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2017



  • D. Gatineau, A. Memboeuf, A. Milet, R. B. Cole, H. Dossmann, Y. Gimbert, et D. Lesage, « Experimental bond dissociation energies of benzylpyridinium thermometer ions determined by threshold-CID and RRKM modeling », International Journal of Mass Spectrometry, vol. 417, p. 69-75, 2017.


  • Y. Gimbert, D. Lesage, C. Fressigné, et J. Maddaluno, « Lithium Amide Protected against Hydrolysis by Aggregated Lithium Halides: An MS + DFT Investigation », The Journal of Organic Chemistry, vol. 82, nᵒ 15, p. 8141-8147, août 2017.


  • M. Gormen, P. Pigeon, Y. Wang, A. Vessières, S. Top, F. Martial, C. Gros, M. J. McGlinchey, et G. Jaouen, « Side-Chain Effects on the 1-(Bis-aryl-methylidene)-[3]ferrocenophane Skeleton: Antiproliferative Activity against TNBC Cancer Cells and Comparison with the Acyclic Ferrocifen Series », European Journal of Inorganic Chemistry, vol. 2017, nᵒ 2, p. 454-465, janv. 2017.
    Résumé : As part of our ongoing study of the toxicity of compounds derived from 1,1-bis(4-hydroxyphenyl)-2-ferrocenylbut-1-ene, we have recently shown that closely analogous [3]ferrocenophane complexes have an in vitro toxicity level substantially higher than that of their ferrocene counterparts, particularly in the case of mono- and diphenol complexes. In this study we have examined whether the presence of a dimethylamino chain, analogous to the chain in hydroxytamoxifen, is capable of producing in the ferrocenophane series the same antiestrogenic effect observed for OH-Tam and Fc-OH-Tam. To this end, we have synthesized and characterized new complexes bearing various side-chains [O(CH2)3NMe2, O(CH2)3piperidine, O(CH2)3pyrrolidine, NHCO(CH2)2NMe2] and studied the biochemical properties of those complexes possessing appropriate solubility. The results revealed that the new complexes of [3]ferrocenophane have very strong antiproliferative effects; one of the compounds bearing an NHCO(CH2)2NMe2 chain has an IC50 value of 0.05 ± 0.02 µm for MDA-MB-231 breast cancer cells. All the complexes showed affinity for the estradiol receptor. At the low (nanomolar range) concentrations at which the estrogenic/antiestrogenic effect is expressed in these molecules, the presence of an amino-substituted side-chain does not induce in the [3]ferrocenophane series the antiestrogenic effect observed with OH-Tam and Fc-OH-Tam. However, this effect has been found for the complex with a slightly longer chain [O(CH2)4NMe2].
    Mots-clés : Antitumor agents, Bioorganometallic chemistry, CHEMBIO, Ferrocene, POLE 3, substituent effects, Toxicity.
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  • P. Hazel, S. H. B. Kroll, A. Bondke, M. Barbazanges, H. Patel, M. J. Fuchter, R. C. Coombes, S. Ali, A. G. M. Barrett, et P. S. Freemont, « Inhibitor Selectivity for Cyclin-Dependent Kinase 7: A Structural, Thermodynamic, and Modelling Study », ChemMedChem, vol. 12, nᵒ 5, p. 372-380, 2017.
    Résumé : Deregulation of the cell cycle by mechanisms that lead to elevated activities of cyclin-dependent kinases (CDK) is a feature of many human diseases, cancer in particular. We identified small-molecule inhibitors that selectively inhibit CDK7, the kinase that phosphorylates cell-cycle CDKs to promote their activities. To investigate the selectivity of these inhibitors we used a combination of structural, biophysical, and modelling approaches. We determined the crystal structures of the CDK7-selective compounds ICEC0942 and ICEC0943 bound to CDK2, and used these to build models of inhibitor binding to CDK7. Molecular dynamics (MD) simulations of inhibitors bound to CDK2 and CDK7 generated possible models of inhibitor binding. To experimentally validate these models, we gathered isothermal titration calorimetry (ITC) binding data for recombinant wild-type and binding site mutants of CDK7 and CDK2. We identified specific residues of CDK7, notably Asp155, that are involved in determining inhibitor selectivity. Our MD simulations also show that the flexibility of the G-rich and activation loops of CDK7 is likely an important determinant of inhibitor specificity similar to CDK2.
    Mots-clés : cancer, CDK7, drug discovery, isothermal titration calorimetry, MACO, POLE 1, protein kinases.
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  • L. Le Falher, A. Mumtaz, A. Nina Diogo, S. Thorimbert, et C. Botuha, « Chemoselective Access to π-Conjugated Heterocycles by Stille and Sonogashira Reactions on 2-Substituted 4H-Pyrido[e][1,3]oxazin-4-ones », European Journal of Organic Chemistry, vol. 2017, nᵒ 4, p. 827-832, janv. 2017.
    Résumé : Site-selective PdII-catalyzed cross-coupling reactions of 2-substituted-4H-pyrido[e][1,3]oxazin-4-ones were developed. C4- and C5-alkynylated pyridooxazinones were thus obtained through Sonogashira coupling, whereas the efficient incorporation of (hetero)aryl and ethenyl substituents at the C5 position was achieved by Stille coupling. Finally, an example of one-pot sequential multiple Sonogashira reactions with different alkynes was realized. The strategy developed herein provides rapid access to polyfunctionalized precursors with extended π-conjugation for further application as fluorescent materials.
    Mots-clés : CHEMBIO, cross-coupling, Fluorescent probes, heterocycles, homogeneous catalysis, Palladium, POLE 3.
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  • M. Malacria, N. Della Ca’, E. Motti, et G. Maestri, « Palladium- and Norbornene-Catalyzed Synthesis of Highly Functionalized Thiophenes: The Remarkable Effect of Electron-Poor Olefins as Ligand », HETEROCYCLES, vol. 95, nᵒ 2, p. 753, 2017.


