A potent serine palmitoyltransferase inhibitor
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Myriocin

Item No. 63150

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-amino-3R,4R-dihydroxy-2-(hydroxymethyl)-14-oxo-6E-eicosenoic acid
CAS Number
35891-70-4
Synonyms
  • ISP-1
  • Thermozymocidin
Molecular Formula
C21H39NO6
Formula Weight
401.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Methanol: 2 mg/ml
SMILES
O=C(CCCCCC)CCCCCC/C=C/C[C@@H](O)[C@H](O)[C@@](C(O)=O)(N)CO
InChi Code
InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
InChi Key
ZZIKIHCNFWXKDY-GNTQXERDSA-N
Origin
Fungus/Mycelia sterilia
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $39

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    5 mg

    $87

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    10 mg

    $115

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    25 mg

    $260

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    Product Description

    Myriocin is an amino fatty acid antibiotic derived from certain thermophylic fungi, in this case Mycelia sterilia. It is a potent immunosuppressant having 10- to 100-fold more activity than cyclosporin A.1 Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. 2 It disrupts substratum adhesion of melanoma cells.3 It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis.2,4 Myriocin suppresses replication of the hepatitis C virus in a murine model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fujita, T., Inoue, K., Yamamoto, S., et al. Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite. J. Antibiot. (Tokyo) 47 (2), 208-215 (1994).

    2. Miyake, Y., Kozutsumi, Y., Nakamura, S., et al. Serine palmitoyltransferase is the primary target of a sphingosine-like immunosuppressant, ISP-1/myriocin. Biochem. Biophys. Res. Commun. 211(2), 396-403 (1995).

    3. Hidari, K.I.P.J., Ichikawa, S., Fujita, T., et al. Complete removal of sphingolipids from the plasma membrane disrupts cell to substratum adhesion of mouse melanoma cells. The Journal of Biological Chemisty 271(24), 14636-14641 (1996).

    4. Nakamura, S., Kozutsumi, Y., Sun, Y., et al. Dual roles of sphingolipids in signaling of the escape from and onset of apoptosis in a mouse cytotoxic T-cell line, CTLL-2. The Journal of Biological Chemisty 271(3), 1255-1257 (1996).

    5. Umehara, T., Sudoh, M., Yasui, F., et al. Serine palmitoyltransferase inhibitor suppresses HCV replication in a mouse model. Biochem. Biophys. Res. Commun. 346(1), 67-73 (2006).

    Product Citations

    Leier, H.C., Weinstein, J.B., Kyle, J.E., et al. A global lipid map defines a network essential for Zika virus replication. Nat. Commun. 11(1), 3652 (2020).