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Development of a Novel Photosensitizer for Photodynamic Therapy of Cancer

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Development of a Novel Photosensitizer for Photodynamic Therapy of Cancer Luís Gabriel Borges Rocha Development of a novel photosensitizer for Photodynamic Therapy of cancer Tese de doutoramento em Ciências Farmacêuticas, especialidade em Biotecnologia Farmacêutica, orientada pelo Professor Doutor Sérgio Simões e pelo Professor Doutor Luís G. Arnaut e apresentada à Faculdade de Farmácia da Universidade de Coimbra Outubro de 2015 Luís Gabriel Borges Rocha Development of a novel photosensitizer for Photodynamic Therapy of cancer 2015 FACULDADE DE FARMÁCIA DA UNIVERSIDADE DE COIMBRA Tese de doutoramento em Ciências Farmacêuticas, especialidade em Biotecnologia Farmacêutica, apresentada à Faculdade de Farmácia da Universidade de Coimbra Doctoral thesis in Pharmaceutical Sciences, specialty in Pharmaceutical Biotechnology, presented to the Faculty of Pharmacy of the University of Coimbra. Orientadores Científicos / Scientific Supervisors: Professor Doutor Sérgio Simões Faculdade de Farmácia da Universidade de Coimbra Professor Doutor Luís G. Arnaut Faculdade de Ciências e Tecnologia da Universidade de Coimbra The studies presented in this thesis were performed at Bluepharma – Indústria Farmacêutica, SA, Chemistry Department of the Faculty of Sciences and Technology of the University of Coimbra, Centre for Neuroscience and Cell Biology of the University of Coimbra and Instituto Nacional de Investigação Agrária e Veterinária in Santarém, Portugal. The work was funded by Bluepharma – Indústria Farmacêutica, SA and Luzitin, SA, which received additional financial support from the National Strategic Reference Framework’s Programme (QREN) nº 5356, from November 2010 until October 2013. Para a Sónia, Beatriz e Rodrigo, as estrelas mais brilhantes no meu Universo! Science is the only light in the dark paths of the unknown. Let there be light Genesis 1:3 Table of Contents Agradecimentos -----------------------------------------------------------------------------------------------iii Thesis Abstract -------------------------------------------------------------------------------------------------v Resumo da Tese ----------------------------------------------------------------------------------------------vii List of Abbreviations ------------------------------------------------------------------------------------------xi List of Figures -- ------------------------------------------------------------------------------------------------xv List of Tables --------------------------------------------------------------------------------------------------xvii Chapter 1 – General Introduction ------------------------------------------------------------------------------------ 3 1.1. Preamble ---------------------------------------------------------------------------------------------------------- 4 1.2. Challenges in cancer therapy – Photodynamic Therapy as an alternative for cancer treatment --------------------------------------------------------------------------------------------------------------- 5 1.3. History of Photodynamic Therapy --------------------------------------------------------------------------- 6 1.4. Mechanism of action ------------------------------------------------------------------------------------------- 7 1.5. Photodynamic Therapy in clinical practice -------------------------------------------------------------- 10 1.6. Advantages and limitations --------------------------------------------------------------------------------- 11 1.7. Light, photosensitizers and oxygen ----------------------------------------------------------------------- 13 1.7.1. Light --------------------------------------------------------------------------------------------------------- 13 1.7.2. Photosensitizers ------------------------------------------------------------------------------------------ 15 1.7.3. Oxygen------------------------------------------------------------------------------------------------------ 17 1.8. Photosensitizer biodistribution and intracellular localization -------------------------------------- 20 1.8.1. Topical application -------------------------------------------------------------------------------------- 20 1.8.2. Systemic administration ------------------------------------------------------------------------------- 21 1.8.3. Intracellular localization -------------------------------------------------------------------------------- 22 1.9. Mechanisms of cell death ----------------------------------------------------------------------------------- 23 1.9.1. Autophagy ------------------------------------------------------------------------------------------------- 23 1.9.2. Apoptosis -------------------------------------------------------------------------------------------------- 24 1.9.3. Necrosis ---------------------------------------------------------------------------------------------------- 24 1.10. Mechanisms of resistance --------------------------------------------------------------------------------- 25 1.11. PDT dosimetry ------------------------------------------------------------------------------------------------ 26 1.12. Photodynamic threshold dose and effective treatment depth ----------------------------------- 27 1.13. Modes of action of Photodynamic Therapy ----------------------------------------------------------- 28 1.13.1. Effects on tumour cells ------------------------------------------------------------------------------- 28 1.13.2. Effects on blood vessels ------------------------------------------------------------------------------ 29 1.13.3. Effects on the immune system ---------------------------------------------------------------------- 30 i 1.14. Recent developments --------------------------------------------------------------------------------------- 33 1.15. Development of redaporfin for PDT of cancer -------------------------------------------------------- 35 1.15.1. Project context ------------------------------------------------------------------------------------------ 37 1.16. Objectives ------------------------------------------------------------------------------------------------------ 39 Chapter 2 – In vitro Biological Activity ----------------------------------------------------------------------------- 43 2.1. Abstract ---------------------------------------------------------------------------------------------------------- 44 2.2. Introduction ----------------------------------------------------------------------------------------------------- 44 2.3. Material and methods ---------------------------------------------------------------------------------------- 45 2.4. Results and discussion ---------------------------------------------------------------------------------------- 49 2.5. Conclusion ------------------------------------------------------------------------------------------------------- 53 Chapter 3 – Pharmaceutical Development and Proof-of-Concept ----------------------------------------- 57 3.1. Abstract ---------------------------------------------------------------------------------------------------------- 58 3.2. Introduction ----------------------------------------------------------------------------------------------------- 58 3.3. Materials and methods --------------------------------------------------------------------------------------- 60 3.4. Results and discussion ---------------------------------------------------------------------------------------- 64 3.5. Conclusion ------------------------------------------------------------------------------------------------------- 73 Chapter 4 – Nonclinical Safety Evaluation ------------------------------------------------------------------------ 79 4.1. Abstract ---------------------------------------------------------------------------------------------------------- 80 4.2. Introduction ----------------------------------------------------------------------------------------------------- 80 4.3. Materials and methods --------------------------------------------------------------------------------------- 81 4.4. Results and discussion ---------------------------------------------------------------------------------------- 86 4.5. Conclusion ------------------------------------------------------------------------------------------------------- 91 Chapter 5 – Towards a clinical protocol --------------------------------------------------------------------------- 95 5.1. Abstract ---------------------------------------------------------------------------------------------------------- 96 5.2. Introduction ----------------------------------------------------------------------------------------------------- 96 5.3. Materials and methods --------------------------------------------------------------------------------------- 97 5.4. Results ---------------------------------------------------------------------------------------------------------- 101 5.5. Discussion------------------------------------------------------------------------------------------------------ 105 5.6. Conclusion ----------------------------------------------------------------------------------------------------- 108 Chapter 6 – General Conclusion and Future Perspectives -------------------------------------------------- 111 7.1. References ----------------------------------------------------------------------------------------------------- 115 ii Agradecimentos Pessoalmente, este trabalho representa o ponto mais alto de uma fascinante viagem que teve início no já longínquo ano de 2006. A todos os que durante este trajeto contribuíram de forma construtiva para o resultado final, quero manifestar
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