JP2007186445A - レゾルシノール誘導体を含有するメラニン生成抑制剤 - Google Patents
レゾルシノール誘導体を含有するメラニン生成抑制剤 Download PDFInfo
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- JP2007186445A JP2007186445A JP2006005063A JP2006005063A JP2007186445A JP 2007186445 A JP2007186445 A JP 2007186445A JP 2006005063 A JP2006005063 A JP 2006005063A JP 2006005063 A JP2006005063 A JP 2006005063A JP 2007186445 A JP2007186445 A JP 2007186445A
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- mmol
- melanin production
- dibenzyloxyphenyl
- acid
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims abstract description 18
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 title claims abstract description 14
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- 238000004519 manufacturing process Methods 0.000 abstract description 28
- 230000002401 inhibitory effect Effects 0.000 abstract description 12
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- 231100000135 cytotoxicity Toxicity 0.000 abstract description 7
- 230000002265 prevention Effects 0.000 abstract description 6
- 206010014970 Ephelides Diseases 0.000 abstract description 2
- 208000003351 Melanosis Diseases 0.000 abstract description 2
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Abstract
Description
〔1〕 下記一般式(I):
で示されるレゾルシノール誘導体(以下、レゾルシノール誘導体(I)と称することがある)を含有することを特徴とするメラニン生成抑制剤に関する。
本発明のメラニン生成抑制剤は、レゾルシノール誘導体(I)を含有することを特徴とする。かかる特徴を有することにより、本発明のメラニン生成抑制剤は、細胞においても実際に高いメラニン生成抑制作用を発揮し、かつ、細胞毒性が低いという優れた効果を奏する。さらに、本発明で使用されるレゾルシノール誘導体(I)は、高収率で調製され得ることから、本発明のメラニン生成抑制剤は、工業的に効率よく提供され得る。
この際、前述の任意成分の他に、前記の各形態に従来使用されている成分を適宜選択して配合することができる。
B16メラノーマ細胞を用いたメラニン生成抑制効果の評価
B16メラノーマ細胞をEMEM(Eagle's minimum essential medium、Nissui Pharmaceutical Co.製)中、1.0×105cells/mlの濃度に調節した後、24ウェルプレートに1mlずつ播種し、37℃、5%CO2下で24時間培養した。次いで、培地を、各濃度に調整した試料のジメチルスルホキシド(DMSO)溶液2μlを998μlのEMEMに添加して得た培地に交換し、48時間同条件で培養し、再度前記の試料を含むEMEMによる培地交換を行い24時間培養した。培地を除去後、1N 水酸化ナトリウム水溶液1mlで細胞を溶解し、プレートリーダーで405nmの吸光度を測定し、コントロールとして、試料を添加しないDMSO溶液を添加した場合を100%としたときの相対値でメラニン生成量を比較した。
B16メラノーマ細胞をEMEM中、1.0×105cells/mlの濃度に調節した後、24ウェルプレートに1mlずつ播種し、37℃、5%CO2下で24時間培養した。次いで、培地を、各濃度に調整した試料のジメチルスルホキシド(DMSO)溶液2μlを998μlのEMEMに添加して得た培地に交換し、48時間同条件で培養し、再度前記の試料を含むEMEMによる培地交換を行い、24時間培養した。その後、培地に5mg/mlのMTT(3−[4,5−ジメチルチアゾ−2−リル]−2,5−ジフェニルテトラゾリウム ブロミド)−PBS(phosphate buffered saline)溶液を各ウェルにつき50μl添加して4時間培養後、培地を除去し、MTT溶解液(濃塩酸340μl/イソプロパノール100ml)を1ml加え、10分間超音波処理した。生成物が完全に溶解したことを確認した後、該溶解液について、630nmを対照波長とし、570nmの吸光度を測定(570nmの吸光度−630nmの吸光度)し、試料無添加の場合の値(コントロール)を100%としたときの相対値を生存細胞数の相対値として評価した。
試料として、製造例11により得られた3−(2,4−ジヒドロキシフェニル)プロピオン酸(化合物4、比較例1、2)、製造例12により得られた4−(2,4−ジヒドロキシフェニル)ブタン酸(化合物5、比較例3、4)を、比較化合物として、4−ヘキシルレゾルシノール(化合物A、比較例5)を用いる以外は実施例1〜5と同じ操作を行い、B16メラノーマ細胞のメラニン生成量および生存細胞数を評価した。結果を図3に示す。
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