Elsevier S & T

Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals

Tressaud, Alain; Haufe, Günter

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Table of contents

Cover
Contentsv
Contributorsix
Prefacexi
Part I: Molecular Imaging1
Chapter 1: Fluorine-18 Chemistry for Molecular Imaging with Positron Emission Tomography3
1. Introduction4
2. The radionuclide fluorine-18 and some general considerations concerning short-lived positron emit5
2.1. The position of fluorine-18 among short-lived positron emitters for PET5
2.2. Design of radiotracers and radiopharmaceuticals labelled with a short-lived positron emitter:7
2.3. Challenges in radiochemistry with short- lived. positron emitters, including fluorine-188
2.4. Fluorine-18 production10
2.5. Methods of radiofluorination11
2.6. Early fluorine-18-labelled precursors12
3. Electrophilic radiofluorination14
3.1. Preparation of electrophilic fluorination reagents15
3.1.1. Molecular[18F]fluorine15
3.1.2. Trifluoromethyl [18F]hypofluorite15
3.1.3. Acetyl [18F]hypofluorite15
3.1.4. Perchloryl [18F]fluoride16
3.1.5. Xenon di[18F]fluoride16
3.1.6. 1-[18F]Fluoro-2-pyridone17
3.1.7. N-[18F]Fluoropyridinium triflate17
3.1.8. N-[18F]Fluoro-N-alkylsulphonamides17
3.1.9. Bromo [18F]fluoride18
3.2. Fluorination of double-bond structures18
3.2.1. Fluorination of alkenes18
3.2.2. Fluorination of enol structures21
3.3. Fluorination of carbanions22
3.4. Fluorination of aromatic rings (other than via carbanions)23
3.4.1. Fluorodehydrogenation24
3.4.2. Fluorodemetallation25
4. Nucleophilic radiofluorination28
4.1. Preparation of reactive [18F]fluoride anion28
4.2. Nucleophilic aliphatic substitution29
4.2.1. Basic principles29
4.2.2. Preparation of simple [18F]fluoroalkyl-type molecular building blocks and some applications30
4.2.3. One-step synthesis of a radiopharmaceutical involving an aliphatic nucleophilic fluorination32
4.2.4. Multi-step synthesis of a radiopharmaceutical involving an aliphatic nucleophilic fluorinatio32
4.3. Nucleophilic aromatic substitution35
4.3.1. Homoaromatic series35
4.3.2. Heteroaromatic series41
5. Enzymatic carbon-[18f]fluorine bond formation43
6. The particular case of macromolecule labelling with fluorine-1845
6.1. Reagents for the fluorine-18 labelling of peptides and proteins45
6.2. Reagents for the fluorine-18 labelling of oligonucleotides48
7. Conclusion and perspectives49
References50
Note from the Editors65
Chapter 2: Application of 18F-PET Imaging for the Study of Alzheimer's Disease67
1. Introduction68
2. PET and SPECT imaging in AD69
2.1. Special features of 18F-radiopharmaceuticals69
2.2. Glucose metabolism and blood flow70
2.3. Serotonergic system72
2.4. Dopaminergic system73
2.5. Cholinergic system74
2.6. Histamine and benzodiazepine receptors76
2.7. Amyloid deposits77
3. Conclusions78
References79
Note from the Editors84
Chapter 3: 18F-Labeled PET-T racers for Cardiological Imaging85
1. Molecular imaging of the myocardium86
1.1. Background86
1.2. 2-Deoxy-2-[18F]fluoro-D-glucose ([18F]FDG)87
1.2.1. Mechanism of accumulation in myocytes87
1.2.2. Radiosynthesis88
1.3. Fatty acids89
2. Molecular imaging of vessels91
2.1. Atherosclerosis91
2.2. Endothelin-system94
2.3. Perfusion96
3. Innervation99
3.1. Sympathetic and parasympathetic innervation99
3.2. beta-Adrenoceptors100
3.3. 18F-labeled radioligands for PET imaging of beta-adrenoceptors106
3.3.1. [18F]Fluoroacetone as radiolabeling building block106
3.3.2. [18F]Fluoroisopropyl derivatives as radiolabeling building blocks109
3.3.3. [18F]Fluoroethyl derivatives as radiolabeling building blocks111
3.4. alpha-Adrenoceptors113
3.5. Muscarinic acetylcholine receptors113
