Myriocin

Cayman Chemical Item Number 63150

ISP-1; Thermozymocidin (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
  • ISP-1
  • Thermozymocidin
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
InCHI Code
Copy InCHI code to clipboard
​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?/m0/s1
InCHI Key
Copy InCHI key to clipboard
ZZIKIHCNFWXKDY-QAJVWVOBSA-N

Download free InCHI Key generation software

Myriocin is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $19.00 $0.00
5 mg $52.00 $0.00
10 mg $98.00 $0.00
25 mg $165.00 $0.00
Bulk Contact
Cart Total $0.00

Please Login or Register to use this page.

Pricing updated 2014-04-19. 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
azido-FTY720
Cyclosporin A New
D-erythro-Sphingosine C-18
FTY720
FTY720 Phosphate
Fumonisin B1
L-threo-Sphingosine C-18
Serine Palmitoyltransferase Polyclonal Antibody
Sphingosine-1-Phosphate
Show all 10 Hide all but first 3

Downloads

Batch-specific Information

Get batch-specific data and documents by batch number


Separate multiple batch numbers with commas

Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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

Join us! · Experimental Biology 2014 · San Diego, California · April 26-30, 2014 · Booth 323
Other Resources
About Cayman Management Team Company Profile 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 Conference Travel Grants

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 2014 Cayman Chemical Company

Manufacturer, supplier, and vendor of biochemical reagents, assay kits, forensic chemistry standards, antibodies, and proteins for scientific research · Buy now! · Analytical testing services and custom synthesis also available

Lost password?