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N9158

Sigma-Aldrich

N-(NBD-Aminolauroyl)ceramide

≥98%

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Synonym(s):
C12-NBD Ceramide, N-[12-[(7-Nitro-2-1,3-benzoxadiazol-4-yl)amino]dodecanoyl]-ceramide
Empirical Formula (Hill Notation):
C36H61N5O6
Molecular Weight:
659.90
MDL number:
MFCD02259239
UNSPSC Code:
12352211
PubChem Substance ID:
329818612
NACRES:
NA.77

Quality Level

200

Assay

≥98%

form

solid

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCNc1ccc([N+]([O-])=O)c2nonc12

InChI

1S/C36H61N5O6/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/h21,24,26-27,31,33,37,42-43H,2-20,22-23,25,28-29H2,1H3,(H,38,44)/b24-21+/t31-,33+/m0/s1

InChI key

SNOJCYCOPNIGIK-ULETYAGTSA-N

General description

Fluorescently labeled fatty acid sphingolipid membrane probe. NBD group excitation 460 nm, emission 534 nm.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Shaalee Dworski et al.
Biochimica et biophysica acta, 1863(2), 386-394 (2016-12-05)
Acid Ceramidase Deficiency (Farber disease, FD) is an ultra-rare Lysosomal Storage Disorder that is poorly understood and often misdiagnosed as Juvenile Idiopathic Arthritis (JIA). Hallmarks of FD are accumulation of ceramides, widespread macrophage infiltration, splenomegaly, and lymphocytosis. The cytokines involved
Cassandra Suhrland et al.
Journal of biomedical materials research. Part B, Applied biomaterials, 108(3), 1141-1156 (2019-08-25)
The bioactive sphingolipid ceramide has many important roles in cell signaling processes, particularly in signaling programmed cell death in cancer. However, ceramide levels are often impaired in multi-drug resistant and radiation resistant cancers due to the dysregulation of ceramide metabolism.
Anis Ahmad et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 31(2), 771-780 (2016-11-12)
The molecular mechanisms responsible for the development of proteinuria and glomerulosclerosis in radiation nephropathy remain largely unknown. Podocytes are increasingly recognized as key players in the pathogenesis of proteinuria in primary and secondary glomerular disorders. The lipid-modulating enzyme sphingomyelin phosphodiesterase
Paola Palumbo et al.
International journal of molecular sciences, 20(12) (2019-06-23)
The relevance of nitric oxide synthase 2 (NOS2) as a prognostic factor in Glioblastoma Multiforme (GBM) malignancy is emerging. We analyzed the effect of NOS2 inhibitor 1400W on the autophagic flux and extracellular vesicle (EV) secretion in U87MG glioma cells.
Wataru Sakamoto et al.
Journal of lipid research, 59(11), 2116-2125 (2018-08-30)
Ceramidases hydrolyze ceramides into sphingosine and fatty acids, with sphingosine being further metabolized into sphingosine-1-phosphate (S1P); thus, ceramidases control the levels of these bioactive sphingolipids in cells and tissues. Neutral ceramidase (nCDase) is highly expressed in colorectal tissues, and a

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