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A Three‐Component Assembly Promoted by Boronic Acids Delivers a Modular Fluorophore Platform (BASHY Dyes)
Author(s) -
Santos Fábio M. F.,
Rosa João N.,
Candeias Nuno R.,
Carvalho Cátia Parente,
Matos Ana I.,
Ventura Ana E.,
Florindo Helena F.,
Silva Liana C.,
Pischel Uwe,
Gois Pedro M. P.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503943
Subject(s) - fluorophore , fluorescence , boronic acid , chemistry , membrane , combinatorial chemistry , hela , nile red , phototoxicity , photochemistry , fluorescein , biochemistry , cell , physics , quantum mechanics , in vitro
Abstract The modular assembly of boronic acids with Schiff‐base ligands enabled the construction of innovative fluorescent dyes [boronic acid salicylidenehydrazone (BASHY)] with suitable structural and photophysical properties for live cell bioimaging applications. This reaction enabled the straightforward synthesis (yields up to 99 %) of structurally diverse and photostable dyes that exhibit a polarity‐sensitive green‐to‐yellow emission with high quantum yields of up to 0.6 in nonpolar environments. These dyes displayed a high brightness (up to 54 000 m −1 cm −1 ). The promising structural and fluorescence properties of BASHY dyes fostered the preparation of non‐cytotoxic, stable, and highly fluorescent poly(lactide‐ co ‐glycolide) nanoparticles that were effectively internalized by dendritic cells. The dyes were also shown to selectively stain lipid droplets in HeLa cells, without inducing any appreciable cytotoxicity or competing plasma membrane labeling; this confirmed their potential as fluorescent stains.