JP7395637B2 - ヒアルロニダーゼ阻害剤 - Google Patents
ヒアルロニダーゼ阻害剤 Download PDFInfo
- Publication number
- JP7395637B2 JP7395637B2 JP2022052324A JP2022052324A JP7395637B2 JP 7395637 B2 JP7395637 B2 JP 7395637B2 JP 2022052324 A JP2022052324 A JP 2022052324A JP 2022052324 A JP2022052324 A JP 2022052324A JP 7395637 B2 JP7395637 B2 JP 7395637B2
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- JP
- Japan
- Prior art keywords
- salvia
- hyaluronidase
- formula
- present
- tanshinone
- 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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- 229940122393 Hyaluronidase inhibitor Drugs 0.000 title claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 33
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- AZEZEAABTDXEHR-UHFFFAOYSA-M sodium;1,6,6-trimethyl-10,11-dioxo-8,9-dihydro-7h-naphtho[1,2-g][1]benzofuran-2-sulfonate Chemical compound [Na+].C12=CC=C(C(CCC3)(C)C)C3=C2C(=O)C(=O)C2=C1OC(S([O-])(=O)=O)=C2C AZEZEAABTDXEHR-UHFFFAOYSA-M 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 17
- HYXITZLLTYIPOF-UHFFFAOYSA-N Tanshinone II Natural products O=C1C(=O)C2=C3CCCC(C)(C)C3=CC=C2C2=C1C(C)=CO2 HYXITZLLTYIPOF-UHFFFAOYSA-N 0.000 claims description 14
- HARGZZNYNSYSGJ-UHFFFAOYSA-N 1,2 dihydrotanshinquinone Natural products C1=CC2=C(C)C=CC=C2C(C(=O)C2=O)=C1C1=C2C(C)CO1 HARGZZNYNSYSGJ-UHFFFAOYSA-N 0.000 claims description 13
- HARGZZNYNSYSGJ-JTQLQIEISA-N Dihydrotanshinone I Chemical compound C1=CC2=C(C)C=CC=C2C(C(=O)C2=O)=C1C1=C2[C@@H](C)CO1 HARGZZNYNSYSGJ-JTQLQIEISA-N 0.000 claims description 13
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- 231100000111 LD50 Toxicity 0.000 description 4
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Description
(1)下記式(I)で表される化合物及びその薬理学的に許容される塩から選ばれる1つ以上の化合物を有効成分として含有するヒアルロニダーゼ阻害剤を提供するものである。
(2)前記式(I)で表される化合物及びその薬理学的に許容される塩が、タンシノンIIA、クリプトタンシノン、タンシノンI、ジヒドロタンシノンI、タンシノンIIAスルホン酸ナトリウムから選ばれる少なくとも1つ以上である上記(1)に記載のヒアルロニダーゼ阻害剤。
(3)タンジン(Salvia miltiorrhiza)、サルビア・ブレヤナ(Salvia bulleyana)、サルビア・カンパヌラタ(Salvia campanulata)、サルビア・カスタネア(Salvia castanea)、サルビア・ディギタロイデス(Salvia digitaloides)、サルビア・エバンシアナ(Salvia evansiana)、サルビア・フラバ(Salvia flava)、サルビア・マキシモウィッチアーナ(Salvia maximowicziana)、サルビア・オメイアナ(Salvia omeiana)、サルビア・パウキフローラ(Salvia pauciflora)、サルビア・プラッティ(Salvia prattii)、サルビア・プルツェワルスキー(Salvia przewalskii)、サルビア・ロボロフスキー(Salvia roborowskii)、サルビア・ウムブラティカ(Salvia umbratica)、サルビア・ボウレヤナ(Salvia bowleyana)、サルビア・シンプリシフォリア(Salvia simplicifolia)、Salvia dabieshanensis、Salvia meiliensis、サルビア・プリオニティス(Salvia prionitis)、Salvia paramiltiorrhiza、サルビア・プレクトラントイデス(Salvia plectranthoides)、サルビア・ユンナネンシス(Salvia yunnanensis)、Salvia sinica、サルビア・トリジュガ(Salvia trijuga)、Salvia vastaの抽出物から選ばれる1つ以上を有効成分とするヒアルロニダーゼ阻害剤。
