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1. Lipo-chitin oligosaccharides, plant symbiosis signalling molecules that modulate mammalian angiogenesis in vitro.

Author

Michael A Djordjevic, Anna Bezos, Susanti, Laurence Marmuse, Hugues Driguez, Eric Samain, Boris Vauzeilles, Jean-Marie Beau, Farzaneh Kordbacheh, Barry G Rolfe, Ralf Schwörer, Alison M Daines, Peter M Gresshoff, and Christopher R Parish

Subjects
Medicine, Science
Abstract

Lipochitin oligosaccharides (LCOs) are signaling molecules required by ecologically and agronomically important bacteria and fungi to establish symbioses with diverse land plants. In plants, oligo-chitins and LCOs can differentially interact with different lysin motif (LysM) receptors and affect innate immunity responses or symbiosis-related pathways. In animals, oligo-chitins also induce innate immunity and other physiological responses but LCO recognition has not been demonstrated. Here LCO and LCO-like compounds are shown to be biologically active in mammals in a structure dependent way through the modulation of angiogenesis, a tightly-regulated process involving the induction and growth of new blood vessels from existing vessels. The testing of 24 LCO, LCO-like or oligo-chitin compounds resulted in structure-dependent effects on angiogenesis in vitro leading to promotion, or inhibition or nil effects. Like plants, the mammalian LCO biological activity depended upon the presence and type of terminal substitutions. Un-substituted oligo-chitins of similar chain lengths were unable to modulate angiogenesis indicating that mammalian cells, like plant cells, can distinguish between LCOs and un-substituted oligo-chitins. The cellular mode-of-action of the biologically active LCOs in mammals was determined. The stimulation or inhibition of endothelial cell adhesion to vitronectin or fibronectin correlated with their pro- or anti-angiogenic activity. Importantly, novel and more easily synthesised LCO-like disaccharide molecules were also biologically active and de-acetylated chitobiose was shown to be the primary structural basis of recognition. Given this, simpler chitin disaccharides derivatives based on the structure of biologically active LCOs were synthesised and purified and these showed biological activity in mammalian cells. Since important chronic disease states are linked to either insufficient or excessive angiogenesis, LCO and LCO-like molecules may have the potential to be a new, carbohydrate-based class of therapeutics for modulating angiogenesis.

Published
2014
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2. Assembly of Poly(vinylphosphonic acid)-Based Double Hydrophilic Block Copolymers by Gadolinium Ions for the Formation of Highly Stable MRI Contrast Agents

Author

Karolina H. Markiewicz, Laurence Marmuse, Margaux Mounsamy, Claire Billotey, Mathias Destarac, Christophe Mingotaud, Jean-Daniel Marty, Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), P3R - Polymères de Précision par Procédés Radicalaires (P3R), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT), Nano-H SAS, Institut Lumière Matière [Villeurbanne] (ILM), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Hospices Civils de Lyon (HCL), IDeAS - Interfaces Dynamiques et Assemblages Stimulables (IDeAS), and ANR-19-CE09-0011,Hybrid-MRI,Complexes hybrides polyioniques pour l'imagerie médicale(2019)

Subjects
Inorganic Chemistry, Polymers and Plastics, Organic Chemistry, Materials Chemistry, [CHIM]Chemical Sciences
Abstract

Mixing double-hydrophilic block copolymers containing a poly(vinylphosphonic acid) block with gadolinium ions in water leads to the spontaneous formation of polymeric nanoparticles. With an average diameter near 20 nm, the nanoparticles are stable after dilution or change of pH and ionic strength. High magnetic relaxivities were measured in vitro, and in vivo magnetic resonance imaging on rats demonstrates the high potential of such polymeric assemblies.

Published
2022

3. Synthesis of Highly-loaded Holmium-165 Siloxane Particles for Brachytherapy of Brain Cancer and Injectability Evaluation in Healthy Pig

Author

Olivier Tillement, Cédric Louis, Laurence Marmuse, Lionel Marcon, Frédérique Ponce, Helene Gehan, Claude Carozzo, Khoshnevis M, Institut Lumière Matière [Villeurbanne] (ILM), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon, Nano-H S.A.S, Interactions Cellules Environnement - UR (ICE), and VetAgro Sup - Institut national d'enseignement supérieur et de recherche en alimentation, santé animale, sciences agronomiques et de l'environnement (VAS)

Subjects
medicine.medical_treatment, Brachytherapy, Biomedical Engineering, Pharmaceutical Science, Medicine (miscellaneous), chemistry.chemical_element, Bioengineering, Nanotechnology, Context (language use), 02 engineering and technology, 030218 nuclear medicine & medical imaging, Suspension (chemistry), 03 medical and health sciences, 0302 clinical medicine, Spect imaging, Suspension, Zeta potential, medicine, [CHIM]Chemical Sciences, Holmium-165, Chemistry, 021001 nanoscience & nanotechnology, 3. Good health, Radiation therapy, Minipig, Stereotactic injection, 0210 nano-technology, Holmium, Glioblastoma, Injectability, Biomedical engineering
Abstract

