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Merck
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Key Documents

476300

Sigma-Aldrich

Myriocin, Mycelia sterilia

A potent immunosuppressant.

Sinónimos:

Myriocin, Mycelia sterilia, ISP-1, Thermozymocidin, [2S,3R,4R]-(E)-2-Amino-3,4-dihydroxy-2-[hydroxymethyl]-14-oxo-6-eicosenoic Acid

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About This Item

Fórmula empírica (notación de Hill):
C21H39NO6
Número de CAS:
35891-70-4
Peso molecular:
401.54
Número MDL:
MFCD01632772
Código UNSPSC:
12352200

Nivel de calidad

100

Análisis

≥95% (TLC)

formulario

solid

fabricante / nombre comercial

Calbiochem®

condiciones de almacenamiento

OK to freeze

color

white

solubilidad

DMSO: 25 mg/mL

Condiciones de envío

ambient

temp. de almacenamiento

−20°C

InChI

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+/m1/s1

Clave InChI

ZZIKIHCNFWXKDY-GNTQXERDSA-N

Descripción general

A potent immunosuppressant. Displays 10- to 100-fold more potent immunosuppressant activity than cyclosporin A. Potently inhibits serine palmitoyltransferase (SPT; Ki = 280 pM) thereby blocking the synthesis of ceramide. Disrupts substratum adhesion of melanoma cells. Inhibits cell proliferation and induces apoptosis in IL-2 dependent murine cytotoxic T lymphocyte cell line CTLL-2.

Acciones bioquímicas o fisiológicas

Cell permeable: no
Primary Target
Serine palmitoyltransferase
Product does not compete with ATP.
Reversible: no
Target Ki: 280 pM against serine palmitoyltransferase

Advertencia

Toxicity: Harmful (C)

Reconstitución

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Otras notas

Hanada, K., et al. 2000. Biochem. Pharmacol.59, 1211.
Chen, J.K., et al. 1999. Chem. Biol. 6, 221.
Hidari, K.I.P.J., et al. 1996. J. Biol. Chem. 271, 14636.
Nakamura, S., et al. 1996. J. Biol. Chem. 271, 1255.
Mikaye, Y., et al. 1995. Biochem. Biophys. Res. Commun. 211, 396.
Fujita, T., et al. 1994. J. Antibiot. 47, 208.

Información legal

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H301

Clasificaciones de peligro

Acute Tox. 3 Oral

Código de clase de almacenamiento

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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K Hanada et al.
Biochemical pharmacology, 59(10), 1211-1216 (2000-03-29)
In the present study, we demonstrate a model cell system for evaluating the specificity of inhibitors of serine palmitoyltransferase (SPT), the enzyme that catalyzes the first step of sphingolipid biosynthesis. The LY-B strain is a Chinese hamster ovary (CHO) cell
T Fujita et al.
The Journal of antibiotics, 47(2), 208-215 (1994-02-01)
A potent immunosuppressive activity was found in the culture broth of the fungus Isaria sinclairii (ATCC 24400). The metabolite, ISP-I ((2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2- hydroxymethyl-14-oxoeicos-6-enoic acid, myriocin = thermozymocidin) suppressed the proliferation of lymphocytes in mouse allogeneic mixed lymphocyte reaction, but had no
J K Chen et al.
Chemistry & biology, 6(4), 221-235 (1999-04-01)
Myriocin is a natural product that potently induces apoptosis of a murine cytotoxic T lymphocyte cell line (CTLL-2) and inhibits a serine palmitoyltransferase (SPT) activity that has been detected in cell extracts and is thought to initiate sphingolipid biosynthesis. Because
S Nakamura et al.
The Journal of biological chemistry, 271(3), 1255-1257 (1996-01-19)
In our previous study, the sphingosine-like immunosuppressant, ISP-1, was found to suppress the proliferation of an interleukin-2-dependent cytotoxic T cell line, CTLL-2, through the inhibition of serine palmitoyltransferase, which catalyzes the committed step of sphingolipid biosynthesis. Analysis of the effect
Y Miyake et al.
Biochemical and biophysical research communications, 211(2), 396-403 (1995-06-15)
ISP-1/myriocin is a new type of remarkably potent immunosuppressant, the structure of which is homologous to sphingosine. ISP-1/myriocin inhibited the proliferation of an IL-2-dependent mouse cytotoxic T cell line, CTLL-2, at nanomole concentrations. ISP-1/myriocin inhibits serine palmitoyltransferase activity at picomole
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