Hang Song

Synthesis and evaluation of 2-[2-(phenylthiomethyl)-1H-benzo[d] imidazol-1-yl)acetohydrazide derivatives as antitumor agents.

A novel class of acetylhydrazone derivatives (5a-x) containing 2-(phenylthiomethyl)-1H-benzo-[d]-imidazole moieties are synthesizer, and their antitumor activities against A549, HCT116, HepG2, PC-9, and A375 were determined by the MTT assay. Among them are N-(2,4-dihydroxybenzylidene)-2-(2-(phenylthiomethyl)-1H-benzo[d]-imidazol-1-yl)acetohydrazide (5a) and N-(5-bromo-2-hydroxy-benzylidene)-2-(2-(phenylthiomethyl)-1H-benzo[d]-imidazol-1-yl)acetohydrazide (5d) which displayed excellent cancer inhibitory activity against the tested cancer cells (IC(50) 4-17 μM), compared with 5-FU and SU11248. The others have moderate to weak inhibitory activity against the tested cancer cell lines.

Synthesis, antiproliferative activities and in vitro biological evaluation of novel benzofuransulfonamide derivatives.

In a cell-based screen of novel antiproliferative agents, the hit compound 1a, which bears a benzofuransulfonamide scaffold, exhibited broad-spectrum antiproliferative activities against a panel of tumor cell lines. The promising in vitro antiproliferative activity and structural novelty of 1a prompted us to investigate the synthesis of five analogs of 1a and test their antiproliferative activities. The most potent analogue, 1h, exhibited enhanced antiproliferative activities compared with the parent 1a, and exhibited an IC(50) value against NCI-H460 cells of 4.13 μM compared with 4.52 μM for the positive control cisplatin. Flow cytometric analysis revealed that 1h induces significant levels of apoptosis in NCI-H460 cells in vitro at low micromolar concentrations. These results suggest that 1a and analogs based on its benzofuransulfonamide scaffold may constitute a novel class of antiproliferative agents, which deserve further study.

Synthesis and biological evaluation of novel benzamide derivatives as potent smoothened antagonists.

A series of novel benzamide derivatives were prepared and evaluated using cell-based measurements. Among these compounds, 10f significantly inhibited Hedgehog signaling and showed equivalent or more potency than GDC-0449 in different tests. Furthermore, compound 10f potently inhibited the proliferation of Daoy, a medulloblastoma cell line that is reported to be resistant to GDC-0449, which indicated a promising prospect in the treatment of Hedgehog signaling pathway related cancer in clinical trial.

Acidic ionic liquid modified silica gel for adsorption and separation of bovine serum albumin (BSA)

In this work, silica gel (SiO2) was modified with an acidic ionic liquid (Im+·HSO4−) and the product was characterized using infrared spectroscopy, thermogravimetric analysis and elemental measurement. Then it was used in the adsorption of bovine serum albumin (BSA) for the first time. Then the influences of initial concentration, temperature, solid–liquid ratio and pH were investigated. These studies showed that the adsorption equilibrium data fit well with the Langmuir model and the pseudo-second-order model could be used to describe the adsorption kinetics more accurately. The major thermodynamic parameters including the change of enthalpy, entropy and Gibbs free energy indicated that the adsorption was an exothermic and spontaneous process, which was controlled by chemical and physical interactions. The mechanism was also investigated using characterization and comparative experiments. All of the proteins tested reached their maximum adsorbed amount on SiO2·Im+·HSO4− when the pH was around their isoelectric point, and the adsorption capacity was lowered with the increase of protein volume. After the desorption using an aqueous solution of sodium chloride, the SiO2·Im+·HSO4− could be recycled for several times. Finally, the selective adsorption of BSA and bovine hemoglobin from cow blood could be successfully realized under the appropriate pH conditions. This study is aimed to provide a preparative method for the selective adsorption and separation of BSA with a supported ionic liquid. Furthermore, it is expected to enrich the separation materials of proteins and extend the potential functions of ionic liquids.

Magnetic solid-phase extraction based on ferroferric oxide nanoparticles doubly coated with chitosan and β-cyclodextrin in layer-by-layer mode for the separation of ibuprofen

A novel and environmentally-friendly magnetic adsorbent consisting of ferroferric oxide (Fe3O4) nanoparticles, β-cyclodextrin and chitosan was successfully fabricated by layer-by-layer methodology and applied in the magnetic solid phase extraction (MSPE) of ibuprofen. The adsorption results demonstrated that ibuprofen extraction was significantly pH dependent and the optimal pH value was 5.0, which was mainly ascribed to the electrostatic interaction and inclusion complexes between the adsorbent and ibuprofen. The adsorption kinetics of ibuprofen was found to follow a pseudo-second-order kinetic model. Thermodynamic data for ibuprofen adsorption were fitted well by the Freundlich model and the Freundlich constant indicated it was a favorable process. The thermodynamic parameters suggested that the adsorption process was endothermic and spontaneous in nature. Based on the adsorption research, the main factors affecting the MSPE procedure were optimized, including desorption conditions, amount of adsorbents and eluent volume. Under the optimal conditions, the enrichment factor was 182.56. Moreover, the feasibility of the proposed procedure was demonstrated with the extraction and enrichment of ibuprofen from an environmental water sample, and the results indicated that the complex composition of the investigated object did not significantly affect the selectivity of the extraction process.

