Handbook of In Vivo Chemistry in Mice : From Lab to Living System

Provides timely, comprehensive coverage of in vivo chemical reactions within live animals This handbook summarizes the interdisciplinary expertise of both chemists and biologists performing in vivo chemical reactions within live animals. By comparing and contrasting currently available chemical and biological techniques, it serves not just as a collection of the pioneering work done in animal-based studies, but also as a technical guide to help readers decide which tools are suitable and best for their experimental needs. The Handbook of In Vivo Chemistry in Mice: From Lab to Living System introduces readers to general information about live animal experiments and detection methods commonly used for these animal models. It focuses on chemistry-based techniques to develop selective in vivo targeting methodologies, as well as strategies for in vivo chemistry and drug release. Topics include: currently available mouse models; biocompatible fluorophores; radionuclides for radiodiagnosis/radiotherapy; live animal imaging techniques such as positron emission tomography (PET) imaging; magnetic resonance imaging (MRI); ultrasound imaging; hybrid imaging; biocompatible chemical reactions; ligand-directed nucleophilic substitution chemistry; biorthogonal prodrug release strategies; and various selective targeting strategies for live animals. -Completely covers current techniques of in vivo chemistry performed in live animals -Describes general information about commonly used live animal experiments and detection methods -Focuses on chemistry-based techniques to develop selective in vivo targeting methodologies, as well as strategies for in vivo chemistry and drug release -Places emphasis on material properties required for the development of appropriate compounds to be used for imaging and therapeutic purposes in preclinical applications Handbook of In Vivo Chemistry in Mice: From Lab to Living System will be of great interest to pharmaceutical chemists, life scientists, and organic chemists. It will also appeal to those working in the pharmaceutical and biotechnology industries. Cover......Page 1 Title Page......Page 5 Copyright......Page 6 Contents......Page 7 1.1 Introduction......Page 17 1.2 Origin and History of Laboratory Mice......Page 18 1.3.1 Wild‐Derived Mice......Page 19 1.3.3 Hybrid Mice......Page 20 1.3.6 Congenic Mice......Page 24 1.4.2 Transgenesis......Page 25 1.4.3 Targeted Mutagenesis......Page 27 1.4.5 Cre–loxP System......Page 29 1.4.6 CRISPR/Cas9 System......Page 31 1.6 Germ‐Free Mice......Page 32 1.9 Immunocompetent and Immunodeficient Mice......Page 34 1.11.2 Breeding Systems and Mating Schemes......Page 35 1.15 Parental Behavior and Rearing Pups......Page 37 1.16 Growth of Pups......Page 38 1.18 Record Keeping and Colony Organization......Page 39 1.20 Animal Models in Preclinical Research......Page 40 References......Page 45 2.1 Introduction......Page 49 2.3.1 Substance Characteristics......Page 50 2.3.2 Vehicle Characteristics......Page 51 2.3.3 Frequency and Volume of Administration......Page 52 2.4 Anesthesia......Page 53 2.4.2 Injectable Agents......Page 54 2.5 Euthanasia......Page 56 2.6 Administration......Page 57 2.6.2 Parenteral Administration......Page 58 2.6.2.2 Intraperitoneal Administration......Page 60 2.6.2.7 Epicutaneous Administration......Page 62 2.6.2.9 Inhalational Administration......Page 67 2.6.2.10 Retro‐orbital Administration......Page 68 References......Page 69 3.1.1 Basics of Luminescence......Page 71 3.1.2 Appropriate Wavelengths for Live