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2021



  • C. Passirani, A. Vessières, G. La Regina, W. Link, and R. Silvestri, “Modulating undruggable targets to overcome cancer therapy resistance”, Drug Resistance Updates, vol. 60, p. 100788, Dec. 2021.
    Abstract: Many cancer patients frequently fail to respond to anti-cancer treatment due to therapy resistance which is the major obstacle towards curative cancer treatment. Therefore, identification of the molecular mechanisms underlying resistance is of paramount clinical and economic importance. The advent of targeted therapies based on a molecular understanding of cancer could serve as a model for strategies to overcome drug resistance. Accordingly, the identification and validation of proteins critically involved in resistance mechanisms represent a path towards innovative therapeutic strategies to improve the clinical outcome of cancer patients. In this review, we discuss emerging targets, small molecule therapeutics and drug delivery strategies to overcome therapy resistance. We focus on rational treatment strategies based on transcription factors, pseudokinases, nuclear export receptors and immunogenic cell death strategy. Historically, unliganded transcription factors and pseudokinases were considered undruggable while blocking the nuclear export e.g., through inhibition of the nuclear export receptor CRM1 was predicted as highly toxic. Recent success inhibiting Gli-1, HIF-1α, HIF-2α and reactivating the tumor suppressor transcription factors p53 and FOXO illustrates the feasibility and power of this targeting approach. Similarly, progress has been made in modulating the activity of pseudokinase proteins implicated in therapy resistance including members of the Tribbles protein family. On the other hand, the recent clinical approval of Selinexor, a specific inhibitor of CRM-1, a protein that mediates the transport of cargos with leucine-rich nuclear export signals and known to be a driver of drug resistance, represents the proof-of-concept for inhibiting the nuclear export as a feasible strategy to overcome therapy resistance. The ever-growing capacity to target resistance mechanisms with judiciously selected small molecules, some of which are being formulated within smart nanoparticles, will pave the way towards the improvement of the clinical outcome and realize the full potential of targeted therapies and immunotherapies.
    Tags: Cancer, CHEMBIO, drug development, drug resistance, nanomedicine, POLE 3, therapeutic targets.
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  • V. Pellas, J. Blanchard, C. Guibert, J. - M. Krafft, A. Miche, M. Salmain, and S. Boujday, “Gold Nanorod Coating with Silica Shells Having Controlled Thickness and Oriented Porosity: Tailoring the Shells for Biosensing”, ACS Applied Nano Materials, vol. 4, no. 9, p. 9842-9854, Aug. 2021.
    Abstract: The coating of gold nanorods with a silica shell (AuNR@SiO2) is an effective way to extend their use in a wide variety of biomedical applications including biosensing, drug delivery and photothermal therapy. A silica shell offers numerous advantages as it provides more stability, frees the surface from toxic cetyltrimethylammonium bromide (CTAB), and preserves the rod shape under photothermal conditions. This shell needs to be very thin for applications such as plasmonic biosensing, while a thicker and porous shell is suited for drug encapsulation and further controlled release. We introduce herein a strategy to perform silica coating based on dissociation of tetraethylorthosilicate (TEOS) hydrolysis and condensation reactions. This dissociation is achieved by a pH modulation of the reaction medium, and, depending on selected pH conditions, AuNR@SiO2 with a thick silica shell having an organized mesoporosity aligned either parallel (AuNR@//m-SiO2) or perpendicular (AuNR@⊥m-SiO2) to the AuNR surface was generated. Moreover, when mercaptopropyltrimethoxysilane (MPTMS) was used as a surface primer prior to TEOS condensation, ultrathin and homogeneous silica shells (AuNR@t-SiO2) of controllable thickness in the range 2–6 nm were produced. While formation, at high TEOS concentration, of core-free silica nanoparticles is evidenced by TEM analysis before the purification procedure, their total elimination during the purification step was achieved by addition of a suitable amount of CTAB to ensure the colloidal stability of the core-free and core–shell nanoparticles. Complete elimination of CTAB from AuNR@SiO2 was demonstrated by XPS, Raman, and ζ-potential measurements. Finally, the efficiency of AuNR@t-SiO2 in label-free plasmonic biosensing of a model target was demonstrated and their refractive index sensitivity factor was improved by 30% compared to CTAB-capped AuNRs.
    Tags: CHEMBIO, POLE 3.
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  • R. Ramos, J. - F. Gilles, R. Morichon, C. Przybylski, B. Caron, C. Botuha, A. Karaiskou, M. Salmain, and J. Sobczak-Thépot, “Cytotoxic BODIPY-Appended Half-Sandwich Iridium(III) Complex Forms Protein Adducts and Induces ER Stress”, Journal of Medicinal Chemistry, vol. 64, no. 22, p. 16675-16686, Nov. 2021.
    Abstract: Half-sandwich complexes of iridium(III) are currently being developed as anticancer drug candidates. In this context, we introduce IrBDP for which the C^N chelating phenyloxazoline ligand carries a fluorescent and lipophilic BODIPY reporter group, designed for intracellular tracking and hydrophobic compartment tropism. High-resolution analysis of cells cultured with IrBDP showed that it quickly permeates the plasma membrane and accumulates in the mitochondria and endoplasmic reticulum (ER), generating ER stress, dispersal of the Golgi apparatus, cell proliferation arrest and apoptotic cell death. Moreover, IrBDP forms fluorescent adducts with a subset of amino acids, namely histidine and cysteine, via coordination of N or S donor atoms of their side chains. Consistently, in vivo formation of covalent adducts with specific proteins is demonstrated, providing a molecular basis for the observed cytotoxicity and cellular response. Collectively, these results provide a new entry to the development of half-sandwich iridium-based anticancer drugs.
    Tags: CHEMBIO, CSOB, POLE 3.
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  • E. Rathahao-Paris, S. Alves, and 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.
    Abstract: 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.
    Tags: CSOB, POLE 3.
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  • M. Raynal, Y. Li, C. Troufflard, C. Przybylski, G. Gontard, T. Maistriaux, J. Idé, R. Lazzaroni, L. Bouteiller, and P. Brocorens, “Experimental and computational diagnosis of the fluxional nature of a benzene-1,3,5-tricarboxamide-based hydrogen-bonded dimer”, Physical Chemistry Chemical Physics, vol. 23, no. 9, p. 5207-5221, 2021.
    Abstract: High-symmetry (left) and low-symmetry ( e.g. that on the right) conformations of benzene-1,3,5-tricarboxamide dimers derived from glycine alkyl esters are in rapid exchange in solution through amide/ester competition for the binding of the N–H donors. , Precise characterization of the hydrogen bond network present in discrete self-assemblies of benzene-1,3,5-tricarboxamide monomers derived from amino-esters (ester BTAs) is crucial for the construction of elaborated functional co-assemblies. For all ester BTA dimeric structures previously reported, ester carbonyls in the side chain acted as hydrogen bond acceptors, yielding well-defined dimers stabilized by six hydrogen bonds. The ester BTA monomer derived from glycine ( BTA Gly ) shows a markedly different self-assembly behaviour. We report herein a combined experimental and computational investigation aimed at determining the nature of the dimeric species formed by BTA Gly . Two distinct dimeric structures were characterized by single-crystal X-ray diffraction measurements. Likewise, a range of spectroscopic and scattering techniques as well as molecular modelling were employed to diagnose the nature of dynamic dimeric structures in toluene. Our results unambiguously establish that both ester and amide carbonyls are involved in the hydrogen bond network of the discrete dimeric species formed by BTA Gly . The participation of roughly 4.5 ester carbonyls and 1.5 amide carbonyls per dimer as determined by FT-IR spectroscopy implies that several conformations coexist in solution. Moreover, NMR analysis and modelling data reveal rapid interconversion between these different conformers leading to a symmetric structure on the NMR timescale. Rapid hydrogen bond shuffling between conformers having three (three), two (four), one (five) and zero (six) amide carbonyl groups (ester carbonyl groups, respectively) as hydrogen bond acceptors is proposed to explain the magnetic equivalence of the amide N–H on the NMR timescale. When compared to other ester BTA derivatives in which only ester carbonyls act as hydrogen bond acceptors, the fluxional behaviour of the hydrogen-bonded dimers of BTA Gly likely originates from a larger range of energetically favorable conformations accessible through rotation of the BTA side chains.
    Tags: CSOB, POLE 3, POLE 4, POLYMERES.
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  • L. Simonin, G. Falco, S. Pensec, F. Dalmas, J. - M. Chenal, F. Ganachaud, A. Marcellan, L. Chazeau, and L. Bouteiller, “Macromolecular Additives to Turn a Thermoplastic Elastomer into a Self-Healing Material”, Macromolecules, vol. 54, no. 2, p. 888-895, Jan. 2021.
    Abstract: Self-healing allows increasing the service life of materials by overcoming some issues caused by mechanical failures. We propose a new concept to impart room-temperature self-healing properties to thermoplastic elastomers. A macromolecular additive whose interacting units can interfere with the hard segments of the thermoplastic elastomer accelerates chain dynamics and imparts self-healing properties to the composite material with a limited detrimental effect on mechanical properties. By applying this concept to silicone-based elastomers, we have obtained an autonomously self-healing material with a relatively high elastic modulus for this type of elastomers.
    Tags: POLYMERES.
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    Attachment Macromolecular Additives to Turn a Thermoplastic Elastomer into a Self-Healing2021_Simonin et al_.pdf
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  • J. - C. Tabet, Y. Gimbert, A. Damont, D. Touboul, F. Fenaille, and A. S. Woods, “Combining Chemical Knowledge and Quantum Calculation for Interpreting Low-Energy Product Ion Spectra of Metabolite Adduct Ions: Sodiated Diterpene Diester Species as a Case Study”, Journal of the American Society for Mass Spectrometry, vol. 32, no. 10, p. 2499-2504, Oct. 2021.


