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P5282

Sigma-Aldrich

Phalloidin, Fluorescein Isothiocyanate Labeled

sequence Amanita phalloides(synthetic: peptide sequence)

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Synonym(s):
Phalloidin-FITC
Empirical Formula (Hill Notation):
C56H60N10O15S2
Molecular Weight:
1177.26
MDL number:
NACRES:
NA.32

biological source

sequence from Amanita phalloides (synthetic: peptide sequence)

Quality Level

form

solid

fluorescence

λex 495 nm; λem 520 nm(lit.)

storage temp.

−20°C

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This Item
P1951A9771P2141
form

solid

form

solid

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

fluorescence

λex 495 nm; λem 520 nm(lit.)

fluorescence

λex 540-545 nm; λem 570-573 nm

fluorescence

-

fluorescence

-

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 fluorescently labelled phalloidin compounds can be produced.

Application

Phalloidin, Fluorescein Isothiocyanate Labeled has been used:
  • To visualize F-Actin reorganization in primary neonatal cardiomyocytes (PNCMs) and H9C2 cells (rat cardiac myoblasts) following endothelin-1 (ET-1) and angiotensin II (Ang II) treatment.
  • In immunochemistry to label microfilament.
  • In immunofluorescence analysis to stain F-actin.

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 fluorescently 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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

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


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