(4)(1)~(3)のいずれかに記載のヒアルロニダーゼ阻害剤を含有する、皮膚外用剤。
タンシノンIIA、クリプトタンシノン、ジヒドロタンシノンIは東京化成工業株式会社から、インドメタシン(化学式18)、ロズマリン酸(化学式19)、アラントイン(化学式20)、デキサメタゾン(化学式21)、2-メチル-1,4-ナフトキノン(化学式22)は富士フイルム和光純薬株式会社から、コルチゾン(化学式23)はSigma-Aldrichから、タンシノンIIAスルホン酸ナトリウムはMedChemExpressからそれぞれ購入した。
タンシノンIIA、クリプトタンシノン、ジヒドロタンシノンI、タンシノンIIAスルホン酸ナトリウム、インドメタシン、ロズマリン酸、アラントイン、コルチゾン、デキサメタゾン、2-メチル-1,4-ナフトキノンをそれぞれ5000ppmとなるようにジメチルスルホキシドに溶解し、試料溶液を調製した。さらに、インドメタシンを15000ppm、ロズマリン酸を20000ppmとなるようにジメチルスルホキシドに溶解し、試料溶液を調製した。
乾燥し、刻んだタンジンの根20gに対し、99.5%(v/v)エタノール200mLを加え、23℃で24時間浸漬し抽出した。ろ過後、溶媒を留去し、タンジン抽出物を90mg得た。得られたタンジン抽出物を10000ppmとなるようにジメチルスルホキシドに溶解し、試料溶液を調製した。
ヒアルロニダーゼ活性阻害試験は、未分解のヒアルロン酸が酸性アルブミン溶液中で沈殿する反応を利用して、沈殿ヒアルロン酸量からヒアルロニダーゼ活性阻害を調べる、Molecules 2015, 20, 16723-16740頁に記載された方法を一部改変して行った。具体的には、0.05mg/mLウシ精巣由来ヒアルロニダーゼ(Type I-S、400-1000units/mg、Sigma社製)溶液(77mM塩化ナトリウム及び0.01%ウシ血清アルブミンを含む20mMリン酸ナトリウム緩衝液、pH6.9)90μLに各試料溶液10μLを加え、10分間37℃でプレインキュベートした。この混合溶液に、鶏冠由来の0.4mg/mLヒアルロン酸ナトリウム(和光純薬社製)溶液100μL(300mMリン酸ナトリウム緩衝液、pH5.3)を加え、30分間、37℃でインキュベートした。0.1%ウシ血清アルブミンからなる酸性アルブミン溶液(24mM酢酸ナトリウム、79mM 酢酸、pH3.75)1mLを加え、10分間室温で放置後、マイクロプレートリーダーを用いて波長595nmにおける吸光度を測定した(N=3)。ヒアルロニダーゼ活性阻害率は以下の式を用いて算出した。結果を表1に示す。なお、表中括弧内の濃度は、試料溶液調製時の濃度を表す。
タンシノンIIAスルホン酸ナトリウム 0.05
ポリオキシエチレンソルビタンモノラウレート(20E.O.) 1.5
1,3-ブチレングリコール 4.5
グリセリン 3.0
エタノール 2.0
ヒアルロン酸ナトリウム(1%水溶液) 5.0
エデト酸三ナトリウム 0.1
防腐剤 適量
pH調整剤 適量
精製水 残部
合計 100.0
タンジン抽出物 0.1
ステアリルアルコール 6.0
ステアリン酸 2.0
ワセリン 4.0
スクワラン 9.0
オクチルドデカノール 10.0
1,3-ブチレングリコール 6.0
グリセリン 4.0
POE(20)セチルアルコールエーテル 3.0
モノステアリン酸グリセリン 2.0
酸化防止剤 適量
防腐剤 適量
精製水 残部
合計 100.0
クリプトタンシノン 0.03
タルク 5.0
セリサイト 8.0
酸化チタン 5.0
色顔料 適量
モノイソステアリン酸ポリグリセリル 3.0
ポリオキシエチレン硬化ヒマシ油 1.5
イソノナン酸イソトリデシル 10.0
1,3-ブチレングリコール 5.0
酸化防止剤 適量
防腐剤 適量
精製水 残部
合計 100.0
タンシノンIIA 0.02
ジヒドロタンシノンI 0.02
酸化チタン 10.0
酸化亜鉛 10.0
PEG-9ポリジメチルシロキシエチルジメチコン 1.5
ラウリルPEG9-ポリジメチルシロキシエチルジメチコン 1.5
シクロペンタシロキサン 20.0
ジメチコン 10.0
(ジメチコン/ビニルジメチコン)クロスポリマー 0.5
セチルジメチコン 0.2
グリチルレチン酸エステル 0.0
メチルグルセス-20 1.0
1,3-ブチレングリコール 10.0
塩化ナトリウム 適量
酸化防止剤 適量
防腐剤 適量
精製水 残部
合計 100.0
ジヒドロタンシノンI 0.1
レゾルシン 0.5
パラジメチルアミノ安息香酸オクチル 4.0
ブチルメトキシベンゾイルメタン 4.0
ステアリルアルコール 18.0
モクロウ 20.0
グリセリンモノステアリン酸エステル 0.3
ワセリン 33.0
香料 適量
防腐剤・酸化防止剤 適量
精製水 残部
合計 100.0
タンシノンIIAスルホン酸ナトリウム 5.0
卵殻カルシウム 10.0
乳糖 20.0
澱粉 7.0
デキストリン 8.0
硬化油 5.0
セルロース 残部
合計 100.0
タンシノンIIAスルホン酸ナトリウム 1.0
タウリン 3.0
塩酸塩 0.02
チアミン硫化物 0.01
リボフラビン 0.003
無水カフェイン 0.05
精製白糖 5.0
D-ソルビトール液 2.0
クエン酸無水物 0.2
香料 適量
精製水 残部
合計 100.0
Claims (2)
- 下記式(I)で表される化合物及びその薬理学的に許容される塩から選ばれる1つ以上の化合物を有効成分として含有するヒアルロニダーゼ阻害剤。
- 前記式(I)で表される化合物及びその薬理学的に許容される塩が、タンシノンIIA、クリプトタンシノン、タンシノンI、ジヒドロタンシノンI、タンシノンIIAスルホン酸ナトリウムから選ばれる少なくとも1つ以上である請求項1に記載のヒアルロニダーゼ阻害剤。
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