JP5918783B2 - マイクロrnaの制御因子を用いて皮膚を治療する方法 - Google Patents
マイクロrnaの制御因子を用いて皮膚を治療する方法 Download PDFInfo
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- NCTHNHPAQAVBEB-WGCWOXMQSA-M sodium ferulate Chemical compound [Na+].COC1=CC(\C=C\C([O-])=O)=CC=C1O NCTHNHPAQAVBEB-WGCWOXMQSA-M 0.000 description 1
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- 229940012831 stearyl alcohol Drugs 0.000 description 1
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- 230000035882 stress Effects 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 239000000516 sunscreening agent Substances 0.000 description 1
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- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- 229960002663 thioctic acid Drugs 0.000 description 1
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- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
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- 229960001727 tretinoin Drugs 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
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Description
(a)小皺又は皺の治療、低減、及び/又は防止
(b)皮膚の細孔の大きさの低減
(c)皮膚の厚さ、ふくよかさ、及び/又はつっぱりの改善
(d)皮膚のしなやかさ及び/又は柔らかさの改善
(e)皮膚の色調、輝き、及び/又は透明感の改善
(f)エラスチンの維持及び再形成の改善
(g)皮膚の肌理の改善及び/又は再組織化(retexturization)の促進
(h)皮膚のバリア修復及び/又は機能の改善
(i)皮膚の輪郭の外観の改善
(j)皮膚の艶及び/又は明るさの回復
(k)閉経により低下した皮膚の外観の改善
(l)皮膚の保湿の改善
(m)皮膚の弾力性及び/又は伸縮性の増加
(n)皮膚の弛みの治療、低減、及び/又は防止、又は、
(o)色素斑の低減
(a)小皺又は皺の治療、低減、及び/又は防止
(b)皮膚の細孔の大きさの低減
(c)皮膚の厚さ、ふくよかさ、及び/又はつっぱりの改善
(d)皮膚のしなやかさ及び/又は柔らかさの改善
(e)皮膚の色調、輝き、及び/又は透明感の改善
(f)プロコラーゲン及び/又はコラーゲンの生成の改善
(g)エラスチンの維持及び再形成の改善
(h)皮膚の肌理の改善及び/又は再組織化(retexturization)の促進
(i)皮膚のバリア修復及び/又は機能の改善
(j)皮膚の輪郭の外観の改善
(k)皮膚の艶及び/又は明るさの回復
(l)皮膚中での必須の栄養素及び/又成分の補充
(m)閉経により低下した皮膚の外観の改善
(n)皮膚の保湿の改善
