| Identification | Back Directory | [Name]
MYRIOCIN | [CAS]
35891-70-4 | [Synonyms]
ISP-1
ISP-I
C001996
MYRIOCIN
6e))-4s*
NSC 177379
Spi-1 inhibitor
THERMOZYMOCIDIN
Myriocin (ISP-1)
Isp-1 suppressant
TherMozyMocidin, ISP 1
MYRIOCIN, MYCELIA STERILIA
MYRIOCIN FROM MYCELIA STERILIA
Myriocin, 99%, from Mycelia sterilia
Myriocin, Mycelia sterilia - CAS 35891-70-4 - Calbiochem
2-Amino-2-hydroxymethyl-3,4-dihydroxy-14- oxoeicos-6-enoic acid
2S-amino-3R,4R-dihydroxy-2-(hydroxymethyl)-14-oxo-6E-eicosenoic acid
6-eicosenoicacid,2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-,(2s-(2r*,3s
(2S,3R,4R,E)-2-aMino-3,4-dihydroxy-2-(hydroxyMethyl)-14-oxoicos-6-enoic acid
(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-icosenoic acid
(2S,3R,4R)-(E)-2-AMino-3,4-dihydroxy-2-hydroxyMethyl-14-oxoeicos-6-enoic Acid
[2S,3R,4R,6E]-2-AMINO-3,4-DIHYDROXY-2-[HYDROXYMETHYL]-14-OXO-6-EICOSENOIC ACID
[2S,3R,4R]-(E)-2-AMINO-3,4-DIHYDROXY-2-[HYDROXYMETHYL]-14-OXO-6-EICOSENOIC ACID
6-Eicosenoic acid, 2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-, (2S,3R,4R,6E)-
[2S-(2R*,3S*,4S*,6E)]-2-AMino-3,4-dihydroxy-2-(hydroxyMethyl)-14-oxo-6-eicosenoic Acid
ISP-I NSC 177379 Myriocin Thermozymocidin
Thermozymocidin, ISP-I, (2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid
ISP-I, Thermozymocidin, (2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid | [EINECS(EC#)]
636-862-5 | [Molecular Formula]
C21H39NO6 | [MDL Number]
MFCD01632772 | [MOL File]
35891-70-4.mol | [Molecular Weight]
401.54 |
| Chemical Properties | Back Directory | [Melting point ]
170-172℃ | [Boiling point ]
636.7±55.0 °C(Predicted) | [density ]
1.123±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
methanol: 2 mg/mL
| [form ]
powder
| [pka]
1.79±0.50(Predicted) | [color ]
off-white
| [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 4 months. | [InChIKey]
ZZIKIHCNFWXKDY-XFXZXTDPSA-N | [CAS DataBase Reference]
35891-70-4 |
| Hazard Information | Back Directory | [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. Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. It disrupts substratum adhesion of melanoma cells. It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis. Myriocin suppresses replication of the hepatitis C virus in a murine model. | [Chemical Properties]
White powder | [Uses]
Myriocin is a atypical amino acid and an antibiotic with potent immunosuppressant activity. Studies suggest that the immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis
induction. Myriocin very potent inhibitor of serine palmitoyltransferase and thus blocks the synthesis ceramide, a precursor in sphingomyelin and glycosphingolipid biosynthesis. As a result Myriocin i
s a useful biochemical research tool for depleting cells of sphingolipids. | [Uses]
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. Myriocin is a potent inhibitor of serine palmitoyltransferase (Ki = 0.28 nM), the enzyme that catalyzes the first step of sphingolipid biosynthesis. It disrupts substratum adhesion of melanoma cells. It also suppresses cell proliferation in the murine cytotoxic T cell line CTLL-2 (IC50 = 15 nM) via apoptosis. Myriocin suppresses replication of the hepatitis C virus in a murine model.[Cayman Chemical] | [Uses]
Myriocin is an α-amino fatty acid derived from several genera of fungi, notably Myriococcum, Melanconis and Isaria. Myriocin potently inhibits sphingosine biosynthesis by blocking the first enzyme in the pathway, serine palmitoyltransferase. Myriocin induces apoptosis by depleting cellular sphingolipids, inhibits proliferation of IL-2-dependent mouse cytotoxic cells and is a potent immunosuppressant. | [Definition]
ChEBI: An amino acid-based antibiotic derived from certain thermophilic fungi; acts as a potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Myriocin also possesses immunosuppressant activity. | [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. | [Biological Activity]
Potent immunosuppressant ~10 to 100-fold more potent than cyclosporin A . Blocks sphingolipid biosynthesis by inhibiting serine palmitoyltransferase (Ki=0.28nM), therefore useful as a tool to deplete cells of sphingolipids. Induces apoptosis by depletion of cellular sphingolipids. Inhibits proliferation of an IL-2-dependent mouse cytotoxic cell line CTLL-1 (IC50=15nM). | [Biochem/physiol Actions]
Product does not compete with ATP. | [References]
1) Fujita et al.(1994) Fungal metabolites. Part 11. A potent immunosuppressive activity found in Isaria sinclairii metabolite; J. Antibiot. 47 208
2) Miyake et al. (1995) Serine palmitoyltransferase is the primary target of a sphingosine-like immunosuppressant ISP-1/myriocin; Biochem. Biophys. Res. Commun. 211 396
3) Lee et al. (2012) Myriocin, a serine palmitoyltransferase inhibitor, suppresses tumor growth in a murine melanoma model by inhibiting de novo sphingolipid synthesis; Cancer Biol Ther. 13 92 |
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