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2023



  • P. Idlas, E. Lepeltier, G. Bastiat, P. Pigeon, M. J. McGlinchey, N. Lautram, A. Vessières, G. Jaouen, et C. Passirani, « Physicochemical Characterization of Ferrocifen Lipid Nanocapsules: Customized Drug Delivery Systems Guided by the Molecular Structure », Langmuir, vol. 39, nᵒ 5, p. 1885-1896, janv. 2023.
    Résumé : Ferrocifens, lipophilic organometallic complexes, comprise a biologically active redox motif [ferrocenyl-ene-p-phenol] which confers very interesting cytotoxic properties to this family. However, because of their highly lipophilic nature, a formulation stage is required before being administered in vivo. In recent decades, ferrocifen lipid nanocapsules (LNCs) have been successfully formulated and have demonstrated anticancer activity on multidrug-resistant cancers in several mice and rat models (glioblastoma, breast cancer, and metastatic melanoma). A recent family of ferrocifens (succinimidoalkyl-ferrociphenols, including P722) appears to be most efficacious on several resistant cancer cell lines, with IC50 values in the nanomolar range together with promising in vivo results on murine ovarian cancer models. As LNCs are composed of an oily core (caprylic/capric triglycerides), modulation of the succinimido-ferrociphenol lipophilicity could be a valuable approach toward improving the drug loading in LNCs. As the drug loading of the diphenol P722 in LNCs was low, it was structurally modified to increase its lipophilicity and thereby the payload in LNCs. Chemical modification led to a series of five succinimido-ferrocifens. Results confirmed that these slight structural modifications led to increased drug loading in LNCs for all ferrocifens, with no reduction of their cytotoxicity on the SKOV3 ovarian cancer cell line. Interestingly, encapsulation of two of the ferrocifens, diester P769 and monophenolic ester (E)-P998, led to the formation of a gel. This was unprecedented behavior, a phenomenon that could be rationalized in terms of the positioning of ferrocifens in LNCs as shown by the decrease of interfacial tension measurements at the water/oil interface. Moreover, these results highlighted the importance of obtaining a gel of this particular motif, in which the acetylated phenolic ring and the succinimidoalkyl moieties are mutually cis relative to the central double bond. Promising perspectives to use these ferrocifen-loaded LNCs to treat glioblastoma could be readily envisaged by local application of the gel in the cavity after tumor resection.
    Mots-clés : CHEMBIO, POLE 3.
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  • A. Mamontov, L. Chang, H. Dossmann, B. Bertrand, L. Dechoux, et S. Thorimbert, « Iron Catalyzed Dearomatization of Pyridines into Annelated Azepine Derivatives in a One-Step, Three-Component Reaction », Organic Letters, vol. 25, nᵒ 1, p. 256-260, 2023.
    Résumé : Commercially available Fe(TTP)Cl catalyzes three-component dearomative formal cycloaddition reactions between pyridines, diazo compounds, and coumalates. Diversely substituted annelated seven-membered N-heterocycles could be generated in less than 10 min in one step at room temperature. The reaction is compatible to gram scale. The extension to benzimidazoles in place of pyridines has been successfully demonstrated. The mechanism of this reaction has been carefully examined by computational studies that corroborate the observed regioselectivities.
    Mots-clés : CHEMBIO, CSOB, POLE 3.
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  • V. Pellas, F. Sallem, J. Blanchard, A. Miche, S. M. Concheso, C. Méthivier, M. Salmain, et S. Boujday, « Silica-coated gold nanorods biofunctionalization for localized surface plasmon resonance (LSPR) biosensing », Talanta, vol. 255, p. 124245, avr. 2023.
    Résumé : We introduce here the engineering of nanobiosensors designed from gold nanorods coated with an ultrathin layer of silica (AuNR@SiO2) and biofunctionalized with antibodies for the Localized Surface Plasmon Resonance (LSPR) biosensing of proteins. Despite the outstanding properties of AuNRs, their use for LSPR biosensing is limited due to the presence of the surfactant cetyltrimethylammonium bromide (CTAB) – mandatory for their synthesis - which forms a strongly-bounded and positively-charged bilayer at their surface and significantly complicates their bio-functionalization. When coated with a thin layer of silica, these nanomaterials exhibit an improved sensitivity to refractive index change which augurs for better analytical performances. Here, we undertook an in-depth investigation of the biofunctionalization of AuNR@SiO2 via three different routes to design and test a label-free LSPR biosensor operating in solution. In the first route, we took advantage of the negatively charged external silica shell to immobilize anti-rabbit IgG antibody by electrostatic physisorption. In the second and third routes, the silica surface was reacted with thiol or aldehyde terminated silanes, subsequently utilized to covalently attach anti-rabbit IgG antibody to the surface. The resulting nanoprobes were characterized by a wide range of physical methods (TEM, XPS, DLS, ELS and UV-Visible spectroscopy) then tested for the biosensing of rabbit-IgG. The three nanobiosensors maintain an excellent colloidal stability after analyte recognition and exhibit extremely high analytical performances in terms of specificity and dynamic range, with an LoD down to 12 ng/mL.
    Mots-clés : CHEMBIO, Core−Shell, Gold nanorods, Immunosensing, LSPR, POLE 3, Silica coating, Surface chemistry.
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  • A. Vessières et M. J. McGlinchey, « Bioorganometallic chemistry – the early years », Journal of Organometallic Chemistry, vol. 987-988, p. 122623, avr. 2023.
    Résumé : Bioorganometallic chemistry is now a maturing field attracting researchers around the world, and also across the Periodic Table. It has found applications in a broad range of areas such as drug discovery, biocatalysis and imaging. We review here the first experiments carried out in the early 1980′s at the Ecole Nationale Supérieure de Chimie de Paris under the leadership of Gérard Jaouen, a key figure and visionary in the development of this theme. However, they also required important contributions from Canadian collaborators with expertise in NMR and IR spectroscopy, together with the availability of more powerful and versatile instrumentation. This collaboration found its fulfillment in the demonstration of the use of metal carbonyl complexes (exemplified by an estradiol derivative labeled by a Cr(CO)3 unit) as non-isotopic tracers allowing the detection of estradiol receptors, an essential marker for setting up a targeted therapy for breast cancer. This approach was based on the premise that the intense metal carbonyl stretching vibrations are found in a window (2100–1850 cm−1) where the protein itself does not absorb. The field was extended to the arena of non-isotopic immunoassays, including the simultaneous detection of multiple antiepileptic drugs bearing metal carbonyl labels. More recently, taking advantage of the new technique of atomic force microscopy-infrared spectroscopy (AFM-IR) it has been possible to accomplish direct tracing of these complexes in cells. The contributions of the original group of workers in the field are highlighted, and placed in the perspective of today's subsequent emphasis on the management of previously untreatable cancers.
