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P8157

Sigma-Aldrich

Phallacidin from Amanita phalloides

≥85%

Synonym(s):

Cyclo(Ala-2-Mercapto-Trp-4,5-Dihydroxy-Leu-Val-erythro-3-Hydroxy-D-Asp-Cys-cis-4-Hydroxy-Pro)

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About This Item

Empirical Formula (Hill Notation):
C37H50N8O13S
CAS Number:
26645-35-2
Molecular Weight:
846.90
MDL number:
MFCD00063359
UNSPSC Code:
12352202
PubChem Substance ID:
24898913
NACRES:
NA.56

biological source

Amanita phalloides

Assay

≥85%

form

powder

SMILES string

CC(C)C1NC(=O)C(CC(C)(O)CO)NC(=O)C2Cc3c(SCC(NC(=O)C(NC1=O)C(O)C(O)=O)C(=O)N4CC(O)CC4C(=O)NC(C)C(=O)N2)[nH]c5ccccc35

InChI

1S/C37H50N8O13S/c1-15(2)25-32(53)44-26(27(48)36(56)57)33(54)41-23-13-59-34-19(18-7-5-6-8-20(18)42-34)10-21(29(50)40-22(30(51)43-25)11-37(4,58)14-46)39-28(49)16(3)38-31(52)24-9-17(47)12-45(24)35(23)55/h5-8,15-17,21-27,42,46-48,58H,9-14H2,1-4H3,(H,38,52)(H,39,49)(H,40,50)(H,41,54)(H,43,51)(H,44,53)(H,56,57)

InChI key

KUBDTFZQCYLLGC-UHFFFAOYSA-N

Biochem/physiol Actions

Phallacidin, which is a bicyclic toxin from the Amanita phalloides mushroom, has been shown to inhibit F-actin degradation by proteolytic enzymes including trypsin and α-chymotrypsin.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Rachel E Laudadio et al.
American journal of physiology. Cell physiology, 289(6), C1388-C1395 (2005-08-27)
Although changes of cytoskeleton (CSK) stiffness and friction can be induced by diverse interventions, all mechanical changes reported to date can be scaled onto master relationships that appear to be universal. To assess the limits of the applicability of those
K M Rao et al.
Journal of gerontology, 47(2), B37-B44 (1992-03-01)
We studied a number of parameters, which may all depend upon cytoskeletal function, comparing lymphocytes and granulocytes (PMN) from young and old healthy donors. F-actin content was measured by NBD-phallacidin staining, followed by flow cytometry and was expressed as mean
M S Paller
The American journal of physiology, 264(1 Pt 1), C201-C208 (1993-01-01)
The effects of hypoxia and reoxygenation on the lateral mobility of membrane lipids were studied in primary cultures of rat proximal tubule epithelial cells at a subconfluent stage. The lipid lateral diffusion coefficient (DL) of the fluorescent probe 1-acyl-2-(N-4-nitrobenzo-2-oxa-1,3-diazol)-aminocaproyl phosphatidylethanolamine
J de Vries et al.
Biochemistry, 17(10), 1965-1968 (1978-05-16)
The rate of proteolytic degradation of rabbit skeletal muscle actin by trypsin, alpha-chymotrypsin, and, mainly, subtilisin was followed by dual wavelength spectroscopy at 285 nm by reference at 320 nm. Phalloidin and phallacidin, two toxic bicyclic heptapeptides from the mushroom
W Y Chen et al.
International archives of allergy and immunology, 110(4), 325-331 (1996-08-01)
The traditional methods of measuring F-actin content in neutrophils required a large blood sample and a series of isolation procedures. To reduce the disturbing effect on neutrophils, a new method was designed to measure the neutrophil F-actin content directly in
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