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

Cayman Chemical Item Number 9000341

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

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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 DAG, 1,2-didecanoyl-sn-glycerol. Fluorescently-tagged lipids have been used to study their interactions with proteins,1 their utilization by cells and liposomes,2,3 and for the development of assays for lipid metabolism.4,5

1 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).

2 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).

3 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 91 873-881 (2006).

4 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 43 815-823 (2002).

5 Tani, M., Okino, N., Mitsutake, S., et al. Specific and sensitive assay for alkaline and neutral ceramidases involving C12-NBD-ceramide. J Biochem 125 746-749 (1999).

Formal Name 1-​NBD-​1,​2-​bis(O-​decanoyl-​sn-​glycerol)
Molecular Formula C29H46N4O8
Formula Weight 578.7
Formulation A solution in ethanol
Purity ≥98%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCCCCCCC(=O)​O[C@@H]​(CO)​COC(=O)​CCCCCCCCCNc1ccc([N]​(=O)​O)​c2nonc12

Background Reading

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).

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 91 873-881 (2006).

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).

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 43 815-823 (2002).

Tani, M., Okino, N., Mitsutake, S., et al. Specific and sensitive assay for alkaline and neutral ceramidases involving C12-NBD-ceramide. J Biochem 125 746-749 (1999).

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Size Global Purchasing
500 µg See a distributor in your region for pricing
1 mg See a distributor in your region for pricing
5 mg See a distributor in your region for pricing
10 mg See a distributor in your region for pricing

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Warning This product is not for human or veterinary use.

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