Chemical Research in Chinese Universities

Content of Chemical Research in Chinese Universities Vol.24 No.1(2008)

2008, 24(1): 0-0. doi:

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Sonochemical Preparation of Micro- and Nanometer Cu₂O

WANG Ling, , ZHANG Xiao-xia , YUAN Hong-ming , CHEN Yan , DONG Zhong-ping , PANG Guang-sheng , FENG Shou-hua

2008, 24(1): 1-3. doi:

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Cu₂O particles with different morphologies and scales were prepared sonochemically on the solid-liquid interface of CuCl and water, by adjusting the reaction factors. The products were characterized by powder X-ray diffraction(XRD) and scanning electron microscopy(SEM). The formation and morphology of Cu₂O crystals were influenced by high-intensity ultrasound, reaction temperature, and addition of CuCl. The results indicate that micrometer Cu₂O was crystallized in cubic and octahedral shapes, whereas, nanometer Cu₂O was not produced in well-shaped crystals.

Synthesis, Crystal Structure, and Catalytic Performance of 2,6-Bis[1-(2,4,6-trimethylphenylimino)ethyl]pyridine Nickel(II) Complex

FAN Rui-qing , YANG Yu-lin , LÜ Zhi-wei

2008, 24(1): 4-7. doi:

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A novel nickel(II) complex Ni[L]Cl₂·CH₃CN(1) containing the tridentate ligand 2,6-bis[1-(2,4,6- trimethylphenylimino)ethyl]pyridine(L) has been synthesized. The crystal structure of complex 1 was determined by single crystal X-ray diffraction analysis. The catalytic activity of complex 1 for the polymerization of ethylene was studied under activation with methylaluminoxane(MAO).

Novel Strategy for Synthesis of High Quality CdTe Nanocrystals in Aqueous Solution

YAN Yu-xi, MU Ying, FENG Guo-dong, ZHANG Lei, ZHU Lin-lin, XU Ling, YANG Rui , JIN Qin-han

2008, 24(1): 8-14. doi:

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A novel aqueous route for the synthesis of high-quality CdTe nanocrystals(NCs) is presented in this article. With both glutathione(GSH) and cysteine[n(GSH):n(cysteine)=1:3] as stabilizers, high-quality CdTe NCs with controllable photoluminescence(PL) wavelength from 500 to 630 nm can be prepared within 4 h. As-prepared CdTe NCs show higher photoluminescence quantum yields(PLQY) compared with CdTe NCs prepared via other aqueous methods. When the fluorescent emission peak appeared in orange-red window, the PLQY reaches 70% or above at room temperature without any post-preparative treatment.

Synthesis, DNA-binding, and Photocleavage of 2,3-Di-2-pyridylquinoxaline-silver(I) Complex

WANG Xiu-li , FANG Jia-ni, BI Yan-feng, LIN Hong-yan , LIU Guo-cheng

2008, 24(1): 15-19. doi:

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A new dinuclear complex, [Ag(L)(CH₃CN)]₂(ClO₄)₂•2H₂O(L=2,3-di-2-pyridylquinoxaline), was prepared and characterized by elemental analyses, IR spectroscopy, and single-crystal X-ray diffraction analyses. The interaction of the complex with calf thymus DNA(CT-DNA) was investigated by absorption, fluorescence spectroscopies, and viscosity measurement. The results suggested that the complex was bound to DNA via an intercalative mode. The intrinsic binding constant value K_b was found to be approximately 1.48×10³ L•mol^–1. Moreover, the Ag(I) complex could cleave the plasmid pUC19 DNA from the supercoiled Form I to the nicked Form II under irradiation at 365 nm.

Synthesis, Characterization, and Electrochemical Property of Nanometer Porphyrin Dimer

ZHENG Wen-qi , SHAN Ning , WANG Xing-qiao

2008, 24(1): 20-23. doi:

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A nanometer porphyrin dimer was synthesized with fumaryl chloride as a bridge-linked reagent. The characterization was carried out with elemental analyses, ¹H NMR, UV-Vis, and IR spectrometries, and then the electrochemical properties of the porphyrins were studied. The authors found that there was moderate electronic communication between the two porphyrin rings in the nanometer porphyrin dimer.

