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P2141

Phalloidin Peptide

Name: Phalloidin Peptide
Brand: SIGMA

≥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[12.11.11.0^3,11.0^4,9.0^16,20]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

NACRES:

NA.32

PubChem Substance ID:

24898277

UNSPSC Code:

12352202

EC Number:

241-484-5

MDL number:

MFCD03427567

Beilstein/REAXYS Number:

4347460

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Properties

Product Name

Phalloidin from Amanita phalloides, ≥90%

biological source

Amanita phalloides

Quality Segment

200

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

Description

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.

Phalloidin is a toxin isolated from Amanita phalloides that binds polymeric F actin, stabilizing it and interfering with the function of
actin-rich structures.

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

pictograms

GHS06

signalword

Danger

hcodes

H300 + H310 + H330

pcodes

P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

flash_point_f

Not applicable

flash_point_c