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1. Ring-Opening of Cyclodextrins: An Efficient Route to Pure Maltohexa-, Hepta-, and Octaoses

Author

Matthieu Pélingre, Dindet Steve-Evanes Koffi Teki, Jamal El-Abid, Vincent Chagnault, José Kovensky, and Véronique Bonnet

Subjects
cyclodextrins, maltooligosaccharides, building blocks, platform molecules, monomers, Organic chemistry, QD241-441
Abstract

Many preparations of maltooligosaccharides have been described in literature, essentially using enzymatic or biotechnological processes. These compounds, derived from starch, are well-known as prebiotic agents. The use of maltohexa-, hepta-, and octaoses as synthons in organic synthesis was also well documented in literature. They can indeed be obtained as single compounds by the cyclodextrins’ ring-opening. This reaction has been studied for many years, varying the protecting and functional groups and the reaction conditions, leading to functionalized oligomaltoses. These compounds are of wide interest in various fields. They have a strong potential as scaffolds for multivalence in chemobiology, as building blocks for the production of biomimetic pseudo-glycopeptides, as well as monomers for the preparation of materials. In view of the importance of these oligomaltoses, this review focuses on the different methodologies allowing access to them via chemical and enzymatic ring-opening of cyclodextrins.

Published
2021
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2. 'Frères migrantes', de Patrick Chamoiseau : l'intention humaniste

Author

Véronique Bonnet, Henrique Provinzano Amaral, and Thiago Mattos de Oliveira

Subjects
Literature (General), PN1-6790
Abstract

Cet article examine comment, à partir du drame des migrants qui font route vers l’Europe, Frères migrants de Patrick Chamoiseau suggère la possibilité d’un « humanisme à la mesure du monde » (CÉSAIRE, 1973). L’essai manifeste une intention humaniste, sous la forme d’une bibliothèque intertextuelle qui perpétue tout à la fois la pensée de l’humanisme et l’esprit de la « sentimenthèque » figurant dans Écrire en pays dominé (CHAMOISEAU, 1997). Si le traitement inhumain infligé aux migrants dévoile les angles morts de l’humanisme européen et rappelle les méthodes coloniales, la prise en compte fraternelle de ces derniers invite à repenser et à élargir l’humanisme. La médiatisation de l’essai se prolonge par la publication d’un recueil collectif Osons la fraternité ! Les écrivains aux côtés des migrants (CHAMOISEAU, LE BRIS, 2018) au sein duquel certains textes questionnent les apories de toute intention humaniste.

Published
2022

3. Characterization of Grapevine Fanleaf Virus Isolates in ‘Chardonnay’ Vines Exhibiting Severe and Mild Symptoms in Two Vineyards

Author

Julie Kubina, Jean-Michel Hily, Pierre Mustin, Véronique Komar, Shahinez Garcia, Isabelle Rachel Martin, Nils Poulicard, Amandine Velt, Véronique Bonnet, Laurence Mercier, Olivier Lemaire, and Emmanuelle Vigne

Subjects
grapevine fanleaf virus, fanleaf degeneration, grapevine, symptomatology, mild isolates, cross-protection, Microbiology, QR1-502
Abstract

Fanleaf degeneration is a complex viral disease of Vitis spp. that detrimentally impacts fruit yield and reduces the productive lifespan of most vineyards worldwide. In France, its main causal agent is grapevine fanleaf virus (GFLV). In the past, field experiments were conducted to explore cross-protection as a management strategy of fanleaf degeneration, but results were unsatisfactory because the mild virus strain negatively impacted fruit yield. In order to select new mild GFLV isolates, we examined two old ‘Chardonnay’ parcels harbouring vines with distinct phenotypes. Symptoms and agronomic performances were monitored over the four-year study on 21 individual vines that were classified into three categories: asymptomatic GFLV-free vines, GFLV-infected vines severely diseased and GFLV-infected vines displaying mild symptoms. The complete coding genomic sequences of GFLV isolates in infected vines was determined by high-throughput sequencing. Most grapevines were infected with multiple genetically divergent variants. While no specific molecular features were apparent for GFLV isolates from vines displaying mild symptoms, a genetic differentiation of GFLV populations depending on the vineyard parcel was observed. The mild symptomatic grapevines identified during this study were established in a greenhouse to recover GFLV variants of potential interest for cross-protection studies.

Published
2022
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6. New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

Author

Estefania Oliva, David Mathiron, Sébastien Rigaud, Eric Monflier, Emmanuel Sevin, Hervé Bricout, Sébastien Tilloy, Fabien Gosselet, Laurence Fenart, Véronique Bonnet, Serge Pilard, and Florence Djedaini-Pilard

Subjects
host-guest chemistry, cyclodextrin, sustainability, ball milling, mass spectrometry, Microbiology, QR1-502
Abstract

Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions, use of enzymes). The ring opening reaction of methyl oleate epoxide needs ball-milling and is highly specific of cyclodextrins in solventless conditions. L-CDs are thus composed of complex mixtures that were deciphered by an extensive structural analysis using mainly mass spectrometry and NMR spectroscopy. In addition, as part of their potential use as vectors of active drugs, these products were submitted to an integrity study on in vitro model of the blood-brain-barrier (BBB) and the intestinal epithelium. No toxicity has been observed, suggesting that applications for the vectorization of active ingredients can be expected.

Published
2020
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7. La littérature de la Caraïbe pour la jeunesse : des histoires à part ou l’histoire à part entière ?

Author

Véronique Bonnet

Subjects
Caribbean youth literature, writing of history, exil, memory., Anthropology, GN1-890, History of Civilization, CB3-482
Abstract

Children’s literature produced by writers born in the Caribbean is prolific. However, it still remains less known than the stories of Franco-Algerians and has drawn less attention from specialists. As all West Indian literary productions, it grants a significant place to the writing of history: whether it is the memory of slavery or of immediate history (news item, conflicts, stories of immigration). As a major witness the young subject confronts the history, which forges his personal development and place in the world. For the younger generation, the analysis of the texts of three important writers – Maryse Conde, Gisèle Pineau and Dany Laferrière – helps to show how undocumented parts of the history, little or badly known, fit in well in Francophone literature and thus become objects of questioning and knowledge. Maryse Condé considers history as a political rebus which can be deciphered from a militant perspective. In an ethico-political way, its protagonists question the recent conflicts, the sinuosities of history, and thus learn what textbooks conceal. Gisèle Pineau’s stories unveil what C. Pinconnat calls the « endofiction ». For instance, the history of West Indian immigration in France, personally experienced by the author, is told with its wrench, ambiguities and horizon of reconciliation, among which the Caribbean space and the maintaining of the island memory. The texts Dany Laferrière dedicates to youth are made up by part of his earlier work, which is rewritten and extended. They create a personal mythology which sets himself and Haiti at the center of the story in depicting political exile and continual literary returns to the native island. The stories of the three authors ultimately suggest an interconnection between the (young) reader and the history in which he acquires his own place through the sharing of knowledge.

Published
2017
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8. Cyclodextrin-grafted polymers functionalized with phosphanes: a new tool for aqueous organometallic catalysis

Author

Jonathan Potier, Stéphane Menuel, David Mathiron, Véronique Bonnet, Frédéric Hapiot, and Eric Monflier

Subjects
biphasic catalysis, cyclodextrin, hydroformylation, phosphane, polymer, Science, Organic chemistry, QD241-441
Abstract

New cyclodextrin (CD)-grafted polymers functionalized with water-soluble phosphanes were synthesized in three steps starting from polyNAS. Once characterized by NMR spectroscopy and size-exclusion chromatography, they were used as additives in Rh-catalyzed hydroformylation of 1-hexadecene. The combined supramolecular and coordinating properties of these polymers allowed increasing the catalytic activity of the reaction without affecting the selectivities.