3.6. Norepinephrine transporter and vesicular monoamine transporter118
4. Summary and perspectives125
Annex: 18F-labeled PET-tracers for cardiological imaging „ update126
Acknowledgments127
References128
Note from the Editors139
Chapter 4: [18F]-Labeled PET and PET/CT Compounds in Oncology141
1. Introduction142
2. [18F]-FDG-PET and -PET/CT in oncology144
2.1. Main indications of [18F]-FDG-PET and -PET/CT144
2.1.1. Colorectal cancer146
2.1.2. Lung cancer153
2.1.3. Lymphoma155
2.1.4. Breast cancer157
2.1.5. Esophageal cancer159
2.2. Therapy monitoring with [18F]-FDG-PET and [18F]-FDG-PET/CT162
2.2.1. Gastrointestinal tract (GI)163
2.2.2. Lung cancer166
2.2.3. Lymphoma167
2.2.4. Gastrointestinal stromal tumors (GIST)167
2.2.5. Head and neck168
2.2.6. Breast cancer168
2.2.7. Ovarian cancer168
2.3. Methodical considerations and limitations169
3. Innovative [18F] fluorine-based radiotracers170
3.1. Molecular imaging of proliferation with 3'-deoxy-3'-[18F]-fluorothymidine170
3.2. PET/CT studies of tumor hypoxia173
3.3. [18F]-Galacto-RGD-PET: Imaging of alphavbeta3 integrin expression175
3.4. [18F]-Fluorocholine-PET: Imaging of prostate cancer176
3.4.1. Biochemical rationale176
3.4.2. Compounds, biodistribution, and imaging177
3.4.3. Clinical studies178
3.5. [18F]-Fluoride-PET: Imaging of bone metastases178
3.6. [18F]FET-PET: Imaging with amino acids179
3.7. [18F]Fluorodopa-PET: Imaging with amino precursors181
Acknowledgments182
References182
Note from the Editors196
Chapter 5: Non-Invasive Physiology and Pharmacology Using 19F Magnetic Resonance197
1. Introduction198
1.1. Context and perspective199
1.2. 19F as an in vivo NMR probe201
2. 19F NMR for pharmacology215
2.1. Cancer chemotherapeutics216
2.1.1. Fluoropyrimidines216
2.1.2. Other anticancer drugs217
2.2. Other drugs218
3. Active reporter molecules220
3.1. Physical interactions220
3.1.1. In vivo oximetry220
3.1.2. pH231
3.1.3. Metal ions235
3.1.4. Caveats242
3.2. Chemical interactions243
3.2.1. Metabolism of FDG243
3.2.2. Hypoxia244
3.2.3. Enzyme reporters245
4. Passive reporter molecules252
5. Potential innovations and improvements253
6. Conclusions253
Acknowledgments254
References254
Part II: Biomedical Materials277
Chapter 6: Fluoride-Based Bioceramics279
1. Introduction281
2. Overview of bioceramics and related biomaterials incorporating fluoride ions281
3. Fluorapatite and fluoridated apatites: Structure and characterisation284
3.1. Crystal structure of stoichiometric fluorapatite284
3.2. Substituted fluoridated apatites286
3.3. Physico-chemical characterisation of fluoridated apatites288
3.3.1. X-ray diffraction288
3.3.2. FTIR spectroscopy289
3.3.3. Solid-state NMR290
3.3.4. Difficulties related to the characterisation of fluoridated apatites296
4. Physico-chemical properties of fluoridated apatites296
4.1. Dissolution properties of fluoridated apatites296
4.2. Fluoridation reactions297
4.3. Thermal stability298
4.4. Thermodynamic characteristics299
4.5. Surface characteristics299
4.5.1. Surface energy299
4.5.2. Surface charge300
4.5.3. Adsorption properties300
4.6. Fluoridation effects300
4.7. Mechanical properties of fluoridated apatite ceramics301
5. Fluor-containing glasses and cements302
5.1. Fluor-containing glasses302
5.2. Fluoridated cements305
6. Preparation and synthesis routes of fluoride- containing apatites306
6.1. High-temperature methods306
6.1.1. Solid–gas reaction306
6.1.2. Pyrolysis method307
6.1.3. Crystal growth method307
6.2. Low-temperature methods308
6.2.1. Hydrolysis method308
6.2.2. Precipitation method308
6.2.3. Exchange and/or dissolution–reprecipitation reactions309
6.2.4. Sol-gel method310
6.2.5. Crystal growth method310
7. Processing techniques for fluoride-containing bioceramics311
