ALEXIS Biochemicals: Myriocin

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ALX-350-017

Revised 22-Apr-08

Fumonisin B1
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Other Tumor Promoters

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-017-M001		1 mg	60.00 USD
ALX-350-017-M005		5 mg	245.00 USD

Product Specification

FORMULA:	C₃₄H₅₉NO₁₅
MW:	721.8
CAS NUMBER:	116355-83-0
MERCK INDEX:	14: 4289
RTECS:	TZ8350000
SOURCE/HOST:	Isolated from Fusarium moniliforme.
PURITY:	~98% (TLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in water, methanol, DMSO or acetonitrile.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	MAY BE CARCINOGENIC. MAY BE MUTAGENIC. MAY BE TERATOGENIC. HARMFUL.

Product Description

Mycotoxin. Induces DNA damage in the liver and cancer. Inhibitor of sphingosine biosynthesis. Induces apoptosis. Activates Akt (protein kinase B; PKB), which leads to increased survival, inhibition of GSK-3β activity and post-translational stabilization of cyclin D1.

Product Specific Literature References

Inhibition of sphingolipid biosynthesis by fumonisins. Implications for diseases associated with Fusarium moniliforme: E. Wang, et al.; J. Biol. Chem. 266, 14486 (1991) Abstract; Full Text
Fumonisin B1 inhibits sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid biosynthesis in cultured neurons in situ: A.H. Merrill Jr., et al.; J. Biol. Chem. 268, 27299 (1993) Abstract; Full Text
Biological activities of fumonisins, mycotoxins from Fusarium moniliforme, in jimsonweed (Datura stramonium L.) and mammalian cell cultures: H.K. Abbas, et al.; Toxicon 31, 345 (1993) Abstract
Fumonisins and Alternaria alternata lycopersici toxins: sphinganine analog mycotoxins induce apoptosis in monkey kidney cells: H. Wang, et al.; PNAS 93, 3461 (1996) Abstract
A potential mechanism for fumonisin B(1)-mediated hepatocarcinogenesis: cyclin D1 stabilization associated with activation of Akt and inhibition of GSK-3beta activity: D. Ramljak, et al.; Carcinogenesis 21, 1537 (2000) Abstract
Implications of apoptosis for toxicity, carcinogenicity, and risk assessment: fumonisin B(1) as an example: Y.P. Dragan, et al.; Toxicol. Sci. 61, 6 (2001), Review Abstract
Fumonisin B(1): oxidative status and DNA damage in rats: A.M. Domijan, et al.; Toxicology 232, 163 (2007) Abstract

Further Categories Containing This Product:

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