Skip to Content
MilliporeSigma
All Photos(2)

Documents

P1951

Sigma-Aldrich

Phalloidin–Tetramethylrhodamine B isothiocyanate

sequence from Amanita phalloides(synthetic: peptide sequence)

Synonym(s):

Phalloidin-TRITC

Sign Into View Organizational & Contract Pricing


About This Item

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

biological source

sequence from Amanita phalloides (synthetic: peptide sequence)

Quality Level

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

related product

Product No.
Description
Pricing

pictograms

Skull and crossbones

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)

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’.

Already Own This Product?

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

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Sigma-Aldrich

Sigma-Aldrich

18846

Phalloidin–Atto 655

Elena Maria Boggio et al.
Molecular neurobiology, 56(9), 5987-5997 (2019-02-02)
Perineuronal nets (PNNs) are condensed structures in the extracellular matrix that mainly surround GABA-ergic parvalbumin-positive interneurons in the adult brain. Previous studies revealed a parallel between PNN formation and the closure of the critical period. Moreover, ocular dominance plasticity is
Joan Röhl et al.
Traffic (Copenhagen, Denmark), 20(9), 661-673 (2019-07-13)
Macrophage migration into injured or infected tissue is a key aspect in the pathophysiology of many diseases where inflammation is a driving factor. Membrane-type-1 matrix metalloproteinase (MT1-MMP) cleaves extracellular matrix components to facilitate invasion. Here we show that, unlike the
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 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
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)

Related Content

Three-dimensional (3D) printing of biological tissue is rapidly becoming an integral part of tissue engineering.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service