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2. Chimeric Protein–Protein Interface Inhibitors Allow Efficient Inhibition of Type III Secretion Machinery and Pseudomonas aeruginosa Virulence

Author

Rossimiriam Pereira de Freitas, Yung-Sing Wong, Aline Thomas, Sophie Plé, Younes Bouzidi, Antoine Fortuné, Caroline Barette, Flaviane Francisco Hilário, Ina Attrée, Marie-Odile Fauvarque, Tuan-Dung Ngo, Eric Faudry, Pathogenèse bactérienne et réponses cellulaires (PBRC), Biologie du Cancer et de l'Infection (BCI ), 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)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut National de la Santé et de la Recherche Médicale (INSERM)-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 National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Département de pharmacochimie moléculaire (DPM ), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Genetics and Chemogenomics (GenChem), Laboratoire de Biologie à Grande Échelle (BGE - UMR S1038), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-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)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Universidade Federal de Minas Gerais [Belo Horizonte] (UFMG), Universidade Federal de Ouro Preto (UFOP), Associations 'Vaincre la mucoviscidose' and 'Gregory Lemarchand', AVIESAN T3SS (ANR PRP1.4), GIS-IBiSA and ChemBioFrance, Froggy platform of the CIMENT infrastructure (https://ciment.ujf-grenoble.fr), which is supported by the Rhône-Alpes region (GRANT CPER07_13 CIRA), ANR-10-LABX-0049,GRAL,Grenoble Alliance for Integrated Structural Cell Biology(2010), ANR-15-CE11-0018,HemoPseudo,Pneumonie hémorragique à Pseudomonas aeruginosa : étude de nouvelles stratégies de virulence(2015), ANR-11-LABX-0003,ARCANE,Grenoble, une chimie bio-motivée(2011), ANR-17-EURE-0003,CBH-EUR-GS,CBH-EUR-GS(2017), ANR-10-LABX-0056,OSUG@2020,Innovative strategies for observing and modelling natural systems(2010), ANR-10-EQPX-0029,EQUIP@MESO,Equipement d'excellence de calcul intensif de Mesocentres coordonnés - Tremplin vers le calcul petaflopique et l'exascale(2010), Faudry, Eric, Grenoble Alliance for Integrated Structural Cell Biology - - GRAL2010 - ANR-10-LABX-0049 - LABX - VALID, Pneumonie hémorragique à Pseudomonas aeruginosa : étude de nouvelles stratégies de virulence - - HemoPseudo2015 - ANR-15-CE11-0018 - AAPG2015 - VALID, Grenoble, une chimie bio-motivée - - ARCANE2011 - ANR-11-LABX-0003 - LABX - VALID, CBH-EUR-GS - - CBH-EUR-GS2017 - ANR-17-EURE-0003 - EURE - VALID, Innovative strategies for observing and modelling natural systems - - OSUG@20202010 - ANR-10-LABX-0056 - LABX - VALID, Equipements d'excellence - Equipement d'excellence de calcul intensif de Mesocentres coordonnés - Tremplin vers le calcul petaflopique et l'exascale - - EQUIP@MESO2010 - ANR-10-EQPX-0029 - EQPX - VALID, Institut National de la Santé et de la Recherche Médicale (INSERM)-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), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), and Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])

Subjects
0301 basic medicine, [SDV]Life Sciences [q-bio], Protein subunit, 030106 microbiology, Virulence, hybrid molecules, medicine.disease_cause, Type three secretion system, Microbiology, 03 medical and health sciences, medicine, antivirulence, Secretion, biology, protein−protein interface inhibitors, Chemistry, Toxin, Pseudomonas aeruginosa, bacterial resistance, biology.organism_classification, [SDV.MP.BAC]Life Sciences [q-bio]/Microbiology and Parasitology/Bacteriology, Fusion protein, Type III secretion system, 030104 developmental biology, Infectious Diseases, click chemistry, [SDV.MP.BAC] Life Sciences [q-bio]/Microbiology and Parasitology/Bacteriology, Bacteria
Abstract

International audience; Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic pathogen naturally resistant to many common antibiotics and acquires new resistance traits at an alarming pace. Targeting the bacterial virulence factors by an antivirulence strategy, therefore, represents a promising alternative approach besides antibiotic therapy. The Type III secretion system (T3SS) of P. aeruginosa is one of its main virulence factors. It consists of more than 20 proteins building a complex syringe-like machinery enabling the injection of toxin into host cells. Previous works showed that disrupting interactions between components of this machinery efficiently lowers the bacterial virulence. Using automated target-based screening of commercial and in-house libraries of small molecules, we identified compounds inhibiting the protein-protein interaction between PscE and PscG, the two cognate chaperones of the needle subunit PscF of P. aeruginosa T3SS. Two hits were selected and assembled using Split/Mix/Click chemistry to build larger hybrid analogues. Their efficacy and toxicity were evaluated using phenotypic analysis including automated microscopy and image analysis. Two nontoxic hybrid leads specifically inhibited the T3SS and reduced the ex vivo cytotoxicity of bacteria and their virulence in Galleria mellonella.

