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Introduction to Radiopharmaceutical Chemistry (Lecture 1)

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Introduction to Radiopharmaceutical Chemistry (Lecture 1) Introduction to Radiopharmaceutical chemistry (Lecture 1) Outline 1. Introduction Radiopharmaceuticals, Basics on radiochemistry, Molecular imaging, Nuclear medicine, PET and SPECT, Radiopharmacology 2. Radionuclide production, Nuclear reactor, Cyclotron, Radionuclide generators in medicine Radionuclide generators 3. Radiometal pharmaceuticals I Radiopharmaceutical chemistry: 99m Tc-Radiopharmaceuticals, Kits 4. Radiometal pharmaceuticals II Radiopharmaceutical chemistry: Re, Cu, In, Ga, Y 5. Organic radiopharmaceuticals I Introduction to PET, 11 C-radiopharmaceuticals 6. Organic radiopharmaceuticals II 11 C-radiopharmaceuticals (continuation) 7. Organic radiopharmaceuticals III Radiofluorinations: 18 F-radiopharmaceuticals 8. Organic radiopharmaceuticals IV Radiohalogenations: Br, I, At 9. Radiopharmacology Diagnostics & Therapeutics 1 Molecular Imaging Molecular imaging of specific biological and physiological processes at the molecular level in the intact organism Optical imaging Radionuclide-based imaging “Making the body biochemically transparent“ Molecular Imaging Gene expression Protein expression Protein function Physiological function 2 Application of radionuclides in life sciences Universal, efficient, simple • High sensitivity • Studies of metabolism • Mass balance, in vivo disribution (autoradiography) • 14 C, 3H, 32 P, 35 S Radiotracer-concept • George de Hevesey 1943 Nobel Prize (Chemistry (Application of radionuclide-based indicators, Father of nuclear medicine) In vivo pharmacology/biochemistry • Positron-emission-tomography (PET) • Single photon emission computered tomography (SPECT) in vivo radiotracer techniques Molecular probes and the radiotracer principle Biochemical information 3 Radionuclides in medicine – Nuclear medicine Nuclear medicine: Diagosis Use of gamma- and positron emitters Sensitivity = right positive/(right positive + false negative) Specificity = right negative/right negative + false positive) Antibody Nuklear medicine: Therapy Tumor Antigen Use of particle emitters (ααα, βββ-) Iodine- 131 cell Yttrium-90 Indium-111 Rhenium-186, 188 Emission tomography - SPECT Gantry-design of a SPECT-camera 4 Emission tomography - PET OH O 511 keV BGO or LSO HO HO OH Scintillator crystals 18F βββ+++ βββ−−− 180° 511 keV Photomultiplier Emission tomography - PET 5 Emission tomography - PET Pathobiochemistry in vivo Glycolysis Active transport Neurotransmission Multidrug resistance Hypoxia Apoptosis Angiogenesis Monitoring of gene therapy Inflammation, Infection Tumor-associated antigenes and receptors etc. “smart “ radiotracers! 6 Selection criteria and use of molecular probes for nuclear medicine molecular imaging • Can an appropriate compound be labeled with a suitable radionuclide? • Target specificity • High membrane permeability • Rapid blood clearance • No or only slow peripheral metabolism • High specific activity (Radiotracer principle) • Low non-specific binding (Target-to-Non-target ratio >>1) • Only a limited number of transport and biochemical reaction steps to facilitate tracerkinetic modelling 1. Molecular probes based upon enzyme-mediated transformations 2. Molecular probes based upon stochiometrical binding interactions 3. Molecular probes for perfusion studies Opportunities and trends of radiopharmaceutical chemistry • Making tumors visible as early as possible • Better understanding of tumor biochemistry • Therapy monitoring 7 Complex evaluation of tumor biology 10 13 10 12 Clinical detection 10 10 Sensitve detection Number tumor of cells Cure 10 0 Complex evaluation Tod 10 13 Gene expression? 10 12 Clinical detection Tumor-associated binding sites? 10 10 Metabolic activity? Apoptosis? Sensitve detection Angiogenesis? Hypoxia? Number tumor of cells Cure 10 0 8 Opportunities and trends of radiopharmaceutical chemistry Molecular of neurobiological basis of cerebral function See, how the brain is working Opportunities and trends of radiopharmaceutical chemistry Pharmacokinetics (Administration, distribution, elimination) Radiolabeled drug PET in drug development and evaluation Pharmacodynamics (Drug effect on metabolism, blood flow, receptor occupancy etc. ) Radiotracers (probes) + drug 9 RADIOPHARMACEUTICAL CHEMISTRY Nuclear pharmaceuticals Radiopharmaceuticals Radioactive drug - Diagnostics (Radiotracers) - Therapeutics Lead structure (high-throughput-screening, pathobiochemistry Target molecule Modification: • Introduction of radionuclide • Biodistribution, pharmacokinetics (“contrast“, quantifiable, minimal radiation burden, max. effect in radiation therapy Labeling methods Radiotracer-lead structure Radionuclide production 10 Important terms Radiation and radiation energy βββ−−−, γγγ, βββ+, ααα Radioaktivity Equation; 1 Ci = 3,7 . 