- Novel selenium-containing acenaphtho[1,2-b]pyrrole derivatives: Synthesis and bioactivity
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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.
- Wang, Jisong,Yang, Fuli,Zheng, Liang,Ren, Gang,Qi, Jiude,Wang, Zhijun,Zhao, Liwei
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- Ratiometric and reusable fluorescent nanoparticles for Zn2+ and H2PO4- detection in aqueous solution and living cells
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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.
- He, Chunsheng,Zhu, Weiping,Xu, Yufang,Zhong, Ye,Zhou, Juan,Qian, Xuhong
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- 1-oxo-1H-phenalene-2,3-dicarbonitrile heteroaromatic scaffold: Revised structure and mechanistic studies
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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
- Lenk, Romaric,Tessier, Arnaud,Lefranc, Pierre,Silvestre, Virginie,Planchat, Aurlien,Blot, Virginie,Dubreuil, Didier,Lebreton, Jacques
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- A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging
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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
- Zhang, Meng,Yu, Mengxiao,Li, Fuyou,Zhu, Minwei,Li, Manyu,Gao, Yanhong,Li, Lei,Liu, Zhiqiang,Zhang, Jianping,Zhang, Dengqing,Yi, Tao,Huang, Chunhui
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- A novel Hsp70 inhibitor specifically targeting the cancer-related Hsp70-Bim protein-protein interaction
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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
- 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
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- A Synthesis of Novel Perinaphthenones from Acetylenic Esters and Acenaphthoquinone-Malononitrile Adduct in the Presence of Triphenylphosphine
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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.
- Yavari, Issa,Khajeh-Khezri, Aliyeh,Halvagar, Mohammad Reza
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- One-pot, sequential four-component synthesis of novel heterocyclic [3.3.3] propellane derivatives at room temperature
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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.
- Beyrati, Maryam,Hasaninejad, Alireza
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- Synthesis and evaluation of novel 8-oxo-8H-cyclopenta[a]acenaphthylene-7- carbonitriles as long-wavelength fluorescent markers for hypoxic cells in solid tumor
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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.
- Liu, Yan,Xu, Yufang,Qian, Xuhong,Xiao, Yi,Liu, Jianwen,Shen, Liyun,Li, Junhui,Zhang, Yuanxing
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- Light-induced activities of novel naphtho[1,8-ef]isoindole-7,8,10(9H)-trione and oxoisoaporphine derivatives towards mosquito larvae
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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.
- Feng, Hao,Shao, Xusheng,Xu, Qi
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- Chromo-and fluorophoric water-soluble polymers and silica particles by nucleophilic substitution reaction of poly(vinyl amine)
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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.
- Hofmann, Katja,Kahle, Ingolf,Spange, Stefan,Simon, Frank
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- Revisit of a series of ICT fluorophores: Skeletal characterization, structural modification, and spectroscopic behavior
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We have revisited the synthesis of a series of ICT fluorophores, which were reported to have a core structure of 8-oxo-8H-acenaphtho[1,2-b]pyrrol-9-carbonitrile. However, based on the 2D NMR and X-ray diffraction analysis, their core structure was correct
- Li, Honglin,Liu, Fengyu,Xiao, Yi,Pellechia, Perry J.,Smith, Mark D.,Qian, Xuhong,Wang, Guiren,Wang, Qian
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- Fe3O4?SiO2?(BuSO3H)3 synthesis as a new efficient nanocatalyst and its application in the synthesis of heterocyclic [3.3.3] propellane derivatives
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The acidic agent (BuSO3H) coated on core‐shell Fe3O4 nanomagnetic particles was successfully designed and synthesized. It was characterized and confirmed by different techniques such as FT‐IR spectroscopy, scanning electron microscopy vibrating sample magnetometer, X‐Ray diffraction, energy dispersive X-ray and Thermogravimetric analysis. The application of Fe3O4?SiO2?(BuSO3H)3 as an efficient catalyst in the synthesis of propellane derivatives was evaluated by the domino reaction of acenaphthenequinone, malono derivatives, primary amines and β-ketoester derivatives under the solvent-free condition at 60 °C.
