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

Publications

publié le , mis à jour le

2023



  • E. Liu, S. Cherraben, L. Boulo, C. Troufflard, B. Hasenknopf, G. Vives, et M. Sollogoub, « A molecular information ratchet using a cone-shaped macrocycle », Chem, p. S245192942200660X, 2023.


  • H. Madec, F. Figueiredo, K. Cariou, S. Roland, M. Sollogoub, et G. Gasser, « Metal complexes for catalytic and photocatalytic reactions in living cells and organisms », Chemical Science, vol. 14, nᵒ 3, p. 409-442, 2023.
    Résumé : This review presents discrete metal complexes that catalyse or photocatalyse reactions within living cells or living organisms. , The development of organometallic catalysis has greatly expanded the synthetic chemist toolbox compared to only exploiting “classical” organic chemistry. Although more widely used in organic solvents, metal-based catalysts have also emerged as efficient tools for developing organic transformations in water, thus paving the way for further development of bio-compatible reactions. However, performing metal-catalysed reactions within living cells or organisms induces additional constraints to the design of reactions and catalysts. In particular, metal complexes must exhibit good efficiency in complex aqueous media at low concentrations, good cell specificity, good cellular uptake and low toxicity. In this review, we focus on the presentation of discrete metal complexes that catalyse or photocatalyse reactions within living cells or living organisms. We describe the different reaction designs that have proved to be successful under these conditions, which involve very few metals (Ir, Pd, Ru, Pt, Cu, Au, and Fe) and range from in cellulo deprotection/decaging/activation of fluorophores, drugs, proteins and DNA to in cellulo synthesis of active molecules, and protein and organelle labelling. We also present developments in bio-compatible photo-activatable catalysts, which represent a very recent emerging area of research and some prospects in the field.
    Mots-clés : GOBS, POLE 3.
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  • A. Mascherpa, N. Ishii, A. Tayagui, J. Liu, M. Sollogoub, et A. J. Fairbanks, « Lysosomal Targeting of β‐Cyclodextrin », Chemistry – A European Journal, vol. 29, nᵒ 4, p. e202203252, janv. 2023.

2022



  • X. Bai, A. Ali, N. Wang, Z. Liu, Z. Lv, Z. Zhang, X. Zhao, H. Hao, Y. Zhang, et F. - U. Rahman, « Inhibition of SREBP-mediated lipid biosynthesis and activation of multiple anticancer mechanisms by platinum complexes: Ascribe possibilities of new antitumor strategies », European Journal of Medicinal Chemistry, vol. 227, p. 113920, 2022.


  • Y. Chen, X. Wang, X. Ma, S. Liang, Q. Gao, E. V. Tretyakova, Y. Zhang, D. Zhou, et S. Xiao, « Facial Synthesis and Bioevaluation of Well-Defined OEGylated Betulinic Acid-Cyclodextrin Conjugates for Inhibition of Influenza Infection », Molecules, vol. 27, nᵒ 4, p. 1163, févr. 2022.
    Résumé : Betulinic acid (BA) and its derivatives exhibit a variety of biological activities, especially their anti-HIV-1 activity, but generally have only modest inhibitory potency against influenza virus. The entry of influenza virus into host cells can be competitively inhibited by multivalent derivatives targeting hemagglutinin. In this study, a series of hexa-, hepta- and octavalent BA derivatives based on α-, β- and γ-cyclodextrin scaffolds, respectively, with varying lengths of flexible oligo(ethylene glycol) linkers was designed and synthesized using a microwave-assisted copper-catalyzed 1,3-dipolar cycloaddition reaction. The generated BA-cyclodextrin conjugates were tested for their in vitro activity against influenza A/WSN/33 (H1N1) virus and cytotoxicity. Among the tested compounds, 58, 80 and 82 showed slight cytotoxicity to Madin-Darby canine kidney cells with viabilities ranging from 64 to 68% at a high concentration of 100 μM. Four conjugates 51 and 69–71 showed significant inhibitory effects on influenza infection with half maximal inhibitory concentration values of 5.20, 9.82, 7.48 and 7.59 μM, respectively. The structure-activity relationships of multivalent BA-cyclodextrin conjugates were discussed, highlighting that multivalent BA derivatives may be potential antiviral agents against influenza infection.
    Mots-clés : GOBS, POLE 3.
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  • P. Dong, S. Cheng, Y. Wang, H. Gao, Y. Zhang, T. Zhu, P. Yu, et X. Meng, « A self-adjuvanting anti-tumor nanoliposomal vaccine based on fluorine-substituted MUC1 glycopeptide », Chemical Communications, vol. 58, nᵒ 62, p. 8642-8645, 2022.
    Résumé : Both the tumor-associated antigen and the mode of its presentation affect the immune response for antitumor vaccines. , Herein, a self-adjuvanting fluorinated MUC1-based nanoliposomal antitumor vaccine was constructed for the first time. Both the tumor-associated antigen and the mode of its presentation affect the immune response for antitumor vaccines.
    Mots-clés : GOBS, POLE 3.
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  • X. Li, T. Guo, Q. Feng, T. Bai, L. Wu, Y. Liu, X. Zheng, J. Jia, J. Pei, S. Wu, Y. Song, et Y. Zhang, « Progress of thrombus formation and research on the structure-activity relationship for antithrombotic drugs », European Journal of Medicinal Chemistry, vol. 228, p. 114035, 2022.


