(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン

(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン 化学構造式
76958-67-3
CAS番号.
76958-67-3
化学名:
(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン
别名:
ヒポテミシン;ヒポテマイシン;(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン;(1aR,3S,4S,6Z,9S,15bR)-1a,2,4,5,11,8,9,15b-オクタヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11-ジオン;(2R,4R,6S,7S,9Z,12S)-6,7,16-トリヒドロキシ-18-メトキシ-12-メチル-3,13-ジオキサトリシクロ[13.4.0.02,4]ノナデカ-1(19),9,15,17-テトラエン-8,14-ジオン
英語名:
HYPOTHEMYCIN
英語别名:
f 152 D2;Nsc354462;Hypothemicin;HYPOTHEMYCIN;Hypothemycin - CAS 76958-67-3 - Calbiochem;(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-Tetrahydro-3,4,12-trihydroxy-14-methoxy-9-methyl-3H-oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione;(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-Tetrahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione;(1aR,3S,4S,6Z,9S,15bR)-1a,2,4,5,11,8,9,15b-Octahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11-dione;3H-Oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione,1a,8,9,15b-tetrahydro-3,4,12-trihydroxy-14-methoxy-9-methyl-,(1aR,3S,4S,6Z,9S,15bR)-
CBNumber:
CB3229169
化学式:
C19H22O8
分子量:
378.37
MOL File:
76958-67-3.mol
MSDS File:
SDS

(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン 物理性質

融点 :
170-172℃
貯蔵温度 :
-20°C
溶解性:
DMSO:可溶
外見 :
凍結乾燥固体
色:
白い
安定性::
-20°C の DMSO 溶液で最大 3 か月間保存できます。
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn
Rフレーズ  22
WGK Germany  3
HSコード  29419000
絵表示(GHS) GHS hazard pictograms
注意喚起語 警告
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H302 飲み込むと有害 急性毒性、経口 4 警告 GHS hazard pictograms P264, P270, P301+P312, P330, P501
注意書き

(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン 価格 もっと(3)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
Sigma-Aldrich Japan H1667 ヒポテマイシン from Hypomyces trichothecoides, ≥98% (HPLC)
Hypothemycin from Hypomyces trichothecoides, ≥98% (HPLC)
76958-67-3 250μg ¥27500 2024-03-01 購入
Sigma-Aldrich Japan H1667 ヒポテマイシン from Hypomyces trichothecoides, ≥98% (HPLC)
Hypothemycin from Hypomyces trichothecoides, ≥98% (HPLC)
76958-67-3 1mg ¥100000 2024-03-01 購入
Sigma-Aldrich Japan H1667 ヒポテマイシン from Hypomyces trichothecoides, ≥98% (HPLC)
Hypothemycin from Hypomyces trichothecoides, ≥98% (HPLC)
76958-67-3 250ug ¥41700 2018-12-25 購入

(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン 化学特性,用途語,生産方法

使用

Hypothemycin is a potent and selective inhibitor of threonine/tyrosine-specific kinase, MEK, and other protein kinases that contain a conserved cysteine residue in the ATP-binding site in in vitro studies.

一般的な説明

A cell-permeable cis-enone resorlic acid lactone (RAL) and (5Z)-7-Oxozeaenol (Cat. No. 499610) analog that inhibits several kinases via an initial affinity binding to the ATP pocket, followed by a covalent adduct formation with a conserved ATP site cysteine residue of the targeted enzymes, including, but not limited to, Flt1/VEGFR-1, Flt3, cKit(D816V), MAPK1, MAPK2, MEK1, MKK6, PKCμ, PKD2, PRAK, and Tak1 (≥90% inhibition at 2 μM). Hypothemycin is also reported to inhibit two non-RAL targets (99% and 82% inhibition of TrkA and TrkB, respectively, at 2 μM), while one of the 46 putative cis-enone RALs targets, namely GSK-3α, is shown not to be affected. Hypothemycin inhibits multiple kinases involved in MAP kinase pathways and is therefore particularly effective in inhibiting BRAF(V600E)-dependent tumor growth. (5Z)-Zeaenol (Cat. No. 499609) may serve as a negative control.

Biochem/physiol Actions

Hypothemycin, one of the highly oxygenated analogues in the group of 14-membered resorcylic acid lactones (RAL), has minor antifungal and cytotoxic activity and exhibits an in vitro anti-malarial activity with an IC50 of 2.2 μg/mL. Hypothemycin is also reported to selectively and irreversibly inhibit protein kinases that contain a conserved cysteine residue (Cys166) that is located within the ATP-binding domain. Though this group accounts for less then 10% of all identified kinases, there are several targets implicated in aberrant cellular proliferation such as ERKs, MEK, FMS-like tyrosine kinase protein (FLT), and platelet-derived growth factor receptors (PDGFR). In cell culture, hypothemycin displays potent cytotoxicity against cancer cell lines that are dependent on certain activating kinase mutations. Additionally, hypothemycin demonstrates significant tumor growth inhibition in at least three separate murine xenograft models. Hypothemycin also inhibits the production of several cytokines such as IL2, IL6, IFNγ, and TNFα.

(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン 上流と下流の製品情報

原材料

準備製品


(1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン 生産企業

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76958-67-3((1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン)キーワード:


  • 76958-67-3
  • HYPOTHEMYCIN
  • (1aR,3S,4S,6Z,9S,15bR)-1a,2,4,5,11,8,9,15b-Octahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11-dione
  • (1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-Tetrahydro-3,4,12-trihydroxy-9-methyl-14-methoxy-3H-oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione
  • Hypothemicin
  • Nsc354462
  • 3H-Oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione,1a,8,9,15b-tetrahydro-3,4,12-trihydroxy-14-methoxy-9-methyl-,(1aR,3S,4S,6Z,9S,15bR)-
  • (1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-Tetrahydro-3,4,12-trihydroxy-14-methoxy-9-methyl-3H-oxireno[k][2]benzoxacyclotetradecin-5,11(2H,4H)-dione
  • f 152 D2
  • Hypothemycin - CAS 76958-67-3 - Calbiochem
  • ヒポテミシン
  • ヒポテマイシン
  • (1aR,3S,4S,6Z,9S,15bR)-1a,8,9,15b-テトラヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11(2H,4H)-ジオン
  • (1aR,3S,4S,6Z,9S,15bR)-1a,2,4,5,11,8,9,15b-オクタヒドロ-3,4,12-トリヒドロキシ-9-メチル-14-メトキシ-3H-オキシレノ[k][2]ベンゾオキサシクロテトラデシン-5,11-ジオン
  • (2R,4R,6S,7S,9Z,12S)-6,7,16-トリヒドロキシ-18-メトキシ-12-メチル-3,13-ジオキサトリシクロ[13.4.0.02,4]ノナデカ-1(19),9,15,17-テトラエン-8,14-ジオン
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