Published
2019
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3. Targeting different binding sites in the CFTR structures allows to synergistically potentiate channel activity

Author

Sandra Mirval, Nesrine Baatallah, Jean-Paul Mornon, Julien Alliot, Isabelle Callebaut, Wael Zeinyeh, Arnaud Billet, Brice Hoffmann, Pierre Lehn, Ahmad Elbahnsi, Frédéric Becq, Renaud Zelli, Christophe Simard, Jean-Luc Décout, Romain Haudecoeur, Antoine Fortuné, Benjamin Boucherle, Benoit Chevalier, Alexandre Hinzpeter, Lionel Froux, Signalisation et Transports Ioniques Membranaires (STIM), Université de Poitiers-Université de Tours (UT)-Centre National de la Recherche Scientifique (CNRS), Institut de minéralogie, de physique des matériaux et de cosmochimie (IMPMC), Muséum national d'Histoire naturelle (MNHN)-Institut de recherche pour le développement [IRD] : UR206-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Université Grenoble Alpes (UGA), Institut Necker Enfants-Malades (INEM - UM 111 (UMR 8253 / U1151)), Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP), Université de Paris - UFR Médecine Paris Centre [Santé] (UP Médecine Paris Centre), Université de Paris (UP), Génétique, génomique fonctionnelle et biotechnologies (UMR 1078) (GGB), EFS-Université de Brest (UBO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO), Université de Poitiers-Université de Tours-Centre National de la Recherche Scientifique (CNRS), Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO)-Université de Brest (UBO)-EFS-Institut National de la Santé et de la Recherche Médicale (INSERM), Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Cité (UPCité), Université Paris Cité - UFR Médecine [Santé] (UPCité UFR Médecine), Université Paris Cité (UPCité), HAL-SU, Gestionnaire, UFR Médecine [Santé] - Université Paris Cité (UFR Médecine UPCité), and ANR-17-EURE-0003,CBH-EUR-GS,CBH-EUR-GS(2017)

Subjects
Mutant, Modulator, Cystic Fibrosis Transmembrane Conductance Regulator, Quinolones, Aminophenols, 3D structure, Cystic fibrosis, Combinatorial therapies, Ivacaftor, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, Drug Discovery, medicine, Humans, Binding site, CFTR, 030304 developmental biology, Pharmacology, Ussing chamber, 0303 health sciences, [SDV.MHEP] Life Sciences [q-bio]/Human health and pathology, Forskolin, Binding Sites, biology, Organic Chemistry, Drug Synergism, General Medicine, Potentiator, medicine.disease, Small molecule, Cystic fibrosis transmembrane conductance regulator, 3. Good health, Cell biology, Molecular Docking Simulation, chemistry, Purines, 030220 oncology & carcinogenesis, Benzamides, Mutation, biology.protein, Halide-sensitive fluorescence, [SDV.MHEP]Life Sciences [q-bio]/Human health and pathology, medicine.drug, HeLa Cells, Protein Binding
Abstract

International audience; Recent evidence shows that combination of correctors and potentiators, such as the drug ivacaftor (VX-770), can significantly restore the functional expression of mutated Cystic Fibrosis Transmembrane conductance Regulator (CFTR), an anion channel which is mutated in cystic fibrosis (CF). The success of these combinatorial therapies highlights the necessity of identifying a broad panel of specific binding mode modulators, occupying several distinct binding sites at structural level. Here, we identified two small molecules, SBC040 and SBC219, which are two efficient cAMP-independent potentiators, acting at low concentration of forskolin with EC50 close to 1 μM and in a synergic way with the drug VX-770 on several CFTR mutants of classes II and III. Molecular dynamics simulations suggested potential SBC binding sites at the vicinity of ATP-binding sites, distinct from those currently proposed for VX-770, outlining SBC molecules as members of a new family of potentiators.

Published
2020
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4. Exploring the structure-activity relationship of benzylidene-2,3-dihydro-1H-inden-1-one compared to benzofuran-3(2H)-one derivatives as inhibitors of tau amyloid fibers

Author

Emeline Boukherrouba, Camille Larosa, Kim-Anh Nguyen, Jérémy Caburet, Laurent Lunven, Hugues Bonnet, Antoine Fortuné, Ahcène Boumendjel, Benjamin Boucherle, Sabine Chierici, and Marine Peuchmaur

Subjects
Pharmacology, Protein Aggregates, Structure-Activity Relationship, Alzheimer Disease, Organic Chemistry, Drug Discovery, Humans, tau Proteins, General Medicine, Benzofurans
Abstract

Tauopathies, such as Alzheimer's disease, have been the subject of several hypotheses regarding the way to treat them. Hyperphosphorylation of tau protein leading to its aggregation is widely recognized as a key step in the development of these diseases resulting in neuronal dysfunction. The AcPHF6 model of tau that includes the shorter critical fragment involved in the protein aggregation was used in vitro to identify new potential inhibitors. Following a previous study on aurone derivatives, we herein compare this polyphenol family to a very close one, the benzylidene-2,3-dihydro-1H-inden-1-one (also named indanone). The structure activity relationship studies bring to light the importance of the hydroxylation pattern in both series: the more hydroxylated, the more active. In addition, the three-dimensional shape of the molecules is involved in their interaction mode with their target, thus defining their role either as inhibitors of fiber elongation or as fiber-binding molecules. Indanone 13a was identified as a promising inhibitor: its activity was confirmed by circular dichroism and atomic force microscopy studies.

