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Myriocin

Item № 63150
CAS № 35891-70-4
Purity ≥98%
product image
                (CAS 35891-70-4)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $21.00 0.00
     5 mg $55.00 0.00
     10 mg $90.00 0.00
     25 mg $158.00 0.00

Pricing updated 2019-07-21. Prices are subject to change without notice.

Description
Synonyms
  • ISP-1
  • Thermozymocidin

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

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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
≥98%
Formulation
A crystalline solid
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
  • Fungi/Mycelia sterilia

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

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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 Journal of Antibiotics 47, 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 Biochemical and Biophysical Research Communications 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, 1255-1257 (1996).

5. Umehara, T., Sudoh, M., Yasui, F., et al. Serine palmitoyltransferase inhibitor suppresses HCV replication in a mouse model Biochemical and Biophysical Research Communications 346, 67-73 (2006).

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