JP2009523767A - 難水溶性有効物質を製剤化するための両親媒性自己集合タンパク質の使用 - Google Patents
難水溶性有効物質を製剤化するための両親媒性自己集合タンパク質の使用 Download PDFInfo
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Images
Classifications
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Abstract
Description
(i)難水溶性有効物質を共通分散相において両親媒性自己集合タンパク質と混合し、
(ii)続いてタンパク質及び有効物質を多く含む相と、タンパク質及び有効物質をわずかに含む相への相分離を行う、
方法を提供する。
両親媒性自己集合タンパク質は、アミノ酸、特に20個の天然アミノ酸から構成されるポリペプチドからなる。アミノ酸はまた、修飾、例えばアセチル化、グリコシル化、ファルネシル化されていてもよい。
以下本明細書において、難水溶性有効物質及び疎水性有効物質、並びに疎水性活性物質及びエフェクター分子という用語は同義に用いられる。以下本明細書において、難水溶性有効物質という用語は、その20℃における水溶性が5重量%未満、好ましくは1重量%未満、特に好ましくは0.5重量%未満、特に非常に好ましくは0.1重量%未満である化合物を意味するために用いられる。
特に有利な色素は、下記のリストに特定されている油溶性又は油分散性化合物である。カラーインデックス番号(CIN)は、Rowe Colour Index, 3rd edition, Society of Dyers and Colourists, Bradford, England, 1971から採用する。
3−ベンジリデンカンフル及びその誘導体、例えば3−(4−メチルベンジリデン)カンフルなど;
4−アミノ安息香酸誘導体、好ましくは4−(ジメチルアミノ)安息香酸2−エチルヘキシル、4−(ジメチルアミノ)安息香酸2−オクチル及び4−(ジメチルアミノ)安息香酸アミル;
ケイヒ酸のエステル、好ましくは4−メトキシケイヒ酸2−エチルヘキシル、4−メトキシケイヒ酸プロピル、4−メトキシケイヒ酸イソアミル、4−メトキシケイヒ酸イソペンチル、2−シアノ−3−フェニルケイヒ酸2−エチルヘキシル(オクトクリレン);
サリチル酸のエステル、好ましくはサリチル酸2−エチルヘキシル、サリチル酸4−イソプロピルベンジル、サリチル酸ホモメンチル;
ベンゾフェノンの誘導体、好ましくは2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−4’−メチルベンゾフェノン、2,2’−ジヒドロキシ−4−メトキシベンゾフェノン;
ベンザルマロン酸のエステル、好ましくは4−メトキシベンズマロン酸ジ−2−エチルヘキシル;
トリアジン誘導体、例えば2,4,6−トリアニリノ−(p−カルボ−2’−エチル−1’−ヘキシルオキシ)−1,3,5−トリアジン(オクチルトリアゾン)及びジオクチルブタミドトリアゾン(Uvasorb(登録商標) HEB)など;
プロパン−1,3−ジオン、例えば、1−(4−tert−ブチルフェニル)−3−(4’−メトキシフェニル)プロパン−1,3−ジオンなど
である。
ベンゾイルメタンの誘導体、例えば、1−(4’−tert−ブチルフェニル)−3−(4’−メトキシフェニル)プロパン−1,3−ジオン、4−tert−ブチル−4’−メトキシジベンゾイルメタン又は1−フェニル−3−(4’−イソプロピルフェニル)プロパン−1,3−ジオンなど、
ベンゾフェノンのアミノヒドロキシ置換誘導体、例えば、n−ヘキシル安息香酸N,N−ジエチルアミノヒドロキシベンゾイルなどである。
難水溶性活性物質の製剤は、両親媒性自己集合タンパク質を用いて種々の方法で調製することができる。難水溶性の疎水性活性物質は、タンパク質微粒子に封入されるか、又は例えば微粒化バッチにおいて達成することのできるタンパク質皮膜によってコロイド分散状態で安定化される。疎水性活性物質の製剤化は、微粒子への封入によって行うことができる。この方法は、2つのステップを含む。最初のステップにおいて、疎水性活性物質及び両親媒性自己集合タンパク質を共通相に溶解する。このために、該活性物質及び該タンパク質は溶媒又は溶媒混合物に直接溶解することができる。あるいは、該活性物質及び該タンパク質は最初に異なる溶媒に溶解することができ、その後、それらの溶液を一緒に混合し、それによって共通相を生成する。共通相は、分子分散相又はコロイド分散相のいずれでもよい。
β−カロテン溶液の調製
80mgのβ−カロテン及び16mgのトコフェロールを10gのTHFに溶解することによりストック溶液を調製した。次に、このストック溶液から、表1.1に示す希釈によって溶液1〜4を調製した。
β−カロテンをC16タンパク質微粒子に封入するために、C16タンパク質とβ−カロテンの共通相を最初に調製した。このために、各場合に5mMリン酸カリウム(pH8)中10mg/mlのC16タンパク質の溶液500μlを5μl又は100μlのβ−カロテン溶液と混合した(溶液1〜4)(表1.2)。THF/イソプロパノールからのβ−カロテンを含むバッチ(バッチ1〜4)の場合にはオレンジ色分散液が得られ、THFからのβ−カロテンを含むバッチ(バッチ5〜8)の場合には黄色分散液が得られた。