(o)皮膚の弾力性及び/又は伸縮性の改善
(p)皮膚の弛みの治療、低減、及び/又は防止、又は、
(q)色素斑の低減
若者の皮膚線維芽細胞中と年配者の皮膚線維芽細胞中でのmiR−29a及びmiR−29bの発現をqRT−PCTで調査した。3組のドナー細胞を用いて実験を行った(つまり、3人の若者のドナー(22〜28歳)と3人の年配のドナー(55〜66歳))。HDFa細胞を、約80パーセントコンフルエントまで培養した。Taqman microRNA Cells−to−Ct Kitを用いて、細胞を溶解した。miR特異的プライマーとTaqMan MicroRNA Reverse Transcription Kitを用いて、cDNAを調製した。事前に設計されたTaqMan MicroRNA Assayを用いて、hsa−miR−29aとhsa−miR−29b、及びコントロールであるRNU6BとGAPDH(Applied Biosystemsから購入)に対してqPCRを実施した。以下の表1に纏めたデータによれば、若者に比べて年配者の皮膚線維芽細胞中では、miR−29aとmiR29bのレベルが顕著に高いことが説明される。
特定のマイクロRNA、miR29a及びmiR29bが、コラーゲン、フィブリリン及びエラスチンなどの真皮内のマトリックスタンパク質の発現を制御する能力を、55歳の年配のドナーからのヒト真皮線維芽細胞を用いて評価した。siSPORT NeoFX transfection Agent(Ambion製)を用いて、細胞に、60ナノメートルの抗miR−29a又は抗miR−29bの何れか(市販の試薬)を形質移入した。72時間の形質移入後、細胞を収集し、コラーゲンとフィブリリンのmRNAレベルをqRT−PCRで測定し、エラスチンのタンパク質レベルをELISAで測定した。これらの実験によって、miR−29a又はmiR−29bを抑制すると、コラーゲン、フィブリリン及びエラスチンの正味の発現レベルを増加できることが明らかになった(表3)。p<0.05の場合、全ての値は、統計的に有意である。
ヒト真皮線維芽細胞を無血清の状態で一昼夜成長させた後、無血清の状態で0.0005パーセントの試験化合物で48時間処理した。実施例1及び2に記載されたように、細胞のmiR−29aとmiR−29bの発現レベルを、qRT−PCRで分析した。0.0005パーセントのN−(2−メチルプロピル)−N−[[4−[(メチルスルフォニル)オキシ]フェニル]メチル]−ベンゼンスルホンアミド(1)又は2−(4−ベンジルピペリジン−1−イル)−N−(3−エトキシプロピル)−5−[(2E)−3−フェニルプロプ−2−エンナミド]ベンズアミド(2)で処理された細胞は、ビヒクルで処理された細胞と比べて、miR−29a及びmiR−29bの両方について顕著な阻害を示していた(表3)。これらの化合物で処理された細胞では、ELISAで測定されたように、コラーゲンタンパク質のレベルが増加することが示された。p<0.05の場合、全ての値は、統計的に有意である。
本出願は、米国特許法第119条(e)に基づいて、2010年12月28日に出願された米国特許出願第12/979,695号の優先権の利益を主張し、該出願の内容の全てはここに参照されて包含される。
(付記)
(付記1)
化粧品として許容されるビヒクル中の有効量の有効成分を、皮膚中のコラーゲン、エラスチン、及び/又はフィブリリンの生成を高めるのに十分な時間、改善を必要とする皮膚の領域に局所的に塗布することを含み、
前記有効成分は、配列UAGCACCAUCUGAAAUCGGUUA(配列番号1)を有するmiR−29a、及び/又は配列UAGCACCAUUUGAAAUCAGUGUU(配列番号2)を有するmiR−29bを抑制する、
人間の皮膚の美的外観を改善する方法。
(付記2)
前記有効成分は、miR−29aを抑制する、
付記1に記載の人間の皮膚の美的外観を改善する方法。
(付記3)
前記有効成分は、miR−29bを抑制する、