  • S. Liang, X. Ma, M. Li, Y. Yi, Q. Gao, Y. Zhang, L. Zhang, D. Zhou, et S. Xiao, « Novel β-Cyclodextrin-Based Heptavalent Glycyrrhetinic Acid Conjugates: Synthesis, Characterization, and Anti-Influenza Activity », Frontiers in Chemistry, vol. 10, p. 836955, avr. 2022.
    Résumé : In our continuing efforts toward the design of novel pentacyclic triterpene derivatives as potential anti-influenza virus entry inhibitors, a series of homogeneous heptavalent glycyrrhetinic acid derivatives based on β -cyclodextrin scaffold were designed and synthesized by click chemistry. The structure was unambiguously characterized by NMR, IR, and MALDI-TOF-MS measurements. Seven conjugates showed sufficient inhibitory activity against influenza virus infection based on the cytopathic effect reduction assay with IC 50 values in the micromolar range. The interactions of conjugate 37 , the most potent compound (IC 50 = 2.86 μ M, CC 50 > 100  μ M), with the influenza virus were investigated using the hemagglutination inhibition assay. Moreover, the surface plasmon resonance assay further confirmed that compound 37 bound to the influenza HA protein specifically with a dissociation constant of 5.15 × 10 −7  M. Our results suggest the promising role of β -cyclodextrin as a scaffold for preparing a variety of multivalent compounds as influenza entry inhibitors.
    Mots-clés : GOBS, POLE 3.
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  • Y. Liu, J. Huang, M. Wu, B. Liu, Q. Lin, J. Wu, Y. Ouyang, X. Guo, R. Huang, Y. Zhang, et J. Xu, « Design, synthesis of novel triptolide-glucose conjugates targeting glucose Transporter-1 and their selective antitumor effect », European Journal of Medicinal Chemistry, vol. 238, p. 114463, 2022.


  • J. Meijide Suárez, O. Bistri‐Aslanoff, S. Roland, et M. Sollogoub, « Cavity‐Controlled Coordination of Square Planar Metal Complexes and Substrate Selectivity by NHC‐Capped Cyclodextrins (ICyDs) », ChemCatChem, vol. 14, nᵒ 1, janv. 2022.


  • J. Ming, M. Z. Bhatti, A. Ali, Z. Zhang, N. Wang, A. Mohyuddin, J. Chen, Y. Zhang, et F. - U. Rahman, « Vitamin B6 based Pt(II) complexes: biomolecule derived potential cytotoxic agents for thyroid cancer », Metallomics, vol. 14, nᵒ 8, p. mfac053, août 2022.
    Résumé : Abstract Vitamin B6 is an essential vitamin that serves as a co-enzyme in a number of enzymatic reactions in metabolism of lipids, amino acids, and glucose. In the current study, we synthesized vitamin B6 derived ligand (L) and its complex Pt(L)Cl (C1). The ancillary chloride ligand of C1 was exchanged with pyridine co-ligand and another complex Pt(L)(py).BF4 (C2) was obtained. Both these complexes were obtained in excellent isolated yields and characterized thoroughly by different analytical methods. Thyroid cancer is one of the most common malignancies of the endocrine system, we studied the in vitro anticancer activity and mechanism of these vitamin B6 derived L and Pt(II) complexes in thyroid cancer cell line (FTC). Based on MTT assay, cell proliferation rate was reduced in a dose-dependent manner. According to apoptosis analysis, vitamin B6 based Pt(II) complexes treated cells depicted necrotic effect and TUNEL based apoptosis was observed in cancer cells. Furthermore, qRT-PCR analyses of cancer cells treated with C1 and/or C2 showed regulated expression of anti-apoptotic, pro-apoptosis and autophagy related genes. Western blot results demonstrated that C1 and C2 induced the activation of p53 and the cleavage of Poly (ADP-ribose) polymerase (PARP). These results suggest that these complexes inhibit the growth of FTC cells and induce apoptosis through p53 signaling. Thus, vitamin B6 derived Pt(II) complexes C1 and C2 may be potential cytotoxic agents for the treatment of thyroid cancer.
    Mots-clés : GOBS, POLE 3.
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  • X. Qiao, B. Wang, Z. Yuan, F. Yu, Y. Zhang, Y. Wang, Y. Yang, J. Tang, Z. Jiang, L. Lin, L. Zhang, Z. Du, et Y. Zhang, « The polysaccharides from Yiqi Yangyin complex attenuated mammary gland hyperplasia: Integrating underlying biological mechanisms and network pharmacology », Journal of Functional Foods, vol. 88, p. 104878, 2022.