Animal Imaging......Page 72 3.2.1 Fluorescent Molecules for Live Animal Imaging......Page 74 3.2.2 How to Detect Fluorescence in Live Animals?......Page 77 3.2.3 Activatable Probes......Page 78 3.2.5 Application of Fluorescence Imaging to Drug Development......Page 84 3.3 Luminescence Imaging in Live Animals......Page 85 3.3.1.1 Firefly/Beetle Luciferin–Luciferase System......Page 86 3.3.1.2 Coelenterazine‐Dependent Luciferase System......Page 92 3.3.1.3 Chemiluminescence System......Page 98 3.3.3 Luciferase‐Based Bioluminescence Probes for In Vivo Imaging......Page 100 References......Page 103 4.1 Introduction......Page 119 4.2 High‐Frequency Ultrasound Imaging......Page 121 4.3 Ultrasound Contrast Agents......Page 125 4.4 Photoacoustic Imaging......Page 128 4.5.1 Cardiovascular......Page 131 4.5.2 Oncology......Page 136 4.5.3 Developmental Biology......Page 137 References......Page 139 5.1 Introduction......Page 143 5.2 Brief History of PET......Page 144 5.3 Principles of PET......Page 145 5.4 Small‐Animal PET Scanners......Page 149 5.5.1 Metabolic Probe......Page 150 5.5.2 Specific Receptor Targeting Probe......Page 151 5.5.3 Gene Expression......Page 152 5.5.5 Microenvironment Probe......Page 153 5.5.6 Biological Processes......Page 154 5.5.8 Nanoparticles......Page 156 5.6.1 PET in Oncology Model......Page 157 5.6.1.2 Personal Treatment Screening......Page 158 5.6.1.3 Therapeutic Effect Monitoring......Page 159 5.6.1.5 Drug Discovery......Page 160 5.6.2 PET in Cardiology Model......Page 161 5.6.3 PET in Neurology Model......Page 162 5.7 PET Image Analysis......Page 163 5.8 Outlook for the Future......Page 164 Reference......Page 165 6.1 Introduction......Page 167 6.2 SPECT Devices Used in Small Animals......Page 168 6.2.1 Innovative Preclinical Full‐Body SPECT Imager for Rats and Mice: γ‐CUBE......Page 171 6.2.3 Innovative Preclinical Full‐Body CT Imager for Rats and Mice: X‐CUBE......Page 172 6.2.5 Selected Applications Acquired on the CUBES......Page 173 6.2.5.2 PET Imaging with β‐CUBE......Page 174 6.2.5.3 CT Imaging with X‐CUBE......Page 177 6.3.2 Characteristics of SPECT Imaging Probes......Page 178 6.4 Radiolabeling......Page 179 6.4.2 Radiolabeling with Technetium‐99m......Page 180 6.4.5 Aromatic Electrophilic Substitution Reaction......Page 187 6.5 In Vivo Imaging of Disease Models......Page 188 6.5.1.1 Alzheimer's Disease......Page 189 6.5.1.2 Parkinson's Disease......Page 190 6.5.1.3 Cerebral Ischemia......Page 192 6.5.2.2 Myocardial Ischemia......Page 193 6.5.2.3 Imaging of Cancer......Page 194 6.6 Conclusions......Page 195 References......Page 196 7.1 Introduction......Page 201 7.2.1 Radiotherapy with β‐Emitting Nuclides......Page 202 7.2.2 Radiotherapy Using α‐Emitting Nuclides......Page 204 7.3.1 Labeled Target Compounds......Page 207 7.3.2 211At‐Labeled Compounds......Page 208 7.3.3 Chelating Agents for 90Y, 177Lu, 225Ac, 213Bi......Page 209 7.3.4.1 Octreotate (TATE) and [Tyr3]‐Octreotide (TOC)......Page 211 7.3.4.5 Minigastrin......Page 212 7.3.6 Examples of Radiotherapeutic Agents and Target Diseases......Page 213 7.4.1 Radiotheranostics Probe......Page 216 7.4.3 Expectations and Challenges in Radiotheranostics......Page 218 7.4.4 Boron Neutron Capture Therapy (BNCT)......Page 219 7.4.5.2 Sodium Borocaptate (BSH)......Page 220 References......Page 221 8.1 Introduction......Page 225 8.2.1 Origin of Metabolic Glycan Engineering......Page 226 8.2.2 Expansion of the Methodology to Include Unnatural Functional Groups and Bio‐orthogonal Elaboration......Page 229 8.3.1 Bio‐orthogonal Chemistries Amenable to Deployment in Live