Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 5, Pages 1631-1637Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503943
Keywords
boron; charge transfer; dyes/pigments; fluorescence; imaging
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Funding
- Fundacao para a Ciencia e a Tecnologia (FCT) Portugal [SFRH/BD/81628/2011, SFRH/BD/94779/2013, PTDC/QUI-QUI/118315/2010, PTDC/SAUFAR/119389/2010, PTDC/BBB-BQB/0506/2012]
- iMed.ULisboa grant [UID/DTP/04138/2013]
- Ministerio de Economia y Competitividad, Madrid, Spain [CTQ2014-54729-C2-1-P]
- Junta de Andalucia [P12-FQM-2140]
- Fundação para a Ciência e a Tecnologia [SFRH/BD/81628/2011, SFRH/BD/94779/2013, PTDC/BBB-BQB/0506/2012, PTDC/QUI-QUI/118315/2010] Funding Source: FCT
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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 54000 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.
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