  • S. Topin-Ruiz, A. Mellinger, E. Lepeltier, C. Bourreau, J. Fouillet, J. Riou, G. Jaouen, L. Martin, C. Passirani, and N. Clere, “p722 ferrocifen loaded lipid nanocapsules improve survival of murine xenografted-melanoma via a potentiation of apoptosis and an activation of CD8+ T lymphocytes”, International Journal of Pharmaceutics, vol. 593, p. 120111, Jan. 2021.
    Abstract: Metastatic melanoma is a malignant tumor with a poor prognosis. Recent new therapeutics improved the survival of patients at a metastatic stage. However, the low response rate to immunotherapy, explained in part by resistance to apoptosis, needs to develop new strategies. The ferrocifen family represents promising bioorganometallic molecules for melanoma treatment since they show potent anticancer properties. The aim of this study is (i) to evaluate the benefits of a strategy involving encapsulated p722 in lipid nanocapsules (LNC) in B16F10 melanoma mice models and (ii) to compare the beneficial effects with an existing therapy such as anti-CTLA4 mAb. Interestingly, LNC-p722 induces a significant decrease of melanoma cell viability. In vivo data shows a significant improvement in the survival rate and a slower tumor growth with p722-loaded LNC in comparison with anti-CTLA4 mAb. Western blots confirm that LNC-p722 potentiates intrinsic apoptotic pathway. Treatment with LNC-p722 significantly activates CD8+ T lymphocytes compared to treatment with anti-CTLA4 mAb. This study uncovers a new therapeutic strategy with encapsulated p722 to prevent B16F10 melanoma growth and to improve survival of treated mice.
    Tags: apoptosis, CD8 T lymphocytes, CHEMBIO, Ferrocifen, metastatic melanoma, POLE 3.
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  • A. Vessières, Y. Wang, M. J. McGlinchey, and G. Jaouen, “Multifaceted chemical behaviour of metallocene (M = Fe, Os) quinone methides. Their contribution to biology”, Coordination Chemistry Reviews, vol. 430, p. 213658, Oct. 2021.


  • W. Wang, C. Przybylski, X. Cai, C. Lopin-Bon, R. Jiao, L. Shi, K. Sugahara, J. L. Neira, R. Daniel, and F. Li, “Investigation of action pattern of a novel chondroitin sulfate/dermatan sulfate 4- <i>O</i> -endosulfatase”, Biochemical Journal, vol. 478, no. 2, p. 281-298, Jan. 2021.
    Abstract: Recently, a novel CS/DS 4-O-endosulfatase was identified from a marine bacterium and its catalytic mechanism was investigated further (Wang, W., et. al (2015) J. Biol. Chem.290, 7823–7832; Wang, S., et. al (2019) Front. Microbiol.10, 1309). In the study herein, we provide new insight about the structural characteristics of the substrate which determine the activity of this enzyme. The substrate specificities of the 4-O-endosulfatase were probed by using libraries of structure-defined CS/DS oligosaccharides issued from synthetic and enzymatic sources. We found that this 4-O-endosulfatase effectively remove the 4-O-sulfate of disaccharide sequences GlcUAβ1-3GalNAc(4S) or GlcUAβ1-3GalNAc(4S,6S) in all tested hexasaccharides. The sulfated GalNac residue is resistant to the enzyme when adjacent uronic residues are sulfated as shown by the lack of enzymatic desulfation of GlcUAβ1-3GalNAc(4S) connected to a disaccharide GlcUA(2S)β1-3GalNAc(6S) in an octasaccharide. The 3-O-sulfation of GlcUA was also shown to hinder the action of this enzyme. The 4-O-endosulfatase exhibited an oriented action from the reducing to the non-reducing whatever the saturation or not of the non-reducing end. Finally, the activity of the 4-O-endosulfatase decreases with the increase in substrate size. With the deeper understanding of this novel 4-O-endosulfatase, such chondroitin sulfate (CS)/dermatan sulfate (DS) sulfatase is a useful tool for exploring the structure–function relationship of CS/DS.
    Tags: CSOB, POLE 3.
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  • N. V. Yerra, B. Dyaga, S. B. Dadinaboyina, S. Pandeti, J. R. Vaidya, J. - C. Tabet, and J. R. Thota, “2-Cyano-3-(2-thienyl)acrylic Acid as a New MALDI Matrix for the Analysis of a Broad Spectrum of Analytes”, Journal of the American Society for Mass Spectrometry, vol. 32, no. 1, p. 387-393, Jan. 2021.


