JP2016529322A - モノアセチルジアシルグリセロール化合物を有効成分に含有するアトピー皮膚炎の予防または治療用組成物 - Google Patents
モノアセチルジアシルグリセロール化合物を有効成分に含有するアトピー皮膚炎の予防または治療用組成物 Download PDFInfo
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- palmitoyl
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- atopic dermatitis
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Abstract
Description
[化学式1]
上記の式において、R1およびR2はそれぞれ炭素数14ないし20の脂肪酸基である。
[化学式2]
上記化学式2で表示される化合物は1−パルミトイル(palmitoyl)−2−リノレオイル(linoleoyl)−3−アセチルグリセロール(acetylglycerol)といい、本明細書でPLAGまたはEC−18とも命名される。前記化合物のR1とR2は、それぞれパルミトイルとリノレオイルに該当する。
[化学式1]
上記化学式1で表示されるモノアセチルジアシルグリセロール化合物においてR1およびR2はそれぞれ炭素数14ないし20の脂肪酸基であることができるが、これに限定されない。
[化学式1]
上記化学式1で表示されるモノアセチルジアシルグリセロール化合物においてR1およびR2はそれぞれ炭素数14ないし20の脂肪酸基であることができるが、これに限定されない。
[化学式1]
上記化学式1で表示されるモノアセチルジアシルグリセロール化合物においてR1およびR2はそれぞれ炭素数14ないし20の脂肪酸基であることができるが、これに限定されない。
DNCB (1-Chloro-2,4-dinitro-benzene, Sigma Aldrich)をアセトン:オリーブ油を4:1の比率で混合した溶媒に0.2%になるように希釈した後、背部位が除毛された7週齢Balb/cマウスの背に200μl (λ)ずつ塗布した。初一週間は7回を連続で塗布し、2週からは2日間隙で塗布してアトピーを誘導した。
EC-18をオリーブ油と混合して初一週間7回は2mg/匹で100μlずつ経口投与し、一週が経った後11回間1 mg/匹で100 μlずつ、総18回経口投与した。IL-4測定をために、投与したマウスの眼下静脈から眼球採血(Eye bleeding)方法を通じて血液を回収した。投与前、投与後1週、投与後2週、投与後3週、総4回にかけてパスツールピペット(pasteur pipet, Hilgenberg)を使用して採血した。EP tubeに約350μlぐらい血液を採取した後、遠心分離で血清だけを分離した後、血清に存在するIL-4をELISA(enzyme-linked immunosorbent assay)方法で分析した。マウスIL-4 ELISAはELISA用96-well plate(Thermo)にマウスIL-4 capture antibody(BD bioscience)を2 μg/mlで1X PBSに希釈し各ウェル(well)に200 μl分注した後、一夜間コーティングし、洗浄は1X PBSに0.05% tween 20を希釈した洗浄緩衝液(washing buffer)を使用した。3回洗浄後1%BSAを200 μlずつ各ウェルに分注しブロッキング緩衝液(blocking buffer)を室温(RT)条件で1時間実施した。その後洗浄は同じ条件で3回実施し、その後マウスで得た血清を100μlずつ各ウェル(well)に分注後2時間室温で反応させて、同一条件で5回洗浄した。洗浄後detection antibody (1:500) conjugated-HRP(1:250)を1% BSAに希釈し100 μlずつ各ウェルに分注した後室温で1時間反応させた。7回洗浄した後100 μlの基質溶液(substrate solution)を各ウェル(well)に分注後、光が遮断された状態で発色を観察した。発色が完了したらstop solution(2N H2SO4 + DW)を100 μlずつ分注した後ELISA Readerで450 nm波長の発色量を測定した。その結果、1週時と2週時のIL-4の数値(4回測定値の平均値)を比較したとき、オリーブ油を投与した対照群では約50%程度の減少幅を見せた反面、EC-18を投与した実験群ではIL-4の数値が約80%が減少された。つまり、アトピー誘導によって生成されたIL-4はEC-18の投与によって早く減少したのを確認した(図2)。
マウスの血液で分離した血清を利用し、上記実験例1と同じくELISA方法でIgEの発現程度を測定した。マウスIgE ELISAはELISA用96-well plate(Thermo)にマウスIgE capture antibody(BD bioscience)を2 μg/mlで1X PBSで希釈し各ウェル(well)に200 μlを分注した後12時間コーティングした。洗浄は1X PBSに0.05% tween 20を希釈した洗浄緩衝液(washing buffer)を使用し、3回洗浄後1% BSAを200 μlずつ各ウェル(well)に分注しブロックキング緩衝液(blocking buffer)を室温(RT)条件で1時間放置した後最後の洗浄を実施した。