Red Emitting Neutral Fluorescent Glycoconjugates for Membrane Optical Imaging.
Bioconjugate Chem.. 2014-03-17; 25(4): 773-787
DOI: 10.1021/bc500047r
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1. Bioconjug Chem. 2014 Apr 16;25(4):773-87. doi: 10.1021/bc500047r. Epub 2014
Mar 17.
Red emitting neutral fluorescent glycoconjugates for membrane optical imaging.
Redon S(1), Massin J, Pouvreau S, De Meulenaere E, Clays K, Queneau Y, Andraud
C, Girard-Egrot A, Bretonnière Y, Chambert S.
Author information:
(1)Laboratoire de Chimie Organique et Bioorganique, ICBMS, INSA Lyon , Bât. J.
Verne, 20 Avenue A. Einstein, 69621 Villeurbanne Cedex, France.
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.
DOI: 10.1021/bc500047r
PMID: 24528385 [Indexed for MEDLINE]