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Accueil > Les équipes > Glycochimie Organique Biologique et Supramoléculaire (GOBS) > Publications

Publications

publié le , mis à jour le

2018

2017


  • P. a Zhang, C. Tugny, J. Meijide Suárez, M. Guitet, E. Derat, N. Vanthuyne, Y. M. Zhang, O. Bistri, V. Mouries-Mansuy, M. Ménand, S. Roland, L. Fensterbank, et M. Sollogoub, « Artificial chiral metallo-pockets including a single metal serving as both structural probe and catalytic center », Chem, vol. 3, nᵒ 1, p. 174-191, 2017.
    Mots-clés : GOBS, MACO, POLE 1, POLE 3.


  • P. a 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.
    Pièce jointe Full Text PDF 2.4 Mo (source)


  • 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.
    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 Their 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.

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    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.
    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.
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  • 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.
    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.
    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.
    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 : Anti-influenza virus, antiviral agents, CHEMBIO, Gentiopicroside derivatives, GOBS, Natural product, POLE 3, Secoiridoid.


  • 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.


  • X. Zhu, A. Quaranta, R. Bensasson, M. Sollogoub, et Y. Zhang, « Secondary-rim γ-cyclodextrin functionalization to conjugate with C60: improved efficacy as photosensitizer », Chemistry A European Journal, p. n/a-n/a.
    Résumé : DIBAL-H-mediated demethylation provides a novel entry to secondary rim functionalized γ-CD. 2A,3B-dihydroxyl-per-O-methylated-γ-cyclodextrin has been obtained, whose conjugation with C60 allows the access to the most water-soluble C60 conjugate described so far. The water-solubility 0.12 M (550 mg/mL) is 150 times higher than that of native γ-CD/ C60 complex. Its singlet oxygen (¹O₂) quantum yield is 0.39, an increase by one or two orders of magnitude compared to that of α(β)CD-C60 conjugates.
    Mots-clés : gamma-CD * secondary rim * C60 * aggregation * photosensitizer, GOBS, POLE 3.
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2016



  • M. a Ménand, M. Sollogoub, B. Boitrel, et S. Le Gac, « Hexaphyrin–Cyclodextrin Hybrids: A Nest for Switchable Aromaticity, Asymmetric Confinement, and Isomorphic Fluxionality », Angewandte Chemie International Edition, vol. 55, nᵒ 1, p. 297-301.
    Résumé : Conformational control over the highly flexible π-conjugated system of expanded porphyrins is a key step toward the fundamental understanding of aromaticity and for the development of molecular electronics. We have synthesized unprecedented hexaphyrin–cyclodextrin (HCD) capped hybrids in which the hexaphyrin part is constrained in a planar rectangular conformation in either a 26 or a 28 π-electron oxidation state ([26]/[28]HCD). These structures display strong aromaticity and antiaromaticity, respectively, exhibit markedly different chiroptical properties, and are interconvertible upon the addition of DDQ or NaBH(OAc)3, thus affording a rare switchable aromatic–antiaromatic system with a free-base expanded porphyrin. Conformational analysis revealed discrimination of the two coordination sites of the hexaphyrin, one of which was coupled to a confined asymmetric environment, and fluxional behavior consisting of apparent rotation of the hexaphyrin cap through a shape-shifting mechanism.
    Mots-clés : aromaticity, conformation analysis, Cyclodextrins, degenerate equilibria, GOBS, POLE 3, porphyrinoids.
  • V. Calvez, A. G. Marcellin, L. Bouteiller, M. Menand, P. Evenou, A. Gothland, D. Colesnic, J. Rossignol, et M. Sollogoub, « Capped cyclodextrin-hydrophobic moiety conjugate, cyclodextrin supramolecular poly

    mer, and cyclodextrin-siRNA complex and method of synthesis thereof », U.S. Patent PCT/ EP2016/070892.
    Mots-clés : GOBS, POLE 3, POLE 4, POLYMERES.


  • M. W. Cooke, M. - P. Santoni, B. Hasenknopf, et G. S. Hanan, « Heteroleptic ruthenium(II) chromophores based on tunable polytopic 4′-(benzamidinato)-2,2′:6′,2′′-terpyridines », Dalton Transactions, vol. 45, nᵒ 44, p. 17850-17858.
    Résumé : A modulable and simple approach towards heteroleptic ruthenium(II) complexes of amidine-based polypyridine ligands is presented. New complexes 1 and 2 ([(terpyridine)Ru(terpyridine-C6H4-C(NR)(NHR))]2+ with R = propyl and R = phenyl derivatives, respectively) were characterized by NMR spectroscopy in solution and by X-ray diffraction, which confirmed the obtention of the (E) stereoisomer alone. Depending on the bulkiness of the R-substituents introduced on the amidine moiety, rotational isomerism around the C–N bond could be observed at r.t. Spectroscopic and electrochemical studies showed that the nature of the R-substituents introduced on the amidine moiety can significantly influence the redox and ground-state acido-basic properties of the complexes, while maintaining their electronic features. This particular tunability of polytopic 4′-(amidinato)-terpyridines offers an interesting perspective for photoactive units in larger multi-functional arrays.
    Mots-clés : GOBS, POLE 3.


