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Faculté De Pharmacie FACULTÉ DE PHARMACIE École Doctorale en Sciences Pharmaceutiques SYNTHESIS OF CHIRAL VICINAL DIAMINES AND IN VITRO ANTICANCER PROPERTIES OF THEIR PLATINUM(II) COORDINATES Gilles BERGER Thèse présentée en vue de l’obtention du grade de Docteur en Sciences Biomédicales et Pharmaceutiques Promoteur Prof. François DUFRASNE, Laboratoire de Chimie Pharmaceutique Organique Composition du jury Prof. Jean-Michel Kauffmann, Faculté de Pharmacie, Université Libre de Bruxelles (Président) Prof. Franck Meyer, Faculté de Pharmacie, Université Libre de Bruxelles (Secrétaire) Prof. Michel Luhmer, Faculté des Sciences, Université Libre de Bruxelles Prof. Jacques Liévin, Faculté des Sciences, Université Libre de Bruxelles Prof. Ghanem-Elias Ghanem, Institut Jules Bordet, Université Libre de Bruxelles Prof. Sophie Bombard, Faculté de Médecine, Université Paris-Descartes Prof. Bernard Pirotte, Faculté de Médecine, Université de Liège Année académique 2013-2014 Acknowledgments ACKNOWLEDGMENTS This part of the work has been written in French… Si cette section apparaît en premier, elle n’en fut pas moins la dernière écrite, après la longue rédaction de la partie scientifique. Force est de constater qu’on n’en arrive pas là seul, mais bien grâce au précieux soutien de son entourage. Soutien indispensable à la préparation d’une thèse de doctorat, travail sympathique mais un peu long et éprouvant. J’essaierai de n’oublier personne. Je voudrais tout d’abord remercier mon chef de service, le Professeur Jean Nève. D’abord pour sa confiance accordée, moi qui revenais à l’Université quelques années après mon diplôme de Master, dans des circonstances particulières. Il m’a permis de revenir à cette science que j’aime tant, après des années difficiles. Ensuite pour sa sympathie et sa bonne humeur quasi-permanente, son soutien tout au long de mon parcours d’assistant et de doctorant. Travaillant dans un domaine relativement éloigné de mes préoccupations scientifiques quotidiennes, il me laissa la liberté dont j’avais besoin et que j’affectionne, mais fut souvent là en cas de pépin, quand j’avais besoin de lui pour m’appuyer. Vient naturellement ensuite mon Promoteur, le Professeur François Dufrasne. Les mêmes remarques quant à sa confiance accordée, bien entendu. François a quelque chose de particulier et de relativement attachant. Sous ses airs un peu papy et bonhomme, vous trouverez quelqu’un de posé, rigoureux et d’une honnêteté sans faille. C’est avec lui et Michel Gelbcke que je me suis formé à la pratique de la synthèse chimique. C’est aussi lui qui a suivi l’avancement de mes travaux de recherche, tout en me laissant également cette liberté dont j’ai besoin. Je me rappellerai l’agréable semaine passée avec François à Grenoble, pour un congrès de chimie. Merci François. Parlons aussi de Michel, puisque c’est lui qui m’a appris les rudiments de la synthèse organique en laboratoire, discipline fort différente de la synthèse sur papier. Personnage historique du bâtiment BC, son amour pour la chimie et la résonance magnétique nucléaire en fait un partenaire de choix pour quelque discussion matinale. Et oui, Michel est pensionné et ne vient que le matin. Merci pour son soutien et ses précieux conseils. Merci bien sûr aux autres membres du service de chimie pharmaceutique organique. Pierre et Cédric, le premier fut mon assistant et le second entama son travail de thèse en même temps que moi. Caroline et Damien, qui ont débuté leur parcours doctoral un peu après moi. Jalal et Iyas, mes collègues de bureau syriens et hauts en couleur. Florence, notre 3 Acknowledgments technicienne, avec qui j’ai donné nombre d’heures de travaux pratiques. Merci à eux pour leur bonne humeur et leur aide en cas de besoin. J’ai bien entendu été amené à rencontrer des chercheurs d’autres facultés lors de mon travail de thèse. Le premier fut Michel Luhmer, le directeur du centre d’instrumentation en résonance magnétique nucléaire. Ce fut un plaisir de travailler avec lui. J’ai commencé par suivre deux de ses cours que j’ai beaucoup appréciés. C’était cependant parfois un peu dur de 8 à 10 heures, je ne suis pas très matinal. J’ai rapidement utilisé la RMN pour mes recherches, avec un plaisir certain. J’aime bien la physique et il faut avouer que la RMN est belle. Michel est un scientifique attaché aux aspects fondamentaux des choses, à leurs bases physiques, aux équations. Je le suis aussi et j’en profite donc pour remercier deux professeurs dont j’ai suivi les enseignements il y a déjà une dizaine d’années, Robert Deltour et John Turner, qui ont tous deux développé mon goût pour la science. Le premier fut mon professeur de physique générale en première année. La vraie compréhension des choses simples à partir desquelles se développent un raisonnement plus