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  • E. Benazzi, J. Karlsson, Y. Ben M'Barek, P. Chabera, S. Blanchard, S. Alves, A. Proust, T. Pullerits, G. Izzet, et E. A. Gibson, « Acid-triggering of light-induced charge-separation in hybrid organic/inorganic molecular photoactive dyads for harnessing solar energy », Inorganic Chemistry Frontiers, vol. 8, nᵒ 6, p. 1610-1618, 2021.
    Résumé : H + modulated charge-transfer in photoexcited covalently linked W and Mo Keggin-bodipy conjugates is demonstrated using transient absorption spectroscopy and photoluminescence. Adding acid switches on (W) or accelerates (Mo) charge separation. , H + modulated charge-transfer in photoexcited covalent polyoxometalate-bodipy conjugates is described. The hybrid organic/inorganic molecular photoactive dyads are based on Keggin-type polyoxometalates (POMs, where K M = [PM 11 O 39 ] and M = Mo or W) covalently grafted via an organotin linker to a bodipy (BOD) photosensitizer. The relative potentials of the photosensitizer and POM are aligned such that light-induced electron transfer from BOD to POM is permitted for the polyoxomolybdate KMoSn[BOD] but not effective for the polyoxotungstate analogue KWSn[BOD] . In both cases, the addition of acid shifts the redox potential of the POM only, to increase the driving force for electron transfer. This leads to charge-separation being switched on for KWSn[BOD] in the presence of acid. The addition of acid to KMoSn[BOD] accelerates charge-separation by an order of magnitude (from 2 ns to 200 ps) and is accompanied by a deceleration of charge recombination, leading to a charge-separated state lifetime of up to 1.3 μs. This behaviour is consistent with proton coupled electron transfer, which has previously been observed electrochemically for POMs, but this study shows, for the first time, the impact of protonation on photoinduced electron transfer.
    Mots-clés : CSOB, E-POM, POLE 2, POLE 3.

  • H. Dossmann, L. Fontaine, T. Weisgerber, V. Bonnet, E. Monflier, A. Ponchel, et C. Przybylski, « First Steps to Rationalize Host–Guest Interaction between α-, β-, and γ-Cyclodextrin and Divalent First-Row Transition and Post-transition Metals (Subgroups VIIB, VIIIB, and IIB) », Inorganic Chemistry, vol. 60, nᵒ 2, p. 930-943, janv. 2021.
    Mots-clés : CSOB, Cyclodextrin, POLE 3.

  • D. Gatineau, H. Dossmann, H. Clavier, A. Memboeuf, L. Drahos, Y. Gimbert, et D. Lesage, « Ligand effects in gold-carbonyl complexes: evaluation of the bond dissociation energies using blackbody infrared radiative dissociation », International Journal of Mass Spectrometry, p. 116545, févr. 2021.

  • S. Khodjoyan, E. Remadna, H. Dossmann, D. Lesage, G. Gontard, J. Forté, H. Hoffmeister, U. Basu, I. Ott, P. Spence, Z. Waller, M. Salmain, et B. Bertrand, « [(C^C)Au(N^N)]+ complexes as a new family of anticancer candidates: synthesis, characterization and exploration of the antiproliferative properties », Chemistry – A European Journal, vol. n/a, nᵒ n/a, 2021.
    Résumé : A library of eleven cationic gold(III) complexes of the general formula [(C^C)Au(N^N)] + when C^C is either biphenyl or 4,4’-ditertbutyldiphenyl and N^N is a bipyridine, phenanthroline or dipyridylamine derivative have been synthesized and characterized. Contrasting effects on the viability of the triple negative breast cancer cells MDA-MB-231 was observed from a preliminary screening. The antiproliferative activity of the seven most active complexes were further assayed on a larger panel of human cancer cells as well as on non-cancerous cells for comparison. Two complexes stood out for being either highly active or highly selective. Eventually, reactivity studies with biologically meaningful amino acids, glutathione, higher order DNA structures and thioredoxin reductase (TrxR) revealed a markedly different behavior from that of the well-known coordinatively isomeric [(C^N^C)Au(NHC)] + structure. This makes the [(C^C)Au(N^N)] + complexes a new class of organogold compounds with an original mode of action.
    Mots-clés : Bioorganometallics, Biphenyl, Cancer, Chelate, CHEMBIO, CSOB, Gold, POLE 3.

  • J. Liu, B. Wang, C. Przybylski, O. Bistri‐Aslanoff, M. Ménand, Y. Zhang, et M. Sollogoub, « Programmed Synthesis of Hepta‐Differentiated β‐Cyclodextrin: 1 out of 117655 Arrangements », Angewandte Chemie International Edition, vol. 60, nᵒ 21, p. 12090-12096, mai 2021.
    Mots-clés : CSOB, GOBS, POLE 3.

