ChemicalBook--->CAS DataBase List--->17466-45-4

17466-45-4

17466-45-4 Structure

17466-45-4 Structure
IdentificationBack 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 PropertiesBack 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 activity]

+62.3 (Ethanol)
[Water Solubility ]

Soluble to 1 mg/ml in water
[Merck ]

13,7273
[BRN ]

4347460
Hazard InformationBack 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
Safety DataBack 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
[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)
Spectrum DetailBack Directory
[Spectrum Detail]

PHALLOIDIN(17466-45-4)IR1
PHALLOIDIN(17466-45-4)IR2
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