1468-95-7Relevant articles and documents
Light- and heat-triggered reversible luminescent materials based on polysiloxanes with anthracene groups
Han, Dongdong,Lu, Hang,Li, Wensi,Li, Yonghao,Feng, Shengyu
, p. 56489 - 56495 (2017)
In this study, reversible silicone elastomers were successfully developed by light-triggered dimerization and heat depolymerization of the anthryl groups. Polysiloxanes with anthryl groups were prepared from poly(aminopropylmethylsiloxane) (PAPMS) with electron-donating (9-anthracenylmethyl acrylate) and electron-withdrawing (anthracene-9-carboxylic acid) units. The cross-linking networks were formed with the via 4π-4π photo-cycloadditions of the anthryl groups upon the UV light excitation (365 nm). 9-Anthracenylmethyl acrylate or anthracene-9-carboxylic acid efficiently dimerized through the photodimerization of the anthryl groups in the organic solvents, which was proven by UV-vis spectra, NMR spectra, and LC/MS. The covalent bonds between pendant anthryl groups were cleaved after heating at 120 °C. Furthermore, repeatable dimerization-depolymerization conversion was confirmed. In addition, for the first time, we found that the sunlight can also initiate the cycloaddition, which was "greener" and more environment-friendly. The green luminescence was observed from the PAPMS-1 film instead of the quenching effect caused by aggregation after the cycloaddition. Thus, a colorful UV-light emitting diode (LED) cell was obtained by coating the films on the commercially available LED cell.
A Fluorescent Silver(I) Carbene Complex with Anticancer Properties: Synthesis, Characterization, and Biological Studies
Fabbrini, Maria Giulia,Cirri, Damiano,Pratesi, Alessandro,Ciofi, Lorenzo,Marzo, Tiziano,Guerri, Annalisa,Nistri, Silvia,Dell'Accio, Alfonso,Gamberi, Tania,Severi, Mirko,Bencini, Andrea,Messori, Luigi
, p. 182 - 188 (2019)
The silver(I) N-heterocyclic carbene (NHC) complex bis(1-(anthracen-9-ylmethyl)-3-ethylimidazol-2-ylidene) silver chloride ([Ag(EIA)2]Cl), bearing two anthracenyl fluorescent probes, has been synthesized and characterized. [Ag(EIA)2]Cl is stable in organic solvents and under physiological conditions, and shows potent cytotoxic effects in vitro toward human SH-SY5Y neuroblastoma cells. The interactions of [Ag(EIA)2]Cl with a few model biological targets have been studied as well as its ability to be internalized in cells. The in vitro anticancer activity is apparently related to the level of drug internalization. Notably, [Ag(EIA)2]Cl does not react with a few model proteins, but is capable of binding the C-terminal dodecapeptide of thioredoxin reductase hTrxR(488–499) and to strongly inhibit the activity of this enzyme. Binding occurs through an unconventional process leading to covalent binding of one or two carbene ligands to the C-terminal dodecapeptide with concomitant release of the silver cation. To the best of our knowledge, this mode of interaction is reported here for the first time for Ag(NHC)2 complexes.
A simple and robust PET-based anthracene-appended O-N-O chelate for sequential recognition of Fe3+/CN– ions in aqueous media and its multimodal applications
Pandith, Anup,Choi, Jun-Hyeak,Jung, Ok-Sang,Kim, Hong-Seok
, p. 669 - 680 (2018)
A very simple, robust, and pico/nanomolar-sensitive 9,10-diethanolamine-substituted fluorescent Fe3+/CN– probe (PD) was synthesised, and its sensing abilities towards various ions were studied in mixed aqueous media. PD selectively recognised Fe3+ ions through a ‘turn on’ response with an excellent binding constant (Ka, 9.29 × 106 M?1) in 1:2 binding stoichiometry at pH 7.0 in phosphate-buffered saline (PBS). The in situ generated Fe3+·PD ensemble sequentially recognised CN– ions with an excellent binding constant (Ka 1.72 × 108 M?1) via a ‘turn off’ mode by extruding Fe3+ ions from the ensemble. The highly selective sequential ‘on-off’ responses towards Fe3+ and CN– ions were attributed to inhibition and restoration of photoinduced electron transfer (PET) and chelation-induced enhanced fluorescence (CHEF) effects from the chelating N and O heteroatoms. PD was able to detect Fe3+ and CN– ions in real water samples satisfactorily at picomolar to sub-nanomolar levels. A colorimetric assay based on pyrocatechol violet (PCV) was also able to detect Fe3+/CN– in a sequential manner (up to sub-micromolar level) by a change in colour from colourless to yellow/pale green without any interferences from other ions. Based on the complexation and decomplexation mechanism, bio-imaging photonic INHIBIT logic circuit strips were prepared for use under physiological conditions. In addition, solid-phase recognition of Fe3+/CN– ions was demonstrated using cost-effective paper-based strips.
Synthesis of 9-Substituted Triptycene Building Blocks for Solid-Phase Diversification and Nucleic Acid Junction Targeting
Yoon, Ina,Suh, Sung-Eun,Barros, Stephanie A.,Chenoweth, David M.
, p. 1096 - 1099 (2016)
Triptycenes have been shown to bind nucleic acid three-way junctions, but rapid and efficient methods to diversify the triptycene core are lacking. An efficient synthesis of a 9-substituted triptycene scaffold is reported that can be used as a building block for solid-phase peptide synthesis and rapid diversification. The triptycene building block was diversified to produce a new class of tripeptide-triptycenes, and their binding abilities toward d(CAG)·(CTG) repeat junctions were investigated.