  • L. Zhang, M. - A. Arrio, S. Mazerat, L. Catala, W. Li, E. Otero, P. Ohresser, L. Lisnard, C. Cartier dit Moulin, T. Mallah, and P. Sainctavit, “Magnetic Hysteresis in a Monolayer of Oriented 6 nm CsNiCr Prussian Blue Analogue Nanocrystals”, Inorganic Chemistry, vol. 60, no. 21, p. 16388-16396, Nov. 2021.
    Abstract: Prussian blue analogue nanocrystals of the CsINiII[CrIII(CN)6] cubic network with 6 nm size were assembled as a single monolayer on highly organized pyrolytic graphite (HOPG). X-ray magnetic circular dichroism (XMCD) studies, at the Ni and Cr L2,3 edges, reveal the presence of an easy plane of magnetization evidenced by an opening of the magnetic hysteresis loop (coercive field of ≈200 Oe) when the magnetic field, B, is at 60° relative to the normal to the substrate. The angular dependence of the X-ray natural linear dichroism (XNLD) reveals both an orientation of the nanocrystals on the substrate and an anisotropy of the electronic cloud of the NiII and CrIII coordination sphere species belonging to the nanocrystals’ surface. Ligand field multiplet (LFM) calculations that reproduce the experimental data are consistent with an elongated tetragonal distortion of surface NiII coordination sphere responsible for the magnetic behavior of monolayer.
    Tags: ERMMES, POLE 2.
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  • C. Zheng, M. Terreni, M. Sollogoub, and Y. Zhang, “Functional Role of Glycosphingolipids in Cancer”, Current Medicinal Chemistry, vol. 28, no. 20, p. 3913-3924, Jul. 2021.
    Abstract: Glycosphingolipids (GSLs) are ubiquitous components on animal cell membranes, and exposed on the outer surface. Various studies have demonstrated that they play key roles in cell proliferation, adhesion, motility and differentiation. Usually, the specific types of GSLs are expressed more highly in tumors than in normal tissues, which are known as tumorassociated antigens. It has been revealed that most tumor cells show altered GSLs patterns on their surface, abnormal GSLs signaling and biosynthesis, which together play a major role in tumor development. Tumor-associated GSL antigens have been used in the development of antitumor vaccines. There is no doubt that GSLs play a crucial role in tumor progression and would be a promising target for cancer treatment.
    Tags: GOBS, POLE 3.
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  • S. Zhu, Y. Jagadeesh, A. T. Tran, S. Imaeda, A. Boraston, D. S. Alonzi, A. Poveda, Y. Zhang, J. Désiré, J. Charollais‐Thoenig, S. Demotz, A. Kato, T. D. Butters, J. Jiménez‐Barbero, M. Sollogoub, and Y. Blériot, “Iminosugar <i>C</i> ‐Glycosides Work as Pharmacological Chaperones of NAGLU, a Glycosidase Involved in MPS IIIB Rare Disease**”, Chemistry – A European Journal, vol. 27, no. 44, p. 11291-11297, Aug. 2021.


  • X. Zhu, C. Hessin, A. Salamé, L. Sosa‐Vargas, D. Kreher, C. Adachi, A. Proust, P. Mialane, J. Marrot, A. Bouchet, M. Sliwa, S. Méry, B. Heinrich, F. Mathevet, and G. Izzet, “Photoactive Organic/Inorganic Hybrid Materials with Nanosegregated Donor–Acceptor Arrays”, Angewandte Chemie International Edition, vol. 60, no. 15, p. 8419-8424, Apr. 2021.

2020



  • Abdmouleh, Fatma, El Arbi, Mehdi, Hajer, Ben Saad, Jellali, Karim, Etata, Emna, Amara, Ibtissem Ben, Pigeon, Pascal, Hanen, Ben Hassen, Top, Siden, Jaouen, Gérard, Hammami, Riadh, Mamdouh, Ben Ali, and Gupta, Girish Kumar, “Antimicrobial, Antitumor and Side Effects Assessment of a Newly Synthesized Tamoxifen Analog”, Current Topics in Medicinal Chemistry, vol. 20, no. 25, p. 2281-2288, Sep. 2020.
    Abstract: Background: Tamoxifen citrate is a very prevalent drug marketed under several trade names like Apo-Tamox, Nolvadex, Tamec, Tamizam, and Tamoplex. This molecule is approved by the FDA for breast cancer treatment. Some studies have shown that tamoxifen has anti-tuberculosis and antiparasitic activities. Like any drug, tamoxifen possesses side effects, more or less dangerous. Aims: Basically, this work is a comparative study that aims to: primarily compare the antimicrobial and antitumor activities of tamoxifen and a newly synthesized tamoxifen analog; and to determine the molecule with lesser side effects. Methods: Three groups of mice were injected with tamoxifen citrate and compound 2(1,1-bis[4-(3- dimethylaminopropoxy)phenyl]-2-phenyl-but-1-ene dihydrochloride) at doses corresponding to C1 (1/10), C2 (1/50), and C3 (1/100) to compound 2 lethal dose (LD50 = 75 mg/kg) administered to adult mice. A group of noninjected mice served as a study control. Results: Experimental results suggest that compound 2 has b

    etter antitumor and antimicrobial activity than tamoxifen citrate besides its lower toxicity effects. Conclusion: The results obtained from the present study confirmed the antitumor and antimicrobial effect of tamoxifen citrate and its hematological side effects. Compound 2 seems to be more effective than tamoxifen citrate for antitumor and antimicrobial treatment while having less hematological side effects and less disruption of the blood biochemical parameters. These findings encourage us to perform further studies on compound 2 and test it for other therapeutic uses for which tamoxifen was found effective.
    Tags: CHEMBIO, POLE 3.
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  • L. Bedoin, S. Alves, and J. - F. Lambert, “Origins of Life and Molecular Information: Selectivity in Mineral Surface-Induced Prebiotic Amino Acid Polymerization”, ACS Earth and Space Chemistry, vol. 4, no. 10, p. 1802–1812, Sep. 2020.


