P1951

Sigma-Aldrich

Phalloidin–Tetramethylrhodamine B isothiocyanate

peptide from Amanita phalloides

Synonym(s):
Phalloidin-TRITC
Empirical Formula (Hill Notation):
C62H72N12O12S4
Molecular Weight:
1305.57
MDL number:
NACRES:
NA.32

Quality Level

biological source

peptide from Amanita phalloides

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

Mixed isomers

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3462 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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...
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...
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)
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...
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