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1. Exploring Cluster-Dependent Antibacterial Activities and Resistance Pathways of NOSO-502 and Colistin against Enterobacter cloacae Complex Species

Author

Lucile Pantel, François Guérin, Marine Serri, François Gravey, Jessica Houard, Kelly Maurent, Marie Attwood, Alan Noel, Alasdair MacGowan, Emilie Racine, Vincent Cattoir, Maxime Gualtieri, Nosopharm, CHU Pontchaillou [Rennes], ARN régulateurs bactériens et médecine (BRM), Université de Rennes (UR)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ), CHU Caen, Normandie Université (NU)-Tumorothèque de Caen Basse-Normandie (TCBN), Dynamique Microbienne associée aux Infections Urinaires et Respiratoires (DYNAMICURE), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut National de la Santé et de la Recherche Médicale (INSERM), Southmead Hospital [Bristol, UK], and This work was partially performed within the framework of IMI’s GNA-NOW Program.

Subjects
CrrAB two-component-system, Pharmacology, Colistin, hetero-resistance, Enterobacter cloacae complex, PhoPQ, Microbial Sensitivity Tests, Anti-Bacterial Agents, Klebsiella pneumoniae, [SDV.MP]Life Sciences [q-bio]/Microbiology and Parasitology, Infectious Diseases, Bacterial Proteins, mechanism of resistance, Enterobacter cloacae, Drug Resistance, Bacterial, Humans, NOSO-502, Pharmacology (medical), KexD efflux pump
Abstract

International audience; The Enterobacter cloacae complex (ECC) is a group of diverse environmental and clinically relevant bacterial species associated with a variety of infections in humans. ECC have emerged as one of the leading causes of nosocomial infections worldwide. The purpose of this paper is to evaluate the activity of NOSO-502 and colistin (CST) against a panel of ECC clinical isolates, including different Hoffmann's clusters strains, and to investigate the associated resistance mechanisms. NOSO-502 is the first preclinical candidate of a novel antibiotic class, the odilorhabdins (ODLs). MIC50 and MIC90 of NOSO-502 against ECC are 1 mu g/mL and 2 mu g/mL, respectively, with a MIC range from 0.5 mu g/mL to 32 mu g/mL. Only strains belonging to clusters XI and XII showed decreased susceptibility to both NOSO-502 and CST while isolates from clusters I, II, IV, and IX were only resistant to CST. To understand this phenomenon, E. cloacae ATCC 13047 from cluster XI was chosen for further study. Results revealed that the two-component system Ea_01761-ECL_01762 (ortholog of CrrAB from Klebsiella pneumoniae) induces NOSO-502 hetero-resistance by expression regulation of the Ea_01758 efflux pump component (ortholog of KexD from K. pneumoniae) which could compete with AcrB to work with the multidrug efflux pump proteins AcrA and TolC. In E. cloacae ATCC 13047, CST-hetero-resistance is conferred via modification of the lipid A by addition of 4-amino-4-deoxy-L-arabinose controlled by PhoPQ. We identified that the response regulator Ea_01761 is also involved in this resistance pathway by regulating the expression of the Ea_01760 membrane transporter.

Published
2022

2. Total Synthesis of Tedarene A

Author

Nathalie Saffon-Merceron, Michel Baltas, Kelly Maurent, Florence Bedos-Belval, Corinne Vanucci-Bacqué, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), 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)-Centre National de la Recherche Scientifique (CNRS), and Université de Toulouse (UT)

Subjects
Aromatic compounds, Propanols, Pharmaceutical Science, Stereoisomerism, 010402 general chemistry, 01 natural sciences, Analytical Chemistry, Diarylheptanoids, Drug Discovery, Tedania ignis, Animals, [CHIM]Chemical Sciences, Molecule, Organic chemistry, Inhibitory effect, Pharmacology, Aldehydes, Diaryl ether, Molecular Structure, 010405 organic chemistry, Chemistry, Organic Chemistry, Total synthesis, Hydrocarbons, Porifera, 0104 chemical sciences, Complementary and alternative medicine, Mixtures, Alcohols, Yield (chemistry), Molecular Medicine, Ethers
Abstract

International audience; Tedarene A is a macrocyclic diaryl ether heptanoid isolated from the marine sponge Tedania ignis showing an inhibitory effect against nitric oxide production. The first total synthesis of tedarene A was achieved starting from the commercially available 3-(4-methoxyphenyl)propan-1-ol in nine steps and 15.3% overall yield. The synthetic sequence featured an E,Z-dienic bond introduction and a macrocyclization under Ullman conditions. During the synthesis, the E,E-isomer of tedarene A was also obtained and fully characterized.

