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Fluorene-Based Fluorescent Markers: New Insights in Synthesis And

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Fluorene-Based Fluorescent Markers: New Insights in Synthesis And Fluorene-based fluorescent markers : new insights in synthesis and applications into labeling of nucleic acids and imaging of cell membranes Janah Shaya To cite this version: Janah Shaya. Fluorene-based fluorescent markers : new insights in synthesis and applications into labeling of nucleic acids and imaging of cell membranes. Other. Université Côte d’Azur, 2016. English. NNT : 2016AZUR4066. tel-02003596 HAL Id: tel-02003596 https://tel.archives-ouvertes.fr/tel-02003596 Submitted on 1 Feb 2019 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. UNIVERSITE DE NICE‐SOPHIA ANTIPOLIS − UFR Sciences Ecole Doctorale de Sciences Fondamentales et Appliquées THESE Pour obtenir le titre de Docteur en Sciences de l'UNIVERSITE de Nice – Sophia Antipolis Discipline : Chimie Présentée et soutenue par Janah Shaya « Capteurs fluorescents à base de fluorène : nouvelles perspectives en synthèse et applications pour le marquage des acides nucléiques et en imagerie de la membrane cellulaire » « Fluorene‐based fluorescent markers; new insights in synthesis and applications into labeling of nucleic acids and imaging of cell membranes » Thèse dirigée par le Prof. Alain BURGER et co‐encadree par le Dr. Benoît Y. MICHEL Soutenue le 21 Septembre 2016 Jury: Pr. Demchenko Alexander Professeur, Académie Nationale Rapporteur des Sciences de l'Ukraine Pr. Smietana Michael Professeur, Université de Rapporteur Montpellier Dr. Jazzar Rodolphe Chercheur CNRS, Université de Rapporteur Californie Dr. Michel Y. Benoît Maître de conférences, Université Co‐encadrant Nice Sophia Antipolis de thèse Pr. Burger Alain Professeur, Université Nice Sophia Directeur de Antipolis thèse ﺇﻟﻰ "ﻟﺒﻨﺎﻧﻲ" ﻟﺒﻨﺎﻥ ﺟﺒﺮﺍﻥ ﻭﺧﻮﺭﻱ ﻭﻛﻞ ﻣﻦ ﻳﺤﻤﻴﻪ.... To my “Lebanon”, the country of Gibran and Corey, And everyone who keeps it safe…. A toi mon “Liban”, Le pays de Gibran et Corey, Et à tous ceux qui le protègent…. __________________________________________________________________________________________________________________ Acknowledgements First, I would like to express my sincere thankfulness to the “French ministry of education” and the “Doctoral school of Nice‐Sophia Antipolis university (ED‐SFA)” for offering me this Ph.D grant for three years. I am equally thankful to Pr. Alain Burger for the fruitful leadership of this thesis. In fact, Alain is present and evenly invested in all the work in his lab, especially the difficult starting of new projects like “my fluorenes”. His guidance, knowledge, resources, and ambition were indispensable. An in‐line thank you might go here to Dr. Benoit Michel for his useful contributions. He is one of few chemists I’ve met with an inspiring talent in the art of “organic synthesis”. Dr. Rachid Benhida has the portion of the lion especially in the front lines of this project. I owe him for his support and the 3‐year stay in the “molecules bioactives” group. I would also like to acknowledge all the permanent staff of our group and the ICN; in particular, the director of the ecole doctorale Dr. Elisabeth Taffin‐de‐Givenchy, Dr. Audrey Di Giorgio, Dr. Stephane Azouly and Dr. Sophie Poulain‐Martini for the teaching experience, Dr. Maria Duca, Dr. Luc Demange, Dr. Cyril Ronco, Dr. Guilhem Godeau, Dr. Thierry Darmanin for setting the example of a researcher for me, Dr. Christope Di Giorgio for all the synthesis advices, the director of the ICN Dr. Elisabet Duñach for the GCMS facilities, Dr. Lionel Massi for the mass spectrometry, Dr. Marc Gaysinski for the NMR spectroscopy, and Dr. Nadine Martinet for her tips and advices. The list of acknowledgments will continue and I hope I do not forget anyone as research is a collaborative effort and many people play a direct or indirect role; Dr. Anthony Martin for sharing his knowledge on catalysis and for the pleasant talks, Dr. Sylvain Antoniotti for his precious remarks on sustainable chemistry, Dr. Fabien Fontaine‐Vive for the pleasure of working with him on DFT calculations, and Prof. Nadia Patino for plenty of teachings and fun. Pr. Iyad karamé, Dr. AbdelRehman Sidani, Pr. Peter Goekjian, and Dr. Rodolphe Jazzar deserve to be appreciated for being influential chemists that have planted the first eagerness for this domain in me. Iyad is a person to whom I am deeply indebted. A big thank you goes also to Dominique Bonhomme (Domi) and Frederic Benailli (Fredo) for the coffee and work time we spent. I hope that our work together will be validated in publications the soonest. I