7.1. Processing of massive bioceramics containing fluoride311
7.2. Fluoride-containing bioceramic coatings312
7.2.1. High-energy processing312
7.2.2. Solution-mediated processing314
8. Fluoride ions in biological apatites316
9. Biological properties of fluoride-containing bioceramics319
9.1. Biological properties of fluoride ions in solution319
9.1.1. Effect of fluoride ion on mineralising cells319
9.1.2. Effect of the fluoride ion on osteoclasts319
9.1.3. Effect of fluoride ions on bacteria320
9.1.4. Other alterations in biological fluids related to fluoride ions321
9.2. Effect of fluoride-containing substrates on bone cells321
9.2.1. Osteoblast cells321
9.2.2. Osteoclast cells321
10. Conclusion322
References322
Note from the Editors331
Chapter 7: Fluoride in Dentistry and Dental Restoratives333
1. Introduction334
2. Fluoride in dentistry335
2.1. The importance of fluoride in dental health335
2.1.1. Fluoride in dentistry335
2.1.2. Demineralisation/remineralisation behaviour of the tooth surface338
2.1.3. Possible antimicrobial effect of fluoride339
2.2. Interaction of fluoride with hydroxyapatite340
2.2.1. Basic chemistry340
2.2.2. Fluoride and oral health: practical aspects343
2.3. Adverse effects of fluoride344
2.3.1. Fluorosis344
2.3.2. Potential systemic effects345
3. Methods of delivering fluoride347
3.1. Drinking water347
3.2. Salt and milk350
3.3. Dentifrices351
3.4. Fluoride mouthrinses353
3.5. Topical fluoride applications354
3.5.1. Gels354
3.5.2. Varnishes355
3.6. Fluoride-releasing restorative materials355
3.6.1. Glass-ionomers356
3.6.2. Resin-modified glass-ionomers361
3.6.3. Compomers362
3.6.4. Fluoride-containing composite resins364
4. Conclusions365
References366
Note from the Editors378
Chapter 8: Fluorinated Biomaterials for Cardiovascular Surgery379
1. Introduction380
2. Blood-vessel wall relationships (interactions of flowing blood with the vessel/vascular prosthesi381
2.1. Role of the surface free energy or surface tension381
2.2. Role of electrical parameters381
2.3. Scenario for blood-material interactions382
2.4. Role of dynamic factors384
2.5. Role of the morphology385
3. Requirements for a cardiovascular biomaterial386
4. From polytetrafluoroethylene to microporous teflon-based vascular prostheses388
4.1. State of the art related to vessel repair or replacement: Evolution and role of PTFE389
4.2. How to improve the functional patency of ePTFE-based prostheses?392
4.3. Chemical modifications of fluorinated polymers: A way to the improvement of their haemocompatib394
4.3.1. PTFE case394
4.3.2. PVDF case396
4.3.3. P(VDF-HFP) case401
5. Conclusions402
References404
Note from the Editors406
Chapter 9: Fluorinated Molecules in Eye Surgery: Experimental and Clinical Benefit of a Heavy Silico407
1. Introduction407
2. State of the art409
3. Synthesis of RMN3412
4. Biocompatibility of RMN3 and Oxane Hdregs413
5. Clinical study with Oxane Hdregs415
6. Conclusion417
References
Note from the Editors420
Chapter 10: Biocompatibility of Highly Fluorinated Liquids Used in Ophthalmic Surgery421
1. Introduction422
1.1. Anatomy of the human eye422
1.2. Vitreoretinal diseases423
1.3. Vitreoretinal surgery424
1.4. The particularity of the use of highly fluorinated liquids as ocular endotamponades425
2. Biocompatibility425
2.1. Perfluorooctane and perfluorodecalin427
2.2. New ocular endotamponades428
2.3. Biocompatibility test scheme adjusted for FCLs for ophthalmic use431
2.3.1. Toxicological tests431
2.3.2. Modified test procedures for FCLs433
2.4. Evaluation of undesirable local effects of ocular endotamponades435
2.4.1. Effects of the high density435
2.4.2. Oxygen content436
2.4.3. Effects based on physicochemical behaviours436
