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Merck

F4425

Sigma-Aldrich

Fostriecin sodium salt from Streptomyces pulveraceus

≥98% (HPLC)

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About This Item

Empirische Formel (Hill-System):
C19H26NaO9P
CAS-Nummer:
Molekulargewicht:
452.37
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.77

Biologische Quelle

Streptomyces sp. (Streptomyces pulveraceous)

Qualitätsniveau

Assay

≥98% (HPLC)

Form

solid

Löslichkeit

ethanol: soluble
methanol: soluble
water: soluble

Lagertemp.

−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

InChIKey

XBUIKNRVGYFSHL-IAVQPKKASA-M

Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Verpackung

Packaged under argon.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


Analysenzertifikate (COA)

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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
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)
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

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