Description

Book Synopsis
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 control

Table of Contents

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-β-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

Further Radiopharmaceuticals for Positron

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    A Hardback by Peter J. H. Scott, Michael R. Kilbourn

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      Publisher: John Wiley & Sons Inc
      Publication Date: 08/06/2015
      ISBN13: 9781118237847, 978-1118237847
      ISBN10: 1118237846
      Also in:
      Pharmacology Chemistry

      Description

      Book Synopsis
      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 control

      Table of Contents

      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-β-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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