Laurdan

Laurdan
Laurdan chain structure
Names
Preferred IUPAC name
1-[6-(Dimethylamino)naphthalen-2-yl]dodecan-1-one
Other names
Laurdan
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
    Key: JHDGGIDITFLRJY-UHFFFAOYSA-N
  • CCCCCCCCCCCC(=O)c1ccc2cc(ccc2c1)N(C)C
Properties
C24H35NO
Molar mass 353.55
Appearance Colourless solid
Melting point 88 °C (190 °F; 361 K) (lit.)
DMF: soluble; acetonitrile: soluble, methanol: soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Laurdan is an organic compound which is used as a fluorescent dye when applied to fluorescence microscopy.[1][2] It is used to investigate membrane qualities of the phospholipid bilayers of cell membranes.[3][4][5][6] One of its most important characteristics is its sensitivity to membrane phase transitions as well as other alterations to membrane fluidity such as the penetration of water.[7][8]

  1. ^ Parasassi, T; Gratton E.; Levi M. (1997). "Two-photon fluorescence microscopy of laurdan generalized polarization domains in model and natural membranes". Biophys. J. 72 (6): 2413–2429. Bibcode:1997BpJ....72.2413P. doi:10.1016/S0006-3495(97)78887-8. PMC 1184441. PMID 9168019.
  2. ^ Owen, D. M.; Neil. M. A.; Magee A. I. (2007). "Optical techniques for imaging membrane lipid microdomains in living cells". Seminars in Cell & Developmental Biology. 18 (5): 591–598. doi:10.1016/j.semcdb.2007.07.011. PMID 17728161.
  3. ^ Bagatolli, L. A. (2006). "To see or not to see: lateral organization of biological membranes and fluorescence microscopy". Biochim. Biophys. Acta. 1758 (10): 1451–1456. doi:10.1016/j.bbamem.2006.05.019. PMID 16854370.
  4. ^ Parasassi, T.; G. De Stasio; E. Gratton (1990). "Phase fluctuation in phospholipid membranes revealed by Laurdan fluorescence". Biophys. J. 57 (6): 1179–1186. Bibcode:1990BpJ....57.1179P. doi:10.1016/S0006-3495(90)82637-0. PMC 1280828. PMID 2393703.
  5. ^ Pike, L. J. (2006). "Rafts defined: a report on the Keystone Symposium on Lipid Rafts and Cell Function". J. Lipid Res. 47 (7): 1597–1598. doi:10.1194/jlr.E600002-JLR200. PMID 16645198.
  6. ^ Sanchez, S. A.; M. A. Tricerri; E. Gratton (2007). "Laurdan generalized polarization: from cuvette to microscope". Modern Research and Educational Topics in Microscopy: 1007–1014.
  7. ^ Gratton, S. A.; M. A. Tricerri, E. Gratton. (2012). "Laurdan generalized polarization fluctuations measures membrane packing micro-heterogeneity in vivo". Proc. Natl. Acad. Sci. USA. 109 (19): 7314–7319. Bibcode:2012PNAS..109.7314S. doi:10.1073/pnas.1118288109. PMC 3358851. PMID 22529342.
  8. ^ Schneckenburger, P.; M. Wagner; H. Schneckenburger. (2010). "Fluorescence imaging of membrane dynamics in living cells". J. Biomed. 15 (4): 046017–046017–5. Bibcode:2010JBO....15d6017W. doi:10.1117/1.3470446. PMID 20799819.