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(1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール

(1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール 化学構造式
72741-87-8
CAS番号.
72741-87-8
化学名:
(1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール
别名:
スワインソニン;(-)-スワインソニン;(8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール;(1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール;(-)-D-スワインソニン;(1S,2α,8β,8aβ)-オクタヒドロ-1,2,8-インドリジントリオール;D-スワインソニン;スワインソニン (SYNTHETIC)
英語化学名:
SWAINSONINE
英語别名:
8AR)-1;SwainMoia;SWAINSONINE;Tridolgosir;D-Swainsonine;SWAINSONINE 98+%;(-)-D-Swainsonine;Swainsonine min. 99%;swainsonine synthetic;swainsonine from locoweed
CBNumber:
CB0484750
化学式:
C8H15NO3
分子量:
173.21
MOL File:
72741-87-8.mol

(1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール 物理性質

融点 :
148-149°C
沸点 :
353.3±21.0 °C(Predicted)
比重(密度) :
1.38±0.1 g/cm3 (20 ºC 760 Torr)
貯蔵温度 :
2-8°C
溶解性:
H2O: soluble1mg/mL
酸解離定数(Pka):
14.01±0.60(Predicted)
外見 :
lyophilized powder
色:
white to faint yellow
BRN :
4175740
CAS データベース:
72741-87-8

安全性情報

主な危険性  Xn
Rフレーズ  20/21/22
Sフレーズ  36
WGK Germany  3
RTECS 番号 NM2408666
HSコード  29339900

(1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール 価格 もっと(11)

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
富士フイルム和光純薬株式会社(wako) W01W0119-1028 スワインソニン -
Swainsonine -
72741-87-8 1mg ¥30000 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01TOC3208
Swainsonine
72741-87-8 1mg ¥38000 2018-12-26 購入
Sigma-Aldrich Japan S9263 スワインソニン synthetic
Swainsonine synthetic
72741-87-8 .1mg ¥19800 2018-12-25 購入
Sigma-Aldrich Japan S8195 スワインソニン from Metarrhizium anisopliae, ≥98% (TLC)
Swainsonine from Metarrhizium anisopliae, ≥98% (TLC)
72741-87-8 1mg ¥101100 2018-12-25 購入
富士フイルム和光純薬株式会社(wako) W01TRCS885000 スワインソニン (Synthetic)
Swainsonine (Synthetic)
72741-87-8 25mg ¥187500 2018-12-26 購入

(1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール 化学特性,用途語,生産方法

外観

白色~わずかにうすい黄色, 粉末又は塊

溶解性

メタノールに溶ける。

用途

糖たん白質糖鎖合成過程、生物機能の解析ツール。

化学的特性

White Crystalline Solid

天然物の起源

Swainsonia canescens yields this simple alkaloid.

使用

Swainsonine is an indolizidine alkaloid naturally found in certain plants including locoweed that inhibits N-linked glycoside hydrolases, preventing the processing of asparagine-linked glycoproteins. It reversibly inhibits lysosomal α-mannosidase and Golgi α-mannosidase II (IC50 = 0.2 μM). Swainsonine is used to study the role of N-linked glycosylation in cellular processes and has been shown to have antiproliferative and antimetastatic effects of cancer cells in culture and in mice. The inhibition of α-mannosidase activity in lysosomes produces an accumulation of partially-processed oligosaccharides and glycoproteins, giving rise to lysosomal storage disease. Swainsonine toxicity in herbivores results in a condition known as locoism, characterized by hyperactivity, aggression, stiff and clumsy gait, low head carriage, salivation, seizures, and apparent blindness, culminating in increased miscoordination, weakness and death.

