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Bioinspired Fluorescent Dyes Based on a Conformationally Locked Chromophore of the Fluorescent Protein Kaede
Author(s) -
Baleeva Nadezhda S.,
Myannik Ksenia A.,
Yampolsky Ilia V.,
Baranov Mikhail S.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500721
Subject(s) - chromophore , fluorescence , chemistry , photochemistry , quantum yield , green fluorescent protein , optics , biochemistry , physics , gene
A novel class of fluorescent dyes based on the conformationally locked heterocyclic core of the chromophore of the fluorescent protein Kaede was discovered. Introduction of a single conformational lock at the benzylidene fragment of the Kaede chromophore resulted in an increase in the fluorescence quantum yield (FQY) by one order of magnitude and a redshift of ca. 60 nm in the emission spectrum. Imposing the second lock at the ethylene fragment of the Kaede chromophore provided a further increase in the FQY. Locked analogues demonstrated bright and redshifted emission in a broad range of solvents, which makes them good candidates for a wide spectrum of fluorescent‐labeling applications.