  • J. Scelle, H. Vervoitte, L. Bouteiller, L. - M. Chamoreau, M. Sollogoub, G. Vives, et B. Hasenknopf, « Size-dependent compression of threaded alkyldiphosphate in head to head cyclodextrin [3]pseudorotaxanes », Chemical Science, vol. 13, nᵒ 8, p. 2218-2225, févr. 2022.
    Résumé : The encapsulation of guests in a confined space enables unusual conformations and reactivities. In particular, the compression of akyl chains has been obtained by self-assembled molecular capsules but such an effect has not been reported in solution for pseudorotaxane architectures. By exploiting the tendency of cyclodextrin (CD) to form head to head [3]pseudorotaxanes and the hydrogen bonding abilities of phosphate groups, we have studied the effect of the CD dimer cavity on the conformation of threaded α,ω-alkyl-diphosphate axles. The formation of [2]pseudorotaxanes and [3]pseudorotaxanes was investigated by a combination of NMR, ITC and X-ray diffraction techniques. In the solid state, the [3]pseudorotaxane with a C8 axle presents a fully extended conformation with both terminal phosphate groups interacting with hydroxyl groups of the primary rim of CDs. Such hydrogen bonding interactions are also present with the C9 and C10 axles resulting in a compression of the alkyl chain with gauche conformations in the solid state. NMR studies have shown that this effect is maintained in solution resulting in a size-dependent progressive compression of the alkyl chain by the CD [3]pseudorotaxane architecture for C9, C10 and C11 axles.
    Mots-clés : GOBS, POLYMERES.
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  • K. Sheng, Y. Song, F. Lei, W. Zhao, L. Fan, L. Wu, Y. Liu, S. Wu, et Y. Zhang, « Research progress in pharmacological activities and structure-activity relationships of tetralone scaffolds as pharmacophore and fluorescent skeleton », European Journal of Medicinal Chemistry, vol. 227, p. 113964, 2022.


  • L. Tanzi, D. Rubes, T. Bavaro, M. Sollogoub, M. Serra, Y. Zhang, et M. Terreni, « Controlled Decoration of [60]Fullerene with Polymannan Analogues and Amino Acid Derivatives through Malondiamide-Based Linkers », Molecules, vol. 27, nᵒ 9, p. 2776, avr. 2022.
    Résumé : In the last few years, nanomaterials based on fullerene have begun to be considered promising tools in the development of efficient adjuvant/delivery systems for vaccination, thanks to their several advantages such as biocompatibility, size, and easy preparation and modification. In this work we reported the chemoenzymatic synthesis of natural polymannan analogues (di- and tri-mannan oligosaccharides characterized by α1,6man and/or α1,2man motifs) endowed with an anomeric propargyl group. These sugar derivatives were submitted to 1,3 Huisgen dipolar cycloaddition with a malondiamide-based chain equipped with two azido terminal groups. The obtained sugar-modified malondiamide derivatives were used to functionalize the surface of Buckminster fullerene (C60) in a highly controlled fashion, and yields (11–41%) higher than those so far reported by employing analogue linkers. The same strategy has been exploited to obtain C60 endowed with natural and unnatural amino acid derivatives. Finally, the first double functionalization of fullerene with both sugar- and amino acid-modified malondiamide chains was successfully performed, paving the way to the possible derivatization of fullerenes with immunogenic sugars and more complex antigenic peptides.
    Mots-clés : GOBS, POLE 3.
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  • L. Tanzi, M. Terreni, et Y. Zhang, « Synthesis and biological application of glyco- and peptide derivatives of fullerene C60 », European Journal of Medicinal Chemistry, vol. 230, p. 114104, 2022.


  • S. Roland et M. Sollogoub, « <i>N</i> ‐heterocyclic Carbene ( <span style="font-variant:small-caps;">NHC</span> )‐Capped Cyclodextrins for Cavity‐Controlled Catalysis », in Supramolecular Catalysis, 1ᵉʳ éd., P. W. N. M. van Leeuwen et M. Raynal, Éd. Wiley, 2022, p. 287-301.


  • Y. Yi, X. Ma, R. Liu, X. Chu, H. Li, J. Zhang, Q. Gao, Y. Zhang, L. Zhang, D. Zhou, et S. Xiao, « An attempt to synthesize the two monomers of CDTOH: Unexpected NMR and X-ray diffraction crystal analysis », Tetrahedron Letters, vol. 91, p. 153638, 2022.

2021

2020

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.
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