Published
2022
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5. Recherches sur les végétaux fossiles de Meximieux

Author

Saporta, Gaston De, 1823-1895, Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900, Falsan, A. (Albert), 1833, University Library, University of North Carolina at Chapel Hill, Saporta, Gaston De, 1823-1895, Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900, and Falsan, A. (Albert), 1833

Subjects
France, Geology, Meximieux, Paleobotany
Published
1872

6. L'évolution du règne végétal : les cryptogames

Author

Saporta, Gaston, marquis de, 1823-1895, Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900, University Library, University of North Carolina at Chapel Hill, Saporta, Gaston, marquis de, 1823-1895, and Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900

Subjects
Cryptogams, Evolution, Plants
Published
1881

7. Recherches sur les végétaux fossiles de Meximieux

Author

Saporta, Gaston De, 1823-1895, Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900, Falsan, A. (Albert), 1833, University Library, University of North Carolina at Chapel Hill, Saporta, Gaston De, 1823-1895, Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900, and Falsan, A. (Albert), 1833

Subjects
France, Geology, Meximieux, Paleobotany

8. Recherches sur les végétaux fossiles de Meximieux

Author

Saporta, Gaston De, 1823-1895, Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900, Falsan, A. (Albert), 1833, University Library, University of North Carolina at Chapel Hill, Saporta, Gaston De, 1823-1895, Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900, and Falsan, A. (Albert), 1833

Subjects
France, Geology, Meximieux, Paleobotany

9. L'évolution du règne végétal : les cryptogames

Author

Saporta, Gaston, marquis de, 1823-1895, Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900, University Library, University of North Carolina at Chapel Hill, Saporta, Gaston, marquis de, 1823-1895, and Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900

Subjects
Cryptogams, Evolution, Plants

10. Atlas d'anatomie comparée des invertébrés

Author

Vayssière, A. (Albert Jean Baptiste Marie), 1854-1942, Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900, Harvard University, Museum of Comparative Zoology, Ernst Mayr Library, Vayssière, A. (Albert Jean Baptiste Marie), 1854-1942, and Marion, A.-F.‏ ‎ (Antoine Fortuné),‏ ‎ 1846-1900

Subjects
Anatomy, Anatomy, Comparative, Arthropoda, Cnidaria, Ctenophora, Echinodermata, Invertebrates, Mesozoa, Mollusks, Protozoans, Worms

12. Could we expect new praziquantel derivatives? A meta pharmacometrics/pharmacoinformatics analysis of all antischistosomal praziquantel derivatives found in the literature

Author

Antoine Fortuné, V.B. Ribeiro da Silva, J. El-Methni, A.L. da Silva, Aline Thomas, Brice Hoffmann, Benjamin Boucherle, M. Do Carmo Alves de Lima, Département de pharmacochimie moléculaire (DPM ), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Département de pharmacochimie moléculaire (DPM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes (UGA), Mathématiques Appliquées Paris 5 (MAP5 - UMR 8145), Institut National des Sciences Mathématiques et de leurs Interactions (INSMI)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Cité (UPCité), Unité de recherche en génomique végétale (URGV), and Institut National de la Recherche Agronomique (INRA)-Université d'Évry-Val-d'Essonne (UEVE)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Drug, Chemistry, Pharmaceutical, First line, media_common.quotation_subject, Pharmacoinformatics, Quantitative Structure-Activity Relationship, Bioengineering, Schistosomiasis, Pharmacology, Ligands, 01 natural sciences, Schistosomicides, parasitic diseases, Drug Discovery, Animals, Humans, Medicine, [SDV.MP.PAR]Life Sciences [q-bio]/Microbiology and Parasitology/Parasitology, pharmacometrics, ComputingMilieux_MISCELLANEOUS, media_common, Schistosoma, biology, 010405 organic chemistry, business.industry, praziquantel, fungi, Low activity, General Medicine, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, biology.organism_classification, medicine.disease, Pharmacometrics, 3. Good health, 0104 chemical sciences, Praziquantel, meta-analysis, 010404 medicinal & biomolecular chemistry, Logistic Models, pharmacoinformatics, Molecular Medicine, business, medicine.drug
Abstract

International audience; Praziquantel (PZQ) is the first line drug for the treatment of human Schistosoma spp. worm infections. However, it suffers from low activity towards immature stages of the worm, and its prolonged use induces resistance/tolerance. During the last 40 years, 263 PZQ analogues have been synthesized and tested against Schistosoma spp. worms, but less than 10% of them showed significant activity. Here, we propose a rationalization of the chemical space of the PZQ derivatives by a ligand-based approach. First, we constructed an in-house database with all PZQ derivatives available in the literature. This analysis shows a high heterogeneity in the data. Fortunately, all studies include PZQ as a reference, permitting the classification of compounds into three classes according to their activities. Models involving ligand-based pharmacophore and logistic regression were performed. Five physicochemical parameters were identified as the best to explain the biological activity. In the end, we proposed new PZQ derivatives with modifications at positions 1 and 7, we analysed them with our models, and we observed that they can be more active than the previously synthesized derivatives. The main goal of this work was to conduct the most valuable meta-pharmacometrics/pharmacoinformatics analysis with all Praziquantel medicinal chemistry data available in the literature.

