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MedKoo Cat#: 412998 | Name: Fostriecin (free base)

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fostriecin (free base) is an inhibitor of the serine/threonine protein phosphatases 2A (PP2A) and 4 (PP4) (IC50s = 3.2 and 3 nM, respectively). It less effectively inhibits topoisomerase II and PP1 (IC50s = 40 and 131 μM, respectively) and does not inhibit PP2B. Through its effects on protein phosphatases, fostriecin increases the level of histone H3 phosphorylation and may alter epigenetic regulation of cell proliferation. On a related note, fostriecin was first identified as an antitumor antibiotic.

Chemical Structure

Fostriecin (free base)
Fostriecin (free base)
CAS# 87810-56-8 (free base)

Theoretical Analysis

MedKoo Cat#: 412998

Name: Fostriecin (free base)

CAS#: 87810-56-8 (free base)

Chemical Formula: C19H27O9P

Exact Mass: 430.1393

Molecular Weight: 430.38

Elemental Analysis: C, 53.02; H, 6.32; O, 33.46; P, 7.20

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
87810-56-8 (free base) 87860-39-7 (Na+)
Synonym
Fostriecin (free base); CI920; CI-920; CI 920
IUPAC/Chemical Name
2H-Pyran-2-one, 5,6-dihydro-6-(3,6,13-trihydroxy-3-methyl-4-(phosphonooxy)-1,7,9,11-tridecatetraenyl)-
InChi Key
ZMQRJWIYMXZORG-CVMFKEHVSA-N
InChi Code
InChI=1S/C19H27O9P/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)/b3-2+,6-4+,8-5+,12-11+
SMILES Code
O=C1C=CCC(/C=C/C(C)(O)C(OP(O)(O)=O)CC(O)/C=C/C=C/C=C/CO)O1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 430.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Dong G, Li B, O'Doherty G. Total and Formal Syntheses of Fostriecin. Org Chem Front. 2020 Nov 21;7(22):3608-3615. doi: 10.1039/d0qo01121e. Epub 2020 Oct 12. PMID: 33184589; PMCID: PMC7654735. 2: Lewy DS, Gauss CM, Soenen DR, Boger DL. Fostriecin: chemistry and biology. Curr Med Chem. 2002 Nov;9(22):2005-32. doi: 10.2174/0929867023368809. PMID: 12369868. 3: Gao D, Li B, O'Doherty GA. Synthesis of Dehydro-Dephospho-Fostriecin and Formal Total Synthesis of Fostriecin. Org Lett. 2019 Oct 18;21(20):8334-8338. doi: 10.1021/acs.orglett.9b03120. Epub 2019 Oct 4. PMID: 31584287. 4: Bastan R, Eskandari N, J Ardakani H, T Peachell P. Effects of fostriecin on β2-adrenoceptor-driven responses in human mast cells. J Immunotoxicol. 2017 Dec;14(1):60-65. doi: 10.1080/1547691X.2016.1259277. Epub 2017 Jan 16. PMID: 28090813. 5: Trost BM, Knopf JD, Brindle CS. Synthetic Strategies Employed for the Construction of Fostriecin and Related Natural Products. Chem Rev. 2016 Dec 28;116(24):15035-15088. doi: 10.1021/acs.chemrev.6b00488. Epub 2016 Dec 8. PMID: 28027648; PMCID: PMC5720176. 6: de Jong RS, de Vries EG, Mulder NH. Fostriecin: a review of the preclinical data. Anticancer Drugs. 1997 Jun;8(5):413-8. PMID: 9215602. 7: Cheng A, Balczon R, Zuo Z, Koons JS, Walsh AH, Honkanen RE. Fostriecin- mediated G2-M-phase growth arrest correlates with abnormal centrosome replication, the formation of aberrant mitotic spindles, and the inhibition of serine/threonine protein phosphatase activity. Cancer Res. 1998 Aug 15;58(16):3611-9. PMID: 9721869. 8: Theobald B, Bonness K, Musiyenko A, Andrews JF, Urban G, Huang X, Dean NM, Honkanen RE. Suppression of Ser/Thr phosphatase 4 (PP4C/PPP4C) mimics a novel post-mitotic action of fostriecin, producing mitotic slippage followed by tetraploid cell death. Mol Cancer Res. 2013 Aug;11(8):845-55. doi: 10.1158/1541-7786.MCR-13-0032. Epub 2013 May 13. PMID: 23671329; PMCID: PMC3748177. 9: Weinbrenner C, Baines CP, Liu GS, Armstrong SC, Ganote CE, Walsh AH, Honkanen RE, Cohen MV, Downey JM. Fostriecin, an inhibitor of protein phosphatase 2A, limits myocardial infarct size even when administered after onset of ischemia. Circulation. 1998 Sep 1;98(9):899-905. doi: 10.1161/01.cir.98.9.899. PMID: 9738645. 10: Takeuchi T, Takahashi N, Ishi K, Kusayanagi T, Kuramochi K, Sugawara F. Antitumor antibiotic fostriecin covalently binds to cysteine-269 residue of protein phosphatase 2A catalytic subunit in mammalian cells. Bioorg Med Chem. 2009 Dec 1;17(23):8113-22. doi: 10.1016/j.bmc.2009.09.050. Epub 2009 Oct 3. PMID: 19857968.