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Merck
CN

F4425

Fostriecin sodium salt from Streptomyces pulveraceus

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C19H26NaO9P
CAS Number:
87860-39-7
Molecular Weight:
452.37
NACRES:
NA.77
PubChem Substance ID:
24894863
UNSPSC Code:
12352200
MDL number:
MFCD09971059

Key Documents

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Product Name

Fostriecin sodium salt from Streptomyces pulveraceus, ≥98% (HPLC)

InChI key

XBUIKNRVGYFSHL-IAVQPKKASA-M

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

biological source

Streptomyces sp. (Streptomyces pulveraceous)

assay

≥98% (HPLC)

form

solid

solubility

ethanol: soluble
methanol: soluble
water: soluble

storage temp.

−20°C

Quality Level

100

Related Categories

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT8712
MKCQ3919
MKCB4119
MKBZ0416V
MKBW2838V

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Fostriecin, an antitumor antibiotic with inhibitory activity against serine/threonine protein phosphatases types 1 (PP1) and 2A (PP2A), is highly selective for PP2A
Walsh A, et al.
Febs Letters, 416(3), 230-234 (1997)
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
S S Stampwala et al.
The Journal of antibiotics, 36(12), 1601-1605 (1983-12-01)
A complex of structurally related compounds that exhibit in vivo antileukemic activity was isolated from fermentation broths of a new streptomycete. The components of this complex are water soluble phosphate esters containing a conjugated triene system. The isolation and characterization
Structure-activity relationship studies of fostriecin, cytostatin, and key analogs, with PP1, PP2A, PP5, and (beta12-beta13)-chimeras (PP1/PP2A and PP5/PP2A), provide further insight into the inhibitory actions of fostriecin family inhibitors
Swingle M R, et al.
Journal of Pharmacology and Experimental Therapeutics, 331(1), 45-53 (2009)
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
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