β−カロテン及びC16タンパク質の共通相へのリン酸カリウムの直接添加とは別に、1Mリン酸カリウムに対する透析によっても相分離を行うことができる。透析を透析管で実施したため、リン酸カリウム溶液の直接添加と比べて10倍のバッチ容量を各場合にピペットで添加した(表1.3)。
C16タンパク質微粒子におけるβ−カロテンをタンパク質分解によって放出することができることを示すために、200μlの微粒子分散水溶液G1及びG2を500μlの5Mリン酸カリウム(pH8.0)と混合した。続いて5μlのプロテイナーゼK(Roche,19.45mg/ml)を添加し、混合物を室温で一晩インキュベートした。各場合に、プロテイナーゼKを用いないC16タンパク質微粒子分散液の混合物を対照として用いた。一晩インキュベートした後、混合物を遠心した。
β−カロテンを含有するC16タンパク質微粒子を、ヒトの胃及び/又は腸において活性を有する種々のプロテアーゼで処理することによって、医薬有効物質の貯蔵、輸送及び/又は送達系としてのタンパク質微粒子の安定性を実証することを目的とした。
図5:445nmにおける吸収の光度測定によるC16タンパク質微粒子から放出されたβ−カロテンの測定。
2gの結晶質リコピン及び0.4gのα−トコフェロールを500gのTHFに溶解した。活性物質溶液を、流速25.4g/分で5mMリン酸カリウムバッファー(pH8)中の0.2g/lのC16タンパク質からなる水溶液と、室温でかつ流速2.42g/分で連続的に混合した。THF/水混合物での混合時に形成される活性物質粒子は粒径103nmを有していた。2時間後、未処理サンプル(図6A)と比べてC16タンパク質で処理したサンプル(図6B)の透明な分散液の安定化が観察された。その数日後でさえも、C16タンパク質を含むリコピン分散液は安定のようであったが、未処理リコピン分散液は大部分が凝集した(図7)。C16タンパク質で安定化されたリコピン分散液の一部は、濃縮して0.28%の固形含量となった。この状態で、乾燥したリコピンはほどんど再分散することができなかった。別法において、C16タンパク質で安定化されたリコピン分散液を330mMリン酸カリウム(混合物中の最終濃度)で処理し、乾燥した。得られたリコピン粉末は容易に再分散可能であった。
難水溶性植物活性物質を両親媒性自己集合タンパク質から調製されたタンパク質微粒子に封入し、またそれから放出することができる。このため、非限定的な例として除草剤活性物質メタザクロルを選択した。
酸素ラジカル、UVなどの影響に対して不安定な難水溶性又は水不溶性活性物質を、両親媒性自己集合タンパク質から調製されたタンパク質微粒子内に封入することができる。これらはまた、その後にそれらから放出することができる。さらに、タンパク質微粒子への製剤化及び/又は封入の結果として、活性物質は、有害な影響及びそれから生じる分解に対して保護される。これを示すために、非限定的な例として活性物質レチノールを選択し、これをC16タンパク質微粒子に封入し、空気スパージング及び均一混合しながら数時間撹拌した。さまざまな時点においてサンプルを取り出し、残存するレチノールをTHF抽出によって定量した。
難水溶性又は水不溶性の薬理活性を有する物質を、両親媒性自己集合タンパク質から調製されたタンパク質微粒子に封入することができる。これらはまた、その後にそれらから放出することができる。さらに、タンパク質微粒子への製剤化及び/又は封入により、これらの活性物質は、例えば特定のプロテアーゼ又は強酸性のpH値などの有害な影響及びそれから生じる分解に対して保護される。両親媒性自己集合タンパク質を用いたタンパク質微粒子への封入及び/又は微粒化バッチによって、良好に吸収される及び/又は良好なバイオアベイラビリティを示す特定の活性物質の粒子サイズ又は活性物質の構造を確立することができる。これを示すために、非限定的な例として活性物質イブプロフェン[(RS)−2−(4−イソブチルフェニル)プロピオン酸]を選択した。
Claims (16)
- 難水溶性有効物質を製剤化するための両親媒性自己集合タンパク質の使用。
- 両親媒性自己集合タンパク質が微粒子形成性タンパク質である、請求項1記載の使用。
- 両親媒性自己集合タンパク質が本質的に折りたたまれていないタンパク質である、請求項1記載の使用。
- 両親媒性自己集合タンパク質がシルクタンパク質である、請求項1記載の使用。
- 両親媒性自己集合タンパク質がクモシルクタンパク質である、請求項1記載の使用。
- 両親媒性自己集合タンパク質がC16クモシルクタンパク質である、請求項1記載の使用。
- 使用する有効物質が医薬活性成分である、請求項1〜6のいずれか1項に記載の使用。
- 使用する有効物質が作物保護活性成分である、請求項1〜6のいずれか1項に記載の使用。
- 使用する有効物質が皮膚及び毛髪化粧品用活性成分である、請求項1〜6のいずれか1項に記載の使用。
- (i)難水溶性有効物質を共通分散相において両親媒性自己集合タンパク質と混合し、
