Chemistry of Molecular Imaging

Nicholas Long, PhD, is the Sir Edward Frankland BP Professor of Inorganic Chemistry and Head of the Catalysis, Sustainability and Applied Inorganics section in the Department of Chemistry, Imperial College London. He has published more than 150 scientific papers, including several high impact review articles and a critically-acclaimed textbook titled ‘Metallocenes’. He is Co-Director of the Centre for Doctoral Training in Medical Imaging at Imperial College and King’s College London. Wing-Tak Wong, PhD, ScD, is Chair Professor of Chemical Technology and Head of the Department of Applied Biology and Chemical Technology at the Hong Kong Polytechnic University. He has received three International and US patents for his recent research on lanthanide luminescent materials, and is an author of more than 450 research papers.

• Preface ixList of Contributors xi1 An Introduction to Molecular Imaging 1Ga-Lai Law and Wing-Tak Wong1.1 Introduction 11.2 What is Positron Emission Tomography (PET)? 31.3 What is Single Photon Emission Computed Tomography (SPECT)? 61.4 What is Computed Tomography (CT) or Computed Axial Tomography (CAT)? 81.5 What is Magnetic Resonance Imaging (MRI)? 111.6 What is Optical Imaging? 151.7 What is Ultrasound (US)? 191.8 Conclusions 22References 242 Chemical Methodology for Labelling and Bioconjugation 25Lina Cui and Jianghong Rao2.1 Introduction 252.2 Chemical Methods 252.3 Site-Specific Modification of Proteins or Peptides 362.4 Conclusions 45References 453 Recent Developments in the Chemistry of [18F]Fluoride for PET 55Dirk Roeda and Frédéric Dollé3.1 Introduction 553.2 Fluorine-18: The Starting Material 563.3 Reactive [18F]Fluoride 563.4 The Radiofluorination 583.5 Labelling of Large Biological Molecules 653.6 Conclusions 70References 704 Carbon-11 Nitrogen-13 and Oxygen-15 Chemistry: An Introduction to Chemistry with Short-Lived Radioisotopes 79Philip W. Miller Koichi Kato and Bengt Långström4.1 Introduction 794.2 Carbon-11 Chemistry 814.3 Nitrogen-13 Chemistry 934.4 Oxygen-15 Chemistry 984.5 Conclusions 99References 995 The Chemistry of Inorganic Nuclides (86Y 68Ga 64Cu 89Zr 124I) 105Eric W. Price and Chris Orvig5.1 Introduction: Inorganic Nuclide-Based Radiopharmaceuticals 1055.2 Radiopharmaceutical Design 1075.3 Radiopharmaceutical Stability 1085.4 86Yttrium Radiometal Ion Properties 1105.5 68Gallium Radiometal Ion Properties 1165.6 64Copper Radiometal Ion Properties 1205.7 89Zirconium Radiometal Ion Properties 1235.8 124Iodine Nuclide Properties 1255.9 Conclusions 129References 1296 The Radiopharmaceutical Chemistry of Technetium and Rhenium 137Jonathan R. Dilworth and Sofia I. Pascu6.1 Introduction 1376.2 Technetium and Rhenium Radiopharmaceutical Chemistry 1396.3 Technetium and Rhenium(IV) 1496.4 Technetium and Rhenium(III) 1496.5 Technetium and Rhenium(I) 1516.6 Imaging of Hypoxia with 99mTc 1556.7 Technetium and Rhenium Diphosphonate Complexes 1576.8 The Future for Technetium and Rhenium Radiopharmaceuticals 157References 1587 The Radiopharmaceutical Chemistry of Gallium(III) and Indium(III) for SPECT Imaging 165Jonathan R. Dilworth and Sofia I. Pascu7.1 Introduction to Gallium and Indium Chemistry 1657.2 Gallium and Indium Complexes and Related Bioconjugates 1667.3 Auger Electron Therapy with 111Indium 1757.4 Prospects for 67Ga and 111In Radiochemistry 176References 1768 The Chemistry of Lanthanide MRI Contrast Agents 179Stephen Faulkner and Octavia A. Blackburn8.1 Introduction 1798.2 Gadolinium Complexes as MRI