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M1177

Myriocin

Name: Myriocin
Brand: SIGMA

from Mycelia sterilia, ≥98% (HPLC), powder, immunosuppressant

Synonym(s):

(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid, ISP-I, Thermozymocidin

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₃₉NO₆

CAS Number:

35891-70-4

Molecular Weight:

401.54

UNSPSC Code:

51111800

PubChem Substance ID:

24896622

NACRES:

NA.77

MDL number:

MFCD01632772

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

200

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Properties

Product Name

Myriocin from Mycelia sterilia, ≥98% (HPLC), powder

Quality Level

200

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

methanol: 2 mg/mL

storage temp.

2-8°C

SMILES string

CCCCCCC(=O)CCCCCC\C=C\C[C@@H](O)[C@H](O)[C@@](N)(CO)C(O)=O

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

Description

Application

Myriocin from Mycelia sterilia has been used as an inhibitor of sphingolipid or ceramide biosynthesis in various studies.

Biochem/physiol Actions

Myriocin from Mycelia sterilia is a fungal metabolite with potent immunosuppressant activity. It inhibits serine palmitoyltransferase at picomolar concentrations blocking synthesis of ceramide, a precursor of sphingomyelin and glycosphingolipids. It disrupts substratum adhesion of melanoma cells. It has been suggested that its immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction.

Preparation Note

The material is readily and completely dissolved in 2 mg/ml methanol after heating at 55°C for several minutes.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000520125

0000488206

0000448170

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Ceramide mediates vascular dysfunction in diet-induced obesity by PP2A-mediated dephosphorylation of the eNOS-Akt complex.

Quan-Jiang Zhang et al.

Diabetes, 61(7), 1848-1859 (2012-05-16)

Vascular dysfunction that accompanies obesity and insulin resistance may be mediated by lipid metabolites. We sought to determine if vascular ceramide leads to arterial dysfunction and to elucidate the underlying mechanisms. Pharmacological inhibition of de novo ceramide synthesis, using the

Inhibition of serine palmitoyl transferase I reduces cardiac ceramide levels and increases glycolysis rates following diet-induced insulin resistance.

John R Ussher et al.

PloS one, 7(5), e37703-e37703 (2012-05-26)

Diet-induced obesity (DIO) leads to an accumulation of intra-myocardial lipid metabolites implicated in causing cardiac insulin resistance and contractile dysfunction. One such metabolite is ceramide, and our aim was to determine the effects of inhibiting de novo ceramide synthesis on

Cigarette smoke increases cardiomyocyte ceramide accumulation and inhibits mitochondrial respiration

Tippetts TS, et al.

BMC Cardiovascular Disorders, 14(1), 165-165 (2014)

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