洗浄が終ったプレートにマウスから得た血清を100 μlずつ各ウェル(well)に分注し、1時間室温で反応させた後、反応しなかったIgEは同一条件で洗浄した。洗浄後detection antibody(BD bioscience)を1% BSAに2 μg/mlになるように希釈し100 μlずつ各ウェル(well)に分注した後、室温で1時間培養し、6回洗浄した後Streptoavidin-HRP(Thermo)を1:10,000の比率で1% BSAに希釈し100 μlずつ分注して反応したIgEに基質(substrate)を添加した。室温で30分間培養した後6回洗浄し、基質溶液(substrate solution)を各ウェル(well)に分注後光が遮断された状態で発色量を測定した。発色が完了したらstop solution(2N H2SO4 + DW)を50 μlずつ分注し450 nm波長で発色度を測定した。その結果、1週時と2週時のIgE数値を比較したとき、オリーブ油だけ処理した対照群は約22%程度減少された反面、EC-18を処理したグループでは約50%程度が減少された(図3)。
実験室で良く使用するアトピー疾患モデルはDNCB (1-Chloro- 2,4-dinitro-benzene)を感作させてContact Hypersensitivity (CHS)を誘導する技術だ。この技術は、アセトン:オリーブ油を4:1の比率で混合した溶媒にDNCBを 0.2 %がなるように希釈した後、これを皮膚に塗抹してアトピーを誘導する技術で、人為的にひどいアトピーと似たような外形的な形態を備えた時期を2週後に観察できるように調整して維持するための実験だ。アトピー疾患程度はアトピーが誘導された皮膚で紅斑/出血(Erythema/emorrhage)、傷/乾燥(Scarring/dryness)、浮腫(Edema)、擦傷/爛れ(Excoriation/erosion)状態を各々3段階に分けて(0点=無し、1点=軽症(mild)、2点=中間(moderate)、3点=重症(severe))、0点から12点までの点数を付与して評価した。実験群と対照群で、DNCBを塗抹した後、外形的にひどい状態のアトピー誘発状態(肉眼検査指数が10である状態)に到達する期間が2週後になるように誘導した。またひどいアトピーが誘導された2週後には、これを維持するために二日に一度ずつDNCBを塗抹した。
正常人(36名)にEC-18を4週間投与し、EC-18投与前と投与後に血液から分離したリンパ球をConA (concanavalin A)と共に培養した。ConAによって活性化されたリンパ球(T cell)から分泌されたcytokine(IFN-γ及びIL-4)を測定するために、培養液を42時間培養し、冷凍保管した。測定しようとするcytokineのpurified antibody(capture antibody)を0.2 μg/wellでwell (Nunc-immuno module, polysorp)に分注し、4 ℃でovernight放置し抗原をcoatingした。Wellを洗浄後、1時間程度blocking buffer(1% bovine serum albumin)で処理し非特異的結合を抑制した。その後wellを洗浄し細胞培養液を各wellにいれ2時間抗体がcoatingされた抗原と結合させた。その後peroxidaseまたはbiotinが結合されたantibodyを添加し、1時間室温で放置後洗浄した。Peroxidaseが結合されたantibodyはすぐTMB(3,3',5,5'-Tetramethyl benzidine) substrateを添加し、biotinが結合されたantibodyはSAv-HRP(Streptavidin-Horseradish Peroxidase)を添加し30分間反応させた後洗浄しTMB substrateを添加した。約10-30分程度後に、stop solutionを入れてAutomatic Microplate reader (Molecular Devices, CA, USA)で450-570 nmから吸光度を測定した。同じ方法で標準cytokine溶液濃度別吸光度を測定して標準曲線を作成し、試料群の吸光度を代入して、試料に含まれたcytokineの量を算出した。
ひどくアトピー症状を見せる患者へ、EC-18を毎日500 mg/dayの投与量で、2週間服用させた後、アトピー症状変化を撮影して図7に表し、軽微に皮膚の発疹が起きた患者にEC-18を二日間毎日500 mg/dayの投与量で服用させた後、アトピー症状変化を撮影して図8に表した。図7及び8に表したとおり、アトピー患者へEC-18を投与すれば、アトピー症状が緩和されることを確認できる。
Claims (14)
- 下記の化学式1で表示されるモノアセチルジアシルグリセロール化合物を有効性分として含有する、アトピー皮膚炎の予防または治療用薬学的組成物。
[化学式1]
上記の式において、R1およびR2はそれぞれ炭素数14ないし20の脂肪酸基である。 - 前記R1およびR2はそれぞれ、パルミトイル(palmitoyl)、オレオイル(oleoyl)、リノレオイル(linoleoyl)、リノレノイル(linolenoyl)、ステアロイル(stearoyl)、ミリストイル(myristoyl)、アラキドノイル(arachidonoyl)で構成される群から選択されることを特徴とする請求項1に記載の組成物。