2.4.4. Effects based on the structure437
2.4.5. Shape of the droplet/contact angle439
2.4.6. Effect of impurities440
3. New developments441
References443
Note from the Editors445
Chapter 11: Perfluorochemical-Based Oxygen Therapeutics, Contrast Agents, and Beyond447
1. Introduction448
1.1. Brief reminder of basic properties of perfluorocarbons relevant to biomedical uses448
1.2. Perfluorocarbons: biocompatibility and environmental issues451
2. Oxygen Transport to Tissues452
2.1. Challenges in the development of a PFC-based oxygen carrier454
2.2. Product development status455
3. Improving Diagnosis
3.1. Development of micron-size injectable gas bubbles as contrast agents for improved us imaging447
3.1.1. The challenges: stabilizing microbubbles447
3.1.2. Osmotic stabilization of micron-size bubbles using a perfluorochemical447
3.1.3. Products and status447
3.1.4. Prospects447
3.2. Targeted particles for molecular imaging using US and magnetic resonance
4. Perfluorocarbons as Drugs and Drug Delivery Systems
4.1. Lung ventilation
4.2. Lung-surfactant replacement
4.4. Drug and gene delivery
5. Surgical Aids
6. Research Tools for the Life Sciences
6.1. Abiotic tags for controlled recognition, selection, and pairing of biopolymers474
6.2. "Abiotic " environments-"super-nonpolar " fluorous compartments for segregation and confinemen476
6.3. Tools for nanogram-scale bioassays and protein crystallization478
7. Conclusions and Perspectives
References479
Note from the Editors479
Chapter 12: Exposure of Humans to Fluorine and Its Assessment487
1. Introduction
2. Fluorine in the environment
2.1. Fluoride in the lithosphere491
2.2. Fluoride in air
2.3. Fluoride in natural waters492
3. Essentiality of fluoride494
4. Adverse effects of fluoride on humans495
4.1. Chronic toxicity495
4.1.1. Dental or enamel fluorosis496
4.1.2. Skeletal fluorosis497
4.2. Acute toxicity498
5. Bioavailability of fluoride499
6. Absorption, metabolism and excretion of fluoride500
6.1. Plasma fluoride501
6.2. Tissue fluoride501
6.3. Fluoride in placenta and foetus502
6.4. Elimination of fluoride502
6.4.1. Excretion via the kidneys and urine503
6.4.2. Excretion via faeces, saliva and sweat503
6.4.3. Excretion via breast milk503
7. Biomarkers of fluoride exposure and their status503
7.1. Plasma, saliva and urine as contemporary markers504
7.2. Nails and hair as recent markers504
7.3. Calcified tissues as historical markers505
8. Fluoride in diet, fluoride supplements, dental products and fluoridated salt and milk505
8.1. Drinking water and beverages505
8.1.1. Concentration of fluoride in drinking water505
8.1.2. Concentration of fluoride in beverages507
8.2. Milk and baby formulas508
8.3. Food509
8.4. Dietary supplements514
8.5. Dental products514
9. Fluoride intake515
9.1. Fluoride intake in adults516
9.2. Fluoride intake in children516
9.2.1. Fluoride intake from diet521
9.2.2. Fluoride intake from fluoride-containing toothpastes521
9.2.3. Fluoride intake from fluoride-containing supplements529
9.2.4. Estimated total intake of fluoride in children530
10. Analytical methods for fluorine532
10.1. Sample pre-treatment procedures533
10.2. Analytical methods for determining fluorine533
10.3. Determining fluorine in specific types of materials534
10.3.1. Fluorine in environmental media534
10.3.2. Fluorine in biological tissues, fluids and related materials535
10.3.3. Fluorine in fluoride supplements and dental products535
11. Indicators for estimating requirements for fluoride535
12. AI of fluoride536
13. Conclusions - enough or too much fluoride?537
Appendix: List of acronyms539
References539
Note from the Editors549
Part III: Pharmaceuticals551
