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MYRIOCIN

Product Name
MYRIOCIN
CAS No.
35891-70-4
Chemical Name
MYRIOCIN
Synonyms
ISP-1;ISP-I;C001996;MYRIOCIN;6e))-4s*;NSC 177379;THERMOZYMOCIDIN;Spi-1 inhibitor;Myriocin (ISP-1);Isp-1 suppressant
CBNumber
CB0207522
Molecular Formula
C21H39NO6
Formula Weight
401.54
MOL File
35891-70-4.mol
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MYRIOCIN Property

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
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
22
Safety Statements 
24/25
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
JX3890000
HS Code 
29225090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M1177
Product name
Myriocin from Mycelia sterilia
Purity
≥98% (HPLC), powder
Packaging
5mg
Price
$84.7
Updated
2024/03/01
Sigma-Aldrich
Product number
476300
Product name
Myriocin from Mycelia sterilia
Purity
A potent immunosuppressant.
Packaging
5mg
Price
$166
Updated
2024/03/01
Cayman Chemical
Product number
63150
Product name
Myriocin
Purity
≥98%
Packaging
1mg
Price
$28
Updated
2024/03/01
Cayman Chemical
Product number
63150
Product name
Myriocin
Purity
≥98%
Packaging
5mg
Price
$68
Updated
2024/03/01
Sigma-Aldrich
Product number
M1177
Product name
Myriocin from Mycelia sterilia
Purity
≥98% (HPLC), powder
Packaging
25mg
Price
$295
Updated
2024/03/01
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MYRIOCIN Chemical Properties,Usage,Production

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 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.

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]

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.

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

MYRIOCIN Preparation Products And Raw materials

Raw materials

Preparation Products

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35891-70-4, MYRIOCINRelated Search:

Ampicillin COLISTIN Metronidazole Ceramides METYRAPONE JZL 184 Polymyxin B Chaetomium globosum L(+)-allo-Threonine 2-Methyl-D-serine MYRIOCIN 2-Methyl-L-serine 2-AMINO-3-HYDROXY-2-METHYLBUTANOIC ACID dl-3-hydroxynorvaline METHYL 6-TRANS-OCTADECENOATE (2S,3S)-2-AMINO-3-HYDROXY-PENTANOIC ACID (2S,3S)-3-HYDROXY-L-ISOVALINE (D,L)-2-AMINO-HEPT-6-ENOIC ACID

  • MYRIOCIN
  • MYRIOCIN, MYCELIA STERILIA
  • THERMOZYMOCIDIN
  • 2S-amino-3R,4R-dihydroxy-2-(hydroxymethyl)-14-oxo-6E-eicosenoic acid
  • Myriocin, 99%, from Mycelia sterilia
  • Myriocin, Mycelia sterilia - CAS 35891-70-4 - Calbiochem
  • 6e))-4s*
  • 6-eicosenoicacid,2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-,(2s-(2r*,3s
  • [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
  • ISP-1
  • ISP-I
  • MYRIOCIN FROM MYCELIA STERILIA
  • 2-Amino-2-hydroxymethyl-3,4-dihydroxy-14- oxoeicos-6-enoic acid
  • C001996
  • Isp-1 suppressant
  • Spi-1 inhibitor
  • (2S,3R,4R)-(E)-2-AMino-3,4-dihydroxy-2-hydroxyMethyl-14-oxoeicos-6-enoic Acid
  • [2S-(2R*,3S*,4S*,6E)]-2-AMino-3,4-dihydroxy-2-(hydroxyMethyl)-14-oxo-6-eicosenoic Acid
  • NSC 177379
  • 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
  • (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-oxoicos-6-enoic acid
  • TherMozyMocidin, ISP 1
  • ISP-I NSC 177379 Myriocin Thermozymocidin
  • Myriocin (ISP-1)
  • 6-Eicosenoic acid, 2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-, (2S,3R,4R,6E)-
  • ISP-I|||Thermozymocidin
  • 35891-70-4
  • C21H39NO6
  • antibiotic