Published
2017

3. Synthesis and biological evaluation of diarylheptanoids as potential antioxidant and anti-inflammatory agents

Author

Anne Nègre-Salvayre, Florence Bedos-Belval, Corinne Vanucci-Bacqué, Michel Baltas, Kelly Maurent, Nathalie Augé, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Maladies Métaboliques et Cardiovasculaires (I2MC), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées, Régulations cellulaires: lipidoses et atherosclerose, IFR 31 Louis Bugnard (IFR 31), Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-CHU Toulouse [Toulouse]-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-CHU Toulouse [Toulouse]-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Bedos-Belval, Florence, Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Institut de Chimie de Toulouse (ICT), 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)-Centre National de la Recherche Scientifique (CNRS), and Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)

Subjects
Lipopolysaccharides, 0301 basic medicine, Antioxidant, Lipopolysaccharide, medicine.medical_treatment, Pharmacology, medicine.disease_cause, 01 natural sciences, Antioxidants, Mice, chemistry.chemical_compound, Drug Discovery, [CHIM] Chemical Sciences, Cells, Cultured, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, Molecular Structure, Anti-Inflammatory Agents, Non-Steroidal, Diarylheptanoid, General Medicine, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, 3. Good health, [SDV.SP] Life Sciences [q-bio]/Pharmaceutical sciences, Macrocycle, Cell Survival, medicine.drug_class, Anti-inflammatory, Proinflammatory cytokine, Structure-Activity Relationship, 03 medical and health sciences, Anti-inflammatory activity, Diarylheptanoids, medicine, Animals, [CHIM]Chemical Sciences, Reactive oxygen species, Dose-Response Relationship, Drug, 010405 organic chemistry, Macrophages, Organic Chemistry, 0104 chemical sciences, RAW 264.7 Cells, 030104 developmental biology, chemistry, Reactive Oxygen Species, Oxidative stress
Abstract

International audience; Reactive oxygen species (ROS) are key signaling molecules and their overproduction plays an important role in the inflammation process, the secretion of inflammatory cytokines such as IL-1β and IL-6 and the progression of inflammatory disorders. Decreasing oxidative stress represents a promising challenge in the design of antioxidant and anti-inflammatory agents. In the present study, a series of new diarylheptanoids containing allylic alcohol, amide, hydantoin or triazole fragments were synthesized and fully characterized. We evaluated the ability of these agents to block the production of intracellular ROS and the subsequent inflammatory events exerted by lipopolysaccharide (LPS) on murine macrophage RAW 264.7. Five diarylheptanoids were found to exhibit the dual required properties.

Published
2018

4. ChemInform Abstract: N-Pyrrolidine-Based α/β-Peptides Incorporating ABOC, a Constrained Bicyclic β-Amino Acid, for Asymmetric Aldol Reaction Catalysis

Author

Kelly Maurent, Pierre Milbeo, Jean Martinez, Claude Didierjean, Laure Moulat, Monique Calmes, Aurélien Lebrun, and Emmanuel Aubert

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, Aldol reaction, Bicyclic molecule, chemistry, Organocatalysis, Carboxylic acid, Organic chemistry, General Medicine, Pyrrolidine, Octane, Amino acid, Catalysis
Abstract

Catalytic properties of 15 N-pyrrolidine-based α,β-peptides incorporating a constrained 2-aminobicyclo[2.2.2]octane carboxylic acid (ABOC) are evaluated in the asymmetric aldol reaction from acetone and some p-substituted benzaldehydes.

Published
2016

5. N-Pyrrolidine-based alpha/beta-peptides incorporating ABOC, a constrained bicyclic beta-amino acid, for asymmetric aldol reaction catalysis

Author

Kelly Maurent, Aurélien Lebrun, Emmanuel Aubert, Jean Martinez, Monique Calmes, Claude Didierjean, Pierre Milbeo, Laure Moulat, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Cristallographie, Résonance Magnétique et Modélisations (CRM2), and Centre National de la Recherche Scientifique (CNRS)-Université de Lorraine (UL)

Subjects
chemistry.chemical_classification, Asymmetric aldol reaction, Bicyclic molecule, 010405 organic chemistry, Stereochemistry, Organocatalysis, Carboxylic acid, Organic Chemistry, Absolute configuration, Tripeptide, 010402 general chemistry, 01 natural sciences, Biochemistry, Pyrrolidine, Short alpha/beta-peptide, 0104 chemical sciences, chemistry.chemical_compound, Residue (chemistry), chemistry, Aldol reaction, Drug Discovery, [CHIM.CRIS]Chemical Sciences/Cristallography, Bicyclic beta-amino acid
Abstract

International audience; A series of N-pyrrolidine-based alpha,beta-peptide catalysts incorporating a constrained 2-aminobicyclo[2.2.2] octane carboxylic acid (ABOC) residue were synthesized and evaluated in the asymmetric aldol reaction from acetone and some p-substituted benzaldehydes. Their catalytic properties were shown to be highly dependent on the amino acid sequences and on the absolute configuration of the ABOC residue that played a determinant role. Among the peptides tested, the heterochiral tripeptide H-Pro-(R)-ABOC-Asp-OCH3 13, that adopts a turn conformation in the solid state, proved to be the most efficient catalyst affording beta-hydroxy ketones in high yields and good enantioselectivities (up to 87%).

Published
2016

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