- Badiei, Alireza,Kheilkordi, Zohreh,Mohammadi Ziarani, Ghodsi
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- A new class of long-wavelength fluorophores: Strong red fluorescence, convenient synthesis and easy derivation
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A new class of structurally simple fluorophores with strong long-wavelength emission have been developed through a very convenient procedure.
- Xiao, Yi,Liu, Fengyu,Qian, Xuhong,Cui, Jingnan
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- Targeting the Allosteric Pathway That Interconnects the Core-Functional Scaffold and the Distal Phosphorylation Sites for Specific Dephosphorylation of Bcl-2
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Protein phosphorylation is the most significant post-translational modification for regulating cellular activities, but site-specific modulation of phosphorylation is still challenging. Using three-dimensional NMR spectra, molecular dynamics simulations, and alanine mutations, we identified that the interaction network between pT69/pS70 and R106/R109 residues prevents the phosphorylation sites from exposure to phosphatase and subsequent dephosphorylation. A Bcl-2-dephosphorylation probe, S1-6e, was designed by installing a carboxylic acid group to a Bcl-2 inhibitor. The carboxyl group competitively disrupts the interaction network between R106/R109 and pT69/pS70 and subsequently facilitates Bcl-2 dephosphorylation in living cells. As a result, S1-6e manifests a more effective apoptosis induction in pBcl-2-dependent cancer cells than other inhibitors exhibiting a similar binding affinity for Bcl-2. We believe that targeting the allosteric pathways interconnecting the core-functional domain and the phosphorylation site can be a general strategy for a rational design of site-specific dephosphorylating probes, since the allosteric pathway has been discovered in a variety of proteins.
- Wang, Ziqian,Song, Ting,Guo, Zongwei,Cao, Keke,Chen, Chao,Feng, Yingang,Wang, Hang,Yin, Fangkui,Zhou, Sheng,Dai, Jian,Zhang, Zhichao
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- A Simplistic Approach for Preparation of Alkylidenemalononitrile Derivatives: Characterization, In silico Studies, Quantum Chemical Evaluation, Molecular Docking, and In vitro Biological Activity Evaluation
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A new and efficient green grinding-based catalyst free Knoevenagel condensation of aldehydes/ketones and malononitrile for the rapid preparation of twelve malononitrile derivatives (C1-C12) is proposed. Characterization of the derivatives was done by sup
- Ahmad, Rumana,Azad, Iqbal,Kamal, Azhar,Khan, Abdul Rahman,Khan, Tahmeena,Nasibullah, Malik
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- TWO-PHOTON FLUORESCENT PROBE USING NAPHTHALENE AS MATRIX AND PREPARATION METHOD AND USE THEREOF
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The present invention provides a novel category of naphthalene-based two-photon fluorescent probes having a general formula I, wherein: X is selected from the X1, X2, X3 and X4; The mentioned two-photon fluorescent probes have a low fluorescence background in the non-tumor cells and tissues, and have a strong and specific fluorescent signal in the tumor cells and tissues. These probes have a certain level of water-solubility, while having good membrane permeability. In addition, they have a bigger effective two-photon absorption cross section. The compounds of the present invention also have a lower biotoxicity, phototoxicity and photobleaching. There is sufficient difference between the spectral range thereof and that of a biological sample.
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Paragraph 0068; 0069
(2014/09/29)
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- Design, synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs
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Spiro heterocycles frequently occur in bioactive molecules. In the pursuit of neonicotinoids with spiro heterocycles, three types of novel neonicotinoids with spirobenzofuranone, spirooxindole or spiroacenaphythylenone framework were designed and synthesized. Insecticidal evaluation showed that some of spirobenzofuranone containing neonicotinoids exhibited moderate activity against cowpea aphid, armyworm or brown planthopper.
