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Key Documents

476300

Sigma-Aldrich

Myriocin, Mycelia sterilia

A potent immunosuppressant.

Synonym(s):

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

Empirical Formula (Hill Notation):
C21H39NO6
CAS Number:
35891-70-4
Molecular Weight:
401.54
MDL number:
MFCD01632772
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

solubility

DMSO: 25 mg/mL

shipped in

ambient

storage temp.

−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

InChI key

ZZIKIHCNFWXKDY-GNTQXERDSA-N

General description

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.

Biochem/physiol Actions

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

Warning

Toxicity: Harmful (C)

Reconstitution

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

Other Notes

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.

Legal Information

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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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