BOOK
Organoselenium Compounds in Biology and Medicine
Vimal Kumar Jain | K Indira Priyadarsini
(2017)
Additional Information
Book Details
Abstract
Organoselenium shows incredible promise in medicine, particularly cancer therapy. This book discusses organoselenium chemistry and biology in the context of its therapeutic potential, taking the reader through synthetic techniques, bioactivity and therapeutic applications.
Divided into three sections, the first section describes synthetic advances in bioactive selenium compounds, revealing how organoselenium compound toxicity, redox properties and specificity can be further tuned. The second section explains the biophysics and biochemistry of organoselenium compounds, as well as selenoproteins. The final section closes with several chapters devoted to therapeutic and medicinal applications of organoselenium compounds, covering radioprotectors, anticancer agents and antioxidant behaviour.
With contributions from leading global experts, this book covers recent advances in the field and is an ideal reference for those researching organoselenium compounds.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Contents | ix | ||
| Preface | v | ||
| Chapter 1 An Overview of Organoselenium Chemistry: From Fundamentals to Synthesis | 1 | ||
| 1.1 Introduction | 1 | ||
| 1.2 General Considerations | 3 | ||
| 1.3 NMR Spectroscopy | 5 | ||
| 1.4 Mass Spectrometry | 7 | ||
| 1.5 X-ray Crystallography | 7 | ||
| 1.6 Synthesis of Organoslenium Compounds | 12 | ||
| 1.6.1 Diorganodiselenides | 12 | ||
| 1.6.2 Selenols | 15 | ||
| 1.6.3 Diorganoselenides | 17 | ||
| 1.6.4 Diorganoselenoxides | 18 | ||
| 1.6.5 Selenenyl Sulfides | 19 | ||
| 1.6.6 Organoselenium Halides | 20 | ||
| 1.6.7 Selenenic, Seleninic and Selenonic Acids | 22 | ||
| References | 25 | ||
| Synthetic Advances on Bioactive Selenium Compounds | 35 | ||
| Chapter 2 Looking Beyond the Traditional Idea of Glutathione Peroxidase Mimics as Antioxidants | 37 | ||
| 2.1 Introduction | 37 | ||
| 2.2 Chemistry of Organoselenium GPx-mimetics | 41 | ||
| 2.2.1 Ebselen and Its Derivatives or Analogues | 41 | ||
| 2.2.2 Diselenides | 54 | ||
| 2.2.3 Selenides and Spiroselenuranes | 60 | ||
| 2.3 Looking Beyond the Simple Concept of GPx Mimetics | 66 | ||
| 2.3.1 Targeting Biologically Relevant Thiols | 66 | ||
| 2.3.2 Targeting ‘‘Zinc-finger\" Domains | 69 | ||
| 2.3.3 GPx Mimics as Probes and Biosensors | 70 | ||
| Acknowledgments | 71 | ||
| References | 71 | ||
| Chapter 3 Synthesis of Organoselenium Compounds with Potential Biological Activities | 77 | ||
| 3.1 Introduction | 77 | ||
| 3.2 Synthesis of Organoselenium Compounds as Antioxidants | 78 | ||
| 3.3 Organoselenium Compounds as Antithyroid Agents | 92 | ||
| 3.4 Organoselenium Compounds as Anticancer Agents | 95 | ||
| 3.5 Selenium Compounds as Anti-Alzheimer's Disease Agents | 104 | ||
| 3.6 Selenium Compounds as Antimicrobial Agents | 106 | ||
| 3.7 Organoselenium Compounds as Antiviral Agents | 109 | ||
| 3.8 Organoselenium Compounds as Xanthine Oxidase Inhibitors | 111 | ||
| 3.9 Organoselenium Compounds as Anti-inflammatory Agents | 112 | ||
| 3.10 Organoselenium Compounds as Antidiabetic Agents | 112 | ||
| 3.11 Organoselenium Compounds as Antidepressants | 113 | ||
| References | 113 | ||
| Chapter 4 The Relevant Chemistry of Imidazoline-2-selone Donors with Potential Biological Applications | 122 | ||
| 4.1 Introduction | 122 | ||
| 4.2 General Reactivity of Heterocyclic Pentatomicthio- and Seleno-amides Towards Dihalogens and Inter-halogens | 125 | ||
| 4.2.1 MMI (2) and MSeI (3) and Their Reactivity Towards I2 | 140 | ||