Contrast Agents 1808.3 Minimising the Toxicity of Gadolinium Contrast Agents 1848.4 Rationalising the Behaviour of MRI Contrast Agents 1858.5 Strategies for Increasing Relaxivity 1888.6 Responsive MRI 1928.7 Conclusions and Prospects 195References 1959 Nanoparticulate MRI Contrast Agents 199Juan Gallo and Nicholas J. Long9.1 Introduction 1999.2 T2 Contrast Agents 2009.3 T1 Contrast Agents 2039.4 T1-T2 Dual MRI Contrast Agents 2089.5 Water Solubilisation 2099.6 Functionalisation and Surface Modification 2139.7 Applications 2169.8 Conclusions and Outlook 220References 22010 CEST and PARACEST Agents for Molecular Imaging 225Osasere M. Evbuomwan Enzo Terreno Silvio Aime and A. Dean Sherry10.1 Introduction 22510.2 Diamagnetic CEST Agents 22610.3 Paramagnetic Chemical Exchange Saturation Transfer (PARACEST) Agents 22910.4 Responsive PARACEST Agents 23010.5 In Vivo Detection of PARACEST Agents 23310.6 Supramolecular CEST Agents 23510.7 LipoCEST Agents 23610.8 Conclusions 241References 24111 Organic Molecules for Optical Imaging 245Michael Hon-Wah Lam Ga-Lai Law Chi-Sing Lee and Ka-Leung Wong11.1 Introduction 24511.2 Designing Molecular Probes for Bio-imaging 24611.3 Different Types of Organic-based Chromophores and Fluorophores for Bioimaging 24911.4 Mechanisms of Photophysical Processes and Their Applications in Molecular Imaging and Chemosensing 25811.5 Two/Multi-photon Induced Emission and In Vitro / In Vivo Imaging 26211.6 Time-Resolved Imaging 26611.7 Bioluminescence in Molecular Imaging 26711.8 Photoacoustic Imaging 26911.9 Conclusion and Future Perspectives 270References 27012 Application of d- and f-Block Fluorescent Cell Imaging Agents 275Michael P. Coogan and Simon J. A. PopeAbbreviations 27512.1 Introduction 27512.2 d6 Metal Complexes in Fluorescent Cell Imaging 27712.3 f-Block Imaging Agents 28512.4 Conclusions 296References 29613 Lanthanide-Based Upconversion Nanophosphors for Bioimaging 299Fuyou Li Wei Feng Jing Zhou and Yun Sun13.1 Introduction 29913.2 Fabrication of Ln-UCNPs Suitable for Bioimaging 29913.3 Surface Modification of Ln-UCNPs 30413.4 In Vivo Imaging Applications 30613.5 Biodistribution and Toxicity of UCNPs 31613.6 Future Directions 317References 31714 Microbubbles: Contrast Agents for Ultrasound and MRI 321April M. Chow and Ed X. Wu14.1 Introduction 32114.2 Classification of Microbubbles 32114.3 Applications in Ultrasound Imaging 32414.4 Applications in Magnetic Resonance Imaging 32714.5 Applications beyond US Imaging and MRI 33014.6 Conclusions: Limitations Bioeffects and Safety 330References 33115 Non-Nanoparticle-Based Dual-Modality Imaging Agents 335Reinier Hernandez Tapas R. Nayak Hao Hong and Weibo Cai15.1 Introduction 33515.2 PET/Optical Agents 33615.3 SPECT/Optical Agents 34115.4 MRI/Optical Agents 34515.5 PET/MRI Agents 34815.6 Conclusions 348References 35016 Chemical Strategies for the Development of Multimodal Imaging Probes Using Nanoparticles 355Amanda L. Eckermann Daniel J. Mastarone and Thomas J. Meade16.1 Introduction 35516.2 Fluorescence-MRI 35716.3 Near-Infrared Fluorescence/MRI 35916.4 NIR-PET 36816.5 Upconversion Luminescence 37216.6 PET-SPECT-CT-MRI 37616.7 Ultrasound 38216.8 Magnetomotive Optical Coherence Tomography (MM-OCT) 38316.9 Photoacoustic Imaging 38416.10 Conclusions 384References 385Index 389

“This book fills a void in the area of molecular imaging from the eyes of a chemist, and I am convinced that it will be of great value for chemists who intend to learn more on this emerging topic.”  (Anal Bioanal Chem, 1 October 2015)