title: A Three-Component Assembly Promoted by Boronic Acids Delivers a Modular Fluorophore Platform (BASHY Dyes).
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.
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.
authors.forename: Fábio M F
authors.initials: FM
authors.lastname: Santos
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.
authors.forename: João N
authors.initials: JN
authors.lastname: Rosa
authors.affiliation: Department of Chemistry and Bioengineering, Tampere University of Technology, Korkeakoulunkatu 8, 33101, Tampere, Finland.
authors.forename: Nuno R
authors.initials: NR
authors.lastname: Candeias
authors.affiliation: CIQSO - Center for Research in Sustainable Chemistry, and Department of Chemistry, University of Huelva, Campus de El Carmen s/n, 21071, Huelva, Spain.
authors.forename: Cátia Parente
authors.initials: CP
authors.lastname: Carvalho
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.
authors.forename: Ana I
authors.initials: AI
authors.lastname: Matos
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.
authors.forename: Ana E
authors.initials: AE
authors.lastname: Ventura
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.
authors.forename: Helena F
authors.initials: HF
authors.lastname: Florindo
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal.
authors.forename: Liana C
authors.initials: LC
authors.lastname: Silva
authors.affiliation: 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.
authors.forename: Uwe
authors.identifier: http://orcid.org/0000-0001-8893-9829
authors.initials: U
authors.lastname: Pischel
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003, Lisbon, Portugal. pedrogois@ff.ulisboa.pt.
authors.forename: Pedro M P
authors.initials: PM
authors.lastname: Gois
keywords: boron; charge transfer; dyes/pigments; fluorescence; imaging