ABSTRACT
A new BODIPY system displaying an intramolecular π-π-interaction was synthesized and studied. When the selenium center was oxidized, the substituted phenyl group undergoes π-π stacking with one side of the BODIPY core. The oxidized form showed, not only a down-field shift in the NMR peak, but also splitting due to geometrical changes that arise when going from Cs to C1. The compound was characterized by X-ray diffraction; DFT methods helped elucidate the influence of the unexpected π-π stack and its connection to the photophysical properties imparted by the Se oxidation.
ABSTRACT
Highly specific and sensitive fluorescence detection of hypochlorite in nonbiotic pure water (rapid "turn-on", ~400 fold, λ(em) ~ 560 nm) as well as in living neuronal cell cultures (neutral pH) involves oxidation of a 2-sulfide-2-benzoic acid pendent group in a new meso-thienyl-BODIPY donor-acceptor probe.
Subject(s)
Boron Compounds/chemistry , Esterases/metabolism , Fluorescence , Fluorescent Dyes/chemistry , Hypochlorous Acid/analysis , Neuroblastoma/enzymology , Benzenesulfonates/chemistry , Benzoates/chemistry , Cell Survival , Humans , Microscopy, Fluorescence , Molecular Structure , Neuroblastoma/metabolism , Neuroblastoma/pathology , Oxidation-Reduction , Reactive Oxygen Species/metabolism , Tumor Cells, CulturedABSTRACT
Bis-arylsulfide BODIPY systems were prepared and studied for multiple O-atom sensing (at 522 nm); 2- and 3-atom loading was optimal (50-fold, "turn on"). Neuronal studies showed greater H(2)O(2) sensitivity than 2',7'-dichlorofluorescein diacetate. The novel 1,3,6-trimethyl BODIPY formed as a biproduct under Lindsey conditions.