  • A. Beghennou, K. Passador, A. Passador, V. Corcé, S. Thorimbert, and C. Botuha, “Synthetic Strategy Studies for a Concise Access to Functionalized Pyrano[4,3-b]pyridin-7-ones: An Entry to Semi-Rigid Analogs of Antihistamines”, European Journal of Organic Chemistry, vol. 2020, no. 36, p. 5880-5889, Sep. 2020.
    Abstract: We report short and efficient syntheses of polyfunctionalized 5,8-dihydro-7H-pyrano[4,3-b]pyridin-7-ones and 1,4-dihydro-3H-pyrano[4,3-c]pyridin-3-ones which can be considered as new aza analogs of 3-isochromanones and as promising scaffolds for medicinal chemistry. Depending on the nature of the substituent, three different and complementary synthetic methodologies were used allowing the introduction of significant diversity in the substituent on the lactone ring of the pyranopyridinones. The selective α-arylation of nitrile (SNAr) and tert-butyl ester enolate (Pd catalyzed) followed by an acidic mediated lactonisation gives access to original C8-functionalized pyrano[4,3-b]pyridin-7-ones and a seleno-mediated cyclization to C1-functionalized pyrano[4,3-c]pyridin-3-ones. We have also applied the outlined synthetic methodologies to the preparation of potential semi-rigid analogs of antihistamines.
    Tags: Antihistamines, CHEMBIO, Pinner reaction, POLE 3, Pyridopyridinones, Seleno-mediated cyclization, δ-Lactone.
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  • A. Benchohra, C. Méthivier, J. Landoulsi, D. Kreher, and R. Lescouëzec, “Electrospray ionization: an efficient approach to deposit polymetallic molecular switches onto gold surfaces”, Chemical Communications, vol. 56, no. 48, p. 6587-6589, 2020.
    Abstract: Electrospray ionization (EI) deposition is proven efficient in obtaining monolayers of a polymetallic charge transfer complex on gold surfaces. , Electrospray ionization (EI) deposition is proven efficient in obtaining monolayers of a polymetallic charge transfer complex on gold surfaces. The molecule's integrity is monitored by using PM-IRRAS and XPS. This approach broadens the perspective of molecular magnetic switch deposition, which is currently dominated by the thermal evaporation of monometallic spin crossover (SCO) complexes.
    Tags: ERMMES, POLE 2, POLYMERES.
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  • A. Cartier, E. Levernier, A. - L. Dhimane, T. Fukuyama, C. Ollivier, I. Ryu, and L. Fensterbank, “Synthesis of Aliphatic Amides through a Photoredox Catalyzed Radical Carbonylation Involving Organosilicates as Alkyl Radical Precursors”, Advanced Synthesis & Catalysis, vol. 362, no. 11, p. 2254-2259, 2020.
    Abstract: Alkyl radicals, from primary to tertiary, formed by photocatalyzed oxidation of organosilicates, are involved efficiently in radical carbonylation with carbon monoxide (CO), in the presence of various amines and CCl4, leading to a variety of amides in moderate to good yields.
    Tags: Carbonylation, MACO, multi-component reaction, photooxidative catalysis, POLE 1, radical/polar, silicates.
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  • H. Cazier, C. Malgorn, N. Fresneau, D. Georgin, A. Sallustrau, C. Chollet, J. - C. Tabet, S. Campidelli, M. Pinault, M. Mayne, F. Taran, V. Dive, C. Junot, F. Fenaille, and B. Colsch, “Development of a Mass Spectrometry Imaging Method for Detecting and Mapping Graphene Oxide Nanoparticles in Rodent Tissues”, Journal of the American Society for Mass Spectrometry, vol. 31, no. 5, p. 1025-1036, May 2020.


  • R. B. Cole, P. Bayat, J. S. Murray, C. Albers, and D. Brombach, ““Conformation pinning” by anion attachment enabling separation of isomeric steroid monomers by ion mobility spectrometry”, Journal of Mass Spectrometry, vol. 55, p. 12:e4657, Dec. 2020.


  • F. Coumes, M. Balarezo, J. Rieger, and F. Stoffelbach, “Biobased Amphiphilic Block Copolymers by RAFT-Mediated PISA in Green Solvent”, Macromolecular Rapid Communications, vol. 41, no. 9, p. 2000002, 2020.
    Abstract: Biobased amphiphilic diblock copolymers are prepared thanks to the combination of reversible addition–fragmentation transfer (RAFT) polymerization and polymerization-induced self-assembly (PISA) in an eco-friendly solvent mixture. First, the formation of a poly(acrylic acid) macroRAFT agent (PAA-TTC) is performed in water at 70 °C. Then, in a series of experiments, the PAA-TTC macroRAFT agent is used directly, without purification, as both chain transfer agent and stabilizing agent in the RAFT-PISA of menthyl acrylate (MnA) in dispersion in an ethanol/water mixture. The polymerizations of MnA are fast with high final conversions and well-controlled amphiphilic diblock copolymers are synthesized. Stable, sub-micrometric spherical particles composed of the diblock copolymers are formed. The influence of the monomer concentration and the length of the solvophobic block on the diameter of the self-assemblies is studied by means of dynamic light scattering and cryogenic transmission electron-microscopy.
    Tags: amphiphilic copolymers, biobased monomers, dispersion polymerization, PISA, POLE 4, POLYMERES, RAFT.
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  • L. Cunningham, Y. Wang, C. Nottingham, J. Pagsulingan, G. Jaouen, M. McGlinchey, and P. J. Guiry, “Enantioselective Synthesis of Planar Chiral Ferrocifens that Show Chiral Discrimination in Antiproliferative Activity on Breast Cancer Cells”, ChemBioChem, vol. 21, no. 20, p. 2974-2981, May 2020.
    Abstract: The design and first enantioselective synthesis of a series of chiral ferrocifens and ferrociphenols was realised via enantioselective palladium-catalysed intramolecular direct C?H bond activation followed by McMurry coupling. Biological evaluation revealed moderate anticancer activities on breast cancer cells and evidence of chiral discrimination between enantiomers. Treatment of these novel ferrocifens with Ag 2 O revealed that these systems are unable to form a neutral quinone methide, yet still demonstrate marked antiproliferative properties versus both the hormone-dependent MCF-7 and hormone-independent MDA-MB-231 cell lines. This bioactivity arises from two mechanisms: Fenton-type chemistry and the anti-estrogenic activity associated with the tamoxifen-like structure.
    Tags: anti-cancer activity, asymmetric synthesis, CHEMBIO, Ferrocene, McMurry coupling, POLE 3.
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  • F. D'Agosto, J. Rieger, and M. Lansalot, “RAFT-Mediated Polymerization-Induced Self-Assembly”, Angewandte Chemie International Edition, vol. 59, no. 22, p. 8368-8392, 2020.
    Abstract: After a brief history that positions polymerization-induced self-assembly (PISA) in the field of polymer chemistry, this Review will cover the fundamentals of the PISA mechanism. Furthermore, this Review will also give an overview of some of the features and limitations of RAFT-mediated PISA in terms of the choice of the components involved, the nature of the nanoobjects that can be obtained and how the syntheses can be controlled, as well as some potential applications.
    Tags: block copolymers, heterogeneous polymerization, morphology, PISA, POLE 4, POLYMERES, RAFT.
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  • G. Delecourt, L. Plet, V. Bennevault, and P. Guégan, “Synthesis of Double Hydrophilic Block Copolymers Poly(2-oxazoline-b-ethylenimine) in a Two-Step Procedure”, ACS Applied Polymer Materials, vol. 2, no. 7, p. 2696-2705, Jul. 2020.
    Abstract: The synthesis of double hydrophilic block copolymers (DHBCs) containing a polyethylenimine (PEI) and a poly(2-alkyl-2-oxazoline) in two steps was investigated in this study. First, well-defined copolymers of poly(2-methyl-2-oxazoline)-b-poly(2-ethyl-2-oxazoline) (PMeOx-b-PEtOx) and poly(2-isopropyl-2-oxazoline)-b-poly(2-methyl-2-oxazoline) (PiPrOx-b-PMeOx) were synthesized. Then, their thermoresponsive properties were analyzed to obtain a selective hydrolysis of the PMeOx block. Concerning the PMeOx-b-PEtOx copolymers, no phase transiton was witnessed, and a selectivity appeared but was quite low regardless of the copolymer composition tested, while for the PiPrOx-b-PMeOx copolymers, a complete selective hydrolysis was achieved, allowing the synthesis of PiPrOx-b-PEI DHBCs due to micelles formations in the reactive media at high temperature. Thus, for different PiPrOx-b-PMeOx with varying composition, a MeOx unit hydrolysis degree higher than 90% was obtained with nearly no hydrolysis of the PiPrOx block, providing block copolymers suitable for gene transfer experiments. The reproducibility of the reaction was also demonstrated.
    Tags: POLE 4, POLYMERES.
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  • A. Delvaux, E. Rathahao‐Paris, and 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, vol. 34, p. 24:e8928, Aug. 2020.