International audience; Glioblastoma is the most invasive type of glial tumors, rapidly growing and commonly spreading into nearby brain tissue. Internal radiotherapy, also called brachytherapy, is an advanced cancer treatment where radioactive seeds are placed in or near the tumor itself, giving a high radiation dose to the tumor while reducing the radiation exposure in the surrounding healthy tissues. Among the available radioactive materials, 166Ho emits high-energy β radiation required for tumor destruction and low-energy γ radiation which can be used for quantitative SPECT imaging. In addition, Ho is a highly paramagnetic element and can therefore be visualized by MRI. In this context, we synthesized 400 nm particles via a sol-gel process in acidic conditions using holmium (III) oxide Ho2O3 as a nanostructured precursor. The objective was to design particles with a high 165Ho content combined with an enhanced stability suitable for brachytherapy of brain cancer following neutron activation. A sol-gel process was chosen to make Ho2O3 soluble in aqueous media and to improve particle’s colloidal stability. The resulting suspension showed enhanced colloidal stability in water, as evidenced by zeta potential and sedimentation rate measurements, combined with a high Ho content (28% w:w). Injectability and preliminary acute toxicity of the suspension were assessed after stereotactic injection in the brain of healthy minipig. Computerized tomography (CT) imaging was performed to visualize the injection sites and to determine the holmium distribution. It turns out that our suspension provided high 165Ho concentration to the site of action by way of stereotactic injection. This procedure allowed identifying suitable experimental conditions for future intratumoral injections of activated suspension.

Published
2017

4. Access to tetra-N-acetyl-chitopentaose by chemical N-acetylation of glucosamine pentamer

Author

Maher Abla, Catherine Ladavière, Jean-Pierre Vors, Frédéric Delolme, Stéphane Trombotto, Laurence Marmuse, Ingénierie des Matériaux Polymères (IMP), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Jean Monnet [Saint-Étienne] (UJM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de biologie et chimie des protéines [Lyon] (IBCP), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), and Bayer Cropscience

Subjects
Chitopentaose, Chitooligosaccharide, Polymers and Plastics, Pentamer, Hydrochloride, Pentoses, Oligosaccharides, Chitosan oligomer, 010402 general chemistry, 01 natural sciences, Chemical synthesis, Polymerization, chemistry.chemical_compound, Deprotonation, Glucosamine, Materials Chemistry, Organic chemistry, 010405 organic chemistry, Chemistry, Organic Chemistry, MALDI-TOF mass spectrometry, Acetylation, [CHIM.MATE]Chemical Sciences/Material chemistry, 0104 chemical sciences, Solvent, [CHIM.POLY]Chemical Sciences/Polymers, Yield (chemistry), Solvents, Selectivity
Abstract

International audience; Nowadays, the easy access of tetra-N-acetyl-chitopentaose and its counterparts is highly interesting since such chemical compounds are precursors of biological signal molecules with a strong agro-economic impact. The chemical synthesis of tetra-N-acetyl-chitopentaose by controlled N-acetylation of the glucosamine pentamer hydrochloride under mild conditions is described herein. A systematic study on the influence of the different parameters involved in this reaction, such as the solvent, the acetylating agent, and the base used for the deprotonation of ammonium groups of the starting material was carried out. The characterization of final reaction products by HPLC and MALDI-TOF mass spectrometry showed that each of these parameters affects differently the acetylation reaction. Whereas the solvent plays an important role in the N- or O-acetylation selectivity, the acetylating agent and the base were found to influence both the degree of N-acetylation and the distribution of the partially N-acetylated derivatives in the product mixtures. Based on these results, optimized reaction conditions have been established allowing tetra-N-acetyl-chitopentaose to be synthesized in a one-pot deprotonation/N-acetylation of the glucosamine pentamer hydrochloride in a moderate yield (ca 30%).

Published
2013

5. The molecular basis of polysaccharide cleavage by lytic polysaccharide monooxygenases

Author

Esther M. Johnston, Gideon J. Davies, Laurence Marmuse, Morten Tovborg, Leila Lo Leggio, Bernard Henrissat, Katja Salomon Johansen, Floriana Tuna, Amgalanbaatar Baldansuren, Paul H. Walton, Luisa Ciano, Hugues Driguez, Pernille von Freiesleben, Sébastien Fort, Glyn R. Hemsworth, Jens-Christian N. Poulsen, Thomas J. Simmons, Paul Dupree, Sylvain Cottaz, Kristian E. H. Frandsen, Nicolas Lenfant, Architecture et fonction des macromolécules biologiques (AFMB), Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU)-Institut National de la Recherche Agronomique (INRA), UK Biotechnology and Biological Sciences Research Council [BB/L000423, BB/L021633/1], Agence Francaise de l'Environnement et de la Maitrise de l'Energie [1201C102], Danish Council for Strategic Research [12-134923, 12-134922], European Community [283570], Institut de Chimie Moleculaire de Grenoble [FR 2607], LabEx ARCANE [ANR-11-LABX-0003-01], PolyNat Carnot Institute, French Agence Nationale de la Recherche [PNRB2005-11], Institut National de la Recherche Agronomique (INRA)-Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Dupree, Paul [0000-0001-9270-6286], Hemsworth, Glyn R [0000-0002-8226-1380], Ciano, Luisa [0000-0002-1667-0856], Baldansuren, Amgalanbaatar [0000-0001-8767-3731], Davies, Gideon J [0000-0002-7343-776X], Lo Leggio, Leila [0000-0002-5135-0882], Walton, Paul H [0000-0002-1152-1480], and Apollo - University of Cambridge Repository