  • C. Przybylski et V. Bonnet, « Discrimination of isomeric trisaccharides and their relative quantification in honeys using trapped ion mobility spectrometry », Food Chemistry, vol. 341, p. 128182, 2021.

  • E. Rathahao-Paris, S. Alves, et A. Paris, « High-Throughput Metabolomics Using Flow Injection Analysis and Fourier Transform Ion Cyclotron Resonance Mass Spectrometry », in Metabolomics, vol. 159, New York, NY: Humana, 2021, p. 9-23.
    Résumé : The hyphenation of flow injection analysis (FIA) with Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) is an efficient approach usable to perform high throughput and very high resolution metabolomic data acquisition. Instrumental and analytical conditions for performing FIA-MS are provided. The procedure to optimize dilution factor of biological samples as well as to evaluate quality of acquisition data are also described. In this protocol, urine is chosen as a matrix example to illustrate the application of procedures. Last, some indications on an adapted data processing are given.
    Mots-clés : CSOB, POLE 3.


  • S. Alves, A. Paris, et E. Rathahao-Paris, « Mass spectrometry-based metabolomics for an in-depth questioning of human health », in Advances in Clinical Chemistry, Elsevier, 2020, p. S0065242320300214.

  • P. Bayat, D. Lesage, et R. B. Cole, « Tutorial: Ion activation in tandem Mass spectrometry using ultra-high resolition spectroscopy », Mass Spectrometry Reviews, p. mas.21623, févr. 2020.

  • L. Bedoin, S. Alves, et J. - F. Lambert, « Origins of Life and Molecular Information: Selectivity in Mineral Surface-Induced Prebiotic Amino Acid Polymerization », ACS Earth and Space Chemistry, p. acsearthspacechem.0c00183, sept. 2020.

  • B. Bertrand, C. Botuha, J. Forté, H. Dossmann, et M. Salmain, « A bis-chelating (O^N^O)/(N^N) ligand for the synthesis of heterobimetallic Pt(II)/Re(I) complexes: tools for the optimization of a new class of Pt(II) anticancer agents. », Chemistry – A European Journal, vol. 26, nᵒ 56, p. 12846-12861, juin 2020.
    Résumé : The two independent (O^N^O) and (N^N) coordination sites of a newly synthesized bis 2-(hydroxyphenyl)-1,2,4-triazole platform have been exploited to prepare four monometallic neutral (O^N^O)Pt(II) complexes carrying DMSO, pyridine, triphenylphosphine or N-heterocyclic carbene (NHC) as fourth ligand. Then the second (N^N) coordination site was used to introduce an IR-active rhenium tricarbonyl entity, affording the four corresponding heterobimetallic neutral Pt(II)/Re(I) complexes as well as a cationic Pt(II)/Re(I) derivative. X-ray crystallographic studies showed that distortion of the organic platform occurred to accommodate the coordination geometry of both metal centers. No ligand exchange and no transchelation occurred upon incubation of the Pt(II) complexes in aqueous environment or in the presence of Fe(III), respectively. The ligand and the complexes antiproliferative activity was first screened on the triple negative breast cancer cell line MDA-MB-231. Then the IC 50 of the most active candidates was determined on a wider panel of human cancer cells (MDA-MB-231, MCF-7 and A2780) as well as on a non-tumorigenic cell line (MCF-10F). Low micromolar activities were reached for the complexes carrying a DMSO ligand, making them the first examples of highly active though hydrolytically stable Pt(II) complexes. Finally, the characteristic mid-IR signature of the Re(CO) 3 fragment in the Pt/Re heterobimetallic complexes was used to quantify their uptake in breast cancer cells.
    Mots-clés : cancer, CHEMBIO, CSOB, heterobimetallic, pincer, platinum, POLE 3, rhenium.
    Note Note
    <p>doi: 10.1002/chem.202001752</p>

  • R. B. Cole, P. Bayat, J. S. Murray, C. Albers, et D. Brombach, « “Conformation pinning” by anion attachment enabling separation of isomeric steroid monomers by ion mobility spectrometry », Journal of Mass Spectrometry, vol. 55, nᵒ 12, déc. 2020.

  • A. Delvaux, E. Rathahao‐Paris, et S. Alves, « An emerging powerful technique for distinguishing isomers: Trapped Ion Mobility Spectrometry ‐ Time‐of‐Flight Mass Spectrometry for a rapid characterization of estrogen isomers », Rapid Communications in Mass Spectrometry, août 2020.

