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P2141

Sigma-Aldrich

Phalloidin Peptide

≥90% (HPLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C35H48N8O11S
CAS Number:
17466-45-4
Molecular Weight:
788.87
Beilstein:
4347460
EC Number:
241-484-5
MDL number:
MFCD03427567
UNSPSC Code:
12352202
PubChem Substance ID:
24898277
NACRES:
NA.32

product name

Phalloidin from Amanita phalloides, ≥90%

biological source

Amanita phalloides

Assay

≥90%

form

powder

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

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

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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.

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.
Toxin that binds polymeric F actin, stabilizing it and interfering with the function of actin-rich structures.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Thomas Pujol et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(26), 10364-10369 (2012-06-13)
Actin filaments play a fundamental role in cell mechanics: assembled into networks by a large number of partners, they ensure cell integrity, deformability, and migration. Here we focus on the mechanics of the dense branched network found at the leading
Yaqi You et al.
Biomaterials, 269, 120356-120356 (2020-11-16)
Epicardial placement of mesenchymal stromal cells (MSCs) is a promising strategy for cardiac repair post-myocardial infarction, but requires the design of biomaterials to maximise the retention of donor cells on the heart surface and control their phenotype. To this end
Matthias Samwer et al.
The EMBO journal, 32(13), 1886-1902 (2013-06-04)
Nuclei of Xenopus laevis oocytes grow 100 000-fold larger in volume than a typical somatic nucleus and require an unusual intranuclear F-actin scaffold for mechanical stability. We now developed a method for mapping F-actin interactomes and identified a comprehensive set of
Cell-compatible, multicomponent protein arrays with subcellular feature resolution.
Ying Mei et al.
Small (Weinheim an der Bergstrasse, Germany), 4(10), 1600-1604 (2008-10-11)
Correlative light and electron microscopy of the cytoskeleton of cultured cells.
Svitkina TM1and Borisy GG
Methods in Enzymology, 298, 570-592 (1998)
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