Fluorine and Health presents a critical multidisciplinary overview on the contribution of fluorinated compounds to resolve the important global issue of medicinal monitoring and health care. The involved subjects are organized in three thematic parts devoted to Molecular Imaging, Biomedical Materials and Pharmaceuticals.
Initially the key-position of partially fluorinated low molecular weight compounds labelled either with the natural 19F-isotope for Magnetic Resonance Imaging (MRI) or labelled with the radioactive [18F]-isotope for Positron Emission Tomography (PET) is highlighted. Both non-invasive methods belong to the most challenging in vivo imaging techniques in oncology, neurology and in cardiology for the diagnosis of diseases having the highest mortality in the industrialized countries.
The manifold facets of fluorinated biomaterials range from inorganic ceramics to perfluorinated organic molecules. Liquid perfluorocarbons are suitable for oxygen transport and as potential respiratory gas carriers, while fluorinated polymers are connected to the pathology of blood vessels. Another important issue concerns the application of highly fluorinated liquids in ophthalmology. Moreover, fluorine is an essential trace element in bone mineral, dentine and tooth enamel and is applied for the prophylaxis and treatment of dental caries. The various origins of human exposure to fluoride species is detailed to promote a better understanding of the effect of fluoride species on living organisms.
Medicinally relevant fluorinated molecules and their interactions with native proteins are the main focus of the third part. New molecules fluorinated in strategic position are crucial for the development of pharmaceuticals with desired action and optimal pharmacological profile. Among the hundreds of marketed active drug components there are more than 150 fluorinated compounds. The chapters will illustrate how the presence of fluorine atoms alters properties of bioactive compounds at various biochemical steps, and possibly facilitate its emergence as pharmaceuticals. Finally the synthetic potential of a fluorinase, the first C-F bond forming enzyme, is summarized.
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1. Fluorine-18 Chemistry for Molecular Imaging with Positron Emission Tomography
Frédéric Dollé, Dirk Roeda, Bertrand Kuhnast, and Marie-Claire Lasne
2. Application of 18F-PET Imaging for the Study of Alzheimer's Disease
Kjell Någren and Juha O. Rinne
3. 18F-Labeled PET-Tracers for Cardiological Imaging
Klaus Kopka, Stefan Wagner, Michael Schäfers, Andreas Faust, Otmar Schober, and Günter Haufe
4. [18F]-Labeled PET and PET/CT Compounds in Oncology
Ken Herrmann and Bernd Joachim Krause
5. Non-Invasive Physiology and Pharmacology Using 19F Magnetic Resonance
Jian-Xin Yu, Weina Cui, Dawen Zhao, and Ralph P. Mason
PART II: BIOMEDICAL MATERIALS
6. Fluoride-Based Bioceramics
Christian Rey, Christèle Combes, Christophe Drouet, and Hocine Sfihi
7. Fluoride in Dentistry and Dental Restoratives
John W. Nicholson and Beata Czarnecka
8. Fluorinated Biomaterials for Cardiovascular Surgery
Charles Baquey, Marie-Christine Durrieu, and Robert G. Guidoin
9. Fluorinated Molecules in Eye Surgery: Experimental and Clinical Benefit of a Heavy Silicone Oil Oxane Hd® (Mixture of Silicone Oil and RMN3 Fluorine Olefin) in the Treatment of Retinal Detachment
I. Rico-Lattes, J. C. Quintyn, V. Pagot-Mathis, X. Benouaich, and A. Mathis
10. Biocompatibility of Highly Fluorinated Liquids Used in Ophthalmic Surgery
Dirk-Henning Menz and Joachim H. Dresp
11. Perfluorochemical-Based Oxygen Therapeutics, Contrast Agents, and Beyond
Marie Pierre Krafft and Jean G. Riess
12. Exposure of Humans to Fluorine and Its Assessment
PART III: PHARMACEUTICALS
13. Biological Impacts of Fluorination: Pharmaceuticals Based on Natural Products
Jean-Pierre Bégué and Danièle Bonnet-Delpon
14. Synthesis and Pharmacological Properties of Fluorinated Prostanoids
15. Synthesis and Biochemical Evaluation of Fluorinated Monoamine Oxidase Inhibitors
Kenneth L. Kirk, Shinichi Yoshida, and Günter Haufe
16. Fluoroolefin Dipeptide Isosteres: Structure, Syntheses, and Applications
John T. Welch
17. Molecular Interactions of Fluorinated Amino Acids in a Native Polypeptide Environment
Mario Salwiczek, Christian Jäckel, and Beate Koksch
18. Biological Fluorination in Streptomyces cattleya: The Fluorinase
Hai Deng, Fang-Lu Huang, James H. Naismith, David O′Hagan, Jonathan B. Spencer, and Xiaofeng Zhu
Alain Tressaud is Emeritus Research Director at ICMCB-CNRS, Bordeaux University. He is President of the European Academy of Science in Brussels and member of several European academies. He founded and chaired the French Network on Fluorine Chemistry, sponsored by CNRS, until 2008. He has received several awards, including the CEA Award of French Academy of Sciences (2008), the Fluorine Award of the American Chemical Society (2011), and the International Henri Moissan Prize (2013). His scientific interest covers various fields, including synthesis, physical chemical characterizations, applications in fluorine chemistry, solid state chemistry, and materials sciences. His work also deals with surface modification of materials and intercalation chemistry. Professor Tressaud's scientific production includes more than 360 papers in international journals, 20 book chapter contributions, and 12 internationalized patents. He has also edited several books in his role as editor-in-chief of the series "Advances in Fluorine Science (2006) and "Progress in Fluorine Science (2016) with Elsevier.
Gunter Haufe Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, D-48149 Münster, Germany.
Günter Haufe graduated from the University of Leipzig (Germany) with a Diploma degree in 1972 and a Dr. rer. nat. in 1975 both with Professor Manfred Mühlstädt. After basic military service he started his independent scientific career and did a Habilitation and venia legendi in Leipzig (1985). In 1986 he worked as a Research Fellow of Centre National de la Recherche Scientifique (CNRS) with André Laurent at the Université Lyon I (France) for 6 months, and as a visiting scientist with Jakko Paasivirta at the University of Jyväskylä (Finland). From 1988-1991 he was an Associate Professor (Docent) of Bioorganic Chemistry at the University of Leipzig before he was appointed at his present position as a Professor of Organic Chemistry at the University of Münster (Germany). Guest Professorships led him to Lyon, Poznan, Rouen, Valencia, Nagoya, Shanghai and to the University of Florida, Gainesville (USA) as a Paul Tarrant Visiting Professor. He was awarded with the "Friedrich-Wöhler-Preis in 1985 and elected as a member of the European Academy of Sciences in 2015. From 2008-2010 he served as a Chair of the group of German fluorine chemists within the German Chemical Society. He published a book on "Alicyclic Chemistry" together with Gerhard Mann (1989) and edited a monograph "Fluorine and Health" together with Alain Tressaud (2008). He was an Associate Editor of "Advances in Fluorine Science" and is a Regional Editor of the Journal of Fluorine Chemistry since 2008.
His research interest span from Organofluorine Chemistry, particularly fluorination methodology, selective synthesis of fluorinated analogues of natural products and 18F-tracers for the Positron-Emission-Tomography, via Preparative Organic Chemistry including total synthesis of natural products, to enzymatic methods for the preparation of organic compounds.