3-dodecanoyl-NBD Cholesterol

Cayman Chemical Item Number 13220

3-C₁₂-NBD Cholesterol

Description

C-12 NBD Cholesterol is a fluorescently-tagged cholesterol with the hydrophilic NBD fluorophore attached to the hydrophilic end of cholesterol, separated by a 12-carbon spacer. This design allows the cholesterol to properly orient in membrane bilayers while the fluorescent tag is presented outside of the bilayer. This should model the behavior of cholesterol in membranes better than the previously-used 25-NBD cholesterol, which positions NBD directly on the 25^th carbon of cholesterol at the hydrophobic terminus. 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.^1,2,3,4

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 missing reference text

4 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).

Synonyms

3-C12-NBD Cholesterol

Formal Name

12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-(3S,10R,13R)-3-methoxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-tetradecahydro-1H-cyclopenta[α]phenanthrene

Molecular Formula

C₄₅H₇₀N₄O₅

Formula Weight

747.1

Formulation

A solution in ethanol

Purity

≥98%

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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[H]N(C1=CC=C([N+]([O-])=O)C2=NON=C12)CCCCCCCCCCCCC(O[C@H](C3)CC[C@@]4(C)C3=CC[C@]5([H])[C@]4([H])CC[C@@]6(C)[C@@]5([H])CC[C@]6([H])[C@@](C)([H])CCCC(C)C)=O

Background Reading

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).

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).

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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500 µg 
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1 mg 
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3-dodecanoyl-NBD Cholesterol