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P1951

Sigma-Aldrich

Phalloidin Peptide

≥90% (HPLC), solid, TRITC labeled

Synonym(s):

Phalloidin-TRITC

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About This Item

Empirical Formula (Hill Notation):
C60H70N12O13S2
Molecular Weight:
1231.40
MDL number:
MFCD00278840
UNSPSC Code:
12352116
NACRES:
NA.32

product name

Phalloidin–Tetramethylrhodamine B isothiocyanate, sequence from Amanita phalloides(synthetic: peptide sequence)

biological source

sequence from Amanita phalloides (synthetic: peptide sequence)

Quality Level

200

form

solid

fluorescence

λex 540-545 nm; λem 570-573 nm

storage temp.

−20°C

Related Categories

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 florescent labelled phalloidin compounds can be produced.

Application

Fluorescent phallotoxin which may be used to identify filamentous actin.

Phalloidin-Tetramethylrhodamine B isothiocyanate has been used:-
  • In Immunofluorescence for staining Filamentous actin (F-actin)
  • To stain cells during immunocytochemical and cytochemical analysis
  • To label actin microfilaments for fluorescence microscopy

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 florescent 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.

Other Notes

May contain mixed isomers

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Description
Pricing

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Sigma-Aldrich

Sigma-Aldrich

18846

Phalloidin–Atto 655

Nadav Sorek et al.
Plant physiology, 155(2), 706-720 (2010-12-09)
Prenylation primarily by geranylgeranylation is required for membrane attachment and function of type I Rho of Plants (ROPs) and Gγ proteins, while type II ROPs are attached to the plasma membrane by S-acylation. Yet, it is not known how prenylation
Cristina Belgiovine et al.
PloS one, 5(11), e14154-e14154 (2011-01-07)
Mesenchymal and amoeboid movements are two important mechanisms adopted by cancer cells to invade the surrounding environment. Mesenchymal movement depends on extracellular matrix protease activity, amoeboid movement on the RhoA-dependent kinase ROCK. Cancer cells can switch from one mechanism to
E Wulf et al.
Proceedings of the National Academy of Sciences of the United States of America, 76(9), 4498-4502 (1979-09-01)
A fluorescent derivative of phalloidin has been synthesized possessing high affinity to filamentous actin. This compound was used for visualization of actin-containing structures in eukaryotic nonmuscle cells. Due to its low molecular weight (1250), fixation for formaldehyde was sufficient to
Anna Mas-Vinyals et al.
Colloids and surfaces. B, Biointerfaces, 181, 864-871 (2019-08-07)
Regenerative medicine requires the use of heterogeneous scaffolds when the tissue that needs to be repaired presents a gradient in its properties and cannot be replaced by a homogeneous graft. Then, an intimate contact between the different layers is critical
Fluorescent phallotoxins as probes for filamentous actin.
H Faulstich et al.
Journal of muscle research and cell motility, 9(5), 370-383 (1988-10-01)
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