(ii)続いてタンパク質及び有効物質を多く含む相と、タンパク質及び有効物質をわずかに含む相への相分離を行う、
有効物質製剤の製造方法。 - 相分離(ii)をリオトロピック塩により実施する、請求項10記載の方法。
- 実施温度が5〜50℃である、請求項10記載の方法。
- タンパク質及び有効物質を多く含む相を硬化し、機械的に安定な有効物質含有タンパク質微粒子として分離し、そして適宜乾燥する、請求項10〜12のいずれか1項に記載の方法。
- 少なくとも1つの両親媒性自己集合タンパク質を用いて製剤化された難水溶性有効物質とさらなる化粧品用助剤を含む化粧品調製物。
- 少なくとも1つの両親媒性自己集合タンパク質を用いて製剤化された難水溶性有効物質とさらなる医薬品用助剤を含む医薬調製物。
- 少なくとも1つの両親媒性自己集合タンパク質を用いて製剤化された難水溶性有効物質とさらなる農薬用助剤を含む農薬調製物。
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PCT/EP2007/050541 WO2007082936A1 (de) | 2006-01-20 | 2007-01-19 | Verwendung von amphiphilen selbstassemblierenden proteinen zur formulierung von schwer wasserlöslichen effektstoffen |
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JP2008550765A Pending JP2009523766A (ja) | 2006-01-20 | 2007-01-19 | 化粧品におけるタンパク質マイクロビーズの使用 |
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EP (2) | EP1978937A1 (ja) |
JP (2) | JP5236498B2 (ja) |
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2007
- 2007-01-19 CA CA002638870A patent/CA2638870A1/en not_active Abandoned
- 2007-01-19 WO PCT/EP2007/050541 patent/WO2007082936A1/de active Application Filing
- 2007-01-19 US US12/161,352 patent/US20100278882A1/en not_active Abandoned
- 2007-01-19 WO PCT/EP2007/050517 patent/WO2007082923A2/de active Application Filing
- 2007-01-19 CN CNA2007800030880A patent/CN101370481A/zh active Pending
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JP2021502365A (ja) * | 2017-11-10 | 2021-01-28 | ジボダン エス エー | シルクアルコール製剤 |
JP7320846B2 (ja) | 2017-11-10 | 2023-08-04 | ジボダン エス エー | シルクアルコール製剤 |
Also Published As
Publication number | Publication date |
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JP5236498B2 (ja) | 2013-07-17 |
JP2009523766A (ja) | 2009-06-25 |
CA2637065C (en) | 2014-03-18 |
WO2007082923A2 (de) | 2007-07-26 |
CN101370556A (zh) | 2009-02-18 |
EP1978937A1 (de) | 2008-10-15 |
WO2007082936A1 (de) | 2007-07-26 |
CN104856962A (zh) | 2015-08-26 |
CA2637065A1 (en) | 2007-07-26 |
US20100278882A1 (en) | 2010-11-04 |
US20100278883A1 (en) | 2010-11-04 |
EP1979055A2 (de) | 2008-10-15 |
US8288512B2 (en) | 2012-10-16 |
CA2638870A1 (en) | 2007-07-26 |
CN101370481A (zh) | 2009-02-18 |
WO2007082923A3 (de) | 2007-10-04 |
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