Skip to Content
Merck

Skip To

P2141

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View
Pack SizeSKUAvailabilityPrice

About This Item

Empirical Formula (Hill Notation):
C35H48N8O11S
CAS Number:
Molecular Weight:
788.87
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
241-484-5
MDL number:
Beilstein/REAXYS Number:
4347460
Pricing and availability is not currently available.
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist


Product Name

Phalloidin from Amanita phalloides, ≥90%

biological source

Amanita phalloides

Quality Level

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

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.[1] 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.[2]
  • In immunohistochemistry to stain F-actin.[3]

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.[1] 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.

Compare Similar Items

View Full Comparison

Show Differences

1 of 1

This Item
P5282P1951A1304
assay

≥90%

assay

-

assay

-

assay

≥85% (HPLC)

biological source

Amanita phalloides

biological source

sequence from Amanita phalloides (synthetic: peptide sequence)

biological source

sequence from Amanita phalloides (synthetic: peptide sequence)

biological source

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

solid

form

solid

form

powder


pictograms

Skull and crossbones

signalword

Danger

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

Not applicable



Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library



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
Sheng Song et al.
Journal of neuroinflammation, 9, 219-219 (2012-09-20)
Activated microglial cells are an important pathological component in brains of patients with neurodegenerative diseases. The purpose of this study was to investigate the effect of He-Ne (632.8 nm, 64.6 mW/cm2) low-level laser therapy (LLLT), a non-damaging physical therapy, on activated microglia



Global Trade Item Number

SKUGTIN
P2141-1MG04061834362562

Questions

  1. How should this peptide be diluted, and with what? What are the appropriate storage conditions, and how long will it remain stable?

    1 answer
    1. This product is tested for solubility in Methanol at 10 mg/mL. The peptide is also soluble in ethanol, butanol, DMSO, pyridine, and water (at lower rates). Long term solution stability has not been determined, when possible prepare fresh. External sources indicate stock solutions may be stored up to 6 months at -20°C in aliquots and protected from light. Please see the link below for additional information available in the product datasheet:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/394/433/p2141pis-ms.pdf

      Helpful?

Reviews

No rating value

Active Filters