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Phalloidin from Amanita phalloides

SIGMA/P2141 - ≥90%

Synonym: 28-(2,3-dihydroxy-2-methylpropyl)-18-hydroxy-34-(1-hydroxyethyl)-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraene-15,21,24,26,29,32,35-heptone

CAS Number: 17466-45-4
Empirical Formula (Hill Notation): C35H48N8O11S
Molecular Weight: 788.87
EC Number: 241-484-5
MDL Number: MFCD03427567
Linear Formula: C35H48N8O11S
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-P2141-1MG 1 mg
 $333.00
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assay ≥90%
biological source Amanita phalloides
form powder
InChI 1S/C35H48N8O11S/c1-15-27(47)38-22-10-20-19-7-5-6-8-21(19)41-33(20)55-13-24(34(53)43-12-18(46)9-25(43)31(51)37-15)40-32(52)26(17(3)45)42-28(48)16(2)36-30(50)23(39-29(22)49)11-35(4,54)14-44/h5-8,15-18,22-26,41,44-46,54H,9-14H2,1-4H3,(H,36,50)(H,37,51)(H,38,47)(H,39,49)(H,40,52)(H,42,48)
InChI key KPKZJLCSROULON-UHFFFAOYSA-N
Quality Level 200 
SMILES string 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
Application: Phalloidin has been used:
• As a supplement in PEM buffer and dimethyl sulfoxide (DMSO).
• As a drug.
• In immunohistochemistry to stain F-actin.
Biochem/physiol Actions: Phalloidin interacts with polymeric actin, and not oligomeric or monomeric forms. This interaction leads to highly stabilized actin filaments, which resist depolymerization and disassembly. In rats, this toxin causes death due to liver hemorrhage and cells show abnormal actin clustering. The affinity of phalloidin to actin is not significantly altered after derivatizing fluorescently labelled phalloidin compounds. These compounds can be used to study actin structure and organization within eukaryotic cells.
Biochem/physiol Actions: Phalloidin is a toxin isolated from Amanita phalloides that binds polymeric F actin, stabilizing it and interfering with the function of
actin-rich structures.
Biochem/physiol Actions: Toxin that binds polymeric F actin, stabilizing it and interfering with the function of actin-rich structures.
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.
Purity ≥90%
UNSPSC 12352202

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