Subjects
0301 basic medicine, Models, Molecular, conformation, coordination, oxygenases, Aspergillus oryzae, Oligosaccharides, Chitin, Lentinula, Crystallography, X-Ray, Mixed Function Oxygenases, Substrate Specificity, chemistry.chemical_compound, Catalytic Domain, Fluorescence Resonance Energy Transfer, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, biology, [SDV.BBM.BS]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Structural Biology [q-bio.BM], [SDV.BIBS]Life Sciences [q-bio]/Quantitative Methods [q-bio.QM], [SDV.BBM.BS]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biomolecules [q-bio.BM], Biochemistry, Oxidation-Reduction, Molecular Sequence Data, mechanism, Polysaccharide, chemistry, Article, 03 medical and health sciences, cellulose degradation, Oxidoreductase, Amino Acid Sequence, Cellulose, Molecular Biology, Binding Sites, Active site, Cell Biology, Monooxygenase, enzyme, 030104 developmental biology, Enzyme, substrate-specificity, biology.protein, activation, Copper, discovery
Abstract

Lytic polysaccharide monooxygenases (LPMOs) are copper-containing enzymes which oxidatively break down recalcitrant polysaccharides such as cellulose and chitin. Since their discovery LPMOs have become integral factors in the industrial utilization of biomass, especially in the sustainable generation of cellulosic bioethanol. We report here the first structural determination of an LPMO–oligosaccharide complex, yielding detailed insights into the mechanism of action of these enzymes. Using a combination of structure and electron paramagnetic resonance spectroscopy, we reveal the means by which LPMOs interact with saccharide substrates. We further uncover electronic and structural features of the enzyme active site, showing how LPMOs orchestrate the reaction of oxygen with polysaccharide chains.

Published
2016

6. Quantification of nanoparticle endocytosis based on double fluorescent pH-sensitive nanoparticles

Author

Valérie Forest, Jérémie Pourchez, Odile Sabido, Valérie Bin, Laurence Marmuse, Andréa Kurtz-Chalot, Jean-Philippe Klein, Michèle Cottier, Delphine Boudard, Ingénierie des Biomatériaux et des Particules Inhalées (BIOPI-ENSMSE), École des Mines de Saint-Étienne (Mines Saint-Étienne MSE), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-CIS, Institut Fédératif de Recherche en Sciences et Ingénierie de la Santé (IFRESIS-ENSMSE), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-IFR143, Laboratoire Interdisciplinaire d'Etude des Nanoparticules Aérosolisées (LINA-ENSMSE), Centre Hospitalier Universitaire de Saint-Etienne (CHU de Saint-Etienne), Université Jean Monnet [Saint-Étienne] (UJM), Nano-H, and LyonBioPôle

Subjects
cytotoxicity, Materials science, Silicon dioxide, [SDV]Life Sciences [q-bio], Biomedical Engineering, Nanoparticle, Nanotechnology, Endocytosis, size, Time-Lapse Imaging, Fluorescence spectroscopy, Silica particles, Mice, chemistry.chemical_compound, Microscopy, Animals, Fluorometry, Molecular Biology, Fluorescent Dyes, L-Lactate Dehydrogenase, Tumor Necrosis Factor-alpha, Cell Membrane, cellular uptake, Hydrogen-Ion Concentration, Silicon Dioxide, Fluorescence, macrophages, Oxidative Stress, RAW 264.7 Cells, chemistry, Biophysics, Nanoparticles, Nanomedicine, Chemical stability, Reactive Oxygen Species, Fluorescein-5-isothiocyanate
Abstract

International audience; Amorphous silica is a particularly interesting material because of its inertness and chemical stability. Silica nanoparticles have been recently developed for biomedical purposes but their innocuousness must be carefully investigated before clinical use. The relationship between nanoparticles physicochemical features, their uptake by cells and their biological activity represents a crucial issue, especially for the development of nanomedicine. This work aimed at adapting a method for the quantification of nanoparticle endocytosis based on pH-sensitive and double fluorescent particles. For that purpose, silica nanoparticles containing two fluorophores: FITC and pHrodoTM were developed, their respective fluorescence emission depends on the external pH. Indeed, FITC emits a green fluorescence at physiological pH and pHrodoTM emits a red fluorescence which intensity increased with acidification. Therefore, nanoparticles remained outside the cells could be clearly distinguished from nanoparticles uptaken by cells as these latter could be spotted inside cellular acidic compartments (such as phagolysosomes, micropinosomes...). Using this model, the endocytosis of 60 nm nanoparticles incubated with the RAW 264.7 macrophages was quantified using time-lapse microscopy and compared to that of 130 nm submicronic particles. The amount of internalized particles was also evaluated by fluorimetry. The biological impact of the particles was also investigated in terms of cytotoxicity, pro-inflammatory response and oxidative stress. Results clearly demonstrated that nanoparticles were more uptaken and more reactive than submicronic particles. Moreover, we validated a method of endocytosis quantification.

