Fluorine and Health. Molecular Imaging, Biomedical Materials by Alain Tressaud, Günter Haufe

By Alain Tressaud, Günter Haufe

Fluorine and well-being offers a serious multidisciplinary evaluate at the contribution of fluorinated compounds to solve the real worldwide factor of medicinal tracking and healthiness care. The concerned matters are prepared in 3 thematic components dedicated to Molecular Imaging, Biomedical fabrics and Pharmaceuticals.Initially the key-position of partly fluorinated low molecular weight compounds labelled both with the normal 19F-isotope for Magnetic Resonance Imaging (MRI) or labelled with the radioactive [18F]-isotope for Positron Emission Tomography (PET) is highlighted. either non-invasive equipment belong to the main difficult in vivo imaging options in oncology, neurology and in cardiology for the analysis of ailments having the top mortality within the industrialized countries.The manifold points of fluorinated biomaterials diversity from inorganic ceramics to perfluorinated natural molecules. Liquid perfluorocarbons are appropriate for oxygen shipping and as power breathing fuel providers, whereas fluorinated polymers are attached to the pathology of blood vessels. one other vital factor issues the appliance of hugely fluorinated beverages in ophthalmology. in addition, fluorine is an important hint aspect in bone mineral, dentine and the teeth teeth and is utilized for the prophylaxis and therapy of dental caries. a few of the origins of human publicity to fluoride species is precise to advertise a greater realizing of the impact of fluoride species on residing organisms.Medicinally suitable fluorinated molecules and their interactions with local proteins are the focus of the 3rd half. New molecules fluorinated in strategic place are an important for the improvement of prescription drugs with wanted motion and optimum pharmacological profile. one of the 1000's of advertised lively drug parts there are greater than one hundred fifty fluorinated compounds. The chapters will illustrate how the presence of fluorine atoms alters homes of bioactive compounds at a variety of biochemical steps, and probably facilitate its emergence as prescribed drugs. eventually the bogus power of a fluorinase, the 1st C-F bond forming enzyme, is summarized.

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2. 1. The pyridine series In the last decade the scope of nucleophilic radiofluorination has been open to heteroaromatic substitutions, particularly in the pyridine series [29,222–224], mainly promoted by the appearance of some important nicotinic receptor drug families, containing a fluoropyridine moiety. In stable-fluorine-19 chemistry one finds only a small number of examples of heteroaromatic nucleophilic fluorination leading to fluoropyridines and the like (fluoroquinolines, -isoquinolines, -naphthyridines and -pyridoquinolines).

18F MgCl (i) CH3(CH2)5CH2MgCl CO2Et Na+ (ii) (iii) CH3(CH2)5CH2-18F Et2OC CO2Et CO2Et Si N Si CO2Et Na+ 18F (iv) CO2Et H2N 18F Scheme 23. (i) [18F]FPyþÁCF3SO3À, THF, 5  C, 10 min; (ii) [18F]FPyþÁCF3SO3À, Et2O, 5  C, 10 min; (iii) [18F]FPyþÁCF3SO3À, THF, 0  C, 10 min; (iv) [18F]FPyþÁCF3SO3À, THF, RT, 60 min. N-[18F]Fluoropyridinium triflate reacts with alkyl- and arylmagnesium salts (Grignard reagents) as well as enolates (Scheme 23) to yield the corresponding radiofluorinated products, often in high radiochemical yields.

24 18F M (i) M = MgCl, Li MgBr 18F (i) 18F MgBr * (i) Me O S N O 18F Scheme 24. (i) N-[18F]Fluoro-N-endo-norbornyl-paratoluenesulphonamide À78  C, 5 min. " [18F]F + " (Ã) , Et2O, sp3-hybridised − LG + 18F Step 1 LG Step 2 LG sp2 18F sp2 Wheland intermediates Scheme 25. The arenium ion mechanism of electrophilic fluorination of aromatic rings via fluorodehydrogenation or fluorodemetallation reactions. OH OH HO NH2 CO2H HO 2 (i) 5 18F 6 NH2 CO2H 2-, 5- and 6-[18F]fluoro-L-DOPA Scheme 26. 5–15 min.

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