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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
Beilstein:
4347460
Numéro CE :
241-484-5
Numéro MDL:
MFCD03427567
Code UNSPSC :
12352202
ID de substance PubChem :
24898277
Nomenclature NACRES :
NA.32

Nom du produit

Phalloidin from Amanita phalloides, ≥90%

Source biologique

Amanita phalloides

Niveau de qualité

200

Essai

≥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

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Certificats d'analyse (COA)

Lot/Batch Number
SLCJ8822
SLCJ3767
SLCH8699
SLCG7909
SLCC2334

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Consulter la Bibliothèque de documents

Ilida Ortega et al.
Acta biomaterialia, 9(3), 5511-5520 (2012-11-08)
Corneal stem cell niches are located within the limbus of the eye and are believed to play an important role in corneal regeneration. These niches are often lost in corneal disease or trauma. Our work explores the design of artificial
Julia F Doerner et al.
Nature communications, 3, 990-990 (2012-08-09)
Bacterial mechanosensitive channels are some of the largest pores in nature. In particular, MscL, with a pore diameter >25 Å, allows passage of large organic ions and small proteins. Functional MscL reconstitution into lipids has been proposed for applications in
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)
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
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