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Bodipy C12-Ceramide | CAS 1246355-58-7
| Catalog Number | F01-0046 |
| Category | BODIPY |
| Molecular Formula | C42H70N3O3F2 |
| Molecular Weight | 713.83 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
Bodipy C12-Ceramide is a fluorescent sphingolipid analog incorporating a boron-dipyrromethene (BODIPY) fluorophore within the C12 acyl chain, providing bright and photostable emission properties. Its close resemblance to native ceramide allows accurate visualization of sphingolipid trafficking, membrane microdomain localization, and lipid metabolism in real time. The molecule’s balanced hydrophobicity ensures smooth incorporation into lipid bilayers without altering membrane integrity, making it a powerful probe for confocal microscopy and live-cell imaging. Bodipy C12-Ceramide supports detailed analyses of sphingolipid signaling, membrane dynamics, and lipid raft behavior in both artificial and biological systems.
Chemical Information
Product Specification
Application
Computed Properties
| Synonyms | BODIPY-C12 Ceramide; N-[11-(dipyrrometheneboron difluoride)undecanoyl]-D-erythro-sphingosine |
| Purity | ≥98% |
| Shelf Life | 1 Year |
| IUPAC Name | 11-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)-N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]undecanamide |
| Canonical SMILES | [B-]1(N2C(=CC(=C2C(=C3[N+]1=C(C=C3C)C)CCCCCCCCCCC(=O)NC(CO)C(C=CCCCCCCCCCCCCC)O)C)C)(F)F |
| InChI | InChI=1S/C42H70BF2N3O3/c1-6-7-8-9-10-11-12-13-14-15-19-22-25-28-39(50)38(32-49)46-40(51)29-26-23-20-17-16-18-21-24-27-37-41-33(2)30-35(4)47(41)43(44,45)48-36(5)31-34(3)42(37)48/h25,28,30-31,38-39,49-50H,6-24,26-27,29,32H2,1-5H3,(H,46,51)/b28-25+/t38-,39+/m0/s1 |
| InChIKey | NGWZKZIJSBUOIZ-BOOOSZIVSA-N |
| Appearance | Dark Orange to Red Solid |
| Melting Point | >67°C (dec.) |
| Excitation | 505 nm |
| Emission | 540 nm |
| Storage | Store at -20°C |
Bodipy C12-Ceramide, a fluorescent lipid probe, is employed in diverse scientific research endeavors. Below are the key applications of Bodipy C12-Ceramide:
Cellular Imaging: In the realm of fluorescence microscopy, Bodipy C12-Ceramide plays a pivotal role in unraveling the dynamics of ceramide, a pivotal lipid signal within cells. By fluorescently labeling ceramide with the Bodipy dye, researchers are able to visually track its localization and movements within live cells in real-time. This aids in comprehending the intricate role of ceramide in pivotal cellular processes like apoptosis, cell growth, and stress responses.
Membrane Dynamics Studies: Delving into lipid membrane behavior and organization, Bodipy C12-Ceramide emerges as a critical compound for studying phenomena like lipid raft formation, membrane fusion, and lipid-protein interactions. This deep dive into membrane dynamics facilitates a better understanding of membrane integrity and cell signaling pathways, shedding light on the intricate mechanisms governing cellular processes.
Lipid Metabolism Research: A key tool for exploring lipid metabolism and ceramide-related pathways, Bodipy C12-Ceramide serves as a doorway to investigating the synthesis, metabolism, and regulation of ceramide within the cellular milieu. This exploration is crucial for unraveling the biochemical foundations of various diseases, including metabolic disorders and cancer, offering insights into pathways that influence cellular health and disease progression.
Drug Screening and Development: Within the realm of pharmaceutical research, Bodipy C12-Ceramide finds utility in high-throughput screening of compounds that modulate ceramide pathways. By closely monitoring changes in ceramide dynamics, researchers can pinpoint potential therapeutic agents targeting sphingolipid metabolism. This application holds immense value in the development of drugs aimed at treating maladies linked to ceramide dysregulation, such as neurodegenerative diseases and cancer.
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 27 |
| Exact Mass | 713.5478296 g/mol |
| Monoisotopic Mass | 713.5478296 g/mol |
| Topological Polar Surface Area | 77.5Ų |
| Heavy Atom Count | 51 |
| Formal Charge | 0 |
| Complexity | 1140 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| 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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