Animals......Page 232 8.3.2 Bio‐orthogonal Chemistries Amenable to Deployment on Cells......Page 237 8.4.1 Deployment of Unnatural Monosaccharides in Mammalian Cells......Page 239 8.4.2 Unnatural Sugars that Label Glycans on Bacterial Cells......Page 241 8.5 Cell‐ and Tissue‐Specific Delivery of Unnatural Sugars......Page 242 8.5.2 Metabolically Label Cells Ex vivo Before Introducing Them In vivo......Page 243 8.5.4 Employ Tissue‐Specific Enzymes to Release Monosaccharide Substrates......Page 245 8.5.5 Deliver Monosaccharide Substrates via Liposomes......Page 247 8.6.1 Imaging Glycans in Mice......Page 250 8.6.2 Covalent Delivery of Therapeutics in Mice......Page 252 8.7.1 Zebra Fish......Page 253 8.7.2 Worms......Page 255 8.8.1 Metabolic Glycan Engineering Offers a Test Bed for Bio‐orthogonal Chemistries......Page 256 References......Page 257 9.1.1 IEDDA Chemistry Between trans‐Cyclooctene and Tetrazine......Page 265 9.2 In Vivo Applications of IEDDA Chemistry......Page 267 9.2.1 Pretargeting Approach for Cell Imaging......Page 268 9.2.2 Pretargeting Approach for In Vivo Imaging......Page 272 9.2.3 Application of the Pretargeting Strategy for In Vivo Radio Imaging......Page 275 9.2.4 In Vivo Drug Activation Using Bond‐cleaving Bio‐orthogonal Chemistry......Page 276 9.2.5 Reloadable Materials Allow Local Prodrug Activation......Page 281 9.2.6 Reloadable Materials Allow Local Prodrug Activation Using IEDDA Chemistry......Page 282 9.2.7 Controlled Activation of siRNA Using IEDDA Chemistry......Page 288 9.3 Future Outlook......Page 290 References......Page 293 10.1 Introduction......Page 297 10.2.1 Ligand‐Directed Tosyl Chemistry......Page 298 10.2.2 Ligand‐Directed Acyl Imidazole Chemistry......Page 300 10.3 Labeling Chemistry of Targeted Covalent Inhibitors......Page 303 10.3.1 Michael Acceptors......Page 306 10.3.2 Haloacetamides......Page 309 10.3.3 Activated Esters, Amides, Carbamates, and Ureas......Page 311 10.3.4 Sulfur(VI) Fluorides......Page 313 10.3.5 Other Warheads and Reactions......Page 316 10.4 Conclusion......Page 317 References......Page 318 11.1 Introduction......Page 325 11.2.1 Protein Decaging......Page 326 11.2.2 Protein Bioconjugation......Page 327 11.2.3 Small Molecule – Bond Formation......Page 335 11.2.4 Small Molecule – Bond Cleavage......Page 340 11.3.1 ArMs Utilizing Naturally Occurring Metals......Page 348 11.3.2 ArMs Utilizing Abiotic Transition Metals......Page 351 11.4 Concluding Remarks......Page 356 References......Page 359 12.1 Introduction......Page 371 12.2 Catalytic Photo‐oxygenation of Aβ Using a Flavin–Peptide Conjugate......Page 373 12.3 On–Off Switchable Photo‐oxygenation Catalysts that Sense Higher Order Amyloid Structures......Page 374 12.4 Near‐Infrared Photoactivatable Oxygenation Catalysts: Application to Amyloid Disease Model Mice......Page 379 12.5 Closing Remarks......Page 383 References......Page 384 13.1 Introduction......Page 389 13.2.1 Physicochemical Properties of NPs......Page 391 13.2.2 Surface Functionalization......Page 395 13.2.3 Stimuli‐Responsive Nanomaterials......Page 397 13.3.1 Lipidic Nanoplatforms......Page 400 13.3.2 Polymer‐Based Nanoplatforms......Page 405 13.3.3 Inorganic Nanoplatforms......Page 407 13.3.4 Biomimetic Cell‐Derived Nanoplatforms......Page 409 13.4 Conclusions......Page 410 References......Page 411 14.1 Introduction......Page 417 14.2.1 UV Light‐Triggered Photocaged Strategy......Page 419 14.2.2 UV Light‐Mediated Photoisomerization Strategy......Page 421 14.3 Visible Light‐Responsive Theranostics......Page 424 14.4 Near‐Infrared (NIR) Light‐Responsive