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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
Auteur
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.
Résumé
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
Contenu
Contributors xi
Editorial Preface xvii
Abbreviations xix
PART I FLUORINE-18 LABELED RADIOPHARMACEUTICALS 1
Synthesis of ()-[18F]Flubatine ([18F]FLBT) 3
Megan N. Stewart, Brian G. Hockley, and Peter J. H. Scott
Synthesis of [18F]-()Fluoroethoxy Benzovesamicol ([18F]FEOBV) 13
Brian G. Hockley, Megan N. Stewart, and Peter J. H. Scott
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
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
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
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
Synthesis of N-[11C]Methyl-4-Piperidinyl Propionate ([11C]PMP) 65
Xia Shao and Peter J. H. Scott
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
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
Synthesis of (R)-[N-Methyl-11C]PK11195 93
Vítor H. Alves, Antero J. Abrunhosa, and Miguel Castelo-Branco
PART III OTHER RADIOPHARMACEUTICALS 103
PART IV NEW METHODS FOR THE SYNTHESIS AND QUALITY CONTROL OF RADIOPHARMACEUTICALS 115
Direct, Nucleophilic Radiosynthesis of [18F]Trifluoroethyl Tosylate 117
Patrick J. Riss, Waqas Rafique, and Franklin I. Aigbirhio
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
[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
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
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
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
Production and Reaction of [11C]Carbon Disulfide for the Synthesis of [11C]Dithiocarbamates 177
Philip W. Miller
One-Pot, Direct Incorporation of [11CO2] into Carbamates 185
Christian K. Moseley and Jacob M. Hooker
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
Ethanol as a Solvent for Carbon-11 Radiochemistry 207
Xia Shao, Maria V. Fawaz, Keunsam Jang, and Peter J. H. Scott