    Mots-clés : 2D NMR, CHEMBIO, Estrogen receptor, FT-IR spectroscopy, Immunoassay, Metal carbonyls, Organometallic tracers, POLE 3.
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  • J. Yang, V. Giuso, M. - C. Hou, E. Remadna, J. Forté, H. - C. Su, C. Gourlaouen, M. Mauro, et B. Bertrand, « Biphenyl Au(III) Complexes with Phosphine Ancillary Ligands: Synthesis, Optical Properties, and Electroluminescence in Light-Emitting Electrochemical Cells », Inorganic Chemistry, mars 2023.
    Résumé : A series of ten cationic complexes of the general formula [(C^C)Au(P^P)]X, where C^C = 4,4′-di-tert-butyl-1,1′-biphenyl, P^P is a diphosphine ligand, and X is a noncoordinating counteranion, have been synthesized and fully characterized by means of chemical and X-ray structural methods. All the complexes display a remarkable switch-on of the emission properties when going from a fluid solution to a solid state. In the latter, long-lived emission with lifetime τ = 1.8–83.0 μs and maximum in the green-yellow region is achieved with moderate to high photoluminescence quantum yield (PLQY). This emission is ascribed to an excited state with a mainly triplet ligand-centered (3LC) nature. This effect strongly indicates that rigidification of the environment helps to suppress nonradiative decay, which is mainly attributed to the large molecular distortion in the excited state, as supported by density functional theory (DFT) and time-dependent DFT (TD-DFT) computation. In addition, quenching intermolecular interactions of the emitter are avoided thanks to the steric hindrance of the substituents. Emissive properties are therefore restored efficiently. The influence of both diphosphine and anion has been investigated and rationalized as well. Using two complexes as examples and owing to their enhanced optical properties in the solid state, the first proof-of-concept of the use of gold(III) complexes as electroactive materials for the fabrication of light-emitting electrochemical cell (LEC) devices is herein demonstrated. The LECs achieve peak external quantum efficiency, current efficiency, and power efficiency up to ca. 1%, 2.6 cd A–1, and 1.1 lm W–1 for complex 1PF6 and 0.9%, 2.5 cd A–1, and 0.7 lm W–1 for complex 3, showing the potential use of these novel emitters as electroactive compounds in LEC devices.
    Mots-clés : CHEMBIO, POLE 3.
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2022


  • « Boron, silicon, nitrogen and sulfur-based contemporary precursors for the generation of alkyl radicals by single electron transfer and their synthetic utilization - Chemical Society Reviews (RSC Publishing) », 2022. [Online]. Available: https://pubs.rsc.org/en/content/articlelanding/2022/cs/d1cs01084k. [Accessed: 31-janv.-2023].
    Mots-clés : CHEMBIO, MACO, POLE 1, POLE 3.
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  • V. Corcé, C. Ollivier, et L. Fensterbank, « Boron, silicon, nitrogen and sulfur-based contemporary precursors for the generation of alkyl radicals by single electron transfer and their synthetic utilization », Chemical Society Reviews, vol. 51, nᵒ 4, p. 1470-1510, févr. 2022.
    Résumé : Recent developments in the use of boron, silicon, nitrogen and sulfur derivatives in single-electron transfer reactions for the generation of alkyl radicals are described. Photoredox catalyzed, electrochemistry promoted or thermally-induced oxidative and reductive processes are discussed highlighting their synthetic scope and discussing their mechanistic pathways.
    Mots-clés : CHEMBIO, MACO, POLE 1, POLE 3.
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  • C. Fayolle, P. Pigeon, N. Fischer-Durand, M. Salmain, O. Buriez, A. Vessières, et E. Labbé, « Synthesis, Electrochemical and Fluorescence Properties of the First Fluorescent Member of the Ferrocifen Family and of Its Oxidized Derivatives », Molecules, vol. 27, nᵒ 19, p. 6690, 2022.
    Résumé : The first fluorescent ferrociphenol derivative (P797) has been synthesized via McMurry cross-coupling followed by copper-catalyzed [3 + 2] azide-alkyne cycloaddition of the fluorescent group coumarin. Cyclic voltammograms of P797 exhibit either a monoelectronic oxidation wave ascribed to the ferrocene Fe(II) → Fe(III) conversion or a three-electron oxidation process in the presence of a base, leading to a Fe(III) qui

    none methide adduct. This general sequence is consistent with those previously described for non-fluorescent ferrociphenols. Furthermore, the fluorescence properties of P797 and its oxidized intermediates appear to strongly depend on the redox state of the ferrocene group. Indeed, electrochemical generation of Fe(III) (ferrocenium) states markedly increases the fluorescence emission intensity. In contrast, the emission of the Fe(II) (ferrocene) states is partially quenched by photoinduced electron transfer (PET) from the Fe(II) donor to the coumarin acceptor and by concentration-dependent self-quenching. Owing to its switchable fluorescence properties, complex P797 could represent an innovative and useful tool to study the biodistribution and the redox state of ferrocifens in cancer cells.
    Mots-clés : CHEMBIO, coumarin, ferrocene, fluorescence switching, PET, POLE 3, redox state.
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  • P. Idlas, A. Ladaycia, F. Némati, E. Lepeltier, P. Pigeon, G. Jaouen, D. Decaudin, et C. Passirani, « Ferrocifen stealth LNCs and conventional chemotherapy: a promising combination against multidrug-resistant ovarian adenocarcinoma », International Journal of Pharmaceutics, vol. 626, p. 122164, sept. 2022.
    Résumé : Ovarian cancer is one of the deadliest epithelial malignancies in women, owing to the multidrug resistance that restricts the success of conventional chemotherapy, carboplatin and paclitaxel. High grade serous ovarian carcinoma can be classified into two subtypes, the chemosensitive High OXPHOS and the Low OXPHOS tumour, less sensitive to chemotherapy. This difference of treatment efficacy could be explained by the redox status of these tumours, High OXPHOS exhibiting a chronic oxidative stress and an accumulation of reactive oxygen species. Ferrocifens, bio-organometallic compounds, are believed to be ROS producers with a good cytotoxicity on ovarian cancer cell lines. The aim of this study was to evaluate the in vivo efficacy of ferrocifen stealth lipid nanocapsules on High and Low OXPHOS ovarian Patient-Derived Xenograft models, alone or in combination to standard chemotherapy. Accordingly, two ferrocifens, P53 and P722, were encapsulated in stealth LNCs. The treatment by stealth P722-LNCs in combination with standard chemotherapy induced, with a concentration eight time lower than in stealth P53-LNCs, similar tumour reduction on a Low OXPHOS model, allowing us to conclude that P722 could be a leading ferrocifen to treat ovarian cancer. This combination of treatments may represent a promising synergistic approach to treat resistant ovarian adenocarcinoma.