付記1に記載の人間の皮膚の美的外観を改善する方法。
(付記4)
前記有効成分は、miR−29a及びmiR−29bを抑制する、
付記1に記載の人間の皮膚の美的外観を改善する方法。
(付記5)
前記有効成分は、式Iの構造を有する化合物、及びその化粧品として許容される酸付加塩である、
(ここで、R1及びR2は、独立して、水素、−R、又は−C(=O)R*であり、R1及びR2は、これらが結合される窒素原子と共に、3〜6員環を形成してもよく;
R3は、水素、−R、−OR*、−SR*、及び−N(RN)(R*)の中から選ばれ;
R4及びR5は、各存在位置において、水素、−R、またはX1の中から独立して選ばれ;隣接する任意の2個のR5基は、これらが結合されるベンゼン環に縮合される5又は6員間を形成してもよく;
R6は水素、−R、又は−C(=O)R*であり;
R、R*、及びRNは、独立して、水素、又はC1−20の炭化水素基であり;ここで、前記C1−20の炭化水素基は、必要に応じて、X1基、及び/又は、酸素、窒素、及び硫黄の中から選ばれる1〜12個のヘテロ原子で置換されてもよく;
X1は、−F、−Cl、−Br、−I、−OH、−C≡C−R*、−C≡N、−C(R)=N−RN、−C=N−N(RN)2、−C(=NRN)−N(RN)2、−CH2OH、−CHO、−(C=O)−R*、−CO2H、−CO2 −、−CO2R*、−CS2R*、−(C=O)−S−R*、−S−(C=O)−R*、−(C=O)−NH2、−(C=O)−NRNRN、−(C=O)−NHNH2、−O−(C=O)−NHNH2、−(C=S)−NH2、−(C=S)−N(RN)2、−O−(C=O)−H、−O−(C=O)−R*、−O−(C=O)−NH2、−O−(C=O)−NRNRN、−OR*、−SR*、−NH2、−NHRN、−NRN 2、−N(RN)3 +、−N(RN)−OH、−N(→O)(R*)2、−O−N(RN)2、−N(RN)−O−R*、−N(RN)−N(RN)2、−NRN−(C=O)−R*、−NRNC(=O)O−R*、−NRN−CHO、−NRN−(C=O)−R*、−NRNC(=O)NRN、−N(RN)−C(=O)−N(RN)2、−N(RN)−C(=S)−N(RN)2、−N=C(R*)2、−N=N−RN、−SCN、−NCS、−NSO、−SS−R*、−SO−R*、−SO2−R*、−O−S(=O)2−R*、−S(=O)2−OR*、−N(RN)−SO2−R*、−SO2−N(R*)2、−O−SO3 −、−O−S(=O)2−OR*、−O−S(=O)−OR*、−O−S(=O)−R*、−S(=O)−OR*、−S(=O)−R*、−NO、−NO2、−NO3、−O−NO、−O−NO2、−N3、−N2、−N(C2H4)、−Si(R*)3、−CF3、−O−CF3、−(C=O)−R*、−P(R*)2、−O−P(=O)(OR*)2、及び−P(=O)(OR*)2からなる群の中から選ばれ;
「n」は、0〜3までの整数であり、「n」が2又は3の場合、R5は、各存在位置において独立して選ばれる)
付記4に記載の人間の皮膚の美的外観を改善する方法。
R1、R2、R3、R4、及びR6は、独立して、水素又は−R基であり、
Rは、アルキル、アルケニル、アルキニル、アリール、アリールアルキル、及びアルキルアリールの中から選ばれ、それぞれ、必要に応じて、ハロゲン、酸素、窒素及び硫黄の中から選ばれる1〜12のヘテロ原子で置換される、
付記5に記載の人間の皮膚の美的外観を改善する方法。
(付記7)
R2、R3、及びR4は、独立して、−R基であり、
Rは、−(CH2)a−(CR*=CR*)b−(CH2)c−X2−(CH2)x−(CR*=CR*)y−(CH2)z−X3の形を有する基であり、
a、b、c、x、y及びzは、独立して、0〜5までの整数であり、
X2は、−O−、−S−、−C(=O)−、−N(RN)−、−C(=O)O−、−OC(=O)−、−C(=O)−N(RN)−の中から選ばれる、結合又は二価の基若しくは原子の何れかを表していて、
