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M1177

Sigma-Aldrich

Myriocin

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

别名:

(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

经验公式（希尔记法）:
C21H39NO6
CAS号:
35891-70-4
分子量:
401.54
MDL號碼:
MFCD01632772
分類程式碼代碼:
51111800
PubChem物質ID:
24896622
NACRES:
NA.77

product name

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

品質等級

200

化驗

≥98% (HPLC)

形狀

powder

顏色

off-white

溶解度

methanol: 2 mg/mL

儲存溫度

2-8°C

SMILES 字串

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 密鑰

ZZIKIHCNFWXKDY-GNTQXERDSA-N

應用

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

生化／生理作用

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.

象形圖

Skull and crossbones
GHS06

訊號詞

Danger

危險聲明

H301

危險分類

Acute Tox. 3 Oral

儲存類別代碼

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

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

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

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Lipopolysaccharide disrupts mitochondrial physiology in skeletal muscle via disparate effects on sphingolipid metabolism
Hansen ME, et al.
Shock, 44(6), 585-585 (2015)
Maija Ruuth et al.
European heart journal, 39(27), 2562-2573 (2018-07-10)
Low-density lipoprotein (LDL) particles cause atherosclerotic cardiovascular disease (ASCVD) through their retention, modification, and accumulation within the arterial intima. High plasma concentrations of LDL drive this disease, but LDL quality may also contribute. Here, we focused on the intrinsic propensity
Cigarette smoke increases cardiomyocyte ceramide accumulation and inhibits mitochondrial respiration
Tippetts TS, et al.
BMC Cardiovascular Disorders, 14(1), 165-165 (2014)
Fernando Martínez-Montañés et al.
Journal of lipid research, 57(11), 2040-2050 (2016-11-03)
Long-chain bases (LCBs) are the precursors to ceramide and sphingolipids in eukaryotic cells. They are formed by the action of serine palmitoyl-CoA transferase (SPT), a complex of integral membrane proteins located in the endoplasmic reticulum. SPT activity is negatively regulated
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
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