Published
2014
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9. A green approach to the synthesis of novel phytosphingolipidyl β-cyclodextrin designed to interact with membranes

Author

Yong Miao, Florence Djedaïni-Pilard, and Véronique Bonnet

Subjects
fatty ester, green chemistry, lipase, mono-substituted amphiphilic cyclodextrins, peptide Coupling, solvent-free medium, transesterification, Science, Organic chemistry, QD241-441
Abstract

This work reports the synthesis of a new family of mono-substituted amphiphilic cyclodextrins using a green methodology. Reactions using greener and safer catalysts with more environmentally friendly purification solvents were performed. Four unreported mono-substituted cyclodextrins bearing a phytosphingolipidyl chain and a fatty acid chain (C10, C12, C14 and C18) were successfully obtained with a promising yield.

Published
2014
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10. Introduction

Author

Véronique Bonnet, Marc Kober, and Khalid Zekri

Subjects
Language and Literature
Published
2012

11. La Vida perra de Juanita Narboni de Farida ­Benlyazid : une réécriture filmique postcoloniale ?

Author

Véronique Bonnet

Subjects
Tangier, cinema, rewriting, monologue, Second World War, post­colonialism, Language and Literature
Abstract

The film rewriting of Ángel Vázquez’s literary work by the Moroccan film director, Farida Benlyazid, makes of Tangier one of the driving elements of the film. In reconfiguring the monologue of the main character, Juanita Narboni, the film-maker incorporates in her movie memories of her childhood and acutely examines the history of the Second World War in Tangier. The comparative analysis of the novel and the film points out the singularity of each work and, more specifically, allows understanding how aesthetically and ideologically the film director proposes a different perception of the reality of the subordinates and introduces a postcolonial thought.

Published
2012
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12. Molecular and functional analysis of two new MTTP gene mutations in an atypical case of abetalipoproteinemia

Author

Mathilde Di Filippo, Hervé Créhalet, Marie Elisabeth Samson-Bouma, Véronique Bonnet, Lawrence P. Aggerbeck, Jean-Pierre Rabès, Frederic Gottrand, Gérald Luc, Dominique Bozon, and Agnès Sassolas

Subjects
dyslipidemias, familial hypocholesterolemia, chylomicrons, lipoprotein/assembly, hepatosteatosis, genetics, Biochemistry, QD415-436
Abstract

Abetalipoproteinemia (ABL) is an inherited disease characterized by the defective assembly and secretion of apolipoprotein B–containing lipoproteins caused by mutations in the microsomal triglyceride transfer protein large subunit (MTP) gene (MTTP). We report here a female patient with an unusual clinical and biochemical ABL phenotype. She presented with severe liver injury, low levels of LDL-cholesterol, and subnormal levels of vitamin E, but only mild fat malabsorption and no retinitis pigmentosa or acanthocytosis. Our objective was to search for MTTP mutations and to determine the relationship between the genotype and this particular phenotype. The subject exhibited compound heterozygosity for two novel MTTP mutations: one missense mutation (p.Leu435His) and an intronic deletion (c.619-5_619-2del). COS-1 cells expressing the missense mutant protein exhibited negligible levels of MTP activity. In contrast, the minigene splicing reporter assay showed an incomplete splicing defect of the intronic deletion, with 26% of the normal splicing being maintained in the transfected HeLa cells. The small amount of MTP activity resulting from the residual normal splicing in the patient explains the atypical phenotype observed. Our investigation provides an example of a functional analysis of unclassified variations, which is an absolute necessity for the molecular diagnosis of atypical ABL cases.

Published
2012
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13. Introduction

Author

Véronique Bonnet, Guillaume Bridet, and Yolaine Parisot

Subjects
Language and Literature
Published
2009

14. Combined use of in silico and in vitro splicing assays for interpretation of genomic variants of unknown significance in cardiomyopathies and channelopathies

Author

Hervé Crehalet, Gilles Millat, Juliette Albuisson, Véronique Bonnet, Isabelle Rouvet, Robert Rousson, and Dominique Bozon

Subjects
cardiomyopathies, arrhythmia syndromes, splice mutations, molecular diagnosis., Diseases of the circulatory (Cardiovascular) system, RC666-701
Abstract

The identification of molecular anomalies in patients with inherited arrhythmias or cardiomyopathies is a multi challenge due to: i) the number of genes involved; ii) the number of polymorphisms and the fact that most mutations are private; and iii) the variable degree of penetrance which complicates family segregation study. Consequently, a number of unclassified variants (UV) are found in patients’ DNA and some (outside the canonical GT/AG) may affect splicing. Mutational screening on the most prevalent genes involved in arrythmias syndromes or in cardiomyopathies was performed on a cohort made up of 740 unrelated French index probands. To identify splice variants among the identified UVs, a combination of available in silico and in vitro tools were used since transcript is not available. Using this approach, 10 previously identified UVs were reclassified as disease-causing mutations and, more precisely, as haploinsufficiency mutations rather than dominant-negative mutations. Most of them (7 of 10) were observed in MYBPC3. Our study highlighted the importance of the combined use of in silico and in vitro splicing assays to improve the prediction of the functional impact of identified genetic variants. The primary challenge now, with new sequencing technologies, is to distinguish between background polymorphisms and pathogenic mutations. Since splice site mutations can account for almost 50% of disease-causing mutations, recognizing them from among other variations is essential.

Published
2012
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20. The formulation of a CMC binder/silicon composite anode for Li-ion batteries: from molecular effects of ball milling on polymer chains to consequences on electrochemical performances

Author

Mariama Ndour, Jean-Pierre Bonnet, Sébastien Cavalaglio, Tristan Lombard, Matthieu Courty, Luc Aymard, Cédric Przybylski, Véronique Bonnet, Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire réactivité et chimie des solides - UMR CNRS 7314 (LRCS), Réseau sur le stockage électrochimique de l'énergie (RS2E), Université de Nantes (UN)-Aix Marseille Université (AMU)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Université de Picardie Jules Verne (UPJV)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP ), Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA), Laboratoire des technologies de la microélectronique (LTM ), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes (UGA), Commissariat à l'énergie atomique et aux énergies alternatives - Laboratoire d'Electronique et de Technologie de l'Information (CEA-LETI), Direction de Recherche Technologique (CEA) (DRT (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Université de Picardie Jules Verne (UPJV)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP ), Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA)-Nantes Université (Nantes Univ)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), and Université de Montpellier (UM)

Subjects
Chemistry (miscellaneous), [CHIM]Chemical Sciences, General Materials Science
Abstract

The semi-synthetic polysaccharide carboxymethylcellulose (CMC) is one of the most studied and effective polymer binders for silicon-based anodes in Li-ion batteries.

Published
2022

21. Ring-Opening of Cyclodextrins: An Efficient Route to Pure Maltohexa-, Hepta-, and Octaoses

Author

José Kovensky, Dindet Steve-Evanes Koffi Teki, Matthieu Pélingre, Véronique Bonnet, Jamal El-Abid, and Vincent Chagnault

Subjects
Reaction conditions, cyclodextrins, platform molecules, Starch, Synthon, maltooligosaccharides, Organic chemistry, Ring (chemistry), monomers, Combinatorial chemistry, Biotechnological process, building blocks, chemistry.chemical_compound, Monomer, QD241-441, chemistry, Organic synthesis
Abstract

Many preparations of maltooligosaccharides have been described in literature, essentially using enzymatic or biotechnological processes. These compounds, derived from starch, are well-known as prebiotic agents. The use of maltohexa-, hepta-, and octaoses as synthons in organic synthesis was also well documented in literature. They can indeed be obtained as single compounds by the cyclodextrins’ ring-opening. This reaction has been studied for many years, varying the protecting and functional groups and the reaction conditions, leading to functionalized oligomaltoses. These compounds are of wide interest in various fields. They have a strong potential as scaffolds for multivalence in chemobiology, as building blocks for the production of biomimetic pseudo-glycopeptides, as well as monomers for the preparation of materials. In view of the importance of these oligomaltoses, this review focuses on the different methodologies allowing access to them via chemical and enzymatic ring-opening of cyclodextrins.