Immunosensor Based on Surface Plasmon Resonance for Antigen Recognition

JIN Wei , MU Ying , ZOU Xiang-yu , JIN Qin-han,

2008, 24(1): 24-28. doi:

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A novel immunosensor based on surface plasmon resonance(SPR) has been developed for the recognition of antigen. The sensor was designed on the basis of the fixed angle of incidence and measuring the reflected intensities in a wavelength range of 430―750 nm in real-time. An ultra-bright white light-emitting diode(LED) was used as the light source. Molecular self-assembling in solution was used to form the sensing membrane on gold substrate. It has been seen that the sensitivity of the SPR sensor with 3-mercaptopropionic acid(MPA)/protein A(SPA) sensing membrane is considerably higher than that with MPA or SPA modified sensing membrane. The kinetic processes on the sensing membrane were studied. The human B factor(Bf), an activator of complement 3(C3), was recognized among the other antigens. This sensor can also be used for other antigen/antibody or adaptor/receptor recognition. Under optimized experimental conditions, the sensor has good selectivity, repeatability, and reversibility.

First-order Derivative Spectrophotometry for the Determination of Vitamin C in Medicament

MENG Qing-fan, TENG Le-sheng, JIANG Chao-jun, An Jin-shuang, LI Lei, LU Jia-hui , TENG Li-rong

2008, 24(1): 29-31. doi:

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A novel method for the determination of vitamin C(Vc) is proposed in this article. After the reaction with Folin-Ciocalteau reagent at ambient temperature, Vc solution was scanned at 750―1100 nm, and its first-order derivative spectrum were obtained from the original spectrum. The values of derivative selected at 995 nm were used for determination. It was proved that Vc could quickly react with Folin-Ciocalteau reagent within 5 min and the product was quite stable for a long time. The conditions required for this method is not very complicated, its precision and accuracy are similar to those of the iodometric titration described in Chinese Pharmacopoeia, and the limit of detection is 0.312 g/mL. The determination of the results of vitamin C tablet, pill, and injection demonstrates that this method has wide pharmaceutical applications.

Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing Thiadiazol Moiety

GUO Wan-cheng, LIU Xing-hai, LI Yong-hong, WANG Su-hua , LI Zheng-ming

2008, 24(1): 32-35. doi:

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Thirteen novel sulfonylureas containing thiadiazole moiety were synthesized in a two-step reaction. Their structures were determined using IR, ¹H NMR, HRFTMS, and elemental analysis. Herbicidal activities of these compounds were determined in the green house bio-assay. The results show that four compounds among them exhibit some activity toward four tested herbs.

Tetramethylguanidium Lactate Ionic Liquid: Catalyst-free Medium for Michael Addition Reaction

LIANG Da-peng, XIN Xin, DUAN Hai-feng, YIN Yan-zhen, GAO Han, LIN Ying-jie , XU Jia-ning

2008, 24(1): 36-41. doi:

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A catalyst-free, facile and efficient Michael addition reaction of active methylene compounds as well as nitromethane with chalcones catalyzed by guanidinium lactate ionic liquid was done. A series of chalcones, nitromethane, and active methylene compounds were converted smoothly to the corresponding products in high yields. The simple procedure, very mild conditions, high yields, and reuse of the IL without any loss of catalytic activity make this protocol considerably attractive for academic researches and practical applications.

Synthesis and Anti-tumor Activity of Novel Amide Derivatives of Ursolic Acid

LIU Dan , MENG Yan-qiu , ZHAO Juan , CHEN Li-gong

2008, 24(1): 42-46. doi:

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Ursolic acid was modified at C3 and C28 position to obtain fourteen derivatives including twelve novel compounds, and their chemical structures were characterized by IR, ¹H NMR and MS. Cell growth inhibitory effects of the derivatives against Hela cell were evaluated by MTT assay. All these derivatives were found to have stronger cell growth inhibitory than their parent compound, ursolic acid. The derivatives with a substituted acetyl group at C3 hydroxyl group show better activities than those with an unsubstituted hydroxyl group.