Activation of promutagens by endogenous and heterologous sulfotransferases expressed in continuous cell cultures
Glatt, Hansruedi,Pauly, Karin,Piee-Staffa, Andrea,Seidel, Albrecht,Hornhardt, Sabine,Czich, Andreas
, p. 13 - 22 (1994)
various environmental chemical are metabolised to chemically reactive sulfuric acid esters, which may covalently bind to cellular macromoleculaes and induce mutations and tumours. This activation pathway is usually not taken into account in external xenobiotic-metabolising systems used in short-term tests. We therefore analysed the abilities of cytosols from mammalian cell lines to activate benzylic alcohols (1-hydroxymethylpyrene and 9-hydroxymethylanthracene) to mutagens detectable in Salmonella typhimurium TA98. No activation was observed in cell lines which are commonly used in mutagenicity and cell transformation assays, and only low activities were found in epithelial cell lines in culture. We have therefore constructed Chineses hamster V79-derived cell lines which stably express a heterologous sulfotransferase, rat hydroxysteroid sulfotransferase a. Cytosol of these cells effectively activated 1-hydroxymethylpyrene and 9-hydroxymethylanthracene to mutagens detected in S. pyphimurium. The hepatocarcinogen 6-hydroxymethylbenzopyrene induced gene mutations in sulfotransferase-expressing V79-derived cells, whereas it elicited only marginal effects in sulfotransferase-deficient control cells. The new cell lines may allow the detection of novel classes of mutagens, since some externally generated reactive sulfuric acid esters may not readily penetrate target cells due to their short life span and their ionization. - Keywords: Benzylic alcohols; Bioactivation; Sulfotransferase; Sulfuric acid esters; V79 cells
Preparation and characterisation of fluorescent chitosans using 9-anthraldehyde as fluorophore
Tommeraas, Kristoffer,Strand, Sabina P.,Tian, Wei,Kenne, Lennart,Varum, Kjell M.
, p. 291 - 296 (2001)
Chitosans with chemical composition ranging from a fraction of N-acetylated units (FA) of 0.01 to 0.61 were used to prepare fluorescence labelled chitosans by reductive amination with 9-anthraldehyde. Fluorescent chitosans with a low theoretical degree of substitution (DS, 0.001-1%) were prepared, and the actual DS of the products were determined by UV and 1H NMR spectroscopy. The fluorescence excitation and emission spectra of the chitosan with FA of 0.09 and DS 1% showed an excitation maximum at 254 nm and an emission maximum at 413 nm. The intrinsic viscosities ([η]) of the fluorescent chitosans were compared to those of the original chitosans, showing that the derivatisation procedure lead only to a negligible decrease in [η]. The conformation of these fluorescent chitosans with very low DS-values is not altered and they can conveniently be directly quantified by UV or fluorescence spectroscopy.
Experimental and DFT studies on the vibrational and electronic spectra of 9-anthracenemethanol
Kou, Shanshan,Zhou, Hu,Tang, Guodong,Li, Rongqing,Zhang, Yu,Zhao, Jianying,Wei, Changmei
, p. 768 - 775 (2012)
Vibrational spectral measurements were made for 9-anthracenemethanol. Optimized geometrical structure and harmonic vibration frequencies were computed based on ab initio and density functional theory B3LYP methods using 6-311G and LANL2DZ basis sets. The
A Photo-Triggered Traceless Staudinger–Bertozzi Ligation Reaction
Hu, Peng,Feng, Tianshi,Yeung, Chi-Chung,Koo, Chi-Kin,Lau, Kai-Chung,Lam, Michael H. W.
, p. 11537 - 11542 (2016)
The use of light to control the course of a chemical/biochemical reaction is an attractive idea because of its ease of administration with high precision and fine spatial resolution. Staudinger ligation is one of the commonly adopted conjugation processes that involve a spontaneous reaction between azides and arylphosphines to form iminophosphoranes, which further hydrolyze to give stable amides. We designed an anthracenylmethyl diphenylphosphinothioester (1) that showed promising Staudinger ligation reactivity upon photo-excitation. Broadband photolysis at 360–400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl–phosphorus bond, releasing a diphenylphosphinothioester (2) as an efficient traceless Staudinger–Bertozzi ligation reagent. The quantum yield of such a photo-induced heterolytic bond-cleavage at the optimal wavelength of photolysis (376 nm) at room temperature is ≥0.07. This work demonstrated the feasibility of photocaging arylphosphines to realize the photo-triggering of the Staudinger ligation reaction.
Fluorometric analysis of borohydrides based on reductive aldehyde-to-alcohol conversion of arylaldehydes
Kim, Na Yeong,Baek, Ji Hye,Chang, Suk-Kyu
, p. 59 - 62 (2019)
Fluorometric analysis of borohydride (BH4 –) species by the reduction of arylaldehydes to the corresponding arylmethanols was investigated. 9-Anthracenecarboxaldehyde (9-AA) exhibited pronounced ratiometric fluorescence signaling behavior toward borohydride in alkaline aqueous media. The borohydride-selective signaling of 9-AA was unaffected by the presence of commonly encountered metal ions and anions. 1-Pyrenecarboxaldehyde (1-PA) also showed comparable borohydride signaling behavior. The detection limit was found to be 7.4 μM (0.11 ppm) for 9-AA and 15.7 μM (0.23 ppm) for 1-PA. The utility of the probe with μPAD as a convenient tool for the determination of borohydrides was demonstrated.
The synthesis of a new type of anthracene DNA intercalator
Ostaszewski, Ryszard,Wilczynska, Edyta,Wolszczak, Marian
, p. 2995 - 2996 (1998)
A new type of DNA intercalator based on anthracene 3 was synthesized. Preliminary binding studies show high affinity of this probe to CT-DNA. Higher binding constant of this compound (4.0 x 104 M-1) as compared with that known for 9-aminomethylanthracene, is caused presumably by enhanced electrostatic interaction.
