JP2012056857A - 線維芽細胞増殖促進剤、角化細胞遊走・増殖促進剤、エラスチン産生促進剤、ヒートショックタンパク質47産生促進剤、α−平滑筋アクチン(α−SMA)産生促進剤、及び光老化防止剤。 - Google Patents
線維芽細胞増殖促進剤、角化細胞遊走・増殖促進剤、エラスチン産生促進剤、ヒートショックタンパク質47産生促進剤、α−平滑筋アクチン(α−SMA)産生促進剤、及び光老化防止剤。 Download PDFInfo
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Abstract
【解決手段】 本発明は、一般式(1)または(2)で表される化合物を有する、線維芽細胞増殖促進剤、角化細胞遊走・増殖促進剤、エラスチン産生促進剤、ヒートショックタンパク質47産生促進剤、及びα−平滑筋アクチン(α−SMA)産生促進剤、光老化防止剤を提供する。
【選択図】なし
Description
(式中、R1、R2、R4、R5は、同一又は異なっていてもよく、水素又は−O−C(=O)R7を示す。R7は炭素数1〜8のアルキル基を示す。R3は水素又は炭素数1〜4のアルキル基又はアルケニル基又は−C(=O)R8を示す。R8は炭素数1〜8のアルキル基を示す。R6は、−CH=CH−R9又は−C≡C−R9を示す。R9は水素又は炭素数1〜8のアルキル基を示す。)で表される化合物が、線維芽細胞の増殖能を高め、角化細胞の遊走・増殖能を高め、ヒートショックタンパク質47の産生能を高め、エラスチンの産生能を高め、およびα−SMAの産生能を高め、光老化防止の機能を有すること見出して、本発明を完成した。
(式中、R1、R2、R4、R5は、同一又は異なっていてもよく、水素又は−O−C(=O)R7を示す。R7は炭素数1〜4のアルキル基を示す。R3は、水素又は炭素数1〜4のアルキル基又はアルケニル基又は−C(=O)R8を示す。R8は炭素数1〜8のアルキル基を示す。R6は水素又は炭素数1〜4のアルキル基又は−C(=O)R9を示す。R9は炭素数1〜8のアルキル基を示す。)で表される化合物を有する、線維芽細胞増殖促進剤、角化細胞遊走・増殖促進剤、エラスチン産生促進剤、α−平滑筋アクチン(α−SMA)産生促進剤、ヒートショックタンパク質47産生促進剤、または光老化防止剤である。
本発明で使用する線維芽細胞の増殖能を高め、角化細胞の遊走・増殖能を高め、ヒートショックタンパク質47の産生能を高め、エラスチンの産生能を高め、α−SMAの産生能を高め、および光老化を防止する物質は、一般式(1)または(2)で表される化合物である。
(式中、R1、R2、R4、R5は、同一又は異なっていてもよく、水素又は−O−C(=O)R7を示す。R7は炭素数1〜8のアルキル基を示す。R3は水素又は炭素数1〜4のアルキル基又はアルケニル基又は−C(=O)R8を示す。R8は炭素数1〜8のアルキル基を示す。R6は、−CH=CH−R9又は−C≡C−R9を示す。R9は水素又は炭素数1〜8のアルキル基を示す。)
(式中、R1、R2、R4、R5は、一又は異なっていてもよく、水素又は−O−C(=O)R7を示す。R7は炭素数1〜4のアルキル基を示す。R3は、水素又は炭素数1〜4のアルキル基又はアルケニル基又は−C(=O)R8を示す。R8は炭素数1〜8のアルキル基を示す。R6は水素又は炭素数1〜4のアルキル基又は−C(=O)R9を示す。R9は炭素数1〜8のアルキル基を示す。)
本実施例で用いた線維芽細胞は、以下のようにして培養したものを用いた。すなわち、TCフラスコ50mL(株式会社グライナー・ジャパン)を用いて、ヒト正常皮膚由来線維芽細胞(CCD−1059SK、DSファーマメディカル株式会社)は、10%牛胎児血清(FBS、株式会社ニチレイバイオサイエンス)、ペニシリン(50units/ml、明治製菓株式会社)およびストレプトマイシン(50mg/ml、明治製菓株式会社)を含むダルベッコ修正イーグル培地(Dulbecco’s modified Eagle’s medium(DMEM))(日水製薬株式会社)に1.25×105個播き、サブコンフルエント(約80%密度)になるまで約1週間培養した。次いで、培地を除去し、細胞をPBS2mLで1回洗浄し、更に0.01%EDTA/0.025%トリプシン溶液(和光純薬工業株式会社)3mLで細胞を剥離させ、トリプシン中和液3mLを添加して細胞を回収し、遠心分離(4℃、1,300rpm、5分)して上清を除き、細胞を得た。この細胞を前記条件下で繰り返し培養して継代培養した。