Published
2021

22. One‐Pot Synthesis of Asymmetrically Difunctionalized Oligomaltosides by Cyclodextrin Ring Opening

Author

Meriem Smadhi, José Kovensky, Abed Bil, Véronique Bonnet, and Matthieu Pélingre

Subjects
Allylation, One-pot synthesis, Cyclodextrin ring-opening, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Medicinal chemistry, Chemical reaction, chemistry.chemical_compound, Azidation, Functionalization, QD1-999, chemistry.chemical_classification, Cyclodextrin, 010405 organic chemistry, Communication, Propargylation, General Chemistry, HEXA, Communications, 0104 chemical sciences, Chemistry, chemistry, Propargyl, Surface modification, Oligomaltosides synthesis, Azide
Abstract

The synthesis of pure difunctionalized hexa‐, hepta‐ and octamaltosides was performed by one‐pot chemical reaction from perbenzoylated cyclodextrin. Oligomaltosides with azide, propargyl or allyl on reducing end and an unprotected hydroxyl group on non‐reducing end were obtained from perbenzoylated α‐, β‐ and γ‐cyclodextrin with 12 to 48 % yields., This innovative synthesis reaction is a one‐pot opening of the α‐, β‐ or γ‐cyclodextrin allowing oligomaltosides with functionalization of the reducing end and unprotected non‐reducing end.

Published
2021

24. Further Insight into the Detailed Characterization of a Polydisperse Cyclodextrin-Based Polyrotaxane Sample by Electrospray Ionization Mass Spectrometry

Author

Nathalie Jarroux, Cédric Przybylski, and Véronique Bonnet

Subjects
chemistry.chemical_classification, Polymers and Plastics, Cyclodextrin, Silylation, Electrospray mass spectrometry, Electrospray ionization, Organic Chemistry, Dispersity, Analytical chemistry, Supramolecular chemistry, Polyrotaxane, Characterization (materials science), Inorganic Chemistry, chemistry, Materials Chemistry
Abstract

An easy and fast approach based on electrospray mass spectrometry (ESI-MS) was developed to provide a detailed characterization of a mixture containing polydisperse cyclodextrin-based polyrotaxane (CD-based PR). Here, method gave access to usual data such the weight-average molecular weight, the number-average molecular weight and the polydispersity index, but also to more specific features as the average number of CDs threaded and the average threading degree. Moreover, the nature and the average number of groups grafted per CD, such as sulfate or silyl groups, can be accurately determinate. This ESI-MS approach advantageously complements the widely used NMR and SEC methods and, thereby, constituting a milestone in the actual MS bottleneck regarding the analysis of polydisperse supramolecular assemblies.

Published
2022

26. Probing topology of supramolecular complexes between cyclodextrins and alkali metals by ion mobility-mass spectrometry

Author

Cédric, Przybylski and Véronique, Bonnet

Subjects
Cyclodextrins, Polymers and Plastics, Metals, Alkali, Ammonium Compounds, Organic Chemistry, Materials Chemistry, Protons, Mass Spectrometry
Abstract

In this study, the size and shape of supramolecular assemblies between cyclo-oligosaccharides and proton, ammonium or a series of alkali metals by electrospray coupled to trapped ion mobility-mass spectrometry (ESI-TIMS) have investigated. Native cyclodextrins (CD) were selected as models, and collision cross section (CCS) values were deducted for the main positive singly and doubly charged species. Experimental CCS values were in good agreement with those obtained from molecular modeling. Due to the high mobility resolving power and resolution, it was possible to highlight the presence of various conformers. Also, TIMS allowed to discriminate and estimate the content of various orientations from non-covalent nanotubes-based CD, involving secondary/secondary rim hydroxyl groups (head-to head), primary/secondary rim (head-to-tail) hydroxyl groups or primary/primary rim (tail-to-tail) hydroxyl groups interactions. Such results pave the way for a better knowledge of the topology of cyclo-oligosaccharides based supramolecular complexes, demonstrating that TIMS can be a particularly attractive molecular descriptor.

Published
2022

29. Highly Water-Soluble Amphiphilic Cyclodextrins Bearing Branched and Cyclic Oleic Grafts

Author

Cyril Rousseau, Aurélien Cocq, Sébastien Tilloy, Hervé Bricout, Florence Djedaïni-Pilard, Véronique Bonnet, Eric Monflier, and Estefanía Oliva

Subjects
Bearing (mechanical), 010405 organic chemistry, Organic Chemistry, Succinic anhydride, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Rhodium, law.invention, Oleic acid, chemistry.chemical_compound, Water soluble, chemistry, law, Amphiphile, Organic chemistry, Physical and Theoretical Chemistry
Published
2019

30. Oleic Acid Based Cyclodextrins for the Development of New Hydrosoluble Amphiphilic Compounds

Author

Hervé Bricout, Véronique Bonnet, Estefanía Oliva, Aurélien Cocq, Eric Monflier, Sébastien Tilloy, Cyril Rousseau, and Florence Djedaïni-Pilard

Subjects
chemistry.chemical_classification, Cyclodextrin, 010405 organic chemistry, Organic Chemistry, Succinic anhydride, Maleic anhydride, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Oleic acid, chemistry, Amphiphile, Organic chemistry, Physical and Theoretical Chemistry
Published
2019

31. Atlântico Sul na Literatura

Author

Vanessa Massoni da Rocha, Claudia Amigo Pino, and Véronique Bonnet

Subjects
General Medicine
Published
2018

32. Discrimination of isomeric trisaccharides and their relative quantification in honeys using trapped ion mobility spectrometry

Author

Véronique Bonnet, Cédric Przybylski, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), and Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
ion-mobility, Anomer, Resolution (mass spectrometry), Ion-mobility spectrometry, Absolute quantification, Electrospray ionization, Carbohydrates, 01 natural sciences, Analytical Chemistry, 0404 agricultural biotechnology, Isomerism, Ion Mobility Spectrometry, Structural isomer, Monosaccharide, [CHIM]Chemical Sciences, chemistry.chemical_classification, Chromatography, cross section, Chemistry, 010401 analytical chemistry, Stereoisomerism, Glycosidic bond, 04 agricultural and veterinary sciences, General Medicine, Honey, ESI-TIMS Collision, 040401 food science, 0104 chemical sciences, Trisaccharides, Food Analysis, Food Science
Abstract

International audience; Carbohydrates play a myriad of critical roles as key intermediaries for energy storage, cell wall constituents, or also fuel for organisms. The deciphering of multiple structural isomers based on the monosaccharides composition (stereoisomers), the type of glycosidic linkages (connectivity) and the anomeric configuration (α and β), remains a major analytical challenging task. The possibility to discriminate 13 underivatized isomeric trisaccharides were reported using electrospray ionization coupled to trapped ion mobility spectrometry (ESI-TIMS). After optimization of scan ratio enhancing both the mobility resolving power (R) and resolution (r), fingerprints from 5 different honeys were obtained. Seven trisaccharides with relative content varying from 1.5 to 58.3%, were identified. It was demonstrated that their relative content and/or their ratio could be used to ascertain origin of the honeys. Moreover, such direct approach constitutes an alternative tool to current longer chromatographic runs, paving the way to a transfer as suitable routine analysis.

Published
2021

34. First Steps to Rationalize Host–Guest Interaction between α-, β-, and γ-Cyclodextrin and Divalent First-Row Transition and Post-transition Metals (Subgroups VIIB, VIIIB, and IIB)

Author

Cédric Przybylski, Anne Ponchel, Teddy Weisgerber, Lucas Fontaine, Véronique Bonnet, Héloïse Dossmann, Eric Monflier, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), UCCS Équipe Catalyse Supramoléculaire, Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Ecole Centrale de Lille-Université d'Artois (UA)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Ecole Centrale de Lille-Université d'Artois (UA), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), and Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille

Subjects
Models, Molecular, Spectrometry, Mass, Electrospray Ionization, Spin states, Binding energy, Molecular Conformation, Supramolecular chemistry, [CHIM.INOR]Chemical Sciences/Inorganic chemistry, 010402 general chemistry, 01 natural sciences, Inorganic Chemistry, Transition metal, Coordination Complexes, Tandem Mass Spectrometry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Transition Elements, Molecule, [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, Density Functional Theory, Cyclodextrins, 010405 organic chemistry, Chemistry, Bond-dissociation energy, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Bond length, Crystallography, Natural bond orbital
Abstract