  • A. M. Debela, S. Thorimbert, B. Hasenknopf, C. K. O'Sullivan, et M. Ortiz, « Electrochemical primer extension for the detection of single nucleotide polymorphisms in the cardiomyopathy associated MYH7 gene », Chemical Communications, vol. 52, nᵒ 4, p. 757-759.
    Résumé : We report the labelling of dideoxy nucleotides (ddNTPs) for use in electrochemical array based primer extension for the detection of single nucleotide polymorphisms (SNPs). The results confirm the extension of the immobilised primers for each of the four ddNTPs, representing a significant advance in achieving a cost-effective platform for screening of disease-specific SNPs.
    Mots-clés : CHEMBIO, GOBS, POLE 3.


  • M. Dong, D. Liu, Y. - H. Li, X. - Q. Chen, K. Luo, Y. - M. Zhang, et R. - T. Li, « Naphthoquinones from Onosma paniculatum with Potential Anti-inflammatory Activity », Planta Medica, vol. 83, nᵒ 07, p. 631-635, nov. 2016.


  • L. Duarte, S. Nag, M. Castro, E. Zaborova, M. Ménand, M. Sollogoub, V. Bennevault, J. - F. Feller, et P. Guégan, « Chemical Sensors Based on New Polyamides Biobased on (Z) Octadec-9-Enedioic Acid and β-Cyclodextrin », Macromolecular Chemistry and Physics, vol. 217, nᵒ 14, p. 1620-1628.


  • S. L. Gac, B. Boitrel, M. Sollogoub, et M. Ménand, « Protonated hexaphyrin–cyclodextrin hybrids: molecular recognition tuned by a kinetic-to-thermodynamic topological adaptation », Chemical Communications, vol. 52, nᵒ 60, p. 9347-9350.
    Résumé : Protonation study of [26/28]hexaphyrin-capped cyclodextrins revealed a temperature controlled conformational transition of the cap. The hexaphyrin undergoes a rectangular-to-triangular shape-shifting which strongly modifies the shape of the confined environment featured by the hybrids, and ultimately affects the encapsulation of the counterions. It provides an attractive access to innovative allosteric host–guest systems.
    Mots-clés : GOBS, POLE 3.


  • Y. Gao, Z. Cao, C. Su, Z. Chen, X. He, F. Ding, H. Li, et Y. Zhang, « Chiron Approaches to the Antitumor Natural Product Fuzanin D », Synthesis, vol. 48, nᵒ 24, p. 4471-4476.
    Résumé : Thieme E-Books & E-Journals
    Mots-clés : GOBS, POLE 3.


  • Y. Gao, X. He, F. Ding, et Y. Zhang, « Recent Progress in Chemical Syntheses of Sphingosines and Phytosphingosines », Synthesis, vol. 48, nᵒ 23, p. 4017-4037.
    Résumé : Thieme E-Books & E-Journals
    Mots-clés : GOBS, POLE 3.


  • X. Han, Y. Shi, L. Si, Z. Fan, H. Wang, R. Xu, P. Jiao, K. Meng, Z. Tian, X. Zhou, H. Jin, X. Wu, H. Chen, Y. Zhang, L. Zhang, S. Xiao, et D. Zhou, « Design, synthesis and biological activity evaluation of novel conjugated sialic acid and pentacyclic triterpene derivatives as anti-influenza entry inhibitors », MedChemCom, vol. 7, nᵒ 10, p. 1932-1945.
    Résumé : Influenza virus is a major human pathogen that causes annual epidemics and occasional pandemics. Recently, plant-derived pentacyclic triterpenes have been shown to act as highly potent anti-viral agents by efficiently preventing the attachment of the virion to the host cells. In this report, we conjugated sialic acid with oleanolic acid (OA), a natural product with broad antiviral entry activity, as well as three other analogs echinocystic acid (EA), ursolic acid (UA) and betulinic acid (BA). A total of 24 conjugated sialic acid and pentacyclic triterpene derivatives with different linkers were synthesized and evaluated for antiviral activity against influenza A/WSN/33 (H1N1) virus in MDCK cell culture. The most potent compound had an IC50 of 41.2 μM. Time-of-addition, hemagglutination inhibition (HI), surface plasmon resonance (SPR) and molecular docking assays demonstrated that compound 20a acted as an influenza virus entry inhibitor by preventing the binding of influenza virus hemagglutinin (HA) protein to host cells.
    Mots-clés : GOBS, POLE 3.