  • H. Dossmann, D. Gatineau, H. Clavier, A. Memboeuf, D. Lesage, and Y. Gimbert, “Exploring Phosphine Electronic Effects on Molybdenum Complexes: A Combined Photoelectron Spectroscopy and Energy Decomposition Analysis Study”, The Journal of Physical Chemistry A, vol. 124, no. 42, p. 8753-8765, Oct. 2020.


  • R. El-Hnayn, L. Canabady-Rochelle, C. Desmarets, L. Balan, H. Rinnert, O. Joubert, G. Medjahdi, H. Ben Ouada, and R. Schneider, “One-Step Synthesis of Diamine-Functionalized Graphene Quantum Dots from Graphene Oxide and Their Chelating and Antioxidant Activities”, Nanomaterials, vol. 10, no. 1, p. 104, Jan. 2020.
    Abstract: 2,2&rsquo;-(Ethylenedioxy)bis(ethylamine)-functionalized graphene quantum dots (GQDs) were prepared under mild conditions from graphene oxide (GO) via oxidative fragmentation. The as-prepared GQDs have an average diameter of ca. 4 nm, possess good colloidal stability, and emit strong green-yellow light with a photoluminescence (PL) quantum yield of 22% upon excitation at 375 nm. We also demonstrated that the GQDs exhibit high photostability and the PL intensity is poorly affected while tuning the pH from 1 to 8. Finally, GQDs can be used to chelate Fe(II) and Cu(II) cations, scavenge radicals, and reduce Fe(III) into Fe(II). These chelating and reducing properties that associate to the low cytotoxicity of GQDs show that these nanoparticles are of high interest as antioxidants for health applications.
    Tags: 2, 2’-(ethylenedioxy)bis(ethylamine), ARC, graphene quantum dots, optical properties, POLE 1, redox-active nanoparticles.
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  • Y. T. L. Guen, T. L. Gall, P. Midoux, P. Guégan, S. Braun, and T. Montier, “Gene transfer to skeletal muscle using hydrodynamic limb vein injection: current applications, hurdles and possible optimizations”, The Journal of Gene Medicine, vol. 22, no. 2, p. e3150, 2020.
    Abstract: Hydrodynamic limb vein injection is an in vivo locoregional gene delivery method. It consists of administrating a large volume of solution containing nucleic acid constructs in a limb with both blood inflow and outflow temporarily blocked using a tourniquet. The fast, high pressure delivery allows the musculature of the whole limb to be reached. The skeletal muscle is a tissue of choice for a variety of gene transfer applications, including gene therapy for Duchenne muscular dystrophy or other myopathies, as well as for the production of antibodies or other proteins with broad therapeutic effects. Hydrodynamic limb vein delivery has been evaluated with success in a large range of animal models. It has also proven to be safe and well-tolerated in muscular dystrophy patients, thus supporting its translation to the clinic. However, some possible limitations may occur at different steps of the delivery process. Here, we have highlighted the interests, bottlenecks and potential improvements that could further optimize non-viral gene transfer following hydrodynamic limb vein injection.
    Tags: gene transfer, hydrodynamic delivery, locoregional, non-viral gene delivery, optimizations, POLE 4, POLYMERES, skeletal muscle.
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  • D. Jamroz, N. Fischer-Durand, M. Palusiak, S. Wojtulewski, S. Jarzyński, M. Stępniewska, M. Salmain, and B. Rudolf, “Inverse electron-demand Diels-Alder (iEDDA) bioorthogonal conjugation of half-sandwich transition metallocarbonyl entities to a model protein”, Applied Organometallic Chemistry, vol. 34, no. 4, p. e5507, Apr. 2020.
    Abstract: Novel transition metallocarbonyl complexes carrying a norbornene or an oxanorbornene group were synthesized by [4 + 2] cycloaddition between the organometallic maleimide dienophiles and cyclopentadiene or furan, respectively. The oxanorbornene adduct was obtained as a mixture of endo and exo isomers as confirmed by X-ray diffraction and NMR spectroscopy. The (oxa)norbornene groups further provided convenient chemical reporters to carry out inverse electron demand Diels-Alder (iEDDA) reactions with tetrazine derivatives. Detailed kinetic studies with a model tetrazine revealed that faster rates of reaction were determined with both isomers of the oxanorbornene complex with respect to the norbornene complexes. Eventually, incorporation of metallocarbonyl entities into bovine serum albumin equipped with tetrazine handles was achieved as shown by IR spectroscopy of the protein conjugates.
    Tags: bioconjugation, CHEMBIO, iEDDA, metallocarbonyl complex, norbornene, POLE 3, tetrazine.
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  • J. ‐R. Jiménez, J. Glatz, A. Benchohra, G. Gontard, L. ‐M. Chamoreau, J. ‐F. Meunier, A. Bousseksou, and R. Lescouëzec, “Electron Transfer in the Cs⊂{Mn <sub>4</sub> Fe <sub>4</sub> } Cubic Switch: A Soluble Molecular Model of the MnFe Prussian‐Blue Analogues”, Angewandte Chemie International Edition, vol. 59, no. 21, p. 8089-8093, May 2020.