The adsorption behavior and mechanism investigation of Cr(VI) ions removal by poly(2-(dimethylamino)ethyl methacrylate)/poly(ethyleneimine) gels

The composite hydrogels based on 2-(dimethylamino)ethyl methacrylate (DMAEMA) and poly ethyleneiminexa0(PEI) were prepared by amino radical polymerization and confirmed by Fourier transform infrared (FTIR) spectroscopy and elemental analysis. Then adsorption behavior and mechanism of Cr(VI) ions adsorption on the obtained materials were investigated by scanning electron microscopy, zeta potential determination and thermogravimetric analysis,xa0 etc . The adsorption process was found to follow pseudo-second order kinetics and the Langmuir model, and the maximum adsorption capacity of Cr(VI) ions reached 122.8 mg g -1 . X-ray photoelectron spectroscopy (XPS) and pH analysis revealed that the Cr(VI) ions were adsorbed into the gels through the electrostatic interaction mechanism, and SO 4 2- xa0in the solution had a great effect on the adsorption process. In addition, a high pH and ionic strength could reduce the uptakes of the adsorbate, which could be used for desorption of Cr(VI) ions from the gels.

Catalytic alcoholysis of bagasse cellulose for the total reducing sugars with temperature-sensitive phase-variable ionic liquid

ABSTRACT The separation of cellulose hydrolyzate and ionic liquids (ILs) as well as the recycling of ILs is very plagued and needs to be resolved urgently in cellulose hydrolysis. In this study, a temperature-sensitive phase-variable IL was employed to develop a new conversion method for cellulose. It was found that the IL exhibited favorable catalytic activity over six repeated runs, which only decreased by 9.10%. Additionally, a mechanism for this alcoholysis system was proposed. The study is aimed to provide a new scientific way for the cellulose conversion and extend the application of temperature-sensitive ILs in biomass field.

Hydrolysis of trichosanthin (TCS) catalyzed by imidazolium-based ionic liquids in heating and microwave-assisted modes

Trichosanthin (TCS) is a kind of basic protein separated from Trichosanthes kirilowii Maxim, which is a good food source for human nutrients and has important uses for health. In this study, a series of imidazole-based ionic liquids (ILs) were chosen as catalysts for TCS hydrolysis in both heating and microwave-assisted modes and the hydrolysis was compared with chlorhydric acid and sulfuric acid together with sodium hydroxide for the degree of hydrolysis (DH) of TCS. It was found that the performance of acidic ILs > neutral ILs > basic ILs; [Hmim][HSO4] among the ILs presented the highest DH which was even better than those of inorganic strong acids. Furthermore, the process of hydrolysis was optimized with 3D-response surface methodology (RSM), and the highest degree of hydrolysis could reach to 48.3% (in heating mode) and 93.9% (in microwave-assisted mode). Finally, D001Na type cation-exchange resins were used in the selective adsorption of amino acid products and ILs in an effluent that could be reused. The hydrolysates from TCS showed an enhanced antioxidant activity which was evaluated in three ways. This study could provide a useful foundation for further research and exploitation of TCS.

Corrigendum to “Synthesis and biological evaluation of novel benzamide derivatives as potent smoothened antagonists” [Bioorg. Med. Chem. Lett. 24/5 (2014) 1426–1431]

http://dx.doi.org/10.1016/j.bmcl.2015.06.051 0960-894X/ 2016 Elsevier Ltd. All rights reserved. DOI of original article: http://dx.doi.org/10.1016/j.bmcl.2014.01.006 ⇑ Corresponding authors. Tel.: +86 28 85164063; fax: +86 28 85164060. E-mail addresses: zhaoyinglan@scu.edu.cn (Y.-L. Zhao), xieym@scu.edu.cn (Y.-M. Xie). These two authors contributed equally as first authors. Tian-Ming Wu a, , Dao-Cai Wang b, , Pu Xiang , Jian-Nan Zhang , Ya-Xiong Sang , Hong-Jun Lin , Jie Chen , Gang Xie , Hang Song , Ying-Lan Zhao a,⇑, Yong-Mei Xie a,⇑

DEVELOPMENT OF AN EFFICIENT HPLC METHOD WITH PRE-COLUMN DERIVATIZATION FOR DETERMINATION OF ENANTIOMERIC PURITY OF 2-(AMINOMETHYL)-1-ETHYLPYRROLIDINE

The development of a simple and efficient analytical method for determination of enantiomeric purity of 2-(aminomethyl)-1-ethylpyrrolidine was presented. The method was based on pre-column derivatization of 2-(aminomethyl)-1-ethylpyrrolidine with 4-nitrobenzoic acid completing separation of the enantiomers on high performance liquid chromatographic (HPLC) chiral stationary phase (CSP). After optimizing all the effective parameters, the best performances were achieved on a Chiralcel OD-H analytical column (250 × 4.6 mm) using n-hexane: ethanol (98:2, v/v) containing 0.2% triethylamine as mobile phase with a flow rate of 1.0 mL min-1 at 25°C. Online UV and optical rotation (OR) detection was performed at 254 nm. The parameters which have an effect on chiral separation were investigated, including mobile phase additive, organic modifier type and concentration, column temperature and flow rate. The method was tested for precision, accuracy, linearity, limit of detection (LOD), limit of quantification (LOQ) and robustness. The present method is expected to be accurate, stable, rapid and sensitive and can be used for the determination of the enantiomeric purity of 2-(aminomethyl)-1-ethylpyrrolidine in bulk samples.