Application

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.

Biochem/physiol Actions

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.

General description

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.

Other Notes

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.

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.

Packaging

30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800818C-10mg)

Storage and Stability

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.