International audience; Cyclodextrins (CDs) are cyclic oligosaccharides mainly composed of six, seven, and eight glucose units, so-called α-, β-, and γ-CDs, respectively. They own a very particular molecular structure exhibiting hydrophilic features thanks to primary and secondary rims and delimiting a hydrophobic internal cavity. The latter can encapsulate organic compounds, but the former can form supramolecular complexes by hydrogen-bonding or electrostatic interactions. CDs have been used in catalytic processes to increase mass transfer in aqueous–organic two-phase systems or to prepare catalysts. In the last case, interaction between CDs and metal salts was considered to be a key point in obtaining highly active catalysts. Up to now, no work was reported on the investigation of factors affecting the binding of metal to CD. In the study herein, we present the favorable combination of electrospray ionization coupled to mass spectrometry [ESI-MS(/MS)] and density functional theory molecular modeling [B3LYP/Def2-SV(P)] to delineate some determinants governing the coordination of first-row divalent transition metals (Mn2+, Co2+, Ni2+, Cu2+, and Fe2+) and one post-transition metal (Zn2+) with α-, β-, and γ-CDs. A large set of features concerning the metal itself (ionic radius, electron configuration, and spin state) as well as the complexes formed (the most stable conformer, relative abundance in MS, CE50 value in MS/MS, binding energy, effective coordination number, average bond lengths, binding site localization, bond dissociation energies, and natural bond orbital distribution) were screened. Taking into account all of these properties, various selectivity rankings have been delineated, portraying differential association/dissociation behaviors. Nonetheless, unique 3D topologies for each CD–metal complex were emphasized. The combination of these approaches brings a stone for building a compendium of molecular features to serve as a suitable descriptor or predictor for a better first round rationalization of catalytic activities.

Published
2021

35. L'Antre-Temps : D'une éclosion à l'autre

Author

Véronique Bonnet and Véronique Bonnet

Abstract

Une femme aux paysages variés cherche à habiter sa vie. Peu à peu, elle y parvient… Sur son chemin vers une pleine existence, une date fondatrice, le 14 octobre 2013 et la découverte de l'écriture – à moins qu'il ne s'agisse de retrouvailles? Un présent reconquis de haute lutte, vécu les yeux ouverts, se déploie sur un passé et une geste familiale que les voix de l'enfance et des anciens font ressurgir. Dans une forme aussi éclatée que rigoureuse, l'auteure nous invite, à travers un savant maillage, à explorer la spirale d'une vie et à en construire le sens. Suite au deuil de sa Marraine, Livia revoit l'histoire de sa famille, depuis le retour d'Algérie. En écrivant, elle revisite son propre chemin avec un autre regard : son enfance dans le Bordelais et le Poitou, des épisodes de sa vie de femme, sa pratique de médecin et ses débuts comme thérapeute. C'est un nouveau sens qui apparait : celui de la gratitude et de l'apaisement par la magie du lien humain.

Published
2023

36. New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

Author

Eric Monflier, Véronique Bonnet, Sébastien Tilloy, Laurence Fenart, Fabien Gosselet, Estefanía Oliva, David Mathiron, Florence Djedaïni-Pilard, Hervé Bricout, Emmanuel Sevin, Serge Pilard, Sébastien Rigaud, Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Plateforme Analytique (PFA), Université de Picardie Jules Verne (UPJV), UCCS Équipe Catalyse Supramoléculaire, Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille-Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille, Laboratoire de la Barrière Hémato-Encéphalique (LBHE), Université d'Artois (UA), Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), CNRS, Centrale Lille, ENSCL, Univ. Artois, Université de Lille, Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 [LG2A ], Université de Picardie Jules Verne [UPJV], Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181, Laboratoire de Physiopathologie de la Barrière Hémato-Encéphalique [LBHE], and Laboratoire de la Barrière Hémato-Encéphalique [LBHE]

Subjects
Magnetic Resonance Spectroscopy, lcsh:QR1-502, Epoxide, Oleic Acids, Context (language use), 010402 general chemistry, Ring (chemistry), Mass spectrometry, 01 natural sciences, Biochemistry, Article, lcsh:Microbiology, chemistry.chemical_compound, Organic chemistry, [CHIM]Chemical Sciences, host-guest chemistry, Host–guest chemistry, Molecular Biology, ComputingMilieux_MISCELLANEOUS, mass spectrometry, Active ingredient, chemistry.chemical_classification, Cyclodextrins, Cyclodextrin, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, technology, industry, and agriculture, Esters, Nuclear magnetic resonance spectroscopy, sustainability, 0104 chemical sciences, chemistry, cyclodextrin, Epoxy Compounds, ball milling
Abstract

International audience; Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions, use of enzymes). The ring opening reaction of methyl oleate epoxide needs ball-milling and is highly specific of cyclodextrins in solventless conditions. L-CDs are thus composed of complex mixtures that were deciphered by an extensive structural analysis using mainly mass spectrometry and NMR spectroscopy. In addition, as part of their potential use as vectors of active drugs, these products were submitted to an integrity study on in vitro model of the blood-brain-barrier (BBB) and the intestinal epithelium. No toxicity has been observed, suggesting that applications for the vectorization of active ingredients can be expected.

Published
2020
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37. Single, short in-del, and copy number variations detection in monogenic dyslipidemia using a next-generation sequencing strategy

Author

Philippe Moulin, Séverine Nony, Sybil Charrière, O. Marmontel, Muriel Mahl, Chantal Jacobs, Alain Lachaux, Thomas Simonet, Kaddour Chabane, Gilles Millat, C. Marçais, Sabrina Dumont, M. Di Filippo, Claire Bardel, Alexandre Janin, Dominique Bozon, Véronique Bonnet, Noël Peretti, Cardiovasculaire, métabolisme, diabétologie et nutrition (CarMeN), Institut National de la Recherche Agronomique (INRA)-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 National de la Santé et de la Recherche Médicale (INSERM)-Hospices Civils de Lyon (HCL), Laboratoire de Biométrie et Biologie Evolutive - UMR 5558 (LBBE), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National de Recherche en Informatique et en Automatique (Inria)-VetAgro Sup - Institut national d'enseignement supérieur et de recherche en alimentation, santé animale, sciences agronomiques et de l'environnement (VAS)-Centre National de la Recherche Scientifique (CNRS), Biostatistiques santé, Département biostatistiques et modélisation pour la santé et l'environnement [LBBE], Université de Lyon-Université de Lyon-Institut National de Recherche en Informatique et en Automatique (Inria)-VetAgro Sup - Institut national d'enseignement supérieur et de recherche en alimentation, santé animale, sciences agronomiques et de l'environnement (VAS)-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National de Recherche en Informatique et en Automatique (Inria)-VetAgro Sup - Institut national d'enseignement supérieur et de recherche en alimentation, santé animale, sciences agronomiques et de l'environnement (VAS)-Centre National de la Recherche Scientifique (CNRS)-Laboratoire de Biométrie et Biologie Evolutive - UMR 5558 (LBBE), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Hospices Civils de Lyon (HCL)-Institut National de la Santé et de la Recherche Médicale (INSERM), hospices civils de Lyon, Hospices Civils de Lyon (HCL)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Institut National de la Recherche Agronomique (INRA)

Subjects
0301 basic medicine, genotype phenotype correlation, [SDV]Life Sciences [q-bio], Comorbidity, monogenic dyslipidemia, Familial hypercholesterolemia, 030204 cardiovascular system & hematology, Workflow, autosomal-dominant hypercholesterolemia, 0302 clinical medicine, INDEL Mutation, targeted next-generation sequencing, Medicine, Copy-number variation, Child, Genetics (clinical), Aged, 80 and over, Genetics & Heredity, apo-b gene, familial hypercholesterolemia, copy number variation, Ion torrent PGM, High-Throughput Nucleotide Sequencing, Middle Aged, 3. Good health, Child, Preschool, combined hypolipidemia, Adult, Adolescent, DNA Copy Number Variations, ldl-c levels, hypertriglyceridemia, In silico, density-lipoprotein-receptor, Computational biology, apolipoprotein-b, DNA sequencing, Diagnosis, Differential, Young Adult, 03 medical and health sciences, lipid disorders, Genetics, Humans, Genetic Predisposition to Disease, Mutation detection, Genetic Testing, Genetic Association Studies, Aged, Dyslipidemias, business.industry, PCSK9, severe, Hypertriglyceridemia, medicine.disease, 030104 developmental biology, coronary-heart-disease, business, Biomarkers, Dyslipidemia
Abstract

