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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Myriocin

Cayman Chemical Item Number 63150

Thermozymocidin; ISP-1 (CAS 35891-70-4)

Myriocin (CAS 35891-70-4)

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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 (HCV) in a murine model.5

1 Fujita, T., Inoue, K., Yamamoto, S., et al. Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite. J Antibiot 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. 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. J Biol Chem 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. J Biol Chem 271 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 67-73 (2006).

Synonyms
  • Thermozymocidin
  • ISP-1
Formal Name 2-​amino-​3,​4-​dihydroxy-​2-​(hydroxymethyl)-​14-​oxo-​6-​eicosenoic acid
CAS Number 35891-70-4
Molecular Formula C21H39NO6
Formula Weight 401.5
Formulation A crystalline solid
Purity >98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C(CCCCCC)​CCCCCC/C=C/C[C@H]​(O)​[C@@H]​(O)​[C@]​(CO)​(N)​C(O)​=O

Background Reading

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

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. J Biol Chem 271(24) 14636-14641 (1996).

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).

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. J Biol Chem 271 1255-1257 (1996).

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

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Myriocin is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $15.00 $0.00
5 mg $68.00 $0.00
10 mg $120.00 $0.00
25 mg $263.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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