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First Synthesis of an Electrophilic 18F-Labelling Reagent Without Carrier Fluorine

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First Synthesis of an Electrophilic 18F-Labelling Reagent Without Carrier Fluorine Cover picture: "3+1" Oxorhenium(V) complex located in the binding site of the serotonin-5-HT„receptor model postulated by Hoeltje et al. (see p. 1) FZR - 200 December 1997 Annual Report 1997 Institute of Bioinorganic and Radiopharmaceutical Chemistry Editor: B. Johannsen Editorial staff: S. Seifert CONTENTS FOREWORD OPENING OF THE ROSSENDORF PET CENTER I. EDITORIAL II. RESEARCH REPORTS 1. Serotonin Receptor-BindingTechnetium and Rhenium Complexes 16. Molecular modelling studies on interactions of rhenium compounds with a serotoninergic 5HT, receptor model M. Höltje, B. Brandt , H.-D. Höltje 2. Serotonin Receptor-Binding Technetium and Rhenium Complexes 17. Different routes of n.c.a. preparation of "3+1"-Tc complexes S. Seifert, H.-J. Pietzsch, M. Scheunemann, H. Spies, B. Johannsen 3. Serotonin Receptor-Binding Technetium and Rhenium Complexes 14 18. Autoradiographical studies of serotonin receptor-binding Tc-99m complexes on post-mortem human brains H.-J. Pietzsch, H. Hall, S. Seifert, M. Scheunemann, P. Brust, H. Spies, C. Halldin, B. Johannsen 4. Serotonin Receptor-Binding Technetium and Rhenium Complexes 19. A general rnethod for the preparation of 8mercaptobutyl and wnercaptopentyl amines. Synthesis of olxorhenium (V) complexes containing the intact 4-(4-fluoro)- benzoyl piperidine pharmawphore. M. Scheunemann 5. Serotonin Receptor-Binding Technetium and Rhenium Cornplexes 18 20. A simple and eficient synthesis of a derivatized pseudotripeptide containing a methylene thioether isostere and its use for the design of bifunctional rhenium and technetiurn chelating agents M. Scheunemann, B. Johannsen 6. Rhenium and Technetium Carbonyl Complexes for the Labelling of Bioactive Molecules 20 4. N.c.a. preparation of a 99"rc carbonyl complex as a potential serotonin 5-HT, receptor-binding ligand M. Reisgys, H.-J. Pietzsch, H. Spies, R. Alberto 7. Preparation of Neutral n.c.a. TcNComplexes with Tetradentate Ligands S. Seifert, H.-J. Pietzsch, M. Scheunemann, H. Spies, B. Johannsen 8. The Specific Transport of Serotonin in RBE4 Cells Depends on the Presence of Extracellular Ions A. Friedrich. P. Brust 9. lnfluence of Various Dnigs on the Serotonin Transport in RBE4 Cells A. Friedrich, P. Brust 10. Evidence of the Existence of a Functionally Active Serotonin Transporter in an lmmortalized Brain Endothelial Cell Line (RBE4 Cells) A. Friedrich, P. Brust 11. Novel Rhenium Complexes from 3-Substituted Tropane Derivatives - Synthesis and Evaluation A. Hoepping, P. Brust, R. Berger, H. Spies 12. lmproved Synthesis and Biological Evaluation of 99Tc-Technepineand Comparison with a Modified Technepine Containing a Hexyl Linker (Hexyltechnepine) A. Hoepping, D. Breitkreuz, R. Berger, P. Brust, H. Jungclas, M. Kretzschmar, S. Seifert, H. Spies, R. Syhre 13. Technetium and Rhenium-Labelled Steroids, 3. Synthesis of 17a-substituted mercaptoalkynyl derivatives of 3,17ß-estradiol F. Wüst, H. Spies 14. Technetium and Rhenium-Labelled Steroids, 4. Synthesis of 3+Inmixed-ligand oxorhenium(V) complexes with 