have to warmly thank Pr. Alexander Demchenko, Pr. Michael Smietana, and Dr. Rodolphe Jazzar for revising this manuscript and being members of the thesis committee. I would likewise address the great team in Strassbourg for the warm, helpful, and productive welcoming in their lab where we performed the cell imaging; Pr. Yves Mely, Dr. Andrey Klymchenko, Dr. Mayeul Collot, and the young researchers there; Dr. Yosuke‐Niko, Bohdan, Dorian, Hassan, Iryna, Rajhan and others for the fun trips and nights we passed during my stay. Nice lab has a list of young researchers that enriched this journey with good memories as well: Florian, Gabreilla, Hamza, Alexandra, Hellene, Coralie, Antoine, Sokaina, Loraine, Anne, Lauri, Sasha, Oleg, Malika, Nelli, Cecile. I wish you all the best in your future endeavors. Few words to some should be mentioned: Cate; Sursum Corda ou Janah va… we really missed you in the ICN, Niko; it was a pleasure to share the same lab with you, Anh; you will be truly missed my 3 __________________________________________________________________________________________________________________ dearest, Mauro; you lightened up fluorescence a bit more dude. Merci également à Marie le grand prof. de français pour les produits qu'elle a fait au cours de M1 stage. I think I forgot Hella, not really! You will be remembered for long time. All the first translations, hang‐outs, fun, and shouting have spiced “Nice” stay. Assia also did her share in translations and joy, merci! Altogether with Diaa, Ilheme, and Najiba, we had a great deal of time and food that I will definitely miss. Dr. Ilheme, despite your early departure from the ICN, the short time was enough to reveal a chemist and person of high standards and a friend for life. Outside the lab, there are many people who had put up with me in all stages. They are a major highlight in my life. The Janwa; you witnessed it all and are still doing patiently, I will simply quote from your thesis: “Behind each work, there is a secret rider, you were always there”, see you soon in Strass. George; an ever‐lasting support and a melody for every occasion, laughing is the key of success as you say. kawsar; the chief of chiefs, for god’s sake we need to stop running and making rules; not everyone has your potential. Together, we made the perfect kG group of nice. Ramez; you left your space when you moved. Abed, Tharwat; travelling with you is beyond fun. Habeeb and Hawraa; you added a source of joy with our future chemist, Mariam. Finally Pascal; we will hopefully always meet or run away bro, I am so happy that I have met you. Back home, the gratitude can go endless and I still have too many experiments to do, so I will cut it short. Thanks for everyone who supported me when I decided to change careers. I am very lucky to have a family that trusts my choices without questioning. You are too many, but I love you all. Mostafa and Iman; you are my residence and comfort. Jinan; you did all what I have to do for years. You, Naim, and your three ugly musketeers are blessings. Suzan and Samah, your craziness makes you so special and we are proud of your success with each day passing, Roy, Iyad, and karam; you will be one of a kind (chemical) engineers, you know it. Jihan, Souaad, Makram, Fares, David, Osama, Wido…. Silvana; don’t get lost in Cuba, I can’t live without you all. Distance did not make some any less of great friends: Rawad, a real brother; we will keep on roaming and reach, we shared all the crazy and wisdom times, all the fun, joy, plans, and determination‐I hope you make it to my defense, Bilal, Bahaa; thanks for all and cheers, Naveen, Fadi, George, Anis, Samer, Dani, and the group leader in Dubai, khodr; here it is man, our chemistry is finally in action, Lamece the royal; I will sum up the 10 pages of jokes you make of me into one line of don’t stop because I will miss it, Jihan the one and only; from Lyon to Lebanon, and Marah; a real source of aspiration for many years, I will buy a house in Monaco and you will be invited. If anyone is forgotten, be sure it is for lack of time. I appreciate an equal list of people that I could not name. Finally, there is nothing better than quoting from the French Nobel Prize winner Jacques Monod: “In science, self‐satisfaction is death. Personal self‐satisfaction is the death of the scientist. Collective self‐satisfaction is the death of the research. It is restlessness, anxiety, dissatisfaction, agony of mind that nourish science.” So here it is, a small plan of an unsatisfied scientist who lost his first grant in a war back in 2006, and kept the same target of research till July 2016.
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