  • A. Li, Y. Li, L. - M. Chamoreau, C. Desmarets, L. Lisnard, and Y. Journaux, “A Bis-Polydentate Oxamate-Based Achiral Ligand That Can Stabilize a Macrocyclic Mixed Valence Compound or Induce a 1D Helical Chain”, European Journal of Inorganic Chemistry, vol. 2020, no. 34, p. 3311-3319, 2020.
    Abstract: The reaction of the N-(2-hydroxyphenyl)oxamate ligand (ohpma) has been investigated with cobalt(II) and copper(II) ions. It has led to two coordination compounds, (TMA)3[CoIII(ohpma)2CoII(MeOH)23]·10H2O·5MeOH (1) and (HNEt3)[Cu(ohpma)] (2). Both compounds have been characterized by single-crystal X-ray diffraction and magnetometry. The X-ray diffraction studies have revealed atypical structures that are not commonly observed in oxamate coordination chemistry with a macrocyclic arrangement for the mixed-valence cobalt-based complex 1, and a helical chiral chain for compound 2. In the latter, the bis-polydentate nature of the (ohpma)3– ligand with distinct tridentate and bidentate coordination sites creates a chirogenic center on the copper ion. The investigation of the magnetic properties shows for complex 1 a single-molecule magnet behavior detectable under static field, while antiferromagnetic interactions dominate the behavior of 2.
    Tags: ARC, ERMMES, POLE 1, POLE 2.
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  • Z. Li, T. Bavaro, S. Tengattini, R. Bernardini, M. Mattei, F. Annunziata, R. B. Cole, C. Zheng, M. Sollogoub, L. Tamborini, M. Terreni, and Y. Zhang, “Chemoenzymatic synthesis of arabinomannan (AM) glycoconjugates as potential vaccines for tuberculosis”, European Journal of Medicinal Chemistry, vol. 204, p. 112578, 2020.


  • Y. Liu, J. Oble, A. Pradal, and G. Poli, “Catalytic Domino Annulations through η3-Allylpalladium Chemistry: A Never-Ending Story”, European Journal of Inorganic Chemistry, vol. 2020, no. 11-12, p. 942-961, 2020.
    Abstract: Annulative η3-allylpalladium chemistry has been a longstanding trending research topic since the 80's. Nowadays, this research area is still providing challenges to the catalysis community leading to the development original and brand-new transformations. Several reaction partners have been used as precursors for η3-allylpalladium species, namely allyl diacetates, allyl monoacetates, 3-acetoxy-2-trimethylsilylmethyl-1-propene (ASMP), alkylidene cyclopropanes (ACPs), vinyl cyclopropanes (VCPs), vinyl aziridines, and vinyl epoxides. This minireview is intended to show the recent developments in the field of annulative η3-allylpalladium chemistry with emphasis on new reactivity, enantioselective transformations as well as potential applications in total synthesis.
    Tags: POLE 1, ROCS.
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  • S. Nasri, M. Hajji, M. Guergueb, S. Dhifaoui, V. Marvaud, F. Loiseau, F. Molton, T. Roisnel, T. Guerfel, and H. Nasri, “Spectroscopic, Electrochemical, Magnetic and Structural Characterization of an Hexamethylenetetramine Co(II) Porphyrin Complex – Application in the Catalytic Degradation of Vat Yellow 1 dye”, Journal of Molecular Structure, p. 129676, Nov. 2020.
    Abstract: In this study, a new cobaltous-(hexamethylenetetramine) [meso-tetra(para-methoxyphenyl)porphyrin complex with the formula [CoII(TMPP)(HMTA)] (I) was synthesized. The molecular structure was confirmed in solution by 1H NMR spectroscopy and mass spectrometry methods, and the single crystal X-ray diffraction structure of (I) was determined at both room temperature and low temperature. This species was further characterized by infrared, UV-visible and fluorescence spectroscopies, magnetic susceptibility measurements and cyclic voltammetry. The chemical reactivity behavior was also assessed theoretically through Density Functional Theory (DFT) approach. Magnetic investigation indicates that the Co(II)-HMTA porphyrin (I) species at low temperature is a cobaltous low-spin (S = 1/2) species while at high temperature complex (I) exhibits a spin-crossover low-spin (S = 1/2) ↔ high-spin (S = 3/2). The adsorption kinetic of the “vat yellow 1 dye” was carried out in aqueous solution at pH = 6. The experimental results are better fitted using the pseudo second order model. Furthermore, complex (I) was tested as catalyst in the degradation of the vat yellow 1 dye using an aqueous H2O2 solution and by photodegradation under solar light.
    Tags: E-POM, POLE 2.
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  • Š. Nováková Lachmanová, L. Pospíšil, J. Šebera, B. Talbi, M. Salmain, and M. Hromadová, “Electrochemical characterization of the artificial metalloenzyme papain-[(η6-arene)Ru(1,10-phenanthroline)Cl]+”, Journal of Electroanalytical Chemistry, vol. 859, p. 113882, Feb. 2020.
    Abstract: Electrochemical properties were studied for [(η6-arene)Ru(1,10-phenanthroline)Cl]Cl (arene = C6H5(CH2)2NHCOCH2Cl) organometallic complex 1, protein Papain PAP and its conjugate with organometallic complex 1-PAP. The latter can serve as an artificial metalloenzyme with catalytic activity in transfer hydrogenation. This work demonstrates that AC voltammetry and electrochemical impedance spectroscopy can be used as fast tools to screen the catalytic ability of 1-PAP electrochemically by studies of the catalytic hydrogen evolution reaction (HER). Proteins are known to catalyze this process, but we have shown that additional HER signal associated with the catalytic activity of 1 is observed for its conjugate with Papain 1-PAP.
    Tags: Artificial metalloenzyme, CHEMBIO, Electrochemical admittance and impedance techniques, Papain, POLE 3, Ruthenium(II) complexes.
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  • V. Puchelle, Y. Latreyte, M. Girardot, L. Garnotel, L. Levesque, O. Coutelier, M. Destarac, P. Guégan, and N. Illy, “Functional Poly(ester-alt-sulfide)s Synthesized by Organo-Catalyzed Anionic Ring-Opening Alternating Copolymerization of Oxiranes and γ-Thiobutyrolactones”, Macromolecules, vol. 53, no. 13, p. 5188-5198, Jul. 2020.
    Abstract: The copolymerization of tert-butyl glycidyl ether (tBuGE), allyl glycidyl ether (AGE), ethoxyethyl glycidyl ether (EEGE) and 1,2-epoxybutane (BO) with γ-thiobutyrolactone was investigated using benzyl alcohol–phosphazene bases as initiating systems. The prepared copolymers display perfect (poly(ester-alt-sulfide)) alternating structures for all epoxide monomers as evidenced by 1H, 13C, and 2D NMR and MALDI–TOF mass spectrometry. A marked influence of the reaction temperature on the occurrence of transesterification side reactions has been evidenced. In particular, at elevated temperature, transesterification reactions led to the formation of alternating macrocycles. The choice of the phosphazene base (tBuP4, tBuP2, or tBuP1) has a strong impact on the system reactivity and on the control of the polymerization. The use of tBuP1 led to very slow polymerization rates. The polymerization is much faster in the presence of tBuP2 even at low temperature. The use of tBuP4 shows an intermediate polymerization rate and enabled a good polymerization control at moderate temperatures. Finally, the synthesis of well-defined polyether-block-poly(ester-alt-sulfide) and the polymerization of a challenging substituted γ-thiolactone were proven to be feasible.
    Tags: POLYMERES.
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  • J. P. Rada, J. Forté, G. Gontard, V. Corcé, M. Salmain, and N. A. Rey, “Isoxazole-Derived Aroylhydrazones and Their Dinuclear Copper(II) Complexes Show Antiproliferative Activity on Breast Cancer Cells with a Potentially Alternative Mechanism Of Action”, ChemBioChem, vol. 21, no. 17, p. 2474-2486, Apr. 2020.
    Abstract: Abstract This paper reports the design, synthesis and cytotoxicity studies of two new isoxazole-derived aroylhydrazone ligands and their dinuclear copper(II) complexes. Compounds were fully characterized by various spectroscopic and analytical techniques. The molecular structures of four derivatives were confirmed by X-ray crystallography. The stability of the ligands and the complexes in aqueous medium was monitored spectroscopically. Both the ligands and the complexes were shown to interact with calf thymus DNA (ct-DNA). Additionally, structures containing a phenol pendant arm were significantly more cytotoxic than those carrying a pendant pyridine substituent, reaching sub-micromolar IC50 values on the triple-negative human breast cancer cell line MDA-MB-231. The metal chelation and transchelation ability of the compounds towards FeII, FeIII and ZnII ions was explored as a possible mechanism of action of these compounds.
    Tags: antitumor agents, aroylhydrazonic ligands, CHEMBIO, copper(II) complexes, cytotoxicity, DNA, POLE 3.
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  • R. Ramos, J. M. Zimbron, S. Thorimbert, L. - M. Chamoreau, A. Munier, C. Botuha, A. Karaiskou, M. Salmain, and J. Sobczak-Thépot, “Insights into the antiproliferative mechanism of (C^N)-chelated half-sandwich iridium complexes”, Dalton Transactions, vol. 49, no. 48, p. 17635-17641, Nov. 2020.
    Abstract: Transition metal-based anticancer compounds, as alternative to platinum derivatives, are raising scientific interest as they may present distinct although poorly understood mechanisms of action. We used a structure-activity relationship-based methodology to investigate the chemical and biological features of a series of ten (C^N)-chelated half-sandwich iridiumIII complexes of the general formula [IrCp*(phox)Cl], where (phox) is a 2-phenyloxazoline ligand forming a 5-membered metallacycle. This series of compounds undergoes a fast exchange of their chlorido ligand once solubilised in DMSO. They were cytotoxic to HeLa cells with IC50 values in the micromolar range and induced a rapid activation of caspase-3, an apoptosis marker. In vitro, the oxidative power of all the complexes towards NADH was highlighted but only the complexes bearing substituents on the oxazoline ring were able to produce H2O2 at the micromolar range. However, we demonstrated using a powerful HyPer protein redox sensor-based flow cytometry assay that most complexes rapidly raised intracellular levels of H2O2. Hence, this study shows that oxidative stress can partly explain the cytotoxicity of these complexes on the HeLa cell line and gives a first entry to their mechanism of action
    Tags: CHEMBIO, POLE 3.
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  • Y. Ren, J. Forte, K. Cheaib, N. Vanthuyne, L. Fensterbank, H. Vezin, M. Orio, S. Blanchard, and M. Desage-El Murr, “Optimizing Group Transfer Catalysis by Copper Complex with Redox-Active Ligand in an Entatic State”, Iscience, vol. 23, no. 3, p. UNSP 100955, Mar. 2020.
    Abstract: Metalloenzymes use earth-abundant non-noble metals to perform high-fidelity transformations in the biological world. To ensure chemical efficiency, metalloenzymes have acquired evolutionary reactivity-enhancing tools. Among these, the entatic state model states that a strongly distorted geometry induced by ligands around a metal center gives rise to an energized structure called entatic state, strongly improving the reactivity. However, the original definition refers both to the transfer of electrons or chemical groups, whereas the chemical application of this concept in synthetic systems has mostly focused on electron transfer, therefore eluding chemical transformations. Here we report that a highly strained redox-active ligand enables a copper complex to perform catalytic nitrogen- and carbon-group transfer in as fast as 2 min, thus exhibiting a strong increase in reactivity compared with its unstrained analogue. This report combines two reactivity-enhancing features from metalloenzymes, entasis and redox cofactors, applied to group-transfer catalysis.
    Tags: aziridination, cu, E-POM, galactose-oxidase, generation, MACO, metal-complexes, models, oxidation, POLE 1, POLE 2, radicals, reactivity, site.
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  • P. - J. Roumanet, N. Jarroux, L. Goujard, J. Le Petit, Y. Raoul, V. Bennevault, and P. Guégan, “Synthesis of Linear Polyesters from Monomers Based on 1,18-(Z)-Octadec-9-enedioic Acid and Their Biodegradability”, ACS Sustainable Chemistry & Engineering, vol. 8, no. 45, p. 16853-16860, Nov. 2020.
    Abstract: A new family of bio-based linear polyesters from oleic acid was developed by a bulk polymerization process. First, efficient chemical pathways were selected to synthesize three monomer derivatives fro

