4-Amino-N-adamantylphthalimide (1) is a dye with moderate absorptivity (in CH3CN ε363 = 4200 M−1 cm−1) and high quantum yield of fluorescence (ΦF = 0.15–0.80) that exhibits fluorosolvatochromic properties. The dye can be excited at 405 nm and the position of fluorescence maximum and the Stokes shift are well correlated with the ET(30) parameter. The excitation in the near-visible part of the spectrum and low cytotoxicity allow use of the dye in live cell microscopy. Due to its amphiphilic character, the dye stains artificial membranes in liposomes. Using confocal microscopy on two human cancer cell lines, we have shown that 1 stains primarily intracellular lipid droplets. Colocalization experiments with different organelle markers indicated that 1 additionally stains mitochondrial membranes. The fluorosolvatochromism of 1 allows the simultaneous visualization of mitochondria and intracellular lipid droplets in two separate emission channels, which has a potential use in cells and tissues exhibiting intense oxidative metabolism of lipids.
ASJC Scopus subject areas
- Electronic, Optical and Magnetic Materials
- Condensed Matter Physics
- Surfaces, Coatings and Films
- Metals and Alloys
- Electrical and Electronic Engineering
- Materials Chemistry