    Mots-clés : CHEMBIO, Multidrug resistance, Nanoparticle, Organometallic compound, Ovarian cancer, Patient-Derived Xenograft model, POLE 3, ROS producer molecule.
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  • Y. Mazouzi, F. Sallem, F. Farina, A. Loiseau, N. R. Tartaglia, M. Fontaine, A. Parikh, M. Salmain, C. Neri, et S. Boujday, « Biosensing Extracellular Vesicle Subpopulations in Neurodegenerative Disease Conditions », ACS Sensors, vol. 7, nᵒ 6, p. 1657-1665, juin 2022.
    Résumé : Extracellular vesicles (EVs) are secreted nanoparticles that are involved in intercellular communication and that modulate a wide range of biological processes in normal and disease conditions. However, EVs are highly heterogeneous in terms of origin in the cell, size, and density. As a result, complex protocols are required to identify and characterize specific EV subpopulations, limiting biomedical applications, notably in diagnostics. Here, we show that combining quartz crystal microbalance with dissipation (QCM-D) and nanoplasmonic sensing (NPS) provides a facile method to track the viscoelastic properties of small EVs. We applied this multisensing strategy to analyze small EVs isolated by differential ultracentrifugation from knock-in mouse striatal cells expressing either a mutated allele or wild-type allele of huntingtin (Htt), the Huntington’s disease gene. Our results validate the sensing strategy coupling QCM-D and NPS and suggest that the mass and viscoelastic dissipation of EVs can serve as potent biomarkers for sensing the intercellular changes associated with the neurodegenerative condition.
    Mots-clés : CHEMBIO, POLE 3.
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  • F. Najlaoui, B. Busser, G. S. Taïwe, P. Pigeon, N. Sturm, D. Giovannini, N. Marrakchi, A. Rhouma, G. Jaouen, S. Gibaud, et M. De Waard, « Succinimido–Ferrocidiphenol Complexed with Cyclodextrins Inhibits Glioblastoma Tumor Growth In Vitro and In Vivo without Noticeable Adverse Toxicity », Molecules, vol. 27, nᵒ 14, p. 4651, 2022.
    Résumé : SuccFerr (N-[4-ferrocenyl,5-5-bis (4-hydroxyphenyl)-pent-4-enyl]-succinimide) has remarkable antiproliferative effects in vitro, attributed to the formation of a stabilized quinone methide. The present article reports in vivo results for a possible preclinical study. SuccFerr is lipophilic and insoluble in water, so the development of a formulation to obviate this inconvenience was necessary. This was achieved by complexation with randomly methylated cyclodextrins (RAMEßCDs). This supramolecular water-soluble system allowed the in vivo experiments below to proceed. Application of SuccFerr on the glioblastoma cancer cell line U87 indicates that it affects the cellular cycle by inducing a blockade at G0/G1 phase, linked to apoptosis, and another one at the S phase, associated with senescence. Using healthy Fischer rats, we show that both intravenous and subcutaneous SuccFerr: RAMEßCD administration at 5 mg/kg lacks toxic effects on several organs. To reach lethality, doses higher than 200 mg/kg need to be administered. These results prompted us to perform an ectopic in vivo study at 1 mg/kg i.v. ferrocidiphenol SuccFerr using F98 cells xenografted in rats. Halting of cancer progression was observed after six days of injection, associated with an immunological defense response linked to the active principle. These results demonstrate that the properties of the selected ferrocidiphenol SuccFerr transfer successfully to in vivo conditions, leading to interesting therapeutic perspectives based on this chemistry.
    Mots-clés : anticancer drug, CHEMBIO, cyclodextrin, ferrocenyl tamoxifen derivatives, glioblastoma, POLE 3.
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  • M. Nicolas, B. Beito, M. Oliveira, M. Tudela Martins, B. Gallas, M. Salmain, S. Boujday, et V. Humblot, « Strategies for Antimicrobial Peptides Immobilization on Surfaces to Prevent Biofilm Growth on Biomedical Devices », Antibiotics, vol. 11, nᵒ 1, p. 13, 2022.
    Résumé : Nosocomial and medical device-induced biofilm infections affect millions of lives and urgently require innovative preventive approaches. These pathologies have led to the development of numerous antimicrobial strategies, an emergent topic involving both natural and synthetic routes, among which some are currently under testing for clinical approval and use. Antimicrobial peptides (AMPs) are ideal candidates for this fight. Therefore, the strategies involving surface functionalization with AMPs to prevent bacterial attachment/biofilms formation have experienced a tremendous development over the last decade. In this review, we describe the different mechanisms of action by which AMPs prevent bacterial adhesion and/or biofilm formation to better address their potential as anti-infective agents. We additionally analyze AMP immobilization techniques on a variety of materials, with a focus on biomedical applications. Furthermore, we summarize the advances made to date regarding the immobilization strategies of AMPs on various surfaces and their ability to prevent the adhesion of various microorganisms. Progress toward the clinical approval of AMPs in antibiotherapy is also reviewed.
    Mots-clés : AMP, antimicrobial, biofilms, biofunctionalization, CHEMBIO, immobilization, peptide, POLE 3.
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  • P. Pigeon, M. Gaschard, M. Othman, M. Salmain, et G. Jaouen, « α-Hydroxylactams as Efficient Entries to Diversely Functionalized Ferrociphenols: Synthesis and Antiproliferative Activity Studies », Molecules, vol. 27, nᵒ 14, p. 4549, 2022.
    Résumé : The [ferrocene-ene-phenol] motif has been identified as the pharmacophore responsible for the anticancer activity of the family of ferrocene-based molecules coined ferrocifens, owing to its unique redox properties. The addition of imide entities to the historical ferrociphenol scaffold tremendously enhanced the cytotoxic activity of a large panel of cancer cell cultures and preliminary studies showed that the reduction of one of the carbonyl groups of the imide groups to the corresponding α-hydroxylactams only slightly affected the antiproliferative activity. As a continuation to these studies, we took advantage of the facile conversion of α-hydroxylactams to highly electrophilic N-acyliminium ions to graft various substituents to the imide motif of phthalimido ferrocidiphenol. Cell viability studies showed that the newly synthesized compounds showed diverse cytotoxic activities on two breast cancer cell lines, while only one compound was significantly less active on the non-tumorigenic cell line hTERT-RPE1.
    Mots-clés : <i>N</i>-acyliminium ion, anticancer activity, CHEMBIO, ferrocene, ferrocifen, hydroxylactam, POLE 3.
