99049-43-1Relevant articles and documents
(E)-2-Styrylanthracene-9,10-dione: A new type of fluorescent probe core and its application in specific mitochondria imaging
Lu, Peng-fei,Meng, Fan-hao,Wang, Lin,Wang, Qiu-yin,Wang, Zhao-ran,Zhang, Ting-jian,Zhang, Xu,Zhao, Hai-yang
, (2021/09/20)
Herein, a new type of fluorescent probe core, (E)-2-styrylanthracene-9,10-dione (EK01), was developed which displayed strong fluorescence quantum yield (Φ = 0.867 in DMF; Φ = 0.561 in acetone; Φ = 0.616 in CH2Cl2; Φ = 0.265 in DMSO), good photostability, large stokes shift (90 nm–120 nm) and molar extinction coefficients (0.5875 × 104–0.7609 × 104 mol?1 L cm?1). During cell assays and co-localization experiments, EK01 showed excellent cell membrane permeability and low cytotoxicity against MCF-10A (human mammary epithelial cell line) and HT-29 (human colorectal adenocarcinoma cell line). Particularly, we surprisingly discovered that EK01 could selectively aggregate in mitochondria and specific stain it in a green emissive fluorescent form, which means that EK01 could be a real-time specifically monitor of mitochondria in living cells with a high signal-to-noise ratio. Hence a new mitochondria imaging method was established which is incubating EK01 with living cells for 1 h at a final concentration of 6–12 μM, then visualizing under a confocal microscope at 395 nm. It is worth noting that the fluorescence efficiency of EK01 is not outstanding in organisms, it has much stronger fluorescence efficiency in other organic solvent systems (such as DMF, acetone and CH2Cl2). Therefore, as a new type of fluorescent core that is easy to synthesis and graft, we believe that (E)-2-styrylanthracene-9,10-diones have the potential to develop a variety of fluorescence platforms applying in different fields.
Chromo-fluorogenic detection of nerve-agent mimics using triggered cyclization reactions in push-pull dyes
Costero, Ana M.,Parra, Margarita,Gil, Salvador,Gotor, Raffll,Mancini, Pedro M. E.,Martinez-Macez, Ramon,Sancenon, Felix,Royo, Santiago
experimental part, p. 1573 - 1585 (2011/08/05)
A family of azo and stilbene derivatives (1-9) are synthesized, and their chromo-fluorogenic behavior in the presence of nerve-agent simulants, diethylchlorophosphate (DCP), diisopropylfluorophosphate (DFP), and diethylcyanophosphate (DCNP) in acetonitrile and mixed solution of water/acetonitrile (3:1 v/v) buffered at pH 5.6 with MES, is investigated. The prepared compounds contain 2-(2-N,N-dimethylaminophenyl) ethanol or 2-[(2-N,N-dimethylamino)phenoxy]ethanol reactive groups, which are part of the conjugated π-system of the dyes and are able to give acylation reactions with phosphonate substrates followed by a rapid intramolecular N-alkylation. The nerve-agent mimic-triggered cyclization reaction transforms a dimethylamino group into a quaternary ammonium, inducing a change of the electronic properties of the delocalized systems that results in a hypsochromic shift of the absorption band of the dyes. Similar reactivity studies are also carried out with other "non-toxic" organophosphorus compounds, but no changes in the UV/Vis spectra were observed. The emission behaviour of the reagents in acetonitrile and water-acetonitrile 3:1 v/v mixtures is also studied in the presence of nerve-agent simulants and other organophosphorous derivatives. The reactivity between 1-9 and DCP, DCNP, or DFP in buffered water-acetonitrile 3:1 v/v solutions under pseudo first-order kinetic conditions, using an excess of the corresponding simulant, are studied in order to determine the rate constants (k) and the half-life times (t1/2=ln2/k) for the reaction. The detection limits in water/acetonitrile 3:1 v/v are also determined for 1-9 and DCP, DCNP, and DFP. Finally, the chromogenic detection of nerve agent simulants both in solution and in gas phase are tested using silica gel containing adsorbed compounds 1, 2, 3, 4, or 5 with fine results.
PHOSPHONIUM YLIDES IN THE QUINONE SERIES. ANTHRAQUINONE DERIVATIVES
Listvan, V. N.,Stasyuk, A. P.
, p. 674 - 679 (2007/10/02)
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