17a-mercapto- alkynyl derivatives of 3,17ß-estradiol F. Wüst, P. Leibnitz', H. Spies 15. Technetium and Rhenium-Labelled Steroids 5. Oxorhenium(V) mixed-ligand complexes with 17ß-hydroxy-7a-(5-mercaptopent-I-yl)- androsta-4-ene-3-one: first rhenium-containingandrogens F. Wüst, D. Scheller, S. Machill, H. Spies 16. Technetium and Rhenium-Labelled Steroids 6. Synthesis of a 17a-substituted isocyanide ligand of 3,17ß-estradiol and its conversion into a "umbrella-malecule" containing 2,2',2"'-nitrilotris(ethanethiol) coordinated rhenium(ll1) F. Wüst, H. Spies 17. Technetium and Rhenium Labelled Steroids 7. Synthesis of rhenium(1) and technetium(1) carbonyVdithioether ligand complexes bearing 3,17ß-estradiol and progesterone M. Reisgys, F. Wüst, H.-J. Pietzsch, H. Spies, B. Johannsen 18. Technetium and Rhenium-Labelled Steroids 8. Lipophiliciiy of rhenium complexes with 1-mercapto-4-methylestra-I,3,5(10)- en-7-one, 17a-substituted estradiol as well as 7a-substituted testosterone, determined by using RP-HPLC R. Berger, F. Wüst, H. Spies 19. Structural Modifications of Carrier Added *3+1" Oxotechnetiurn (V) Mixed-Ligand Complexes in Order to lmprove Their Blood Pool Activiity in Rats R. Syhre, R. Berger, P. Brust, M. Friebe, H.-& Pietzsch, S. Seifert, M. Scheunemann, H. Spies, B. Johannsen 20. Structural Modification of the Tridentate Ligand of n.c.a. "3+In Oxotechnetium(V) Mixed-Ligand Complexes and Their EfFects on the Distribution and Retention Behaviour in Rats R. Syhre, R. Berger, P. Brust, H.-J. Pietzsch, S. Seifert, M. Scheunemann, H. Spies, B. Johannsen 21. Rhenium and Technetium Mixed-Ligand Chelates Functionalized by Amine Groups 2. Rhenium and Technetium Complexes with Aikyl Thiols as Monodentate Ligands: Preparation, IogPlpKa Determination and Biodistributian Studies M. Friebe, HSpies, R. Berger, B. Johannsen, M. Papadopoulos, I. Pirmettis, T.Maina, B. Nock, E. Chiotellis 22. In-Vivo Binding of [3H]spiperoneto Serotonin and Dopamine Receptors, a Quantitative Whole-Body Autoradiographic Study of Mice M. Kretzschmar, P. Brust, R. Bergmann, J. Römer 23. Technetium Coordination Features of Cysteine-Containing Peptides: Two Ways to Obtain Direct Labelled Peptides. An EXAFS Study of an Endothelin and an LHRH Derivative. R. Jankowsky, S. Kirsch, B. Noll, H.Spies and B. Johannsen 24. Characterization of Rhenium(V) Complexes with Cysteine, Cysteamine and Acetylcysteine at Various pH Values in Aqueous Solution S. Kirsch, R. Jankowsky, H. Spies, B. Johannsen 25. Rhenium(V) 0x0 Complexes with Glycylcysteine and Glycylcysteinylglycine: 79 Complexation Behaviour in Aqueous Solution S. Kirsch, R. Jankowsky, H. Spies, B. Johannsen 26. Mercaptoacetyllysylglycine (MALYG), a New Ligand for Coupling Technetium 82 and Rhenium to Biomolecules St. Noll, B. Noll, H. Spies, I. Zolle, B. Johannsen 27. A New Type of Mixed Ligand Complexes of TechnetiumtV) and Rhenium(V) with 85 Mercaptoacetyl Glycine (MAG,) and Coligands Containing Reactive Groups B. Noll, St. Noll, R. Jankowsky, H. Spies, B. Johannsen 28. Cysteine Challenge of Tc Complexes with MAG Derivatives and Analogues B. Noll, B. Nock, St. Noll, H. Spies, B. Johannsen 29. Tc(V) and Rew) Complexes of N-(Mercaptoacetylg1ycyl)-histamine C. S. Hilger, F. Blume, B. Noll, P. Leibnitz, .H. Spies 30. Effective One Step Coupling