14619-86-4Relevant academic research and scientific papers
Novel selenium-containing acenaphtho[1,2-b]pyrrole derivatives: Synthesis and bioactivity
Wang, Jisong,Yang, Fuli,Zheng, Liang,Ren, Gang,Qi, Jiude,Wang, Zhijun,Zhao, Liwei
, p. 715 - 718 (2016)
Seven novel selenium-containing acenaphtho[1,2-b]pyrrole derivatives were designed and synthesized and their cytotoxic effects were evaluated by the MTT tetrazolium dye assay. Two compounds presented good anticancer activities.
Ratiometric and reusable fluorescent nanoparticles for Zn2+ and H2PO4- detection in aqueous solution and living cells
He, Chunsheng,Zhu, Weiping,Xu, Yufang,Zhong, Ye,Zhou, Juan,Qian, Xuhong
, p. 10755 - 10764 (2010)
In this work, three kinds of core-shell silica nanoparticle-based fluorescent materials were prepared based on a modified Stoeber-Van Blaaderen method. They were characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), dynamic light scattering (DLS), FT-IR, and several other spectroscopic methods. Firstly, The silica@sensor-1 nanoparticle (SSN) showed high selectivity toward Zn2+, which can detect Zn2+ in aqueous solution and living cells. It also can be reused to detect Zn2+ for at least four cycles after a simple regeneration. Secondly, to create a ratiometric measurement platform, the dye-2@silica nanoparticles (DSN), a new class of core-shell fluorescent silica nanoparticles were prepared with an acenaphtho[1, 2-b]pyrrol-9-carbonitrile chromophore derivative as the inner reference. It showed negligible sensing properties towards Zn2+, and the fluorescent intensity was not subjected to interference induced by pH change. Thirdly, the dye-2@silica@sensor-1 nanoparticles (DSSN), with the above reference dye buried inside the silica matrix and a layer of chemosensors anchored onto the surface of silica nanoparticles were prepared. DSSN showed not only the same sensing ability as SSN, but also a clear ratiometric fluorescent signal toward Zn 2+ in aqueous solutions and living cells. On the other hand, H 2PO4- is a well-known Zn2+ binder, so the [DSSN@Zn2+] complex was found to ratiometrically detect H 2PO4-. It responded to H2PO 4- at a neutral aqueous solution with a detection limit lower than 6 × 10-6 M. Moreover, the ratio of fluorescence intensity was linearly increased in the range 6～500 μM of H 2PO4-, which implies a potential application for the quantitation of H2PO4- in aqueous solution. To the best of our knowledge, this is the first example of core-shell silica nanoparticle-based fluorescent materials that can be repeatedly used to ratiometrically detect Zn2+ and H2PO4 - in 100% neutral aqueous solutions.
1-oxo-1H-phenalene-2,3-dicarbonitrile heteroaromatic scaffold: Revised structure and mechanistic studies
Lenk, Romaric,Tessier, Arnaud,Lefranc, Pierre,Silvestre, Virginie,Planchat, Aurlien,Blot, Virginie,Dubreuil, Didier,Lebreton, Jacques
, p. 9754 - 9761 (2014)
Synthesis of the originally proposed 8-oxo-8H-acenaphtho[1,2-b]pyrrol-9-carbonitrile led to a structural revision, and the product has now been identified as unknown compound 1-oxo-1H-phenalene-2,3-dicarbonitrile. The structural assignment was corroborate
A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging
Zhang, Meng,Yu, Mengxiao,Li, Fuyou,Zhu, Minwei,Li, Manyu,Gao, Yanhong,Li, Lei,Liu, Zhiqiang,Zhang, Jianping,Zhang, Dengqing,Yi, Tao,Huang, Chunhui
, p. 10322 - 10323 (2007)
We demonstrated a highly electron-deficient system 1 as a turn-on fluorescence sensor for intracellular imaging of Cys/Hcy in biological samples. On the basis of the specific nucleophilic ability of thiols of Cys and Hcy, 1 exhibited high selectivity and sensitivity for Cys/Hcy over other amino acids and thiol biomolecules. This probe is the first Cys/Hcy sensor with excitation in the visible region and turn-on (75-fold) fluorescence emission and also gives a significant increase in two-photon excited fluorescence for sensing Cys/Hcy. Moreover, confocal laser scanning microscopy and two-photon laser scanning microscopy experiments further established that 1 can be used for sensing Cys/Hcy within biological samples. Copyright
A novel Hsp70 inhibitor specifically targeting the cancer-related Hsp70-Bim protein-protein interaction
Wang, Ziqian,Song, Ting,Guo, Zongwei,Uwituze, Laura B.,Guo, Yafei,Zhang, Hong,Wang, Hang,Zhang, Xiaodong,Pan, Hao,Ji, Tong,Yin, Fangkui,Zhou, Sheng,Dai, Jian,Zhang, Zhichao
, (2021)
Targeting cancer-related Hsp70-Bim protein-protein interactions (PPIs) offers a new strategy for the design of Hsp70 inhibitors. Herein, we discovered a novel Hsp70 inhibitor, S1g-6, based on the established BH3 mimetics. S1g-6 exhibited sub-μM binding af
A Synthesis of Novel Perinaphthenones from Acetylenic Esters and Acenaphthoquinone-Malononitrile Adduct in the Presence of Triphenylphosphine
Yavari, Issa,Khajeh-Khezri, Aliyeh,Halvagar, Mohammad Reza
, p. 2011 - 2014 (2018)
A facile protocol involving Tebby zwitterions (PPh 3 -acetylenic esters) and the Knoevenagel condensation product of acenaphthylene-1,2-dione with malononitrile or ethyl cyanoacetate for the selective synthesis of a new series of perinaphthenone derivatives is described. Triphenylphosphine plays a catalytic role in these transformations. The structure of a typical product was confirmed by X-ray crystallography. The merits of this method include high yields of products, good atom economy, and a metal-free catalyst.