International audience; Optimal molecular diagnosis of primary dyslipidemia is challenging to confirm the diagnosis, test and identify at risk relatives. The aim of this study was to test the application of a single targeted next-generation sequencing (NGS) panel for hypercholesterolemia, hypocholesterolemia, and hypertriglyceridemia molecular diagnosis. NGS workflow based on a custom AmpliSeq panel was designed for sequencing the most prevalent dyslipidemia-causing genes (ANGPTL3, APOA5, APOC2, APOB, GPIHBP1, LDLR, LMF1, LPL, PCSK9) on the Ion PGM Sequencer. One hundred and forty patients without molecular diagnosis were studied. In silico analyses were performed using the NextGENe software and homemade tools for detection of copy number variations (CNV). All mutations were confirmed using appropriate tools. Eighty seven variations and 4 CNV were identified, allowing a molecular diagnosis for 40/116 hypercholesterolemic patients, 5/13 hypocholesterolemic patients, and 2/11, hypertriglyceridemic patients respectively. This workflow allowed the detection of CNV contrary to our previous strategy. Some variations were found in previously unexplored regions providing an added value for genotype-phenotype correlation and familial screening. In conclusion, this new NGS process is an effective mutation detection method and allows better understanding of phenotype. Consequently this assay meets the medical need for individualized diagnosis of dyslipidemia.

Published
2018

38. Physico-chemical studies of resveratrol, methyl-jasmonate and cyclodextrin interactions: an approach to resveratrol bioproduction optimization

Author

Véronique Bonnet, Christophe Clément, Eric Courot, David Landy, D. Cailleu, Florence Djedaïni-Pilard, David Mathiron, S. Pilard, E. Bertaut, E. Oliva, Résistance Induite et Bioprotection des Plantes - EA 4707 (RIBP), Université de Reims Champagne-Ardenne (URCA)-SFR Condorcet, and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Methyl jasmonate, Cyclodextrin, 010405 organic chemistry, [SDV]Life Sciences [q-bio], General Chemical Engineering, Isothermal titration calorimetry, General Chemistry, Resveratrol, 010402 general chemistry, Mass spectrometry, 01 natural sciences, Bioproduction, 0104 chemical sciences, Elicitor, chemistry.chemical_compound, chemistry, Organic chemistry, Molecule, ComputingMilieux_MISCELLANEOUS
Abstract

trans-Resveratrol (RSV) is a natural phenolic molecule of the stilbene family known for its anti-oxidant properties in the field of nutraceuticals and cosmetics. Its production by grapevine cell suspensions is induced by the addition to the culture medium of elicitor compounds, methyl jasmonate (MeJA) and cyclodextrins (CDs). Physico-chemical studies were performed to understand the mechanism of action of CDs on this bioproduction of RSV. Inclusion complexes of RSV in CDs were first observed and then interactions with MeJA were identified using various analytical techniques such as UV and nuclear magnetic resonance (NMR) spectroscopies, mass spectrometry (MS) and isothermal titration calorimetry (ITC).

Published
2018

39. Ordering of Saturated and Unsaturated Lipid Membranes near Their Phase Transitions Induced by an Amphiphilic Cyclodextrin and Cholesterol

Author

Véronique Bonnet, Florence Djedaïni-Pilard, Michel Roux, Institut de Biologie Intégrative de la Cellule (I2BC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire Bioénergétique Membranaire et Stress (LBMS), Département Biochimie, Biophysique et Biologie Structurale (B3S), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Biologie Intégrative de la Cellule (I2BC), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)

Subjects
Deuterium NMR, Phase transition, Magnetic Resonance Spectroscopy, [SDV]Life Sciences [q-bio], Lipid Bilayers, 02 engineering and technology, 03 medical and health sciences, chemistry.chemical_compound, Membrane Lipids, Phosphatidylcholine, Amphiphile, Electrochemistry, General Materials Science, POPC, Spectroscopy, 030304 developmental biology, chemistry.chemical_classification, 0303 health sciences, Cyclodextrins, Cyclodextrin, Chemistry, Bilayer, technology, industry, and agriculture, Surfaces and Interfaces, 021001 nanoscience & nanotechnology, Condensed Matter Physics, Crystallography, Membrane, Cholesterol, Phosphatidylcholines, lipids (amino acids, peptides, and proteins), 0210 nano-technology, Dimyristoylphosphatidylcholine, Hydrophobic and Hydrophilic Interactions
Abstract

When inserted in membranes of dimyristoyl phosphatidylcholine (DMPC), methylated β-cyclodextrins with one (TrimβMLC) or two (TrimβDLC) lauryl acyl chains grafted onto the hydrophilic cavity exert a "cholesterol-like ordering effect", by straightening the acyl chains in the fluid phase at temperatures near the chain melting transition. This effect may be related to pretransitional events such as the "anomalous swelling" known to occur with saturated phosphatidylcholine membranes. To investigate this model, order profiles and bilayer thicknesses of DMPC and unsaturated 1-palmitoyl-2-oleoyl-phosphatidylcholine (POPC) membranes containing amphiphilic cyclodextrins or cholesterol were determined by deuterium NMR. The pure lipid membranes display both a qualitatively similar chain ordering upon cooling in the fluid phase, more important at the chain extremity, which gets more pronounced near their fluid-to-gel transitions. Both membranes show a bilayer thickness increase by ∼0.5 Å just above their transition, as observed previously with saturated phosphatidylcholines of various chain lengths. Membrane-insertion of 5% TrimβMLC or cholesterol induces an important ordering of the DMPC acyl chains just above the transition, which is also more pronounced at the chain extremity. There is an additional increase of the bilayer thickness, most probably due to a deep insertion of these amphiphilic molecules, facilitated by increased bilayer softness in the anomalous swelling regime. These effects are more important with TrimβMLC than with cholesterol. By contrast, no enhanced acyl chain ordering was observed when approaching the transition of TrimβMLC-containing POPC membranes, as a possible consequence of an eventual lack of anomalous swelling in unsaturated lipid membranes. Insertion of higher concentrations of TrimβMLC was found to induce a magnetic orientation of the DMPC membranes in the fluid phase with 10% of this derivative, coupled with the appearance of a broad isotropic component when the concentration is raised to 20%. No membrane orientation or isotropic component was detected with TrimβMLC-containing POPC membranes.

Published
2019

40. A microscale double labelling of GAG oligosaccharides compatible with enzymatic treatment and mass spectrometry

Author

Romain R. Vivès, Véronique Bonnet, Cédric Przybylski, Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Groupe Structure et Activité des Glycosaminoglycanes (IBS-SAGAG ), Institut de biologie structurale (IBS - UMR 5075 ), Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement (LAMBE - UMR 8587), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources (LG2A) UMR7378 UPJV/CNRS, Université de Picardie Jules Verne (UPJV), Groupe Structure et Activité des Glycosaminoglycanes (IBS-SAGAG), Institut de biologie structurale (IBS - UMR 5075), Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Grenoble Alpes (UGA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Grenoble Alpes (UGA)

Subjects
Microgram, education, 010402 general chemistry, Mass spectrometry, 01 natural sciences, Catalysis, Glycosaminoglycan, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Labelling, Materials Chemistry, [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM], Microscale chemistry, chemistry.chemical_classification, Chromatography, 010405 organic chemistry, Sulfatase, Metals and Alloys, General Chemistry, [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biomolecules [q-bio.BM], 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Enzyme, chemistry, Ceramics and Composites, Heparinase I
Abstract

International audience; A novel double labelling of glycosaminoglycans (GAG) oligosaccharides by thia-Michael addition and deuterium incorporation at the non-reducing and reducing ends, respectively, was introduced. This was demonstrated to be both compatible with the heparin microgram scale and amenable for mass spectrometry analysis, without impairing enzymatic activities such as heparinase I and sulfatase HSulf-2.

