CAPRYDAA, an anthracene dye analog to LAURDAN: a comparative study using cuvette and microscopy

J Mater Chem B. 2020 Jan 7;8(1):88-99. doi: 10.1039/c9tb01738k. Epub 2019 Nov 26.


We synthesized an anthracene derivative with solvatochromic properties to be used as a molecular probe for membrane dynamics and supramolecular organization. A nine carbon atom acyl chain and a dimethylamino substitution were introduced at positions 2 and 6 of the anthracene ring, respectively. This derivative, 2-nonanoyl-6-(dimethylamino)anthracene (termed CAPRYDAA), is a molecular probe designed to mimic the well-known membrane probe LAURDAN's location and response in the lipid membranes. Due to the larger distance between the electron donor and acceptor groups, its absorption and emission bands are red-shifted according to the polarity of the media. The photophysical behavior of CAPRYDAA was measured in homogeneous media, synthetic bilayer and cells, both in a cuvette and in a fluorescence microscope, using one and two-photon excitation. Our results show a comparable physicochemical behavior of CAPRYDAA with LAURDAN, but with the advantage of using visible light (488 nm) as an excitation source. CAPRYDAA was also excitable by two-photon laser sources, making it easy to combine CAPRYDAA with either blue or red emission probes. In GUVs or cells, CAPRYDAA can discriminate the lipid phases and liquid-liquid phase heterogeneity. This new membrane probe shows the bathochromic properties of the PRODAN-based probes designed by Weber, overcoming the need for UV or two-photon excitation and facilitating the studies on the membrane properties using regular confocal microscopes.

Publication types

  • Comparative Study
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Naphthylamine / analogs & derivatives*
  • Animals
  • Anthracenes / chemistry*
  • Cell Membrane / chemistry*
  • Cell Membrane / ultrastructure
  • Fluorescent Dyes / chemistry*
  • Membrane Lipids / analysis
  • Mice
  • Microscopy, Fluorescence / methods*
  • NIH 3T3 Cells
  • Spectrometry, Fluorescence / methods*


  • Anthracenes
  • Fluorescent Dyes
  • Membrane Lipids
  • 2-Naphthylamine