ファロイジン 化学特性,用途語,生産方法
外観
白色～ほとんど白色, 結晶～結晶性粉末
溶解性
ブタノールに可溶。エタノールに溶け、水に溶けにくい。メタノール,エタノール,ピリジンに可溶、冷水に難溶。
解説
C35H48N8O11S(788.87)．タマゴテングタケAmanita phalloides，シロテングタケA.vernaに含まれる毒性の環状ヘプタペプチド．ファロイジン, 六水和物は融点280～282 ℃．[α]20D＋55.7°(メタノール)．アルコール類，ピリジンに可溶，水，ほかの有機溶媒に難溶．LD50 2 mg/kg(マウス，腹腔内)．
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森北出版「化学辞典（第2版）
用途
in vitroでのアクチンの研究。
生理作用
ファロイジン, 細胞骨格であるミクロフィラメントのアクチンと結合してその脱重合を阻害し，おもに肝臓に強い病変を起こす．LD50 2 mg/kg(マウス，腹腔内)．
説明
Phalloidin is a natural mycotoxin first isolated from the death cap mushroom,
A. phalloides. It binds F-actin and stabilizes actin fibers. Fluorescently labeled phalloidin is commonly used to stain F-actin in cells.
化学的特性
white powder
使用
Phalloidin has been used:
- As a supplement in PEM buffer and dimethyl sulfoxide (DMSO).
- As a drug.
- In immunohistochemistry to stain F-actin.
定義
ChEBI: A homodetic bicyclic heptapeptide having a sulfide bridge.
一般的な説明
Phalloidin is a phallotoxin produced by death cap mushroom
Amanita phalloides. It is a cyclic peptide, which interacts with actin, and this was first identified in phalloidin-poisoned rats. It is a heptapeptide, cyclic in nature, with a crosslink between tryptophan at position 6 and cysteine at position 3. The side chain of amino acid 7 (γ-δ-dihydroxyleucine) in phalloidin, is accessible to modifications, through which fluorescently labeled phalloidin compounds can be produced.
安全性プロファイル
Poison by ingestion, intraperitoneal, and intravenous routes. Mutation data reported. Whenheated to decomposition it emits toxic fumes of SOx, and NOx.
酵素阻害剤
This bicyclic heptapeptide toxin (FW = 788.88 g/mol; CAS 17466-45-4) is was first isolated from the poisonous green fungus Amanita phalloides. Primary Mode of Action: Phalloidin binds preferentially to filamentous actin; little or no binding to globular actin has been detected. such preferential action stimulates actin polymerization, and phalloidin lowers the actin monomer critical concentration by 30x, from 50-100 nM down to 2-3 nM. When present at 1 to 10 concentration ratio of phalloidin to total actin subunits, actin filaments are also greatly stabilized toward depolymerization. Effects on Actin Filaments: Cellular processes requiring filament disassembly are likewise inhibited. Depolymerization of F-actin by cytochalasins, potassium iodide, and elevated temperatures are inhibited by phalloidin binding. Because the toxin and its fluorescent derivatives are relatively small, a wide variety of actin-binding proteins can still bind to phalloidin-labeled filamentts. Perhaps more significantly, phalloidin-labeled actin filaments retain many of their functional properties, such that phalloidin-labeled, glycerinated muscle fibers can still contract, and labeled actin filaments still move on myosin that has been tethered to solid-phase substrates. Phalloidin can be also be used to assess the relativeconcentrations of these two forms of actin as well as a means to label actin filaments in a cell (See Phallacidin).
概要
タマゴテングタケ (Amanita phalloides) に含まれる毒ペプチド．キノコ100 g (乾燥約5 g) 中に約10 mg含まれる．LD50 (マウス腹腔内) 2 mg kg-1
ファロイジン 上流と下流の製品情報
原材料
準備製品