10 10 Bq specific activity carrier-free, non-carrier-added, carrier-added Half-life (physical, biological, effective) Energy dose Nuclear reactions Nuclear reactor, Cyclotron Cross-section Activation equation (n, γγγ), (p,n), (p, ααα) and (d,n)-reactions Radiopharmaceutical chemistry Radiolabeling, radiotracer, lead structure radiochemical purity Good Manufacturing Practice (GMP) Radiopharmacology, Nuclear medicine Dose, Target/Nontarget, Sensitivity and specificity SPET, PET, in vitro, in vivo, Perfusion, clearance, Pharmacokinetics, Pharmacodynamics RADIOCHEMISTRY Nuclear reactions Radionuclide production Radioaktive radiation Labeling methods Production of radiopharmaceuticals 11 RADIOCHEMISTY Radionuclide production Processing • Nuclear reactionr • “hot“ labs • Cyclotron Radionuclide production – Table of nuclide 12 Radionuclide production - Radioactivity Bq Czernobyl accident 15 18 10 - 10 I-131, Xe-133, Cs-137, Kr-85, Sr-90 u.a. Spallation 10 14 I-131, I-133/Xe-133, Mo-99/Tc-99m, Xe-135 u.a. 10 9 Thyroid ectomy 10 3 K-40in adults 10 1 Cs-137/l milk in Berlin after Czernobyl Radionuclide production Impurities with dramatic effects Radiation burden e.g. 125 I in 123 I, euthyreotic thyroid 533 mGy/MBq 125 I 5.6 mGy/MBq 123 I 1% of 125 I doubles radiation burden!!! 13 Radionuclide production Shorter physical half-lifes Nuclear power plants in the clinics Iod-131 era Technetium-99m era Iod-123 (13 h) PET era 11 C 20.4 min 14 N(p, ααα)11 C 13 N 10.0 min 16 O(p, ααα)13 N 15 O 2.0 min 14 N(d,n) 15 O 18 F 109.6 min 20 Ne(d, ααα)18 F 18 O(p,n) 18 F Radionuclides Diagnosis Therapy Iodine-123 Iodine-131 Technetium-99m Radiometals 3+ PET-Radionuclides … (hard M )… C-11 F-18 I-123 Tc-99m authentic F forH, OH I forH, OH, CH 3 dramatic alterations compound Increasing availability of radionuclides 14 TcO - Iodide 4 Active transport 10 -8 - 10 -9 M Iodide 10 -1 M Chloride - hNIS (mamma CA): TcO 4 Uptake D. H. Moon et al., Nucl. Med. Biol. 28 (2001) 829-834 15 PET: Radiopharmaceuticals – [18 F]FDG besonders in Hirn und OH Herz - P nase G -6 O e xoki 18 F-D gut ität He eabil Perm tase HO spha 8 DG Pho 1 F- E G HO OH 18 F-D a Plasm Zelle in allen 18 Organen, aber H H H weniger in Hirn F HO CH2OH HO CH2OH HO CH2OH O O O und Herz H H H H H H HO HO HO OH H H H F H H H H OH OH OH D-Glucose 2-Desoxy-D-glucose 2-Fluor-2-desoxy-D-glucose Principle: Increased glycolysis in tumor cells (O. WARBURG) Glucose transporter (GLUT 1) and/or hexokinase Intracellular phosphorylation through hexokinase Intracellular trapping PET: Radiopharmaceuticals – [18 F]FDG 18 F-FDG PET - Control Nuklearmedizin TU Dresden / PET-Zentrum Rossendorf 16 PET: Radiopharmaceuticals – [18 F]FDG Primary tumour in the neck with lung metastesis R L R L R L Nuklearmedizin TU Dresden / PET-Zentrum Rossendorf PET: Radiopharmaceuticals – [18 F]FDG Therapy control Morbus Hodgkin Lymphoma (before Chemotherapy) Nuklearmedizin TU Dresden / PET-Zentrum Rossendorf 17 PET: Radiopharmaceuticals – [18 F]FDG Therapy control Morbus Hodgkin Lymphoma (after Chemotherapy) Nuklearmedizin TU Dresden / PET-Zentrum Rossendorf Radiopharmaceuticals: 3-O-Methyl-[18 F]FDOPA H2N CO2H Blood-brain-barrier MeO Tumour Amino acid transporter HO 18F Tumour Reference region Tumour / Brain 25000 4 3,5 20000 3 15000 2,5 2.2 2 10000 1,5 activity (Bq/ccm) 1 5000 tumour / non tumour 0,5 0 0 0 1000 2000 3000 4000 5000 Frame Midpoint Time [sec] MRT: Surgery defect Target/Non-Target OMFD-PET 18 PET: Radiopharmaceuticals - [18 F]FDOPA HO2C HO HO2C Decarboxylation HO NH2 NH2 NH2 HO HO HO Tyrosine Dopa Dopamine H2N CO2H HO HO 18F Control Decarboxylation disturbance Dopa to dopamine PET: Radiopharmaceuticals - [18 F]Fluoride O O 2+ 2+ P 3- Ca PO 4 Ca O O 2+ OH - Ca - O O 2+ 2+ Ca 3- F P PO 4 Ca O O 2+ Knochen- OH - Ca O O 2+ P Ca metastase O O Nuklearmedizin TU Dresden / PET-Zentrum Rossendorf 19 PET: Radiopharmaceuticals - [11 C]Acetats Precise mechanism unclear Increased lipid metabolism O * ONa Lymph node- metastasis Rezidive Nuklearmedizin TU Dresden / PET-Zentrum Rossendorf 20 Strahlenschutz – Gesamte Strahlenexposition Radiation protection 5-A-Regel • Begrenzung der eingesetzten Aktivität • Aufenthaltszeit begrenzen - Verringerung der Bestrahlungszeit • Abstand halten • Abschirmungen verwenden • Aufnahme von radioaktiven Stoffen vermeiden (bei Umgang mit offenen Radionukliden) Kombination von Strahlenschutzmaßnahmen 1. Verringerung der Bestrahlungszeit Aufenthaltszeit begrenzen 2. Abstand halten 3. Abschirmungen verwenden 21.
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