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  • J. Sanz Garcia, M. Gaschard, I. Navizet, M. Sahihi, S. Top, Y. Wang, P. Pigeon, A. Vessières, M. Salmain, et G. Jaouen, « Inhibition of cathepsin B by ferrocenyl indenes highlights a new pharmacological facet of ferrocifens », European Journal of Inorganic Chemistry, vol. 2022, nᵒ 9, p. e202101075, janv. 2022.
    Résumé : The family of ferrocifens initially built up from the anti-estrogen tamoxifen shows a broad antitumor activity both  in vitro  and  in vivo . Their mechanism of action relies on the presence of the redox motif [ferrocene-ene-phenol] that, under oxidative conditions, generates reactive oxygen species (ROS) and affords electrophilic quinone methides (QMs) having the ability to alkylate biological nucleophiles and in turn elicit a strong antiproliferative activity. In this context, the cysteine protease cathepsin B was initially presumed to be a target for ferrocenyl QMs.  In vitro  enzymatic assays ruled out this hypothesis but unexpectedly revealed that other ferrocifen metabolites, i.e. ferrocenyl indenes, acted as moderate inhibitors of cathepsin B. These experimental results were nicely confirmed by molecular docking calculations, that showed that the monophenol ferrocenyl indene and to a lower extent the diphenol interacted with the active site of cathepsin B, making it an unanticipated target of ferrocifens.
    Mots-clés : antitumor agent, bioorganometallic chemistry, CHEMBIO, computational chemistry, cysteine protease, docking, POLE 3.
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  • M. Soroush, W. Ait Mammar, A. Wilson, H. Ghourchian, M. Salmain, et S. Boujday, « Design and Optimization of a Magneto-Plasmonic Sandwich Biosensor for Integration within Microfluidic Devices », Biosensors, vol. 12, nᵒ 10, p. 799, 2022.
    Résumé : We designed a magneto-plasmonic biosensor for the immunodetection of antigens in minute sample volume. Both spherical gold nanoparticles (AuNP) and magnetic beads (MB) were conjugated to goat anti-rabbit IgG antibody (Ab) capable of recognizing a model target, rabbit IgG (rIgG). The AuNP bioconjugate was used as the optical detection probe while the MB one was used as the capture probe. Addition of the target analyte followed by detection probe resulted in the formation of a sandwich immunocomplex which was separated from the unbound AuNP-Ab conjugate by application of an external magnetic field. The readout was executed either in a direct or in indirect way by measuring the UV–Visible spectrum of each fraction in a specially designed microcell. Dose–response curves were established from the optical signal of the immunocomplex and unbound AuNP-Ab conjugate fractions. Finally, the assay was transposed to a microfluidic cell specially designed to enable easy separation of the immunocomplex and AuNP-Ab conjugate fractions and subsequent analysis of the latter fraction and achieve the quantification of the analyte in the ng/mL concentration range.
    Mots-clés : CHEMBIO, gold nanoparticles, immunosensor, magnetic beads, microfluidic chip, optical transduction, POLE 3.
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  • Y. Wang, P. Pigeon, W. Li, J. Yan, P. M. Dansette, M. Othman, M. J. McGlinchey, et G. Jaouen, « Diversity-oriented synthesis and bioactivity evaluation of N-substituted ferrocifen compounds as novel antiproliferative agents against TNBC cancer cells », European Journal of Medicinal Chemistry, p. 114202, mars 2022.
    Résumé : Ferrociphenols are characterized by the presence of a biologically active redox motif [ferrocenyl-ene-p-phenol], and are known to exhibit anticancer properties. Recent studies have identified a new series of ferrociphenols that bear an imido-type heterocycle at the terminus of a short alkyl chain, and which showed very strong antiproliferativity against multiple types of cancer cells. This work describes the syntheses and an SAR study of ferrociphenols bearing a diversity-based range of nitrogen-containing substituents on the alkyl chain. Preliminary oxidative metabolism experiments and ROS-related bioactivity measurements were also carried out to probe the origin of the cytotoxicity of the imido-ferrociphenols. Furthermore, an interesting dimerization phenomenon was observed in the X-ray crystal structure of the 2,3-naphthalenedicarboximidopropyl-ferrocidiphenol, 21, which may be a factor in decreasing its rate of oxidation to form the corresponding quinone methide, 21-QM, thereby affecting its antitumor activity. These results suggest that both the formation rate and the stability of QMs could affect the antiproliferative activity of their ferrociphenol precursors.
    Mots-clés : Anticancer agents, Bioorganometallic chemistry, CHEMBIO, Ferrocene, Imides, POLE 3, Quinones.
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  • F. Zhao, M. Abdellaoui, W. Hagui, M. Ballarin-Marion, J. Berthet, V. Corcé, S. Delbaere, H. Dossmann, A. Espagne, J. Forté, L. Jullien, T. Le Saux, V. Mouriès-Mansuy, C. Ollivier, et L. Fensterbank, « Reactant-induced photoactivation of in situ generated organogold intermediates leading to alkynylated indoles via Csp2-Csp cross-coupling », Nature Communications, vol. 13, nᵒ 1, p. 2295, avr. 2022.
    Résumé : Photosensitization of organogold intermediates is an emerging field in catalysis. In this context, an access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process is observed. Of note, 2-iodo-ynamides can be used as electrophiles in this cross-coupling reaction. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converge on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.
    Mots-clés : CHEMBIO, CSOB, MACO, Photocatalysis, POLE 1, POLE 3, Reaction mechanisms.
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2021



  • S. Boujday et M. Salmain, « Nanoparticules d’or pour les biocapteurs : lecture optique de la reconnaissance moléculaire », Photoniques, nᵒ 106, p. 39-43, janv. 2021.
    Résumé : Les propriétés extraordinaires des nanoparticules d’or et/ou d’argent en ont fait des objets courtisés par les scientifiques toutes disciplines confondues. L’intensité de leur couleur ainsi que leur grande sensibilité optique au milieu environnant en font de puissants transducteurs pour les biocapteurs ; que ce soit grâce à des spectrophotomètres ou simplement par observation à l’oeil nu. Elles assurent la lecture de la reconnaissance moléculaire via des scénarios variés alliant simplicité et faible coût.
    Mots-clés : CHEMBIO, POLE 3.
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  • L. Chang, N. Fischer-Durand, G. Gontard, B. Bertrand, S. Thorimbert, et L. Dechoux, « A solvent-free, catalyst-free formal [3+3] cycloaddition dearomatization strategy: towards new fluorophores for biomolecules labelling », ChemSusChem, vol. 14, nᵒ 8, p. 1821-1824, 2021.
