JP2019059740A - 高度分岐α−D−グルカン - Google Patents
高度分岐α−D−グルカン Download PDFInfo
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- JP2019059740A JP2019059740A JP2018211734A JP2018211734A JP2019059740A JP 2019059740 A JP2019059740 A JP 2019059740A JP 2018211734 A JP2018211734 A JP 2018211734A JP 2018211734 A JP2018211734 A JP 2018211734A JP 2019059740 A JP2019059740 A JP 2019059740A
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- glucan
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Abstract
Description
本出願は、2012年4月19日にファイルされた米国仮特許出願第61/635,453号の優先権の利益を主張し、その内容を本明細書に援用する。
本発明は、少なくとも部分的に、補助金DMR1006301のもとで、米国国立科学財団による政府の援助により支援された。このため、本発明には、米国政府が一定の権利を保有する。
「高度分岐アルファ−D−グルカン」(高度分岐α−D−グルカン)という用語は、本明細書で使用する場合、グリコーゲン、フィトグリコーゲン、アミロペクチン、またはそれらの修飾型などの、α−D−グルコース分子から形成される高度に分岐した多糖をいう。いくつかの実施形態では、多糖は、α−D−1,4グルコシド結合およびα−D−1,6グルコシド結合によって結合されている。しかしながら、他の実施形態では、化学修飾(たとえば、焙焼デキストリン化)を利用して、α−D−1,2結合およびα−D−1,3結合などの他のタイプの結合を含む高度分岐α−D−グルカンを提供してもよい。高度分岐α−D−グルカンは、植物素材、微生物(たとえば、細菌)あるいは、人間または人間以外の動物から得られるか、誘導できるか、抽出することが可能であり、グルコース、グルカン、または他の物質から合成することも可能である。一例では、高度分岐α−D−グルカンは、グリコーゲン、フィトグリコーゲン、アミロペクチン、および/またはそれらの修飾型、たとえばオクテニルコハク酸(OS)またはポリエチレングリコール(PEG)で修飾されたもの、を含む。
分岐密度のパーセンテージ=α−D−1,6グルコシド結合数/(α−D−1,4グルコシド結合数+α−D−1,6グルコシド結合数)×100
通常、分岐密度は、グルカン分子中のすべてのグルコシド結合をもとにした分岐点のパーセンテージである。
一態様では、本明細書に記載の発明は、溶質化合物の溶解性を向上させるための組成物を提供する。「溶質化合物」という用語は、本明細書では、都合のよい言い回しとして用いられているが、高度分岐α−D−グルカンは、溶質化合物の物理的、化学的、または物理化学的な安定性を向上させる目的のような、溶解性を向上させる以外の目的でも使用可能であることに注意されたい。溶質化合物の物理的安定性は、溶質化合物のアモルファス形態、結晶サイズ、結晶構造、または結晶形態(たとえば、多形)、またはこれらの組み合わせについての安定性を含む。溶質化合物の化学的安定性は、酸化、還元、化学反応、構造の変化または分解に対する耐性、あるいはこれらの組み合わせについての安定性を含む。物理化学的安定性は、物理的安定性、化学的安定性、またはこれらの組み合わせを含む。
高度分岐α−D−グルカンまたはその修飾型を溶質化合物と混合することは、多岐にわたる利点を与える。いくつかの実施形態では、本発明は、溶質化合物を有効量の高度分岐α−D−グルカンと混合することで、溶質化合物の溶解性、溶解速度、および/または安定性を向上させる方法を提供する。
