phalloidin

Also known as Phalloidine, cyclic(L-alanyl-D-threonyl-L-cysteinyl-cis-4-hydroxy-L-prolyl-L-alanyl-2-mercapto-L-tryptophyl-4,5-dihydroxy-L-leucyl), cyclic (3,6)-sulfide

Phalloidin belongs to a class of toxins called phallotoxins, which are found in mushrooms of the genus Amanita. It is a rigid bicyclic heptapeptide that is lethal after a few days when injected into the bloodstream. The major symptom of phalloidin poisoning is acute hunger due to the destruction of liver cells. It functions by binding and stabilizing filamentous actin (F-actin) and effectively prevents the depolymerization of actin fibers. Due to its tight and selective binding to F-actin, derivatives of phalloidin containing fluorescent tags are used widely in microscopy to visualize F-actin

Chemical data

Formula: C35H48N8O11S
Molecular weight: 788.9 g/mol
IUPAC name: (1S,14R,18S,20S,23S,28S,31S,34R)-28-[(2R)-2,3-dihydroxy-2-methylpropyl]-18-hydroxy-34-[(1S)-1-hydroxyethyl]-23,31-dimethyl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraene-15,21,24,26,29,32,35-heptone
SMILES: C[C@H]1C(=O)N[C@H]2CC3=C(NC4=CC=CC=C34)SC[C@@H](C(=O)N5C[C@H](C[C@H]5C(=O)N1)O)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC2=O)C[C@](C)(CO)O)C)[C@H](C)O
InChIKey: KPKZJLCSROULON-QKGLWVMZSA-N
XLogP: -1.7
Polar surface area: 317 Å²
H-bond donors: 11
H-bond acceptors: 12
Formal charge: 0

via PubChem

Research

5,174 papers

Phalloidin-PAINT: Enhanced quantitative nanoscale imaging of F-actin.Biophysical journal · 2024
Phalloidin Staining for F-Actin in Hepatic Stellate Cells.Methods in molecular biology (Clifton, N.J.) · 2023
Toxicokinetics and tissue distribution of phalloidin in mice.Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association · 2023
Phalloidin and DNase I-bound F-actin pointed end structures reveal principles of filament stabilization and disassembly.Nature communications · 2024
Effects of cytochalasin and phalloidin on actin.The Journal of cell biology · 1987

via PubMed

Wikidata facts

Mass: 788.316325

Show 4 more facts

chemical formula: C₃₅H₄₈N₈O₁₁S
canonical SMILES: CC1C(=O)NC2CC3=C(NC4=CC=CC=C34)SCC(C(=O)N5CC(CC5C(=O)N1)O)NC(=O)C(NC(=O)C(NC(=O)C(NC2=O)CC(C)(CO)O)C)C(C)O
isomeric SMILES: C[C@H]1C(=O)N[C@H]2CC3=C(NC4=CC=CC=C34)SC[C@@H](C(=O)N5C[C@H](C[C@H]5C(=O)N1)O)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC2=O)C[C@](C)(CO)O)C)[C@H](C)O
Commons category: Phalloidin

Sources (3)

via Wikidata · CC0

~9 min read

Article

10 sections

Contents

Discovery and background
Synthesis
Biosynthesis
Chemical synthesis
Mechanism of action
Symptoms
Use as an imaging tool
Uses and limitations
See also
References

==Discovery and background== Phalloidin was one of the first cyclic peptides to be discovered. It was isolated from the death cap mushroom and crystallized by Feodor Lynen and Ulrich Wieland in 1937. Its structure is unusual in that it contains a cysteine-tryptophan linkage to form a bicyclic heptapeptide. This linkage had not been characterized before and makes the structure elucidation of phalloidin significantly more difficult. They determined the presence of the sulfur atom using UV spectroscopy and found that this ring structure had a slightly shifted wavelength. Raney nickel experiments confirmed the presence of sulfur in the tryptophan ring. The researchers found the desulfurized phalloidin was still circular, which demonstrated that the structure of phalloidin is normally bicyclic. Once linearized, the amino acid sequence of de-sulfurized phalloidin was elucidated through Edman degradation by Wieland and Schön in 1955.