Laurdan

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Laurdan

Laurdan | 74515-25-6

Catalog Number A16-0020
Category Lipid Fluorescent Probes
Molecular Formula C24H35NO
Molecular Weight 353.55
Catalog Number Size Price Quantity
A16-0020 -- $--

Product Introduction

Laurdan is a fluorescent membrane probe that is sensitive to the phospholipid phase transitions of cell membrane. Quantitation of generalized polarization (GP) of laurdan can be used to identify phospholipid phase.

Chemical Information

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
InChI Key JHDGGIDITFLRJY-UHFFFAOYSA-N
Solubility Soluble in DMF, Acetonitrile, and Methanol
Appearance Solid Powder
  • Product Specification
  • Application
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.

Computed Properties

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

Literatures

PMIDPublication DateTitleJournal
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

Patents

Publication NumberTitlePriority 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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