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P2141

Sigma-Aldrich

Phalloidin Peptide

≥90% (HPLC), powder

Synonyme(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

Formule empirique (notation de Hill):
C35H48N8O11S
Numéro CAS:
17466-45-4
Poids moléculaire :
788.87
Numéro Beilstein :
4347460
Numéro CE :
241-484-5
Numéro MDL:
MFCD03427567
Code UNSPSC :
12352202
ID de substance PubChem :
24898277
Nomenclature NACRES :
NA.32

product name

Phalloidin from Amanita phalloides, ≥90%

Source biologique

Amanita phalloides

Niveau de qualité

200

Pureté

≥90%

Forme

powder

Chaîne 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

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)

Clé InChI

KPKZJLCSROULON-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300 + H310 + H330

Classification des risques

Acute Tox. 2 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
Correlative light and electron microscopy of the cytoskeleton of cultured cells.
Svitkina TM1and Borisy GG
Methods in Enzymology, 298, 570-592 (1998)
Marjolein B M Meddens et al.
Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada, 19(1), 180-189 (2013-01-26)
Podosomes are cellular adhesion structures involved in matrix degradation and invasion that comprise an actin core and a ring of cytoskeletal adaptor proteins. They are most often identified by staining with phalloidin, which binds F-actin and therefore visualizes the core.
Fluorescent phallotoxin, a tool for the visualization of cellular actin.
Wulf E
Proceedings of the National Academy of Sciences of the USA, 76(9), 4498-4502 (1979)
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