- Chen, Nan-Yang,Ren, Li-Ping,Zou, Min-Ming,Xu, Zhi-Ping,Shao, Xu-Sheng,Xu, Xiao-Yong,Li, Zhong
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p. 197 - 200
(2014/02/14)
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- Novel soluble myeloid cell leukemia sequence 1 (Mcl-1) inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g) developed using a fragment-based approach
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Based on a known nanomolar Bcl-2 homology domain 3 (BH3) mimetic 3-thiomorpholin-8-oxo-8H-acenaphtho[1,2-b] pyrrole-9-carbonitrile (S1, MW: 331), we applied a fragment-based approach to obtain BH3 mimetics with improved affinity and improved solubility in a water-ethanol (9:1) cosolvent. After the deconstruction of 1 (S1), we obtained fragment cyanoacetamide (4), which was determined to be a ligand efficiency (LE) hot part. After a rational optimization through fragment evolution beginning with fragment 4, a smaller Mcl-1 inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g, MW: 288) with a 6-fold increase in affinity compared to 1 was obtained, as predicted by our optimization curve and identified by Mcl-1 protein nuclear magnetic resonance (NMR).
- Zhang, Zhichao,Song, Ting,Li, Xiangqian,Wu, Zhiyong,Feng, Yingang,Xie, Feibo,Liu, Chengwu,Qin, Jianquan,Chen, Hongbo
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supporting information
p. 141 - 149
(2013/03/13)
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- A facile intracellular fluorescent probe for detection of hydrazine and its application
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A highly selective fluorescent probe for detection of hydrazine exhibiting good performance in a physiological environment has been developed over other closely related analytes. Furthermore, hydrazine in diluted human blood was tested and the method was applied in live cells.
- Zhao, Jie,Xu, Yongqian,Li, Hongjuan,Lu, Aiping,Sun, Shiguo
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p. 3849 - 3852
(2013/12/04)
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- 3-Thiomorpholin-8-oxo-8H-acenaphtho [1,2-b] pyrrole-9-carbonitrile (S1) derivatives as pan-Bcl-2-inhibitors of Bcl-2, Bcl-xL and Mcl-1
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Based on the binding mode of our previously discovered dual inhibitor of Bcl-2 and Mcl-1, 3-thiomorpholin-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9- carbonitrile (3, S1), a library of 9-substituted 3 derivatives was synthesized to further probe the p4 pocket of the two targets. By NMR, structure-activity relationship study, and site-directed mutation, compound 6d (3-(4- aminophenylthio)-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-3-phenyl)propylamine) was identified to span p2-p4 pockets of Mcl-1, Bcl-2 and Bcl-xL, and then exhibited 9- to 35-fold better affinity to the three targets than 3 (IC 50 = 10, 20 and 18 nM, respectively), which led to greater activity in induction of apoptosis in multiple cancer cell lines. Different contribution of p4 pocket to binding Bcl-2 and Mcl-1 was also investigated by plotting the potency and the HAC of the derivatives.
- Song, Ting,Li, Xiangqian,Chang, Xilong,Liang, Xiaomeng,Zhao, Yan,Wu, Guiye,Xie, Shenghui,Su, Pengchen,Wu, Zhiyong,Feng, Yingang,Zhang, Zhichao
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supporting information
p. 11 - 20
(2013/02/23)
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- One-pot synthesis of biologically important spiro-2-amino-4H-pyrans, spiroacenaphthylenes, and spirooxindoles using DBU as a green and recyclable catalyst in aqueous medium
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We have reported DBU-catalyzed one-pot synthesis of biologically and pharmacologically important spiropyrans from condensation of malononitrile/ethyl cyanoacetate, 1,3-dicarbonyl compounds, and ninhydrin/acenaphthequinone/istain in good yields. This new protocol employing DBU, which is a green, recyclable, and inexpensive catalyst, offers advantages such as mild reaction conditions, short reaction times, and easy isolation of products. The structures have been confirmed by X-ray analysis. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Saluja, Pooja,Aggarwal, Komal,Khurana, Jitender M.