Chapter 13: Biological Impacts of Fluorination: Pharmaceuticals Based on Natural Products553
1. Introduction554
2. Biological impact of fluorination554
2.1. Affinity for the macromolecule target555
2.1.1. Steric effects556
2.1.2. Conformational changes557
2.1.3. Dipolar interactions and electric field557
2.1.4. Hydrogen bond558
2.1.5. pKa of amines561
2.1.6. Fluorous interactions562
2.2. Absorption563
2.2.1. Lipophilicity563
2.2.2. pKa and solubility564
2.3. Metabolism566
2.3.1. Oxidative metabolism567
2.3.2. Hydrolytic metabolism570
2.4. Modification of the chemical reactivity: Conception of enzyme inhibitors572
2.4.1. Analogue of substrates as inhibitor572
2.4.2. Inhibition by stabilisation or destabilisation of intermediates of biological processes574
2.4.3. Irreversible inhibition with based-mechanism inhibitors (suicide-substrates)575
3. Fluorinated pharmaceuticals based on natural products577
3.1. Nucleosides and carbohydrates577
3.1.1. Inhibitors of the thymidylate synthase578
3.1.2. Inhibitors of RDPR and DNA polymerase580
3.2. Alkaloids585
3.2.1. Vinca alkaloids585
3.2.2. Camptothecin587
3.3. Lignans588
3.3.1. Podophyllotoxin588
3.4. Anthracyclines589
3.5. Macrolides590
3.5.1. Erythromycin590
3.5.2. Epothilones591
3.6. Steroids593
3.6.1. Corticosteroids593
3.6.2. Fluorosteroids acting on steroid hormone receptors600
3.6.3. Other fluorinated steroid drugs601
3.6.4. Vitamin D3 metabolites603
3.7. Prostanoids606
3.8. Terpenes608
3.8.1. Artemisinin608
3.9. Amino acids610
4. Conclusion611
References611
Chapter 14: Synthesis and Pharmacological Properties of Fluorinated Prostanoids623
1. Introduction624
1.1. Biosynthesis and metabolism of prostanoids624
1.2. Physiological properties of prostanoids and their receptors626
1.3. Historical background of fluorinated prostanoids research628
2. PGE Derivatives630
2.1. 13,14-dihydro-15-keto-PGE derivative630
2.2. EP1 receptor antagonist632
2.3. EP2 receptor agonist635
2.4. EP4 receptor agonist636
3. PGF derivatives637
3.1. FP receptor agonist637
3.2. FP receptor antagonist641
4. PGD derivatives642
4.1. DP receptor agonist and antagonist642
4.2. CRTH2 receptor agonist644
4.3. CRTH2 receptor antagonist644
5. PGI derivatives646
5.1. IP receptor agonist646
6. Concluding remarks649
Acknowledments652
References652
Chapter 15: Synthesis and Biochemical Evaluation of Fluorinated Monoamine Oxidase Inhibitors661
1. Introduction662
1.1. Amine oxidases662
1.1.1. Monoamine oxidases (EC 1.4.3.4)662
1.1.2. Polyamine oxidase (EC 1.4.3.4)664
1.1.3. Semicarbazide-sensitive amine oxidases (EC 1.4.3.6)664
1.2. Drugs targeting amine oxidases664
1.2.1. MAO inhibitors664
1.2.2. SSAO inhibitors665
1.3. Fluorine in drug design665
2. Ring-fluorinated MAO inhibitors666
2.1. Fluorine-substituted benzylamines and 2-phenylethylamines666
2.2. 4-Fluorotranylcypromine669
2.3. Aryl-N-aminoethylamide derivatives, for example, Ro-41-1049 and Ro-16-6491670
3. Aromatic side chain-fluorinated MAO and SSAO inhibitors671
3.1. beta,beta-Difluorinated phenethylamines672
3.2. Fluoroallylamines as irreversible MAO inhibitors672
3.3. Haloallylamines as SSAO inhibitors673
3.4. Allyl hydrazines as SSAO inhibitors674
3.5. Fluorinated aryl-oxazolidinone derivatives, for example, befloxatone674
3.6. Fluorinated 5H-indeno[1,2-c]pyridazin-5-one MAO B-selective inhibitors675
4. Fluorinated MAO inhibitors as PET-scanning agents676
4.1. Fluorinated amine oxidase inhibitors as PET-imaging agents in the CNS676
4.2. 11C-Labeled MAO inhibitors677
4.3. 18F-Labeled MAO inhibitors677
5. Fluorinated cyclopropylamines as inhibitors of SSAO and MAO679
5.1. Cyclopropylamines as inhibitors of SSAO and MAO679
5.1.1. Overview of the development of cyclopropylamines as MAO inhibitors679