本実施例で用いた角化細胞は、以下のようにして培養したものを用いた。すなわち、TCフラスコ50mL(株式会社グライナー・ジャパン)を用いて、ヒトケラチノサイト(HaCat細胞)は、10%牛胎児血清(FBS、株式会社ニチレイバイオサイエンス)、ペニシリン(50units/ml、明治製菓株式会社)およびストレプトマイシン(50mg/ml、明治製菓株式会社)を含むダルベッコ修正イーグル培地(Dulbecco’s modified Eagle’s medium(DMEM))(日水製薬株式会社)に1.25×105個播き、サブコンフルエント(約80%密度)になるまで約1週間培養した。次いで、培地を除去し、細胞をPBS2mLで1回洗浄し、更に0.01%EDTA/0.025%トリプシン溶液(和光純薬工業株式会社)3mLで細胞を剥離させ、トリプシン中和液3mLを添加して細胞を回収し、遠心分離(4℃、1,300rpm、5分)して上清を除き、細胞を得た。この細胞を前記条件下で繰り返し培養して継代培養した。回収したケラチノサイトは、直径35mmのプラスチックシャーレ(株式会社グライナー・ジャパン)に2.25×105個播きコンフルエント状態になるまで培養した。この後、ピペットチップで細胞を直線状に掻き取った。培地を除去した後、濃度が0.1μM、1.0μMとなるようにACAを添加した前記培地中で、さらに24時間培養を続けた。なお、コントロールとして、ACAを添加しないものを用いた。
細胞数を1.0×105cells/mlに調整して、直径60mmのプラスチックシャーレ(株式会社グライナー・ジャパン)に6.0×105cellsずつ播種し、濃度が1.0μMとなるようにACAを添加した培地中で、24時間培養を続けた。なお、コントロールとして、ACAを添加しないものを用いた。細胞内エラスチンをウェスタンブロッティング法により解析した。用いた抗エラスチン抗体は、Monoclonal Antibody to Elastin−Ascites(Acris Antibodies GmbH)であった。結果を図3に示す。
細胞数を1.0×105cells/mlに調整して、直径60mmのプラスチックシャーレ(株式会社グライナー・ジャパン)に6.0×105cellsずつ播種し、濃度が0.1μMとなるようにACAを添加した培地中で、24時間培養を続けた。なお、コントロールとして、ACAを添加しないものを用いた。なお、コントロールとして、ACAを添加しないものを用いた。細胞内I型コラーゲン量をウェスタンブロッティング法により解析した。用いた抗I型コラーゲン抗体は、COL1A1(C−18)(SANTA CRUZ BIOTECHNOLOGY,INC)であった。結果を図4に示す。
細胞数を1.0×105cells/mlに調整して、直径60mmのプラスチックシャーレ(株式会社グライナー・ジャパン)に6.0×105cellsずつ播種し、濃度が0.1μMとなるようにACAを添加した培地中で、24時間培養を続けた。なお、コントロールとして、ACAを添加しないものを用いた。なお、コントロールとして、ACAを添加しないものを用いた。細胞内α−SMA量をウェスタンブロッティング法により解析した。用いた抗α−SMA抗体は、Mouse Anti−Human Smooth Muscle Actin(1A4)(Dako A/S)であった。結果を図5に示す。
細胞数を1.0×105cells/mlに調整して、直径60mmのプラスチックシャーレ(株式会社グライナー・ジャパン)に6.0×105cellsずつ播種し、濃度が0.1μMとなるようにACAを添加した培地中で、24時間培養を続けた。なお、コントロールとして、ACAを添加しないものを用いた。なお、コントロールとして、ACAを添加しないものを用いた。細胞内HSP47量をウェスタンブロッティング法により解析した。用いた抗HSP47抗体は、Anti−HSP47 Mouse Monoclonal (Stressgen BIOREAGENTS.CORP)であった。結果を図6に示す。