X3は、水素、X1、又はR*を表している、
付記6に記載の人間の皮膚の美的外観を改善する方法。
(付記8)
R1及びR6は水素である、
付記7に記載の人間の皮膚の美的外観を改善する方法。
(付記9)
R2は、−(CH2)a−X2−(CH2)x−CH3の形を有する基である、
付記8に記載の人間の皮膚の美的外観を改善する方法。
(付記10)
R3は、−CH=CH−R*の形を有する基であり、
R*はアリール基である、
付記8に記載の人間の皮膚の美的外観を改善する方法。
(付記11)
R4は、−(CH2)a−R*の形を有する基であり、
R*はアリール基である、
付記8に記載の人間の皮膚の美的外観を改善する方法。
(付記12)
R5は、水素である、
付記7に記載の人間の皮膚の美的外観を改善する方法。
(付記13)
前記有効成分は、以下の式を有する化合物であるか、又はその化粧品として許容される酸付加塩である、
付記8に記載の人間の皮膚の美的外観を改善する方法。
前記化合物は、式IIの構造を有するか、又は式IIの構造を有する化合物の化粧品として許容される塩である、
(ここで、R5は、水素、−R,又はX1の中から選ばれ;
「m」は、0〜5までの整数であり、「m」が2、3、又は4の場合、R5は、各存在位置において独立して選ばれ;
R7とR8は、独立して、C1−20の炭化水素基であり;
前記C1−20の炭化水素基は、必要に応じて、X1基及び/又は酸素、窒素、及び硫黄の中から選ばれる1〜6個のヘテロ原子で置換されてもよく;
R、R*、及びRNは、独立して、水素又はC1−20の炭化水素基であり;
前記C1−20の炭化水素基は、必要に応じて、X1基及び/又は酸素、窒素、及び硫黄の中から選ばれる1〜12個のヘテロ原子で置換されてもよく;
X1は、−F、−Cl、−Br、−I、−OH、−C≡C−R*、−C≡N、−C(R)=N−RN、−C=N−N(RN)2、−C(=NRN)−N(RN)2、−CH2OH、−CHO、−(C=O)−R*、−CO2H、−CO2 −、−CO2R*、−CS2R*、−(C=O)−S−R*、−S−(C=O)−R*、−(C=O)−NH2、−(C=O)−NRNRN、−(C=O)−NHNH2、−O−(C=O)−NHNH2、−(C=S)−NH2、−(C=S)−N(RN)2、−O−(C=O)−H、−O−(C=O)−R*、−O−(C=O)−NH2、−O−(C=O)−NRNRN、−OR*、−SR*、−NH2、−NHRN、−NRN 2、−N(RN)3 +、−N(RN)−OH、−N(→O)(R*)2、−O−N(RN)2、−N(RN)−O−R*、−N(RN)−N(RN)2、−NRN−(C=O)−R*、−NRNC(=O)O−R*、−NRN−CHO、−NRN−(C=O)−R*、−NRNC(=O)NRN、−N(RN)−C(=O)−N(RN)2、−N(RN)−C(=S)−N(RN)2、−N=C(R*)2、−N=N−RN、−SCN、−NCS、−NSO、−SS−R*、−SO−R*、−SO2−R*、−O−S(=O)2−R*、−S(=O)2−OR*、−N(RN)−SO2−R*、−SO2−N(R*)2、−O−SO3 −、−O−S(=O)2−OR*、−O−S(=O)−OR*、−O−S(=O)−R*、−S(=O)−OR*、−S(=O)−R*、−NO、−NO2、−NO3、−O−NO、−O−NO2、−N3、−N2、−N(C2H4)、−Si(R*)3、−CF3、−O−CF3、−(C=O)−R*、−P(R*)2、−O−P(=O)(OR*)2、及び−P(=O)(OR*)2からなる群の中から選ばれる)
付記1に記載の人間の皮膚の美的外観を改善する方法。
R7とR8は、独立して、−R基であり、
Rは、−(CH2)a−(CR*=CR*)b−(CH2)c−X2−(CH2)x−(CR*=CR*)y−(CH2)z−X3の形を有する基であり、
a、b、c、x、y、及びzは、独立して、0〜5までの整数であり、