Synthesis and Biological Evaluation of Novel Tricyclic Oximino Derivatives as Antitumor Agents

GUO Shu-chun, ZHAO Yan-fang, LI Rong-dong, XIE Li-jun, YANG You-bin , GONG Ping

2008, 24(1): 47-53. doi:

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A series of novel alkylthio/sulfinyl-8H-thieno[2,3-b]pyrrolizin-8-oximino derivatives V₁―VIII₁₅ were designed and synthesized as antitumor agents. Their structures were confirmed using IR, ¹H NMR, elemental analysis, and MS. The antitumor activities of all the target compounds were tested by the MTT method in vitro against Bel-7402, HT-1080, SGC-7901, and A549 Cell Lines. Among them, compound VI₉ displayed a promising antitumor activity superior to that of Cisplatin.

Sulfonyl Imidazoles as Reagents for the Preparation of Sulfonates and Sulfonamides

REN Yu-jie, GUI Bin, WU Hai-xia , SUN Xiao-bin

2008, 24(1): 54-57. doi:

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Several new sulfonates and sulfonamides were synthesized with sulfonyl imidazoles as reagents. These compounds were characterized by ¹H NMR. The melting points of all solids synthesized were obtained on Fisher-Johns Melting Point Apparatus.

Novel Method for the Enantioselective Synthesis of β-Lactams

YUAN Qing, JIAN Shan-zhong , WANG Yan-guang

2008, 24(1): 58-64. doi:

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A novel method for the enantioselective synthesis of β-lactams is described in this study. 2,3-Dihydrobenzooxazin-4-one derived from salicylamide and L-menthone was used as the chiral auxiliary, which reacted with α-bromo-acyl bromides in the presence of pyridine to give carboximides 2. The stereo-controlled Reformatsky-type reactions of carboximides with imines yielded the corresponding trans β-lactams with high enantioselectivities(e.e. 75%―86%) and high chemical yields(63%―85%), meanwhile, the chiral auxiliary dihydrobenzooxazin-4-one was released and recovered.

Effects of Siqi Decoction on Concentration of Nitric Oxide and Activity of Nitric Oxide Synthase in Blood Serum of Rats with Myocardial Ischemia

SU Yan-bin ，LI Zheng-qiang ，SU Yan-wen , ZHANG Fen-rong

2008, 24(1): 65-68. doi:

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To study the effects of Siqi decoction on rats with Myocardial Ischemia, the model of Myocardium Ischemia was made for the Wistar rats cured with posterior pituitary injection through vein in tail. Siqi decoction, Diaoxinxuekang(DK) and Fufangdanshenpian(FD), the latter two drugs of which were effective TCM drugs of anti-Myocardial Ischemia at present, were administrated to the rats with Myocardium Ischemia for 5 days to compare the effect of anti-Myocardium Ischemia as reference drugs by measuring the changes of NO concentration and activity of NOS in the rat blood serum with Myocardial Ischemia. There was a remarkable increase in the NO concentration and activity of NOS in serum in Siqi decoction groups compared with those in control group(p<0.05). The results of the prevention group in experiment of Siqi decoction are better than those of the cure group. Siqi decoction was really fit for Myocardium Ischemia via increasing NO concentration by stimulating the activity of NOS in serum. The effect of Siqi decoction against Myocardium Ischemia in preventive group is better than the curative that of Siqi decoction in the curative group.

Molecular Design and Immunogenicity of a Multiple-epitope FMDV Antigen and DNA Vaccination

MA Ming-xiao , JIN Ning-yi , LIU Hui-juan , ZHENG Min , YIN Ge-fen , TIAN Ming-yao , JIN Ming-lan , LU Hui-jun , SHEN Guo-shun , ZHU Guang-ze , JIN Hong-tao , JIN Kuo-shi

2008, 24(1): 69-74. doi:

