| Identification | Back Directory | [Name]
PHALLOIDIN | [CAS]
17466-45-4 | [Synonyms]
Nsc523214
PHALLOIDIN
phalloidine
PHALLOIDIN, AMANITA PHALLOIDES
PHALLOIDIN FROM AMANITA PHALLOIDES
pto-l-tryptophyl-4,5-dihydroxy-l-leucyl),cyclic(3,6)-sulfide
Cyclo(L-Ala-D-Thr-L-Cys(1)-L-c4Hyp-L-Ala-L-Trp2(1)-4,5'-dihydroxy-L-Leu-)
cyclic(l-alanyl-d-threonyl-l-cysteinyl-cis-4-hydroxy-l-prolyl-l-alanyl-2-merca
Cyclic(L-alanyl-D-threonyl-L-cysteinyl-cis-4-hydroxy-L-prolyl-L-alanyl-2-mercapto-L-tryptophyl-4,5-dihydroxy-L-leucyl), cyclic (3.fwdarw.6)-sulfide | [EINECS(EC#)]
241-484-5 | [Molecular Formula]
C35H48N8O11S | [MDL Number]
MFCD03427567 | [MOL File]
17466-45-4.mol | [Molecular Weight]
788.87 |
| Chemical Properties | Back Directory | [Appearance]
white powder | [Melting point ]
280-282° | [alpha ]
+55.7°(D/20℃)(c=0.5,メタノール) | [density ]
1.1612 (rough estimate) | [refractive index ]
1.7400 (estimate) | [storage temp. ]
+2C to +8C | [solubility ]
DMF: 10 mg/ml; DMSO: 10 mg/ml; Ethanol: 10 mg/ml; Water: 0.5 mg/ml (warm) | [Boiling point ]
1370.5±65.0 °C(Predicted) | [form ]
White crystalline solid | [pka]
13.03±0.70(Predicted) | [color ]
Hexahydrate, needles or crystals from water | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [biological source]
Amanita phalloides | [Optical Rotation]
+62.3 (Ethanol) | [Water Solubility ]
Soluble to 1 mg/ml in water | [Merck ]
13,7273 | [BRN ]
4347460 | [Sequence]
Ala-{d-Thr}-Cys-{Hyp}-Ala-Trp-Leu (Sulfide bridge: Cys3-Trp6) | [InChIKey]
KPKZJLCSROULON-UHFFFAOYSA-N | [SMILES]
CC(O)C1NC(=O)C(C)NC(=O)C(CC(C)(O)CO)NC(=O)C2Cc3c(SCC(NC1=O)C(=O)N4CC(O)CC4C(=O)NC(C)C(=O)N2)[nH]c5ccccc35 |
| Hazard Information | Back Directory | [Chemical Properties]
white powder | [Definition]
ChEBI: A homodetic bicyclic heptapeptide having a sulfide bridge. | [Description]
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. | [Uses]
Phalloidin has been used:
- As a supplement in PEM buffer and dimethyl sulfoxide (DMSO).
- As a drug.
- In immunohistochemistry to stain F-actin.
| [General Description]
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. | [Biochem/physiol Actions]
Toxin that binds polymeric F actin, stabilizing it and interfering with the function of actin-rich structures. | [Safety Profile]
Poison by ingestion, intraperitoneal, and intravenous routes. Mutation data reported. Whenheated to decomposition it emits toxic fumes of SOx, and NOx. | [Enzyme inhibitor]
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). | [storage]
Store at -20°C | [References]
[1] E WULF. Fluorescent phallotoxin, a tool for the visualization of cellular actin.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1979, 76 9: 4498-4502. DOI: 10.1073/pnas.76.9.4498
[2] MUHAMMAD RAIHAN JUMAT. Imaging analysis of human metapneumovirus-infected cells provides evidence for the involvement of F-actin and the raft-lipid microdomains in virus morphogenesis.[J]. Virology Journal, 2014, 11: 198. DOI: 10.1186/s12985-014-0198-8 |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
26/27/28 | [Safety Statements ]
22-28-36/37-45 | [RIDADR ]
UN 3462 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
SE9800000
| [F ]
18 | [HazardClass ]
6.1(a) | [PackingGroup ]
I | [HS Code ]
2934999090 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 2 Oral | [Hazardous Substances Data]
17466-45-4(Hazardous Substances Data) | [Toxicity]
LD50 i.m. in albino mice: 3.3 mg/g (Vogt); LD50 i.p. in mice: 2 mg/kg (Wieland, Wieland) |
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