This book describes methods and procedures for preparing PET radiopharmaceuticals, and highlights new methods for conducting radiochemical reactions with carbon-11 (C11) and fluorine-18 (F18), which are two of the most commonly used radionuclides in positron emission tomography (PET) imaging. - Provides reliable methods for radiochemical syntheses and reactions, including all essential information to duplicate the procedure - Eliminates the time-consuming process of searching journal articles and extracting pertinent details from lengthy experimental sections or supporting information -…mehr
This book describes methods and procedures for preparing PET radiopharmaceuticals, and highlights new methods for conducting radiochemical reactions with carbon-11 (C11) and fluorine-18 (F18), which are two of the most commonly used radionuclides in positron emission tomography (PET) imaging.
- Provides reliable methods for radiochemical syntheses and reactions, including all essential information to duplicate the procedure - Eliminates the time-consuming process of searching journal articles and extracting pertinent details from lengthy experimental sections or supporting information - Focuses on an emerging and important area for pharmaceutical and medical applications - Encompasses technical, regulatory, and application aspects - Includes solid-phase radiochemistry, transition-metal catalyzed radiochemistry, microfluidics, click chemistry, green radiochemistry and new strategies for radiopharmaceutical quality controlHinweis: Dieser Artikel kann nur an eine deutsche Lieferadresse ausgeliefert werden.
Peter J. H. Scott is an Assistant Professor in the Department of Radiology at the University of Michigan Medical School (USA), Director of the University of Michigan PET Center (USA) and a member of the Interdepartmental Program in Medicinal Chemistry. Professor Scott edited Linker Strategies in Solid-Phase Organic Synthesis (also from Wiley) and is the series editor for both the Wiley Series on Radiochemical Syntheses and the Wiley Series on Solid Phase Organic Syntheses.
Inhaltsangabe
Contributors xi Editorial Preface xvii Abbreviations xix PART I FLUORINE-18 LABELED RADIOPHARMACEUTICALS 1 1. Synthesis of ( )-[18F]Flubatine ([18F]FLBT) 3 Megan N. Stewart, Brian G. Hockley, and Peter J. H. Scott 2. Synthesis of [18F]-( )Fluoroethoxy Benzovesamicol ([18F]FEOBV) 13 Brian G. Hockley, Megan N. Stewart, and Peter J. H. Scott 3. Synthesis of [18F]Fluoromethylcholine ([18F]FCH) via [18F]Fluoromethyl Tosylate 21 Melissa E. Rodnick, Allen F. Brooks, Brian G. Hockley, Bradford D. Henderson, and Peter J. H. Scott 4. Radiosynthesis of [18F]Flotegatide ([18F]RGD-K5) 29 Hartmuth C. Kolb, Fanrong Mu, Umesh Gangadharmath, Vani P. Mocharla, Zhihong Zhu, Ashok Chaudhary, and Joseph C. Walsh 5. Synthesis of 3-[18F]Fluoro-5-(2-Pyridinylethynyl) Benzonitrile ([18F]FPEB) 41 Steven H. Liang, Daniel L. Yokell, Raul N. Jackson, Peter A. Rice, Eli Livni, David Alagille, Gilles Tamagnan, Thomas Lee Collier, and Neil Vasdev 6. Radiosynthesis of 2 -Deoxy-2 -[18F]Fluoro-5-Methyl-1-ß-d-Arabinofuranosyluracil ([18F]FMAU) 53 Kai Chen and Peter S. Conti PART II CARBON-11 LABELED RADIOPHARMACEUTICALS 63 7. Synthesis of N-[11C]Methyl-4-Piperidinyl Propionate ([11C]PMP) 65 Xia Shao and Peter J. H. Scott 8. Synthesis of 