C-12 NBD-dihydro-Ceramide

Cayman Chemical Item Number 10008097

N-C₁₂-NBD-D-erythro-dihydro-Sphingosine

Description

Ceramidase catalyzes the hydrolysis of the N-acyl linkage between the fatty acid and sphingosine base in ceramide to produce sphingosine and a free fatty acid. Three isoforms of ceramidases (acid, neutral, and alkaline) have been characterized based on differences in their catalytic pH optimum.^1,2 C-12 NBD-dihydro-ceramide is a fluorescent ceramide analog that contains a saturated bond in the C-4/C-5 position of the sphingosine backbone. C-12 NBD ceramide, which contains the C-4/C-5 double bond, is a fluorescent ceramidase substrate that can be used for the measurement of alkaline and neutral ceramidase activity from a variety of sources.³ C-12 NBD-dihydro-ceramide may exhibit reduced activity in ceramidase assays compared to C-12 NBD ceramide. This is based on the observation that saturation of the C-4/C-5 sphingosine bond in C-16-ceramide results in approximately a 10-fold reduction in efficiency as a substrate for rat brain ceramidase compared to the unsaturated substrate.⁴ However, experimental characterization of C-12 NBD-dihydro-ceramide as a ceramidase substrate needs to be performed.

1 Tani, M., Okino, N., Mori, K., et al. Molecular cloning of the full-length cDNA encoding mouse neutral ceramidase. A novel but highly conserved gene family of neutral/alkaline ceramidases. J Biol Chem 275(15) 11229-11234 (2000).

2 Ferlinz, K., Kopal, G., Bernardo, K., et al. Human acid ceramidase. Processing, glycosylation, and lysosomal targeting. J Biol Chem 276 (38) 35352-35360 (2001).

3 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).

4 Bawab, S.E., Usta, J., Roddy, P., et al. Substrate specificty of rat brain ceramidase. J Lipid Res 43 141-148 (2002).

Synonyms

N-C12-NBD-D-erythro-dihydro-Sphingosine

Formal Name

N-[(1,2)-2-hydroxy-1-(hydroxymethyl)heptadecyl]-12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-dodecanamide

Molecular Formula

C₃₆H₆₃N₅O₆

Formula Weight

661.9

Formulation

A solution in chloroform:ethanol (1:1)

Purity

≥98%

λ_max

229, 333, 465 nm

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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CCCCCCCCCCCCCCCC(O)[C@@H](CO)NC(=O)CCCCCCCCCCCNc1ccc([N](=O)O)c2nonc12

Background Reading

Tani, M., Okino, N., Mori, K., et al. Molecular cloning of the full-length cDNA encoding mouse neutral ceramidase. A novel but highly conserved gene family of neutral/alkaline ceramidases. J Biol Chem 275(15) 11229-11234 (2000).

Ferlinz, K., Kopal, G., Bernardo, K., et al. Human acid ceramidase. Processing, glycosylation, and lysosomal targeting. J Biol Chem 276 (38) 35352-35360 (2001).

Bawab, S.E., Usta, J., Roddy, P., et al. Substrate specificty of rat brain ceramidase. J Lipid Res 43 141-148 (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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C-12 NBD-dihydro-Ceramide