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Laurdan | CAS 74515-25-6
| Catalog Number | A16-0020 |
| Category | Lipid Fluorescent Probes |
| Molecular Formula | C24H35NO |
| Molecular Weight | 353.55 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
Laurdan (6-dodecanoyl-2-dimethylaminonaphthalene) is a well-established fluorescent probe that detects changes in lipid membrane polarity and phase transitions by exhibiting environment-sensitive emission shifts. Its amphiphilic structure allows it to insert near the lipid headgroup region, where it reports on hydration and lipid packing density. Laurdan is widely used in the study of membrane phase behavior, lipid rafts, and vesicle dynamics, offering quantitative insights into bilayer order and heterogeneity. The molecule is indispensable in high-resolution fluorescence microscopy and biophysical lipid research aimed at mapping structural transitions in synthetic and biological membranes.
Chemical Information
Product Specification
Application
Computed Properties
Literatures
Patents
| Synonyms | 6-Dodecanoyl-2-dimethylaminonaphthalene; 6-Dodecanoyl-N,N-dimethyl-2-naphthylamine; N,N-Dimethyl-6-dodecanoyl-2-naphthylamine |
| Purity | ≥98% |
| Shelf Life | 1 Year |
| IUPAC Name | 1-[6-(dimethylamino)naphthalen-2-yl]dodecan-1-one |
| Canonical SMILES | CCCCCCCCCCCC(=O)C1=CC2=C(C=C1)C=C(C=C2)N(C)C |
| InChI | InChI=1S/C24H35NO/c1-4-5-6-7-8-9-10-11-12-13-24(26)22-15-14-21-19-23(25(2)3)17-16-20(21)18-22/h14-19H,4-13H2,1-3H3 |
| InChIKey | JHDGGIDITFLRJY-UHFFFAOYSA-N |
| Solubility | Soluble in DMF, Acetonitrile, and Methanol |
| Appearance | Solid Powder |
| Storage | Store at -20°C |
Laurdan, a versatile fluorescent dye utilized in the examination of cell membranes and lipid environments, boasts a wide array of applications. Here are four key applications of Laurdan:
Membrane Fluidity Analysis: Widely employed for evaluating the fluidity and phase behavior of cell membranes, Laurdan serves as a critical tool in understanding membrane dynamics. By incorporating Laurdan into lipid bilayers, researchers can meticulously analyze changes in membrane properties across varying conditions through the lens of fluorescence microscopy.
Lipid Raft Studies: Leading the charge in dissecting lipid rafts, specialized microdomains within cell membranes enriched with cholesterol and sphingolipids, Laurdan’s unique sensitivity to the lipid environment enables the visualization and characterization of these crucial domains. Delving into lipid raft dynamics is essential for unraveling the complexities of cell signaling pathways and the functionality of membrane proteins, shedding light on the intricacies of cellular communication and membrane regulation.
Cellular Imaging: Empowering fluorescence microscopy with its prowess, Laurdan plays a pivotal role in capturing real-time insights into membrane behavior within living cells and tissues. By staining cells with Laurdan, researchers can track and monitor dynamic changes in membrane properties during key processes such as endocytosis, exocytosis, and cell division. This real-time visualization of cellular responses and membrane-associated events adds a layer of depth to the study of cell behavior, offering a glimpse into the dynamic interplay within cellular membranes.
Biophysical Studies: At the forefront of biophysical exploration, Laurdan facilitates in-depth investigations into the complex interplay between lipids and proteins within cellular membranes. Leveraging cutting-edge techniques like two-photon fluorescence microscopy, scientists delve into the intricate realm of how proteins modulate membrane properties and organization. This comprehensive approach aids in unraveling the structural and functional intricacies of biomembranes and sheds light on the dynamic interactions between proteins and lipids within cellular environments, providing a foundation for understanding fundamental biological processes.
| XLogP3 | 8.1 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 12 |
| Exact Mass | 353.271864740 g/mol |
| Monoisotopic Mass | 353.271864740 g/mol |
| Topological Polar Surface Area | 20.3Ų |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Complexity | 392 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 22889622 | 2012-11-01 | Effect of the addition of alkanols of different topology to dipalmitoyl-phosphatidylcholine vesicles in the presence of gramicidin | Journal of colloid and interface science |
| 22522030 | 2012-10-01 | Interaction of gentamicin polycation with model and cell membranes | Bioelectrochemistry (Amsterdam, Netherlands) |
| 22884687 | 2012-10-01 | Use of the fluorescent probe LAURDAN to label and measure inner membrane fluidity of endospores of Clostridium spp | Journal of microbiological methods |
| 22555243 | 2012-05-03 | Elucidating membrane structure and protein behavior using giant plasma membrane vesicles | Nature protocols |
| 22406142 | 2012-04-01 | Membrane effects of lysozyme amyloid fibrils | Chemistry and physics of lipids |
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-114634553-A | Cationic peptide C9 and its application | 2022-04-27 |
| WO-2022230354-A1 | Compound, fluorochrome, kit, and cell detection method | 2021-04-26 |
| WO-2022204288-A1 | Branched tail lipid compounds and compositions for intracellular delivery of therapeutic agents | 2021-03-24 |
| WO-2022167820-A1 | Methods for measuring the redox potential of proteins | 2021-02-08 |
| WO-2022125673-A1 | Cell-penetrating peptides and peptide complexes and methods of use | 2020-12-09 |
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