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NBD Sphingosine | CAS 1449370-25-5
| Catalog Number | A16-0055 |
| Category | Lipid Fluorescent Probes |
| Molecular Formula | C24H39N5O5 |
| Molecular Weight | 477.60 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
NBD sphingosine is a sphingosine derivative that is tagged with a fluorescent group nitrobenzoxadiazole (NBD). It has been used to study the cellular localization and metabolism of sphingosine in HeLa cells. NBD sphingosine also inhibits proliferation of HCT116, PC3, HEK293T, and HFE-145 cells (IC50 = 25.6, 40.5, 10.4, and 12.5 μM, respectively).
Chemical Information
Product Specification
Application
Computed Properties
Patents
| Related CAS | 799268-47-6 |
| Synonyms | omega(7-nitro-2-1,3-benzoxadiazol-4-yl)(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol; D-erythro-Sphingosine-N-NBD |
| Purity | ≥95% |
| IUPAC Name | 2-amino-18-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]octadec-4-ene-1,3-diol |
| Canonical SMILES | C1=C(C2=NON=C2C(=C1)[N+](=O)[O-])NCCCCCCCCCCCCCC=CC(C(CO)N)O |
| InChI | InChI=1S/C24H39N5O5/c25-19(18-30)22(31)14-12-10-8-6-4-2-1-3-5-7-9-11-13-17-26-20-15-16-21(29(32)33)24-23(20)27-34-28-24/h12,14-16,19,22,26,30-31H,1-11,13,17-18,25H2/b14-12+/t19-,22+/m0/s1 |
| InChIKey | MNFOPKRTMFDMJV-HCEDEFRUSA-N |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 674.7±65.0 °C at 760 mmHg |
| Storage | Store at -20°C |
NBD Sphingosine, a fluorescently labeled sphingolipid analog, plays a pivotal role in various research endeavors, especially in deciphering cellular and molecular intricacies. Here are four key applications of NBD Sphingosine:
Cell Membrane Studies: Delving into the dynamics and organization of sphingolipids within cell membranes, NBD Sphingosine becomes a beacon for researchers. Its fluorescent characteristics illuminate the localization and trafficking of sphingolipids, enabling visualization via fluorescence microscopy. This application sheds light on membrane microdomains, unraveling their significance in cellular signaling and homeostasis.
Sphingolipid Metabolism: Employed as a probe for delving into sphingolipid metabolic pathways, NBD Sphingosine aids in deciphering the intricate enzymatic activities governing sphingolipid biosynthesis and catabolism. By tracing its integration into metabolic intermediates, scientists can untangle the functions of specific enzymes like sphingosine kinases. This utility is indispensable in unearthing metabolic perturbations linked to diverse diseases.
Apoptosis and Cell Death Research: Serving as a versatile tool for unraveling the mysteries of apoptosis, NBD Sphingosine emerges as a vital asset. Given the pivotal role of sphingolipids in programmed cell death, its incorporation into cellular sphingolipids enables researchers to track alterations in sphingolipid levels and distribution during apoptosis. This deep dive into cellular demise furnishes valuable insights into disease progression and potential therapeutic avenues.
Drug Development and Screening: In the realm of drug discovery, NBD Sphingosine assumes a crucial role, particularly in the screening of compounds modulating sphingolipid pathways. By scrutinizing how prospective therapeutics impact NBD Sphingosine’s uptake, metabolism, or cellular dispersion, researchers can assess drug efficacy and mechanisms of action. This application forms the bedrock for the development of treatments targeting conditions like cancer and metabolic disorders.
| XLogP3 | 5.1 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 18 |
| Exact Mass | 477.29511936 g/mol |
| Monoisotopic Mass | 477.29511936 g/mol |
| Topological Polar Surface Area | 163Ų |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Complexity | 576 |
| 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 |
| Publication Number | Title | Priority Date |
|---|---|---|
| JP-WO2015156017-A1 | Method and apparatus for promoting skin penetration of cosmetic ingredients | 2014-04-10 |
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