1-NBD-decanoyl-2-decanoyl-sn-Glycerol

Description

Diacylglycerols (DAG) are produced by the hydrolysis of membrane phospholipids. They act as lipid second messengers, activating PKC and regulating cell growth and apoptosis. They also serve as substrates for DAG kinases for the production of phosphatidic acid, another important lipid messenger. 1-NBD-decanoyl-2-decanoyl-sn-glycerol has the fluorophore nitrobenzoxadiazole (NBD) attached to the ω-end of the terminal decanoyl chain of the model diacylglycerol (DAG), 1,2-didecanoyl-sn-glycerol. 1-NBD-decanoyl-2-decanoyl-sn-glycerol is likely to have excitation/emission maxima of approximately 470/541 nm, respectively, based on the maxima of various NBD-labeled phospholipids.¹ Fluorescently tagged lipids have been used to study their interactions with proteins, their utilization by cells and liposomes, and for the development of assays for lipid metabolism.^2,3,4,5,6

Uses

1-NBD-decanoyl-2-decanoyl-sn-glycerol is a diacylglycerol (DAG) derivative, which is labeled with a fluorescent group NBD. 1-NBD-decanoyl-2-decanoyl-sn-glycerol is the substrate for diacylglycerol kinase (DGK), and can be used for quantitative detection of the DGF enzyme kinetics in vitro, and the changes in DAG and PA during cell signaling[1].

References

1. Mazères, S., Schram, V., Tocanne, J.F., et al. 7-nitrobenz-2-oxa-1,3-diazole-4-yl-labeled phospholipids in lipid membranes: Differences in fluorescence behavior Biophys J. 71(1),327-335(1996).
2. Kumagai, K., Yasuda, S., Okemoto, K., et al. CERT mediates intermembrane transfer of various molecular species of ceramides J. Biol. Chem. 280(8),6488-6495(2005).
3. Luo, M., Jones, S.M., Peters-Golden, M., et al. Nuclear localization of 5-lipoxygenase as a determinant of leukotriene B₄ synthetic capacity Proc. Natl. Acad. Sci. USA 100(21),12165-12170(2003).
4. Moreno, M.J., Estronca, L.M.B.B., and Vaz, W.L.C. Translocation of phospholipids and dithionite permeability in liquid-ordered and liquid-disordered membranes Biophys. J. 91(3),873-881(2006).
5. Loidl, A., Claus, R., Deigner, H.P., et al. High-precision fluorescence assay for sphingomyelinase activity of isolated enzymes and cell lysates J. Lipid Res. 43(5),815-823(2002).
6. Tani, M., Okino, N., Mitsutake, S., et al. Specific and sensitive assay for alkaline and neutral ceramidases involving C₁₂-NBD-ceramide J. Biochem. 125(4),746-749(1999).