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25 January 2007, Volume 23 Issue 1

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Content of Chemical Research in Chinese Universities Vol.23 No.1(2007)

2007, 23(1):  0-0.  doi:

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Articles

Studies on Crystal Orientation of ZnO Film on Sapphire Using High-throughout X-ray Diffraction

HOU Chang-min , HUANG Ke-ke , GAO Zhong-min , LI Xiang-shan , FENG Shou-hua , ZHANG Yuan-tao , ZHU Hui-chao , DU Guo-tong

2007, 23(1):  1-4.  doi:

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The orientation of the nano-columnar ZnO films grown on sapphire using the technique of metal-organic chemical vapor deposition (MOCVD) exhibits deviation because of the mismatch between the crystal lattices of the films and the sapphire substrate. A high-throughout X-ray diffraction method was employed to determine the crystal orientation of the ZnO films at a time scale of the order of minutes based on the general area detection diffraction system(GADDS). This rapid, effective, and ready method, adapted for characterizing the orientation of the nano-columnar crystals is used to directly explain the results of observation of the X-ray diffraction images, by the measurements of the orientations of the crystal columns of the ZnO films along c-axis and in parallel to ab plane.

Synthesis and Surface Modification of CdTe Nanocrystals

ZHUANG Hong , LIU Jing-bo , ZHANG Chun-ling , KONG Xiang-gui

2007, 23(1):  5-7.  doi:

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CdTe nanocrystals were prepared in aqueous solution via the reaction between Cd²⁺ and NaHTe in the presence of mercaptoacetic acid. Interactions between CdTe nanocrystals and phenylalanine were formed via electrostatic/coordinate self-assembly. The photoluminescence intensity of CdTe nanocrystals was improved obviously. The interaction mechanism was discussed and was considered to be surface passivation.

Syntheses, Crystal Structures and Characterization of Two Zeotype Crystals of K₄[Cr₃O(H₂O)₃(OOCH)₆]₂[P₂W₁₈O₆₂]·9.5H₂O and K

ZHANG Xin , YOU Wan-sheng , ZHU Zai-ming , DANG Li-qin , SUN Zhen-gang , ZHENG Xue-fang

2007, 23(1):  8-13.  doi:

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Two novel zeotype crystals, K₄[Cr₃O(H₂O)₃(OOCH)₆]₂[P₂W₁₈O₆₂]·9.5H₂O(1) and K₄[Cr₃O(H₂O)₃·(OOCH)₆][H₃P₂W₁₇Co(H₂O)O₆₁]·20H₂O(2), were synthesized and their structures were determined using X-ray single crystal diffraction. Crystal data: C₁₂H₄₃O_103.5K₄Cr₆P₂W₁₈(1), hexagonal P6(3)/m, a=1.5895(2) nm, b=1.5895(2) nm, c=2.1620(4) nm, α=90°, β=90°, γ=120°, V=4.7305(13) nm³, Z=2, R₁=0.0726, wR₂=0.1542; C₆H₅₇O₉₈K₄Cr₃CoP₂W₁₇(2), hexagonal P6(3)/mmc, a=1.61328(3) nm, b=1.61328(3) nm, c=2.06613(9) nm, α=90°, β=90°, γ=120°, V=4.6570(2) nm³, Z=2, R₁=0.0377, wR₂=0.1070. These crystals were characterized using elemental analysis, IR, TG-DTA, and XRD. It was found that the polyoxometalate anions maintained Wells-Dawson structure for crystal 1 and lacunary Wells-Dawson structure for crystal 2. Thermal analysis showed that crystal 1 lost the water of crystallization at 132 ℃, whereas crystal 2 lost the water of crystallization at 100 ℃. Crystal 1 could reversibly desorb and adsorb water molecules and its crystal structure could be restored after re-adsorbing the water molecules. It was also found from the XRD patterns that the void size of crystal 2 is smaller compared with that of crystal 1, which is attributed to the higher anion charges.

Determination of Pesticide Ethion by Linear Sweep Stripping Voltammetry

QIU Ping , NI Yong-nian , KOKOT Serge

2007, 23(1):  14-17.  doi:

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The presence of the pesticide ethion was determined using an electroanalytical method, i.e., linear sweep stripping voltammetry at a hanging mercury drop electrode in the Britton-Robbinson buffer with pH=8.36, based on its reduction peak observed at -690 mV following its alkaline hydrolysis. The experimental parameters, namely, the preconcentration potential, the preconcentration time, and the scan rate were investigated and -300 mV(vs. Ag/AgCl), 270 s, and 100 mV/s were selected as the optimal values, respectively. The linear relationship between the peak current and the concentration was found to be in the range of 0.02—0.16 mg/L, with a detection limit of 0.0087 mg/L. The proposed method was applied to the determination of ethion in spiked vegetable and fruit samples via a preextraction with anhydrous ethanol.

Association of (S)-Isoserine Derivatives and 2,2,4-Trimethyl-3-hydroxy-4-cyclohexenecarboxylate

WANG Lei , ZHENG Qing-chuan , SONG Zhi-guang , FANG Wei-shuo , LI Ye-zhi , HUANG Hua-min

2007, 23(1):  18-21.  doi:

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Two novel compounds(4a and 4b) were obtained by the association of 2,2,4-trimethyl-3-hydroxy-5-cyclohexenecarboxylate with (S)-isoserine derivatives. The space location of the hydroxyl group of compound 1 was identified via the formation of lactone 6. Fe₂(SO₄)₃·xH₂O was used as the catalyst for the synthesis of lactone 6. The carboxyl group was selectively protected with diazomethane. All the products were characterized via ¹H NMR and mass spectra. The Docking study showed that the associations have the potential therapeutic use of DPP-Ⅳ inhibitor.

Syntheses of Macrocyclic Amides from L-Amino Acid Esters by RCM

ZHAO Bao-xiang , SCHAUDT Marco , BLECHERT Siegfried

2007, 23(1):  22-30.  doi:

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A series of succinate-derived macrocyclic amides(1) was synthesized via ring-closing metathesis(RCM) as the key step. The substrate included 12 to 15 members. The metathesis precursors were obtained from the amide coupling of tert-butyl 3-carboxyhex-5-enoate(2) with numerous side-chain alkenylated amino acid esters of general type(3) derived from L-lysine and L-ornithine.

Copolymerization of Ethylene with Dicyclopentadiene Using a Constrained Geometry Cyclopentadienyl-phenoxytitanium Catalyst

Chun-sheng,ZHANG Yue-tao

2007, 23(1):  31-34.  doi:

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The copolymerization of ethylene with dicyclopentadiene (DCP) in the presence of a constrained geometry tetramethylcyclopentadi-enyl-phenoxytitanium catalyst [2,4-^tBu₂-6-(2,3,4,5-Me₄-Cp)-PhO]TiCl₂, combined with Al(ⁱBu)₃/Ph₃C⁺B(C₆F₅)₄^- cocatalyst system was studied. The copolymers that were formed were characterized by ¹H and ¹³C NMR, differential scanning calorimetry (DSC), SEM, and X-ray diffraction (XRD) analyses. The results of the analysis indicate that the copolymers of ethylene with dicyclopentadiene are amorphous and display two or more melting temperatures in their DSC diagrams. Moreover, the morphologies of the copolymers are quite different from that of polyethylenes.

Synthesis and Mesophase Properties of Intraanular Functionized Shape-persistent Macrocycles Containing Dibenzo[fg,op]naphthacenes

CHENG Xiao-hong , HOEGER Sigurd

2007, 23(1):  35-43.  doi:

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On the basis of the C—C coupling reactions of dibenzo[fg,op]naphthacene bistriflate, which was obtained by the condensation of phenylacetates with 4-aryl-2,6-bis(2-bromo-4-methoxy-phenyl) pyrylium salts followed by palladium-catalyzed dehydrohalogenation, three shape-persistent macrocycles with dibenzonaphthacene corner pieces, a nanometer interior void, and intraanular oligoalkyl side groups were synthesized by the oxidative cyclization of the corresponding bisacetylenes under high-dilution conditions. Their thermotropic liquid crystalline properties were investigated by using polarizing microscopy and differential scanning calorimetry. All the three compounds showed nematic mesophases and belonged to discotic liquid crystals with inverted topology.

Studies on a Novel Minor-groove Targeting Artificial Nuclease: Synthesis and DNA Binding Behavior

YIN Qiang, ZHANG Zhen , ZHAO Yu-fen

2007, 23(1):  44-47.  doi:

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Nucleases play an important role in molecular biology, for example, in DNA sequencing. Synthetic polyamide conjugates can be considered as a novel tool for the selective inhibition of gene expressions and also as potential drugs in anticancer or antiviral chemotherapy. In this article, the synthesis of a novel minor-groove targeting artificial nuclease, an oligopyrrol-containing compound, has been reported. It was found that this novel compound can bind DNA in AT-rich minor groove with high affinity and site specificity. DNA binding behavior was determined by using UV-Vis and CD. It is indicated that compound 6 can enhance the T_m of DNA from 80.4 ℃ to 84.4 ℃ and that it possesses a high binding constant value(K_b=3.05×10.4 L/mol).

Rapid Identification of Bibenzyls of Stemona sessilifolia using Hyphenated LC-UV-NMR and LC-MS Methods

YANG Xin-zhou, YANG Yi-ping, TANG Chun-ping, KE Chang-qiang , YE Yang

2007, 23(1):  48-51.  doi:

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As a part of the ongoing search for new constituents of Stemona species in China, chemical investigation of Stemona sessilifolia, a plant used in the traditional Chinese medicine to treat respiratory disorders, was carried out. To identify the chemical components rapidly, a selected sample of S. sessilifolia containing bibenzyls was tested using LC-ESIMS and analyzed further using stop-flow LC-UV-NMR, which was sensitive for the detection of the main constituents. LC microfractions were collected using the LC-UV-NMR technique and HR-EIMS off-line analysis was carried out on the collected fractions. This chemical screening strategy allowed for the on-line identification of the main constituents of S. sessilifolia and provided information that was useful for a further peak-guided isolation procedure. Using these methods, four bibenzyls were isolated: two known compounds, 3,5-dihydroxy-4-methyl bibenzyl(1) and 3,5-dihydroxy-2'-methoxy-4-methyl bibenzyl(2), and two novel compounds, 3,3'-dihydroxy-5,6'-dimethoxy bibenzyl(3) and 3,5-dihydroxy-2',5'-dimethoxy bibenzyl(4).

Molecular Cloning of a Glycyrrhiza uralensis F. Aquaporin GuPIP1 Up-regulated in Response to Drought, Salt and ABA Stress

WANG Fang , JIANG Yong , FENG Xue-chao , XU Li-na , LI Ming-tang , LIANG Hai-tao , LI Yong-ming , ZHU Na , LIU Yan-li , MA Tong-hui

2007, 23(1):  52-57.  doi:

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A PCR-based homologous cloning strategy was used to identify aquaporin genes from the roots of Chinese licorice(Glycyrrhiza uralensis F.). A 1236 bp cDNA with 870 bp open reading frame encoding a 290 amino acids aquaporin ortholog, GuPIP1, was successfully cloned and characterized. The deduced GuPIP1 protein contains six putative transmembrane domains; two conserved NPA motifs as well as the MIP and PIP family signature sequences. A rabbit polyclonal antibody against N-terminal peptide of GuPIP1 corresponded to a 31 kDa GuPIP1 protein on Western blot of plasma membrane preparation of root tissue. RT-PCR and Western blot analysis indicated the expression of GuPIP1 in the root, leaf, and stem tissues. Thus far, GuPIP1 is the first Glycyrrhiza uralensis F. aquaporin that has been identified at a molecular level. Quantitative real-time PCR analysis showed that the expression of GuPIP1 was up-regulated in response to drought, ABA, and salt stress.

Rapid Selection of Phage Se-scFv with GPX Activity via Combination of Phage Display Antibody Library with Chemical Modification

LIN Feng , LI Ying , YANG Wen-kui , LIANG Bing , MU Ying , SUN Ye , LI Wei , LUO Gui-min

2007, 23(1):  58-63.  doi:

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Glutathione peroxidase(GPX) plays an important role in scavenging reactive oxygen species. A series of catalytic antibodies with GPX activity have been generated by the authors of this study. To obtain humanized catalytic antibodies, the phage-displayed human antibody library was used to select novel antibodies by repetitive screening. Phage antibodies, scFv-B8 and scFv-H6 with the GSH-binding site, were obtained from the library by enzyme-linked immunosorbent assay(ELISA) analysis with 4 rounds of selection against their respective haptens, S-2,4-dinitriphenyl t-butyl ester(GSH-s-DNP-Bu) and S-2,4-dinitriphenyl t-hexyl ester(GSH-s-DNP-He). Nevertheless, several studies need to be conducted to determine whether scFv-B8 and scFv-H6 possess GPX activity. To enhance the speed of the selection, selenocysteine(Sec, the catalytic group of GPX) was incorporated directly into the phages, scFv-B8 and scFv-H6, by chemical mutation to form the phages Se-scFv-B8 and Se-scFv-H6. The GPX activities were found to be 3012 units/μmol and 2102 units/μmol, respectively. To improve the GPX activity of the phage Se-scFv-B8, DNA shuffling was used to construct a secondary library and another positive phage antibody scFv-B9 was screened out by another panning against GSH-s-DNP-Bu. When Sec was incorporated via chemical mutation into the phage antibody scFv-B9, its GPX activity reached 3560 units/μmol, which is 1.17-fold higher than the phage antibody Se-scFv-B8 and almost approached the order of magnitude of native GPX. The rapid selection is the prerequisite for generating humanized Se-scFv with GPX activity.

Construction of Recombinant Fowlpox Virus(rFpv) Expressing HIV-1 Gag-pol Protein

TENG Hong-gang, LÜ Shuai-ran, LIU Da-wei, JIANG Chun-lai, ZHANG Xi-zhen, YU Xiang-hui , KONG Wei

2007, 23(1):  64-68.  doi:

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The induction of human immunodeficiency virus(HIV)-specific T-cell response is generally considered as critical to the development of effective immunity to HIV type 1(HIV-1). Recombinant Avipoxvirus vectors are used widely for vaccination against HIV-1, where the induction of a cytotoxic CD8+T-cell(CTL) response seems to be an important component of protective immunity. A recombinant fowlpox virus(rFPV/Gag-pol) expressing the Gag-pol protein of HIV was constructed and characterized. The specific expression protein in CEF cells infected by recombinant fowlpox and the specific antibody in the sera of mice immunized with rFPV were analyzed via Western-blot.

Chemical Chaperones Increasing Expression Level of Soluble Single-chain Fv Antibody(scFv2F3)

DU Xiu-bo , SUN Ye , LIN Feng , ZHENG Ke-yan , WANG Ke-wei , LIN Ting-ting , LIU Jun-qiu , SHEN Jia-cong , LUO Gui-min

2007, 23(1):  69-75.  doi:

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Glutathione peroxidase(GPX) is a selenoenzyme that protects the biomembrane and other cellular components against oxidative damage. The selenium-containing single chain Fv fragment of monoclonal antibody 2F3(Se-scFv2F3) is a kind of GPX mimic and it has a wide clinical applications because of its high activity and low antigenicity. Se-scFv2F3 is generated by the chemical modification of the single chain Fv fragment of monoclonal antibody 2F3(scFv2F3), which can be expressed in E. coli. In this article, the effect of chemical chaperones, such as glycerol, glucose, and β-cyclodextrin added to the culture medium, on the expression of soluble scFv2F3 was investigated. The expression level was evaluated by the determination of soluble scFv2F3 contents in the whole cell lysates. The results suggest that both glycerol and β-cyclodextrin greatly increase the expression level of soluble scFv2F3, and β-cyclodextrin is found to be more effective compared with glycerol. Glucose has a slight effect on the expression level of soluble scFv2F3. This is the first example, wherein β-cyclodextrin has been used as a chemical chaperone during the cell culture to improve the expression level of recombinant proteins. In addition, chemical chaperones are found to decrease the toxic effect of IPTG on cells.

Tobacco-specific Carcinogen 4-(Methylnitrosoamino)-1-(3-pyridyl)-1-butanone(NNK) Activating ERK1/2 MAP Kinases and Stimulating Proliferation of Human Mammary Epithelial Cells

CHEN Zhi-bo , AN Yang , WANG Zhe , ZHANG Bo-xun , LIU Lan-ying

2007, 23(1):  76-80.  doi:

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Cigarette smoking is correlated with the development of various cancers. 4-(Methylnitrosoamino)-1-(3-pyridyl)-1-butanone(NNK) is one of the major tobacco-specific carcinogens in the cigarette smoke, which increases the risk of breast cancer. In the present study, it was demonstrated that NNK rapidly activated ERK1 and ERK2 MAP kinases in human normal mammary epithelial cells. It was found that there are two different routes for the activation of ERK1/2 with NNK. One is from nicotinic receptor nAchR to MEK1/2, and the other is from tyrosine kinase containing receptor to MEK1/2. The tobacco-specific carcinogen NNK shows a strong proliferative effect on normal human mammary epithelial cells and cancer mammary epithelial cells.

Physicochemical Properties and Evaluation of Microemulsion Systems for Transdermal Delivery of Meloxicam

YUAN Yue , LI San-ming , YU Li-min , DENG Pan , ZHONG Da-fang

2007, 23(1):  81-86.  doi:

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Microemulsion systems, composed of water, isopropyl myristate(IPM), polyoxyethylene sorbitan trioleate(Tween 85), and ethanol, were investigated as transdermal drug delivery vehicles for a lipophilic model drug(meloxicam). The purpose of this study was to investigate the physicochemical properties of the tested microemulsion and to find the correlation between the physicochemical properties and the skin permeation rate of the microemulsion. Pseudo-ternary phase diagram of the investigated system at a constant surfactant/cosurfactant mass ratio(K_m=1:1) was constructed by titration at 20 ℃, and the five formulations were selected for further research in the o/w microemulsion domains. The values of electrical conductivity and viscosity showed that the selected systems were bicontinuous or non-spherical o/w microemulsion, and the electrical conductivity and viscosity were increased with increasing the content of water. These results suggest that the optimum formulation of microemulsion, containing 0.375 meloxicam, 5% isopropyl myristate, 25% Tween 85, 25% ethanol, and water, showed the maximum permeation rate. It had a high electrical conductivity, small droplet size, and proper viscocity.

Quantum Chemical Investigations on Electron Transport Characteristics of Porphyrin and Metal-porphyrin

OUYANG Sheng-de , YI Yuan-ping , GENG Hua , SHUAI Zhi-gang , LUO Yi

2007, 23(1):  87-91.  doi:

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Recently, molecular electronics has become increasingly important. By applying the hybrid density functional theory coupled with the Green's function method, the current-voltage characteristics of the molecular junctions composed of gold-porphyrin-gold and gold-copper porphyrin-gold were investigated. The role of the metal coordination effect in organic molecular electron transport was highlighted. Although the thresholds of the bias voltage for both molecules were almost the same, approximately 0.9 V, the metal compound showed a larger increase in current because of the metal-coordination-enhanced molecule-electrode coupling in the frontier molecular orbitals.

Luminescent Properties of Mercury-taining Diethynylfluorene Derivatives

LIAO Yi, , SHI Li-li , FENG Ji-kang , YANG Li , REN Ai-min

2007, 23(1):  92-95.  doi:

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Excited state structures and spectroscopic properties of mercury(Ⅱ) complexes, Hg-TFT(1) and its electron-withdrawing substituents Hg-TFOT(2), Hg-TFCNT(3), where TFT=diethynylfluorenyl, TFOT=diethynyl-fluorenone, and TFCNT=diethynyl-[9-(dicyanomethylene)fluorene], were studied using singlet excitation configuration interaction(CIS) and time-dependent density functional theory(TDDFT) methods. The results of the theoretical calculations indicate that the electron-withdrawing substitutions lead to a significant decrease in the energy gap between the ground state and the first excited states. In the case of Hg-TFCNT, the second singlet excited state(S₂) may contribute to the luminescence because of its large S₁-S₂ separation.

Quantum Wave Packet Studies on F+HBr Reaction

QUAN Wei-long, , TANG Ping-ying , TANG Bi-yu , HAN Ke-li

2007, 23(1):  96-100.  doi:

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Time-dependent quantum wave packet calculations were carried out for the F+HBr reaction on the latest London-Erying-Polanyi-Sato potential energy surface constructed by Persky et al.. The calculated reaction probabilities dramatically increase near the zero collision energy and then slightly decrease with increasing collision energy, which corresponds well to the behavior of a barrierless reaction. The effects of reagent HBr excitation were examined, it is shown that both the vibrational and the rotational excitations of reagent HBr have a negative effect on the reactivity of F+HBr. The integral cross-section for the ground state of the reagent HBr decreases at a low collision energy and then becomes plat with increasing collision energy, which is reasonable for the feasibility of such an exothermal reaction. The rate constant that was obtained is slightly higher than that obtained in the quasi-classical trajectory calculation.

Self-assembling Behavior of Amphiphilic Copolymer Containing Cross-linked Hydrophilic Block in Ethanol

WANG Ying, ZHANG Jun-hu, WANG Zhan-hua, ZHANG Kai, WANG Zheng, YU Wen-zhi , YANG Bai

2007, 23(1):  101-104.  doi:

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The self-assembly behavior of the amphiphilic block copolymer poly(methyl methacrylate)-block-poly(lead dimethacrylate)(PMMA-b-PLDMA) with cross-linked hydrophilic block(PLDMA) in ethanol was investigated. The results show that the
size and morphology of the resulting micelle or micellar aggregates are ascribed to the content of ethanol and the nature of the solvent mixture. PbS nanoparticles were formed in the micelle by in situ reaction with H₂S gas. The morphology and size of the self-assembly objects were investigated using scanning electron microscopy(SEM) and transmission electron microscopy(TEM).

Research Notes

Hydrothermal Synthesis and Crystal Structure of Manganese(Ⅱ) Coordination Polymer Assembled by 4-Sulfophthalate and 4,4'-Bipyridine

WANG Qing-wei , LI Xiu-mei , GAO Guang-gang

2007, 23(1):  105-108.  doi:

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The multi-carboxylate ligand was selected, and a three-dimensional supramolecular coordination polymer {[Mn₂(4-sphth)₂(4,4'-bpy)₄·(H₂O)₄][Mn(4,4'-bpy)₂(H₂O)₄]}_n·7nH₂O(1) was synthesized. According to the available data, compound 1 represents the first example of metal-based supramolecular framework constructed from mixed 4-sulfophthalic acid and linear 4,4'-bpy ligands.

Determination of N-Methylcarbamate Pesticides in Vegetables by Solid-phase Extraction and Pressurized Capillary Electrochromatography

WU Xiao-ping , WANG Ling , XIE Zeng-hong , YAN Chao , CHEN Guo-nan

2007, 23(1):  109-115.  doi:

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Several typical NMCs pesticides(namely, methomyl, aldicarb, carbofuran, pirimicarb, and carbaryl), which were popularly used safely in food, were selected for the pCEC investigation for SPE extraction from vegetables prior to analysis. The optimization of the working conditions was given and discussed, and the performance of this SPE-pCEC-UV method in sample analysis was evaluated.

Application of Short-wave Near-infrared Reflectance Spectroscopy in Controlling Extract of Fructus Cnidii Using Supercritical Carbon Dioxide

MI Hong , GUO Ye , LI Wen-liang , Qu Nan , DOU Ying , REN Yu-qiu , REN Yu-lin

2007, 23(1):  116-119.  doi:

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Three models of original spectrum and two models of pretreated spectra(first-derivative spectrum and standard normal variate, respectively) of osthol and imperatorin were established. It has been demonstrated that it is possible to obtain excellent results in solving multivariate calibration problems via ANN.

Syntheses, Structure and Biological Activities of 2-(1H-Benzo[1,2,3]triazole-1-yl)-1-(3-methyl-4-bromobiphenyl)-2-(1H-1,2,4-triazole-1-yl)ethanone

ZHANG Shu-sheng, WAN Jun, LI Xue-mei, LI Chun-li , XU Liang-zhong

2007, 23(1):  120-122.  doi:

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To search for novel triazole compounds with a higher bioactivity, the title compound containing triazole and benzotriazole, which displays a high selectivity, good oral activity, and high plant growth-regulating activities, was synthesized and characterized using IR, ¹H NMR, elemental analysis, and single crystal X-ray diffraction analysis. The biological activities were tested.