本発明のもうひとつの態様は、可溶性組成物を調製するための方法に関連する。一実施形態では、この方法は、溶質化合物を溶媒に溶解して溶液を形成し、この溶液を高度分岐α−D−グルカンまたはその修飾型と混合し、溶媒を除去して可溶性組成物を得ることを含む。いくつかの実施形態では、溶媒は、非水性溶媒と水性溶媒の混合物である。
su1含有スイートコーンの熟した穀粒を使用して、フィトグリコーゲンを抽出した。クェルセチンおよびクルクミンは、Sigma-Aldrich(St. Louis, MO)から購入し、さらに精製することなく使用した。クェルセチン(7mg/mL)およびクルクミン(4.25mg/mL)のストック溶液をエタノールで調製し、琥珀色のボトルに入れて暗所にて4℃で保管した。使用した他の化学物質的は、分析試薬グレードのものであった。全体をとおして、脱イオン水を使用した。
スイートコーン穀粒を挽いて粗挽きのグリットにした後、4〜6重量比の脱イオン水と混合した。この懸濁液を高速ブレンダー(Waring Laboratory, Torrington, CT)で均質化した後、8000×gで20分間遠心処理した。上清を回収する一方で、脱イオン水を用いて固体をさらに2回抽出した。その後、それぞれのバッチの上清を合わせ、270メッシュのふるいに通した。次に、この液体をエタノールに加えて多糖を沈殿させた。遠心処理および上清のデカント後、沈殿物をエタノールで再分散させ、遠心処理した。最後のエタノール追加後の懸濁液を濾過し、余分な液体を除去した。固体をドラフトに入れ、残留エタノールを除去した。回収された粉末は、フィトグリコーゲンを含有している。
フィトグリコーゲンの懸濁液に、1−オクテニルコハク酸無水物を加えた。NaOHを用いて、pHを8.5〜9.0の間に維持した。24時間後、HClを用いてpHを6.5まで下げることで、反応を終えた。置換されたグルカンを回収するために、3容量のエタノールを反応混合物に加えた。沈殿物を回収し、3サイクルのエタノール懸濁−遠心処理を用いて、さらに脱水した。濾過後に回収した固体をドラフトに入れ、残留エタノールを除去した。
フィトグリコーゲンの水性分散液10mlを、0.1%、0.5%、1.0%、5.0%で、Na2HPO4−クエン酸緩衝液(pH6.6)にて調製し、ネジ口試験管に充填した。クェルセチンまたはクルクミンのストック溶液のアリコート0.1mLをフィトグリコーゲン分散液に加えた後、22℃で2時間、攪拌する。その後、溶解しないクェルセチンまたはクルクミンを遠心処理によって除去した。
水性系中のクェルセチンの濃度を、CEを使用して求めた。このCE実験は、分光光度検出器を備えたBeckman製の機器であるMDQ P/ACE(Palo Alto, CA, USA)を用いて行った。分離は、Polymicro Technologies(Phoenix, AZ, USA)から入手した、コーティングされていない溶融シリカキャピラリー(47.0cm×内径50μm×外径375μm)を用いて行った。キャピラリーの温度は25℃に維持した。254nmで、UV検出を行った。0.05Mのホウ酸からなるランニングバッファー(pH9.0)を使用した。印加電圧は正の極性で20kVとした。標準溶液を含むすべての試料を0.45μmのシリンジフィルターで濾過した。移動度の測定を3重に行った。ピーク領域の定量には、Beckman 32 karatソフトウェア(バージョン7.0)を使用した。
クルクミン−フィトグリコーゲン混合物をエタノールに加え、多糖を沈殿させるとともに、クルクミンを抽出した。遠心処理後、上清をUV−Vis分光光度計(Varian Instruments, Walnut Creek, CA)で測定した。溶液の吸光度を、クルクミンを使用しないこと以外は同一の試薬濃度で調製した試薬ブランクを対照として、425nmで測定した。80%エタノール中クルクミン1.0〜8.0μg/mlの溶液を用いて、標準曲線を作成した。