Published
2019

41. The Uncommon Strong Inhibition of α-Glucosidase by Multivalent Glycoclusters Based on Cyclodextrin Scaffolds

Author

Abed Bil, Takwa Khanchouche, Véronique Bonnet, José Kovensky, Cédric Przybylski, Urjwan Alali, David Mathiron, Rémi Beaulieu, Mohammed Benazza, Aurélie Vallin, Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Plateforme Analytique (PFA), Université de Picardie Jules Verne (UPJV), Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
POLE 3, medicine.medical_treatment, Saccharomyces cerevisiae, 010402 general chemistry, 01 natural sciences, Biochemistry, medicine, Monosaccharide, [CHIM]Chemical Sciences, Glycoside Hydrolase Inhibitors, Physical and Theoretical Chemistry, IC50, Acarbose, chemistry.chemical_classification, Cyclodextrins, Molecular Structure, Cyclodextrin, 010405 organic chemistry, Chemistry, Insulin, Organic Chemistry, Glycoside, alpha-Glucosidases, Combinatorial chemistry, 3. Good health, 0104 chemical sciences, Propargyl, Click chemistry, Click Chemistry, Glycoconjugates, CSOB, medicine.drug
Abstract

New inhibitors of α-glucosidase based on perglycosylated cyclodextrins were synthesized via click-chemistry and compared to acarbose. , The homeostasis disruption of d -glucose causes diabetes, a dramatic chronic disease worldwide. Type 1 diabetes is a successfully treatable form, where blood d -glucose is regulated by insulin treatment. In contrast type 2 diabetes, the non-insulin dependent kind, is problematic. The control of the d -glucose blood level via intestinal α- d -glucosidase inactivation can be achieved by using competitive inhibitors, such as iminosugars ( e.g. acarbose) or sulfonium sugar derivatives ( e.g. salacinol). Recently, an unprecedented result showed that multivalent diamond nanoparticles grafted with unmodified sugars displayed α-glucosidase inhibition at low micromolar concentrations. Herein we describe the synthesis of multivalent glycoclusters using cyclodextrins (CDs) as scaffolds and an assessment of their role as inhibitors of α- d -glucosidase. The glycoclusters were efficiently obtained from per-azido α, β and γ-CD derivatives and propargyl glycosides using click-chemistry under microwave irradiation. The methodology was successfully applied to various protected and non-protected propargylated monosaccharides, including both O - and S -glycosides, giving clear evidence of its versatility. The targeted 6- per -glycosylated CDs were isolated in moderate to excellent yields (30\textendash 90%) by silica gel chromatography. The results showed inhibition of α-glucosidase from Saccharomyces cerevisiae with IC 50 values in the 32\textendash 132 μM range, lower than that of acarbose (IC 50 = ∼250 μM), a well-known competitive inhibitor used in the clinical treatment of type 2 diabetes. Preliminary experiments suggest a mixed-type non-competitive inhibition mode for these new glycoclusters.

Published
2019

42. Revisiting and improving the preparation of silicon-based electrodes for lithium-ion batteries: ball milling impact on poly(acrylic acid) polymer binders

Author

Mariama Ndour, Laure Monconduit, Thibaut Chartrel, Luc Aymard, Véronique Bonnet, Franck Dolhem, Sébastien Cavalaglio, Jean-Pierre Bonnet, Laboratoire réactivité et chimie des solides - UMR CNRS 7314 (LRCS), Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Réseau sur le stockage électrochimique de l'énergie (RS2E), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Aix Marseille Université (AMU)-Université de Pau et des Pays de l'Adour (UPPA)-Université de Nantes (UN)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP ), Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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), Université de Nantes (UN)-Aix Marseille Université (AMU)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Collège de France (CdF (institution))-Université de Picardie Jules Verne (UPJV)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP ), Université Grenoble Alpes (UGA)-Université Grenoble Alpes (UGA), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Materials science, Molar mass, Composite number, 02 engineering and technology, Polymer, [CHIM.MATE]Chemical Sciences/Material chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Dispersant, 0104 chemical sciences, Anode, chemistry.chemical_compound, chemistry, Chemical engineering, Electrode, Materials Chemistry, General Materials Science, 0210 nano-technology, Ball mill, Acrylic acid
Abstract

This study revisits and optimizes silicon/carbon/poly(acrylic acid) – (PAA) composite anode preparation for lithium-ion batteries. The objective is to analyze the specific impact of the high energy ball milling step on the PAA polymer binder and on the composite anode electrochemical behavior in order to improve cycling performance. For this purpose, three commercial PAAs with 15, 450 and 3000 kg mol−1 average molar masses are considered. PAA structural alterations induced by ball milling are investigated by SEC, IRTF, 1H NMR and TGA. It appears that PAA 15k is slightly degraded while higher molar mass PAAs are significantly deteriorated. An innovative optimized formulation, combining (1) ball milling of carbon and Si only followed by (2) magnetic stirring of this mixture with PAA and a dispersant is proposed and compared to an all ball milling formulation. The first step is essential to get good electrochemical performance and the second enables the maintenance of polymer integrity. The highest electrochemical capacity retention after 20 cycles is obtained for the PAA 450k-based electrode (84%) compared with those of PAA 15k and PAA 3000k of 62% and 29%, respectively. Interestingly, this capacity retention is also significantly improved compared with that of the corresponding PAA 450k all ball milling formulation electrode (65%).

Published
2019

43. Nanoparticles based on lipidyl-β-cyclodextrins: synthesis, characterization, and experimental and computational biophysical studies for encapsulation of atazanavir

Author

Vincent Banchet, Sébastien Buchoux, Aurélien L. Furlan, Catherine Sarazin, Yong Miao, Mathieu Létévé, Véronique Bonnet, Virginie Lambertyn, Jean Michel, Génie Enzymatique et Cellulaire (GEC), Université de Technologie de Compiègne (UTC)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Recherche en Nanosciences - EA 4682 (LRN), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV), Interfaces biomatériaux/tissus hôtes, and Université de Reims Champagne-Ardenne (URCA)-IFR53-Institut National de la Santé et de la Recherche Médicale (INSERM)

Subjects
chemistry.chemical_classification, Aqueous solution, Cyclodextrin, technology, industry, and agriculture, Nanoparticle, 02 engineering and technology, General Chemistry, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Catalysis, 3. Good health, 0104 chemical sciences, Bioavailability, Molecular dynamics, chemistry, Chemical engineering, Amphiphile, Materials Chemistry, Molecule, [CHIM]Chemical Sciences, 0210 nano-technology, Stoichiometry, ComputingMilieux_MISCELLANEOUS
Abstract

Amphiphilic cyclodextrins were synthesized from permethylated βCD with the aim of forming nanoparticles (NPs) that would encapsulate specific molecules (e.g. drugs) which could enhance their otherwise poor bioavailability. By grafting different fatty acids, four amphiphilic CDs were obtained. The self-assembling properties of three of these compounds were evaluated demonstrating micromolar critical aggregation concentration (CAC). Additionally, the stability of these nanoparticles was studied revealing that the compounds with C18 chains could be stored at 4 °C for prolonged periods without any issue. Finally, reliable characterization of NPs made of di-oleoyl-glycerolipidyl-β-cyclodextrin (DOCD) was performed by combining DLS, cryo-transmission electron microscopy (cryo-TEM) and molecular dynamics (MD) simulations. This revealed that DOCD nano-assemblies are roughly nano-scaled, spherical objects (diameter ca. 120 nm) without internal organization or aqueous compartments. Finally, atazanavir, used as a model drug, was entrapped in NPs whilst MD simulations were used to investigate molecule entrapment. This revealed that atazanavir interacts with DOCD to form a drug-loaded NP which does not fit with the 2 : 1 stoichiometry encapsulation classically observed in the cyclodextrin cavity.

Published
2018

44. Radical Coupling Allows a Fast and Tuned Synthesis of Densely Packed Polyrotaxanes Involving γ-Cyclodextrins and Polydimethylsiloxane

Author

Nakajima Tatsutoshi, Hervé Cheradame, Marie-Jeanne Clément, Nathalie Jarroux, Patricia Choppinet, Patrick A. Curmi, Francois Blin, Véronique Bonnet, Cédric Przybylski, Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement (LAMBE), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Institut de Chimie du CNRS (INC)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), Structure et activité des biomolécules normales et pathologiques (SABNP), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université d'Évry-Val-d'Essonne (UEVE), Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université d'Évry-Val-d'Essonne (UEVE)-Institut National de la Santé et de la Recherche Médicale (INSERM), and Menicon Co.