1-(2,4-Dichlorophenyl)-4-Cyano-5-(4-[11C]methoxyphenyl)-N-(Piperidin-1-yl)-1H-Pyrazole-3-Carboxamide ([11C]OMAR) 73 Xia Shao, Keunsam Jang, and Peter J. H. Scott 9. Synthesis of Carbon-11 Labeled (+)-4-Propyl-3,4,4a,5,6,10b-Hexahydro-2H-Naphtho[1,2-b][1,4]Oxazin-9-Ol ([11C]-(+)-PHNO) 81 Christophe Plisson, Joaquim Ramada-Magalhaes, and Jan Passchier 10. Synthesis of (R)-[N-Methyl-11C]PK11195 93 Vítor H. Alves, Antero J. Abrunhosa, and Miguel Castelo-Branco PART III OTHER RADIOPHARMACEUTICALS 103 11. Synthesis of Oxygen-15 Water ([15O]H2O) 105 David W. Dick and G. Leonard Watkins PART IV NEW METHODS FOR THE SYNTHESIS AND QUALITY CONTROL OF RADIOPHARMACEUTICALS 115 12. Direct, Nucleophilic Radiosynthesis of [18F]Trifluoroethyl Tosylate 117 Patrick J. Riss, Waqas Rafique, and Franklin I. Aigbirhio 13. Synthesis of [18F]N-Methyl Lansoprazole via Generation of a [18F]Trifluoromethyl Group 123 Allen F. Brooks, Melissa E. Rodnick, Garret M. Carpenter, and Peter J. H. Scott 14. [18F]Fluorination of (Mesityl)(Aryl)Iodonium Salts 129 Naoko Ichiishi, Allen F. Brooks, Joseph J. Topczewski, Melissa E. Rodnick, Melanie S. Sanford, and Peter J. H. Scott 15. Pd(IV)-Mediated Fluorination of Arenes with [18F]F- for PET Imaging 139 Nathan J. Schauer, Stephen M. Carlin, Hong Ren, and Jacob M. Hooker 16. Silicon Fluoride Acceptors (SIFAs) for Peptide and Protein Labeling with 18F 149 Ralf Schirrmacher, Alexey Kostikov, Carmen Wängler, Klaus Jurkschat, Vadim Bernard-Gauthier, Esther Schirrmacher, and Björn Wängler 17. Solid Phase Synthesis of [18F]-2-Fluoro-2-Deoxy-d-Glucose: A Resin-Linker-Vector (RLV) Approach 163 Lynda J. Brown, Imtiaz Khan, Harry J. Wadsworth, Alexander Jackson, Nianchun Ma, Nicolas Millot, Sue M. Champion, Denis R. Bouvet, Alex M. Gibson, and Richard C. D. Brown 18. Production and Reaction of [11C]Carbon Disulfide for the Synthesis of [11C]Dithiocarbamates 177 Philip W. Miller 19. One-Pot, Direct Incorporation of [11CO2] into Carbamates 185 Christian K. Moseley and Jacob M. Hooker 20. Radiosynthesis of [11C]Carboxamides via Reaction of [11C]CO2 Captured by a Cu(I)-Based Catalyst System with Boronic Acid Ester Precursors 197 Patrick J. Riss, Shuiyu Lu, Sanjay Telu, Franklin I. Aigbirhio, and Victor W. Pike 21. Ethanol as a Solvent for Carbon-11 Radiochemistry 207 Xia Shao, Maria V. Fawaz, Keunsam Jang, and Peter J. H. Scott 22. Synthesis and Applications of [11C]Hydrogen Cyanide 233 Xia Shao, Melissa E. Rodnick, Allen F. Brooks, and Peter J. H. Scott 23. Determination of Radiochemical Purity and Radiochemical Identity of [13N]NH3 Using Thin Layer Chromatography 241 Peter A. Rice and Daniel L. Yokell Appendix 1: Supplier Information 247 Index 253
Contributors xi Editorial Preface xvii Abbreviations xix PART I FLUORINE-18 LABELED RADIOPHARMACEUTICALS 1 1. Synthesis of ( )-[18F]Flubatine ([18F]FLBT) 3 Megan N. Stewart, Brian G. Hockley, and Peter J. H. Scott 2. Synthesis of [18F]-( )Fluoroethoxy Benzovesamicol ([18F]FEOBV) 13 Brian G. Hockley, Megan N. Stewart, and Peter J. H. Scott 3. Synthesis of [18F]Fluoromethylcholine ([18F]FCH) via [18F]Fluoromethyl Tosylate 21 Melissa E. Rodnick, Allen F. Brooks, Brian G. Hockley, Bradford D. Henderson, and Peter J. H. Scott 4. Radiosynthesis of [18F]Flotegatide ([18F]RGD-K5) 29 Hartmuth C. Kolb, Fanrong Mu, Umesh Gangadharmath, Vani