| 4.3 Anti-oxidant Action of Imidazoline-2-chalcogenone Derivatives via Metal Binding | 141 | ||
| 4.4 Conclusion | 145 | ||
| Acknowledgments | 145 | ||
| References | 145 | ||
| Chapter 5 Organoselenium Cations: Structures, Reactivity and Applications | 150 | ||
| 5.1 Introduction | 150 | ||
| 5.2 Organoselenenium Cations | 152 | ||
| 5.3 Preparation of Selenium Dications | 157 | ||
| 5.4 Organoseleniranium and Selenirenium Cations | 160 | ||
| 5.5 Diselenium Cations | 163 | ||
| 5.6 Applications of Organoselenium Cations | 164 | ||
| Acknowledgments | 174 | ||
| References | 174 | ||
| Chapter 6 Organoselenide Fluorophores for Probing Reactive Oxygen Species and Heavy Metals | 178 | ||
| 6.1 Introduction | 178 | ||
| 6.2 ROS Detection | 179 | ||
| 6.2.1 ROS Detection Since 2012 | 183 | ||
| 6.3 Ebselen Derivativization in ROS Chemosensing | 183 | ||
| 6.4 Heavy Metals and their Detection Through the use of Selenium | 188 | ||
| 6.5 Conclusion and a Glance at the Future | 191 | ||
| Acknowledgments | 193 | ||
| References | 193 | ||
| Bio-physics, Chemistry and Effect on Oxidative Stress of Organoselenium Compounds | 197 | ||
| Chapter 7 Non-bonded Selenium...Heteroatom Interactions in Selenoenzyme Glutathione Peroxidase and Mimics | 199 | ||
| 7.1 Introduction | 199 | ||
| 7.2 Modes of Weak Interactions Involving a Selenium Atom | 201 | ||
| 7.2.1 NH...Se and Related Hydrogen Bonds | 202 | ||
| 7.2.2 Non-bonded O...Se and Related Interactions | 202 | ||
| 7.3 Catalytic Cycle of GPx and the Intermediates | 204 | ||
| 7.3.1 GPx-SeH | 205 | ||
| 7.3.2 GPx-SeOH | 206 | ||
| 7.3.3 GPx-SeSG | 207 | ||
| 7.4 Design of GPx Mimics | 209 | ||
| 7.4.1 Ebselen and Related GPx Models | 210 | ||
| 7.4.2 Aromatic Diselenides with Functional Groups | 211 | ||
| 7.4.3 Selenocysteine and Related GPx Models | 213 | ||
| 7.4.4 Designed Sec-containing Peptides | 214 | ||
| 7.5 Conclusions and Perspectives | 216 | ||
| References | 217 | ||
| Chapter 8 Carbohydrate-derived Organoselenium Compounds: Synthesis and Application in the Structural Analysis of Biomolecules | 223 | ||
| 8.1 Introduction | 223 | ||
| 8.2 Selenium in Carbohydrate Chemistry | 224 | ||
| 8.2.1 Selenoether Pseudo-carbohydrates | 224 | ||
| 8.2.2 Selenosugars | 226 | ||
| 8.2.3 Selenoglycosides | 229 | ||
| 8.3 Seleninates and Selenonates | 231 | ||
| 8.3.1 Reactions with Active Site Functionality | 232 | ||
| 8.3.2 Aromatic Organoselenium Compounds | 234 | ||
| 8.4 Selenium in DNA/RNA | 236 | ||
| 8.4.1 Nucleobase-modified Analogues | 236 | ||
| 8.4.2 Phosphate Backbone-modified Analogues | 239 | ||
| 8.5 Application in Structural Analysis | 241 | ||
| 8.5.1 Se-Carbohydrate-Protein Complexation | 243 | ||
| 8.5.2 Selenium in NMR Structural Analysis | 244 | ||
| References | 247 | ||
| Chapter 9 Reaction of Selenium Compounds with Reactive Oxygen Species and the Control of Oxidative Stress | 254 | ||
| 9.1 Introduction: Oxidant Formation During Inflammation | 254 | ||
| 9.2 Antioxidant and Protective Systems | 256 | ||
| 9.3 Oxidative Chemistry of Sulfur and Selenium Compounds | 257 | ||
| 9.3.1 Selenols | 260 | ||
| 9.3.2 Selenoethers and Thioethers | 263 | ||
| 9.3.3 Diselenides and Disulfides | 266 | ||
| 9.4 Recycling and Repair of Selenium and Sulfur Oxidation Products | 268 | ||
| 9.5 Conclusions | 269 | ||
| Abbreviations | 269 | ||
| Acknowledgments | 269 | ||
| References | 270 | ||
| Chapter 10 Reactive Selenium Species: Redox Modulation, Antioxidant, Antimicrobial and Anticancer Activities | 277 | ||
| 10.1 Selenium: 200 Years Before the Mast | 278 | ||
| 10.2 The Docs Bark but the Caravan Moves on | 279 | ||
| 10.3 Natural Selenium Nanoparticles from Common Bacteria | 280 | ||