Subjects
Synthesis process, Polymers and Plastics, [SDV]Life Sciences [q-bio], Supramolecular assemblies, Size-exclusion chromatography, Silicones, Side reaction, 02 engineering and technology, 010402 general chemistry, Mass spectrometry, 01 natural sciences, Supramolecular assembly, Inorganic Chemistry, chemistry.chemical_compound, Size exclusion chromatography, Polymer chemistry, Materials Chemistry, Analytical characterization, Coupling, Cyclodextrins, Chromatography, Polydimethylsiloxane, Organic Chemistry, MALDI-TOF mass spectrometry, Hydrogels, Carbon-13 NMR, 021001 nanoscience & nanotechnology, Gamma-cyclodextrin, High conversions, Polydimethylsiloxane PDMS, 0104 chemical sciences, Microchannels, Molecular necklace, Monomer, chemistry, [PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph], 0210 nano-technology
Abstract

International audience; The first radical end-coupling synthesis of polydimethylsiloxane (PDMS)-γ-cyclodextrins (γ-CDs) based polyrotaxane is reported. Conversely to usual chemical way, the radical process leads to fast both controlled size and structure with minimal side reaction while exhibiting very high conversion rate (w/w, 80%). Pure PDMS-γ-CDs molecular necklaces were successfully isolated by preparative size exclusion chromatography and finely characterized both by 1D/2D/STD 1H and 13C NMR and MALDI-TOF mass spectrometry. The observations give clear evidence of the supramolecular assembly synthesis where the filling ratio (γ-CD/monomer unit) of PDMS chains is as high as 40% of γ-CDs. Combination of such radical-based coupling supported by detailed analytical characterizations appears at the forefront of a fast, suitable, and easily amenable scaling-up CDs-based polyrotaxane synthesis process.

Published
2016

45. Revealing cooperative binding of polycationic cyclodextrins with DNA oligomers by capillary electrophoresis coupled to mass spectrometry

Author

Juan M. Benito, José M. García Fernández, Carmen Ortiz Mellet, Cédric Przybylski, Véronique Bonnet, Ministerio de Economía y Competitividad (España), Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla-Consejo Superior de Investigaciones Científicas [Madrid] (CSIC), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), and Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
POLE 3, Cooperative effects, DNA, Single-Stranded, dnaN, Gene delivery, 010402 general chemistry, Mass spectrometry, 01 natural sciences, Biochemistry, Mass Spectrometry, Polymerization, Analytical Chemistry, chemistry.chemical_compound, Capillary electrophoresis, [CHIM]Chemical Sciences, Environmental Chemistry, Hill number, Spectroscopy, Cyclodextrins, Drug Carriers, Chromatography, Base Sequence, 010405 organic chemistry, Oligonucleotide, Electrophoresis, Capillary, Cooperative binding, DNA, 0104 chemical sciences, Polycationic cyclodextrins, chemistry, CE-MS, Nucleic acid, CSOB
Abstract

Gene delivery is critical for the development of nucleic acid-based therapies against a range of severe diseases. The conception of non-viral (semi)synthetic vectors with low cytotoxicity and virus-like efficiency is gathering a lot of efforts, but it represents a fantastic challenge still far from accomplishment. Carbohydrate-based scaffolds offer interesting features towards this end, such as easy availability, relatively cheap cost, tuning properties and a good biocompatibility. The lack of analytical methods providing quantitative and qualitative data on their binding properties with oligonucleotides (DNA/RNA), with a minimal time and sample consumption, represents a limitation for these channels. Here, we attempted to fill the gap by hyphenation of capillary electrophoresis with mass spectrometry (CE-MS). This coupling strategy allows discriminating free and complexed DNA oligomers with cationic cyclodextrins (CDs), determining the stoichiometry where the highest observed is always DNA: n/3(CD), and unambiguously assigning the partners through m/z detection. Very reliable data were obtained with migration time within 5.5 (standard deviation < 0.5%) and 25 min (standard deviation < 1.1%) for UV and MS detection, respectively. Furthermore, varying the nitrogen/phosphorus ratio (N/P), key parameters relating to the thermodynamics e.g. the micro and macroscopic dissociation constants K and K, respectively (both in low μM range) and the Gibbs free energy ΔG (−16.3 to −26.9 kJ mol), and also the cooperativity as Hill number (nH between 0.98 and 15.75) of the supramolecular process can be delineated, providing a unique tool for the high throughput screening and selection of efficient gene delivery carriers., The authors thank Genopole-France and the Conseil Régional d’Ile-de-France and the Spanish Ministerio de Economia y Competitividad (MinECo, contract no. SAF2013-44021-R and CTQ2015-64425-C2-1-R).

Published
2018

46. Méthodologie de suivi des espèces végétales rares mise en place par un réseau d’acteurs de la conservation

Author

Irène Till-Bottraud, Véronique Bonnet, Cédric Dentant, Noémie Fort, Pierre Salomez, and Richard Bonet

Subjects
0106 biological sciences, education.field_of_study, Frequency of occurrence, Ecology, Population, Rare species, Large array, Context (language use), Forestry, Plant Science, 15. Life on land, 010603 evolutionary biology, 01 natural sciences, 010601 ecology, Geography, Stakeholder network, Natura 2000, education
Abstract

There is an increasing need for data on the patterns of population changes for rare species at the regional, national and European scales in the context of the Natura 2000 reporting on the state of species’ conservation. This reporting requires the use of the same protocol over a whole region or country with the major constraint that it has to be shared by a large array of conservations and monitoring structures. The protocol has therefore to be both precise and reproducible but also simple enough to be used over a large number of sites and years, and has moreover to be accepted by various conservation structures.In this aim, the Alps-Ain flora conservation network (Reseau Alpes-Ain de Conservation de la Flore), a network composed of flora conservation stakeholders for 2 regions, Provence-Alpes-Cote d’Azur and Rhone-Alpes, set up a series of nested protocols to monitor populations at different spatial scales (levels). Each monitoring level is set up to answer to a specific aim and corresponds to a...

Published
2014

47. Diesterification of 3-[(β-Cyclodextrinyl)succinamido]propane-1,2-diol Catalysed by Lipase: Diastereoselectivity or Tridimensional Substrate Specificity?

Author

Florian Nolay, Christine Cézard, Véronique Bonnet, Imane Stasik, Cédric Gervaise, Florence Djedaïni-Pilard, and Catherine Sarazin

Subjects
chemistry.chemical_classification, biology, Cyclodextrin, 010405 organic chemistry, Chemistry, Stereochemistry, Organic Chemistry, Diol, Diastereomer, Transesterification, 010402 general chemistry, 01 natural sciences, 3. Good health, 0104 chemical sciences, Catalysis, Enzyme catalysis, chemistry.chemical_compound, biology.protein, Physical and Theoretical Chemistry, Lipase, Selectivity
Abstract

The transesterification of 3-[(β-cyclodextrinyl)succinamido]propane-1,2-diol with fatty esters catalyzed by immobilized lipase from Mucor miehei occurred with very different conversions of the two diastereoisomers [(R)- or (S)-amidopropanediol]. The highest conversion observed with the (S)-amidopropanediol can be related to either lipase diastereoselectivity or substrate specificity. To investigate the diastereoselectivity of the lipase, diastereoisomers of the methylated β-cyclodextrin were replaced by methylated glucopyranoside or methylleucine. No discrimation of the diastereoisomers by lipase was observed. Molecular modeling was performed to assess the lipase selectivity towards the two diastereoisomers. It was found that the (R)-amidopropanediol is stabilized by hydrogen bonding with the cyclodextrin rim resulting in less reactive hydroxy groups.