図3は、様々な濃度のフィトグリコーゲン分散液におけるクェルセチンの溶解性を示す。フィトグリコーゲンの濃度を上昇させると、クェルセチンの溶解性の有意な上昇が認められた。クェルセチン単独(0.0%フィトグリコーゲン)の場合と比較して、1.0%および5.0%のフィトグリコーゲンを用いると、クェルセチンの溶解性がそれぞれ5.0倍および97.4倍ほど上昇した。
様々な濃度のフィトグリコーゲンにおけるクルクミンの溶解性を図4に示す。クルクミンの推定水溶性は、11.0ng/mLと報告されていた(Kaminaga et al. Letters, 555, 311-316 (2003))。本発明者らの試験では、クルクミンの溶解性は、検出限界(0.30μg/mL)未満であった。フィトグリコーゲンまたはPG−OSの濃度が高くなるにつれて、クルクミンの溶解性の有意な向上が認められた。たとえば、クルクミンの溶解性は、5.0%フィトグリコーゲンおよびPG−OS分散液で、それぞれ29.1および31.8μg/mLであったが、これはクルクミン単独の場合に報告されている値よりも、ほぼ3,000倍高い。
3グラムのフィトグリコーゲンと5.85グラムのオクテニルコハク酸無水物(OSA)を15.0mLのジメチルスルホキシド(DMSO)中で混合した後、50mLの試験管に移した。この試験管を沸騰した湯浴に3時間入れ、反応させた。その後、反応物を2つに分けた。片方の半分をPG−OS−PEGの調製に使用し、もう片方の半分をPG−OSを単離させるのに使用した。PG−OSを単離するために、20倍の脱イオン水を加えて反応を停止させ、この液体を、NaOH溶液を用いてpH6.5まで中和した。次に、この液体に限外濾過プロセスをほどこした。
14mLの試験管で、30mgのPG−OS、PG−OS−PEG、β−シクロデキストリン(βCD)、ヒドロキシプロピルβ−シクロデキストリン(HPβCD)をそれぞれ2.97mLの酢酸ナトリウム(NaAC)緩衝液(10mM、pH6.5)と混合した。各混合物に、過剰量のクルクミン粉末を加え、この混合物を、高速ホモジナイザ(T25-DS1 Ultra-Turrax(登録商標)、IKA)を用いて7分間、22,000rpmで処理した。その後、各混合物から1.0mLのアリコートを抜き、遠心処理をほどこした。上清をエタノールに加え、クルクミンを抽出した。沈殿物を除去するための遠心処理後、80%エタノールで上清をさらに希釈し、UV−Vis分光光度計(Varian Instruments)を用いて425nmで、標準曲線に対するクルクミン含有量を求めた。表1は、10mg/mLのキャリアと複合体形成した場合のクルクミンの溶解性を示す。明らかに、PG−OSおよびPG−OS−PEGはともにCDβおよびHPβCDよりもクルクミンの水溶解性を改善する機能が高かった。
表1:キャリアによって影響される、pH6.5の10mM NaAc緩衝液におけるクルクミンの溶解性
**HPβCD:ヒドロキシプロピルβ−シクロデキストリン
PG−Sを調製するために、3グラムのフィトグリコーゲンおよび3.7グラムの無水コハク酸(SA)を15.0mLのジメチルスルホキシド(DMSO)中で混合した後、50mLの試験管に移した。この試験管を沸騰湯浴に3時間入れ、反応させた。PG−Sを単離するために、20倍の脱イオン水を加えて反応を停止させ、この液体を、NaOH溶液を用いてpH6.5まで中和した。次に、この液体に限外濾過プロセスをほどこした。
グリセオフルビン(Sigma-Aldrich)0.55グラム、1.65グラムのPG−SまたはPG−S−PEG、6.05グラムのDMSOを、乳鉢および乳棒を用いて混合した。この混合物をガラスバイアルに移し、真空乾燥させて、DMSOを完全に除去した。対照として、複合体形成の場合と同じ比でグリセオフルビンをDMSOに溶解し、真空乾燥させてグリセオフルビン固体を回収した。また、対照として、グリセオフルビンとPG−SまたはPG−S−PEGとの物理的混合物を1/3の比で調製した。
