JP5929907B2 - ピロロキノリンキノンと糖を含むリポソーム - Google Patents
ピロロキノリンキノンと糖を含むリポソーム Download PDFInfo
- Publication number
- JP5929907B2 JP5929907B2 JP2013515202A JP2013515202A JP5929907B2 JP 5929907 B2 JP5929907 B2 JP 5929907B2 JP 2013515202 A JP2013515202 A JP 2013515202A JP 2013515202 A JP2013515202 A JP 2013515202A JP 5929907 B2 JP5929907 B2 JP 5929907B2
- Authority
- JP
- Japan
- Prior art keywords
- sugar
- liposome
- pyrroloquinoline quinone
- solution
- salt
- 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.)
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- 239000002502 liposome Substances 0.000 title claims description 131
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Description
(1)リポソーム組成物であって、該リポソーム組成物におけるリポソームが、下記式(1):
(2)リポソームの体積平均粒子経が、0.5〜20μmである、(1)に記載のリポソーム組成物。
(3)糖が、単糖、二糖、オリゴ糖、多糖、および糖アルコールからなる群から選択される、(1)に記載のリポソーム組成物。
(4)糖が、ソルビトールまたはキシリトールである、(1)に記載のリポソーム組成物。
(5)(1)〜(4)のいずれかに記載のリポソーム組成物を含んでなる、食品。
(6)(1)〜(4)のいずれかに記載のリポソーム組成物を含んでなる、医薬品。
(7)(1)〜(4)のいずれかに記載のリポソーム組成物を含んでなる、培地。
(8)下記式(1):
(9)溶液のpHが、8以下である、(8)に記載の製造方法。
(10)溶液におけるピロロキノリンキノンまたはその塩の濃度が、0.0001〜2重量%であり、糖が0.5〜50重量%である、(8)に記載の製造方法。
(11)溶液におけるピロロキノリンキノンまたはその塩と、糖と、脂質成分との重量比が、1:1〜200:0.1〜30である、(8)に記載の製造方法。
(12)溶液をホモジナイズする工程をさらに含んでなる、(8)に記載の製造方法。
(13)(8)に記載の製造方法により製造される、リポソーム組成物。
〔1〕下記式(1);
〔2〕糖がソルビトール又はキシリトールである〔1〕記載のリポソーム。
〔3〕〔2〕記載のリポソームを含む食品。
〔4〕〔2〕記載のリポソームを含む医薬品。
〔5〕〔2〕記載のリポソームを含む培地。
〔6〕ピロロキノリンキノンと糖を溶解させた水溶液を、pHを8以下に調製した後、60℃から190℃に加温する工程を含む、リポソームの製造方法。
〔7〕前記水溶液におけるピロロキノリンキノン若しくはその塩の濃度が0.0001〜2重量%であり、糖が2から50重量%である〔6〕記載のリポソームの製造方法。
〔8〕ホモジナイザーを使用する工程を含む、〔7〕記載の製造方法。
ピロロキノリンキノンジナトリウムは三菱ガス化学、COATSOME NC-21(水素添加大豆リン脂質)は日本油脂、その他はWAKOの試薬を使用した。
SEISHIN LMS−350(セイシン企業社製)を使用して、水に分散して粒度分布を求めた。この装置では0.1μmが検出下限である。
PQQジナトリウム0.3g、COATSOME NCー21(水素添加大豆リン脂質)3.0gを用い、水を全体が100gになるように混合した。この時のpHは3.5であった。得られた溶液を60℃以上に加温しながら、NISSEI AMー3ホモジナイザー(株式会社日本精機製作所社製)で30分、7000回転、その後、室温に下げ、10分、7000回転で処理した。処理後、蒸発減少した水分を追加した。これを比較例1のリポソーム組成物とした。
PQQジナトリウム0.3g、COATSOME NCー21(水素添加大豆リン脂質)3.0gを用い、ソルビトールの添加を2,10,20,40gで行い、水は全体が100gになるように混合した。この時のpHは3.5であった。また、温度は60℃であった。得られた溶液を比較例1と同様に処理して、実施例1−4のリポソーム組成物を作製した。
COATSOME NCー21(水素添加大豆リン脂質)3.0g、ソルビトール10gを用い、全体が100gとなる様に水を混合した。比較例1と同様に処理してリポソーム組成物を作製した。
大豆レシチン0.3g、PQQジナトリウム0.3g、ソルビトール10gを用い、全体が100gとなる様に水を混合した。比較例1と同様の操作を行いリポソーム組成物を作製した。
ソルビトールの添加による粒子径の変化は小さく、糖添加によるリポソームの粒子径への影響はないことが分かった。PQQ添加の有無も粒子径への影響はないことが分かった。
比較例3は一般的な大豆レシチンにすることで小さな粒子を含むリポソームを作ることができ、小さな粒子の影響を見ることができる。
チャイニーズハムスター卵巣細胞(CHO−DHFR;大日本住友製薬より入手)をα−MEM+10%牛胎児血清の培地で5%CO2, 37℃で培養した。イワキ製96穴プレートを使用し、1個の穴に5000個の細胞になるように100μlの培地とともに加え、一晩培養した。培養液を抜き、所定の試験濃度の実施例1ー4、比較例1ー3で調製したリポソーム組成物を含む培地を加えた。1日培養後、培地を入れ替え同仁化学 WSTアッセイキットを使用して1時間反応させ、450nmの吸光度を測定した。この時の吸光度は細胞数に比例する。
増殖促進濃度は、比較例1より実施例1−4の方が広い濃度範囲で有効であった。