  • H. Dossmann, D. Gatineau, H. Clavier, A. Memboeuf, D. Lesage, et Y. Gimbert, « Exploring Phosphine Electronic Effects on Molybdenum Complexes: A Combined Photoelectron Spectroscopy and Energy Decomposition Analysis Study », The Journal of Physical Chemistry A, p. acs.jpca.0c06746, oct. 2020.

  • J. A. Hawkes, J. D'Andrilli, J. N. Agar, M. P. Barrow, S. M. Berg, N. Catalán, H. Chen, R. K. Chu, R. B. Cole, T. Dittmar, R. Gavard, G. Gleixner, P. G. Hatcher, C. He, N. J. Hess, R. H. S. Hutchins, A. Ijaz, H. E. Jones, W. Kew, M. Khaksari, D. C. Palacio Lozano, J. Lv, L. R. Mazzoleni, B. E. Noriega‐Ortega, H. Osterholz, N. Radoman, C. K. Remucal, N. D. Schmitt, S. K. Schum, Q. Shi, C. Simon, G. Singer, R. L. Sleighter, A. Stubbins, M. J. Thomas, N. Tolic, S. Zhang, P. Zito, et D. C. Podgorski, « An international laboratory comparison of dissolved organic matter composition by high resolution mass spectrometry: Are we getting the same answer? », Limnology and Oceanography: Methods, vol. 18, nᵒ 6, p. 235-258, 2020.

  • M. Laurans, K. Trinh, K. Dalla Francesca, G. Izzet, S. Alves, E. Derat, V. Humblot, O. Pluchery, D. Vuillaume, S. Lenfant, F. Volatron, et A. Proust, « Covalent Grafting of Polyoxometalate Hybrids onto Flat Silicon/Silicon Oxide: Insights from POMs Layers on Oxides », ACS Applied Materials & Interfaces, vol. 12, nᵒ 42, p. 48109-48123, oct. 2020.
    Résumé : Immobilization of polyoxometalates (POMs) onto oxides is relevant to many applications in the fields of catalysis, energy conversion/storage, or molecular electronics. Optimization and understanding the molecule/oxide interface is crucial to rationally improve the performance of the final molecular materials. We herein describe the synthesis and covalent grafting of POM hybrids with remote carboxylic acid functions onto flat Si/SiO2 substrates. Special attention has been paid to the characterization of the molecular layer and to the description of the POM anchoring mode at the oxide interface through the use of various characterization techniques, including ellipsometry, AFM, XPS, and FTIR. Finally, electron transport properties were probed in a vertical junction configuration and energy level diagrams have been drawn and discussed in relation with the POM molecular electronic features inferred from cyclic-voltammetry, UV–visible absorption spectra, and theoretical calculations. The electronic properties of these POM-based molecular junctions are driven by the POM LUMO (d-orbitals) whatever the nature of the tether or the anchoring group.
    Mots-clés : CSOB, E-POM, MACO, POLE 1, POLE 2, POLE 3.
    Pièce jointe Full Text PDF 6.8 Mo (source)

  • Z. Li, T. Bavaro, S. Tengattini, R. Bernardini, M. Mattei, F. Annunziata, R. B. Cole, C. Zheng, M. Sollogoub, L. Tamborini, M. Terreni, et Y. Zhang, « Chemoenzymatic synthesis of arabinomannan (AM) glycoconjugates as potential vaccines for tuberculosis », European Journal of Medicinal Chemistry, vol. 204, p. 112578, 2020.
    Mots-clés : CSOB, GOBS, POLE 3.

  • F. Nolay, E. Sevin, M. Létévé, A. Bil, F. Gosselet, K. El Kirat, F. Djedaini-Pilard, S. Morandat, L. Fenart, C. Przybylski, et V. Bonnet, « First step to the improvement of the blood brain barrier passage of atazanavir encapsulated in sustainable bioorganic vesicles », International Journal of Pharmaceutics, vol. 587, p. 119604, 2020.