Published
2019
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13. Toward a Better Understanding of the Basis of the Molecular Mimicry of Polysaccharide Antigens by Peptides

Author

Véronique Marcel-Peyre, Anne Imberty, Antoine Fortuné, Armelle Phalipon, Laurence A. Mulard, Catherine Simenel, Muriel Delepierre, and Marie-Jeanne Clément

Subjects
medicine.drug_class, Peptide, Biology, 010402 general chemistry, medicine.disease_cause, Monoclonal antibody, 01 natural sciences, Biochemistry, Turn (biochemistry), 03 medical and health sciences, Residue (chemistry), Shigella flexneri, Antigen, medicine, Molecular Biology, 030304 developmental biology, chemistry.chemical_classification, 0303 health sciences, Bacterial polysaccharide, Cell Biology, biology.organism_classification, 0104 chemical sciences, 3. Good health, Molecular mimicry, chemistry
Abstract

Protein conjugates of oligosaccharides or peptides that mimic complex bacterial polysaccharide antigens represent alternatives to the classical polysaccharide-based conjugate vaccines developed so far. Hence, a better understanding of the molecular basis ensuring appropriate mimicry is required in order to design efficient carbohydrate mimic-based vaccines. This study focuses on the following two unrelated sets of mimics of the Shigella flexneri 5a O-specific polysaccharide (O-SP): (i) a synthetic branched pentasaccharide known to mimic the average solution conformation of S. flexneri 5a O-SP, and (ii) three nonapeptides selected upon screening of phage-displayed peptide libraries with two protective murine monoclonal antibodies (mAbs) of the A isotype specific for S. flexneri 5a O-SP. By inducing anti-O-SP antibodies upon immunization in mice when appropriately presented to the immune system, the pentasaccharide and peptides p100c and p115, but not peptide p22, were qualified as mimotopes of the native antigen. NMR studies based on transferred NOE (trNOE) experiments revealed that both kinds of mimotopes had an average conformation when bound to the mAbs that was close to that of their free form. Most interestingly, saturation transfer difference (STD) experiments showed that the characteristic turn conformations adopted by the major conformers of p100c and p115, as well as of p22, are clearly involved in mAb binding. These latter experiments also showed that the branched glucose residue of the pentasaccharide was a key part of the determinant recognized by the protective mAbs. Finally, by using NMR-derived pentasaccharide and peptide conformations coupled to STD information, models of antigen-antibody interaction were obtained. Most interestingly, only one model was found compatible with experimental data when large O-SP fragments were docked into one of the mIgA-binding sites. This newly made available system provides a new contribution to the understanding of the molecular mimicry of complex polysaccharides by peptides and short oligosaccharides.

Published
2006
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14. mROC: a computer program for combining tumour markers in predicting disease states

Author

Benjamin Reiser, Antoine Fortuné, David Faraggi, Andrew Kramar, Département de pharmacochimie moléculaire (DPM), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF)

Subjects
Health Informatics, Multivariate normal distribution, Digestive System Neoplasms, Sensitivity and Specificity, 03 medical and health sciences, symbols.namesake, 0302 clinical medicine, Discriminative model, Statistics, Biomarkers, Tumor, Confidence Intervals, Humans, Diagnosis, Computer-Assisted, Linear combination, 030304 developmental biology, Mathematics, Likelihood Functions, 0303 health sciences, Receiver operating characteristic, Computer program, [INFO.INFO-IA]Computer Science [cs]/Computer Aided Engineering, Confidence interval, Carcinoembryonic Antigen, Computer Science Applications, F-distribution, ROC Curve, 030220 oncology & carcinogenesis, symbols, Area under the roc curve, Software
Abstract

Receiver operating characteristic (ROC) curves are limited when several diagnostic tests are available, mainly due to the problems of multiplicity and inter-relationships between the different tests. The program presented in this paper uses the generalised ROC criteria, as well as its confidence interval, obtained from the non-central F distribution, as a possible solution to this problem. This criterion corresponds to the best linear combination of the test for which the area under the ROC curve is maximal. Quantified marker values are assumed to follow a multivariate normal distribution but not necessarily with equal variances for two populations. Other options include Box–Cox variable transformations, QQ-plots, interactive graphics associated with changes in sensitivity and specificity as a function of the cut-off. We provide an example to illustrate the usefulness of data transformation and of how linear combination of markers can significantly improve discriminative power. This finding highlights potential difficulties with methods that reject individual markers based on univariate analyses.

Published
2001
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15. New 7-methylguanine derivatives targeting the influenza polymerase PB2 cap-binding domain

Author

Oliver Szolar, Antoine Fortuné, Jean-Luc Décout, Andrea Wolkerstorfer, Delphine Guilligay, Thomas Lunardi, Stephen Cusack, Stéphane Pautus, Joe Lewis, and Peter Sehr

Subjects
Models, Molecular, Guanine, viruses, Crystallography, X-Ray, Structure-Activity Relationship, Viral Proteins, Transcription (biology), Heterotrimeric G protein, Drug Discovery, Structure–activity relationship, Polymerase, Binding Sites, biology, Dose-Response Relationship, Drug, Molecular Structure, Chemistry, RNA-Dependent RNA Polymerase, Molecular biology, Biochemistry, Viral replication, Docking (molecular), Influenza A virus, Biotinylation, biology.protein, Molecular Medicine, Binding domain
Abstract

The heterotrimeric influenza virus polymerase performs replication and transcription of viral RNA in the nucleus of infected cells. Transcription by "cap-snatching" requires that host-cell pre-mRNAs are bound via their 5' cap to the PB2 subunit. Thus, the PB2 cap-binding site is potentially a good target for new antiviral drugs that will directly inhibit viral replication. Docking studies using the structure of the PB2 cap-binding domain suggested that 7-alkylguanine derivatives substituted at position N-9 and N-2 could be good candidates. Four series of 7,9-di- and 2,7,9-trialkyl guanine derivatives were synthesized and evaluated by an AlphaScreen assay in competition with a biotinylated cap analogue. Three synthesized compounds display potent in vitro activity with IC50 values lower than 10 μM. High-resolution X-ray structures of three inhibitors in complex with the H5N1 PB2 cap-binding domain confirmed the binding mode and provide detailed information for further compound optimization.