リポソームにPQQと糖を添加すると増殖停止濃度は上がり、増殖抑制効果は糖の添加により、小さくなった。
比較例2のPQQを添加しない糖添加のリポソーム組成物では500μM相当では細胞増殖に影響がみられたが、その他では影響がない。また、比較例3の小さなリポソーム組成物では低い濃度で増殖阻害が現れ、増殖促進効果は見られない(試験範囲よりも低い濃度になっていると予想される)。
細胞の増殖を促進する濃度が広くなることで培地に添加する際の組成選択が容易になると考えられる。
PQQジナトリウム0.3g、ソルビトール10g、COATSOME NCー21(水素添加大豆リン脂質)3.0gに、水を全体が100gになるように混合した。この時のpHは3.5であった。また、温度は40℃であった。得られた溶液の温度を上げながら、最終的に60℃以上になるように加温しながら、NISSEI AM−3ホモジナイザーで30分、7000回転、その後、室温に下げ、30分、7000回転で処理した。処理後、合計重量100gになるように蒸発減少した水分を追加した。
PQQジナトリウム0.3g、ソルビトール50または0.5g、COATSOME NCー21(水素添加大豆リン脂質)3.0gに、水を全体が100gになるように混合した。この時のpHは3.5であった。また、温度は60℃であった。実施例1〜4と同様に処理してリポソーム組成物を作製した。
また、糖の濃度が0.5重量%、50重量%でも広い濃度範囲で増殖促進できることが確認された(実施例6および7)。
PQQジナトリウム0.3g、COATSOME NCー21(水素添加大豆リン脂質)3.0g、糖を表6に示す重量を用い、全体が100gとなるように水を混合した。この時のpHは3.5であった。また、温度は60℃であった。得られた溶液のNISSEI AMー3ホモジナイザーによる処理は以下のように行い、実施例8−12のリポソーム組成物を作製した。
実施例8:80℃以上に加温しながら1時間、7000回転
実施例9:40℃以上に加温しながら30分、7000回転
実施例10:60℃以上加温しながら30分、7000回転、その後、室温に下げ、1時間、7000回転
実施例11および12:60℃以上加温しながら30分、7000回転
また、糖については、糖アルコールのみならず単糖、二糖でも広い濃度範囲で増殖促進できることが確認された(実施例11および12)。
Claims (10)
- 脂質成分として水素添加大豆リン脂質を含むリポソーム組成物であって、該リポソーム組成物におけるリポソームが、下記式(1):
の粒子径のリポソームが45%以上であり、糖がグルコース、ショ糖及びソルビトールからなる群から選択される糖である、リポソーム組成物。 - リポソームの体積平均粒子経が、0.5〜20μmである、請求項1に記載のリポソー
ム組成物。 - 請求項1又は2に記載のリポソーム組成物を含んでなる、食品。
- 請求項1又は2のいずれか一項に記載のリポソーム組成物を含んでなる、医薬品。
- 請求項1又は2のいずれか一項に記載のリポソーム組成物を含んでなる、培地。
- 下記式(1):
- 溶液のpHが、8以下である、請求項6に記載の製造方法。
- 溶液におけるピロロキノリンキノンまたはその塩の濃度が、0.0001〜2重量%で
あり、糖が0.5〜50重量%である、請求項6に記載の製造方法。 - 溶液におけるピロロキノリンキノンまたはその塩と、糖と、水素添加大豆リン脂質との重量比が、1:1〜200:0.1〜30である、請求項6に記載の製造方法。
- 溶液をホモジナイズする工程をさらに含んでなる、請求項6に記載の製造方法。
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JP5672751B2 (ja) * | 2010-04-07 | 2015-02-18 | 三菱瓦斯化学株式会社 | ピロロキノリンキノンを含むリポソーム |
WO2012070649A1 (ja) | 2010-11-26 | 2012-05-31 | 三菱瓦斯化学株式会社 | 溶解性の高いピロロキノリンキノン塩及びその製造方法 |
CN105816344B (zh) * | 2015-12-28 | 2018-08-17 | 天津伊瑞雅生物科技有限公司 | 一种含有吡咯并喹啉醌和n-乙酰基神经氨酸的组合物 |
EP3701801A4 (en) * | 2017-10-25 | 2021-06-23 | Mitsubishi Gas Chemical Company, Inc. | JELLY CANDY CONTAINING A QUINONE PYRROLOQUINOLEIN, AND METHOD FOR MANUFACTURING THE SAME |
US11344497B1 (en) * | 2017-12-08 | 2022-05-31 | Quicksilver Scientific, Inc. | Mitochondrial performance enhancement nanoemulsion |
EP3813788A1 (en) * | 2018-06-27 | 2021-05-05 | Breath Therapeutics GmbH | Pharmaceutical compositions in lyophilized form |
EP3845074A4 (en) * | 2018-08-30 | 2021-10-27 | Mitsubishi Gas Chemical Company, Inc. | PHOTODEGRADATION INHIBITOR, DRINK WITH IT AND PROCESS FOR INHIBITING PHOTODEGRADATION |
WO2020045562A1 (ja) * | 2018-08-30 | 2020-03-05 | 三菱瓦斯化学株式会社 | ピロロキノリンキノンの安定化剤、それを含む組成物及び安定化方法 |
CN117063919B (zh) * | 2023-10-13 | 2024-01-30 | 北京市农林科学院 | 吡咯喹啉醌在提高精液冷冻效果中的用途 |
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