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This article reports the design and construction of a multiple-epitope foot and mouth disease virus (FMDV) antigen, designated as OAAT. This recombinant antigen consists of the structural protein VP1 genes from serotypes A and O FMDV, five major VP1 immunodominant epitopes from two genotypes of Asia1 serotype, and three Th2 epitopes originating from the nonstructural protein, three ABC gene and structural protein VP4 gene. Expressions of target gene from these plasmids in HeLa cells were verified by Western-blot. BALB/c mice were immunized intramuscularly with the DNA vaccines thrice every two weeks. We found that pA could induce simultaneously specific antibodies against serotypes A, Asia1, and O FMDV. Compared to those of the controls, the spots of FMDV-specific IFN-γ and cytotoxic activity from mice immunized with pA were significantly increased. pA provided full protection in 2/4 guinea pigs from challenge with FMDV O/NY00 and Asia1/YNBS/58, respectively. The results show that although pA did not give full protection in 100% immunized guinea pigs from challenge with type O and Asia1 FMDV, respectively, OAAT may be potential immunogen against FMDV and pA may be potential DNA vaccines against FMDV.

Translational Enhancer of Tobacco mosaic virus Enhancing Expression of Hepatitis B Surface Antigen in Transgenic Panax ginseng C. A. Meyer Callus

GAO Zheng-lun , SHENG Jun , HAO Shu-mei , LIU Dan , LIU Xiao-yu , JI Hai-bin , LI Juan , ZHANG Xian-ping

2008, 24(1): 75-79. doi:

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The 5′-nontranslated leader(omega sequence) of Tobacco mosaic virus(TMV) was used as a translational enhancer sequence in the expression of the hepatitis B surface antigen(HBsAg) gene in transgenic ginseng callus cultures. The adr subtype HBsAg gene was placed under the control of the Cauliflower mosaic virus(CaMV) 35S promoter linking to the TMV leader sequence. The antisense omega sequence was used in a control construct. The resulting constructs cloned in the binary vector pBI121 were used to transform the ginseng callus tissue via the Agrobacterium-mediated procedure. The integration and expression of the HBsAg gene were evaluated by PCR and western blot, respectively. Enzyme-linked immunoassays(ELISA) using a monoclonal antibody directed against human serum-derived HBsAg revealed a three to four-fold enhanced expression of HBsAg in ginseng cells conferred by the TMV omega element.

Effects of Vitamin E on the Activities of Protective Enzymes and Membrane Lipid Peroxidation in Leymus Chinensis under Drought Stress

GU Jie , LIU Gong-she , GUO Juan , ZHANG Jin

2008, 24(1): 80-83. doi:

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Leymus chinensis seedlings were treated with 0.05―10 mmol/L vitamin E under osmotic stress in the presence of polyethylene glycol(PEG) as the stress reagent. The effects of the different concentrations of exogenous vitamin E on the activities of SOD, POD and free proline, and the MDA contents under drought stress were examined so as to ascertain the mechanism of Leymus chinensis resistance to drought stress and explore the possible preventive measures. The results indicate that the activities of SOD and POD decreased but the free proline and MDA contents increased as drought stress was accentuated, showing an enhancement of oxidative stress that may cause a decline in membrane stabilization. However, the activities of SOD and POD and the free proline content increased, whereas the MDA content reduced in Leymus chinensis pretreated with vitamin E in comparison with that of the control. This indicates that exogenous vitamin E enhanced the antioxidation of Leymus chinensis seedlings. It suggests that cytomembrane can be protected from damage by increasing the free proline content and the activities of SOD and POD that result in enhancing the drought resistance of Leymus chinensis seedlings.

Transferrin and Its Isoforms from Normal Human Serum Revealed by Several Analytical Techniques

ZHUO Hui-qin, , HUANG He-qing, , JIN Hong-wei , HUANG Lin

2008, 24(1): 84-91. doi:

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Transferrin(TF) and its isoforms have been widely reported via various analytical techniques, including a noticeable increased number of isoforms with low content of sialic acid(asialo-, monosialo-, and disialo-transferrin) and asialo-TF as well as disialo-TF, with one or several oligosaccharides released in human serum transferrin(hTf). Here, hTf has been purified by native gradient polyacrylamide gel electrophoresis(PAGE_NG) before use. The hTf extracted with the electron-transfer approach showed a single subunit band(77.1 Da) in the SDS-PAGE gel, but it exhibited two bands in the native and denatured isoelectric focusing(IEF) gels, namely, hTf-2Fe³⁺ and apo-hTf, without finding any other transferrin isoforms. A reversed phase HPLC(RP-HPLC) equipped with a C18 column effectively separated hTf and its polymers and combined off-line techniques, including peptide mass fingerprinting(PMF), matrix-assisted laser desorption/ionization time-of-flight mass spectrometry(MALDI-TOF-MS) and database search, and identified the high homology among hTf, apo-hTf, and their isoforms. Moreover, the elution solution consisting of acetonitrile and formic acid could easily denature both hTf and apo-hTf to form various isoforms during separation with HPLC, indicating that chemical factors lead to the formation of various isoforms in transferrin, artificially, during extraction and separation. The authors claimed that only two transferrin isoforms existed in the NHS, namely, hTf-2Fe³⁺ and apo-hTf, which could be employed in biomarkers, to distinguish the healthy population from many disease sufferers, such as, carbohydrate-deficient transferrin(CDT).

Natural Compound Curcumin Corrects the Gating Defect of G551DMutant Cystic Fibrosis Transmembrane Conductance Regulator

HAO Li-ming, , LIU Xin , XU Li-na , ZHU Na , LIN Sen , HOU Shu-guang , ZHOU Na , SHI De-cheng , SHANG De-jing , MA Tong-hui , YANG Hong

2008, 24(1): 92-95. doi:

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In the present study, we identified the natural compound curcumin to be an effective G551D-CFTR activator by cell-based fluorescent assay and electrophysiological measurement. We demonstrated that curcumin can restore the impaired chloride conductance of G551D mutant CFTR. The activity is rapid, reversible, and cAMP-dependent. Our study identified a new natural lead compound for the pharmacological therapy of cystic fibrosis caused by G551D mutation of CFTR.

Kinetics and Mechanism of the Photo-oxidation of Thiophene by O₂ Adsorbed on Molecular Sieves

ZHAO Di-shun , LI Fa-tang, , ZHOU Er-peng , SUN Zhi-min

2008, 24(1): 96-100. doi:

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Photochemical oxidation of thiophene in n-octane/water extraction system using O₂ as oxidant was studied. The reaction mechanism of thiophene oxidation was proposed. Results obtained here can be used as the reference for the oxidative desulfurization of gasoline because thiophene is one of the main components containing sulfur in fluid catalytic cracking gasoline. Thiophene dissolved in n-octane was photodecomposed and removed into the water phase at ambient temperature and atmospheric pressure. A 500 W high-pressure mercury lamp (main wave length 365 nm, 0.22 kW/m) was used as light source for irradiation, and air was introduced by a gas pump to supply O₂. Thiophene can be photo-oxidized to sulfone, oxalic acid, SO₄²⁻, and CO₂. The desulfurization yield of thiophene in n-octane is 58.9% under photo-irradiation for 5 h under the conditions of air flow at 150 mL/min and V(water):V(n-octane)=1:1. It can be improved to 92.3% by adding 0.15 g zeoliteartificial into 100 mL reaction system, which is the adsorbent for O₂ and thiophene. And under such conditions, the photo-oxidation kinetics of thiophene with O₂/zeoliteartificial is first-order with an apparent rate constant of 0.5047 h^-1 and a half-time of 1.37 h. The sulfur content can be depressed from 800 μL/L to less than 62 μL/L.