Published
2013

16. Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase

Author

Coralie Pallier, Antoine Fortuné, Edwige Nicolle, Ahcène Boumendjel, Catherine Belle, Abdelhakim Ahmed-Belkacem, Romain Haudecoeur, Jean-Michel Pawlotsky, Wei Yi, Rozenn Brillet, Guellaen, Georges, Département de pharmacochimie moléculaire (DPM), Université Joseph Fourier - Grenoble 1 (UJF)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut Mondor de Recherche Biomédicale (IMRB), Institut National de la Santé et de la Recherche Médicale (INSERM)-IFR10-Université Paris-Est Créteil Val-de-Marne - Paris 12 (UPEC UP12), Département de Chimie Moléculaire (DCM), Laboratoire de virologie, Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Hôpital Bicêtre, Centre National de Référence Virus des hépatites B, C et Delta, Institut National de la Transfusion Sanguine [Paris] (INTS)-Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP), R. H. is a recipient of a fellowship grant from the Ministère de l'Enseignement et de la Recherche to whom he is very thankful. A part of the project related to this article is funded by l'Agence Nationale de la Recherche (ANR). W.Y is a recipient of a fellowship from the University of Sun Yat-Sen (China) to whom he is thankful., Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Paris-Est Créteil Val-de-Marne - Paris 12 (UPEC UP12)-IFR10, and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Joseph Fourier - Grenoble 1 (UJF)

Subjects
Models, Molecular, Stereochemistry, Hepacivirus, Hepatitis C virus, viruses, Allosteric regulation, RNA-dependent RNA polymerase, 010402 general chemistry, medicine.disease_cause, Antiviral Agents, 01 natural sciences, Article, chemistry.chemical_compound, RNA polymerase, Drug Discovery, Aurone, medicine, [SDV.BBM] Life Sciences [q-bio]/Biochemistry, Molecular Biology, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, Benzofurans, biology, 010405 organic chemistry, Mutagenesis, RNA-Dependent RNA Polymerase, biology.organism_classification, Enzyme assay, 0104 chemical sciences, 3. Good health, chemistry, biology.protein, Molecular Medicine
Abstract

International audience; We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 μM and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indol-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 μM. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.

Published
2011
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17. 2-Arylidenedihydroindole-3-ones: design, synthesis, and biological activity on bladder carcinoma cell lines

Author

Pierre Champelovier, Jean Boutonnat, Bastien Gerby, Ahcène Boumendjel, Madeleine Blanc, Xavier Ronot, Pierre Paul Bringuier, Antoine Fortuné, Département de pharmacochimie moléculaire (DPM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF), Techniques de l'Ingénierie Médicale et de la Complexité - Informatique, Mathématiques et Applications, Grenoble - UMR 5525 (TIMC-IMAG), VetAgro Sup - Institut national d'enseignement supérieur et de recherche en alimentation, santé animale, sciences agronomiques et de l'environnement (VAS)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF), EPHE, VetAgro Sup - Institut national d'enseignement supérieur et de recherche en alimentation, santé animale, sciences agronomiques et de l'environnement (VAS)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF)-VetAgro Sup - Institut national d'enseignement supérieur et de recherche en alimentation, santé animale, sciences agronomiques et de l'environnement (VAS)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF), RFMQ, Université Grenoble Alpes (UGA)-Université Joseph Fourier - Grenoble 1 (UJF)-Centre National de la Recherche Scientifique (CNRS), Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP)-IMAG-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes (UGA), Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP)-IMAG-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes (UGA)-Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP)-IMAG-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes (UGA), Laboratoire Central d'Anatomie et de Cytologie Pathologiques [Hôpital Edouard Herriot - HCL], Hôpital Edouard Herriot [CHU - HCL], and Hospices Civils de Lyon (HCL)-Hospices Civils de Lyon (HCL)

Subjects
Cell signaling, Indoles, [SDV]Life Sciences [q-bio], Clinical Biochemistry, Pharmaceutical Science, [SDV.CAN]Life Sciences [q-bio]/Cancer, Antineoplastic Agents, Apoptosis, urologic and male genital diseases, 01 natural sciences, Biochemistry, 03 medical and health sciences, Carcinoma Cell, Cell Line, Tumor, Drug Discovery, STAT5 Transcription Factor, Humans, Receptor, Fibroblast Growth Factor, Type 3, Molecular Biology, ComputingMilieux_MISCELLANEOUS, 030304 developmental biology, Cell Proliferation, Neoplasm Staging, 0303 health sciences, 010405 organic chemistry, Chemistry, Organic Chemistry, Carcinoma, Biological activity, 3. Good health, 0104 chemical sciences, Cell biology, Focal Adhesion Kinase 2, Design synthesis, Urinary Bladder Neoplasms, Active compound, Cell culture, Drug Design, Molecular Medicine, Cell signaling pathways, Signal Transduction
Abstract

International audience; 2-Arylidenedihydroindole-3-ones were assayed for their antiproliferative and apoptotic abilities as potential drug candidates to treat bladder tumor. These compounds were tested on cell lines obtained from bladder tumors of various stages [superficial (pTa and pT1) vs. invasive (pT2)]. The most active compound (3c) inhibited the proliferation, induced apoptosis, and decreased the expression of p-Stat5 and p-Pyk2 in DAG-1 and RT112 lines in which the FGFR3 is either mutated or overexpressed. Knowing that FGFR3 is involved in cell proliferation, differentiation, and migration through cell signaling pathways including p-Stat5 way via p-Pyk2, let us assume that compound 3c may probably act through FGFR3 pathway.

