M1177
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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关于此项目
经验公式（希尔记法）:
C21H39NO6
化学文摘社编号:
分子量:
401.54
MDL编号:
UNSPSC代码:
51111800
PubChem化学物质编号:
NACRES:
NA.77
产品名称
Myriocin from Mycelia sterilia, ≥98% (HPLC), powder
质量水平
方案
≥98% (HPLC)
表单
powder
颜色
off-white
溶解性
methanol: 2 mg/mL
储存温度
2-8°C
SMILES字符串
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 key
ZZIKIHCNFWXKDY-GNTQXERDSA-N
应用
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.
制备说明
The material is readily and completely dissolved in 2 mg/ml methanol after heating at 55°C for several minutes.
警示用语：
Danger
危险声明
危险分类
Acute Tox. 3 Oral
储存分类代码
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
法规信息
涉药品监管产品
此项目有
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
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
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
Cigarette smoke increases cardiomyocyte ceramide accumulation and inhibits mitochondrial respiration
Tippetts TS, et al.
BMC Cardiovascular Disorders, 14(1), 165-165 (2014)
Lipopolysaccharide disrupts mitochondrial physiology in skeletal muscle via disparate effects on sphingolipid metabolism
Hansen ME, et al.
Shock, 44(6), 585-585 (2015)
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