Further Radiopharmaceuticals for Positron Emission Tomography and New Strategies for Their Production, Volume 2

ISBN-13: 9781118237847 / Angielski / Twarda / 2015 / 288 str.

Peter J. H. Scott

Opis

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

This book provides reliable methods, including information to duplicate procedures, for synthesizing radionuclides used in positron emission tomography (PET) imaging and saves chemists time by eliminating the time–consuming process of searching journal articles and extracting details from lengthy experimental sections.

Spis treści

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– –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

O autorze

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.

Blurb

The ultimate reference guide to the synthesis of radiopharmaceutical

The Radiochemical Syntheses series provides scientists and professionals with a comprehensive reference to proven synthetic methods for radiochemical reactions, along with step–by–step guidance on how to replicate these syntheses in the laboratory.

Volume 2 in the series focuses on the synthesis and purification of radiopharmaceuticals in clinical use today as well as important new methods in radiochemistry. Contributions from leading researchers detail methods and procedures for conducting radiochemical reactions to prepare important radiopharmaceuticals that are used in positron emission tomography (PET) imaging. Also highlighted in this book are new approaches to carbon–11 (C11) and fluorine–18 (F18), which are two of the most commonly used radionuclides in PET imaging. New methods include solid–phase radiochemistry, transition–metal catalyzed radiochemistry, microfluidics, click chemistry, green radiochemistry and new strategies for radiopharmaceutical quality control. These detailed monographs provide readers the necessary information needed to reproduce these synthetic reactions and new procedures in their own labs.

Readers have key experimental details culled from the literature at their fingertips, greatly simplifying the process of qualifying a site for the clinical production of new radiopharmaceuticals.