Published
2015

7. Respective importance of protein folding and glycosylation in the thermal stability of recombinant feruloyl esterase A

Author

Gerlind Sulzenbacher, Isabelle Gimbert, Eric Record, Laurence Marmuse, Christophe Bignon, Isabelle Benoit, Goetz Parsiegla, Michèle Asther, Marcel Asther, Unité mixte de recherche de biotechnologie des champignons filamenteux, Université de la Méditerranée - Aix-Marseille 2-Institut National de la Recherche Agronomique (INRA)-Université de Provence - Aix-Marseille 1, Architecture et fonction des macromolécules biologiques (AFMB), Centre National de la Recherche Scientifique (CNRS)-Aix Marseille Université (AMU)-Institut National de la Recherche Agronomique (INRA), Centre de Recherches sur les Macromolécules Végétales (CERMAV), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF), Institut National de la Recherche Agronomique (INRA)-Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), and Université Joseph Fourier - Grenoble 1 (UJF)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Models, Molecular, Protein Folding, Glycosylation, Protein Conformation, Crystallography, X-Ray, Biochemistry, Esterase, Inclusion bodies, law.invention, chemistry.chemical_compound, Structural Biology, Feruloyl esterase, law, Models, Catalytic Domain, Enzyme Stability, 0303 health sciences, Crystallography, biology, Circular Dichroism, Recombinant Proteins, THERMAL STABILITY, GLYCAN, Recombinant DNA, ESTERASE, Thermodynamics, Protein folding, lipids (amino acids, peptides, and proteins), Aspergillus niger, Glycan, animal structures, REFOLDING, Biophysics, [SDV.BC]Life Sciences [q-bio]/Cellular Biology, macromolecular substances, 03 medical and health sciences, Hydrolase, Genetics, Escherichia coli, Molecular Biology, Protein Processing, 030304 developmental biology, BIOCHIMIE, 030306 microbiology, Post-Translational, Structure, Molecular, Cell Biology, FERULOYL ESTERASE, carbohydrates (lipids), chemistry, biology.protein, X-Ray, Protein Processing, Post-Translational, Carboxylic Ester Hydrolases
Abstract

International audience; The thermal stability of four molecular forms (native, refolded, glycosylated, non-glycosylated) of feruloyl esterase A (FAEA) was studied. From the most to the least thermo-resistant, the four molecular species ranked as follows: (i) glycosylated form produced native, (ii) non-glycosylated form produced native, (iii) non-glycosylated form produced as inclusion bodies and refolded, and (iv) glycosylated form produced native chemically denatured and then refolded. On the basis of these results and of crystal structure data, we discuss the respective importance of protein folding and glycosylation in the thermal stability of recombinant FAEA.

Published
2006

8. Exploiting an aromatic aglycone as a reporter of glycosylation stereochemistry in the synthesis of 1,6-linked maltooligosaccharides

Author

Sergey A. Nepogodiev, Robert A. Field, and Laurence Marmuse

Subjects
Glycosylation, Chemistry, Stereochemistry, Organic Chemistry, Spectral dispersion, Acceptor, Catalysis, Inorganic Chemistry, chemistry.chemical_compound, Aglycone, Benzyl ether, Proton NMR, Stereoselectivity, Physical and Theoretical Chemistry
Abstract

Analysis of glycosylation stereoselectivity in the synthesis of branched maltooligosaccharides is hampered by poor spectral dispersion due to the repetitive nature of the saccharide chain and overlap of sugar H-1 signals with benzylic proton signals from the typically used benzyl ether protecting groups. A suitably protected p -methoxyphenyl maltoside acceptor, when coupled with benzylated maltooligosaccharide donors, gives discrete aglycone 1 H NMR signals that can be used to report on the stereoselectivity of 1,6-glycosylation reactions.