  • X. - C. Liu, Z. - Y. Zhu, Y. - L. Tang, M. -fei Wang, Z. Wang, A. - J. Liu, et Y. - M. Zhang, « Structural properties of polysaccharides from cultivated fruit bodies and mycelium of Cordyceps militaris », Carbohydrate Polymers, vol. 142, p. 63-72.
    Résumé : The structural properties of polysaccharides, respectively, obtained from the fermented mycelium and cultivated fruiting bodies of the Cordyceps militaris were investigated and compared in this paper. First, the crude polysaccharides were extracted from the mycelium and the fruiting bodies, respectively. The polysaccharides were successively purified by Sevag and chromatography on Sephadex G-100 column to produce two polysaccharides fractions termed CMPS-II and CBPS-II, respectively. The average molecular weights of CMPS-II and CBPS-II were 1.402×10(3) kDa and 1.273×10(3) kDa, respectively, and they were mainly composed of mannose, glucose and galactose in the mole ratios of 1:28.63:1.41 and 1:12.41:0.74, respectively, for CMPS-II and CBPS-II. Afterward, the structural features of CMPS-II and CBPS-II were investigated by a combination of chemical and instrumental analysis, such as FT-IR, periodate oxidation-Smith degradation, GC-MS, NMR and methylation analysis. The results indicated that structurally, both CMPS-II and CBPS-II were 1,3-branched-galactomannoglucan that had a linear backbone of (1→4)-linked α-D-glucopyranose (Glcp). Congo-red test revealed that CMPS-II and CBPS-II existed as triple-helical chains in 0.05-0.15 M NaOH solution.
    Mots-clés : Cordyceps militaris, GOBS, POLE 3, Polysaccharide, structure.


  • Z. Liu, Q. Zheng, W. Chen, S. Man, Y. Teng, X. Meng, Y. Zhang, P. Yu, et W. Gao, « Paris saponin I inhibits proliferation and promotes apoptosis through down-regulating AKT activity in human non-small-cell lung cancer cells and inhibiting ERK expression in human small-cell lung cancer cells », RCS Advances, vol. 6, nᵒ 75, p. 70816-70824.
    Résumé : Paris Saponin I (PSI), a steroidal saponin derivative extracted from a traditional Chinese herbal Paris polyphylla, has shown cytotoxic effects on several tumor cell lines. However, the mechanisms of its antitumor activity especially for lung cancers remain to be elucidated. In this present investigation, we continue to explore the efficacy and mechanisms underlying the cytotoxic effects of PSI in lung cancer cell lines. Three non-small cell lung cancer (NSCLC) cells (H1299, H520, H460) and one small cell lung cancer (SCLC) cell (H446) were treated with PSI for the first time. PSI significantly induced cell cycle arrest at the G2/M phase and mitochondrial-related apoptosis NSCLC cells but not SCLC cells. Additionally, PSI reduced phosphorylation of AKT in NSCLC and ERK in SCLC in general. Interestingly, we observed that PSI influenced different signaling pathways among the four kinds of lung cancer cells. After PSI treatment, p38 MAPK and ERK activation were observed in H1299, while p38 MAPK increased and JNK decreased in H520. On the contrary, we found JNK activation in H460 cells with PSI. However, PSI upregulated the AKT activity and inhibited the JNK expression in H446 cells. The results indicate that PSI exhibits the cytotoxicity in different pathways depending on the cancer types.
    Mots-clés : GOBS, POLE 3.


  • A. Martin, A. Arda, J. Désiré, A. Martin-Mingot, N. Probst, P. Sinaÿ, J. Jiménez-Barbero, S. Thibaudeau, et Y. Blériot, « Catching elusive glycosyl cations in a condensed phase with HF/SbF5 superacid », Nature Chemistry, vol. 8, nᵒ 2, p. 186-191.
    Résumé : Glycosyl cations are universally accepted key ionic intermediates in the mechanism of glycosylation, the reaction that covalently links carbohydrates to other molecules. These ions have remained hypothetical species so far because of their extremely short life in organic media as a consequence of their very high reactivity. Here, we report the use of liquid hydrofluoric acid–antimony pentafluoride (HF/SbF5) superacid to generate and stabilize the glycosyl cations derived from peracetylated 2-deoxy and 2-bromoglucopyranose in a condensed phase. Their persistence in this superacid medium allows their three-dimensional structure to be studied by NMR, aided by complementary computations. Their deuteration further confirms the impact of the structure of the glycosyl cation on the stereochemical outcome of its trapping.
    Mots-clés : Carbohydrate chemistry, GOBS, POLE 3, Structure elucidation.

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