One-pot, sequential four-component synthesis of novel heterocyclic [3.3.3] propellane derivatives at room temperature
Beyrati, Maryam,Hasaninejad, Alireza
, p. 14171 - 14176 (2018)
An efficient, one-pot, two-step, four-component reaction for the synthesis of propellane derivatives is described by the condensation reaction between acenaphthenequinone, malono derivatives, primary amines and β-ketoester or β-diketone derivatives in the presence of triethylamine in ethanol at room temperature. Using this procedure, all the products were obtained in good to excellent yields.
Synthesis and evaluation of novel 8-oxo-8H-cyclopenta[a]acenaphthylene-7- carbonitriles as long-wavelength fluorescent markers for hypoxic cells in solid tumor
Liu, Yan,Xu, Yufang,Qian, Xuhong,Xiao, Yi,Liu, Jianwen,Shen, Liyun,Li, Junhui,Zhang, Yuanxing
, p. 1562 - 1566 (2006)
Novel bioreductive and long-wavelength fluorescent markers for hypoxic cells in solid tumor, 9-isocyano-8H-acenaphtho[l,2-b]pyrrol-8-one with the side chain of 2-nitroimidazole, were designed, synthesized, and evaluated in V79 379A Chinese hamster cells in vitro. Compounds A2 and A4 showed good hypoxic-oxic fluorescence differential in vitro (V79 cells) by using fluorescence scan ascent.
Light-induced activities of novel naphtho[1,8-ef]isoindole-7,8,10(9H)-trione and oxoisoaporphine derivatives towards mosquito larvae
Feng, Hao,Shao, Xusheng,Xu, Qi
, (2021)
Infected mosquitoes are significant vectors of dengue, yellow fever, chikungunya, zika and other pathogens. In the view of increasing resistance in mosquito larvae control, photoactivated insecticides is a promising approach by utilizing highly toxic singlet oxygen produced by photosensitizer through irradiation. However, the choice of photosensitizer for mosquito control is limited. Here, we report a novel series of naphtho[1,8-ef]isoindole-7,8,10(9H)-trione and oxoisoaporphines derivatives as excellent type II photosensitizers. Meanwhile, the light-dependent activities against permethrin-susceptible and permethrin-resistant strain of Aedes aegypti mosquito larvae of these compounds were evaluated. Among them, compound 7b was proved to be potential photodynamic insecticide due to its excellent phototoxicity, the LC50 value was 0.19 μg mL?1 under visible light irradiation. The irradiation-generated enhancement in the activity was more than 520-fold. This compound could be the potential candidate in the search for new photoactivated insecticide leads. Importantly, 7b has good fluorescence quantum yield (?F = 0.70), it can be used as a fluorescence indicator in mosquito larvae to observe uptake and morphology change.
Chromo-and fluorophoric water-soluble polymers and silica particles by nucleophilic substitution reaction of poly(vinyl amine)
Hofmann, Katja,Kahle, Ingolf,Spange, Stefan,Simon, Frank
, (2010)
Novel chromophoric and fluorescent carbonitrile-functionalized poly(vinyl amine) (PVAm) and PVAm/silica particles were synthesized by means of nucleophilic aromatic substitution of 8-oxo-8H-acenaphtho[1,2-b]pyrrol-9- carbonitrile (1) with PVAm in water. The water solubility of 1 has been mediated by 2,6-O-β-dimethylcyclodextrin or by pre-adsorption onto silica particles. Furthermore, 1 was converted with isopropylamine into the model compound 1-M. All new compounds were characterized by NMR, FTIR, UV-vis and fluorescence spectroscopy. The solvent-dependent UV-vis absorption and fluorescence emission band positions of the model compound and the carbonitrile-functionalized PVAm were studied and interpreted using the empirical Kamlet-Taft olvent parameters ?* (dipolarity/polarizability), α (hydrogen-bond donating capacity) and β (hydrogen-accepting ability) in terms of the linear solvation energy relationship (LSER). The solvent-independent regression coefficients a, b and s were determined using multiple linear correlation analysis. It is shown, that the chains of the polymer have a significant influence on the solvatochromic behavior of 1-P. The structure of the carbonitrile 1-Si bound to polymer-modified silica particles was studied by means of X-ray photoelectron spectroscopy (XPS) and Brunauer-Emmett-Teller (BET) measurements. Fluorescent silica particles were obtained as shown by fluorescence spectroscopy with a diffuse reflectance technique.