complexe, la critique, la rigueur. Le second fut mon professeur de mécanique quantique en seconde année de chimie, lorsque je suivais les deux cursus en même temps. Si diverses raisons m’ont empêché de terminer mes études de chimie et de concrétiser mes rêves quantiques, j’espère me rattraper un peu avec cette thèse. Je fus émerveillé et surtout interpellé par cette nouvelle physique, en tous points différente et tout-à- fait déconcertante. Plus rien n’était réel, tout était mathématique: probabilités, opérateurs, valeurs propres et fonctions propres, espaces de Hilbert… Mais celle-là fonctionnait bel et bien au niveau atomique, monde obscur pour les lois de la mécanique classique. De cet étonnement est né le troisième chapitre du présent travail, élaboré à partir de calcul quantique sur ordinateur. A ce propos un grand merci à Michel Godefroid qui a relu la courte introduction à la théorie de la fonctionnelle de densité. Théorie en vogue grâce au développement de fonctionnelles d’échange et de corrélation modernes. Merci à Georges Destrée pour son aide quant à l’utilisation du cluster de calcul, Hydra. Un grand merci aussi à Jacky et Emilie. Je voudrais également remercier Luca Fusaro, Rita d’Orazio et Lidija Stefanoska, respectivement post-doctorant et techniciennes au laboratoire de RMN. Merci beaucoup à Rita et Lidija pour les innombrables tubes mis au passeur d’échantillons pendant ces cinq années de thèse. Merci à Luca pour son aide lors des manipulations sur le 400 MHz, notamment pour la RMN du 19F et du 195Pt, ainsi que pour sa sympathie. 4 Acknowledgments J’en profite bien entendu pour remercier Sophie Bombard qui m’a accueilli dans son laboratoire du 6ème arrondissement parisien. J’y ai appris à faire des gels d’électrophorèse, à manipuler des substances radioactives. J’y ai surtout trouvé quelqu’un de très sympa et pédagogue, avec qui je me suis bien entendu, aux qualités scientifiques indéniables. J’en profite pour demander pardon quant à mes innombrables étourderies, j’ai un problème certain en matière de distraction. Par ailleurs, le quartier latin, c’est joli. Ça me fait penser à Ferré et au soulèvement étudiant de 68, au jazz manouche. Il y a aussi là-bas la rue de Verneuil, siège de l’hôtel particulier de Gainsbourg. Un grand merci également à Franck Meyer, récemment engagé à l’Université pour assurer les enseignements de chimie et apporter un souffle nouveau à la recherche dans le service de chimie. L’arrivée d’un bon élément comme Franck est évidemment une excellente nouvelle. J’ai récemment entamé avec lui des travaux de recherche, j’espère que cela marquera le début d’une longue et fructueuse collaboration. Merci à Erik Goormaghtigh et à son équipe de chercheurs pour les expériences de spectroscopie infrarouge sur cellules, tout particulièrement merci à Régis et Allison. Merci aussi à Hélène, Robert et Véronique pour les tests sur cellules, notamment les MTT et la cytométrie en flux. Fluctuat nec mergitur… Devise de la ville de Paris ou refrain de Brassens, c’est selon. Mais une chose est certaine, merci aux copains. Merci à tous ceux qui m’ont soutenu dans les moments difficiles, merde aux autres. Que ce soient les amis d’enfance, comme Cédric et Jean-Yves, ou les amis un peu plus récents, comme Tom, Aurélien ou Geoffroy, votre présence a toujours été précieuse. Merci aussi aux amis de pharma, Clément, Emma, Laurent et les autres. Je repense avec nostalgie à cette période estudiantine, bercée d’insouciance, de soif de savoir et de bière. Non, ce n'était pas le Radeau de la Méduse, ce bateau… Merci à Marie, dont les grands yeux ont fait irruption dans ma vie depuis maintenant trois ans. Merci de me supporter, ça ne doit franchement pas être évident tous les jours avec mon caractère de cochon. Je vais terminer par ma famille, mes parents, mon frère. Leur indicible soutien est très certainement à l’origine de ce travail, car sans eux, les choses se seraient très probablement terminées autrement. Merci à ma grand-mère, ma tante, ma grand-tante de Mouscron. Papa, Maman, merci pour tout, il y a plus de trente-deux ans que vous êtes toujours là pour moi, que dire… 5 “A force de patience et d’inaction, j’ai pu dresser un hanneton.” S. Gainsbourg Table of Contents TABLE OF CONTENTS ACKNOWLEDGMENTS ....................................................................................................... 3 TABLE OF CONTENTS ........................................................................................................ 7 ABBREVIATIONS ................................................................................................................ 9 UNITS ..................................................................................................................................10 FIGURES, SCHEMES AND TABLES
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