Fumonisin B1 A serine and threonine phosphatase inhibitor

Fumonisin B1 (CAS 116355-83-0)

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Synonym: Macrofusine
Application: A serine and threonine phosphatase inhibitor
CAS Number: 116355-83-0
Purity: ≥98%
Molecular Weight: 721.83
Molecular Formula: C34H59NO15
* Refer to Certificate of Analysis for lot specific data (including water content).
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Fumonisin B1 is a fungal metabolite produced by Fusarium moniliforme, that has been shown to inhibit protein serine/threonine phosphatases (PP1, PP2A, PP2B, PP2C, and PP5/T/K/H), and is most effective with PP5. It has been shown to stimulate the activation of mitogen-activated protein kinase. Fumonisin B1 has been observed to inhibit sphingolipid biosynthesis, preferentially inhibiting sphingomyelin biosynthesis versus glycosphingolipids in neuronal cells. In primary rat liver cells, fumonisin B1 blocked biosynthesis of de novo sphingolipids through LASS (ceramide synthase) inhibition. Caspase-3 activated or DNA fragmented apoptosis induced by fumonisin B1 binding to a TNF receptor has been documented in many human and rat cell lines. Fumonisin B1 has displayed immunotoxic effects by increasing expression of IL-1β, TNFα, IFN-γ; (interferon γ), IL-1α, IL-6, IL-10, IL-18 and IL-12 in varying mouse cells. Immunotoxicity of fumonisin B1 in human dendritic cells has been demonstrated through expression of chemokine CXCL9 and IFN-γ. Further, fumonisin B1 is an activator of Akt.


References

1. Merrill, A H., et al., 1993. Fumonisin B1 inhibits sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid biosynthesis in cultured neurons in situ. The Journal of biological chemistry. 268(36): 27299-306. PMID: 8262970
2. Fukuda, H., et al., 1996. Inhibition of protein serine/threonine phosphatases by fumonisin B1, a mycotoxin. Biochemical and biophysical research communications. 220(1): 160-5. PMID: 8602837
3. Wattenberg, E V., et al., 1996. Activation of mitogen-activated protein kinase by the carcinogenic mycotoxin fumonisin B1. Biochemical and biophysical research communications. 227(2): 622-7. PMID: 8878562
4. Merrill, A H., et al., 1996. Fumonisins: fungal toxins that shed light on sphingolipid function. Trends in cell biology. 6(6): 218-23. PMID: 15157459
5. Tripathy, Sandeep K., et al., 2008. Continuous engagement of a self-specific activation receptor induces NK cell tolerance. The Journal of experimental medicine. 205(8): 1829-41. PMID: 18606857
6. Stockmann-Juvala, H., et al., 2008. A review of the toxic effects and mechanisms of action of fumonisin B1. Human & experimental toxicology. 27(11): 799-809. PMID: 19244287

Physical State :
Solid
Solubility :
Soluble in water (25 mg/mL), methanol (10 mg/mL), acetonitrile, and DMSO (10 mM).
Storage :
Store at -20° C
Boiling Point :
~924.91° C at 760 mmHg (Predicted)
Density :
~1.3 g/cm3 (Predicted)
Refractive Index :
n20D 1.53
IC50 :
sphinganine N-acyl-transferase(ceramide synthase): IC50 = 0.1 µM; de novo sphingolipid biosynthesis: IC50 = 0.7 µM; protein phosphatases PP5: IC50 = 80 µM; protein phosphatases PP2Cα: IC50 = 300 µM; protein phosphatases PP2A: IC50 = 400 µM; protein phosphatases PP1γ2: IC50 = 500 µM; protein phosphatases PP2B: IC50 = 3000 µM
pK Values :
pKa: 3.64, pKb: 9.25
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
TZ8350000
PubChem CID :
62314
Merck Index :
14: 4289
MDL Number :
MFCD00133349
EC Number :
201-067-0
SMILES :
CCCC[C@H](C)[C@H]([C@@H](C[C@H](C)C[C@H](CCCC[C@H](C[C@@H]([C@H](C)N)O)O)O)OC(=O)C[C@H](CC(=O)O)C(=O)O)OC(=O)C[C@H](CC(=O)O)C(=O)O

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Fumonisin B1  Product Citations

See how others have used Fumonisin B1. Click on the entry to view the PubMed entry .

Citations 1 to 8 of 8 total

PMID: # 28645851  Tóth, EA. et al. 2017. Biochim. Biophys. Acta. 1862: 991-1000.

PMID: # 28220271  Almada, M. et al. 2017. Apoptosis. 22: 816-826.

PMID: # 28697598  Zheng, K. et al. 2017. J. Agric. Food Chem. 65: 6625-6637.

PMID: # 28123341  Huang, S. et al. 2017. Int. J. Biol. Sci. 13: 1-12.

PMID: # 25623391  Clarke, R. et al. 2015. Toxicol. Lett. 233: 278-86.

PMID: # 26503955  Bhat, NM. et al. 2015. J. Immunol. 195: 5178-88.

PMID: # 25110174  Clarke, R. et al. 2014. Toxicon. 90: 70-81.

PMID: # 11053253  Blázquez, C. et al. 2000. FASEB J. 14: 2315-2322.

Citations 1 to 8 of 8 total
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Rated 5 out of 5 by from Bl zquez Bl zquez, et. al. (PubMed ID 11053253) found that fumonisin B1, an inhibitor of ceramide synthase, blocked both palmitate-induced ceramide synthesis and palmitate-induced astrocyte death, even in the presence of TDGA. -SCBT Publication Review
Date published: 2015-06-01
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