫賦活剤、抗ウィルス剤、抗凝固剤、血管拡張剤、メイラード反応抑制剤、アミロイドーシス阻害剤、NOS阻害剤、AGEs阻害剤およびラジカルスカベンジャー;および体内診断薬からなる群より選ばれる少なくとも1種である請求項1〜5のいずれかに記載の薬物担体。
- 前記薬物担体が、核酸、ポリヌクレオチド、遺伝子およびその類縁体から選ばれる少なくとも1種の薬物を担持するリポプレックスとリポソームとの複合体である請求項1〜5のいずれかに記載の薬物担体。
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JP2010260986A (ja) * | 2009-05-11 | 2010-11-18 | Daicel Chem Ind Ltd | ポリグリシドール誘導体、及びこれを含む複合薬物担体 |
US8445712B2 (en) | 2009-11-13 | 2013-05-21 | Nof Corporation | Phospholipid derivative and pH-responsive liposomes |
JPWO2015079952A1 (ja) * | 2013-11-29 | 2017-03-16 | テルモ株式会社 | アジュバント組成物およびこれを含むワクチン組成物、並びにこれらの製造方法 |
CN113603799A (zh) * | 2021-06-30 | 2021-11-05 | 南昌大学 | 一种高抗氧化性的米糠多糖-肽复合物及其制备方法 |
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JP2005008623A (ja) * | 2003-05-27 | 2005-01-13 | Terumo Corp | 薬物担体 |
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Cited By (4)
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JP2010260986A (ja) * | 2009-05-11 | 2010-11-18 | Daicel Chem Ind Ltd | ポリグリシドール誘導体、及びこれを含む複合薬物担体 |
US8445712B2 (en) | 2009-11-13 | 2013-05-21 | Nof Corporation | Phospholipid derivative and pH-responsive liposomes |
JPWO2015079952A1 (ja) * | 2013-11-29 | 2017-03-16 | テルモ株式会社 | アジュバント組成物およびこれを含むワクチン組成物、並びにこれらの製造方法 |
CN113603799A (zh) * | 2021-06-30 | 2021-11-05 | 南昌大学 | 一种高抗氧化性的米糠多糖-肽复合物及其制备方法 |
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