    m 1,18-(Z)-octadec-9-enedioic acid, allowing the synthesis of four polyesters that differ by the number of double bonds along the polymer backbone. After the analysis of the structure of the polymers, their thermal properties and their biodegradability were investigated. It was shown that the melting temperature of the polyesters increased with the decrease in the unsaturation content in the repeat units of the polymers and they have very low glass-transition temperatures. A biodegradation process was also highlighted for poly(1,18-(Z)-octadec-9-enylene 1,18-(Z)-octadec-9-enedioate) and poly(1,18-octadecylene 1,18-octadecanedioate). Based on their thermal features, these biodegradable polyesters can represent an alternative of the synthetic polymers derived from petroleum hydrocarbons, such as low-density polyethylene.
    Tags: POLYMERES.
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  • A. Serafino, D. Balestri, L. Marchiò, M. Malacria, E. Derat, and G. Maestri, “Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light”, Organic Letters, vol. 22, no. 16, p. 6354-6359, Aug. 2020.
    Abstract: Enallenes can be readily converted into two families of 3.2.0 (hetero)bicycles with high diastereoselectivities through the combination of visible light with a suitable Ir(III) complex (1 mol %). Two complementary pathways, namely, a photocycloaddition versus a radical chain, can then take place. Both manifolds grant complete regiocontrol of the allene difunctionalization. This is accompanied by an original 1,3-group shift using sulfonyl allenamides that deliver a congested tetrasubstituted headbridging carbon in the corresponding product.
    Tags: MACO, POLE 1.
    Attachment ACS Full Text Snapshot
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  • K. Wu, B. Pudasaini, J. Y. Park, S. Top, G. Jaouen, M. - H. Baik, and W. E. Geiger, “Oxidation of Cymantrene-Tagged Tamoxifen Analogues: Effect of Diphenyl Functionalization on the Redox Mechanism”, Organometallics, vol. 39, no. 5, p. 679–687, Feb. 2020.
    Abstract: The oxidations of 1,1′-di-p-anisolyl-2-cymantrenylbutene (3b) and 1,1′-di-p-hydroxyphenyl-2-cymantrenylbutene (3c) were investigated by electrochemical and spectroscopic experiments and by density functional theory (DFT) calculations. Both compounds undergo a reversible one-electron oxidation followed closely by a partially chemically reversible second oxidation (E1/2 values vs ferrocene: 0.60 and 0.74 V for 3b; 0.63 and 0.78 V for 3c). In comparison to the nonphenyl-functionalized parent, 1,1′-diphenyl-2-cymantrenylbutene (3a), 3b,c have lower and more closely spaced oxidation potentials and more rapid follow-up reactions of their dications, 3b2+ and 3c2+. Shifts in the calculated charge distributions of the neutral compounds and their singly and doubly oxidized products corroborated trends in the measured shifts of Mn–CO νCO frequencies in assigning the redox sites primarily to the diarylbutene fragment. Upon removal of electrons, the lost charge density is partially compensated by the polarizable cymantrenyl tag. The half-lives of the dications 3b2+ and 3c2+ are about 10 s at room temperature in dichloromethane/0.05 M [NBu4][B(C6F5)4]. Their follow-up reactions are initiated by loss of a proton either from a hydroxyl group or from the CH2 group of the diarylbutene unit, giving rise to two products having quinone methide structures. Although the initial oxidation sites of cymantrene-tagged diarylbutenes are primarily ligand based and those of ferrocene-tagged diarylbutenes are metal-based, the ultimate oxidation products of their p-OH- or p-OMe-functionalized derivatives are very similar.
    Tags: CHEMBIO, POLE 3.
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2019