フィトグリコーゲン−イブプロフェン複合体を調製するために、イブプロフェン、フィトグリコーゲン、DMSOを、重量比1:3:6または1:5:10で混合した。得られるペーストを真空にいれてDMSOを除去し、回収した固体を微粉砕して粉末にした。一方、DMSOを用いて同様に(DMSOに溶解後に溶媒を除去)してイブプロフェンを処理し、回収された固体をいくつかの対照試料の調製に使用した。フィトグリコーゲンと、もとのイブプロフェンまたはDMSO処理したイブプロフェンの乾燥混合物を調製した。これらの物質をDSCおよびX線粉末回折分析に使用した。
10mgのクルクミンを1.0mLのエタノール中で混合し、ボルテックスし、遠心処理して、上清を回収することで、クルクミンがエタノール中に含まれるストック溶液を調製した。一方、2グラムのフィトグリコーゲンを40mLのNa2HPO4−クエン酸緩衝液(pH3.0〜6.6)に分散させた。0.4mLのクルクミンストック溶液をフィトグリコーゲン分散液に加えた。この混合物を遠心処理して、溶解しないクルクミンを除去した。上清を回収し、凍結乾燥させてフィトグリコーゲン−クルクミン複合体形成固体を調製した。
3グラムのフィトグリコーゲンと3グラムのチモール(Sigma-Aldrich)を酢酸ナトリウム緩衝液(50mM、pH5.5)に分散させ、どちらも10%(w/v)とした。この混合物に高速均質化処理をした。均質化後、分散液を遠心処理し、水性の液体を回収した。このフィトグリコーゲン−チモール液体ストック中のチモール濃度を求めたところ、約400μg/mLであった。参照用として、チモールを緩衝液に加えてボルテックスすることで、チモールが単独で酢酸ナトリウム緩衝液(50mM、pH5.5)に含まれるストック400μg/mLを調製した。
Claims (28)
- 高度分岐α−D−グルカンまたはその修飾型と、前記高度分岐α−D−グルカンが存在しない場合より向上した水溶解性を有する溶質化合物と、を含む、溶質化合物の溶解性を向上させるための組成物。
- 前記高度分岐α−D−グルカンは、パーセンテージ分岐密度が約7%である、請求項1に記載の組成物。
- 前記高度分岐α−D−グルカンは、樹状構造を有する、請求項1に記載の組成物。
- 前記高度分岐α−D−グルカンは、グリコーゲン、フィトグリコーゲン、またはその修飾型である、請求項1に記載の組成物。
- 水性溶媒に対する前記溶質化合物の溶解速度は、前記高度分岐α−D−グルカンが存在しないときの前記溶質化合物の溶解速度よりも向上している、請求項1に記載の組成物。
- 前記溶解性は、前記高度分岐α−D−グルカンが存在しないときの前記溶質化合物の溶解性に比して少なくとも約2倍に向上している、請求項1に記載の組成物。
- 前記高度分岐α−D−グルカンは、修飾された高度分岐α−D−グルカンである、請求項1に記載の組成物。
- 前記修飾された高度分岐α−D−グルカンは、アセトキシ、リン酸、オクテニルコハク酸、コハク酸、ヒドロキシプロピル、ヒドロキシエチル、カチオン基、カルボキシメチル、ポリエチレングリコール(PEG、またはポリエチレンオキシド)、ポリプロピレングリコール(またはポリポロピレンオキシド)、またはこれらの組み合わせから選択される化学基を少なくとも含有する、請求項7に記載の組成物。
- 前記修飾された高度分岐α−D−グルカンは、抗体、抗原、アプタマー、タンパク質、ペプチド、アミノ酸、シクロデキストリン、糖類、脂質、核酸およびヌクレオチド、デンドリマー、酵素、蛍光基または染料、磁性基、金属イオン、金属ナノ粒子、量子ドット、ポリマーおよびブロックコポリマー、放射性基、またはこれらの組み合わせから選択される少なくとも1つの基を含有する、請求項7に記載の組成物。
- 前記修飾された高度分岐α−D−グルカンは、酸加水分解、酸化、焙焼デキストリン化、α−アミラーゼ、β−アミラーゼ、脱分枝酵素、トランスグルコシダーゼ、アミログルコシダーゼおよび/またはプロテアーゼを用いる酵素処理、漂白、剪断力処理、押出、混練、均質化、水熱処理、乾燥加熱、マイクロ波処理、放射線、またはこれらの組み合わせから選択される少なくとも1つの処理によって調製される、請求項7に記載の組成物。
