A selective PP2A inhibitor
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Cytostatin (sodium salt)

Item No. 19602

Technical Information
Formal Name
(5S,6S)-5,6-dihydro-6-[(1S,4S,5S,6S,7Z,9Z,11E)-6-hydroxy-1,5-dimethyl-4-(phosphonooxy)-7,9,11-tridecatrien-1-yl]-5-methyl-2H-pyran-2-one, monosodium salt
CAS Number
457070-06-3
Molecular Formula
C21H32O7P • Na
Formula Weight
Purity
≥75%
Formulation
A solid
DMSO: SolubleMethanol: SolubleWater: Soluble
SMILES
O=C1O[C@]([C@@H](C)CC[C@H](OP(O)([O-])=O)[C@@H](C)[C@@H](O)/C=C\C=C/C=C/C)([H])[C@@H](C)C=C1.[Na+]
InChi Code
InChI=1S/C21H33O7P.Na/c1-5-6-7-8-9-10-18(22)17(4)19(28-29(24,25)26)13-11-15(2)21-16(3)12-14-20(23)27-21;/h5-10,12,14-19,21-22H,11,13H2,1-4H3,(H2,24,25,26);/q;+1/p-1/b6-5+,8-7-,10-9-;/t15-,16-,17-,18-,19-,21-;/m0./s1
InChi Key
DXWSCXWALSKXSD-IAPNMYKYSA-M
Origin
Bacterium/Streptomyces sp. MJ654-NF4
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Cytostatin is a natural antitumor inhibitor of cell adhesion to extracellular matrix, blocking adhesion of B16 melanoma cells to laminin and collagen type IV in vitro (IC50s = 1.3 and 1.4 µg/ml, respectively) and B16 cells metastatic activity in mice.1,2 It induces apoptosis of FS3 mouse fibrosarcoma cells (IC50 = 3.1 µg/ml).3 Cytostatin potently and selectively inhibits protein phosphatase 2A (PP2A; IC50 = 29 nM against the catalytic subunit), while having no effect against PP1, PP2B, or PP5.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Amemiya, M., Ueno, M., Osono, M., et alCytostatin, a novel inhibitor of cell adhesion to components of extracellular matrix produced by Streptomyces sp. MJ654-NF4. I. Taxonomy, fermentation, isolation and biological activities. J. Antibiot. (Tokyo) 47(5), 536-540 (1994).

    2. Masuda, T., Watanabe, S.-i., Amemiya, M., et alInhibitory effect of cytostatin on spontaneous lung metastases of B16-BL6 melanoma cells. J. Antibiot. (Tokyo) 48(6), 528-529 (1995).

    3. Yamazaki, K., Amemiya, M., Ishizuka, M., et alScreening for apoptosis inducers in microbial products and induction of apoptosis by cytostatin. J. Antibiot. (Tokyo) 48(10), 1138-1140 (1995).

    4. Kawada, M., Amemiya, M., Ishizuka, M., et alCytostatin, an inhibitor of cell adhesion to extracellular matrix, selectively inhibits protein phosphatase 2A. Biochim. Biophys. Acta 1452(2), 209-217 (1999).

    5. Swingle, M.R., Amable, L., Lawhorn, B.G., et alStructure-activity relationship studies of fostriecin, cytostatin, and key analogs, with PP1, PP2A, PP5, and (β12-β13)-chimeras (PP1/PP2A and PP5/PP2A), provide further insight into the inhibitory actions of fostriecin family inhibitors. J. Pharmacol. Exp. Ther. 331(1), 45-53 (2009).