Fostriecin
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| Category | Antibiotics |
| Catalog number | BBF-01849 |
| CAS | 87810-56-8 |
| Molecular Weight | 430.39 |
| Molecular Formula | C19H27O9P |
| Purity | >95% by HPLC |
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Description
The most fully characterised member of a family of phosphate esters of a triene antibiotic; a topoisomerase II inhibitor; selective inhibition of protein phosphatase PP2A.
Specification
| Related CAS | 87860-39-7 (sodium salt) |
| Synonyms | (1E,7E,9E,11E)-3,6,13-trihydroxy-3-methyl-1-(6-oxo-3,6-dihydro-2H-pyran-2-yl)trideca-1,7,9,11-tetraen-4-yl dihydrogen phosphate; 2H-Pyran-2-one, 5,6-dihydro-6-[3,6,13-trihydroxy-3-methyl- 4-(phosphonooxy)-1,7,9,11-tridecatetraenyl]-, monosodiumsalt |
| Storage | -20°C |
| IUPAC Name | [(1E,3R,4R,6R,7Z,9Z,11E)-3,6,13-trihydroxy-3-methyl-1-[(2S)-6-oxo-2,3-dihydropyran-2-yl]trideca-1,7,9,11-tetraen-4-yl] dihydrogen phosphate |
| Canonical SMILES | CC(C=CC1CC=CC(=O)O1)(C(CC(C=CC=CC=CCO)O)OP(=O)(O)O)O |
| InChI | 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+ |
| InChI Key | ZMQRJWIYMXZORG-GZIFKOAOSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Powder |
| Boiling Point | 737.9°C at 760 mmHg |
| Density | 1.413 g/cm3 |
| Solubility | Soluble in water, optimial stability in aqueous buffered solutions at pH 6.5 |
Reference Reading
1. Fostriecin, an inhibitor of protein phosphatase 2A, limits myocardial infarct size even when administered after onset of ischemia
M V Cohen, R E Honkanen, C Weinbrenner, G S Liu, S C Armstrong, C P Baines, A H Walsh, C E Ganote, J M Downey Circulation . 1998 Sep 1;98(9):899-905. doi: 10.1161/01.cir.98.9.899.
Background:The role of protein phosphatases (PPs) during ischemic preconditioning in the rabbit heart was examined.Methods and results:Fostriecin, a potent inhibitor of PP2A, was administered to isolated rabbit hearts starting either 15 minutes before or 10 minutes after the onset of a 30-minute period of regional ischemia and continuing until the onset of reperfusion. After 2 hours of reperfusion, infarct size was measured with triphenyltetrazolium chloride. In a second study with isolated rabbit cardiomyocytes, the effect of fostriecin pretreatment was assessed by measuring changes in cell osmotic fragility during simulated ischemia. PP1 and PP2A activities of isolated control and ischemically preconditioned cells were also measured. In a third series of experiments, left ventricular biopsies of isolated rabbit hearts were obtained before and at selected times during 60 minutes of global ischemia, and the tissue was assayed for PP1 and PP2A activities. In isolated hearts pretreated with fostriecin, only 8% of the ischemic zone infarcted, significantly less than that in untreated control hearts (33%; P<0.001) but comparable to that in ischemically preconditioned hearts (9%; P<0.001 versus control). Significant protection was also observed in the hearts treated only after the onset of ischemia (18% infarction; P<0.05 versus control). In isolated myocytes, fostriecin also provided protection comparable to that produced by metabolic preconditioning. Preconditioning had no apparent effect on the activity of either PP1 or PP2A in isolated ventricular myocytes or ventricular tissue obtained from heart biopsies.Conclusions:Fostriecin, a potent inhibitor of PP2A, can protect the rabbit heart from infarction even when administered after the onset of ischemia. But inhibition of either PP1 or PP2A does not appear to be the mechanism of protection from ischemic preconditioning.
2. Effects of fostriecin on β2-adrenoceptor-driven responses in human mast cells
Peter T Peachell, Nahid Eskandari, Hamidrez J Ardakani, Reza Bastan J Immunotoxicol . 2017 Dec;14(1):60-65. doi: 10.1080/1547691X.2016.1259277.
As part of the intracellular processes leading to mast cell and basophil activation, phosphorylation of key substrates is likely to be important. These processes, mediated by phosphatases, are responsible for regulating phosphorylation. The aim of the present study was to determine effects fostriecin - a selective inhibitor of PP2A (protein phosphatase-2) - on β2-adrenoceptor-driven responses in human mast cells. Here, the effects of fostriecin (PP inhibitors) on the inhibition of histamine release from HLMC, on β-adrenoceptor-driven responses in mast cells and on desensitization were investigated. Long-term incubation (24 h) of mast cells with fostriecin (10-6M) resulted in a significant (p < 0.001) reduction in the maximal response (from 41.2 [± 3.0] to 29.9 [± 4.2] %) to salbutamol following fostriecin treatment. The results showed that fostriecin pretreatment significantly attenuated the inhibitory effects of salbutamol. Overall, the present study suggested that PP2A has an important role in regulating mast cell β2-adrenoceptors.
3. Catalytic Enantioselective Allylation of Acetylenic Aldehydes by Chiral Phosphoric Acid/Transition Metal Cooperative Catalysis: Formal Synthesis of Fostriecin
Shigenobu Umemiya, Masahiro Terada Org Lett . 2021 May 7;23(9):3767-3771. doi: 10.1021/acs.orglett.1c01166.
An enantioselective allylation of silyl-substituted acetylenic aldehydes by chiral phosphoric acid (CPA)/transition metal cooperative catalysis was developed. Enantioenriched homoallylic propargyl alcohols were obtained in good yields with excellent enantioselectivities (>99% ee) under mild conditions. Moreover, the shortest formal synthesis of fostriecin was achieved by the present enantioselective allylation protocol as the key step. The known intermediate of fostriecin reported by McDonald and co-worker was synthesized in only nine steps in 39% total yield.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