Published
2005

9. Lipo-chitin oligosaccharides, plant symbiosis signalling molecules that modulate Mammalian angiogenesis in vitro

Author

Peter M. Gresshoff, Michael A. Djordjevic, Susanti, Christopher R. Parish, Alison M. Daines, Farzaneh Kordbacheh, Laurence Marmuse, Ralf Schwörer, Boris Vauzeilles, Barry G. Rolfe, Eric Samain, Anna Bezos, Hugues Driguez, Jean-Marie Beau, Brunet, Jocelyne, Nano-H SAS, Centre de Recherches sur les Macromolécules Végétales (CERMAV), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
Lipopolysaccharides, Integrins, Angiogenesis, Acylation, lcsh:Medicine, Plant Science, Disaccharides, 0302 clinical medicine, Cell Movement, [CHIM] Chemical Sciences, Medicine and Health Sciences, lcsh:Science, Aorta, Mammals, 0303 health sciences, Multidisciplinary, biology, Pharmaceutics, Biological activity, Acetylation, Agriculture, Extracellular Matrix, Biochemistry, 030220 oncology & carcinogenesis, Signal transduction, Signal Transduction, Research Article, Biotechnology, Cell signaling, Integrin, Neovascularization, Physiologic, In Vitro Techniques, Microbiology, 03 medical and health sciences, Cell Adhesion, Animals, Humans, [CHIM]Chemical Sciences, Cell adhesion, Symbiosis, Molecular Biology, 030304 developmental biology, Innate immune system, lcsh:R, fungi, Endothelial Cells, Biology and Life Sciences, Cell Biology, In vitro, Rats, Inbred F344, biology.protein, lcsh:Q, Soybeans, Developmental Biology
Abstract

International audience; Lipochitin oligosaccharides (LCOs) are signaling molecules required by ecologically and agronomically important bacteria and fungi to establish symbioses with diverse land plants. In plants, oligo-chitins and LCOs can differentially interact with different lysin motif (LysM) receptors and affect innate immunity responses or symbiosis-related pathways. In animals, oligo-chitins also induce innate immunity and other physiological responses but LCO recognition has not been demonstrated. Here LCO and LCO-like compounds are shown to be biologically active in mammals in a structure dependent way through the modulation of angiogenesis, a tightly-regulated process involving the induction and growth of new blood vessels from existing vessels. The testing of 24 LCO, LCO-like or oligo-chitin compounds resulted in structure-dependent effects on angiogenesis in vitro leading to promotion, or inhibition or nil effects. Like plants, the mammalian LCO biological activity depended upon the presence and type of terminal substitutions. Un-substituted oligo-chitins of similar chain lengths were unable to modulate angiogenesis indicating that mammalian cells, like plant cells, can distinguish between LCOs and un-substituted oligo-chitins. The cellular mode-of-action of the biologically active LCOs in mammals was determined. The stimulation or inhibition of endothelial cell adhesion to vitronectin or fibronectin correlated with their pro- or anti-angiogenic activity. Importantly, novel and more easily synthesised LCO-like disaccharide molecules were also biologically active and de-acetylated chitobiose was shown to be the primary structural basis of recognition. Given this, simpler chitin disaccharides derivatives based on the structure of biologically active LCOs were synthesised and purified and these showed biological activity in mammalian cells. Since important chronic disease states are linked to either insufficient or excessive angiogenesis, LCO and LCO-like molecules may have the potential to be a new, carbohydrate-based class of therapeutics for modulating angiogenesis.

Published
2013

10. Oligonucleotide solid-phase synthesis on fluorescent silica particles of nanometric size

Author

Gabriel de Crozals, Carole Farre, Marquette, Christophe A., Mandon, Céline A., Matteo Martini, Jean-Jacques Toulmé, Darocha, S., Claire Billotey, Marc Janier, Laurence Marmuse, Cédric Louis, Carole Chaix, SIMS - Surfaces-(bio)Interfaces - Micro & Nano Systèmes, Institut des Sciences Analytiques ( ISA ), Centre National de la Recherche Scientifique ( CNRS ) -Université de Lyon-Université Claude Bernard Lyon 1 ( UCBL ), Université de Lyon-École normale supérieure - Lyon ( ENS Lyon ) -Centre National de la Recherche Scientifique ( CNRS ) -Université de Lyon-Université Claude Bernard Lyon 1 ( UCBL ), Université de Lyon-École normale supérieure - Lyon ( ENS Lyon ), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires ( ICBMS ), Université Claude Bernard Lyon 1 ( UCBL ), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon ( INSA Lyon ), Université de Lyon-Institut National des Sciences Appliquées ( INSA ) -Institut National des Sciences Appliquées ( INSA ) -École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique ( CNRS ), Laboratoire de Physico-Chimie des Matériaux Luminescents ( LPCML ), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique ( CNRS ), Imagerie Moléculaire et Nanobiotechnologies - Institut Européen de Chimie et Biologie ( IECB ), Université Sciences et Technologies - Bordeaux 1-Centre National de la Recherche Scientifique ( CNRS ), Nano-H SAS, Bussy, Agnès, SIMS - Surfaces-(bio)Interfaces - Micro & Nano Systèmes (2011-2014), Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Physico-Chimie des Matériaux Luminescents (LPCML), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon, Imagerie Moléculaire et Nanobiotechnologies - Institut Européen de Chimie et Biologie (IECB), and Université Sciences et Technologies - Bordeaux 1-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ANAL] Chemical Sciences/Analytical chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, [ CHIM.ANAL ] Chemical Sciences/Analytical chemistry
Published
2012