Published
2006
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18. WS23.1 Models of the 3D structure of CFTR: from the understanding of the protein functions to the design of correctors

Author

Mathilde Jollivet, Isabelle Callebaut, Pierre Lehn, Antoine Fortuné, Jean-Paul Mornon, Frédéric Becq, Brice Hoffmann, Jean-Luc Décout, Romain Haudecoeur, Clément Boinot, and B. Boucherie

Subjects
Pulmonary and Respiratory Medicine, business.industry, Pediatrics, Perinatology and Child Health, Medicine, Pediatrics, Perinatology, and Child Health, business, Humanities
Abstract

B. Hoffmann1, J.-P. Mornon1, B. Boucherle2, A. Fortune2, R. Haudecoeur2, C. Boinot3, M. Jollivet3, J.-L. Decout2, F. Becq3, P. Lehn4, I. Callebaut1. 1Universite Pierre et Marie Curie, CNRS, MNHN, IRD, IMPMC, UMR 7590, Paris, France; 2Universite Joseph Fourier, UJF/CNRS, DPM, UMR 5063, Grenoble, France; 3Universite de Poitiers, CNRS, Laboratoire STIM, ERL 7368, Poitiers, France; 4Universite de Bretagne Occidentale, INSERM U 1078, Brest, France

Published
2014
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22. Avant-postes de cavalerie légère : souvenirs

Author

Brack, Antoine Fortuné de

Abstract

par F.é de Brack, Exlibrisstempel: "Militair-Bibliothek Zürich, des Cantons" 002275167_0001 Exemplar der ETH-BIB, Exlibrisetikette: "Militair-Bibliothek" 002165079_0001 Exemplar der ETH-BIB

Published
1830
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25. Papiers et correspondances provenant de Mme Récamier.XIXe s. XXXIII-XL Lettres adressées à Mme Récamier. XL Salvandy - Weiss-Kirck.

