Yuguo Du

Chinese Academy of Sciences, Peping, Beijing, China

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Publications (115)245.4 Total impact

  • Tetrahedron. 11/2014; 70(44):8231–8235.
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    ABSTRACT: A large quantity of toxic chemical pollutants possibly remains in reclaimed water due to the limited removal efficiency in traditional reclamation processes. It is not enough to guarantee the safety of reclaimed water using conventional water quality criteria. An integrated assessment method based on toxicity test is necessary to vividly depict the safety of reclaimed water for reuse. A toxicity test battery consisting of lethality, genotoxicity and endocrine disrupting effect was designed to screen the multiple biological effects of residual toxic chemicals in reclaimed water. The toxicity results of reclaimed water were converted into the equivalent concentrations of the corresponding positive reference substances (EQC). Simultaneously, the predicted no-effect concentration (PNEC) of each positive reference substance was obtained by analyzing the species sensitivity distribution (SSD) of toxicity data. An index “toxicity score” was proposed and valued as 1, 2, 3, or 4 depending on the ratio of the corresponding EQC to PNEC. For vividly ranking the safety of reclaimed water, an integrated assessment index “toxicity rank” was proposed, which was classified into A, B, C, or D rank with A being the safest. The proposed method was proved to be effective in evaluating reclaimed water samples in case studies.
    Journal of Environmental Sciences 10/2014; · 1.77 Impact Factor
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    ABSTRACT: The stereoselective synthesis of the title compound (I) from L-arabinose is reported.
    ChemInform 09/2014; 45(35).
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    ABSTRACT: A novel and efficient method for one-pot synthesis of 2,4-disubstituted thiazoles from carboxylic acids or anhydrides is established. Based on this new methodology, the total synthesis of bis-2,4-disubstituted bis(thiazoles) natural product Cystothiazole C is also presented.
    Organic & Biomolecular Chemistry 08/2014; · 3.57 Impact Factor
  • Chaoli Zhang, Jun Liu, Yuguo Du
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    ABSTRACT: The target compound is synthesized in 11 steps with 22% overall yield.
    ChemInform 07/2014; 45(28).
  • Yuan Li, Dongbin Wei, Yuguo Du
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    ABSTRACT: The characteristics of the oxidative transformation of the antibiotic levofloxacin (abbreviated as LEV) by manganese oxide were investigated. Up to 91% of LEV were removed with an equivalent of 200units (abbreviated as equiv) of manganese oxide within a 35-day treatment period. A total of ten transformation products were identified, and five of them were newly reported. A tentative transformation pathway of LEV in the manganese oxide system involving oxidation and dealkylation was proposed. In addition, the variation in the genotoxicity and antibacterial activity along with the treatment by manganese oxide were traced using a SOS/umu assay and Escherichia coli growth inhibition assay, respectively. The results indicated that the genotoxicity significantly decreased in response to treatment with manganese oxide, while the antibacterial activity was not markedly affected until 160-equiv of δ-MnO2 were added. This study suggests that the oxidative degradation of LEV by manganese oxide can play an important role in the natural attenuation of LEV in sediment or soil matrices. The transformation reaction may be further optimized for removing quinolone antibiotics from wastewater or other environmental matrices to reduce the potential risk.
    Chemosphere 07/2014; 119C:282-288. · 3.14 Impact Factor
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    ABSTRACT: 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) and polychlorinated biphenyls (PCBs) are persistent organic pollutants which coexist in environment, and human are co-exposed to these chemicals. Our present study was aimed to investigate the possible enhanced nonalcoholic fatty liver disease (NAFLD) in ApoE−/− mice co-exposed to TCDD and PCBs and to reveal the potential mechanisms involved in. Male ApoE−/− mice were exposed to TCDD (15 μg/kg) and Aroclor1254 (55 mg/kg, a representative mixture of PCBs) alone or in combination by intraperitoneal injection four times over a 6-week period. Those mice co-exposed to PCBs and TCDD developed serious liver steatosis, necrosis, and inflammatory stimuli. Interestingly, all treatment induced hepatic cytochrome P450 1A1 (CYP1A1) expression, but the maximal level of CYP1A1 was not observed in the co-exposure group. Furthermore, microarray analysis by ingenuity pathway analysis software showed that the nuclear factor-erythroid 2-related factor 2 (Nrf2)-mediated oxidative stress response pathway was significantly activated following co-exposure to TCDD and PCBs. Our data demonstrated that co-exposure to TCDD and PCBs markedly worsen NAFLD in ApoE−/− mice. © 2014 Wiley Periodicals, Inc. Environ Toxicol, 2014.
    Environmental Toxicology 05/2014; · 2.71 Impact Factor
  • Tetrahedron 04/2014; 70(16):2616–2620. · 2.80 Impact Factor
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    ABSTRACT: Penarolide sulfate A2, a 31-membered macrolide encompassing a proline residue and three sulfate groups, was firstly synthesized in 16 linear steps with 4.8% overall yield. Three consecutive stereogenic centers in penarolide sulfate A2 were efficiently derived from natural chiral template l-arabinose. The crucial assembly reactions included Brown asymmetric allylation, olefin cross-metathesis, alkyne-epoxide coupling, and macrolactamization. The anti-yeast α-glucosidase activities of penarolide sulfate A2 and its fully desulfated derivative were examined showing IC50 values of 4.87 and 10.74 μg mL(-1), respectively.
    Organic & Biomolecular Chemistry 02/2014; · 3.57 Impact Factor
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    ABSTRACT: Benzophenones (BPs) are a class of widely used UV filters, which have been frequently detected within multiple environmental matrices. Disinfection is a necessary process in water treatment processes. The transformation behaviors and toxicity changes of 14 BP-type UV filters during chlorination disinfection treatment were investigated in this study. A new index, the acute toxicity formation potential, was proposed to evaluate the toxicity changes and potential risks of BP-type UV filters during chlorination treatment. It was found that 13 of 14 BP-type UV filters exhibited toxicity decreases in the chlorination disinfection process, more or less, while one showed a toxicity increase. The toxicity changes were dependent on substitution effects, such that 2,4-di-hydroxylated or 3-hydroxylated BPs exhibited significant toxicity decreases after chlorination treatment due to the ready cleavage of the aromatic ring. Importantly, the acute toxicity changes could be duplicated in an ambient water matrix.
    Journal of Environmental Sciences 02/2014; 26(2):440–447. · 1.77 Impact Factor
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    ABSTRACT: Divergent syntheses of two 14-membered resorcylic acid lactones (RALs), cochliomycin B (6) and zeaenol (22), have been accomplished. The key feature in our strategy was the facile construction of three contiguous stereogenic centers in the title molecules by using natural L-arabinose as the chiral template. The key reactions included Takai olefination, Suzuki cross coupling, transesterification, and a late-stage ring-closing metathesis (RCM).
    Annalen der Chemie und Pharmacie 01/2014; · 3.10 Impact Factor
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    ABSTRACT: 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and polychlorinated biphenyls (PCBs) are persistent organic pollutants found as complex mixtures in the environment throughout the world. Therefore, humans are ubiquitously and simultaneously exposed to TCDD and PCBs. TCDD and PCBs alone have been linked to atherosclerosis. However, the effects of interactions or synergism between TCDD and PCBs on atherogenesis are unknown. We investigated the possible enhanced atherogenesis by co-exposure to TCDD and PCBs and the potential mechanism(s) involved in this enhancement. Male apoE −/− mice were exposed to TCDD (15 μg/kg) and Aroclor1254 (55 mg/kg, a representative mixture of PCBs) alone or in combination by intraperitoneal injection four times over six weeks of duration. Our results showed that mice exposed to TCDD alone, but not Aroclor1254 alone, developed atherosclerotic lesions. Moreover, we found that atherosclerotic disease was exacerbated to the greatest extent in mice co-exposed to TCDD and Aroclor1254. The enhanced lesions correlated with several pro-atherogenic changes, including a marked increase in the accumulation of the platelet-derived chemokine PF4, and the expression of the proinflammatory cytokine MCP-1 and the critical immunity gene-RIG-I. Our data demonstrated that co-exposure to TCDD and Aroclor1254 markedly enhanced atherogenesis in apoE −/− mice. Significantly, our observations suggest that combined exposure to TCDD and PCBs may be a greater cardiovascular health risk than previously anticipated from individual studies.
    Toxicology and Applied Pharmacology 01/2014; · 3.98 Impact Factor
  • Min Li, Dongbin Wei, Yuguo Du
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    ABSTRACT: Acute toxicity of 21 quinolone antibiotics was monitored using photobacterium Vibrio fischeri assay. The minimum IC20 (inhibitory concentration for 20% luminescence elimination) was obtained at the least 18.86 μmol/L for the tested quinolones. A quantitative structure–activity relationship model was established to investigate the possible mechanism for the acute toxicity. The critical physicochemical descriptors, describing σ and π atom electronegativity, implied that the electron transfer might occur between the quinolones and photobacterium V. fischeri. Although the quinolones exhibited limited acute toxicity to photobacterium, toxicity elevation was detected after their chlorination. Hence, chlorination disinfection treatment of quinolone-containing water should be of concerns.
    Journal of Environmental Sciences. 01/2014;
  • Chaoli Zhang, Jun Liu, Yuguo Du
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    ABSTRACT: The first total synthesis of natural product ribisin A has been achieved in 11 steps from commercially available methyl α-d-glucopyranoside with 21.6% overall yield. The highly oxygenated benzofuran skeleton of this natural product was constructed, taking advantages of the inherent chirality of d-glucose, through the key reactions of Ferrier carbocyclization, Johnson iodination, Suzuki cross-coupling, and Wacker oxidative cyclization.
    Tetrahedron Letters 01/2014; 55(4):959–961. · 2.40 Impact Factor
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    ABSTRACT: The genotoxicity of 21 quinolones antibiotics was determined using SOS/umu assay. Some quinolones exhibited high genotoxicity, and the chemical substituent on quinolone ring significantly affected genotoxicity. To establish the relationship between genotoxicity and substituent, a 2D-QSAR model based on quantum chemical parameters was developed. Calculation suggested that both steric and electrostatic properties were correlated well with genotoxicity. Furthermore, the specific effect on three key active sites (1-, 7- and 8-positions) of quinolone ring was investigated using a 3D-QSAR (comparative molecular field analysis, CoMFA) method. From our modeling, the genotoxicity increased when substituents had: (1) big volume and/or positive charge at 1-position; (2) negative charge at 7-position; and (3) small volume and/or negative charge at 8-position. The developed QSAR models were applicable to estimate genotoxicity of quinolones antibiotics and their transformation products. It is noted that some of the transformation products exhibited higher genotoxicity comparing to their precursor (e.g., ciprofloxacin). This study provided an alternative way to understand the molecule genotoxicity of quinolones derivatives, as well as to evaluate their potential environmental risks.
    Chemosphere 09/2013; · 3.14 Impact Factor
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    ABSTRACT: Large quantities of cephalosporins have entered into aquatic environment in recent years, posing potential adverse effect to human health and ecological safety. In this study, cefazolin, one of widely used cephalosporins, was targeted to explore its transformation behaviors in chlorination disinfection process. With the help of ultra high performance liquid chromatography and high resolution mass spectroscopy, one chlorinated product and four oxidation products were detected in cefazolin chlorination system. The corresponding transformation pathways of cefazolin were proposed. Two kinds of reactions occurred in chlorination system, one was oxidation of thioether-sulfur to sulfoxide and di-sulfoxide, and the other was base-catalyzed electrophilic substitution of alpha-H of amide by chlorine atom. The pH value determined the occurrence of reaction types, and increasing chlorine dose promoted transformation of cefazolin. More importantly, genotoxicity in SOS/umu assay had an elevation after chlorination, which might be attributed to the formation of chlorinated product and sulfoxide during chlorination process.
    Journal of hazardous materials 08/2013; 262C:48-54. · 4.33 Impact Factor
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    ABSTRACT: The UV-filter BP-4 (2-hydroxy-4-methoxybenzophenone-5-sulfonic acid) has been frequently observed in the environment, showing high potentials to invade drinking water, swimming water, or wastewater reclamation treatment systems. With the help of high performance liquid chromatography-high resolution mass spectrometry and nuclear magnetic resonance spectroscopy, 10 new products from free chlorine-promoted BP-4 disinfection have been disclosed and their possible transformation routes have been investigated. The first route is chlorine substitution of BP-4 and its transformation products, forming mono-, di-, and tri-chlorinated BP-4 analogs. The second is Baeyer-Villiger-Type oxidation, converting diphenyl ketone to phenyl ester derivatives. The third is ester hydrolysis, generating corresponding phenolic and benzoic products. The fourth is decarboxylation, replacing the carboxyl group by chloride in the benzoic-type intermediate. The fifth is desulfonation, degrading the sulfonic group through an alternative chlorine substitution on the benzene ring. Orthogonal experiments have been established to investigate the species transformed from BP-4 at different pH values and free available chlorine (FAC) dosages. The reaction pathways are strongly dependent on pH conditions, while an excessive amount of FAC eliminates BP-4 to the smaller molecules. The initial transformation of BP-4 in chlorination system follows pseudo-first-order kinetics, and its half-lives ranged from 7.48 s to 1.26 × 10(2) s. More importantly, we have observed that the FAC-treated BP-4 aqueous solution might increase the genotoxic potentials due to the generation of chlorinated disinfection by-products.
    Water Research 08/2013; · 4.66 Impact Factor
  • Xing Zhang, Jun Liu, Yi Liu, Yuguo Du
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    ABSTRACT: An efficient synthesis toward 2-alkyl substituted oxazoles has been achieved through Suzuki cross-coupling reaction. Treatment of various alkyl iodides with 9-MeO-BBN, followed by in situ palladium-catalyzed carbon–carbon formation with 2-iodooxazoles obtained the 2-alkyl substituted oxazoles in good to excellent yields. Regioselective C2-alkylation on 2,4-di-iodooxazole under the same reaction conditions was firstly disclosed.
    Tetrahedron Letters 07/2013; 54(31):4045–4048. · 2.40 Impact Factor
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    ABSTRACT: Microcystins (MCs) are a family of cyclic heptapeptides that are produced by blooming algae Microcystis. MCs have been implicated in the development of liver cancer, necrosis and even intrahepatic bleeding. Effective prophylactic approaches and complete removal of MCs are urgently needed. Accumulating evidence suggests that microcystin-LR (MC-LR)-induced damage is accompanied by oxidative stress. Supplementation of Se can enhance resistance to oxidative stress. Therefore, in the present study, we investigated the protective effects of κ-Selenocarrageenan (Se-Car), a kind of organic Se compound, in Balb/c mice exposed to MC-LR. Our results proved that Se-Car could significantly ameliorate the hepatic damage induced by MC-LR, including serum markers of liver dysfunction, oxidative damages and histological alterations. Furthermore, Se-Car could significantly alleviate the up-regulation of the molecular targets indicating mitochondrial dysfunction and endoplasmic reticulum stress induced by MC-LR. In conclusion, Se-Car showed clear protection against toxicity induced by MC-LR. Thus, Se-Car could be useful as a new category of anti-MC-LR toxicity reagent.
    Food and chemical toxicology: an international journal published for the British Industrial Biological Research Association 06/2013; · 2.99 Impact Factor
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    ABSTRACT: Benzophenones (BPs) are widely used in UV filters, fragrance enhancers, and plastic additives. In this study, the genotoxicity of 14 BPs was tested using the SOS/umu assay, and the related substituent contribution was disclosed. The results of this study revealed that the major contributor to the genotoxicity of the BPs was the ortho,para-di-substitution, and the increasing hydroxy substitution on the benzene ring. In addition, the higher the dispersion of the substituent species on the two benzene rings, the lower the genotoxicity exhibited by the compound. Furthermore, 2 dimensional and 3 dimenional quantitative structure-activity relationships (2D- and 3D-QSAR) studies indicated that hydrogen-bond interactions and electrostatic effects were determinants for the genotoxicity of the BPs. The current results provide useful information for the assessment of the potential ecological risk and health effects of BP-type UV filters.
    Ecotoxicology and Environmental Safety 06/2013; · 2.20 Impact Factor

Publication Stats

349 Citations
245.40 Total Impact Points

Institutions

  • 2001–2014
    • Chinese Academy of Sciences
      • • State Key Laboratory of Environmental Chemistry and Ecotoxicology
      • • Research Center for Eco-Environmental Sciences
      Peping, Beijing, China
    • Academia Sinica
      T’ai-pei, Taipei, Taiwan
  • 2013
    • Wuyi University
      Peping, Beijing, China
  • 2001–2013
    • Northeast Institute of Geography and Agroecology
      • • State Key Laboratory of Environmental Chemistry and Ecotoxicology
      • • Research Center for Eco-Environmental Sciences
      • • Dalian Institute of Chemical Physics
      Beijing, Beijing Shi, China
  • 2010–2012
    • Technical Institute of Physics and Chemistry
      Peping, Beijing, China
    • University of Iowa
      • Department of Chemistry
      Iowa City, Iowa, United States
  • 2011
    • Shandong University
      Chi-nan-shih, Shandong Sheng, China
  • 2009
    • Chinese Research Academy of Environmental Sciences
      Peping, Beijing, China
    • Albany Medical College
      • Center for Immunology and Microbial Disease
      Albany, New York, United States
  • 2005
    • Yunnan University
      Yün-nan, Yunnan, China