5.1.2. Isozyme selectivity of cyclopropylamine MAO inhibitors680
5.1.3. Mechanisms of inhibition681
5.2. Effects of fluorine substitution on inhibition of SSAO by cyclopropyl amines683
5.3. Effects of fluorine substitution on MAO inhibition684
6. Final comments687
Acknowledgments688
References688
Chapter 16: Fluoroolefin Dipeptide Isosteres: Structure, Syntheses, and Applications699
1. Introduction701
1.1. Peptide isosteres701
2. Fluoroolefin dipeptide isosteres702
2.1. Alkenes as amide bond substitutes702
2.2. Fluoroolefins as one of the best amide bond replacements703
2.3. Synthesis of fluoroolefin peptide isosteres704
3. Related methods for the synthesis of alpha-fluoro-alpha,beta-unsaturated ketones717
3.1. Conversion from trifluoromethyl ketones via Mg(0)-promoted successive double defluorination717
3.2. Synthesis of alpha-fluoro-alpha,beta-unsaturated ketones via palladium-catalyzed cross-coupling719
3.3. Synthesis of alpha-fluoro-alpha,beta-unsaturated ketone via allylic hydroxylation of vinyl fluo719
3.4. Synthesis of alpha-fluoroenone from 1,1,1,2-tetrafluoroethane719
3.5. Miscellaneous reactions720
4. Metathesis reactions721
5. Biological applications and utility of fluoroolefin peptide isosteres722
5.1. Background722
5.1.1. Role of cis–trans geometry in biological systems722
5.1.2. Fluorine in biological mimics722
5.2. Peptidyl prolyl isomerases (PPIases)723
5.2.1. Cyclophilin (CyP) inhibitors724
5.2.2. Pin1725
5.3. Dipeptidyl peptidase IV725
5.3.1. DPP IV inhibition727
5.3.2. Quiescent proline peptidase (QPP)728
5.4. Thermolysin728
5.5. beta-turn mimics728
References730
Chapter 17: Molecular Interactions of Fluorinated Amino Acids in a Native Polypeptide Environment737
1. Introduction738
2. Unique and versatile: The properties of fuoroalkyl groups739
2.1. Spatial demand and steric effects739
2.2. The electrostatic properties of the C-F bond740
3. Effects of fluorine in protein environments: Metabolism and structural integrity742
3.1. Proteolytic stability of Ca-fluoroalkyl amino acids742
3.1.1. a-Chymotrypsin: A natural protein environment742
3.1.2. Fluorine’s ambiguity: Can polar properties of fluororalkyl groups compete with conformation743
3.1.3. Summary746
3.2. The "orthogonal" properties of fluoroalkyl amino acid side chains747
3.2.1. The a-helical coiled coil: A versatile, amphiphilic model system747
3.2.2. Fluorinated alkyl side chains in a hydrophobic environment751
3.2.3. Fluorinated alkyl side chains in a hydrophilic environment752
3.2.4. Summary754
4. Conclusions and future perspectives755
References756
Chapter 18: Biological Fluorination in Streptomyces cattleya: The Fluorinase761
1. Introduction761
2. Characterisation of the fluorinase764
3. Mechanism of the fluorinase765
4. Reversibility of the fluorinase768
5. The fluorinase is a chlorinase768
6. Substrate specificity770
7. Genetic basis of fluorination in S. cattleya771
8. The biosynthetic pathway to fluoroacetate and 4-fluorothreonine.772
9. The fluorinase as a tool for synthesis and formation of C-18F bonds for positron emission tomogra774
References776
Subject Index778
Colour Plate Section793

Book details

Vendor Elsevier S & T
SKU 9780444530868
ISBN-13 9780080558110
Author Tressaud, Alain; Haufe, Günter
Category Science
Subject Industrial & Technical

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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.

- New approach of topics involving chemistry, biology and medicinal techniques
- Transdisciplinar papers on fluoride products
- Importance of fluoride products in health
- Updated data on specific topics

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