
C6 NBD Glucosylceramide | CAS 94885-03-7
| Catalog Number | A16-0047 |
| Category | Lipid Fluorescent Probes |
| Molecular Formula | C36H59N5O11 |
| Molecular Weight | 737.88 |
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Product Introduction
C6 NBD Glucosylceramide is a glycosphingolipid analog bearing a β-glucose headgroup and a short acyl chain tagged with an NBD fluorophore, designed for monitoring glucosylceramide metabolism and intracellular transport. Its fluorescent label enables sensitive tracking of glycosphingolipid trafficking in live cells, while the short chain improves solubility and integration into membranes. This molecule serves as an essential probe for studying glucosylceramide synthase activity, vesicular sorting, and glycosphingolipid dynamics. C6 NBD Glucosylceramide is particularly valuable for investigating how glucosylation affects lipid mobility, curvature, and compartmentalization within biological membranes.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | N-hexanoyl-NBD-Glucosylceramide; N-[(1S,2R,3E)-1-[(β-D-glucopyranosyloxy)methyl]-2-hydroxy-3-heptadecen-1-yl]-6-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-hexanamide |
| Purity | ≥98% |
| Shelf Life | 1 Year |
| IUPAC Name | N-[(E,2S,3R)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]-6-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanamide |
| SMILES | CCCCCCCCCCCCCC=CC(C(COC1C(C(C(C(O1)CO)O)O)O)NC(=O)CCCCCNC2=CC=C(C3=NON=C23)[N+](=O)[O-])O |
| InChI | InChI=1S/C36H59N5O11/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-28(43)26(24-50-36-35(47)34(46)33(45)29(23-42)51-36)38-30(44)19-16-14-17-22-37-25-20-21-27(41(48)49)32-31(25)39-52-40-32/h15,18,20-21,26,28-29,33-37,42-43,45-47H,2-14,16-17,19,22-24H2,1H3,(H,38,44)/b18-15+/t26-,28+,29+,33+,34-,35+,36+/m0/s1 |
| InChIKey | ZYEQNDHFYIPTAY-YAIFWNLCSA-N |
| Appearance | Solid Powder |
Product Specification
| Storage | Store at -20°C |
Application
C6 NBD Glucosylceramide is an NBD (7-nitrobenz-2-oxa-1,3-diazole) fluorescent glucosylceramide analog designed for lipid imaging and membrane-associated fluorescence studies. Its amphiphilic glycolipid structure supports incorporation into lipid environments, while the NBD fluorophore enables visualization with common fluorescence microscopy and flow cytometry workflows using blue-light excitation and green emission. This reagent is frequently used to track glycolipid trafficking, membrane partitioning, and NBD-labeled lipid behavior in cell-based and biomaterials-related experiments.
1. Glycolipid Trafficking Studies
C6 NBD Glucosylceramide is used to monitor intracellular movement and redistribution of glucosylceramide-like lipids in cell biology workflows. Researchers incorporate the NBD-labeled glycolipid into cell culture systems to follow how glycosphingolipid analogs traffic through membrane compartments, enabling time-resolved fluorescence imaging of lipid dynamics. The NBD tag provides a convenient readout for comparing uptake kinetics and relative localization changes under different experimental conditions, including perturbations that alter lipid processing or membrane organization.
2. Membrane Partitioning And Uptake
C6 NBD Glucosylceramide supports studies of membrane association and lipid uptake by visualizing how an amphiphilic glycolipid analog partitions into cellular membranes. In microscopy and flow cytometry experiments, the NBD fluorescence signal is used to quantify relative incorporation into membrane fractions and to compare labeling intensity across experimental groups. This application is commonly used in chemical biology and biomaterials research to evaluate how lipid composition, membrane environment, or formulation conditions influence glycolipid analog distribution.
3. Lipid Processing Assays
C6 NBD Glucosylceramide is applied in fluorescence-based assays that probe glycolipid processing and related lipid remodeling events through changes in NBD fluorescence distribution over time. Researchers use the reagent as a fluorescent lipid substrate analog to generate dynamic readouts in cell lysates or intact-cell formats, where shifts in fluorescence localization can reflect altered lipid handling. The workflow is particularly useful for screening experimental conditions that modulate lipid metabolism pathways, since the NBD label provides a straightforward optical signal for monitoring temporal changes.
4. Biomaterials Surface Labeling
C6 NBD Glucosylceramide is also used to functionalize or label lipid-containing biomaterial surfaces and lipid coatings for fluorescence tracking of membrane-like layers. Materials scientists and biointerface researchers incorporate the NBD-glucosylceramide analog into supported lipid systems or lipid-modified substrates to visualize adsorption, spreading, and stability of glycolipid-containing layers. The resulting fluorescence enables qualitative and semi-quantitative assessment of surface coverage and spatial uniformity using standard fluorescence imaging instrumentation.
Computed Properties
| XLogP3 | 5.7 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 26 |
| Exact Mass | 737.42110772 g/mol |
| Monoisotopic Mass | 737.42110772 g/mol |
| Topological Polar Surface Area | 246Ų |
| Heavy Atom Count | 52 |
| Formal Charge | 0 |
| Complexity | 1020 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 7 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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