Author

Récamier, Jeanne-Françoise-Julie-Adelaïde, dite Juliette Bernard, Mme. Destinataire de lettres, Salvo, Lucie, Schlegel, August Wilhelm von, Broglie, Albertine de Staël, Staël, Auguste de, Staël, Mme Auguste de, Tastu, Amable Voïart, Tourgenev, Nicolas, Ballanche, Pierre-Simon, Saint-George de Vérac, Armand-Maximilien-François-Joseph-Olivier, Barante, Baron Amable-Guillaume-Prosper Brugière de, Catellan de Caumont, Amélie-Louise-Marie-Madeleine Julien, Voutier, Colonel Louis. Destinataire de lettres, Abrantès, Laure Junot, Custine, Astolphe, Genlis, Stéphanie-Félicité Ducrest de Saint-Aubin. Destinataire de lettres, Noailles, Paul, Boigne, Éléonore-Adèle d'Osmond. Destinataire de lettres, Duras, Claire de Kersaint, Pasquier, Baron Étienne, Chateaubriand, Vicomte François-René de, Gérando, Baron Joseph-Marie de, Staël-Holstein, Anne-Louise-Germaine Necker, Gérando, Marie-Anne de Rathsamhausen, Hautefeuille, Anne-Albe-Cornélie de Beaurepaire, David, Paul, Beaufort D'Hautpoul, Anne-Marie de Montgeroult de Coutances, Hochet, Claude, Montmorency-Laval, Adrien, Lebrun, Pierre-Antoine, Legris-Duval, Abbé René-Michel, Montmorency-Laval, Mathieu, Charles XIV, Jean-Baptiste-Jules Bernadotte. Destinataire de lettres, Navarre, Marie-Louise-Charlotte Poullot de, Révoil, Mme Pierre-Henri. Destinataire de lettres, Deschamps, Antoni. Destinataire de lettres, Ostrowski, Christian. Destinataire de lettres, Marmont, Anne-Marie-Hortense Perregaux, Randall, Fanny, Rilliet, Mme, Artaud de Montor, Alexis-François. Destinataire de lettres, Salvage de Faverolles, Mme, Staël, Albert de. Destinataire de lettres, Clarke, Mlle. Destinataire de lettres, Sabran, Elzéar. Destinataire de lettres, Loménie, Charles de. Destinataire de lettres, Bertaux, Émile. Destinataire de lettres, Chateaubriand, Vicomte François-René de. Auteur de lettres, Récamier, Jeanne-Françoise-Julie-Adelaïde, dite Juliette Bernard, Mme. Producteur d'un fonds, Salvandy, Julie Féray. Auteur de lettres, Sapey, Charles. Auteur de lettres, Saulieu, R. Bastard. Auteur de lettres, Schlosser, Mina. Auteur de lettres, Sébastiani, Fanny. Auteur de lettres, Sermésy, Mme de. Auteur de lettres, Sévery, Mme L. de. Auteur de lettres, Sievers, Professeur. Auteur de lettres, Soutzo, Marie. Auteur de lettres, Béranger, Pierre-Jean de. Auteur de lettres, Staël, G. de. Auteur de lettres, Stuart de Rothesay, E. Auteur de lettres, Thibaudeau, Mathilde. Auteur de lettres, Thierry, Augustin. Auteur de lettres, Thierry, Julie de Querangal. Auteur de lettres, Touchon, Pasteur Pierre-Frédéric. Auteur de lettres, Trollope, Frances Milton. Auteur de lettres, Valence, Pulchérie de Genlis. Auteur de lettres, Valéry, Antoine. Auteur de lettres, Kellermann, Edmond. Auteur de lettres, Vatout, Jean. Auteur de lettres, Viénot, Gustave. Auteur de lettres, Volckovsky, Princesse Sophie. Auteur de lettres, Voutier, Colonel Louis. Auteur de lettres, Waldenburg, Prince de. Auteur de lettres, Waldenburg, Mathilde de. Auteur de lettres, Waldor, Mélanie Villenave. Auteur de lettres, Walsh, Vicomte Édouard. Auteur de lettres, Weiskirck, N. Auteur de lettres, Brack, Général Antoine-Fortuné Brach. Auteur de lettres, Talleyrand-Périgord, Dorothée de Courlande. Auteur de lettres, Fontenilliat, de. Auteur de lettres, Galitzine, Princesse Marie. Auteur de lettres, Isabey, Eugène. Auteur de lettres, Le Roy. Auteur de lettres, Lieven, Princesse de. Auteur de lettres, Loye, Aimé de. Auteur du texte, Marie-Amélie de Bourbon, reine des Français. Auteur de lettres, Moreau, Général Jean-Victor. Auteur de lettres, Orsel, Victor. Auteur de lettres, Ostrowski, Christian. Auteur de lettres, Deschamps, Antoni. Auteur de lettres, Ranke, L. Auteur de lettres, Bertaux, Émile. Auteur de lettres, Loménie, Charles de. Auteur de lettres, Récamier, Jeanne-Françoise-Julie-Adelaïde, dite Juliette Bernard, Mme. Destinataire de lettres, Salvo, Lucie, Schlegel, August Wilhelm von, Broglie, Albertine de Staël, Staël, Auguste de, Staël, Mme Auguste de, Tastu, Amable Voïart, Tourgenev, Nicolas, Ballanche, Pierre-Simon, Saint-George de Vérac, Armand-Maximilien-François-Joseph-Olivier, Barante, Baron Amable-Guillaume-Prosper Brugière de, Catellan de Caumont, Amélie-Louise-Marie-Madeleine Julien, Voutier, Colonel Louis. Destinataire de lettres, Abrantès, Laure Junot, Custine, Astolphe, Genlis, Stéphanie-Félicité Ducrest de Saint-Aubin. Destinataire de lettres, Noailles, Paul, Boigne, Éléonore-Adèle d'Osmond. Destinataire de lettres, Duras, Claire de Kersaint, Pasquier, Baron Étienne, Chateaubriand, Vicomte François-René de, Gérando, Baron Joseph-Marie de, Staël-Holstein, Anne-Louise-Germaine Necker, Gérando, Marie-Anne de Rathsamhausen, Hautefeuille, Anne-Albe-Cornélie de Beaurepaire, David, Paul, Beaufort D'Hautpoul, Anne-Marie de Montgeroult de Coutances, Hochet, Claude, Montmorency-Laval, Adrien, Lebrun, Pierre-Antoine, Legris-Duval, Abbé René-Michel, Montmorency-Laval, Mathieu, Charles XIV, Jean-Baptiste-Jules Bernadotte. Destinataire de lettres, Navarre, Marie-Louise-Charlotte Poullot de, Révoil, Mme Pierre-Henri. Destinataire de lettres, Deschamps, Antoni. Destinataire de lettres, Ostrowski, Christian. Destinataire de lettres, Marmont, Anne-Marie-Hortense Perregaux, Randall, Fanny, Rilliet, Mme, Artaud de Montor, Alexis-François. Destinataire de lettres, Salvage de Faverolles, Mme, Staël, Albert de. Destinataire de lettres, Clarke, Mlle. Destinataire de lettres, Sabran, Elzéar. Destinataire de lettres, Loménie, Charles de. Destinataire de lettres, Bertaux, Émile. Destinataire de lettres, Chateaubriand, Vicomte François-René de. Auteur de lettres, Récamier, Jeanne-Françoise-Julie-Adelaïde, dite Juliette Bernard, Mme. Producteur d'un fonds, Salvandy, Julie Féray. Auteur de lettres, Sapey, Charles. Auteur de lettres, Saulieu, R. Bastard. Auteur de lettres, Schlosser, Mina. Auteur de lettres, Sébastiani, Fanny. Auteur de lettres, Sermésy, Mme de. Auteur de lettres, Sévery, Mme L. de. Auteur de lettres, Sievers, Professeur. Auteur de lettres, Soutzo, Marie. Auteur de lettres, Béranger, Pierre-Jean de. Auteur de lettres, Staël, G. de. Auteur de lettres, Stuart de Rothesay, E. Auteur de lettres, Thibaudeau, Mathilde. Auteur de lettres, Thierry, Augustin. Auteur de lettres, Thierry, Julie de Querangal. Auteur de lettres, Touchon, Pasteur Pierre-Frédéric. Auteur de lettres, Trollope, Frances Milton. Auteur de lettres, Valence, Pulchérie de Genlis. Auteur de lettres, Valéry, Antoine. Auteur de lettres, Kellermann, Edmond. Auteur de lettres, Vatout, Jean. Auteur de lettres, Viénot, Gustave. Auteur de lettres, Volckovsky, Princesse Sophie. Auteur de lettres, Voutier, Colonel Louis. Auteur de lettres, Waldenburg, Prince de. Auteur de lettres, Waldenburg, Mathilde de. Auteur de lettres, Waldor, Mélanie Villenave. Auteur de lettres, Walsh, Vicomte Édouard. Auteur de lettres, Weiskirck, N. Auteur de lettres, Brack, Général Antoine-Fortuné Brach. Auteur de lettres, Talleyrand-Périgord, Dorothée de Courlande. Auteur de lettres, Fontenilliat, de. Auteur de lettres, Galitzine, Princesse Marie. Auteur de lettres, Isabey, Eugène. Auteur de lettres, Le Roy. Auteur de lettres, Lieven, Princesse de. Auteur de lettres, Loye, Aimé de. Auteur du texte, Marie-Amélie de Bourbon, reine des Français. Auteur de lettres, Moreau, Général Jean-Victor. Auteur de lettres, Orsel, Victor. Auteur de lettres, Ostrowski, Christian. Auteur de lettres, Deschamps, Antoni. Auteur de lettres, Ranke, L. Auteur de lettres, Bertaux, Émile. Auteur de lettres, and Loménie, Charles de. Auteur de lettres

