
3-NBD-C12 Cholesterol | CAS 186833-02-3
| Catalog Number | A16-0090 |
| Category | Lipid Fluorescent Probes |
| Molecular Formula | C45H70N4O5 |
| Molecular Weight | 747.06 |
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Product Introduction
3-NBD-C12 Cholesterol is a fluorescent cholesterol analog featuring a nitrobenzoxadiazole (NBD) fluorophore, allowing for visualization in lipid research. This compound incorporates a C12 alkyl chain, enabling its integration into lipid membranes and facilitating studies of cholesterol distribution and dynamics. Its fluorescence emission properties, characterized by a green fluorescence, make it suitable for use in fluorescence microscopy and membrane trafficking assays, providing insights into the behavior of cholesterol within biological systems.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| IUPAC Name | [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 12-[methyl-(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]dodecanoate |
| SMILES | CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)CCCCCCCCCCCN(C)C5=CC=C(C6=NON=C56)[N+](=O)[O-])C)C |
| InChI | InChI=1S/C46H72N4O5/c1-32(2)17-16-18-33(3)37-22-23-38-36-21-20-34-31-35(26-28-45(34,4)39(36)27-29-46(37,38)5)54-42(51)19-14-12-10-8-7-9-11-13-15-30-49(6)40-24-25-41(50(52)53)44-43(40)47-55-48-44/h20,24-25,32-33,35-39H,7-19,21-23,26-31H2,1-6H3/t33-,35+,36+,37-,38+,39+,45+,46-/m1/s1 |
| InChIKey | MKEQHMRXIADXQQ-KLHFYLHASA-N |
| Appearance | Solid Powder |
Product Specification
| Excitation | 465 nm |
| Emission | 536 nm |
Application
3-NBD-C12 Cholesterol is a fluorescent cholesterol analog built on a NBD (7-nitrobenz-2-oxa-1,3-diazole) fluorophore and a C12 hydrophobic tail, enabling membrane-associated labeling in lipid-rich environments. In fluorescence studies, it is commonly used to track cholesterol uptake, distribution, and trafficking dynamics by monitoring NBD fluorescence in cells and model membranes. The combination of a lipid-mimetic scaffold and a compact fluorophore makes it a practical reagent for membrane imaging and lipid transport workflows.
1. Membrane Cholesterol Tracking
3-NBD-C12 Cholesterol is frequently used in cellular fluorescence microscopy to visualize cholesterol-like behavior at the plasma membrane and intracellular membrane compartments. Researchers use it to follow redistribution events during lipid perturbation experiments and to compare relative membrane association across conditions in mechanistic membrane trafficking studies. Because the probe is lipid-mimetic, it integrates into membrane environments where NBD fluorescence reports on local probe presence, supporting qualitative and semi-quantitative localization workflows.
2. Lipid Uptake And Trafficking Studies
3-NBD-C12 Cholesterol supports fluorescence-based assays designed to monitor cholesterol uptake and intracellular transport kinetics. In typical experimental workflows, the probe is added to cell cultures and fluorescence readouts are collected over time using plate readers, flow cytometry, or imaging systems to assess how treatments influence probe accumulation and movement through membrane pathways. This makes it a useful tool for chemical biology and biomembrane research where lipid transport phenotypes are evaluated using a cholesterol analog reporter.
3. Model Membrane Imaging
3-NBD-C12 Cholesterol is also used in membrane-mimetic systems such as supported lipid bilayers and liposomes to study cholesterol partitioning and membrane mixing behavior. Imaging and spectroscopy-based characterization can be performed to observe how the probe distributes within lipid phases and how compositional changes affect probe localization. This application is particularly valuable for materials and biophysical groups developing membrane-active formulations, lipid nanoparticles, or membrane-interacting biomaterials where cholesterol-like partitioning is a key design parameter.
4. Fluorescence-Based Lipid Transport Assays
3-NBD-C12 Cholesterol is employed in assay development workflows that require a fluorescent lipid reporter to quantify relative changes in membrane-associated lipid pools. Researchers commonly adapt the probe to time-resolved fluorescence measurements in multiwell formats to compare uptake efficiency or redistribution under different experimental conditions. The NBD signal provides a straightforward readout for screening lipid transport-modulating reagents and for supporting mechanistic studies of membrane lipid dynamics using fluorescence intensity as the primary output.
Computed Properties
| XLogP3 | 14.3 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 20 |
| Exact Mass | 760.55027141 g/mol |
| Monoisotopic Mass | 760.55027141 g/mol |
| Topological Polar Surface Area | 114Ų |
| Heavy Atom Count | 55 |
| Formal Charge | 0 |
| Complexity | 1290 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 8 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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