Format

Send to

Choose Destination
Chemistry. 2016 Jan 26;22(5):1631-7. doi: 10.1002/chem.201503943. Epub 2015 Dec 22.

A Three-Component Assembly Promoted by Boronic Acids Delivers a Modular Fluorophore Platform (BASHY Dyes).

Author information

1
Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.
2
Department of Chemistry and Bioengineering, Tampere University of Technology, Korkeakoulunkatu 8, 33101, Tampere, Finland.
3
CIQSO - Center for Research in Sustainable Chemistry, and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, 21071, Huelva, Spain.
4
CIQSO - Center for Research in Sustainable Chemistry, and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, 21071, Huelva, Spain. uwe.pischel@diq.uhu.es.
5
Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal. pedrogois@ff.ulisboa.pt.

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.

KEYWORDS:

boron; charge transfer; dyes/pigments; fluorescence; imaging

Supplemental Content

Full text links

Icon for PubMed Central
Loading ...
Support Center