American Chemical Society
bc500047r_si_001.pdf (7.29 MB)

Red Emitting Neutral Fluorescent Glycoconjugates for Membrane Optical Imaging

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journal contribution
posted on 2014-04-16, 00:00 authored by Sébastien Redon, Julien Massin, Sandrine Pouvreau, Evelien De Meulenaere, Koen Clays, Yves Queneau, Chantal Andraud, Agnès Girard-Egrot, Yann Bretonnière, Stéphane Chambert
A family of neutral fluorescent probes was developed, mimicking the overall structure of natural glycolipids in order to optimize their membrane affinity. Nonreducing commercially available di- or trisaccharidic structures were connected to a push–pull chromophore based on dicyanoisophorone electron-accepting group, which proved to fluoresce in the red region with a very large Stokes shift. This straightforward synthetic strategy brought structural variations to a series of probes, which were studied for their optical, biophysical, and biological properties. The insertion properties of the different probes into membranes were evaluated on a model system using the Langmuir monolayer balance technique. Confocal fluorescence microscopy performed on muscle cells showed completely different localizations and loading efficiencies depending on the structure of the probes. When compared to the commercially available ANEPPS, a family of commonly used membrane imaging dyes, the most efficient probes showed a similar brightness, but a sharper pattern was observed. According to this study, compounds bearing one chromophore, a limited size of the carbohydrate moiety, and an overall rod-like shape gave the best results.