Cell penetrating, mitochondria targeting multiply charged DABCO-cyanine dyes

Abstract

Unless otherwise stated, all starting materials and solvents required for the synthesis of the DABCO cyanine dyes were purchased from Sigma-Aldrich, Organica Feinchemie GmbH Wolfen, Fluka, Alfa-Aesar, TCI Europe, Deutero GmbH, and used without any further purification. The solvents used for the spectroscopic analyses were purchased form Macron Fine Chemicals TM. All other starting materials and solvents were commercial products of analytical grade and were used without further purification. 2.2 Synthesis and spectroscopic analysis of the dyes 2.3. Analysis methods and equipment All products were characterized using various spectroscopic techniques. The progress of the reactions was monitored employing TLC (Merck F 254 silica gel; chloroform: methanol: acetic acid-80:15:5). Recrystallization from methanol yielded analytical samples of the title cyanines. 1 H-NMR and APT-NMR spectra of the compounds were recorded on a Brucker Avance III 500 MHz instrument in DMSO-d6 at room temperature. Chemical shifts were reported in ppm in δ-values with respect to tetramethylsilane (TMS) as an internal reference, or the corresponding peak of the deuterated solvent. Coupling constants JH-H were expressed in Hz. The structures of all intermediates were also evaluated on the target cyanine dyes. Melting point temperatures were evaluated on a Kofler bench and are uncorrected. Absorption and steady state fluorescence spectra of the unbound dyes were recorded in methanol solutions at room temperature, using 10-mm path-length quartz cuvettes on a Cecil Aurius CE 3021 UV-Vis spectrophotometer and Perkin Elmer LS45 fluorescence spectrometer (fixed slits 10-10 nm) at room temperature. 2.4. Synthetic approach to the DABCO monomethine cyanines and intermediate products 2.4.1. Preparation of intermediates 2a-2c

Deep-Red Light-up Signaling of Benzo[c,d]indole–Quinoline Monomethine Cyanine for Imaging of Nucleolar RNA in Living Cells and for Sequence-Selective RNA Analysis

“…The colocalization experiments using organelle-selective fluorescent probes revealed that the emission in the cytoplasm was due to the accumulation of BIQ in the mitochondria (Figure S11). Such a behavior was reported in other monomethine cyanines. , On the other hand, it is highly likely that the nucleolar fluorescence signal arises from the binding of BIQ to RNAs that were abundant in the nucleolus, such as rRNAs. − To confirm this, we examined deoxyribonuclease (DNase) and ribonuclease (RNase) digestion experiments in fixed-permeabilized MCF7 cells (Figure B). As observed for the living cells (cf.…”

“…Such a behavior was reported in other monomethine cyanines. 36,37 On the other hand, it is highly likely that the nucleolar fluorescence signal arises from the binding of BIQ to RNAs that were abundant in the nucleolus, such as rRNAs. 13−16 To confirm this, we examined deoxyribonuclease (DNase) and ribonuclease (RNase) digestion experiments in fixed-permeabilized MCF7 cells (Figure 2B).…”

Wide-Band-Gap Metal-Free Perovskite for Third-Order Nonlinear Optics

“…N-Methyl-1,4-diazabicyclo[2.2.2]octan-1-ium (MDABCO) iodide was synthesized as described elsewhere. 44,45 Metal halide perovskite films were obtained by using the antisolvent method described elsewhere. 46,47 N-Methyl-1,4-diazabicyclo[2.2.2]octan-1-ium Ammonium Iodide (MDNI).…”

Deep-red fluorogenic cyanine dyes carrying an amino group-terminated side chain for improved RNA detection and nucleolar RNA imaging

“… 6 Similar behavior was also found in the parent BIQ 4 and other monomethine cyanines. 7 Meanwhile, it is highly likely that the fluorescence signal in the nucleolus arises from the binding of BIQ–NH 2 to RNAs that were abundant in the nucleolus, such as ribosomal RNAs (rRNAs). 3,4 This was supported by the examination of nuclease digestion in the fixed-permeabilized cells ( Fig.…”