ALEXIS Biochemicals: Myriocin

ALX-350-274

Revised 16-Jun-08

Myriocin
SYNONYMS	ISP-1 Thermozymocidin 2S,3R,4R,6E-2-Amino-3,4-dihydroxy-2-hydroxymethyl-14-oxo-6-eicosenoic acid
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-274-M005		5 mg	90.00 USD

Product Specification

FORMULA:	C₂₁H₃₉NO₆
MW:	401.5
CAS NUMBER:	35891-70-4
RTECS:	JX3890000
PURITY:	≥98% (TLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO (25mg/ml; heat briefly in boiling water bath) or in dilute base (5mg/ml; 50mM NaOH).
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
HAZARD:	HARMFUL.

Product Description

Potent immunosuppressant ~10 to 100-fold more potent than cyclosporin A (Prod. No. ALX-380-002). Blocks sphingolipid biosynthesis by inhibiting serine palmitoyltransferase (K_i=0.28nM). Induces apoptosis by depletion of cellular sphingolipids. Inhibits proliferation of an IL-2-dependent mouse cytotoxic cell line CTLL-1 (IC₅₀=15nM).

Product Specific Literature References

Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite: T. Fujita, et al.; J. Antibiot. 47, 208 (1994) Abstract
Serine palmitoyltransferase is the primary target of a sphingosine-like immunosuppressant, ISP-1/myriocin: Y. Miyake, et al.; BBRC 211, 396 (1995) Abstract
Ceramide and its interconvertible metabolite sphingosine function as indispensable lipid factors involved in survival and dendritic differentiation of cerebellar Purkinje cells: S. Furuya, et al.; J. Neurochem. 71, 366 (1998) Abstract
Complete removal of sphingolipids from the plasma membrane disrupts cell to substratum adhesion of mouse melanoma cells: K. Hidari, et al.; J. Biol. Chem. 271, 14636 (1996) Abstract
Sli2 (Ypk1), a homologue of mammalian protein kinase SGK, is a downstream kinase in the sphingolipid-mediated signaling pathway of yeast: Y. Sun, et al.; Mol. Cell. Biol. 20, 4411 (2000) Abstract; Full Text
Effect of myriocin on plasma sphingolipid metabolism and atherosclerosis in apoE-deficient mice: M.R. Hojjati, et al.; J. Biol. Chem. 280, 10284 (2005) Abstract
Serine palmitoyltransferase inhibitor suppresses HCV replication in a mouse model: T. Umehara, et al.; BBRC 346, 67 (2006) Abstract