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p. 3239 - 3246
(2013/10/01)
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- General non-catalytic approach to spiroacenaphthylene heterocycles: Multicomponent assembling of acenaphthenequinone, cyclic CH-acids and malononitrile
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The new type of non-catalytic cascade reaction was found: the direct multicomponent reaction of acenaphthenequinone, cyclic CH-acids, and malononitrile to form spiroacenaphthylene heterocycles. The direct heating in water acenaphthenequinone, cyclic CH-ac
- Elinson, Michail N.,Ilovaisky, Alexey I.,Merkulova, Valentina M.,Belyakov, Pavel A.,Barba, Fructuoso,Batanero, Belen
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experimental part
p. 5833 - 5837
(2012/09/10)
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- Direct construction of novel dispiro heterocycles through 1,3-dipolar cycloaddition of azomethine ylides
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The 1,3-dipolar cycloaddition of 2-oxo-(2H)-acenaphthylen-1-ylidene- malononitrile and 2-fluoren-9-ylidene-malononitrile as dipolarophiles have been investigated for the first time with the azomethine ylides generated in situ from N-substituted isatin and
- Dandia, Anshu,Jain, Anuj K.,Bhati, Dharmendra S.
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experimental part
p. 5333 - 5337
(2011/10/30)
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- ACENAPHTHO HETEROCYCLE COMPOUNDS, CYCLODEXTRIN INCLUSION COMPOUNDS AND COMPLEXES, AND USES IN THE MANUFACTURES OF BH3 PROTEIN ANALOGUE, BCL-2 FAMILY PROTEIN INHIBITORS THEREOF
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The present invention relates to acenaphtho heterocyclic compounds, cyclodextrin inclusion compounds and complexes thereof, and their uses in manufacturing the inhibitors of BH3 analogue, Bcl-2 family proteins. The acenaphtho heterocyclic compounds are obtained by introducing oxo-, thio-, carbonyl, ester or acyl in the 3-, 4- and 6-position of 8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile, or further substituting 9-cyano with carboxyl, ester or amide. The compounds can simulate BH3-only protein, competitively binding and antagonizing Bcl-2, Bcl-XL and Mcl-1 proteins in vitro or intracellularly, to induce cell apoptosis. The cyclodextrin inclusion compounds and complexes can improve the effects. Therefore, they can all be used in the manufacture of anticancer compounds.
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Page/Page column 6-7
(2011/10/10)
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- ACENAPHTHO HETEROCYCLE COMPOUNDS, CYCLODEXTRIN INCLUSION COMPOUNDS AND COMPLEXES, AND USES IN THE MANUFACTURES OF BH3 PROTEIN ANALOGUE, BCL-2 FAMILY PROTEIN INHIBITORS THEREOF
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The present invention relates to acenaphtho heterocyclic compounds, cyclodextrin inclusion compounds and complexes thereof, and their uses in manufacturing the inhibitors of BH3 analogue, Bcl-2 family proteins. The acenaphtho heterocyclic compounds are ob
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Page/Page column 4
(2011/10/19)
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- A facile strategy for the one pot multicomponent synthesis of spiro dihydropyridines from amines and activated alkynes
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An efficient preparation of a series of spiro dihydropyridines via one pot four-component reactions of mono/di/tri-ketones, malononitrile, primary amines, and acetylenic esters is reported. The reaction is atom-efficient, high yielding, and follows a simp
- Kiruthika, Selvarangam E.,Lakshmi, Neelakandan Vidhya,Banu, Babu Rasidha,Perumal, Paramasivan T.
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experimental part
p. 6508 - 6511
(2011/12/21)
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