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Myriocin (ISP-1) (CAS 35891-70-4)

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Application:An inhibitor of sphingolipid biosynthesis with immunosuppressive properties
CAS Number:35891-70-4
Purity:98%
Molecular Weight:401.54
Molecular Formula:C21H39NO6
Refer to Certificate of Analysis for lot specific data (including water content).
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Product NameCatalog #UnitPriceQtyAddFavorites
Myriocin (ISP-1) sc-201397 5 mg $60
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Description
Myriocin is a small-molecule inhibitor of serine palmitoyltransferase (SPTLC), isolated from the Mycelia sterilia thermophilic fungus, with immunosuppressive properties. SPTLC is responsible for catalyzing the committed step of sphingolipid biosynthesis; inhibition of this activity by myriocin leads to a depletion of sphingolipid levels in the cell. Apoptosis of interleukin-2-dependent cytotoxic T cells (CTLL-2) is induced by exposure to myriocin, and because this observed cell death is suspendable with addition of sphingosine, it is suggested that cellular levels of sphingolipids are important for signaling the onset of and escape from apoptosis in CTLL-2 T cells. This same observation indicates a mechanism for the immunosuppression associated with myriocin. Inhibition of sphingolipid production by myriocin is thought to disturb the composition of the lipid raft structure crucial for hepatitis C virus replication, indirectly suppressing proliferation of the virus. Adhesion to the extracellular matrix is shown to be disrupted in cells depleted of sphingolipids, and myriocin represents a tool for studying such behaviors of cells in sphingolipid-depleted states.
Technical Information
Appearance:Powder
Physical State:Solid
Solubility:Soluble in DMSO (heat briefly in boiling water bath) (25 mg/ml), dilute base (50 mM NaOH) (~5 mg/ml), and methanol (2 mg/ml). Insoluble in water.
Storage:Store at -20° C
Melting Point:322.23 °C
Boiling Point:636.67 °C at 760 mmHg
Density:1.12 g/cm3
Refractive Index:n20D 1.52
IC50:cell proliferation: IC50 = 15 nM (murine cytotoxic T cell line CTLL-2); allogenic mixed leukocyte response (MLR): IC50 = 3 nM (mouse)
Ki Data:serine palmitoyltransferase (SPT): Ki= 280 pM
pK Values:pKa: 1.79, pKb: 8.61
Safety and Reference Information
Transport:UN 2811, Class 6.1, Packing group III
WGK Germany:3
RTECS:JX3890000
PubChem CID:6438394
MDL Number:MFCD01632772
SMILES:CCCCCCC(=O)CCCCCCC=CCC(C(C(CO)(C(=O)O)N)O)O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
References
1. Fujita, T., et al. 1994. J. Antibiot. 47: 208-215. PMID: 8150717
2. Miyake, Y., et al. 1995. Biochem. Biophys. Res. Commun. 211: 396-403. PMID: 7794249
3. Hidari KIPJ, S., et al. 1996. J. Biol. Chem. 271: 14636-14641. PMID: 8662871
4. Nakamura, S., et al. 1996. J. Biol. Chem. 271: 1255-1257. PMID: 8576106
5. Umehara, T., et al. 2006. Biochem. Biophys. Res. Commun. 346: 67-73. PMID: 16750511
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