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P5282

Sigma-Aldrich

Phalloidin Peptide

≥90% (HPLC), solid, FITC labeled

Synonym(s):

Phalloidin-FITC

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About This Item

Empirical Formula (Hill Notation):
C56H60N10O15S2
Molecular Weight:
1177.26
MDL number:
UNSPSC Code:
12352202
NACRES:
NA.32

product name

Phalloidin, Fluorescein Isothiocyanate Labeled, sequence Amanita phalloides(synthetic: peptide sequence)

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

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

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


Certificates of Analysis (COA)

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Non-muscle myosin heavy chain as a possible target for protein encoded by metastasis-related mts-1 gene.
Kriajevska MV
The Journal of Biological Chemistry, 19679-82, 269(31)-269(31) (1994)
The culture of fibroblasts from diaphragm of giant panda.
Han ZM
In Vitro Cellular & Developmental Biology. Animal, 37(10), 644-645 (2001)
Ting Xu et al.
Journal of leukocyte biology, 84(4), 1192-1201 (2008-07-26)
Recruitment of leukocytes onto inflamed tissues is an important physiological event, in which L-selectin plays an essential role in initial leukocyte capture and at the same time, triggers cell signaling. Lck is a member of the Src family of protein
Fluorescent phallotoxin, a tool for the visualization of cellular actin.
Wulf E
Proceedings of the National Academy of Sciences of the USA, 76(9), 4498-4502 (1979)
The H9C2 cell line and primary neonatal cardiomyocyte cells show similar hypertrophic responses in vitro.
Watkins SJ
In Vitro Cellular & Developmental Biology. Animal, 47(2), 125-131 (2011)

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