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C12 NBD Ceramide | CAS 202850-01-9
| Catalog Number | A18-0060 |
| Category | Fluorescent Enzyme Substrates |
| Molecular Formula | C36H61N5O6 |
| Molecular Weight | 659.90 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
C12 NBD Ceramide is a fluorescently labeled ceramide containing a nitrobenzoxadiazole (NBD) moiety that enables real-time visualization of sphingolipid transport, partitioning, and metabolism. Its hydrophobic C12 acyl chain allows efficient incorporation into lipid bilayers while maintaining native-like ceramide behavior. The NBD fluorophore provides strong, environment-sensitive fluorescence for monitoring lipid trafficking across membranes in live-cell and in vitro systems. C12 NBD Ceramide is widely employed in fluorescence microscopy, lipid diffusion analysis, and biophysical studies of membrane organization, serving as an essential tool for exploring dynamic ceramide biology and intermembrane lipid exchange.
Chemical Information
Product Specification
Application
| Synonyms | N-[12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]dodecanoyl]-D-erythro-sphingosine; C12-NBD Ceramide; N-Dodecanoyl-NBD-D-erythro-sphingosine; N-(NBD-Aminolauroyl)ceramide; N-C12-NBD-D-erythro-Sphingosine; N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-dodecanamide |
| Purity | >99% |
| Shelf Life | 1 Year |
| IUPAC Name | N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]-12-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]dodecanamide |
| Canonical SMILES | CCCCCCCCCCCCCC=CC(C(CO)NC(=O)CCCCCCCCCCCNC1=CC=C(C2=NON=C12)[N+](=O)[O-])O |
| InChI | 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 |
| InChIKey | SNOJCYCOPNIGIK-ULETYAGTSA-N |
| Solubility | Soluble in Chloroform, DMF, DMSO, Ethanol |
| Density | 1.103±0.06 g/cm3 (Predicted) |
| Appearance | Yellow to Orange Liquid |
| Melting Point | 92-93°C |
| Storage | Store at -20°C |
C12 NBD Ceramide is a synthetic analog of ceramide, a family of lipid molecules that play crucial roles in cell membrane structure and cellular signaling pathways. This analog includes a fluorescent group, 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD), which is linked to the fatty acid chain of ceramide, making it a unique tool for researching ceramide dynamics and functions within biological systems. The inclusion of the NBD group allows researchers to visually track the distribution and localization of ceramides in live cells and tissues using fluorescence microscopy.
One key application of C12 NBD Ceramide is in the study of sphingolipid metabolism. Ceramides are central in the sphingolipid metabolic pathway, and their levels are associated with various cellular processes including apoptosis, differentiation, and proliferation. C12 NBD Ceramide helps researchers visualize these processes by allowing the tracing of ceramide distribution, thus providing insights into the regulation of sphingolipid metabolism and its implications in health and disease.
Another significant application of C12 NBD Ceramide is in apoptosis research. Ceramides are known to promote apoptosis, a form of programmed cell death, which is crucial for maintaining cellular homeostasis. By using C12 NBD Ceramide, scientists can monitor the role and movement of ceramides during apoptosis, thereby contributing to the understanding of how dysregulation in ceramide levels could lead to pathological conditions like cancer or neurodegenerative diseases.
Additionally, C12 NBD Ceramide is employed in membrane biophysics studies. The compound’s ability to integrate into cell membranes and its fluorescent properties make it invaluable for examining membrane dynamics and the biophysical properties of lipid bilayers. Researchers can use it to study how ceramides affect membrane curvature, fluidity, and permeability, providing essential insights into membrane-related processes such as signal transduction and vesicle trafficking.
Finally, C12 NBD Ceramide is a valuable tool in the development of therapeutic strategies targeting ceramide-associated diseases. It serves as a model compound to test how alterations in ceramide levels can modulate disease pathways, thus aiding in the design of interventions for conditions like insulin resistance, cardiovascular diseases, and cancer. By understanding the mechanism through which ceramides contribute to disease pathology, researchers can develop targeted therapies that modulate ceramide metabolism or signaling pathways.
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