Theranostics......Page 426 14.4.1 NIR Light‐Mediated Drug Delivery Approach......Page 427 14.4.2 NIR Light‐Mediated Photodynamic Therapy (PDT) Approach......Page 431 14.4.3 NIR Light‐Mediated Photothermal Therapy (PTT) Approach......Page 435 14.5 Conclusion and Prospects......Page 437 References......Page 439 15.1 Introduction......Page 449 15.1.1 Light‐Sensitive Liposomes......Page 450 15.2.1 Light‐Induced Oxidation......Page 451 15.2.2 Photocrosslinking......Page 452 15.2.3 Photoisomerization......Page 454 15.2.4 Photocleavage......Page 456 15.2.5 Photothermal Release......Page 458 References......Page 460 16.1 Introduction......Page 467 16.2.1 Natural Ligands and Biomimetics......Page 468 16.2.2 Phage Display Peptide Library Screening......Page 470 16.2.3 Synthetic Peptide Library Screening......Page 474 16.3.1 Therapeutic Peptides......Page 476 16.3.1.2 Peptide Conjugates......Page 480 16.3.2.1 Peptide–Drug Conjugates......Page 481 16.3.2.2 Peptide‐Targeted Nanoparticles......Page 483 16.4 Molecular Imaging Mediated by Targeting Peptides......Page 485 16.4.1 Optical Imaging......Page 486 16.4.1.2 Integrin αvβ3 – RGD Tripeptide Targeting Probes:......Page 487 16.4.2 Positron Emission Tomography......Page 488 16.4.3 Magnetic Resonance Imaging......Page 489 16.5 Summary and Future Perspectives......Page 490 References......Page 491 17.1 Introduction......Page 505 17.2 Liver and Liver‐Based Disease Targeting......Page 507 17.2.1 Parenchymal Cell Targeting......Page 508 17.2.2 Nonparenchymal Cell Targeting......Page 514 17.3 Immune System Targeting......Page 517 17.3.2 Peritoneal Macrophage Targeting......Page 519 17.3.4 Brain Macrophage Targeting......Page 520 17.4 Bacterial Cell Targeting......Page 521 17.5.1 Natural Monosaccharide‐Based Methods......Page 522 17.5.2 Synthetic Sugars......Page 524 17.5.3 Complex Glycan Scaffold......Page 527 References......Page 530 Index......Page 547 EULA......Page 563 Of Currently Available Mouse Models / Ami Ito, Namiko Ito, Kimie Niimi, Takashi Arai, Eiki Takahashi -- General Notes of Chemical Administration to Live Animals / Ami Ito, Namiko Ito, Takashi Arai, Eiki Takahashi, Kimie Niimi -- Optical-Based Detection in Live Animals / Mikako Ogawa, Hideo Takakura -- Ultrasound Imaging in Live Animals / Francesco Faita -- Positron Emission Tomography (PET) Imaging in Live Animals / Xiaowei Ma, Zhen Cheng -- Single-Photon Emission Computed Tomographic Imaging in Live Animals / Yusuke Yagi, Hidekazu Kawashima, Kenji Arimitsu, Koki Hasegawa, Hiroyuki Kimura -- Radiotherapeutic Applications / Koki Hasegawa, Hidekazu Kawashima, Yusuke Yagi, Hiroyuki Kimura -- Metabolic Glycan Engineering in Live Animals: Using Bio-orthogonal Chemistry to Alter Cell Surface Glycans / Danielle H Dube, Daniel A Williams -- In Vivo Bioconjugation Using Bio-orthogonal Chemistry / Maksim Royzen, Nathan Yee, Jose M Mejia Oneto -- In Vivo Targeting of Endogenous Proteins with Reactive Small Molecules / Naoya Shindo, Akio Ojida -- In Vivo Metal Catalysis in Living Biological Systems / Kenward Vong, Katsunori Tanaka -- Chemical Catalyst-Mediated Selective Photo-oxygenation of Pathogenic Amyloids / Youhei Sohma, Motomu Kanai -- Nanomedicine Therapies / Patrícia Figueiredo, Flavia Fontana, Hélder A Santos -- Photoactivatable Targeting Methods / Xiangzhao Ai, Ming Hu, Bengang Xing -- Photoactivatable Drug Release Methods from Liposomes / Hailey I Kilian, Dyego Miranda, Jonathan F Lovell -- Peptide Targeting Methods / Ruei-Min Lu, Chien-Hsun Wu, Ajay V Patil, Han-Chung Wu -- Glycan-Mediated Targeting Methods / Kenward Vong, Katsunori Tanaka, Koichi Fukase