11. Oligonucleotide solid-phase synthesis on fluorescent nanoparticles grafted on controlled pore glass

Author

Carole Chaix, Carole Farre, Grégoire Hantier, Jean-Jacques Toulmé, Marc Janier, Claire Billotey, Didier Léonard, Christophe A. Marquette, Cédric Louis, Gabriel De Crozals, Laurence Marmuse, Céline A. Mandon, SIMS - Surfaces-(bio)Interfaces - Micro & Nano Systèmes, Institut des Sciences Analytiques ( ISA ), École normale supérieure - Lyon ( ENS Lyon ) -Université Claude Bernard Lyon 1 ( UCBL ), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique ( CNRS ) -École normale supérieure - Lyon ( ENS Lyon ) -Université Claude Bernard Lyon 1 ( UCBL ), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique ( CNRS ), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires ( ICBMS ), Université Claude Bernard Lyon 1 ( UCBL ), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon ( INSA Lyon ), Université de Lyon-Institut National des Sciences Appliquées ( INSA ) -Institut National des Sciences Appliquées ( INSA ) -École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique ( CNRS ), Nano-H SAS, Imagerie Moléculaire et Nanobiotechnologies - Institut Européen de Chimie et Biologie ( IECB ), Université Sciences et Technologies - Bordeaux 1-Centre National de la Recherche Scientifique ( CNRS ), Laboratoire de Physico-Chimie des Matériaux Luminescents ( LPCML ), ANR (ANR-08-Biotecs-003), LyonBiopole, Lyon Science Transfert, SIMS - Surfaces-(bio)Interfaces - Micro & Nano Systèmes (2011-2014), Institut des Sciences Analytiques (ISA), Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-École Supérieure Chimie Physique Électronique de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Imagerie Moléculaire et Nanobiotechnologies - Institut Européen de Chimie et Biologie (IECB), Université Sciences et Technologies - Bordeaux 1-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Physico-Chimie des Matériaux Luminescents (LPCML), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon

Subjects
Materials science, General Chemical Engineering, Nanoparticle, Nanotechnology, BIOANALYSIS, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Solid-phase synthesis, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, OXIDE NANOPARTICLES, Phosphoramidite, DNA synthesis, Oligonucleotide, General Chemistry, DNA, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Chemical engineering, chemistry, IMMOBILIZATION, Colloidal gold, GOLD NANOPARTICLES, Surface modification, FUNCTIONALIZATION, [ CHIM.ANAL ] Chemical Sciences/Analytical chemistry, 0210 nano-technology
Abstract

International audience; Oligonucleotide solid-phase synthesis is now possible on nano-sized particles, thanks to the use of controlled pore glass-nanoparticle assemblies. We succeeded in anchoring silica nanoparticles (NPs) inside the pores of micrometric glass via a reversible covalent binding. The pore diameter must be at least six times the diameter of the nanoparticle in order to maintain efficient synthesis of oligonucleotides in the synthesizer. We demonstrated that the pores protect NP anchoring during DNA synthesis without decreasing the coupling rate of the phosphoramidite synthons. This bottom-up strategy for NP functionalization with DNA results in unprecedented DNA loading efficiency. We also confirmed that the DNA synthesized on the nanoparticle surface was accessible for hybridization with its complementary DNA strand.

Published
2012

12. Biodistribution Study of Nanometric Hybrid Gadolinium Oxide Particles as a Multimodal SPECT/MR/Optical Imaging and Theragnostic Agent

Author

Claire Billotey, Pascal Perriat, Jacqueline Taleb, Imen Miladi, David Kryza, Marc Janier, Laurence Marmuse, Stéphane Roux, Olivier Tillement, Pauline Bonazza, Cédric Louis, Univers, Transport, Interfaces, Nanostructures, Atmosphère et environnement, Molécules (UMR 6213) (UTINAM), Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Franche-Comté (UFC), and Université Bourgogne Franche-Comté [COMUE] (UBFC)-Université Bourgogne Franche-Comté [COMUE] (UBFC)

Subjects
Biodistribution, Silicon, Fluorophore, Surface Properties, [SDV]Life Sciences [q-bio], Biomedical Engineering, Pharmaceutical Science, Nanoparticle, Bioengineering, Nanotechnology, Gadolinium, 02 engineering and technology, 010402 general chemistry, Kidney, 01 natural sciences, Fluorescence, chemistry.chemical_compound, medicine, Animals, Tissue Distribution, Particle Size, Rats, Wistar, ComputingMilieux_MISCELLANEOUS, Pharmacology, Tomography, Emission-Computed, Single-Photon, medicine.diagnostic_test, Organic Chemistry, Indium Radioisotopes, Kidney metabolism, Magnetic resonance imaging, 021001 nanoscience & nanotechnology, Magnetic Resonance Imaging, 0104 chemical sciences, Molecular Imaging, Rats, chemistry, Solubility, Nanoparticles, Tomography, Molecular imaging, 0210 nano-technology, Preclinical imaging, Biotechnology, Biomedical engineering
Abstract