細胞数を1.0×105cells/mlに調整して、直径35mmのプラスチックシャーレ(株式会社グライナー・ジャパン)に1.0×105cellsずつ播種し、濃度が1.0μMとなるようにACAを添加した培地中で、3時間培養を続けた。ACAを添加した培地を用いた細胞と、ACAを添加しない培地を用いた細胞とに、UVを20μW、60秒間照射した。その後、さらに1時間培養し、ヒト皮膚繊維芽細胞の活性酸素種産生量を測定した。測定方法として、蛍光顕微鏡による観察法と蛍光光度計による細胞内活性酸素種産生量の測定法を用いた。上記UV照射後30分後に、各培地に細胞浸透性蛍光プローブ 2’,7’−ジクロロフルオレセインジアセテート(2’,7’−Dichlorofluorescin diacetate(DCFH−DA))を加えてさらに30分間培養を続けた。培地を取り除き、PBSで2回洗浄後、カバーガラスをかけて蛍光顕微鏡下で観察し、写真撮影を行った。一方、蛍光光度計による測定には、培養終了後、PBSで2回洗浄して、Hanks溶液で細胞を掻きとり、細胞液を96穴プレートに入れてマルチラベルカウンター(Wallac 1420 ARVOsx)を用いて、励起波長485nm、蛍光波長535nmで蛍光度を測定した。なお、コントロールとして、ACAを添加せずに、UVを照射しないものを用いた。
Claims (7)
- 一般式(1)
(式中、R1、R2、R4、R5は、同一又は異なっていてもよく、水素又は−O−C(=O)R7を示す。R7は炭素数1〜8のアルキル基を示す。R3は水素又は炭素数1〜4のアルキル基又はアルケニル基又は−C(=O)R8を示す。R8は炭素数1〜8のアルキル基を示す。R6は、−CH=CH−R9又は−C≡C−R9を示す。R9は水素又は炭素数1〜8のアルキル基を示す。)で表される化合物を有する、線維芽細胞増殖促進剤、角化細胞増殖促進剤、エラスチン産生促進剤、α−平滑筋アクチン(α−SMA)産生促進剤、ヒートショックタンパク質47産生促進剤、または光老化防止剤。 - 前記一般式(1)で表される化合物が、1’−アセトキシチャビコールアセテート(ACA)、1−アセトキシ−1−(2,4−ジアセトキシフェニル)−2−プロペン、及び1−アセトキシ−1−(3,4−ジアセトキシフェニル)−2−プロペンである、請求項1に記載の線維芽細胞増殖促進剤、角化細胞増殖促進剤、エラスチン産生促進剤、α−平滑筋アクチン(α−SMA)産生促進剤、ヒートショックタンパク質47産生促進剤、または光老化防止剤。
- 一般式(2)
(式中、R1、R2、R4、R5は、同一又は異なっていてもよく、水素又は−O−C(=O)R7を示す。R7は炭素数1〜4のアルキル基を示す。R3は、水素又は炭素数1〜4のアルキル基又はアルケニル基又は−C(=O)R8を示す。R8は炭素数1〜8のアルキル基を示す。R6は水素又は炭素数1〜4のアルキル基又は−C(=O)R9を示す。R9は炭素数1〜8のアルキル基を示す。)で表される化合物を有する、線維芽細胞増殖促進剤、角化細胞遊走・増殖促進剤、エラスチン産生促進剤、α−平滑筋アクチン(α−SMA)産生促進剤、ヒートショックタンパク質47産生促進剤、または光老化防止剤。 - 前記一般式(2)で表される化合物が、4−((E)−3−ヒドロキシ−1−プロペニル)フェニルアセテート、及び2−アセトキシ−4−((E)−3−ヒドロキシ−1−プロペニル)フェニルアセテート、及び3−アセトキシ−4−((E)−3−ヒドロキシ−1−プロペニル)フェニルアセテートである請求項3に記載の線維芽細胞増殖促進剤、角化細胞遊走・増殖促進剤、エラスチン産生促進剤、α−平滑筋アクチン(α−SMA)産生促進剤、ヒートショックタンパク質47産生促進剤、または光老化防止剤。
- 請求項1〜4いずれかに記載の促進剤または防止剤を有する医薬品類。
- 請求項1〜4のいずれかに記載の促進剤または防止剤を有する医薬部外品類。
- 請求項1〜4のいずれかに記載の促進剤または防止剤を有する化粧品類。
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