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Merck

F4425

Sigma-Aldrich

Fostriecin sodium salt from Streptomyces pulveraceus

≥98% (HPLC)

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About This Item

Fórmula empírica (notación de Hill):
C19H26NaO9P
Número de CAS:
Peso molecular:
452.37
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

biological source

Streptomyces sp. (Streptomyces pulveraceous)

Quality Level

assay

≥98% (HPLC)

form

solid

solubility

ethanol: soluble
methanol: soluble
water: soluble

storage temp.

−20°C

SMILES string

[Na+].C[C@@](O)(\C=C\[C@H]1CC=CC(=O)O1)[C@@H](C[C@@H](O)\C=C/C=C\C=C\CO)OP(O)([O-])=O

InChI

1S/C19H27O9P.Na/c1-19(23,12-11-16-9-7-10-18(22)27-16)17(28-29(24,25)26)14-15(21)8-5-3-2-4-6-13-20;/h2-8,10-12,15-17,20-21,23H,9,13-14H2,1H3,(H2,24,25,26);/q;+1/p-1/b3-2-,6-4+,8-5-,12-11+;/t15-,16+,17+,19+;/m0./s1

InChI key

XBUIKNRVGYFSHL-IAVQPKKASA-M

Application

Fostriecin has been used as a protein phosphatases type 2A (PP2A) inhibitor to study its effects on phosphorylated myosin light chain (pMLC) levels in axon initial segments (AIS). It has also been used as a PP2A inhibitor to study its effects on the regulation of protein kinase Akt (pAKT) by dopamine (DA) in larval zebrafish brain.

Biochem/physiol Actions

Fostriecin is a natural inhibitor of serine/ threonine phosphatases. It is a phosphate monoester produced by fermentation beer of Streptomyces pulveraceus. Fostriecin is a strong inhibitor of protein phosphatases type 2A and 4 (PP2A and PP4) and a weak inhibitor of protein phosphatases type 1 and 5 (PP1 and PP5). It exhibits anti-tumor activity against several tumor cells in vitro and L1210 and P388 leukemias in vivo. The anti-tumor activity of fostriecin is due to its ability to interfere with the reversible phosphorylation of proteins that are involved in the progression of the cell cycle. It also exhibits cytotoxic effects. Fostriecin can inhibit the DNA, RNA and protein synthesis.

Features and Benefits

This compound is featured on the Phosphoprotein Phosphatases (Serine/Threonine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Packaging

Packaged under argon.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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A H Walsh et al.
FEBS letters, 416(3), 230-234 (1997-12-31)
Fostriecin, an antitumor antibiotic produced by Streptomyces pulveraceus, is a strong inhibitor of type 2A (PP2A; IC50 3.2 nM) and a weak inhibitor of type 1 (PP1; IC50 131 microM) serine/threonine protein phosphatases. Fostriecin has no apparent effect on the
Dopamine D2 receptor activity modulates Akt signaling and alters GABAergic neuron development and motor behavior in zebrafish larvae
Souza B R, et al.
The Journal of Neuroscience, 31(14), 5512-5525 (2011)
C J Hastie et al.
FEBS letters, 431(3), 357-361 (1998-08-26)
Protein phosphatase 4 (PP4) is a protein serine/threonine phosphatase that predominantly localises to centrosomes and plays a role in microtubule organisation at centrosomes. Here, PP4 catalytic subunit has been purified from porcine testis to near homogeneity and a specific activity
J B Tunac et al.
The Journal of antibiotics, 36(12), 1595-1600 (1983-12-01)
CI-920 (PD 110,161) and two analogues (PD 113,270 and PD 113,271) are novel antitumor compounds produced by a new actinomycete characterized as Streptomyces pulveraceus subsp. fostreus ATCC 31906. The antitumor compounds are predominantly produced during the stationary (idiophase) growth phase
A Cheng et al.
Cancer research, 58(16), 3611-3619 (1998-08-29)
Fostriecin, a structurally unique phosphate ester, is presently under evaluation in clinical trials to determine its potential use as an antitumor drug in humans. Fostriecin has been reported as having inhibitory activity against DNA topoisomerase type II and protein phosphatases

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