See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Holiday Notification: Cayman Chemical will be closed Monday, May 28, 2012, in observance of the Memorial Day holiday. More…
Please feel free to continue placing orders via our website or via fax at 734-971-3640. You may send an email to customer service at custserv@caymanchem.com , or to technical support at techserv@caymanchem.com which we will respond to the next business day. Cayman will resume regular business hours and shipping schedules on Tuesday, May 29, 2012. Thank you for your patience and understanding.

Myriocin

Cayman Chemical Item Number 63150

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

Myriocin (CAS 35891-70-4)

See more

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
Copy SMILES to clipboard
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).

Show all 5 Hide all but first 3

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 2012-05-26. 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.

Related Products

Anisomycin New
azido-FTY720
D-erythro-Sphingosine C-18
FTY720
FTY720 Phosphate
Fumonisin B1
L-threo-Sphingosine C-18
Serine Palmitoyltransferase Polyclonal Antibody
Sphingosine-1-Phosphate
Show all 9 Hide all but first 3

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?