    Résumé : A general, sustainable dearomatization reaction for nitrogen-containing heterocycles was developed. Under solvent free conditions and without catalyst, the biorenewable methyl coumalate ( MC ) reacts as an efficient C3 partner to convert eleven types of basic aromatic rings into their pyrido[1,2-a] fused derivatives in good to excellent yields. The fluorescence properties of some of the products were harnessed to conjugate fluorescent tags to BSA and immunoglobulin G.
    Mots-clés : CHEMBIO, dearomatization reaction, fluorescent probes, methyl coumalate, Michael addition, Nitrogen heterocycles, POLE 3.
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  • 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. 27, nᵒ 63, p. 15773-15785, 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.
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  • E. Levernier, K. Jaouadi, H. - R. Zhang, V. Corcé, A. Bernard, G. Gontard, C. Troufflard, L. Grimaud, E. Derat, C. Ollivier, et L. Fensterbank, « Phenyl Silicates with Substituted Catecholate Ligands: Synthesis, Structural Studies and Reactivity », Chemistry – A European Journal, vol. 27, nᵒ 34, p. 8782-8790, 2021.
    Résumé : While the generation of aryl radicals by photoredox catalysis under reductive conditions is well documented, it has remained challenging under an oxidative pathway. Because of the easy photo-oxidation of alkyl bis-catecholato silicates, a general study of phenyl silicates bearing substituted catecholate ligands has been achieved. The newly synthesized phenyl silicates have been fully characterized, and their reactivity has been explored. It was found that, thanks to the substitution of the catecholate moiety, notably with the 4-cyanocatecholato ligand, the phenyl radical could be generated and trapped. Computational studies provided a rationale for these findings.
    Mots-clés : aryl radicals, CHEMBIO, MACO, oxidation, photoredox catalysis, POLE 1, POLE 3, silicates.
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  • Y. Mazouzi, A. Miche, A. Loiseau, B. Beito, C. Méthivier, D. Knopp, M. Salmain, et S. Boujday, « Design and Analytical Performances of a Diclofenac Biosensor for Water Resources Monitoring », ACS sensors, vol. 6, nᵒ 9, p. 3485-3493, août 2021.
    Résumé : Because the broadly consumed pain killer diclofenac (DCF) is a recognized pollutant, monitoring of its concentration is routinely performed in surface waters. As a valuable alternative to chromatographic and immunochemical assays, we developed a piezoelectric immunosensor to quantify DCF, first in buffer (PBS) and then in river water samples. A sensing layer comprising DCF was built up on the surface of silica-coated quartz sensors using a robust coupling chemistry. Binding of a highly affine monoclonal anti-DCF antibody was monitored in real time by quartz crystal microbalance with dissipation (QCM-D) measurements from which were determined a dissociation constant KD of 0.24 nM and an acoustic antibody surface coverage of 1120 ng/cm2 at saturation. On the other hand, an optical antibody surface coverage of 260 ng/cm2 was determined by combined nanoplasmonic sensing measurement, giving a hydration percentage of 75% for the antibody monolayer. DCF assay was further set up following a competitive format for which binding of antibody to the sensing layer is inhibited by DCF in solution. The piezoelectric sensor response expressed as frequency shift ΔF was inversely related to the concentration of DCF with a dynamic range of 15-46 nM and a limit of detection (LoD) of 9.5 nM (2.8 μg/L) in PBS. This piezoelectric immunosensor was eventually applied to the assay of DCF in surface water samples taken at three different locations in the Seine and Marne rivers. The calculated concentration of DCF in these samples was in good agreement with official data published by the French center of water analysis eaufrance.
    Mots-clés : antibody, CHEMBIO, immunosensor, nanoplasmonics, nonsteroidal anti-inflammatory drug, POLE 3, quartz crystal microbalance.
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  • C. Passirani, A. Vessières, G. La Regina, W. Link, et R. Silvestri, « Modulating undruggable targets to overcome cancer therapy resistance », Drug Resistance Updates, vol. 60, p. 100788, déc. 2021.
    Résumé : 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 iden

    tification 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.
    Mots-clés : 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, et 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, août 2021.
    Résumé : 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.
    Mots-clés : CHEMBIO, POLE 3.
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  • R. Ramos, J. - F. Gilles, R. Morichon, C. Przybylski, B. Caron, C. Botuha, A. Karaiskou, M. Salmain, et 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.
    Résumé : 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.
    Mots-clés : CHEMBIO, CSOB, POLE 3.
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  • S. Topin-Ruiz, A. Mellinger, E. Lepeltier, C. Bourreau, J. Fouillet, J. Riou, G. Jaouen, L. Martin, C. Passirani, et 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, janv. 2021.
    Résumé : 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.
    Mots-clés : apoptosis, CD8 T lymphocytes, CHEMBIO, Ferrocifen, metastatic melanoma, POLE 3.
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  • A. Vessières, Y. Wang, M. J. McGlinchey, et 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.

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, et 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, sept. 2020.
    Résumé : 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 better 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.
    Mots-clés : CHEMBIO, POLE 3.
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  • A. Beghennou, K. Passador, A. Passador, V. Corcé, S. Thorimbert, et 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, sept. 2020.
    Résumé : 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.
    Mots-clés : Antihistamines, CHEMBIO, Pinner reaction, POLE 3, Pyridopyridinones, Seleno-mediated cyclization, δ-Lactone.
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  • L. Cunningham, Y. Wang, C. Nottingham, J. Pagsulingan, G. Jaouen, M. McGlinchey, et 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, mai 2020.
    Résumé : 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.
    Mots-clés : anti-cancer activity, asymmetric synthesis, CHEMBIO, Ferrocene, McMurry coupling, POLE 3.
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  • D. Jamroz, N. Fischer-Durand, M. Palusiak, S. Wojtulewski, S. Jarzyński, M. Stępniewska, M. Salmain, et 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, avr. 2020.
    Résumé : 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.
    Mots-clés : bioconjugation, CHEMBIO, iEDDA, metallocarbonyl complex, norbornene, POLE 3, tetrazine.
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  • Š. Nováková Lachmanová, L. Pospíšil, J. Šebera, B. Talbi, M. Salmain, et M. Hromadová, « Electrochemical characterization of the artificial metalloenzyme papain-[(η6-arene)Ru(1,10-phenanthroline)Cl]+ », Journal of Electroanalytical Chemistry, vol. 859, p. 113882, févr. 2020.
    Résumé : 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.
    Mots-clés : Artificial metalloenzyme, CHEMBIO, Electrochemical admittance and impedance techniques, Papain, POLE 3, Ruthenium(II) complexes.