- 前記R1およびR2の組み合わせ(R1/R2)は、オレオイル/パルミトイル、パルミトイル/オレオイル、パルミトイル/リノレオイル、パルミトイル/リノレノイル、パルミトイル/アラキドノイル、パルミトイル/ステアロイル、パルミトイル/パルミトイル、オレオイル/ステアロイル、リノレオイル/パルミトイル、リノレオイル/ステアロイル、ステアロイル/リノレオイル、ステアロイル/オレオイル、ミリストイル/リノレオイル、ミリストイル/オレオイルで構成される群から選択されることを特徴とする請求項1に記載の組成物。
- 前記モノアセチルジアシルグリセロール化合物は、下記の化学式2で表示される化合物であることを特徴とする請求項1に記載の組成物。
[化学式2]
- 前記モノアセチルジアシルグリセロール化合物は鹿茸から分離したことを特徴とする請求項1に記載の組成物。
- 前記モノアセチルジアシルグリセロール化合物はIL-4の分泌を減少させることを特徴とする請求項1に記載の組成物。
- 前記モノアセチルジアシルグリセロール化合物はIgEの分泌を減少させることを特徴とする請求項1に記載の組成物。
- 前記組成物は、化学式1で表示されるモノアセチルジアシルグリセロール化合物を0.001ないし50重量%含むことを特徴とする、請求項1に記載の組成物。
[化学式1]
上記の式において、R1およびR2はそれぞれ炭素数14ないし20の脂肪酸基である。 - 下記の化学式1で表示されるモノアセチルジアシルグリセロール化合物を有効性分として含有することを特徴とする、アトピー皮膚炎の予防または改善用健康機能食品組成物。
[化学式1]
上記の式において、R1およびR2はそれぞれ炭素数14ないし20の脂肪酸基である。 - 下記の化学式1で表示されるモノアセチルジアシルグリセロール化合物を有効性分として含有することを特徴とする、アトピー皮膚炎の予防または改善用医薬外品組成物。
[化学式1]
上記の式において、R1およびR2はそれぞれ炭素数14ないし20の脂肪酸基である。 - 下記の化学式1で表示されるモノアセチルジアシルグリセロール化合物を有効性分として含有することを特徴とする、アトピー皮膚炎の予防または改善用化粧料組成物。
[化学式1]
上記の式において、R1およびR2はそれぞれ炭素数14ないし20の脂肪酸基である。 - 前記R1およびR2はそれぞれ、パルミトイル(palmitoyl)、オレオイル(oleoyl)、リノレオイル(linoleoyl)、リノレノイル(linolenoyl)、ステアロイル(stearoyl)、ミリストイル(myristoyl)、アラキドノイル(arachidonoyl)で構成される群から選択されることを特徴とする、請求項9ないし11のうちいずれか一項に記載の組成物。
- 前記R1およびR2の組み合わせ(R1/R2)は、オレオイル/パルミトイル、パルミトイル/オレオイル、パルミトイル/リノレオイル、パルミトイル/リノレノイル、パルミトイル/アラキドノイル、パルミトイル/ステアロイル、パルミトイル/パルミトイル、オレオイル/ステアロイル、リノレオイル/パルミトイル、リノレオイル/ステアロイル、ステアロイル/リノレオイル、ステアロイル/オレオイル、ミリストイル/リノレオイル、ミリストイル/オレオイルで構成される群から選択されることを特徴とする、請求項9ないし11のうちいずれか一項に記載の組成物。
- 請求項1ないし8のうちいずれか一項に記載の組成物を非人間個体に投与する段階を含むことを特徴とする、アトピー皮膚炎の予防または治療方法。
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JP2019534325A (ja) * | 2016-10-17 | 2019-11-28 | エンジーケム ライフサイエンシーズ コーポレーションEnzychem Lifesciences Corporation | モノアセチルジアシルグリセロール化合物を含有する乾癬の予防または治療用組成物 |
JP2021169465A (ja) * | 2016-10-17 | 2021-10-28 | エンジーケム ライフサイエンシーズ コーポレーションEnzychem Lifesciences Corporation | モノアセチルジアシルグリセロール化合物を含有する乾癬の予防または治療用組成物 |
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EP3042651A4 (en) | 2017-04-26 |
CA2922171A1 (en) | 2015-03-12 |
RU2016112495A (ru) | 2017-10-09 |
CA2922171C (en) | 2018-07-03 |
EP3042651B1 (en) | 2020-01-01 |
CN105492003A (zh) | 2016-04-13 |
AU2014315877B2 (en) | 2017-03-23 |
JP6129423B2 (ja) | 2017-05-17 |
WO2015034247A1 (ko) | 2015-03-12 |
US20160193174A1 (en) | 2016-07-07 |
AU2014315877A1 (en) | 2016-03-10 |
RU2640503C2 (ru) | 2018-01-09 |
EP3042651A1 (en) | 2016-07-13 |
ES2774969T3 (es) | 2020-07-23 |
KR20150027008A (ko) | 2015-03-11 |
US9763908B2 (en) | 2017-09-19 |
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