2015
DOI: 10.1002/anie.201410645
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Ratiometric Fluorescence Imaging of Cellular Polarity: Decrease in Mitochondrial Polarity in Cancer Cells

Abstract: Mitochondrial polarity strongly influences the intracellular transportation of proteins and interactions between biomacromolecules. The first fluorescent probe capable of the ratiometric imaging of mitochondrial polarity is reported. The probe, termed BOB, has two absorption maxima (λabs = 426 and 561 nm) and two emission maxima--a strong green emission (λem = 467 nm) and a weak red emission (642 nm in methanol)--when excited at 405 nm. However, only the green emission is markedly sensitive to polarity changes… Show more

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Cited by 214 publications
(159 citation statements)
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“…The synthetic route to obtain substrate 10 combined a series of well-established methods (Scheme 1); for the synthesis of 7-diethylaminocoumarin 6, a Wittig reaction 6 between methyl (triphenylphosphoranylidene)acetate and 4-diethyl-aminosalicylaldehyde 5 resulted in a significantly higher yield in comparison to the conventional Knoevenagel condensation 7 (see Section 5.1.1.). Introduction of the formyl functionality onto position 3 of the coumarin ring (7) involved a Vilsmeier-Haack formylation via a previously reported procedure.…”
Section: Synthesis and Characterizationmentioning
confidence: 99%
“…The synthetic route to obtain substrate 10 combined a series of well-established methods (Scheme 1); for the synthesis of 7-diethylaminocoumarin 6, a Wittig reaction 6 between methyl (triphenylphosphoranylidene)acetate and 4-diethyl-aminosalicylaldehyde 5 resulted in a significantly higher yield in comparison to the conventional Knoevenagel condensation 7 (see Section 5.1.1.). Introduction of the formyl functionality onto position 3 of the coumarin ring (7) involved a Vilsmeier-Haack formylation via a previously reported procedure.…”
Section: Synthesis and Characterizationmentioning
confidence: 99%
“…The luminescence measurements generally use fluorescent materials. Some organic fluorescent dyes 3 and QDs 4 for the detection and imaging of cancer cells have been reported in the literature recently. However, the intrinsic photophysical properties of organic fluorescent dyes generally have broad absorption/emission spectrum and low photobleaching thresholds, 5 and QDs that contain heavy metals have potential cytotoxicity in vitro and in vivo, 6 which significantly limits their effectiveness in bioimaging.…”
Section: Introductionmentioning
confidence: 99%
“…Recently, two-photon fluorescence (TPF) probes, which can be excited by two-photon absorption in the NIR wavelength, provided an opportunity to overcome the problems originated from the single-photon fluorescence technology [6]. On the other hand, a ratiometric fluorescent probe, measuring the ratio of fluorescence intensities at two different wavelengths can eliminate the influence such as concentration, photobleaching and background interference to realize quantitative detection [7, 8]. To the best of our knowledge, no ratiometric two-photon fluorescent probe for hydrazine has been reported in the literature to date.…”
Section: Introductionmentioning
confidence: 99%