  • A. Monfredini, V. Santacroce, L. Marchiò, R. Maggi, F. Bigi, G. Maestri, et M. Malacria, « Semi-Reduction of Internal Alkynes with Prototypical Subnanometric Metal Surfaces: Bridging Homogeneous and Heterogeneous Catalysis with Trinuclear All-Metal Aromatics », ACS Sustainable Chemistry & Engineering, vol. 5, nᵒ 9, p. 8205-8212, sept. 2017.
    Résumé : Suitably delocalized metal–metal bonds can stabilize a particular class of discrete trinuclear complexes that are the transition-metal counterparts of carbon-based aromatics. This chemical stability has pivoted the development of an advantageous catalytic method for the semireduction of internal alkynes under transfer hydrogenation condition. The reaction does not require any additional solvent and a simple workup delivers pure products. This combines with broad functional group tolerance, complete cis-selectivity and catalytic charges down to 100 ppm on multigram scale.
    Mots-clés : MACO, POLE 1.
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  • P. Pigeon, Y. Wang, S. Top, F. Najlaoui, M. C. G. Alvarez, J. Bignon, M. J. McGlinchey, et G. Jaouen, « A New Series of Succinimido-ferrociphenols and Related Heterocyclic Species Induce Strong Antiproliferative Effects, Especially against Ovarian Cancer Cells Resistant to Cisplatin », Journal of medicinal chemistry, vol. 60, nᵒ 20, p. 8358-8368, oct. 2017.


  • M. Piot, S. Hupin, H. Lavanant, C. Afonso, L. Bouteiller, A. Proust, et G. Izzet, « Charge Effect on the Formation of Polyoxometalate-Based Supramolecular Polygons Driven by Metal Coordination », Inorganic Chemistry, vol. 56, nᵒ 14, p. 8490-8496, juill. 2017.
    Résumé : The metal-driven self-assembly of a Keggin-based hybrid bearing two remote pyridine units was investigated. The resulting supramolecular species were identified by combination of 2D diffusion NMR spectroscopy (DOSY) and electrospray ionization mass spectrometry (ESI-MS) as a mixture of molecular triangles and squares. This behavior is different from that of the structural analogue Dawson-based hybrid displaying a higher charge, which only led to the formation of molecular triangles. This study highlights the decisive effect of the charge of the POMs in their self-assembly processes that disfavors the formation of large assemblies. An isothermal titration calorimetry (ITC) experiment confirmed the stronger binding in the case of the Keggin hybrids. A correlation between the diffusion coefficient D and the molecular mass M of the POM-based building block and its coordination oligomers was also observed. We show that the diffusion coefficient of these compounds is mainly determined by their occupied volume rather than by their shape.
    Mots-clés : E-POM, POLE 2, POL

