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C-12 NBD-dihydro-Ceramide
Cayman Chemical Item Number 10008097
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.
Synonyms N-C12-NBD-D-erythro-dihydro-Sphingosine
Formal Name N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)heptadecyl]-12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-dodecanamide
CAS Number 474943-05-0
Molecular Formula C36H63N5O6
Formula Weight 661.9
Formulation A solution in chloroform:ethanol (1:1)
Purity ≥98%
λmax 229, 333, 465 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES OC[C@H](NC(CCCCCCCCCCCNC1=CC=C([N+]([O-])=O)C2=NON=C12)=O)[C@H](O)CCCCCCCCCCCCCCC
InCHI Code 1S/C36H63N5O6/c1-2-3-4-5-6-7-8-9-10-12-15-18-21-24-33(43)31(29-42)38-34(44)25-22-19-16-13-11-14-17-20-23-28-37-30-26-27-32(41(45)46)36-35(30)39-47-40-36/h26-27,31,33,37,42-43H,2-25,28-29H2,1H3,(H,38,44)/t31-,33+/m0/s1
InCHI Key STPDREBSVHTICB-CQTOTRCISA-N |