Nanometric hybrid gadolinium oxide particles (Gado-6Si-NP) for diagnostic and therapeutic applications (mean diameter 3-4 nm) were obtained by encapsulating Gd(2)O(3) cores within a polysiloxane shell, which carries organic fluorophore (Cy 5) and is derivatized by a hydrophilic carboxylic layer. As residency time in the living body and methods of waste elimination are crucial to defining a good nanoparticle candidate and moving forward with steps for validation, this study was aimed at evaluating the biodistribution of these multimodal Gado-6Si-NP in rodents. Gado-6Si-NP were imaged following intravenous injection in control Wistar rats and mice using MRI (7 T), optical fluorescent imaging, and SPECT. A clear correlation was observed among MRI, optical imaging, and SPECT regarding the renal elimination. Quantitative biodistribution using gamma-counting of each sampled organ confirmed that these nanoparticles circulated freely in the blood pool and were rapidly cleared by renal excretion without accumulation in liver and RES uptake. These results demonstrate that Gado-6Si-NP display optimal biodistribution properties, enabling them to be developed as multimodal agents for in vivo imaging and theragnostics, especially in oncological applications.

Published
2011

13. Development of innovative pH sensor nanoparticles: a new approach to evaluate phagocytosis

Author

Lara Leclerc, Delphine Boudard, Jérémie POURCHEZ, Valérie Forest, Laurence Marmuse, Cédric Louis, Valérie Bin, Sabine Palle, Philippe Grosseau, Michèle Cottier, Laboratoire des Procédés en Milieux Granulaires (LPMG-EMSE), École des Mines de Saint-Étienne (Mines Saint-Étienne MSE), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-Centre National de la Recherche Scientifique (CNRS), Institut Fédératif de Recherche en Sciences et Ingénierie de la Santé (IFRESIS-ENSMSE), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-IFR143, Laboratoire Interdisciplinaire des Nanoparticules Aérosolisées (LINA-ENSME), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT), Service d'Histologie Embryologie, CHRU Saint-Etienne, R&D Laboratory, Nano-H, Biologie, Ingénierie et Imagerie de la Greffe de Cornée (EA 2521, JE2521, IFR143), Université Jean Monnet [Saint-Étienne] (UJM), Centre de Microscopie Confocale Multiphotonique (CMCM), Centre Sciences des Processus Industriels et Naturels (SPIN-ENSMSE), Département Poudres et Matériaux Multi-Composants (P2MC-ENSMSE), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-SPIN, Université Jean Monnet Saint Etienne, and Toucas, Andrée-Aimée

Subjects
[SDV.TOX] Life Sciences [q-bio]/Toxicology, [SPI.GPROC] Engineering Sciences [physics]/Chemical and Process Engineering, [SDV.TOX]Life Sciences [q-bio]/Toxicology, education, inhaled particles, toxicity, phagocytosis, pH sensor, [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering, alveolar macrophages, Fluorescent nanoparticles, confocal microscopy
Abstract

International audience; Macrophages (MA) from the respiratory tract constitute the first defense line against inhaled nanoparticles (NP) thanks to their phagocytic activity. The toxicity of NP mainly depends on their physicochemical characteristics (size, morphology, chemical surface groups...). However the relationship between the number of phagocytosed NP and their cellular activity is still unclear. In this context the accurate quantification of internalized NP by macrophages could allow a better assessment of NP toxicity and uptake mechanisms. The investigation of a relationship between NP internalization, physicochemical parameters and the degree of toxicity represents a crucial issue.

Published
2011

14. New chromogenic substrates for feruloyl esterases

Author

David Navarro, Laurence Lesage-Meessen, Michèle Asther, Emeline Fabre, Hugues Driguez, Michael J. O’Donohue, Marcel Asther, Laurence Marmuse, Sébastien Fort, Centre de Recherches sur les Macromolecules Vegetales, Unité mixte de recherche de biotechnologie des champignons filamenteux, Université de la Méditerranée - Aix-Marseille 2-Institut National de la Recherche Agronomique (INRA)-Université de Provence - Aix-Marseille 1, Laboratoire d'Ingénierie des Systèmes Biologiques et des Procédés (LISBP), Institut National de la Recherche Agronomique (INRA)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), ADEME: 0401C0042, ANR PNRB2005- 11, and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Chromatography, Molecular Structure, 010405 organic chemistry, Chromogenic, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Chromogenic Substrates, Substrate (chemistry), 010402 general chemistry, 01 natural sciences, Biochemistry, Feruloyl esterase activity, Solid medium, 0104 chemical sciences, Nitrophenols, Chromogenic Compounds, Molecular Probes, Physical and Theoretical Chemistry, Carboxylic Ester Hydrolases
Abstract

International audience; Indolyl and nitrophenyl 5-O-hydroxycinnamoyl-α-L-arabinofuranosides were prepared by chemo-enzymatic syntheses. These probes were designed as substrates to be used in assays of feruloyl esterase activity (EC 3.1.1.77). Color development in the assays only occurs when feruloyl esterase activity releases an intermediate chromogenic arabinoside that is a suitable substrate for α-L-arabinofuranosidase (EC 3.2.1.55), which in turn releases the free chromogenic group. The usefulness of these compounds was evaluated in both qualitative solid media-based assays and quantitative liquid assays that can be performed in microtiter plates using feruloyl esterases and arabinofuranosidases from various origins.

