title: Red emitting neutral fluorescent glycoconjugates for membrane optical imaging.
abstract: 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.
authors: Laboratoire de Chimie Organique et Bioorganique, ICBMS, INSA Lyon , Bât. J. Verne, 20 Avenue A. Einstein, 69621 Villeurbanne Cedex, France.
authors: Sébastien
authors: S
authors: Redon
authors: Julien
authors: J
authors: Massin
authors: Sandrine
authors: S
authors: Pouvreau
authors: Evelien
authors: E
authors: De Meulenaere
authors: Koen
authors: K
authors: Clays
authors: Yves
authors: Y
authors: Queneau
authors: Chantal
authors: C
authors: Andraud
authors: Agnès
authors: A
authors: Girard-Egrot
authors: Yann
authors: Y
authors: Bretonnière
authors: Stéphane
authors: S
authors: Chambert
mesh_terms: D000818:Animals; D002462:Cell Membrane / Q000378:metabolism*; D003116:Color; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry*; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D018613:Microscopy, Confocal; D015394:Molecular Structure; D018482:Muscle, Skeletal / Q000166:cytology*; D061848:Optical Imaging
chemical_list: D005456:Fluorescent Dyes; D006001:Glycoconjugates