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  • J. P. Rada, J. Forté, G. Gontard, V. Corcé, M. Salmain, et 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, avr. 2020.
    Résumé : 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.
    Mots-clés : 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, et 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.
    Résumé : 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
    Mots-clés : CHEMBIO, POLE 3.
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  • K. Wu, B. Pudasaini, J. Y. Park, S. Top, G. Jaouen, M. - H. Baik, et 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, févr. 2020.
    Résumé : 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.
    Mots-clés : CHEMBIO, POLE 3.
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2019



  • A. Casini, A. Vessières, et S. M. Meier-Menches, Metal-based Anticancer Agents, Royal Society of Chemistry. 2019.
    Résumé : 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.
    Mots-clés : CHEMBIO, POLE 3.
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  • V. Corcé, C. Lévêque, C. Ollivier, et L. Fensterbank, « 15 Silicates in Photocatalysis », in Photocatalysis in Organic Synthesis, 1st editionᵉʳ éd., Thieme Verlag, 2019.
    Résumé : Bis(catecholato)silicates have emerged as robust alkyl radical sources under photocatalysis. This chapter describes the preparation of various silicates and their utilization under photocatalytic conditions for the formation of C–C and C–O bonds. The last section focuses on the use of silicates in photoredox/nickel dual catalysis.
    Mots-clés : CHEMBIO, MACO, POLE 3.
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  • T. Dallagi, M. Saidi, G. Jaouen, et S. Top, « Synthesis and biodistribution of 1-[2-(cyclopentadienyltricarbonyltechnetium-99m)-2-oxo-ethoxy-phenyl]-1,2-di- (p-hydroxyphenyl)but-1-ene for tumor imaging », Journal of Organometallic Chemistry, vol. 891, p. 1-6, août 2019.
    Résumé : The high incidence and mortality of breast cancer and other estrogen receptor related tumors motivates efforts to develop innovative imaging probes to effectively diagnose, evaluate the extent of the tumor, and predict the efficacy of treatments while concurrently and selectively delivering anticancer agents to the cancer tissues. In the present study, 1-[2-(cyclopentadienyltricarbonyltechnetium-99m)-2-oxo-ethoxy-phenyl]-1,2-di-(p-hydroxyphenyl)but-1-ene was prepared and investigated as a potential agent for imaging estrogen receptors (ERs) in associated tumors. The compound was obtained in high radiochemical purity and radiochemical yields. The biodistribution of the radioactive compound in mature female rats showed an ER-mediation in the ovarian target tissues as the uptake was reduced by a blocking dose of estradiol. The nonspecific uptake in muscle was relatively low.
    Mots-clés : Biodistribution, CHEMBIO, Estrogen receptor, POLE 3, SPECT, Tc radiolabelling, Tumor, Tumor imaging.
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  • N. Fischer-Durand, D. Lizinska, V. Guérineau, B. Rudolf, et M. Salmain, « ‘Clickable’ cyclopentadienyl iron carbonyl complexes for bioorthogonal conjugation of mid-infrared labels to a model protein and PAMAM dendrimer », Applied Organometallic Chemistry, vol. 33, nᵒ 4, p. e4798, avr. 2019.
    Résumé : Owing to the intrinsic limitations of the conventional bioconjugation methods involving native nucleophilic functions of proteins, we sought to develop alternative approaches to introduce metallocarbonyl infrared labels onto proteins on the basis of the [3?+?2] dipolar azide-alkyne cycloaddition (AAC). To this end, two cyclopentadienyl iron dicarbonyl (Fp) complexes carrying a terminal or a strained alkyne handle were synthesized. Their reactivity was examined towards a model protein and poly (amidoamine) (PAMAM) dendrimer, both carrying azido groups. While the copper (I)-catalysed azide-alkyne cycloaddition (CuAAC) proceeded smoothly with the terminal alkyne metallocarbonyl derivative, labelling by strain-promoted azide-alkyne cycloaddition (SPAAC) was less successful in terms of final coupling ratios. Infrared spectral characterization of the bioconjugates showed the presence of two bands in the 2000?cm?1 region, owing to the stretching vibration modes of the carbonyl ligands of the Fp entities.
    Mots-clés : bioconjugation, CHEMBIO, copper (I)-catalysed azide-alkyne cycloaddition, infrared spectroscopy, metallocarbonyl complex, POLE 3, strain-promoted azide-alkyne cycloaddition.
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  • F. Fus, Y. Yang, S. Lee, S. Top, M. Carriere, A. Bouron, A. Pacureanu, J. Da Silva, M. Salmain, A. Vessieres, P. Cloetens, G. Jaouen, et S. Bohic, « Intracellular localization of an osmocenyl-tamoxifen derivative in breast cancer cells revealed by synchrotron radiation X-ray fluorescence nanoimaging », Angewandte Chemie, vol. 58, nᵒ 11, p. 3461-3465, janv. 2019.
    Résumé : We have recently developed a series of tamoxifen-like metallocifens of the group-8 metals (Fe, Ru and Os) with strong antiproliferative activity on the triple negative breast cancer cells (MDA-MB-231). This property, not observed for the organic analog 4-hydroxytamoxifen, has been associated with the unique redox behavior of metallocenic moieties, readily affording reactive quinone methides in cancer cells. To shed light on the mechanism of action of these molecules, synchrotron radiation X-ray fluorescence (SR-XRF) nanoimaging studies were performed on cells exposed to osmocenyl-tamoxifen (Oc-OH-Tam) to disclose its intracellular distribution using osmium as an intrinsic reporter. High resolution mapping of the lipophilic Oc-OH-Tam in cells, revealed its preferential accumulation in the endomembrane system encompassing endoplasmic reticulum, nuclear envelope and vesicular structures. This is consistent with the ability of the amino nitrogen chain of the compounds to be protonated at physiological pH and responsible for electrostatic interactions between Oc-OH-Tam and membranes. We propose a comprehensive scenario that provides new insight into the cellular behavior and activation of Oc-OH-Tam and advances the understanding of its mechanism of action.
    Mots-clés : bioorganometallic chemistry, breast cancer cells, CHEMBIO, elemental tomography, osmium, POLE 3, synchrotron X-ray fluorescence.
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  • L. Guyon, E. Lepeltier, J. - C. Gimel, B. Calvignac, F. Franconi, N. Lautram, A. Dupont, C. Bourgaux, P. Pigeon, P. Saulnier, G. Jaouen, et C. Passirani, « Importance of Combining Advanced Particle Size Analysis Techniques To Characterize Cell-Penetrating Peptide–Ferrocifen Self-Assemblies », The Journal of Physical Chemistry Letters, vol. 10, nᵒ 21, p. 6613-6620, oct. 2019.