Published
2008

15. Chromogenic substrates for feruloyl esterases

Author

Laurence Marmuse, David Navarro, Marcel Asther, Sébastien Fort, Laurence Lesage-Meessen, Michèle Asther, Hugues Driguez, Centre de Recherches sur les Macromolécules Végétales, Centre National de la Recherche Scientifique (CNRS), Unité mixte de recherche de biotechnologie des champignons filamenteux, and Université de la Méditerranée - Aix-Marseille 2-Institut National de la Recherche Agronomique (INRA)-Université de Provence - Aix-Marseille 1

Subjects
Magnetic Resonance Spectroscopy, Time Factors, CHROMOGENIC SUBSTRATE, Chromogenic Substrates, education, 01 natural sciences, Biochemistry, Substrate Specificity, Analytical Chemistry, Nitrophenols, 03 medical and health sciences, Feruloyl esterase, parasitic diseases, Animals, 030304 developmental biology, 0303 health sciences, biology, BIOCHIMIE, ASPERGILLUS NIGER, 010405 organic chemistry, Chemistry, Chromogenic, Hydrolysis, fungi, Organic Chemistry, Aspergillus niger, Serum Albumin, Bovine, General Medicine, FERULOYL ESTERASE, biology.organism_classification, 0104 chemical sciences, Kinetics, [CHIM.POLY]Chemical Sciences/Polymers, Chromogenic Compounds, Models, Chemical, Cattle, Chromatography, Thin Layer, Carboxylic Ester Hydrolases, Protein Binding
Abstract

International audience; Chromogenic mono- and diferuloyl-butanetriol analogs were prepared by chemical syntheses and their efficiency was evaluated as substrates for feruloyl esterases from Aspergillus niger

Published
2007

16. Synthesis of triazole-linked pseudo-starch fragments

Author

Laurence Marmuse, Marcelo T. de Oliveira, Sergey A. Nepogodiev, Simone Dedola, and Robert A. Field

Subjects
Stereochemistry, Starch, Organic Chemistry, Amylopectin, Molecular Sequence Data, Triazole, Oligosaccharides, General Medicine, Maltose, Triazoles, Biochemistry, Cycloaddition, Analytical Chemistry, chemistry.chemical_compound, chemistry, Carbohydrate Sequence, Click chemistry
Abstract

Rapid assembly of starch fragment analogues was achieved using ‘click chemistry’. Specifically, a pentadecasaccharide and two hexadecasaccharide mimics containing two parallel maltoheptaosyl chains linked via [1,2,3]-triazoles to glucose or maltose core were synthesised using Cu(I)-catalyzed [3+2] dipolar cycloaddition of azidosaccharides and 4,6-di- O -propargylated methyl α- d -glucopyranoside and 6,6′- and 4′,6′-di- O -propargylated p -methoxyphenyl β-maltoside.

Published
2006

17. Development of innovative pH sensor to evaluate phagocytosis of nanoparticles

Author

Delphine Boudard, Philippe Grosseau, Cédric Louis, Sabine Palle, Jérémie Pourchez, D. Bernache, Laurence Marmuse, Lara Leclerc, and Michèle Cottier

Subjects
Ph probe, History, Chromatography, Chemistry, Phagocytosis, Nanoparticle, Macrophage cell, Fluorescence, Computer Science Applications, Education, Red fluorescence
Abstract

The aim of this work was the development of pH-sensor-NP allowing the quantification of the amount of NP phagocytosed by macrophages. Two types of fluorescent NP with variable and well-characterized sizes and chemicals coatings have been synthesized: NP with a FITC core (FITC-NP): green fluorescence (control). FITC-NP functionalized with a pH sensitive probe (pH-sensor-NP): green fluorescence of the FITC and red fluorescence of the pH probe in acidic conditions. Our pH-sensor-NP model was first validated in acellular conditions. They were then incubated with a macrophage cell line allowing distinction and quantification of internalized NP with no major effects on biological toxicity.

Published
2011

18. 'Click chemistry'en route to pseudo-starch

Author

Laurence Marmuse, Robert A. Field, and Sergey A. Nepogodiev

Subjects
Magnetic Resonance Spectroscopy, Starch, Molecular Sequence Data, Organic Chemistry, Nuclear magnetic resonance spectroscopy, Maltose, Biochemistry, Combinatorial chemistry, Cycloaddition, chemistry.chemical_compound, Carbohydrate Sequence, chemistry, Click chemistry, Physical and Theoretical Chemistry
Abstract

Rapid assembly of starch fragment analogues was achieved using "click chemistry". Specifically, two hexadecasaccharide mimics containing two parallel maltoheptaosyl chains linked via [1,2,3]-triazoles to a maltose core were synthesized using Cu(i)-catalyzed [3 + 2] dipolar cycloaddition of azido saccharides and 6,6'- and 4',6'-dipropargylated p-methoxyphenyl maltoside.

Published
2005

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