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方案
>99% (TLC)
表单
liquid
包装
pkg of 1 × 5 mL (800818C-10mg)
制造商/商品名称
Avanti Research™ - A Croda Brand 800818C
浓度
2 mg/mL (800818C-10mg)
脂质类型
neutral lipids
neutral glycerides
运输
dry ice
储存温度
−20°C
SMILES字符串
O([C@H](COC(=O)CCCCCCCCCCCCCCCCC)CO)C(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI
1S/C41H72O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,39,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3/b13-11-,19-17-,24-22-,30-28-/t39-/m0/s1
InChI key
NSXLMTYRMFVYNT-IUJDHQGTSA-N
一般描述
18:0-20:4 DG or 1-stearoyl-2-arachidonoyl-sn-glycerol is a diglyceride. Diglycerides contain two fatty acids linked to the glycerol backbone with an ester bond.
应用
18:0-20:4 DG or 1-stearoyl-2-arachidonoyl-sn-glycerol has been used to study its effect on conventional protein kinase C (cPKC) and novel protein kinase C (nPKC) isozymes in vitro. It has also been used as a substrate for the measurement of diacylglycerol kinase δ (DGK#948;) and DGKη1 activity in vitro.
生化/生理作用
In biochemical signaling, diacylglycerol (DAG) functions as a second messenger signaling lipid, and is a product of the hydrolysis of the phospholipid PIP2 (phosphatidylinositolbisphosphate) by the enzyme phospholipase C (PLC) (a membrane-bound enzyme) that, through the same reaction, produces inositol trisphosphate (IP3). Although inositol trisphosphate (IP3) diffuses into the cytosol, DAG remains within the plasma membrane due to its hydrophobic properties. IP3 stimulates the release of calcium ions from the smooth endoplasmic reticulum, whereas DAG is a physiological activator of protein kinase C (PKC). The production of DAG in the membrane facilitates translocation of PKC from the cytosol to the plasma membrane.
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.
包装
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800818C-10mg)
储存及稳定性
Diacylglycerols are conveniently stored in chloroform solutions in glass vials with PTFE-lined caps at -20°C. Under these conditions acyl migration is minimal. Avoid plastic when handling chloroform solutions.
其他说明
Delivery to cells:
Dry samples of diacylglycerol in chloroform, using a stream of nitrogen. Dissolve the residue in an appropriate volume of ethanol or DMSO, then dilute to the desired aqueous medium.
Dry samples of diacylglycerol in chloroform, using a stream of nitrogen. Dissolve the residue in an appropriate volume of ethanol or DMSO, then dilute to the desired aqueous medium.
Effective concentration:
Most biological responses saturate at 20 to 250 μM sn-1,2-dioctanoylglycerol. Only sn-1,2 isomers appear to be active.
Most biological responses saturate at 20 to 250 μM sn-1,2-dioctanoylglycerol. Only sn-1,2 isomers appear to be active.
Precaution: Since short chain Diacylglycerols mimic effects of the tumor-promoting phorbol diesters in a number of biological systems, extra care should be employed in their handling. Treatment of solutions, vessels and other articles with 1N NaOH before washing or discarding will destroy diacylglycerols.
法律信息
Avanti Research is a trademark of Avanti Polar Lipids, LLC
警示用语：
Danger
危险分类
Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3
靶器官
Central nervous system, Liver,Kidney
WGK
WGK 3
法规信息
易制毒化学品（2类）
危险化学品
Robert C Murphy et al.
Journal of lipid research, 60(2), 219-226 (2019-01-05)
Leukotrienes (LTs) are autacoids derived from the precursor arachidonic acid (AA) via the action of five-lipoxygenase (5-LO). When inflammatory cells are activated, 5-LO translocates to the nuclear membrane to initiate oxygenation of AA released by cytosolic phospholipase A2 (cPLA2) into
Hiromichi Sakai et al.
The Journal of biological chemistry, 289(38), 26607-26617 (2014-08-13)
Decreased expression of diacylglycerol (DG) kinase (DGK) δ in skeletal muscles is closely related to the pathogenesis of type 2 diabetes. To identify DG species that are phosphorylated by DGKδ in response to high glucose stimulation, we investigated high glucose-dependent
Yuuna Kamiya et al.
Biochemistry and biophysics reports, 7, 361-366 (2016-07-20)
A variety of diacylglycerol (DG) molecular species are produced in stimulated cells. Conventional (α, βII and γ) and novel (δ, ε, η and θ) protein kinase C (PKC) isoforms are known to be activated by DG. However, a comprehensive analysis
Sruthi S Balakrishnan et al.
Journal of cell science, 131(15) (2018-07-08)
The activation of phospholipase C (PLC) is a conserved mechanism of receptor-activated cell signaling at the plasma membrane. PLC hydrolyzes the minor membrane lipid phosphatidylinositol 4,5-bisphosphate [PI(4,5)P2], and continued signaling requires the resynthesis and availability of PI(4,5)P2 at the plasma
Maria Saliakoura et al.
Oncogene, 39(14), 2948-2960 (2020-02-09)
Enhanced prostaglandin production promotes the development and progression of cancer. Prostaglandins are generated from arachidonic acid (AA) by the action of cyclooxygenase (COX) isoenzymes. However, how cancer cells are able to maintain an elevated supply of AA for prostaglandin production
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