  • E. Palierse, C. Przybylski, D. Brouri, C. Jolivalt, et T. Coradin, « Interactions of Calcium with Chlorogenic and Rosmarinic Acids: An Experimental and Theoretical Approach », International Journal of Molecular Sciences, vol. 21, nᵒ 14, p. 4948, juill. 2020.
    Résumé : Chlorogenic (CA) and rosmarinic (RA) acids are two natural bioactive hydroxycinnamic acids whose antioxidant properties can be modulated by the chelation of metal ions. In this work, the interactions of these two carboxylic phenols with calcium ions and the impact of such interactions on their antioxidant activity were investigated. UV-Vis absorbance, mass spectroscopy and 1H and 13C liquid NMR were used to identify complexes formed by CA and RA with calc

    ium. Antioxidant activities were measured by the Bois method. Density functional theory (DFT) calculations were performed to evaluate the most stable configurations and correlated with NMR data. Taken together, these data suggest that calcium ions mainly interact with the carboxylate groups of both molecules but that this interaction modifies the reactivity of the catechol groups, especially for RA. These results highlight the complex interplay between metal chelation and antioxidant properties of natural carboxylic phenols.
    Mots-clés : CSOB, POLE 3.

  • C. Tugny, N. del Rio, M. Koohgard, N. Vanthuyne, D. Lesage, K. Bijouard, P. Zhang, J. Meijide Suárez, S. Roland, E. Derat, O. Bistri-Aslanoff, M. Sollogoub, L. Fensterbank, et V. Mouriès-Mansuy, « β-Cyclodextrin–NHC–Gold(I) Complex (β-ICyD)AuCl: A Chiral Nanoreactor for Enantioselective and Substrate-Selective Alkoxycyclization Reactions », ACS Catalysis, vol. 10, nᵒ 11, p. 5964-5972, juin 2020.
    Résumé : NHC-capped β-cyclodextrin (β-ICyD) was used as a ligand for gold-catalyzed alkoxycyclization reactions. The cavity was found to be responsible for a triple selectivity: (i) the asymmetric shape of the cavity of β-ICyD induced highly stereoselective cyclizations, (ii) the shape of the interior favored the formation of a six-membered ring in the absence of a nucleophile, and finally, (iii) the encapsulation of the metal inside the cavity disfavored the addition of sterically hindered alcohols. Highly enantioselective and substrate-selective alkoxycyclizations of enynes are therefore promoted by the cavity-based molecular reactor (β-ICyD)AuCl.
    Mots-clés : CSOB, GOBS, MACO, POLE 1, POLE 3.
    Pièce jointe Full Text PDF 2.2 Mo (source)

  • Z. Wang, D. Landy, C. Sizun, C. Cézard, A. Solgadi, C. Przybylski, L. de Chaisemartin, L. Herfindal, G. Barratt, et F. - X. Legrand, « Cyclodextrin complexation studies as the first step for repurposing of chlorpromazine », International Journal of Pharmaceutics, vol. 584, p. 119391, 2020.


  • U. Alali, A. Vallin, A. Bil, T. Khanchouche, D. Mathiron, C. Przybylski, R. Beaulieu, J. Kovensky, M. Benazza, et V. Bonnet, « The uncommon strong inhibition of α-glucosidase by multivalent glycoclusters based on cyclodextrin scaffolds », Organic & Biomolecular Chemistry, vol. 17, nᵒ 30, p. 7228-7237, 2019.
    Résumé : New inhibitors of α-glucosidase based on perglycosylated cyclodextrins were synthesized via click-chemistry and compared to acarbose. , The homeostasis disruption of d -glucose causes diabetes, a dramatic chronic disease worldwide. Type 1 diabetes is a successfully treatable form, where blood d -glucose is regulated by insulin treatment. In contrast type 2 diabetes, the non-insulin dependent kind, is problematic. The control of the d -glucose blood level via intestinal α- d -glucosidase inactivation can be achieved by using competitive inhibitors, such as iminosugars ( e.g. acarbose) or sulfonium sugar derivatives ( e.g. salacinol). Recently, an unprecedented result showed that multivalent diamond nanoparticles grafted with unmodified sugars displayed α-glucosidase inhibition at low micromolar concentrations. Herein we describe the synthesis of multivalent glycoclusters using cyclodextrins (CDs) as scaffolds and an assessment of their role as inhibitors of α- d -glucosidase. The glycoclusters were efficiently obtained from per-azido α, β and γ-CD derivatives and propargyl glycosides using click-chemistry under microwave irradiation. The methodology was successfully applied to various protected and non-protected propargylated monosaccharides, including both O - and S -glycosides, giving clear evidence of its versatility. The targeted 6- per -glycosylated CDs were isolated in moderate to excellent yields (30–90%) by silica gel chromatography. The results showed inhibition of α-glucosidase from Saccharomyces cerevisiae with IC 50 values in the 32–132 μM range, lower than that of acarbose (IC 50 = ∼250 μM), a well-known competitive inhibitor used in the clinical treatment of type 2 diabetes. Preliminary experiments suggest a mixed-type non-competitive inhibition mode for these new glycoclusters.
    Mots-clés : CSOB, POLE 3.

  • P. Bayat, D. Gatineau, D. Lesage, S. Marhabaie, A. Martinez, et R. B. Cole, « Investigation of activation energies for dissociation of host-guest complexes in the gas phase using low-energy collision induced dissociation », Journal of Mass Spectrometry, vol. 54, nᵒ 5, p. 437-448, 2019.

  • M. Cassé, C. Nisole, H. Dossmann, Y. Gimbert, J. - M. Fourquez, L. Haberkorn, C. Ollivier, et L. Fensterbank, « Trifluoromethyl radical triggered radical cyclization of <italic>N</italic>-benzoyl ynamides leading to isoindolinones », SCIENCE CHINA Chemistry, vol. 62, nᵒ 11, p. 1542-1546, oct. 2019.
    Résumé : Under photocatalytic reductive conditions, trifluoromethyl radical addition onto an ynamide followed by cyclization on a benzoyl moiety produces diverse isoindolinone platforms with good yields. The selectivity of the radical cyclization, <italic>N</italic>-benzoyl vs. <italic>N</italic>-benzyl as radical acceptor and the <italic>E</italic>/<italic>Z</italic> ratio of isomers have been rationalized by modeling.
    Mots-clés : CSOB, MACO, POLE 1, POLE 3.
    Pièce jointe Full Text PDF 1.6 Mo (source)

  • B. Colsch, A. Damont, C. Junot, F. Fenaille, et J. - C. Tabet, « Experimental evidence that electrospray-produced sodiated lysophosphatidyl ester structures exist essentially as protonated salts », European Journal of Mass Spectrometry, vol. 25, nᵒ 3, p. 333-338, 2019.

  • A. Damont, M. - F. Olivier, A. Warnet, B. Lyan, E. Pujos-Guillot, E. L. Jamin, L. Debrauwer, S. Bernillon, C. Junot, J. - C. Tabet, et F. Fenaille, « Proposal for a chemically consistent way to annotate ions arising from the analysis of reference compounds under ESI conditions: A prerequisite to proper mass spectral database constitution in metabolomics », Journal of Mass Spectrometry, vol. 54, nᵒ 6, p. 567-582, 2019.

  • G. Gaiffe, R. B. Cole, A. Sonnette, N. Floch, et M. C. Bridoux, « Identification of Postblast Residues by DART-High Resolution Mass Spectrometry Combined with Multivariate Statistical Analysis of the Kendrick Mass Defect », Analytical Chemistry, vol. 91, nᵒ 13, p. 8093-8100, juill. 2019.

  • M. Girardi, D. Platzer, S. Griveau, F. Bedioui, S. Alves, A. Proust, et S. Blanchard, « Assessing the Electrocatalytic Properties of the Cp*RhIII2+-Polyoxometalate Derivative [H2PW11O39RhIIICp*(OH2)]3– towards CO2 Reduction », European Journal of Inorganic Chemistry, vol. 2019, nᵒ 3-4, p. 387-393, 2019.
    Résumé : Storage of electricity produced intermittently by renewable energy sources is a societal issue. Besides the use of batteries and supercapacitors, conversion of excess electricity into chemical energy is also actively investigated. The conversion of CO2 to fuel or fuel precursors is an option that requires the use of a catalyst to overcome the high activation energy barrier. Of molecular catalysts, metal complexes with polypyridyl ligands are well represented, among which the [Cp*Rh(bpy)Cl]+ and [M(bpy)(CO)3X] (M = Re, Mn) complexes. As redox non-innocent ligand, the bipyridine ligand is generally involved in the reduction mechanisms. It is thus tempting to replace it by other redox non-innocent ligands such as vacant polyoxometalates (POMs). We have thus prepared [α-H2PW11O39RhIIICp*(OH2)]3– which is closely related to [Cp*RhIII(bpy)Cl]+ by substitution of the monovacant [PW11O39]7– Keggin-type POM for the bipyridine ligand. Its activity towards CO2 reduction has been assessed in acetonitrile in the presence of water. Compared to [Cp*Rh(bpy)Cl]+ that produces formate selectively over CO and H2, the POM derived catalyst favors proton reduction over CO2 reduction.
    Mots-clés : Carbon dioxide fixation, CSOB, E-POM, Non-innocent ligands, POLE 2, POLE 3, Polyoxometalates, Redox chemistry.
    Pièce jointe Full Text PDF 974.1 ko (source)

  • T. Hautbergue, E. L. Jamin, R. Costantino, S. Tadrist, L. Meneghetti, J. - C. Tabet, L. Debrauwer, I. P. Oswald, et O. Puel, « Combination of Isotope Labeling and Molecular Networking of Tandem Mass Spectrometry Data To Reveal 69 Unknown Metabolites Produced by <i>Penicillium nordicum</i> », Analytical Chemistry, vol. 91, nᵒ 19, p. 12191-12202, 2019.

  • E. L. Jamin, C. Jacques, L. Jourdes, J. - C. Tabet, N. Borotra, S. Bessou-Touya, L. Debrauwer, et H. Duplan, « Identification of lipids of the stratum corneum by high performance thin layer chromatography and mass spectrometry », European Journal of Mass Spectrometry, vol. 25, nᵒ 3, p. 278-290, 2019.

  • C. M. Kronfel, C. V. Hernandez, J. P. Frick, L. S. Hernandez, A. Gutu, J. A. Karty, M. N. Boutaghou, D. M. Kehoe, R. B. Cole, et W. M. Schluchter, « CpeF is the bilin lyase that ligates the doubly linked phycoerythrobilin on β-phycoerythrin in the cyanobacterium <i>Fremyella diplosiphon</i> », Journal of Biological Chemistry, p. jbc.RA118.007221, janv. 2019.

  • D. Lesage, S. Mezzache, Y. Gimbert, H. Dossmann, et J. - C. Tabet, « Extended kinetic method and RRKM modeling to reinvestigate proline’s proton affinity and approach the meaning of effective temperature », European Journal of Mass Spectrometry, p. 146906671882205, janv. 2019.

  • T. Neva, T. Carmona, J. M. Benito, C. Przybylski, C. Ortiz Mellet, F. Mendicuti, et J. M. García Fernández, « Dynamic Control of the Self-Assembling Properties of Cyclodextrins by the Interplay of Aromatic and Host-Guest Interactions », Frontiers in Chemistry, vol. 7, p. 72, 2019.
    Résumé : The presence of a doubly-linked naphthylene clip at the O-2I and O-3II positions in the secondary ring of -cyclodextrin (CD) derivatives promoted their self-assembly into head-to-head supramolecular dimers in which the aromatic modules act either as cavity extension walls (if the naphthalene moiety is 1,8-disubstituted) or as folding screens that separate the individual CD units (if 2,3-disubstituted). Dimer architecture is governed by the conformational properties of the monomer constituents, as determined by NMR, fluorescence, circular dichroism and computational techniques. In a second supramolecular organization level, the topology of the assembly directs host-guest interactions and, reciprocally, guest inclusion impacts the stability of the supramolecular edifice. Thus, inclusion of adamantane carboxylate, a well-known CD cavity-fitting guest, was found to either preserve the dimeric arrangement, leading to multicomponent species, or elicit dimer disruption. The ensemble of results highlights the potential of the approach to program self-organization and external stimuli responsiveness of CD devices in a controlled manner while keeping full diastereomeric purity.
    Mots-clés : CSOB, POLE 3.

  • C. Przybylski, V. Bonnet, et R. R. Vivès, « A microscale double labelling of GAG oligosaccharides compatible with enzymatic treatment and mass spectrometry », Chemical Communications, vol. 55, nᵒ 29, p. 4182-4185, 2019.

  • C. Przybylski, H. Ramoul, V. Bonnet, M. Abad, et N. Jarroux, « Harnessing Polyisobutylene by Rotaxanation with γ-Cyclodextrin: Opportunities for Making Smart Molecular Necklaces », Macromolecular Chemistry and Physics, vol. 220, nᵒ 5, p. 1800502, mars 2019.
    Résumé : Abstract A new type of polyrotaxane based on the threading of ?-cyclodextrins (?-CDs) along a highly hydrophobic polymer, polyisobutylene (PIB), is successfully prepared and finely characterized. The used radical coupling associated with tuned reaction time and temperature leads to a fast and controlled necklace synthesis with low reagent consumption. Synthesis exhibits appealing conversion and threading rates with almost 100% and 62?73%, respectively. A combination of well-established SEC and NMR techniques, with a more forefront MALDI-TOF MS approach, provides details on the original PIB and the resulting polyrotaxanes (M w, M n, PDI, and average number of ?-CD threaded). Interestingly, tetramethylguanidinium-2-(4-hydroxyphenylazo)benzoate in DMF for MALDI analysis is revealed as a suitable matrix to overcome solubility troubles widely observed with PIB. Moreover, rotaxanation appears as an alternative to the grafting of polar groups to modify/handle hydrophobic polymers. Such an approach offers new opportunities to achieve the synthesis, with unambiguous evidence, of new supramolecular necklaces based on highly hydrophobic polymers.
    Mots-clés : CSOB, cyclodextrins, mass spectrometry, POLE 3, polyisobutylene, polyrotaxane, radical coupling.
    Note Note
    <p>doi: 10.1002/macp.201800502</p>

  • E. Rathahao-Paris, S. Alves, N. Boussaid, N. Picard-Hagen, V. Gayrard, P. - L. Toutain, J. - C. Tabet, D. N. Rutledge, et A. Paris, « Evaluation and validation of an analytical approach for high-throughput metabolomic fingerprinting using direct introduction–high-resolution mass spectrometry: Applicability to classification of urine of scrapie-infected ewes », European Journal of Mass Spectrometry, vol. 25, nᵒ 2, p. 251-258, 2019.

  • I. Seffouh, C. Przybylski, A. Seffouh, R. El Masri, R. R. Vivès, F. Gonnet, et R. Daniel, « Mass spectrometry analysis of the human endosulfatase Hsulf-2 », Biochemistry and Biophysics Reports, vol. 18, p. 100617, 2019.
    Résumé : The human 6-O-endosulfatases HSulf-1 and -2 catalyze the region-selective hydrolysis of the 6-O-sulfate group of the glucosamine residues within sulfated domains of heparan sulfate, thereby ensuring a unique and original post-biosynthetic modification of the cell surface proteoglycans. While numerous studies point out the role of HSulf-2 in crucial physiological processes as well as in pathological conditions particularly in cancer, its structural organization in two chains and its functional properties remain poorly understood. In this study, we report the first characterization by mass spectrometry (MS) of HSulf-2. An average molecular weight of 133,115 Da was determined for the whole enzyme by MALDI-TOF MS, i.e. higher than the naked amino acid backbone (98,170 Da), highlighting a significant contribution of post-translational modifications. The HSulf-2 protein sequence was determined by Nano-LC-MS/MS, leading to 63% coverage and indicating at least four N-glycosylation sites at Asn 108, 147, 174 and 217. These results provide a platform for further structural investigations of the HSulf enzymes, aiming at deciphering the role of each chain in the substrate binding and specificities and in the catalytic activities.
    Mots-clés : 6--Endosulfatase, CSOB, Formylglycine, Heparan sulfate, HSulf-2, Mass spectrometry, POLE 3, Sulfatase.

  • C. Sonnendecker, S. Thürmann, C. Przybylski, F. D. Zitzmann, N. Heinke, Y. Krauke, K. Monks, A. A. Robitzki, D. Belder, et W. Zimmermann, « Large‐Ring Cyclodextrins as Chiral Selectors for Enantiomeric Pharmaceuticals », Angewandte Chemie International Edition, 2019.

  • N. Stojiljkovic, F. Leroux, S. Bubanj, M. - A. Popot, A. Paris, J. - C. Tabet, et C. Junot, « Tracking main environmental factors masking a minor steroidal doping effect using metabolomic analysis of horse urine by liquid chromatography–high-resolution mass spectrometry », European Journal of Mass Spectrometry, vol. 25, nᵒ 3, p. 339-353, 2019.

  • J. - C. Tabet, « A 50-year career working and teaching in the fast-moving field of mass spectrometry research », European Journal of Mass Spectrometry, vol. 25, nᵒ 2, p. 195-201, 2019.

  • M. Thomas, L. Stuani, E. Darii, C. Lechaplais, E. Pateau, J. - C. Tabet, M. Salanoubat, P. - L. Saaidi, et A. Perret, « De novo structure determination of 3-((3-aminopropyl)amino)-4-hydroxybenzoic acid, a novel and abundant metabolite in Acinetobacter baylyi ADP1 », Metabolomics, vol. 15, nᵒ 3, p. 45, 2019.

  • Z. Xia, V. Corcé, F. Zhao, C. Przybylski, A. Espagne, L. Jullien, T. L. Saux, Y. Gimbert, H. Dossmann, V. Mouriès-Mansuy, C. Ollivier, et L. Fensterbank, « Photosensitized oxidative addition to gold( i ) enables alkynylative cyclization of o -alkylnylphenols with iodoalkynes », Nature Chemistry, vol. 11, nᵒ 9, p. 797-805, sept. 2019.
    Résumé : Studies into gold-catalysed cross-coupling reactions have expanded over recent decades; however, oxidative addition to gold(i) complexes remains challenging. Now it has been shown that a dual catalytic transformation involving iridium photosensitization to trigger oxidative addition to organogold intermediates enables C(sp2)–C(sp) cross-coupling reactions that are useful for the alkynylation of benzofurans.
    Mots-clés : CHEMBIO, CSOB, MACO, POLE 1, POLE 3.
    Pièce jointe Full Text PDF 1.8 Mo (source)


  • L. Bacri, H. Mamad-Hemouch, C. Przybylski, B. Thiebot, G. Patriarche, N. Jarroux, et J. Pelta, « Biomimetic ion channels formation by emulsion based on chemically modified cyclodextrin nanotubes », Faraday Discussions, 2018.

  • P. Barbier Saint Hilaire, U. M. Hohenester, B. Colsch, J. - C. Tabet, C. Junot, et F. Fenaille, « Evaluation of the High-Field Orbitrap Fusion for Compound Annotation in Metabolomics », Analytical Chemistry, vol. 90, nᵒ 5, p. 3030-3035, mars 2018.

  • C. K. Barik, R. Ganguly, Y. Li, C. Przybylski, M. Salmain, et W. K. Leong, « Embedding a Ruthenium-Based Structural Mimic of the [Fe]-Hydrogenase Cofactor into Papain », Inorganic Chemistry, vol. 57, nᵒ 19, p. 12206-12212, sept. 2018.
    Mots-clés : CHEMBIO, CSOB, POLE 3.

  • P. Bayat, D. Gatineau, D. Lesage, V. Robert, A. Martinez, et R. B. Cole, « Investigation of Hemicryptophane Host-Guest Binding Energies Using High-Pressure Collision-Induced Dissociation in Combination with RRKM Modeling », Journal of The American Society for Mass Spectrometry, nov. 2018.

  • P. Bayat, D. Lesage, et R. B. Cole, « Low-energy collision-induced dissociation (low-energy CID), collision-induced dissociation (CID), and higher energy collision dissociation (HCD) mass spectrometry for structural elucidation of saccharides and clarification of their dissolution mechanism i », Journal of Mass Spectrometry, vol. 53, nᵒ 8, p. 705-716, 2018.

  • F. A. Black, A. Jacquart, G. Toupalas, S. Alves, A. Proust, I. P. Clark, E. A. Gibson, et G. Izzet, « Rapid photoinduced charge injection into covalent polyoxometalate–bodipy conjugates », Chemical Science, vol. 9, nᵒ 25, p. 5578-5584, 2018.
    Mots-clés : CSOB, E-POM, POLE 2, POLE 3.

  • B. Brahim, J. - C. Tabet, et S. Alves, « Positive and negative ion mode comparison for the determination of DNA/peptide noncovalent binding sites through the formation of “three-body” noncovalent fragment ions », European Journal of Mass Spectrometry, vol. 24, nᵒ 1, p. 168-177, 2018.

  • de Jesús Cázares-Marinero José, Przybylski Cédric, et Salmain Michèle, « Proteins as Macromolecular Ligands for Metal-Catalysed Asymmetric Transfer Hydrogenation of Ketones in Aqueous Medium », European Journal of Inorganic Chemistry, vol. 2018, nᵒ 12, p. 1383-1393, 2018.
    Résumé : Biohybrid catalysts resulting from the dative anchoring of half-sandwich organometallic complexes [M(arene)(H2O)x(Cl)y]n+ (M = RuII, arene = ?6-benzene, p-cymene or mesitylene; M = IrIII, RhIII, arene = ?5-Cp*; x = 1?3, y = 0?2, n = 0?2) to bovine beta-lactoglobulin (?LG) or hen egg white lysozyme showed unprecedented behaviour. These constructs were shown to catalyse the asymmetric transfer hydrogenation of aryl ketones in water with sodium formate as hydrogen donor at a much faster rate than the complexes alone. Full conversion of the benchmark substrate 2,2,2-trifluoroacetophenone was reached with an ee of 86?% for the most selective biohybrid. Surprisingly, even the crude biohybrid gave a good ee despite the presence of non-protein-bound metal species in the reaction medium. Other aryl ketones were reduced in the same way, and the highest ee was obtained for ortho-substituted acetophenone derivatives. Furthermore, treatment of ?LG with dimethyl pyrocarbonate resulted in a noticeable decrease of the activity and selectivity of the biohybrid, indicating that the sole accessible histidine residue (His146) was probably involved in the coordination and activation of Ru(benzene). This work underscores that protein scaffolds are efficient chiral ligands for asymmetric catalysis. The use of sodium formate instead of dihydrogen makes this approach safe, inexpensive and environmentally friendly.
    Mots-clés : Artificial metalloenzymes, Asymmetric catalysis, CHEMBIO, CSOB, Hydrogenation, Mass spectrometry, POLE 3, Ruthenium.
    Note Note
    <p>doi: 10.1002/ejic.201701359</p>
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