  • V. Ayzac, Q. Sallembien, M. Raynal, B. Isare, J. Jestin, and L. Bouteiller, “A Competing Hydrogen Bonding Pattern to Yield a Thermo-Thickening Supramolecular Polymer”, Angewandte Chemie International Edition, vol. 58, no. 39, p. 13849-13853, 2019.
    Abstract: Introduction of competing interactions in the design of a supramolecular polymer (SP) creates pathway complexity. Ester–bis-ureas contain both a strong bis-urea sticker that is responsible for the build-up of long rod-like objects by hydrogen bonding and ester groups that can interfere with this main pattern in a subtle way. Spectroscopic (FTIR and CD), calorimetric (DSC), and scattering (SANS) techniques show that such ester–bis-ureas self-assemble into three competing rod-like SPs. The previously unreported low-temperature SP is stabilized by hydrogen bonds between the interfering ester groups and the urea moieties. It also features a weak macroscopic alignment of the rods. The other structures form isotropic dispersions of rods stabilized by the more classical urea-urea hydrogen bonding pattern. The transition from the low-temperature structure to the next occurs reversibly by heating and is accompanied by an increase in viscosity, a rare feature for solutions in hydrocarbons.
    Tags: hydrogen bonds, pathway complexity, POLYMERES, self-assembly, supramolecular polymers, urea.
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  • J. Besnardiere, B. Ma, A. Torres-Pardo, G. Wallez, H. Kabbour, J. M. González-Calbet, H. J. Von Bardeleben, B. Fleury, V. Buissette, C. Sanchez, T. Le Mercier, S. Cassaignon, and D. Portehault, “Structure and electrochromism of two-dimensional octahedral molecular sieve h’-WO3”, Nature Communications, vol. 10, no. 1, p. 327, Jan. 2019.
    Abstract: Octahedral molecular sieves (OMS) are built of transition metal-oxygen octahedra that delimit sub-nanoscale cavities. Compared to other microporous solids, OMS exhibit larger versatility in properties, provided by various redox states and magnetic behaviors of transition metals. Hence, OMS offer opportunities in electrochemical energy harnessing devices, including batteries, electrochemical capacitors and electrochromic systems, provided two conditions are met: fast exchange of ions in the micropores and stability upon exchange. Here we unveil a novel OMS hexagonal polymorph of tungsten oxide called h’-WO3, built of (WO6)6 tunnel cavities. h’-WO3 is prepared by a one-step soft chemistry aqueous route leading to the hydrogen bronze h’-H0.07WO3. Gentle heating results in h’-WO3 with framework retention. The material exhibits an unusual combination of 1-dimensional crystal structure and 2-dimensional nanostructure that enhances and fastens proton (de)insertion for stable electrochromic devices. This discovery paves the way to a new family of mixed valence functional materials with tunable behaviors.
    Tags: ERMMES, POLE 2.
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  • A. Bleuzen, V. Marvaud, and C. Train, “Forty years of exchange interactions on the occasion of the 75th birthday of Michel Verdaguer”, Comptes Rendus Chimie, vol. 22, no. 6, p. 435-436, Jun. 2019.


  • A. Casini, A. Vessières, and S. M. Meier-Menches, Metal-based Anticancer Agents, Royal Society of Chemistry. 2019.
    Abstract: Metal-based anticancer drugs are among the most successful therapeutic agents, as evidenced by the frequent prescription of selected platinum and arsenic compounds to patients. Metal-based Anticancer Agents covers the interdisciplinary world of inorganic drug discovery and development by introducing the most prominent compound classes based on different transition metals, discussing emerging concepts and enabling methods, as well as presenting key pre-clinical and clinical aspects. Recent progress on the unique features of next-generation targeted metal-based anticancer agents, including supramolecular coordination complexes used for both therapy and drug delivery, promise a bright future beyond the benefits of pure cytotoxic activity. With contributions from global leaders in the field, this book will serve as a useful reference to established researchers as well as a practical guide to those new to metallodrugs, and postgraduate students of medicinal chemistry and metallobiology.
    Tags: CHEMBIO, POLE 3.
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  • C. Cecchini, G. Cera, M. Lanzi, L. Marchiò, M. Malacria, and G. Maestri, “Diastereoselective bicyclization of enynols via gold catalysis”, Organic Chemistry Frontiers, vol. 6, no. 20, p. 3584-3588, Oct. 2019.
    Abstract: A Au(I)-catalyzed protocol for the cycloisomerizations of enynols into 4.3.0 (hetero)bicycles with complete regio- and diastereoselection is herein described. The sequential bicyclization exploits substrates with a styryl arm, disclosing in turn a reactive pathway that is complementary to the literature reports. The use of a gold(I)–phosphite catalyst allowed for the synthesis of functionalized polycycles under mild conditions, with good yields and low catalyst loadings (1 mol%).
    Tags: MACO, POLE 1.
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  • C. Cecchini, M. Lanzi, G. Cera, M. Malacria, and G. Maestri, “Complementary Reactivity of 1,6-Enynes with All-Metal Aromatic Trinuclear Complexes and Carboxylic Acids”, Synthesis, vol. 51, no. 5, p. 1216-1224, Mar. 2019.
    Abstract: The distinct reactivity of 1,6-enynes in the presence of a trinuclear metal complex activated by a carboxylic acid is presented. The triplatinum catalyst enables the cyclization of the substrate and subsequent incorporation of a nucleophile in the final product. In contrast, sequential cyclization/double bond shift occurs under analogous conditions in the presence of the corresponding tripalladium complex.
    Tags: aromaticity, clusters, cyclization, Key words enynes, MACO, palladium, platinum, POLE 1.
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