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Thèse Docteur De L'université De Haute-Alsace UNIVERSITE DE HAUTE-ALSACE UNIVERSITE DE STRASBOURG Thèse Présentée pour l’obtention du grade de Docteur de l’Université de Haute-Alsace Ecole Doctorale : ED 222 - Sciences Chimiques Discipline : Chimie, Physique et Matériaux Présentée et soutenue publiquement par Franklin BAUER Le 30 novembre 2017 Une meilleure caractérisation des mécanismes d’action toxique à partir de la structure moléculaire. Thèse CIFRE Sous la Direction de : Directeur de thèse : Prof. Serge NEUNLIST Co-directeur de thèse : Dr. Samuel FOUCHARD Encadrée en entreprise par : Dr. Paul THOMAS Jury : Dr. Karine AUDOUZE, université Paris Diderot (Rapporteur) Dr. Patrice GONZALEZ, université de Bordeaux (Rapporteur) Prof. Jean-Philippe GODDARD, université de Haute-Alsace (Président) Prof. Eric PINELLI, université de Toulouse III Prof. Serge NEUNLIST, université de Haute-Alsace Dr. Samuel FOUCHARD, université de Haute-Alsace Dr. Paul THOMAS, KREATiS 3 Table des matières Table des figures .................................................................................................................. 6 Table des tableaux ............................................................................................................... 7 Liste des abréviations .......................................................................................................... 8 Remerciements ................................................................................................................. 10 Résumé de la thèse en anglais – Abstract ......................................................................... 11 1) Context and State of the Art ................................................................................. 11 2) Our contribution .................................................................................................... 12 3) Future prospects ................................................................................................... 14 Chapitre 1 : Introduction ................................................................................................... 16 1) QSARs et approches par analogie ......................................................................... 17 a) Principe de ces méthodes ................................................................................. 17 b) Contexte et raisons de leur utilisation .............................................................. 18 2) MechoAs vs MoAs ................................................................................................. 19 3) Différentes classifications et modèles de prédiction de MechoAs/MoAs ............................................................................................................. 20 a) Classifications et modèles sur les composés organiques en général ................ 20 b) Classifications et modèles sur des familles restreintes ..................................... 21 4) Objectifs de la thèse .............................................................................................. 22 Chapitre 2 : Revue bibliographique des mécanismes d’action ......................................... 24 1) Narcose .................................................................................................................. 25 a) Narcose non-polaire .......................................................................................... 25 b) Narcose polaire.................................................................................................. 28 2) Narcose des esters ou pronarcose ........................................................................ 29 3) Toxicité par réactivité avec formation d’adduits .................................................. 30 a) Electrophiles durs .............................................................................................. 31 b) Electrophiles mous ............................................................................................ 34 c) Générateurs de radicaux ................................................................................... 35 4) Toxicité pro-active ................................................................................................. 35 a) Métabolisation réduisant la toxicité ................................................................. 36 b) Métabolisation vers un réactif électrophile ...................................................... 39 c) Utilisation d’un cycle RedOx .............................................................................. 46 d) Métabolisation en perturbateur indirect d’enzyme ......................................... 47 e) Métabolisation en perturbateurs directs par docking ...................................... 48 2 5) Perturbation de l’environnement enzymatique.................................................... 49 a) Découplage de la phosphorylation oxydative par transport de protons ...................................................................................................................... 49 b) Acidification ou basification des cellules ........................................................... 51 6) Interaction directe dans un site de liaison ............................................................ 51 a) Inhibition de l’AcétylCholinEstérase .................................................................. 51 b) Ligands aux récepteurs de l’AcétylCholine ........................................................ 55 c) Perturbation du transport de la dopamine ....................................................... 56 d) Chélation des métaux ........................................................................................ 56 e) Inhibition du transport d’électrons du photosystème II ................................... 57 f) Modulation des canaux à ions ........................................................................... 58 g) Autres mécanismes ........................................................................................... 61 Chapitre 3 : Organisation des mécanismes d’action et discussion de certains mécanismes ....................................................................................................................... 66 1) Une nouvelle classification en mécanismes d’action toxique ............................... 67 2) MechoA des amines aliphatiques et ammoniums ................................................ 69 3) Discussion sur les modèles QSAR MechoA-spécifiques ........................................ 69 4) Discussion sur l’excès de toxicité observé pour les esters .................................... 71 5) Réactivité des γ-dicétones en tant qu’électrophiles durs ..................................... 74 6) Modélisation QSAR pour les découpleurs de la phosphorylation oxydative ....................................................................................................................... 74 7) Mécanisme responsable de la toxicité et corrosivité des acides et bases .............................................................................................................................. 75 Chapitre 4 : Développement d’un modèle de prédiction des MechoAs par approche quantique .......................................................................................................... 78 1) Introduction ........................................................................................................... 79 2) Publication ............................................................................................................. 80 A New classification algorithm based on Mechanisms of Action. ................................................. 80 Abstract ............................................................................................................................. 80 1. Introduction ............................................................................................................... 80 1.1. MechoA definitions ................................................................................................ 82 2. Materials and Methods .............................................................................................. 84 2.1. Literature data ....................................................................................................... 84 2.2. Computational methods ........................................................................................ 85 2.3. Classification algorithm .......................................................................................... 87 3. Results and discussion ............................................................................................... 90 4. Conclusions ................................................................................................................ 92 3 Acknowledgments ............................................................................................................. 93 References ......................................................................................................................... 93 3) Conclusion ............................................................................................................. 95 Chapitre 5 : Développement d’un modèle de prédiction des MechoAs par alertes structurales. ........................................................................................................... 96 1) Introduction ........................................................................................................... 97 2) Matériels et Méthodes .........................................................................................
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