X2は、−O−、−S−、−C(=O)−、−N(RN)−、−C(=O)O−、−OC(=O)−、−C(=O)−N(RN)−、−N(RN)−C(=O)−の中から選ばれる、結合又は二価の基若しくは原子の何れかを表していて、
X3は、水素、X1、又はR*を表していて、
R*は、C1−20の炭化水素基であり、該炭化水素は、必要に応じて、X1基及び/又は酸素、窒素、及び硫黄の中から選ばれる1〜12のヘテロ原子で置換される、
付記14に記載の人間の皮膚の美的外観を改善する方法。
(付記16)
RN、R7、及びR8は、独立して、−R基であり、
Rは、アルキル、アルケニル、アルキニル、アリール、アリールアルキル、及びアルキルアリールの中から選ばれ、それぞれ、必要に応じて、ハロゲン、酸素、窒素及び硫黄の中から選ばれる1〜12個のヘテロ原子で置換される、
付記15に記載の人間の皮膚の美的外観を改善する方法。
(付記17)
前記化合物は、以下の式を有するか、又は以下の式を有する化合物の化粧品として許容される塩である、
付記16に記載の人間の皮膚の美的外観を改善する方法。
前記皮膚の前記美的改善は、
(a)小皺又は皺の治療、低減、及び/又は防止、
(b)皮膚の細孔の大きさの低減、
(c)皮膚の厚さ、ふくよかさ、及び/又はつっぱりの改善、
(d)皮膚のしなやかさ及び/又は柔らかさの改善、
(e)皮膚の色調、輝き、及び/又は透明感の改善、
(f)エラスチンの維持及び再形成の改善、
(g)皮膚の肌理の改善及び/又は再組織化(retexturization)の促進、
(h)皮膚のバリア修復及び/又は機能の改善、
(i)皮膚の輪郭の外観の改善、
(j)皮膚の艶及び/又は明るさの回復、
(k)閉経により低下した皮膚の外観の改善、
(l)皮膚の保湿の改善、
(m)皮膚の弾力性及び/又は伸縮性の増加、
(n)皮膚の弛みの治療、低減、及び/又は防止、又は、
(o)色素斑の低減、
からなる群の中から選ばれる、
付記1に記載の人間の皮膚の美的外観を改善する方法。
(付記19)
細胞中のmiR−29a及び/又はmiR−29bを抑制する、又は下方制御させる能力について、候補物質を分析することを含む、
皮膚の美的外観を改善するのに有用な有効成分を同定する方法。
(付記20)
前記分析ステップには、前記候補物質を用いてヒト真皮線維芽細胞を培養し、次に、miR−29a及び/又はmiR−29bのレベルを測定することが含まれる、
付記19に記載の皮膚の美的外観を改善するのに有用な有効成分を同定する方法。
(付記21)
前記測定ステップは、qRT−PCRで実行される、
付記20に記載の皮膚の美的外観を改善するのに有用な有効成分を同定する方法。
(付記22)
皮膚中のコラーゲン、エラスチン、及び/又はフィブリリンの生成を向上して皮膚の美的外観を改善する方法であって、
該方法は、miR−29a及び/又はmiR−29bを抑制する有効量の有効成分を、改善を必要とする皮膚の領域に局所的に塗布することを含み、
前記有効成分は、細胞内のmiR−29a及び/又はmiR−29bの発現を抑制する物質の能力を測定する分析によって同定される、
皮膚の美的外観を改善する方法。
(付記23)
コラーゲン、エラスチン、フィブリリン、及びこれらの組み合わせからなる群から選ばれる細胞外マトリックスタンパク質を刺激して、老化した皮膚の外観を改善する方法であって、
改善を必要とする皮膚に、miR−29a及び/又はmiR−29bを抑制する有効成分を、局所的に許容されるビヒクル中に、有効量含む組成物を局所的に塗布することを含む、
老化した皮膚の外観を改善する方法。
(付記24)
前記有効成分は、以下の式を有する化合物であるか、又はその化粧品として許容される酸付加塩である、
付記23に記載の老化した皮膚の外観を改善する方法。
前記化合物は、以下の式を有するか、又は以下の式を有する化合物の化粧品として許容される塩である、
付記23に記載の老化した皮膚の外観を改善する方法。
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |