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  • T. Auvray, M. - P. Santoni, B. Hasenknopf, et G. S. Hanan, « Covalent hybrids based on Re(I) tricarbonyl complexes and polypyridine-functionalized polyoxometalate: synthesis, characterization and electronic properties », Dalton Transactions, vol. 46, nᵒ 30, p. 10029-10036, 2017.

  • M. W. Cooke, M. - P. Santoni, F. Loiseau, B. Hasenknopf, et G. S. Hanan, « Energy transfer in rhodium–ruthenium dimer-of-dimer assemblies », Inorganica Chimica Acta, vol. 454, p. 208-215, 2017.

  • B. Doistau, L. Benda, J. - L. Cantin, L. - M. Chamoreau, E. Ruiz, V. Marvaud, B. Hasenknopf, et G. Vives, « Six states switching of redox-active molecular tweezers by three orthogonal stimuli », Journal of the American Chemical Society, juin 2017.
    Résumé : A six level molecular switch based on terpyridine(Ni-salphen)2 tweezers and addressable by three orthogonal stimuli (metal coordination, redox reaction and guest binding) is reported. By a metal coordination stimulus, the tweezers can be mechanically switched from an open “W”-shaped conformation to a closed “U”-shaped form. Theses two states can each be reversibly oxidized by the redox stimulus and bind to a pyrazine guest resulting in four additional states. All six states are stable and accessible by the right combination of stimuli and were studied by NMR, XRD, EPR spectroscopy and DFT calculations. The combination of the supramolecular concepts of mechanical motion and guest binding with the redox non-innocent and valence tautomerism properties of Ni-salphen complexes added two new dimensions to a mechanical switch.
    Mots-clés : E-POM, GOBS, POLE 2, POLE 3.

  • J. W. Fredy, J. Scelle, G. Ramniceanu, B. - T. Doan, C. S. Bonnet, É. Tóth, M. Ménand, M. Sollogoub, G. Vives, et B. Hasenknopf, « Mechanostereoselective One-Pot Synthesis of Functionalized Head-to-Head Cyclodextrin [3]Rotaxanes and T

    heir Application as Magnetic Resonance Imaging Contrast Agents », Organic Letters, vol. 19, nᵒ 5, p. 1136-1139, mars 2017.
    Mots-clés : GOBS, POLE 3.
    Note Note
    <p>doi: 10.1021/acs.orglett.7b00153</p>

  • X. Han, L. - L. Si, Y. - Y. Shi, Z. - B. Fan, S. - X. Wang, Z. - Y. Tian, M. Li, J. - Q. Sun, P. - X. Jiao, F. - X. Ran, Y. - M. Zhang, D. - M. Zhou, et S. - L. Xiao, « Synthesis and In Vitro Anti-Influenza Virus Evaluation of Novel Sialic Acid (C-5 and C-9)-Pentacyclic Triterpene Derivatives », Molecules, vol. 22, nᵒ 7, p. 1018, juin 2017.

  • F. Liu, Z. - Y. Zhu, X. Sun, H. Gao, et Y. - M. Zhang, « The preparation of three selenium-containing Cordyceps militaris polysaccharides: Characterization and anti-tumor activities », International Journal of Biological Macromolecules, vol. 99, p. 196-204, 2017.

  • J. Malinge, B. Géraudie, P. Savel, V. Nataf, A. Prignon, C. Provost, Y. Zhang, P. Ou, K. Kerrou, J. - N. Talbot, J. - M. Siaugue, M. Sollogoub, et C. Ménager, « Liposomes for PET and MR Imaging and for Dual Targeting (Magnetic Field/Glucose Moiety): Synthesis, Properties, and in Vivo Studies », Molecular Pharmaceutics, vol. 14, nᵒ 2, p. 406-414, févr. 2017.
    Résumé : We describe the potentiality of a new liposomal formulation enabling positron emission tomography (PET) and magnetic resonance MR imaging. The bimodality is achieved by coupling a 68Ga-based radiotracer on the bilayer of magnetic liposomes. In order to enhance the targeting properties obtained under a permanent magnetic field, a sugar moiety was added in the lipid formulation. Two new phospholipids were synthesized, one with a specific chelator of 68Ga (DSPE-PEG-NODAGA) and one with a glucose moiety (DSPE-PEG-glucose). The liposomes were produced according to a fast and safe process, with a high radiolabeling yield. MR and PET imaging were performed on mice bearing human glioblastoma tumors (U87MG) after iv injection. The accumulation of the liposomes in solid tumor is evidenced by MR imaging and the amount is evaluated in vivo and ex vivo according to PET imaging. An efficient magnetic targeting is achieved with these new magnetic liposomes.
    Mots-clés : GOBS, POLE 3.

  • C. K. O'Sullivan, M. Ortiz, A. , M. Debela, M. Svobodova, S. Thorimbert, D. Lesage, R. Cole, et B. Hasenknopf, « PCR Incorporation of Polyoxometalate Modified Deoxynucleotide Triphosphates and Their Application in Molecular Electrochemical Sensing of Yersinia pestis », Chemistry – A European Journal, vol. 23, nᵒ 44, p. 10597–10603, 2017.
    Résumé : Redox-labeled nucleotides are of increasing interest for the fabrication of next generation molecular tools and should meet requirements of being thermally stable, sensitive, and compatible with polymerase-mediated incorporation whilst also being electrochemically discriminable. The synthesis and characterization of Keggin and Dawson polyoxometalate-deoxynucleotide (POM-dNTP) bioconjugates linked through 7-deaza-modified purines is described. The modified POM-dNTPs were used for polymerase based amplification of a DNA sequence specific for Yersinia pestis and the amplified DNA detected via an electrochemical DNA sensor. This highlights the potential of polyoxometalates as thermally stable, sensitive and polymerase-compatible redox labels for exploitation in bioanalytical applications.
    Mots-clés : Biosensor, CHEMBIO, CSOB, Electroanalytical Chemistry, GOBS, Labelled nucleotides, PCR, POLE 3, Polyoxometalates.

  • G. Pan, X. Li, L. Zhao, M. Wu, C. Su, X. Li, Y. Zhang, P. Yu, Y. Teng, et K. Lu, « Synthesis and anti-oxidant activity evaluation of (±)-Anastatins A, B and their analogs », European Journal of Medicinal Chemistry, vol. 138, p. 577-589, 2017.

  • M. Petricevic, L. F. Sobala, P. Z. Fernandes, L. Raich, A. J. Thompson, G. Bernardo-Seisdedos, O. Millet, S. Zhu, M. Sollogoub, J. Jiménez-Barbero, C. Rovira, G. J. Davies, et S. J. Williams, « Contribution of Shape and Charge to the Inhibition of a Family GH99 endo-α-1,2-Mannanase », Journal of the American Chemical Society, vol. 139, nᵒ 3, p. 1089-1097, janv. 2017.
    Résumé : Inhibitor design incorporating features of the reaction coordinate and transition-state structure has emerged as a powerful approach for the development of enzyme inhibitors. Such inhibitors find use as mechanistic probes, chemical biology tools, and therapeutics. Endo-α-1,2-mannosidases and endo-α-1,2-mannanases, members of glycoside hydrolase family 99 (GH99), are interesting targets for inhibitor development as they play key roles in N-glycan maturation and microbiotal yeast mannan degradation, respectively. These enzymes are proposed to act via a 1,2-anhydrosugar “epoxide” mechanism that proceeds through an unusual conformational itinerary. Here, we explore how shape and charge contribute to binding of diverse inhibitors of these enzymes. We report the synthesis of neutral dideoxy, glucal and cyclohexenyl disaccharide inhibitors, their binding to GH99 endo-α-1,2-mannanases, and their structural analysis by X-ray crystallography. Quantum mechanical calculations of the free energy landscapes reveal how the neutral inhibitors provide shape but not charge mimicry of the proposed intermediate and transition state structures. Building upon the knowledge of shape and charge contributions to inhibition of family GH99 enzymes, we design and synthesize α-Man-1,3-noeuromycin, which is revealed to be the most potent inhibitor (KD 13 nM for Bacteroides xylanisolvens GH99 enzyme) of these enzymes yet reported. This work reveals how shape and charge mimicry of transition state features can enable the rational design of potent inhibitors.
    Mots-clés : GOBS, POLE 3.

  • Y. Shi, L. Si, X. Han, Z. Fan, S. Wang, M. Li, J. Sun, Y. Zhang, D. Zhou, et S. Xiao, « Synthesis of novel pentacyclic triterpene–Neu5Ac2en derivatives and investigation of their in vitro anti-influenza entry activity », MedChemComm, vol. 8, nᵒ 7, p. 1531-1541, 2017.

  • H. Sun, W. Ding, X. Song, D. Wang, M. Chen, K. Wang, Y. Zhang, P. Yuan, Y. Ma, R. Wang, R. H. Dodd, Y. Zhang, K. Lu, et P. Yu, « Synthesis of 6-hydroxyaurone analogues and evaluation of their α-glucosidase inhibitory and glucose consumption-promoting activity: Development of highly active 5,6-disubstituted derivatives », Bioorganic & Medicinal Chemistry Letters, vol. 27, nᵒ 15, p. 3226-3230, 2017.

  • H. - Q. Sun, Z. - Y. Zhu, X. - Y. Yang, M. Meng, L. - C. Dai, et Y. - M. Zhang, « Preliminary characterization and immunostimulatory activity of a novel functional polysaccharide from Astragalus residue fermented by Paecilomyces sinensis », RSC Advances, vol. 7, nᵒ 38, p. 23875-23881, 2017.

  • Y. Teng, X. Li, K. Yang, X. Li, Z. Zhang, L. Wang, Z. Deng, B. Song, Z. Yan, Y. Zhang, K. Lu, et P. Yu, « Synthesis and antioxidant evaluation of desmethylxanthohumol analogs and their dimers », European Journal of Medicinal Chemistry, vol. 125, p. 335-345, janv. 2017.
    Résumé : Four ring-closed analogs of natural prenylated chalcone desmethylxanthohumol (1) and their dimers were synthesized from the commercially available 1-(2,4,6-trihydroxyphenyl)ethan-1-one in five and six linear steps, respectively. The structures of the eight new derivatives were confirmed using1H NMR, 13C NMR and HRMS. The antioxidant activity of the new chalcone derivatives were evaluated in a PC12 cell model of H2O2-induced oxidative damage. The SAR studies suggested that the catechol motif was essential for the antioxidant activity. Moreover, the dimers showed better antioxidant activity than their corresponding monomers did. Among them, compound 14d was the most potent and increased PC12 cell viability from 25% to 85%. Flow cytometric analysis showed that compound 14d, the most potent compound, decreased the apoptotic PC12 cell percentage and significantly reduced the LDH release and 8-OHdG generation but increased the GSH levels in H2O2-treated PC12 cells. Furthermore, compound 14d had a higher FRAP value than that of gallic acid. It also reduced the stable ABTS+ free radical with a lower EC50 than that of gallic acid.
    Mots-clés : Antioxidant, Chalcone, Desmethylxanthohumol, Dimer, GOBS, POLE 3, Synthesis.

  • Z. Tian, K. Meng, Y. Shi, N. Zhang, X. Liu, H. Jin, Y. Zhang, L. Zhang, D. Zhou, et S. Xiao, « Facile preparation of a symmetric hexavalent oleanolic acid/per- O -methylated α -cyclodextrin conjugate with two conformations in solution and unambiguous NMR analysis », Tetrahedron, vol. 73, nᵒ 17, p. 2512-2517, 2017.

  • Z. Tian, L. Si, K. Meng, X. Zhou, Y. Zhang, D. Zhou, et S. Xiao, « Inhibition of influenza virus infection by multivalent pentacyclic triterpene-functionalized per- O -methylated cyclodextrin conjugates », European Journal of Medicinal Chemistry, vol. 134, p. 133-139, 2017.

  • S. Wu, L. Yang, W. Sun, L. Si, S. Xiao, Q. Wang, L. Dechoux, S. Thorimbert, M. Sollogoub, D. Zhou, et Y. Zhang, « Design, synthesis and biological evaluation of gentiopicroside derivatives as potential antiviral inhibitors », European Journal of Medicinal Chemistry, vol. 130, p. 308-319, avr. 2017.
    Résumé : Based on classical drug design theory, a novel series of gentiopicroside derivatives was designed and synthesized. All synthesized compounds were then biologically evaluated for their inhibition of influenza virus and anti-HCV activity in vitro. Some of the gentiopicroside derivatives, such as 11a, 13d and 16 showed interesting anti-influenza virus activity with IC50 at 39.5 μM, 45.2 μM and 44.0 μM, respectively. However, no significant anti-HCV activity was found for all of gentiopicroside derivatives. The preliminary results indicate that modification of the sugar moiety on gentiopicroside was helpful for enhancing the anti-influenza activities. Our works demonstrate the importance of secoiridoid natural products as new leads in the development of potential antiviral inhibitors.
    Mots-clés : antiviral agents, CHEMBIO, Gentiopicroside derivatives, GOBS, Natural product, POLE 3.

  • S. Wu, N. Yaoyao, Y. Zhao, W. Sun, S. Thorimbert, L. Dechoux, M. Sollogoub, et Y. Zhang, « Research Progress of Natural Product Gentiopicroside - a Secoiridoid Compound », Mini-Reviews in Medicinal Chemistry, vol. 17, nᵒ 1, p. 62-77, 2017.
    Résumé : Gentiopicroside is a secoiridoid compound isolated from Gentiana lutea which is called Qin Jiao in Chinese. It is one of the most common herbal medicines used in China. In this article, we review the pharmacological and biological activity (antiviral, anti-inflammatory, analgesia, antihepatotoxic and choleretic), as well as biotransformation of the gentiopicroside. In addition, attempt towards the total synthesis of gentiopicroside is also presented.
    Mots-clés : Biological activity, CHEMBIO, gentiopicroside, GOBS, natural product, POLE 3.

  • Y. Yang, R. Tu, W. Sun, Z. Zhu, et Y. Zhang, « Silver perchlorate in the mobile phase for rapid separation and determination of a pair of positional isomers in Inula racemosa Hook.f. with RP-HPLC », Journal of Chromatography B, vol. 1063, p. 25-30, 2017.

  • Y. Yang, B. Yin, L. Lv, Z. Wang, J. He, Z. Chen, X. Wen, Y. Zhang, W. Sun, Y. Li, et Y. Zhao, « Gastroprotective effect of aucubin against ethanol-induced gastric mucosal injury in mice », Life Sciences, vol. 189, p. 44-51, 2017.

  • N. Yu, Z. - Y. Zhu, Y. Liu, J. - Y. Zhang, et Y. - M. Zhang, « Chromatographic analysis and preparation of l-arabinose from corncob by acid hydrolysis », Industrial Crops and Products, vol. 95, p. 163-169, janv. 2017.
    Résumé : l-arabinose, a kind of rare sugar, which has already become newly developed functional saccharide with many beneficial biomedical and health effects. In this study, we carried out several experiments to analyze the component of hydrolyzed corncob. Components in the hydrolysate were detected by the methods of ultraviolet spectrogram, HPLC, TLC and High-efficient Thin Layer scanning analysis. The hydrolysis temperature, holding time, concentration of oxalic acid and solid-liquid ratio were investigated as objects by single factor experiments. The results showed that the content of saccharides in the hydrolysate of corncob was up to 72.70%. Three kinds of monosaccharide (d-xylose, l-arabinose, d-glucose) were detected by HPLC analysis and the relative amount of the above three saccharides were 32.8%, 31.4% and 35.7%, respectively. The optimum conditions were: temperature 90 °C, holding time 5 h, concentration of oxalic acid 6%, solid-liquid ratio 1:12, and the highest l-arabinose yield was 14.89%.
    Mots-clés : Acid hydrolysis, Corncob, GOBS, l-arabinose, POLE 3, Yield.

  • P. Zhang, J. Meijide Suárez, T. Driant, E. Derat, Y. Zhang, M. Ménand, S. Roland, et M. Sollogoub, « Cyclodextrin Cavity-Induced Mechanistic Switch in Copper-Catalyzed Hydroboration », Angewandte Chemie International Edition, vol. 56, nᵒ 36, p. 10821-10825, août 2017.
    Mots-clés : catalysis, copper, cyclodextrins, GOBS, MACO, POLE 1, POLE 3, regioselectivity, supramolecular chemistry.
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