  • N. Illy, V. Corcé, J. Zimbron, V. Molinié, M. Labourel, G. Tresset, J. Degrouard, M. Salmain, et P. Guégan, « pH-Sensitive Poly(ethylene glycol)/Poly(ethoxyethyl glycidyl ether) Block Copolymers: Synthesis, Characterization, Encapsulation, and Delivery of a Hydrophobic Drug », Macromolecular Chemistry and Physics, vol. 220, nᵒ 16, p. 1900210, août 2019.
    Résumé : Abstract Curcumin is a natural polyphenolic compound known for its numerous pharmacological properties. However, its low water solubility and instability at neutral pH are serious drawbacks preventing its use as an oral drug. Well-defined amphiphilic poly(ethylene glycol)-block-poly(ethoxyethyl glycidyl ether) (PEG-b-PEEGE) block copolymers carrying acid-labile acetal groups are synthesized by anionic ring-opening polymerization and investigated as potential pH-sensitive nano-carriers for delivery of curcumin to cancer cells. The nanoparticles, resulting from copolymer self-assembly in aqueous media, are characterized by dynamic light scattering and cryo-transmission electron microscopy. The nanoparticles? stabilities are evaluated in three different phosphate buffers (pH = 7.2, 6.4, and 5.3). The stability decreases at lower pH and a complete disappearance of the nanoparticles is noticed after 4 days at pH 5.3. Curcumin is encapsulated in hydrophobic core of mPEG40-b-PEEGE25 nanoparticles allowing significant enhancements of curcumin solubility in water and lifetime at neutral pH. In vitro curcumin release is studied at different pH by UV-spectroscopy and high-performance liquid chromatography (HPLC). The cytotoxicity of curcumin and curcumin encapsulated in micelles is evaluated by cell viability 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay on MDA-MB-231 human breast cancer cells.
    Mots-clés : amphiphilic polyethers, anionic-ring opening polymerization, CHEMBIO, curcumin encapsulation, pH-sensitive copolymers, POLE 3, POLE 4, POLYMERES, self-assembly.
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  • S. H. Z. Lee, F. Chau, S. Top, G. Jaouen, A. Vessières, E. Labbé, et O. Buriez, « New mechanistic insights into osmium-based tamoxifen derivatives », Electrochimica Acta, vol. 302, p. 130-136, févr. 2019.
    Résumé : The electrochemical behavior of osmociphenol (3, Oc-OH), an organometallic osmium-based anticancer drug candidate, has been investigated by cyclic voltammetry in the absence and presence of lutidine used as a base model. Osmociphenol exhibited spontaneous deprotonation of the phenol function upon oxidation of the osmocene moiety due to its high acidity. In the presence of lutidine, a base-dependent and different electrochemical behavior was observed at low scan rates indicating a second oxidation step leading to the corresponding cationic quinone methide precursor (3b+). However, compared to ruthenocene derivatives, the stability of 3b+ prevented its conversion into quinone methide as the final and stable complex. Despite differences in their oxidative processes, osmociphenol and ruthenociphenol derivatives exhibit similar biological activities.
    Mots-clés : Anti-cancer, Bioorganometallic, CHEMBIO, Cyclic voltammetry, Osmium, POLE 3, Tamoxifen.
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  • K. Passador, S. Thorimbert, et C. Botuha, « Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space », Synthesis, vol. 51, nᵒ 02, p. 384-398, 2019.
    Résumé : William Pitt and co-workers have created a virtual exploratory heterocyclic library ‘VEHICLe’ containing over 200 unconquered bicyclic heteroaromatic rings, synthetically feasible with potential medicinal interest. Since the publication of the 22 ‘heteroaromatic rings of the future’ by Pitt in 2009, 15 of them have been successfully synthesized as bicyclic or polycyclic forms and evaluated for applications in both biology and material science. This short review presents the critical synthesis associated with innovative synthetic methodologies of the synthetically conquered ring scaffolds from the list of 22 with a spotlight on the scientific contribution of this fascinating article for the expansion of the chemical diversity.
    Mots-clés : CHEMBIO, POLE 3.
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  • Y. Wang, P. Pigeon, S. Top, J. García, C. Troufflard, I. Ciofini, M. J. McGlinchey, et G. Jaouen, « Atypical lone pair-π interaction with quinone methides in a series of imido-ferrociphenol anticancer drug candidates », Angewandte Chemie International Edition, vol. 58, nᵒ ja, p. 8421-8425, avr. 2019.
    Résumé : Ferrociphenols, especially those possessing a heterocycle at the terminus of an aliphatic chain, display strong anticancer activity via a novel redox mechanism that generates active metabolites such as quinone methides (QMs). X-ray crystallography and UV-Vis spectroscopy reveal that the specific lone pair (lp)-π interaction between a carbonyl group of the imide and the quinone motif of the QM plays an important role in the exceptional cytotoxic behaviour of their imido-ferrociphenol precursors. This intramolecular lp-π interaction markedly enhanced the stability of the QMs and lowered the pKa values of the corresponding phenolates. As the first example of such a non-covalent interaction that stabilizes QMs remotely, it not only expands the scope of the lp-π interaction in supramolecular chemistry, but also represents a new mode of stabilization of a QM. This unprecedented application of lp-π interactions in imido-ferrociphenol anticancer drug candidates may also have great potential in drug discovery and organocatalyst design.
    Mots-clés : antitumor agents, bioorganometallics, CHEMBIO, ferrocifen, non-covalent interactions, POLE 3, quinones.
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  • L. Zhang, P. Chen, A. Loiseau, D. Brouri, S. Casale, M. Salmain, S. Boujday, et B. Liedberg, « Spatially Controlled Reduction and Growth of Silver in Hollow Gold Nanoshell Particles », The Journal of Physical Chemistry C, vol. 123, nᵒ 16, p. 10614-10621, avr. 2019.
    Résumé : Spatially controlled reactions at the nanoscale have attracted increasing interest for fundamental chemistry and for the engineering of novel functional materials. Herein, we demonstrate that pH-triggered reduction of silver ions preferentially occurs at the inner walls of porous and citrate-capped gold nanoshell (AuNS) particles. The reaction initially relies on the presence of sacrificial silver ions inside the AuNS particles as well as in the surrounding preparation solution, and it proceeds upon external addition of silver ions until a solid silver core is formed inside the AuNS particles. Subsequent reduction of silver occurs on the external surface of the solidified AuNS, resulting in a layered and compositionally complex nanoparticle containing both silver and gold. Growth experiments performed in the dark, under white light illumination, as well as near resonance suggest that the reduction reaction is not guided by a plasmonic field enh

    ancement effect. This is in contrast to the recently proposed hot spot mechanism of silver reduction at the rim of nanoholes in a periodic gold array. Our observations point toward a confinement process that proceeds via a continuous supply of silver ions that diffuse from the external solution through the porous shell into the inner volume of the AuNS particles where they become reduced.