- 前記溶質化合物は、疎水性化合物である、請求項1に記載の組成物。
- 前記溶質化合物は、フェノール化合物である、請求項1に記載の組成物。
- 前記溶質化合物は、カロテノイド、クルクミノイド、フラボノイド、ステロール、フィトステロール、サポニン、サポゲニンからなる群から選択される、請求項1に記載の組成物。
- 前記溶質化合物は、薬剤、ビタミン、殺虫剤、除草剤、酸化防止剤、ハーブエキス、漢方薬、着色剤、ホルモン、エッセンシャルオイル、またはこれらの組み合わせからなる群から選択される、請求項1に記載の組成物。
- 前記溶質化合物は、クルクミン、クェルセチン、ルテイン、レスベラトロール、レシチン、チモール、パクリタキセル、イブプロフェン、グリセオフルビンからなる群から選択される、請求項1に記載の組成物。
- 前記組成物は、
少なくとも1種類の溶質化合物を第1の溶媒に溶解または分散させ、第1の溶液または分散液を形成する工程と、
少なくとも1種類の高度分岐α−D−グルカンまたはその修飾型を第2の溶媒に溶解または分散させ、第2の溶液または分散液を形成する工程と、
前記第1および第2の溶液または分散液を一緒に混合し、混合物を形成する工程と、
前記混合物から前記溶媒を除去して組成物を得る工程と、
を含む方法を用いて調製され、
前記組成物中の前記溶質化合物の水溶性は、前記少なくとも1種類の高度分岐α−D−グルカンが存在しないときの前記溶質化合物の水溶性より向上している、請求項1に記載の組成物。 - 前記方法は、前記溶質化合物の溶解速度および/または安定性を向上させる、請求項16に記載の組成物。
- 混練、押出、均質化、超音波、高圧処理、高速処理、マイクロ波処理、放射線処理、熱処理、またはこれらの組み合わせによって、前記混合物を処理する工程をさらに含む、請求項16に記載の組成物。
- 前記溶媒は、噴霧乾燥、真空乾燥、凍結乾燥、ドラム乾燥、押出、超臨界抽出、またはこれらの組み合わせによって、前記混合物から除去される、請求項16に記載の組成物。
- 前記組成物は、他の成分をさらに含み、
前記他の成分は、薬学的に許容されるキャリアを含むがこれに限定されるものではない成分である、請求項1に記載の組成物。 - 前記溶質化合物および前記高度分岐α−D−グルカンは、高度分岐α−D−グルカンに対する溶質化合物の質量比が約100:1から約1:1000の範囲で提供される、請求項1に記載の組成物。
- 溶質化合物の溶解性、溶解速度、および/または安定性を向上させる方法であって、少なくとも1種類の高度分岐α−D−グルカンまたはその修飾型と、前記溶質化合物とを混合することを含む、方法。
- 前記混合が、少なくとも溶媒の存在下でなされる、請求項22に記載の方法。
- 混練、押出、均質化、超音波、高圧処理、高速処理、マイクロ波処理、放射線処理、熱処理、またはこれらの組み合わせによって、前記混合物を処理する工程をさらに含む、請求項22に記載の方法。
- 前記溶媒は、噴霧乾燥、真空乾燥、凍結乾燥、ドラム乾燥、熱乾燥、押出、超臨界抽出、またはこれらの組み合わせによって前記混合物から除去される、請求項23に記載の方法。
- ポリエチレングリコール(PEG)またはポリエチレンオキシド(PEO)の化学基を少なくとも含有する、修飾されたフィトグリコーゲンまたはグリコーゲン物質。
- 前記物質は、アセトキシ、リン酸、オクテニルコハク酸、コハク酸、ヒドロキシプロピル、ヒドロキシエチル、カチオン基、カルボキシメチル、ポリプロピレングリコール(またはポリプロピレンオキシド)、またはこれらの組み合わせから選択される化学基をさらに含む、請求項26に記載の物質。
- 前記物質は、溶質化合物の特性を改善し、
前記特性は、水溶解性、溶解速度、および/または、結晶化、酸化、分解、劣化、還元もしくは構造変化に対する安定性、あるいはこれらの組み合わせを含む、請求項26に記載の物質。
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