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C6 NBD Sphingomyelin | CAS 94885-04-8
| Catalog Number | A16-0044 |
| Category | Lipid Fluorescent Probes |
| Molecular Formula | C35H61N6O9P |
| Molecular Weight | 740.87 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
C6 NBD Sphingomyelin is a fluorescently labeled sphingophospholipid that retains the structural features of native sphingomyelin while introducing an NBD fluorophore for high-sensitivity detection. The short acyl chain provides superior solubility and enables dynamic membrane incorporation without altering sphingomyelin’s natural ordering effect. This compound is widely used to track sphingomyelin distribution, degradation, and cholesterol-dependent microdomain organization. C6 NBD Sphingomyelin allows researchers to visualize sphingomyelin turnover, lipid exchange, and vesicular dynamics in both model and cellular systems, offering an essential fluorescent probe for membrane biophysics and lipid trafficking research.
Chemical Information
Product Specification
Application
| Synonyms | N-hexanoyl-NBD Sphingosylphosphorylcholine; (7S)-4-hydroxy-7-[(1R,2E)-1-hydroxy-2-hexadecen-1-yl]-N,N,N-trimethyl-14-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-9-oxo-3,5-dioxa-8-aza-4-phosphatetradecan-1-aminium, 4-oxide inner salt; N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-sphingosine-1-phosphocholine |
| Purity | ≥98% |
| Shelf Life | 1 Year |
| IUPAC Name | [(E,2S,3R)-3-hydroxy-2-[6-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanoylamino]octadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate |
| Canonical SMILES | CCCCCCCCCCCCCC=CC(C(COP(=O)([O-])OCC[N+](C)(C)C)NC(=O)CCCCCNC1=CC=C(C2=NON=C12)[N+](=O)[O-])O |
| InChI | InChI=1S/C35H61N6O9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-18-21-32(42)30(28-49-51(46,47)48-27-26-41(2,3)4)37-33(43)22-19-17-20-25-36-29-23-24-31(40(44)45)35-34(29)38-50-39-35/h18,21,23-24,30,32,42H,5-17,19-20,22,25-28H2,1-4H3,(H2-,36,37,39,43,46,47)/b21-18+/t30-,32+/m0/s1 |
| InChIKey | YDBDYTGWMRUUSN-DYTRJAOYSA-N |
| Appearance | Solid Powder |
| Storage | Store at -20°C |
C6 NBD sphingomyelin is a specialized derivative of sphingomyelin, a type of sphingolipid found abundantly in the membranes of mammalian cells, especially in the myelin sheath that insulates nerve fibers. What sets C6 NBD sphingomyelin apart is its chemical modification with the incorporation of a fluorescent group known as C6 nitrobenzoxadiazole (C6 NBD). This fluorescent tag makes it an invaluable tool in studying various biological processes due to its ability to emit fluorescence under appropriate conditions, facilitating real-time tracking and visualization in biological experiments.
One of the key applications of C6 NBD sphingomyelin is in the study of sphingomyelin metabolism. Researchers can incorporate this fluorescent sphingomyelin into cell membranes to monitor the enzymatic conversion processes involving sphingomyelin, such as its hydrolysis by sphingomyelinase enzymes. This is crucial for understanding diseases like Niemann-Pick disease, where sphingomyelin metabolism is disrupted. The fluorescent nature of C6 NBD sphingomyelin enables precise tracking of these biochemical pathways, providing insights into physiological and pathological conditions.
Another significant application is in the investigation of lipid transport mechanisms. C6 NBD sphingomyelin can be used as a reporter molecule to study the intracellular and intercellular movement of lipids. It aids in elucidating the pathways by which sphingomyelin and other lipids are distributed among various cell organelles and transported to different cellular destinations. Understanding these pathways is essential for unraveling the complexities of lipid-related disorders and for developing targeted therapeutic strategies.
C6 NBD sphingomyelin also plays a critical role in membrane dynamics studies. By integrating into cellular membranes, this fluorescent lipid can help visualize membrane fluidity, phase separation, and the behavior of lipid rafts. These studies are vital for comprehending how membrane composition and organization affect cell signaling, protein trafficking, and membrane-associated processes. Furthermore, the fluorescent properties of C6 NBD sphingomyelin facilitate advanced imaging techniques, including fluorescence microscopy and spectroscopy, enabling detailed exploration of membrane architecture and function.
Finally, C6 NBD sphingomyelin is instrumental in drug delivery research, particularly in assessing the efficacy and dynamics of sphingomyelin-based nanocarriers. By tagging these carriers with C6 NBD sphingomyelin, researchers can visualize and quantify the cellular uptake, distribution, and release of therapeutic agents within the target cells. This application is crucial for developing novel drug delivery systems that optimize therapeutic efficacy while minimizing adverse effects, ultimately contributing to more effective treatments for various diseases.
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