title: Synthesis of pH-activatable red fluorescent BODIPY dyes with distinct functionalities.
abstract: A series of tunable pH-dependent BODIPY dyes were synthesized and further functionalized in a Knoevenagel condensation reaction with various aldehydes. In this fashion, monofunctional dyes containing an alkyne, azide, or carboxylic acid (masked as its methyl ester) as ligation sites as well as asymmetrical bifunctional dyes were obtained, without compromising their pH-dependency. In addition, fluorescence excitation and emission maxima for these dyes were shown to be significantly red-shifted in comparison to their tetramethyl precursors.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, P.O. Box 9052, 2300 RA Leiden, The Netherlands.
authors.forename: Sascha
authors.initials: S
authors.lastname: Hoogendoorn
authors.forename: Annet E M
authors.initials: AE
authors.lastname: Blom
authors.forename: Lianne I
authors.initials: LI
authors.lastname: Willems
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D013050:Spectrometry, Fluorescence
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D000447:Aldehydes; D001896:Boron Compounds; D005456:Fluorescent Dyes