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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

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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Pricing

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Emiko Hiraoka et al.
Breast cancer (Tokyo, Japan), 26(5), 581-593 (2019-03-05)
Pseudopodia are actin-rich ventral protrusions associated with cell motility and cancer cell invasion. We previously applied our established method of using excimer laser cell etching to isolate pseudopodial proteins from MDA-MB-231 breast cancer cells. We later identified 14-3-3γ as an
E Langelier et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 48(10), 1307-1320 (2000-09-16)
We investigated the structure of the chondrocyte cytoskeleton in intact tissue sections of mature bovine articular cartilage using confocal fluorescence microscopy complemented by protein extraction and immunoblotting analysis. Actin microfilaments were present inside the cell membrane as a predominantly cortical
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