C6 NBD Sphingomyelin

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C6 NBD Sphingomyelin

C6 NBD Sphingomyelin | 94885-04-8

Catalog Number A16-0044
Category Lipid Fluorescent Probes
Molecular Formula C35H61N6O9P
Molecular Weight 740.87
Catalog Number Size Price Quantity
A16-0044 -- $--

Product Introduction

C6 NBD sphingomyelin is a sphingomyelin derivative that is tagged with a fluorescent group C6 nitrobenzoxadiazole (C6 NBD). Sphingomyelin naturally exists in mammalian cell membranes, especially membranes of the myelin sheath. C6 NBD sphingomyelin has been used to study the metabolism and transport of sphingomyelins.

Chemical Information

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
InChI Key YDBDYTGWMRUUSN-DYTRJAOYSA-N
Appearance Solid Powder
  • Product Specification
  • Application
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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