Abstract

Chateaubriand, Vicomte François-René de. Lettre(s), Récamier, Jeanne-Françoise-Julie-Adelaïde, dite Juliette Bernard, Mme. Papiers et correspondance, Récamier, Jeanne-Françoise-Julie-Adelaïde, dite Juliette Bernard, Mme. Lettre(s) reçue(s), Récamier, Jeanne-Françoise-Julie-Adelaïde, dite Juliette Bernard, Mme. Lettre(s) reçue(s), Contient : Salvandy, Julie Féray, Comtesse Narcisse-Achille de. Lettre(s) ; Salvo, Lucie, Marquise de. Lettre(s) ; Sapey, Charles, homme politique. Lettre(s) ; Saulieu, R. Bastard, Mme de. Lettre(s) ; Schlegel, August Wilhelm von. Lettre(s) ; Schlosser, Mina. Lettre(s) ; Sébastiani, Fanny. Lettre(s) ; Sermésy, Mme de. Lettre(s) ; Sévery, Mme L. de. Lettre(s) ; Sievers, Professeur. Lettre(s) ; Soutzo, Marie. Lettre(s) ; Broglie, Albertine de Staël, Duchesse Victor de. Lettre(s) ; Staël, Auguste de. Lettre(s) ; Béranger, Pierre-Jean de. Lettre(s) ; Staël, Mme Auguste de. Lettre(s) ; Staël, G. de. Lettre(s) ; Stuart de Rothesay, E.. Lettre(s) ; Tastu, Amable Voïart, Mme Joseph. Lettre(s) ; Thibaudeau, Mathilde. Lettre(s) ; Thierry, Augustin. Lettre(s) ; Thierry, Julie de Querangal, Mme Augustin. Lettre(s) ; Touchon, Pasteur Pierre-Frédéric. Lettre(s) ; Tourgenev, Nicolas. Lettre(s) ; Ballanche, Pierre-Simon. Lettre(s) reçue(s) ; Trollope, Frances Milton, Mrs. Thomas Anthony. Lettre(s) ; Valence, Pulchérie de Genlis, Comtesse de. Lettre(s) ; Valéry, Antoine. Lettre(s) ; Kellermann, Edmond, duc de Valmy, homme politique. Lettre(s) ; Vatout, Jean, dit Julien. Lettre(s) ; Saint-George de Vérac, Armand-Maximilien-François-Joseph-Olivier, Marquis de. Lettre(s) ; Viénot, Gustave. Lettre(s) ; Volckovsky, Princesse Sophie. Lettre(s) ; Voutier, Colonel Louis. Lettre(s) ; Waldenburg, Prince de. Lettre(s) ; Waldenburg, Mathilde de. Lettre(s) ; Waldor, Mélanie Villenave, Mme. Lettre(s) ; Walsh, Vicomte Édouard. Lettre(s) ; Weiskirck, N.. Lettre(s) ; Barante, Baron Amable-Guillaume-Prosper Brugière de, homme politique. Lettre(s) ; Catellan de Caumont, Amélie-Louise-Marie-Madeleine Julien, Marquise de. Lettre(s) reçue(s) ; Brack, Général Antoine-Fortuné Brach, dit de. Lettre(s) ; Voutier, Colonel Louis. Lettre(s) reçue(s) ; Abrantès, Laure Junot, Duchesse d'. Lettre(s) reçue(s) ; Custine, Astolphe, Marquis de. Lettre(s) ; Genlis, Stéphanie-Félicité Ducrest de Saint-Aubin, Marquise de, Numérisation effectuée à partir d'un document de substitution : R 65028., Récamier, Jeanne-Françoise-Julie-Adelaïde, dite Juliette Bernard, Mme. Papiers et correspondance, Récamier, Jeanne-Françoise-Julie-Adelaïde, dite Juliette Bernard, Mme. Lettre(s) reçue(s)

26. Essai sur la guerre de partisans

Author

Davydov, Denis Vasil'evich, Polignac, Héraclius de, 1788-1871, Brack, Antoine Fortuné de, Boquet et Compagnie, Imprimeurs, Davydov, Denis Vasil'evich, Polignac, Héraclius de, 1788-1871, Brack, Antoine Fortuné de, and Boquet et Compagnie, Imprimeurs

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