    E 4, POLYMERES.
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  • L. Pocquet, N. Vologdin, G. F. Mangiatordi, I. Ciofini, O. Nicolotti, S. Thorimbert, et M. Salmain, « Supramolecular Anchoring of NCN-Pincer Palladium Complexes into a β-Barrel Protein Host: Molecular-Docking and Reactivity Insights », European Journal of Inorganic Chemistry, vol. 2017, nᵒ 30, p. 3622-3634, août 2017.
    Résumé : Several prochiral NCN-pincer complexes of palladium(II), with hemilabile ligands and a long aliphatic chain, were synthesized and characterized spectroscopically. In some of the complexes, the presence of two different substituents on the N donor atoms made them stereogenic, so that they were isolated as a mixture of diastereoisomers, which could be differentiated by 1H NMR spectroscopy. Binding of some of these complexes to bovine β-lactoglobin by insertion within its inner cavity was theoretically investigated by molecular-docking simulations and was experimentally confirmed by CD spectroscopy. Adjunction of H-bond donor substituents on the ligand framework gave more-stable supramolecular protein–complex assemblies. These constructs were shown to catalyze aldol condensation reactions in aqueous media, affording, in some cases, the less-favorable cis product. Since the corresponding complexes exclusively gave the trans product in the absence of β-lactoglobulin, this unusual diastereoselectivity was ensued by the second sphere of coordination brought by the protein host.
    Mots-clés : Aldol reactions, CHEMBIO, Docking, Metalloenzymes, Palladium, POLE 3, β-Lactoglobulin.
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  • V. Santacroce, R. Duboc, M. Malacria, G. Maestri, et G. Masson, « Visible-Light, Photoredox-Mediated Oxidative Tandem Nitroso-Diels–Alder Reaction of Arylhydroxylamines with Conjugated Dienes », European Journal of Organic Chemistry, vol. 2017, nᵒ 15, p. 2095-2098, 2017.
    Résumé : Arylhydroxylamines were used in the nitroso-Diels–Alder reaction to generate in situ nitrosoarenes under visible-light, catalytic and aerobic conditions. Mixing a solution of aryl- or heteroarylhydroxylamines with conjuguated dienes in the presence of a catalytic amount of Ru(bpy)3Cl2 afforded 3,6-dihydro-1,2-oxazines in good yields under an oxygen atmosphere.
    Mots-clés : MACO, Nitrogen heterocycles, Nitroso-Diels–Alder reaction, Oxidative tandem, Photocatalysis, POLE 1, Radicals.
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  • 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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2015


  • D. Kréher, F. Mathevet, P. Baldeck, C. Ricard, B. V. D. Sanden, et A. - J. Attias, « PH responsive two-photon absorbing functionalized styrylpyridine-based multi-branched dyes », Nonlinear optics, Quantum optics, vol. 46, nᵒ 2, p. 283-297, janv. 2015.
    Résumé : We report on the design, synthesis and optical properties of new two-photon absorbing multi-branched chromophores, based on a pyridine core. Measurements of TPA using the two-photon fluorescence...
    Mots-clés : POLE 4, POLYMERES.
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  • D. Lesage, G. Barozzino-Consiglio, R. Duwald, C. Fressigné, A. Harrison-Marchand, K. F. Faull, J. Maddaluno, et Y. Gimbert, « A Lithium Amide Protected Against Protonation in the Gas Phase: Unexpected Effect of LiCl », The Journal of Organic Chemistry, vol. 80, nᵒ 12, p. 6441-6446, 2015.
    Résumé : In cold THF and in the presence of LiCl, a lithium pyrrolidinylamide forms a 1:1 mixed aggregate, which is observed directly by ESI-MS. Gas-phase protonation of this species leads to selective transfer of H+ to the chlorine, suggesting that LiCl shields the amide nitrogen and prevents its direct protonation.
    Mots-clés : CSOB, POLE 3.
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Année non précisée


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  • « Photoredox Catalysis, an Opportunity for Sustainable Radical Chemistry | Advanced Green Chemistry », sans date. [Online]. Available: https://www.worldscientific.com/doi/pdf/10.1142/9789811210587_0003?download=true. [Accessed: 21-mai-2021].

  • « Synthesis of α-oxygenated β,γ-unsaturated ketones by a catalytic rearrangement strategy - Organic & Biomolecular Chemistry (RSC Publishing) », sans date. [Online]. Available: https://pubs.rsc.org/en/content/articlelanding/2018/ob/c8ob01559g. [Accessed: 31-janv.-2023].

  • « Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light | Organic Letters », sans date. [Online]. Available: https://pubs.acs.org/doi/full/10.1021/acs.orglett.0c02193. [Accessed: 31-janv.-2023].

  • « Dimerizing cascades of enallenamides reveal the visible-light-promoted activation of cumulated C–C double bonds - Chemical Science (RSC Publishing) DOI:10.1039/D1SC06719B », sans date. [Online]. Available: https://pubs.rsc.org/en/content/articlehtml/2022/sc/d1sc06719b. [Accessed: 31-janv.-2023].

  • E. Masson, « Forty years of exchange interactions on the occasion of the 75th birthday of Michel Verdaguer », EM-Consulte, sans date. [Online]. Available: https://www.em-consulte.com/article/1309686/article/forty-years-of-exchange-interactions-on-the-occasi. [Accessed: 30-janv.-2023].
    Résumé : Forty years of exchange interactions on the occasion of the 75th birthday of Michel Verdaguer
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  • A. Nina-Diogo, B. Bertrand, S. Thorimbert, G. Gontard, S. Nassem-Kahn, A. Echeverri, J. Contreras-García, C. Allain, G. Lemercier, E. Luppi, et C. Botuha, « 3-Hydroxypyridinyl-Substituted-1,2,4-Triazoles as New ESIPT Based Fluorescent Dyes: Synthesis and Structure–Fluorescence Properties Correlations », Advanced Optical Materials, vol. n/a, nᵒ n/a, p. 2300336, sans date.
    Résumé : This report presents the design, synthesis, and photophysical study of two new series of promising fluorescent trisubstituted triazoles, 3-hydroxypyridinyl substituted-1,2,4-triazoles (PyOHTr) and 2-pyridonyl substituted-1,2,4-triazoles (PyCOTr). An excited state intramolecular proton transfer (ESIPT) fluorescence mechanism is evidenced for PyOHTr molecules by ab initio theoretical calculations. These fluorescent dyes possess unique optical properties such as large Stokes shifts, dual emission, solvatochromism, solid-state emission and, for one of them, a white light emission, rendering them particularly attractive for future applications in both medicinal chemistry and materials science.
    Mots-clés : 1, 2, 4-triazole, ab initio calculations, CHEMBIO, excited state intramolecular proton transfer (ESIPT), fluorescence, POLE 3, solid-state emission, Stokes shift, white light.
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  • F. A. de Oliveira, L. J. C. Albuquerque, G. Delecourt, V. Bennevault, P. Guégan, et F. C. Giacomelli, « Current Designs of Polymeric Platforms Towards the Delivery of Nucleic Acids Inside the Cells with Focus on Polyethylenimine », Current Gene Therapy, vol. 21, nᵒ 5, p. 431-451, sans date.
    Résumé : Background: Gene delivery is a promising technology for treating diseases linked to abnormal gene expression. Since nucleic acids are the therapeutic entities in such approach, a transfecting vector is required because the macromolecules are not able to efficiently enter the cells by themselves. Viral vectors have been evidenced to be highly effective in this context; however, they suffer from fundamental drawbacks, such as the ability to stimulate immune responses. The development of synthetic vectors has accordingly emerged as an alternative. Objectives: Gene delivery by using non-viral vectors is a multi-step process that poses many challenges, either regarding the extracellular or intracellular media. We explore the delivery pathway and afterwards, we review the main classes of non-viral gene delivery vectors. We further focus on the progresses concerning polyethylenimine-based polymer-nucleic acid polyplexes, which have emerged as one of the most efficient systems for delivering genetic material inside the cells. Discussion: The complexity of the whole transfection pathway, along with a lack of fundamental understanding, particularly regarding the intracellular trafficking of nucleic acids complexed to non-viral vectors, probably justifies the current (beginning of 2021) limited number of formulations that have progressed to clinical trials. Truly, successful medical developments still require a lot of basic research. Conclusion: Advances in macromolecular chemistry and high-resolution imaging techniques will be useful to understand fundamental aspects towards further optimizations and future applications. More investigations concerning the dynamics, thermodynamics and structural parameters of polyplexes would be valuable since they can be connected to the different levels of transfection efficiency hitherto evidenced.
    Mots-clés : POLYMERES.
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