Dataset Information

Highly Stable, Readily Reducible, Fluorescent, Trifluoromethylated 9-Borafluorenes.

ABSTRACT: Three different perfluoroalkylated borafluorenes (F Bf) were prepared and their electronic and photophysical properties were investigated. The systems have four trifluoromethyl moieties on the borafluorene moiety as well as two trifluoromethyl groups at the ortho positions of their exo-aryl moieties. They differ with regard to the para substituents on their exo-aryl moieties, being a proton (F XylF Bf, F Xyl: 2,6-bis(trifluoromethyl)phenyl), a trifluoromethyl group (F MesF Bf, F Mes: 2,4,6-tris(trifluoromethyl)phenyl) or a dimethylamino group (p-NMe2 -F XylF Bf, p-NMe2 -F Xyl: 4-(dimethylamino)-2,6-bis(trifluoromethyl)phenyl), respectively. All derivatives exhibit extraordinarily low reduction potentials, comparable to those of perylenediimides. The most electron-deficient derivative F MesF Bf was also chemically reduced and its radical anion isolated and characterized. Furthermore, all compounds exhibit very long fluorescent lifetimes of about 250?ns up to 1.6??s; however, the underlying mechanisms responsible for this differ. The donor-substituted derivative p-NMe2 -F XylF Bf exhibits thermally activated delayed fluorescence (TADF) from a charge-transfer (CT) state, whereas the F MesF Bf and F XylF Bf borafluorenes exhibit only weakly allowed locally excited (LE) transitions due to their symmetry and low transition-dipole moments.

SUBMITTER: Rauch F

PROVIDER: S-EPMC7589458 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Publications

Highly Stable, Readily Reducible, Fluorescent, Trifluoromethylated 9-Borafluorenes.

Rauch Florian F Fuchs Sonja S Friedrich Alexandra A Sieh Daniel D Krummenacher Ivo I Braunschweig Holger H Finze Maik M Marder Todd B TB

Chemistry (Weinheim an der Bergstrasse, Germany) 20200921 56

Three different perfluoroalkylated borafluorenes (F Bf) were prepared and their electronic and photophysical properties were investigated. The systems have four trifluoromethyl moieties on the borafluorene moiety as well as two trifluoromethyl groups at the ortho positions of their exo-aryl moieties. They differ with regard to the para substituents on their exo-aryl moieties, being a proton (F XylF Bf, F Xyl: 2,6-bis(trifluoromethyl)phenyl), a trifluor ...[more]

PMID: 31999019

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Project description:Hydrogen peroxide (H2O2) plays an important role in modulating cell signaling and homeostasis in live organisms. The HyPer family of genetically encoded indicators allows the visualization of H2O2 dynamics in live cells within a limited field of view. The visualization of H2O2 within a whole organism with a single cell resolution would benefit from a slowly reducible fluorescent indicator that integrates the H2O2 concentration over desired time scales. This would enable post hoc optical readouts in chemically fixed samples. Herein, we report the development and characterization of NeonOxIrr, a genetically encoded green fluorescent indicator, which rapidly increases fluorescence brightness upon reaction with H2O2, but has a low reduction rate. NeonOxIrr is composed of circularly permutated mNeonGreen fluorescent protein fused to the truncated OxyR transcription factor isolated from E. coli. When compared in vitro to a standard in the field, HyPer3 indicator, NeonOxIrr showed 5.9-fold higher brightness, 15-fold faster oxidation rate, 5.9-fold faster chromophore maturation, similar intensiometric contrast (2.8-fold), 2-fold lower photostability, and significantly higher pH stability both in reduced (pKa of 5.9 vs. ≥7.6) and oxidized states (pKa of 5.9 vs.≥ 7.9). When expressed in the cytosol of HEK293T cells, NeonOxIrr demonstrated a 2.3-fold dynamic range in response to H2O2 and a 44 min reduction half-time, which were 1.4-fold lower and 7.6-fold longer than those for HyPer3. We also demonstrated and characterized the NeonOxIrr response to H2O2 when the sensor was targeted to the matrix and intermembrane space of the mitochondria, nucleus, cell membranes, peroxisomes, Golgi complex, and endoplasmic reticulum of HEK293T cells. NeonOxIrr could reveal endogenous reactive oxygen species (ROS) production in HeLa cells induced with staurosporine but not with thapsigargin or epidermal growth factor. In contrast to HyPer3, NeonOxIrr could visualize optogenetically produced ROS in HEK293T cells. In neuronal cultures, NeonOxIrr preserved its high 3.2-fold dynamic range to H2O2 and slow 198 min reduction half-time. We also demonstrated in HeLa cells that NeonOxIrr preserves a 1.7-fold ex vivo dynamic range to H2O2 upon alkylation with N-ethylmaleimide followed by paraformaldehyde fixation. The same alkylation-fixation procedure in the presence of NP-40 detergent allowed ex vivo detection of H2O2 with 1.5-fold contrast in neuronal cultures and in the cortex of the mouse brain. The slowly reducible H2O2 indicator NeonOxIrr can be used for both the in vivo and ex vivo visualization of ROS. Expanding the family of fixable indicators may be a promising strategy to visualize biological processes at a single cell resolution within an entire organism.

Dataset Information

Highly Stable, Readily Reducible, Fluorescent, Trifluoromethylated 9-Borafluorenes.

Publications

Highly Stable, Readily Reducible, Fluorescent, Trifluoromethylated 9-Borafluorenes.

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