Effect of 3-Amino-5-mercapto-1,2,4-triazole on Electroless Nickel Deposition

LIU Hai-ping, LI Ning, BI Si-fu, LI De-yu , ZOU Zhong-li

2008, 24(1): 101-105. doi:

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The effects of organic additive, 3-amino-5-mercapto-1,2,4-triazole (AMTA) on bath stability, deposition rate, reaction activation energy, and Ni-P coating composition in acidic electroless nickel plating were investigated. Polarization curve method and infrared reflection spectroscopy were used to analyze the mechanism of the effect of AMTA on electroless nickel deposition. It was observed that AMTA improved bath stability, decreased the deposition rate, and increased the reaction activation energy. It was also revealed that AMTA decreased the phosphorus content and increased the sulfur content in Ni-P coating. In addition, AMTA inhibited the anodic oxidation of hypophosphite and accelerated the cathodic reduction of Ni²⁺. Infrared reflection spectroscopy result indicates that AMTA was adsorbed on the surface of Ni-P and interacted with Ni²⁺ to form an AMTA-Ni²⁺ compound. On the basis of the results of this study, the mechanism of the effect of AMTA on electroless nickel deposition was deduced.

New Chiral Calixarene Derivatives: Syntheses and Their Chiral Recognition Toward Amino Acids by UV-Vis Spectroscopy

GU Jin-ying , HE Wan-ping , SHI Xian-fa , JI Liang-nian

2008, 24(1): 106-109. doi:

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Three novel types of chiral calixarene derivatives 5, 8, and 10 were designed and synthesized by introducing chiral units to parent calixarenes. Their chiralities were confirmed by rotational analysis. Chiral recognition properties of these host compounds towards L- and D-threonine were studied by UV-Vis spectroscopy. The results indicated that calixarene derivatives 5 and 8 exhibited good chiral recognition capabilities toward L- or D-threonine. Although calixarene derivative 10 had no evident chiral recognition ability, the supramolecules of calixarene derivative 10 with L- or D-threonine showed a hypochromic effect or hyperchromic effect respectively. Therefore, calixarene derivative 10 might serve as a good chiral UV-indicator.

Mechanistic Aspects of Monomer, Polymer Formation, and Synthesis of PQ-Alt-Dialkyl-fluorene Conjugated Copolymer

Muddasir Hanif , LU Ping , ZHENG Yan , LI Mao , XIE Zeng-qi , MA Yu-guang , LI Di , LI Jing-hong

2008, 24(1): 110-115. doi:

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Suzuki coupling reaction is widely used in the construction of conjugated polymers; however, there is still no report describing the mechanism and coupling of 9,10-phenanthrenequinone(PQ) building blocks via Suzuki reaction because PQ is sensitive to bases and light. Herein is reported the efficient Suzuki coupling of PQ with 9,10-dialkylfluorene with Na₂CO₃ as basic species and high molecular weight PQ-Alt-Dialkyl-Fluorene conjugated copolymer obtained in an yield of 42%. Based on the characterization data and well-accepted literature, we proposed a step-by-step mechanistic explanation for the formation of the PQ containing alternating conjugated copolymer.

Poly(vinylidene fluoride)/Clay Nanocomposites by Melt Compounding

SONG Yu-ming , ZHAO Zhu-di , YU Wen-xue , ZHENG Wei-tao , LI Bo , YANG Xiao-wei , CHEN Xin-fang

2008, 24(1): 116-119. doi:

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The crystalline structures, morphologies, and mechanical properties of poly(vinylidene fluoride)/clay nanocomposites were studied using X-ray diffraction(XRD), transmission electron microscopy(TEM), Fourier transform infrared spectroscopy(FTIR), polarized optical microscopy(POM), and tensile tests. The results of XRD and TEM show that organoclays are dispersed in the poly(vinylidene fluoride)(PVDF) matrix. A clay-induced crystal transformation from α-phase to β-phase of PVFD was confirmed by XRD and FTIR. Clay layers restricted the growth of spherulite. The tensile tests indicate that the tensile modulus and yield strength as well as the elongation at break decrease when clay is loaded.

Zinc Borohydride-Ionic Liquid: Stable and Efficient System for Reductive Reaction of Aldehydes with Primary Amines to Corresponding Secondary Amines

NIAN Bao-yi , XU Gang , WU Jiang-ping , YANG Li-rong

2008, 24(1): 120-122. doi:

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Zinc borohydride in ionic liquids was found to be a stable and efficient system for the reductive amination of aldehydes with primary amines under mild and neutral reaction conditions to afford the corresponding secondary amines in excellent selectivity and good yield.

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