使用

Swainsonine is a plant alkaloid derived from Swainsona canescens (a leguminous plant). It is a reversible, active-site directed inhibitor of a-mannosidase at concentrations of 5-10mM. At acid pH, swainsonine resembles an intermediate in the hydrolysis of mannosidases. Swainsonine completely inhibits mammalian Golgi a-mannosidase II (a-3/6-mannosidase in the glycoprotein processing pathway) and mammalian lysosomal a-mannosidase (acid mannosidase). At higher concentrations, swainsonine also inhibits mammalian cytosolic a-mannosidase. It has been shown to inhibit growth of transformed fibroblasts in soft agar and to enhance the antiproliferative effects of INF on murine lymphoreticular tumor cells in vitro. It also blocks the expression of b1-6 branched complex-type oligosaccharides and shunts the pathway towards hybrid-type oligosaccharides. Swainsonine does not appear to inhibit secretion or expression of glycoproteins at the cell surface. Swainsonine is stable for at least 24 h at 37oC in culture media at physiological pH. Working concentration range is 17-1700 ng/ml (0.1-10mM). Swainsonine (at 1 mg/ml) is not cytotoxic and does not inhibit the growth of a variety of mammalian cell lines. Concentrations required to inhibit Golgi a-mannosidase II in vivo may be somewhat higher, as swainsonine tends to concentrate in the acid environment of cell lysosomes, where it exists as a charged cation and does not permeate through membranes readily. Swainsonine blocks the processing of high-mannose oligosaccharides to complex oligosaccharides. Glycoproteins synthesized in the presence of swainsonine tend to carry mostly high-mannose and hybrid oligosaccharide chains. With short treatments (<24 h) with the inhibitor, cells may retain some complex glycoproteins due to asynchronous cell growth and glycoprotein synthesis.

定義

ChEBI: An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.

生物活性

Inhibitor of α -mannosidase II which inhibits glycoprotein processing. Displays anticancer and immune modulatory properties.

(1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール 上流と下流の製品情報

原材料

準備製品


(1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール 生産企業

Global( 99)Suppliers
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Shanghai Fuhe Chemistry Technology Co., Ltd. 0086-21-67651709
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72741-87-8((1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール)キーワード:


  • 72741-87-8
  • SWAINSONINE
  • SWAINSONINE, SWAINSONA CANESCENS
  • 8-indolizinetriol(1s-(1-alpha,2-alpha,8-beta,8a-beta))-octahydro-2
  • 8-indolizinetriol,octahydro-,(1s-(1-alpha,2-alpha,8-beta,8a-beta))-2
  • (-)-SWAINSONINE (1S,2R,8R,8AR)-1,2,8-OCTAHYDROINDOLIZIDINETRIOL (1S,2S,8R,8AR)-TRIHYDROXYINDOLIZIDINE
  • 8α,β-Octahydroindolizidine-1α,2α,8β-triol
  • Swainsonine, Swainsona canescens - CAS 72741-87-8 - Calbiochem
  • 8-indolizinetriol,octahydro-,(1s,2r,8r,8ar)-2
  • (1S,2S,8R,8AR)-TRIHYDROXYINDOLIZIDINE
  • (1S,2R,8R,8AR)-1,2,8-OCTAHYDROINDOLIZIDINETRIOL
  • 8ALPHA,BETA-INDOLIZIDINE-1,2ALPHA,8BETA-TRIOL
  • (1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-Octahydroindolizine-1,2,8-triol
  • Swainsonine min. 99%
  • 8AR)-1
  • 8ALPHA,BETA-INDOLIZIDINE-1ALPHA,2ALPHA,8BETA-TRIOL
  • 8A-BETA-INDOLIZIDINE-1ALPHA,2ALPHA,8BETA-TRIOL
  • 8A,B-INDOLIZIDINE-1,2A,8B-TRIOL
  • 8A,B-OCTAHYDROINDOLIZIDINE-1A,2A,8B-TRIOL
  • swainsonine from locoweed
  • swainsonine from rhizoctonia*leguminicola
  • swainsonine synthetic
  • SWAINSONINE FROM METARRHIZIUM ANISOPLIAE
  • SWAINSONINE FROM RHIZOCTONIA &
  • SWAINSONINE FROM LOCOWEED, 500 UG*
  • SWAINSONINE 98+%
  • Tridolgosir
  • 8a,-Octahydroindolizidine-1a,2a,8-triol
  • (-)-D-Swainsonine
  • (1S,2α,8β,8aβ)-Octahydro-1,2,8-indolizinetriol
  • (1S,8aβ)-Octahydroindolizine-1α,2α,8β-triol
  • スワインソニン
  • (-)-スワインソニン
  • (8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール
  • (1S,8aβ)-オクタヒドロインドリジン-1α,2α,8β-トリオール
  • (-)-D-スワインソニン
  • (1S,2α,8β,8aβ)-オクタヒドロ-1,2,8-インドリジントリオール
  • D-スワインソニン
  • スワインソニン (SYNTHETIC)
  • マンノシダーゼ
  • 酵素阻害剤
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