P. Mocharla, Zhihong Zhu, Ashok Chaudhary, and Joseph C. Walsh 5. Synthesis of 3-[18F]Fluoro-5-(2-Pyridinylethynyl) Benzonitrile ([18F]FPEB) 41 Steven H. Liang, Daniel L. Yokell, Raul N. Jackson, Peter A. Rice, Eli Livni, David Alagille, Gilles Tamagnan, Thomas Lee Collier, and Neil Vasdev 6. Radiosynthesis of 2 -Deoxy-2 -[18F]Fluoro-5-Methyl-1-ß-d-Arabinofuranosyluracil ([18F]FMAU) 53 Kai Chen and Peter S. Conti PART II CARBON-11 LABELED RADIOPHARMACEUTICALS 63 7. Synthesis of N-[11C]Methyl-4-Piperidinyl Propionate ([11C]PMP) 65 Xia Shao and Peter J. H. Scott 8. Synthesis of 1-(2,4-Dichlorophenyl)-4-Cyano-5-(4-[11C]methoxyphenyl)-N-(Piperidin-1-yl)-1H-Pyrazole-3-Carboxamide ([11C]OMAR) 73 Xia Shao, Keunsam Jang, and Peter J. H. Scott 9. Synthesis of Carbon-11 Labeled (+)-4-Propyl-3,4,4a,5,6,10b-Hexahydro-2H-Naphtho[1,2-b][1,4]Oxazin-9-Ol ([11C]-(+)-PHNO) 81 Christophe Plisson, Joaquim Ramada-Magalhaes, and Jan Passchier 10. Synthesis of (R)-[N-Methyl-11C]PK11195 93 Vítor H. Alves, Antero J. Abrunhosa, and Miguel Castelo-Branco PART III OTHER RADIOPHARMACEUTICALS 103 11. Synthesis of Oxygen-15 Water ([15O]H2O) 105 David W. Dick and G. Leonard Watkins PART IV NEW METHODS FOR THE SYNTHESIS AND QUALITY CONTROL OF RADIOPHARMACEUTICALS 115 12. Direct, Nucleophilic Radiosynthesis of [18F]Trifluoroethyl Tosylate 117 Patrick J. Riss, Waqas Rafique, and Franklin I. Aigbirhio 13. Synthesis of [18F]N-Methyl Lansoprazole via Generation of a [18F]Trifluoromethyl Group 123 Allen F. Brooks, Melissa E. Rodnick, Garret M. Carpenter, and Peter J. H. Scott 14. [18F]Fluorination of (Mesityl)(Aryl)Iodonium Salts 129 Naoko Ichiishi, Allen F. Brooks, Joseph J. Topczewski, Melissa E. Rodnick, Melanie S. Sanford, and Peter J. H. Scott 15. Pd(IV)-Mediated Fluorination of Arenes with [18F]F- for PET Imaging 139 Nathan J. Schauer, Stephen M. Carlin, Hong Ren, and Jacob M. Hooker 16. Silicon Fluoride Acceptors (SIFAs) for Peptide and Protein Labeling with 18F 149 Ralf Schirrmacher, Alexey Kostikov, Carmen Wängler, Klaus Jurkschat, Vadim Bernard-Gauthier, Esther Schirrmacher, and Björn Wängler 17. Solid Phase Synthesis of [18F]-2-Fluoro-2-Deoxy-d-Glucose: A Resin-Linker-Vector (RLV) Approach 163 Lynda J. Brown, Imtiaz Khan, Harry J. Wadsworth, Alexander Jackson, Nianchun Ma, Nicolas Millot, Sue M. Champion, Denis R. Bouvet, Alex M. Gibson, and Richard C. D. Brown 18. Production and Reaction of [11C]Carbon Disulfide for the Synthesis of [11C]Dithiocarbamates 177 Philip W. Miller 19. One-Pot, Direct Incorporation of [11CO2] into Carbamates 185 Christian K. Moseley and Jacob M. Hooker 20. Radiosynthesis of [11C]Carboxamides via Reaction of [11C]CO2 Captured by a Cu(I)-Based Catalyst System with Boronic Acid Ester Precursors 197 Patrick J. Riss, Shuiyu Lu, Sanjay Telu, Franklin I. Aigbirhio, and Victor W. Pike 21. Ethanol as a Solvent for Carbon-11 Radiochemistry 207 Xia Shao, Maria V. Fawaz, Keunsam Jang, and Peter J. H. Scott 22. Synthesis and Applications of [11C]Hydrogen Cyanide 233 Xia Shao, Melissa E. Rodnick, Allen F. Brooks, and Peter J. H. Scott 23. Determination of Radiochemical Purity and Radiochemical Identity of [13N]NH3 Using Thin Layer Chromatography 241 Peter A. Rice and Daniel L. Yokell Appendix 1: Supplier Information 247 Index 253
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