of ReiTc-MAG, Complexes with Amines and Nucleobases T. Kniess, St. Noll, B. Noll, H. Spies 31. Technetium and Rhenium Cornplexes of Derivatized Nucleic Acid Components 99 4. Synthesis of Re and Tc Complexes Coupled with 2'-Deoxycytidine and 2'-Deoxyadenosine St. Noll, B. Noll, T. Kniess, H. Spies 32. Studies of in vivo Labelling of Nucleic Acids with TcComplexes. First Results: Uptake of Tc Complexes in Cultured Cells St. Noll, B. Noll, G. Kampf, H. Spies, B. Johannsen 33. Rhenium and Technetium Carbonyl Complexes for the Labelling of Bioactive Molecules 105 3. Tricarbonylrhenium(l) complexes with bidentate thioether ligands with functional groups M. Reisgys, H.-J. Pietzsch, H. Spies, R. Alberto, U. Abram 34. Unexpected Formation of a P,S,N- Coordinated cis-Dioxorhenium(V) Complex 107 of Trigonal-Bipyramidal Geometry M. Friebe, H. Spies, W. Seichter, B. Johannsen 35. Stability and Structure of a 3+1" Mixed Ligand 'SNS-G Co-ordinated 99Tc-Complex 110 at the c.a. Level in Rat Blood by X-ray Aksorption Spectroscopy M. Friebe, R. Jankowsky, H. Spies, B. Johannsen 36. Reactions of Hydroxy-Group Containing '379' Mixed-Ligand Rheniumw) Compounds. 113 Part I : Silylation of '371' Mixed-Ligand Complexes. Th. Fietz, H. Spies, A. Zablotskaya, D. Scheller 37. Reactions of Hydroxy-Group Containing '371' Mixed-Ligand Oxorhenium(V) Complexes. 116 Part 2: Acylation of (2-Hydroxyethanethiolato)(3-thiapentane-I-5-dithio1ato)-oxorhenium(V) Th. Fietz, H. Spies 38. Reactions of Hydroxy-Group Containing '34' Mixed-Ligand Rheniumw) Complexes. Part 3: Unexpected Reaction of '371' Mixed-Ligand Complexes With Thionyl and Acyl Halides and Methyl Iodide. Structural Considerations for a new Modification of Chlorooxo(3-thiapentane-I.5-dithiolato)rhenium(V). Th. Fietz, P.Leibnitz 39. Synthesis of a novel N2S2 Ligand Containing Carboxylate as a Bifunctional Chelating Agent T. Kniess, H. Spies 40. Lipophilicity Studies of Some Tricarbonylrhenium(l) Complexes and their Ligands by Reversed Phase HPLC R. Berger, A. Schaffland, H. Spies 41. Are there Differences in Lipophilicity between the Transition Metals Technetium and Rhenium? R. Berger, M. Friebe, H. Spies, B. Johannsen 42. HPLC Troubleshooting: Drifting Retention Times R. Berger, M. Friebe, H. Spies 43. The lnfluence of Selected "3+1"0xorheniuml(V) Complexes on the Activity of Monoamine Oxidase in Rat Brain Homogenate S. Matys, P. Brust, M. Scheunemann, H.-J. Pietzsch 44. Metabolic Changes in Rat Brain Endothelial Cells Caused by Inhibitors of the P-Glycoprotein R. Bergmann, P. Brust, B. Johannsen 45. Distribution of v1C](ir)McN5652 in the Mouse Brain - an ex-viv0 Autoradiographic Study M. Kretzschmar, J. Zessin, J. Steinbach, P. Brust 46. The Dopaminergic System is Altered under Neonatal Asphyxia - Studies with [F-I 81FDOPA P. Brust, R. Bergmann, R. Bauer, B. Walter, G. Vorwieger, F. Füchtner, E. Will, H. Linemann, J. Steinbach 47. HPLC Analysis of the Metabolism of 6-t8fl~luoro-~-~0~~(FDOPA) A. Chrornatography and Validation G. Vorwieger, F. Füchtner, B. Walter, R. Bergmann, R. Bauer, J. Steinbach, P. Brust 48. HPLC-Analysis of the Metabolism of 6-[18Fl~luor~-~~~~(FDOPA) B. FDOPA Metabolism in Newborn Piglets G. Vorwieger, R. Bergmann, B. Walter, F. Füchtner, J. Steinbach,
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