    Mots-clés : CHEMBIO, POLE 3.
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  • L. Zhang, D. Hu, M. Salmain, B. Liedberg, et S. Boujday, « Direct quantification of surface coverage of antibody in IgG-Gold nanoparticles conjugates », Talanta, vol. 204, p. 875-881, nov. 2019.
    Résumé : It is of paramount importance to be able to accurately quantify surface coverage of antibodies on gold nanoparticles (AuNP) so as to optimise the sensitivity of AuNP-based immunosensors. Herein, we developed a fluorescence-based method to directly quantify rabbit immunoglobulin G (IgG) used as antibody model bound to AuNP. Rabbit IgG was first labelled with fluorescein-5-isothiocyanate (FITC) prior to conjugation to AuNP via either physisorption or chemisorption. IgG-conjugated AuNP were treated with NaCN to dissolve the AuNP and restore the fluorescence emission that was quenched in the presence of the metallic colloids, followed by quantification of fluorescein by spectrofluorimetry. This direct assay gave about 4 IgG bound to each 15-nm diameter AuNP for both immobilization strategies. This surface coverage value was in good agreement with that determined from the theoretical value calculated from the Localized Surface Plasmon Resonance (LSPR) band shift. For comparison, we also applied two indirect methods based on the quantitation of excess IgG remaining in the supernatant using fluorescence assay or enzyme-linked immunosorbent assay (ELISA). The indirect assays, either fluorescence or ELISA, commonly used to assess the antibody coverage on AuNP, overestimated the IgG surface coverage to a large extent, since up to 3 to 4 times higher coverages were measured. Therefore, the direct fluorescence method reported in this paper appears as a valuable method for quantification of surface coverage of antibody on AuNP.
    Mots-clés : Adsorption, CHEMBIO, Fluorescence, Gold nanoparticles, Immunoglobulin G (IgG), POLE 3, Quantification.
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  • L. Zhang, M. Salmain, B. Liedberg, et S. Boujday, « Naked Eye Immunosensing of Food Biotoxins Using Gold Nanoparticle-Antibody Bioconjugates », ACS Applied Nano Materials, vol. 2, nᵒ 7, p. 4150-4158, juill. 2019.
    Résumé : Colorimetric immunoassays using gold nanoparticles (AuNP) form a special class of assays where AuNP act as a transducer to monitor binding events between an antigen and an antibody. Indeed, AuNP display unique optical properties that can been exploited in various ways to develop biosensors. One of the most striking properties of colloidal AuNP (and more generally of noble metal nanomaterials) is their extremely high extinction coefficient in the visible range of the spectrum owing to the localized surface plasmon resonance (LSPR) phenomenon. This feature makes AuNP detectable down to very low concentrations by absorption spectroscopy or even by the naked eye. Herein we took advantage of the high detectability of AuNP to design a solid-phase, sandwich-type, colorimetric immunosensor aiming at the detection of staphylococcal enterotoxin A (SEA). A test zone comprised of a polyclonal anti-SEA antibody was created at the surface of amino-functionalized glass slides via high affinity binding to covalently immobilized Protein A. The same antibody was conjugated to 13 nm diameter AuNP to afford the nanoimmunoprobe. After the glass slides were successively exposed to SEA and AuNP-antibody bioconjugate, a distinct red spot appeared at the detection zone from as low as 1 ng SEA in buffer. Quantification of SEA in the 10–500 ng/mL range was established using a benchtop UV–visible spectrometer by integration of the LSPR band centered at 530 nm. Eventually, this biosensor was applied to the detection of SEA in milk with a limit of detection of 1.5 ng/mL.
    Mots-clés : CHEMBIO, POLE 3.
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2018



  • F. Fus, Y. Yang, H. Z. S. Lee, S. Top, M. Carriere, A. Bouron, A. Pacureanu, J. C. da Silva, M. Salmain, A. Vessieres, P. Cloetens, G. Jaouen, et S. Bohic, « Synchrotron Radiation X-Ray Fluorescence Nanoimaging Reveal the Intracellular Localization of Potent Anticancer Drug Osmocenyl-Tamoxifen Derivative », Microscopy and Microanalysis, vol. 24, nᵒ S2, p. 348-349, 2018.


  • F. Najlaoui, P. Pigeon, S. Aroui, M. Pezet, L. Sancey, N. Marrakchi, A. Rhouma, G. Jaouen, M. Waard, B. Busser, et S. Gibaud, « Anticancer properties of lipid and poly(ε-caprolactone) nanocapsules loaded with ferrocenyl-tamoxifen derivatives », Journal of Pharmacy and Pharmacology, vol. 70, nᵒ 11, p. 1474-1484, août 2018.
    Résumé : Abstract Objective We synthesized new tamoxifen derivatives as anticancer drug candidates and elaborated on convection-enhanced delivery (CED) as a strategy for delivery. Methods To overcome the issue of their poor solubility, these ferrocenyl-tamoxifen derivatives were esterified and encapsulated into different nanocarriers, that is lipid (LNC) and polymeric nanocapsules (PNL-NC). We describe the chemistry, the encapsulation and the physicochemical characterization of these formulations. Key findings Starting compounds [phthalimido-ferrocidiphenol and succinimido-ferrocidiphenol], esterified prodrugs and their nanocapsules formulations were characterized. These drug candidates displayed a strong in vitro activity against breast and glioblastoma cancer cells. The ester prodrugs were toxic for glioblastoma cells (IC50 = 9.2 ? 10?2 ?m and 6.7 ? 10?2 ?m, respectively). The IC50 values for breast cancer cells were higher for these compounds. The encapsulation of the esterified compounds in LNCs (≈50 nm) or PCL-NCs (≈300 nm) did not prevent their efficacy on glioblastoma cells. These anticancer effects were due to both blockade in the S-phase of the cell cycle and apoptosis. Moreover, the tamoxifen derivatives-loaded nanocapsules induced no toxicity for healthy astrocytes and showed no haemolytic properties. Loaded Lipid Nanocapsules (LNCs) presented interesting profiles for the optimal delivery of active compounds. Conclusions Phthalimido- and Succinimido-esters represent an innovative approach to treat cancers with cerebral localizations such as glioblastoma or brain metastases from breast cancers.
    Mots-clés : breast cancer, CHEMBIO, ferrocenyl-tamoxifen derivatives, glioblastoma, Lipid nanocapsules, POLE 3, polymer nanocapsules.
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