Laurdan

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Structural formula
Structural formula of Laurdan
General
Surname Laurdan
other names
  • 1- (6- (Dimethylamino) -2-naphthalyl) -1-dodecanone
  • 6-dodecanoyl- N , N -dimethyl-2-naphthylamine
Molecular formula C 24 H 35 NO
Brief description

colorless solid

External identifiers / databases
CAS number 74515-25-6
PubChem 104983
Wikidata Q15426238
properties
Molar mass 353.54 g mol −1
Physical state

firmly

Melting point

88 ° C

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Laurdan is a fluorescent dye that is used to study lipid rafts in cell membranes .

properties

Laurdan is used for staining areas of cell membranes containing cholesterol ( lipid rafts ). Laurdan has a solvatochromic effect and changes its color according to the proportion of water molecules in its environment.

Geometry of Laurdan

Laurdan consists of a lauric acid component esterified with a naphthalene . Due to a partial charge separation between the 2-dimethylamine and the 6- carbonyl group , the naphthalene group has a transition dipole moment , which increases when excited and causes the rearrangement of the molecules of the surrounding solvent . This creates the fluorescence . The rearrangement of the surrounding solvent requires energy, which is obtained from the excited state of the fluorescent dye and manifests itself in a red shift of the emission spectrum in aqueous (polar) solvents, in contrast to a blue shift in non- polar solvents . Laurdan has an emission maximum of 440 nm in the gel phase and 490 nm in the liquid phase in the cell membrane . This spectral shift is caused by relaxation , depending on the orientation of the laurdane and the rearrangement of the surrounding solvent molecules.

Applications

CHO cells stained with Laurdan

Laurdan can be applied to cells in cell culture . The storage of laurdan in areas of the cell membrane allows conclusions to be drawn about its composition.

history

Laurdan was first synthesized in 1979 by Gregorio Weber . His dissertation with the title “Fluorescence of Riboflavin, Diaphorase and Related Substances” was one of the beginnings of fluorescence spectroscopy of biomolecules. Laurdan was an alternative to dye- labeled lipids , which often showed unspecific interactions between the dye and the cell membrane. Laurdan was originally designed as a dipole relaxation dye for cell membranes.

Web links

Commons : Laurdan  - collection of images, videos and audio files

Individual evidence

  1. ↑ a b c d e data sheet 6-Dodecanoyl-N, N-dimethyl-2-naphthylamine from Sigma-Aldrich , accessed on April 14, 2014 ( PDF ).
  2. ↑ T Para Sassi, Gratton E., Levi M .: Two-photon fluorescence microscopy of laurdan generalized polarization domains in model and natural membranes . In: Biophys. J . 72, No. 6, 1997, pp. 2413-2429. bibcode : 1997BpJ .... 72.2413P . doi : 10.1016 / S0006-3495 (97) 78887-8 . PMID 9168019 . PMC 1184441 (free full text).
  3. ↑ DM Owen, Neil. MA, Magee AI: Optical techniques for imaging membrane lipid microdomains in living cells . In: Cell Dev. Biol . 18, No. 5, 2007, pp. 591-598. doi : 10.1016 / j.semcdb.2007.07.011 .
  4. ↑ LA Bagatolli: To see or not to see: lateral organization of biological membranes and fluorescence microscopy . In: Biochim. Biophys. Acta . 1758, No. 10, 2006, pp. 1451-1456. doi : 10.1016 / j.bbamem.2006.05.019 .
  5. ↑ T. Parasassi, G. De Stasio, E. Gratton: Phase fluctuation in phospholipid membranes revealed by Laurdan fluorescence . In: Biophys. J . 57, No. 6, 1990, pp. 1179-1186. bibcode : 1990BpJ .... 57.1179P . doi : 10.1016 / S0006-3495 (90) 82637-0 . PMID 2393703 . PMC 1280828 (free full text).
  6. ^ LJ Pike: Rafts defined: a report on the Keystone Symposium on Lipid Rafts and Cell Function . In: J. Lipid Res . 47, No. 7, 2006, pp. 1597-1598. doi : 10.1194 / jlr.E600002-JLR200 . PMID 16645198 .
  7. ^ SA Sanchez, MA Tricerri, E. Gratton: Laurdan generalized polarization: from cuvette to microscope . In: Modern Research and Educational Topics in Microscopy . 2007, pp. 1007-1014.
  8. ^ SA Gratton, MA Tricerri, E. Gratton .: Laurdan generalized polarization fluctuations measures membrane packing micro-heterogeneity in vivo . In: Proc. Natl. Acad. Sci. USA . 109, No. 19, 2012, pp. 7314-7319. bibcode : 2012PNAS..109.7314S . doi : 10.1073 / pnas.1118288109 . PMID 22529342 . PMC 3358851 (free full text).
  9. ↑ P. Schneckenburger, M. Wagner, H. Schneckenburger .: Fluorescence imaging of membrane dynamics in living cells . In: J. Biomed . 15, No. 4, 2010, p. 6017. bibcode : 2010JBO .... 15d6017W . doi : 10.1117 / 1.3470446 .
  10. ↑ P. Jurkiewicz, L. Cwiklik, P. Jungwirth, M. Hof: Lipid hydration and mobility: an interplay between fluorescence solvent relaxation experiments and molecular dynamics simulations. In: Biochemistry. Volume 94, Number 1, January 2012, pp. 26-32, ISSN  1638-6183 . doi : 10.1016 / j.biochi.2011.06.027 . PMID 21740953 .
  11. ↑ M Ingelmo-Torres, Gaus, K., Herms, A., Gonzalez-Moreno, E., Kassan, A .: Triton X-100 promotes cholesterol-dependent condensation of the plasma membrane . In: Biochem. J . 420, 2009, pp. 373-381. doi : 10.1042 / BJ20090051 .
  12. ↑ Use of Laurdan's fluorescence intensity and polarization to distinguish between changes in membrane fluidity and phospholipid order . In: Biochim Biophys Acta . 1565, 2002, p. 123. PMID 12225860 .
  13. ↑ LM Brignac-Huber, Reed, JR., Eyer, MK., Backes, WL .: Relationship between CYP1A2 Localization and Lipid Microdomain Formation as a Function of Lipid Composition . In: Drug Metab Dispos . 41 (11), 2013, pp. 1896-1905. doi : 10.1124 / dmd.113.053611 . PMID 23963955 .
  14. ^ A b David M. Jameson: Gregorio Weber, 1916-1997: A Fluorescent Lifetime. In: Biophysical Journal (1998), Volume 75, Issue 1, pp. 419-421. doi : 10.1016 / S0006-3495 (98) 77528-9 .
  15. ↑ Alexander P Demchenko, Yves Mély, Guy Duportail, Andrey S. Klymchenko: Monitoring Biophysical Properties of Lipid Membranes by Environment-Sensitive Fluorescent Probes . In: Biophysical Journal . 96, No. 9, May 6, 2009, pp. 3461-3470. doi : 10.1016 / j.bpj.2009.02.012 .
  16. ↑ G. Weber, FJ Farris: Synthesis and spectral properties of a hydrophobic fluorescent probe: 6 propionyl-2- (dimethylamino) naphthalene . In: Biochemistry . 18, 1979, pp. 3075-3078.
  17. ^ RB Macgregor, G. Weber: Estimation of the polarity of the protein interior by optical spectroscopy . In: Nature . 319, 1986, pp. 70-73.