Merck
CN

800800O

Avanti

08:0 DG

1,2-dioctanoyl-sn-glycerol, neat oil

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别名:
DG(8:0/8:0/0:0)
经验公式(希尔记法):
C19H36O5
CAS号:
分子量:
344.49
NACRES:
NA.25

检测方案

>99% (TLC)

形式

liquid

包装

pkg of 1 × 10 mg (with screw cap (800800O-10mg))
pkg of 1 × 25 mg (with screw cap (800800O-25mg))

manufacturer/tradename

Avanti Polar Lipids 800800O

lipid type

neutral lipids
neutral glycerides

运输

dry ice

储存温度

−20°C

InChI

1S/C19H36O5/c1-3-5-7-9-11-13-18(21)23-16-17(15-20)24-19(22)14-12-10-8-6-4-2/h17,20H,3-16H2,1-2H3/t17-/m0/s1

InChI key

ZQBULZYTDGUSSK-KRWDZBQOSA-N

一般描述

08:0 DG (1,2-dioctanoyl-sn-glycerol), also referred as di-C8, is a short-chain cell-permeable diacyl glycerol.
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.

应用

08:0 DG may be used:
  • to study its stimulatory effect on protein kinase C (PKC) in human cell lines
  • as a lipid cofactor in PKC activity assay
  • in vesicular-fusion protein Sec-18 binding studies

生化/生理作用

08:0 DG (1,2-dioctanoyl-sn-glycerol) mimics endogenous diacylglycerol andis a active phorbol compund. It activates protein kinase C (PKC). It binds to the epidermal growth factor (EGF) receptor similar to 4β-phorbol 12β-myristate 13α-acetate (PMA). DiC8 elevates the phosphoserine and phosphothreonine levels. DiC8 stimulates the release of superoxide in neutrophils. It downregulates nicotinic acetylcholine receptor α1 subunit 1 (nAChR1).

包装

5 mL PTFE Vial with Screw Cap (800800O-10mg)
5 mL PTFE Vial with Screw Cap (800800O-25mg)

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.
Effective concentration:
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.

储存分类代码

10 - Combustible liquids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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Regulation of human monocyte surface antigen expression. I. Up-modulation of Mo3e antigen expression on U-937 and HL-60 cells stimulated by pharmacologic activators of protein kinase C
Todd RF, et al.
Blood, 68(5), 1154-1161 (1986)
Phosphatidic acid induces conformational changes in Sec18 protomers that prevent SNARE priming
Starr ML, et al.
Test, 294(9), 3100-3116 (2019)
Rottlerin is a mitochondrial uncoupler that decreases cellular ATP
Soltoff SP
Test, 276(41), 37986-37992 (1986)
1, 2-dioctanoyl-sn-glycerol can stimulate neutrophils by different mechanisms. Evidence for a pathway that does not involve phosphorylation of the 47-kDa protein.
Badwey JA, et al.
The Journal of biological chemistry, 264(34), 20676-20682 (1989)
sn-1, 2-Dioctanoylglycerol. A cell-permeable diacylglycerol that mimics phorbol diester action on the epidermal growth factor receptor and mitogenesis.
Davis RJ, et al.
The Journal of biological chemistry, 260(3), 1562-1566 (1985)

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