PHALLOIDIN
Synonym(s):;Phalloidin, Amanita phalloides - CAS 17466-45-4 - Calbiochem
- CAS NO.:17466-45-4
- Empirical Formula: C35H48N8O11S
- Molecular Weight: 788.87
- MDL number: MFCD06201852
- EINECS: 241-484-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-23 13:36:13
What is PHALLOIDIN?
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.
Chemical properties
white powder
The Uses of PHALLOIDIN
Phalloidin has been used:
- As a supplement in PEM buffer and dimethyl sulfoxide (DMSO).
- As a drug.
- In immunohistochemistry to stain F-actin.
What are the applications of Application
Phalloidin is a heptapeptide phallotoxin and F-actin stabilizing toxin that can prevent the dissociation of paired filaments in the cell.
Definition
ChEBI: A homodetic bicyclic heptapeptide having a sulfide bridge.
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
Properties of PHALLOIDIN
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) |
pka | 13.03±0.70(Predicted) |
form | White crystalline solid |
Boiling point: | 1370.5±65.0 °C(Predicted) |
color | Hexahydrate, needles or crystals from water |
Water Solubility | Soluble to 1 mg/ml in water |
Merck | 13,7273 |
BRN | 4347460 |
Stability: | Stable. Incompatible with strong oxidizing agents. |
Safety information for PHALLOIDIN
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
Precautionary Statement Codes |
P260:Do not breathe dust/fume/gas/mist/vapours/spray. P262:Do not get in eyes, on skin, or on clothing. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. |
Computed Descriptors for PHALLOIDIN
Related products of tetrahydrofuran
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