Published
2014

48. Toward a suitable structural analysis of gene delivery carrier based on polycationic carbohydrates by electron transfer dissociation tandem mass spectrometry

Author

Carmen Ortiz Mellet, Juan M. Benito, José M. García Fernández, Véronique Bonnet, Cédric Przybylski, Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement (LAMBE), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla / University of Sevilla-Consejo Superior de Investigaciones Científicas [Madrid] (CSIC), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Universidad de Sevilla / University of Sevilla, Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Centre National de la Recherche Scientifique (CNRS), Consejo Superior de Investigaciones Científicas [Madrid] (CSIC)-Universidad de Sevilla, Institut de Chimie du CNRS (INC)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), Universidad de Sevilla, Universidad de Sevilla. Departamento de Química orgánica, Genopole-France, Conseil régional d'Île-de-France, and Ministerio de Economía y Competitividad (MINECO). España

Subjects
Spectrometry, Mass, Electrospray Ionization, Carbohydrates, Electrons, Gene delivery, 010402 general chemistry, Mass spectrometry, Tandem mass spectrometry, 01 natural sciences, Biochemistry, Analytical Chemistry, Fragmentation (mass spectrometry), Polycationic, Tandem Mass Spectrometry, Carbohydrate Conformation, Polyamines, Environmental Chemistry, Molecule, Cyclodextrin, [CHIM]Chemical Sciences, Spectroscopy, chemistry.chemical_classification, Glycobiology, Biomolecule, 010401 analytical chemistry, Gene Transfer Techniques, ETD, Polyelectrolytes, Combinatorial chemistry, 0104 chemical sciences, ESI-MS/MS, Electron-transfer dissociation, chemistry
Abstract

Polycationic carbohydrates represent an attractive class of biomolecules for several applications and particularly as non viral gene delivery vectors. In this case, the establishment of structure-biological activity relationship requires sensitive and accurate characterization tools to both control and achieve fine structural deciphering. Electrospray-tandem mass spectrometry (ESI-MS/MS) appears as a suitable approach to address these questions. In the study herein, we have investigated the usefulness of electron transfer dissociation (ETD) to get structural data about five polycationic carbohydrates demonstrated as promising gene delivery agents. A particular attention was paid to determine the influence of charge states as well as both fluoranthene reaction time and supplementary activation (SA) on production of charge reduced species, fragmentation yield, varying from 2 to 62%, as well as to obtain the most higher both diversity and intensity of fragments, according to charge states and targeted compounds. ETD fragmentation appeared to be mainly directed toward pending group rather than carbohydrate cyclic scaffold leading to a partial sequencing for building blocks when amino groups are close to carbohydrate core, but allowing to complete structural deciphering of some of them, such as those including dithioureidocysteaminyl group which was not possible with CID only. Such findings clearly highlight the potential to help the rational choice of the suitable analytical conditions, according to the nature of the gene delivery molecules exhibiting polycationic features. Moreover, our ETD-MS/MS approach open the way to a fine sequencing/identification of grafted groups carried on various sets of oligo-/polysaccharides in various fields such as glycobiology or nanomaterials, even with unknown or questionable extraction, synthesis or modification steps.

Published
2016

49. CMC Binding Agent for Silicon Anodes in Li-Ion Batteries : The Impact of the Formulation

Author

Mariama Ndour, Jean-Pierre Bonnet, Sebastien Cavalaglio, Tristan Lombard, Cedric Przybylski, and Véronique Bonnet

Abstract

Li-ion batteries using silicon (Si) as an anodic electroactive material are promising devices that are currently being investigated. However, they have a major disadvantage, which is the large volume variation (about 300%) associated with the formation of the Li-Si alloy, this expansion leading to a rapid loss of cell capacity. The usual solution to this problem is the use of a polymeric binder to maintain the cohesion of the electrode during electrochemical cycling. Carboxymethylcellulose (CMC) [1], a semi-synthetic material, has been and is still one of the most studied and used polymers for this purpose. Thus, the formulation of the negative electrode requires a mixture of silicon, CMC and a carbon additive with the "SPEX" ball milling [2] to ensure good electrical conductivity within the composite mixture. This type of mixture, which is highly energetic, reduces the size of the particles and allows the formation of a nanostructured mixture, is essential for the activation of silicon. However, as we have very recently shown in the case of the use of polyacrylic acid (PAA) as a binder [3], it also causes significant degradation of polymer chains. The objective of the work presented here is to study the effect of this mechanical grinding on CMC, in particular the effect on average molecular weights and chemical degradation and, hence, the influence of the characteristics of this modified polysaccharide on the electrochemical performance of the composite negative electrode. To answer this question, we selected three types of commercial CMCs with different molecular weights (90, 250, 700) kg/mol [4]. The formulation of the negative electrode is then modified to better define the impact of the actual molar masses on silicon capacity retention. CMC is no longer mixed with the other components in the SPEX mill, which is too energetic for the polymer binder. This new formulation allows to see the effect of grinding on CMC and to discuss the impact of molar mass variation on capacity retention. A study on the effect of grinding was therefore carried out using different characterization techniques (SEC-MALLS, FTIR, MALDI-TOF, TGA-MS). References: Bridel, J.S., et al., In Situ Observation and Long-Term Reactivity of Si/C/CMC Composites Electrodes for Li-Ion Batteries. Journal of The Electrochemical Society, 2011. 158(6): p. A750-A759. Ponrouch, A. and M.R. Palacín, On the impact of the slurry mixing procedure in the electrochemical performance of composite electrodes for Li-ion batteries: A case study for mesocarbon microbeads (MCMB) graphite and Co3O4. Journal of Power Sources, 2011. 196(22): p. 9682-9688. Chartrel, T., et al., Revisiting and improving the preparation of silicon-based electrodes for lithium-ion batteries: ball milling impact on poly(acrylic acid) polymer binders. Materials Chemistry Frontiers, 2019. 3(5): p. 881-891. Lee, B.-R. and E.-S. Oh, Effect of Molecular Weight and Degree of Substitution of a Sodium-Carboxymethyl Cellulose Binder on Li4Ti5O12 Anodic Performance. The Journal of Physical Chemistry C, 2013. 117(9): p. 4404-4409.

Published
2019

50. Harnessing Polyisobutylene by Rotaxanation with γ-Cyclodextrin: Opportunities for Making Smart Molecular Necklaces

Author

Véronique Bonnet, Mathilde Abad, Nathalie Jarroux, Cédric Przybylski, Hassen Ramoul, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement (LAMBE), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Saclay (COmUE), Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Manufacture Française des Pneumatiques MICHELIN, Société Michelin, Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Manganese compounds, Materials science, Polymers and Plastics, Hydrophobicity, Supramolecular chemistry, Hydrophobic polymers, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Chemical reaction, Radical coupling, Matrix (chemical analysis), Chemical reactions, Reagent consumption, Polymer chemistry, Materials Chemistry, Physical and Theoretical Chemistry, Solubility, chemistry.chemical_classification, Cyclodextrins, Mass spectrometry, Organic Chemistry, Drug products, Polymer, 021001 nanoscience & nanotechnology, Condensed Matter Physics, Grafting, Gamma-cyclodextrin, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Molecular necklace, Polyisobutylenes, Polyrotaxanes, chemistry, Reagent, [PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph], Threading (protein sequence), 0210 nano-technology, Tetramethylguanidinium
Abstract

International audience; A new type of polyrotaxane based on the threading of γ-cyclodextrins (γ-CDs) along a highly hydrophobic polymer, polyisobutylene (PIB), is successfully prepared and finely characterized. The used radical coupling associated with tuned reaction time and temperature leads to a fast and controlled necklace synthesis with low reagent consumption. Synthesis exhibits appealing conversion and threading rates with almost 100% and 62–73%, respectively. A combination of well-established SEC and NMR techniques, with a more forefront MALDI-TOF MS approach, provides details on the original PIB and the resulting polyrotaxanes (M w , M n , PDI, and average number of γ-CD threaded). Interestingly, tetramethylguanidinium-2-(4-hydroxyphenylazo)benzoate in DMF for MALDI analysis is revealed as a suitable matrix to overcome solubility troubles widely observed with PIB. Moreover, rotaxanation appears as an alternative to the grafting of polar groups to modify/handle hydrophobic polymers. Such an approach offers new opportunities to achieve the synthesis, with unambiguous evidence, of new supramolecular necklaces based on highly hydrophobic polymers.

Published
2019

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