| 10.4 Selenoneine or ‘‘pimp my RSS | 282 | ||
| 10.5 Selenomethionine, Selenoxides and Selenones | 284 | ||
| 10.6 Beyond the Traditional Se-N Bond | 287 | ||
| 10.7 Selenoesters and Anhydrides: Unstable Pipe Dreams or Elegant Pro-drugs | 290 | ||
| 10.8 Selenium-based Redox Catalysts: Effective and Selective Rather than Fast and Furious | 292 | ||
| 10.9 Stick it and Click it like Beckham | 294 | ||
| 10.10 Caveats Before Caviar | 295 | ||
| 10.11 Conclusions | 296 | ||
| Abbreviations | 297 | ||
| Acknowledgments | 298 | ||
| References | 298 | ||
| Chapter 11 Ebselen and Thioredoxin Systems in Human Health, Disease and Therapeutic Potential | 303 | ||
| 11.1 Introduction | 303 | ||
| 11.1.1 Mammalian and Bacterial Thioredoxin System | 303 | ||
| 11.1.2 The Relationship of the Thioredoxin System with the Glutathione System | 305 | ||
| 11.1.3 Ebselen | 305 | ||
| 11.2 Interaction of Ebselen with Thioredoxin Systems | 307 | ||
| 11.2.1 Reaction of Ebselen with Mammalian Thioredoxin Systems | 307 | ||
| 11.2.2 Ebselen as an Antioxidant to Remove ROS Together with the Mammalian Trx System | 307 | ||
| 11.2.3 Inhibition of the Bacterial Thioredoxin System by Ebselen | 307 | ||
| 11.2.4 Reaction of Ebselen/Ebsulfur with other Disulfide Reductases | 308 | ||
| 11.3 Therapeutic Potential of Ebselen in Disease | 308 | ||
| 11.3.1 Ebselen use in Human Infections | 308 | ||
| 11.3.2 Ebselen use in other Diseases | 312 | ||
| 11.4 Concluding Remarks | 313 | ||
| References | 313 | ||
| Therapeutic Applications of Organoselenium Compounds | 317 | ||
| Chapter 12 History and Development of Selenium-based Radioprotectors: Distinctions between the Inorganic and Organic Forms | 319 | ||
| 12.1 Radiation Exposure and Radioprotection | 319 | ||
| 12.2 Selenium as a Radioprotector | 321 | ||
| 12.2.1 Inorganic Selenium | 321 | ||
| 12.2.2 Organoselenium Compounds | 324 | ||
| 12.2.3 Organoselenium Radioprotectors Developed by our Group | 326 | ||
| 12.2.4 Molecular Mechanisms Contributing to the Radioprotective Effect of Selenium | 327 | ||
| 12.3 Selenium in Clinical Radiotherapy | 329 | ||
| 12.3.1 Effect of Selenium Supplementation on Radiation Toxicities | 330 | ||
| 12.3.2 Effect of Radiation Therapy on Selenium status in the Body | 336 | ||
| 12.4 Conclusions | 336 | ||
| Acknowledgments | 337 | ||
| References | 337 | ||
| Chapter 13 Toxicology and Anticancer Activity of Synthetic Organoselenium Compounds | 342 | ||
| 13.1 Introduction | 342 | ||
| 13.2 Selenium Toxicology | 344 | ||
| 13.2.1 Inorganic Selenium | 344 | ||
| 13.2.2 Naturally Occurring Organoselenium Compounds | 344 | ||
| 13.2.3 Synthetic Organoselenium Compounds | 347 | ||
| 13.3 Environmental or Dietary Toxicity of Selenium: A Neglected Problem? | 348 | ||
| 13.4 Selenium in Cancer | 349 | ||
| 13.4.1 Organoselenium Compounds and Cancer | 352 | ||
| 13.5 The Mechanism of Action of Synthetic Organoselenium Compounds as Anti-cancer Agents | 352 | ||
| 13.5.1 Ebselen | 353 | ||
| 13.5.2 Diselenides | 354 | ||
| 13.5.3 Selenocyanates | 355 | ||
| 13.5.4 3'-Azido-3'-deoxythymidine Derivatives | 356 | ||
| 13.6 In silico Study as a Virtual Screening of Potential Anticancer Drugs | 357 | ||
| 13.6.1 Thioredoxin Reductase | 358 | ||
| 13.6.2 Tubulin | 360 | ||
| 13.6.3 Histone Deacetylase | 360 | ||
| 13.6.4 Zinc Finger Proteins | 362 | ||
| 13.6.5 DNA | 364 | ||
| 13.7 Conclusion | 365 | ||
| References | 366 | ||
| Chapter 14 Metabolism of Selenium/Selenocystine and Their Roles in the Prevention and Treatment of Human Cancer | 377 | ||
| 14.1 Introduction | 377 | ||
| 14.2 Organic Selenium Compounds and Their Structures | 379 | ||
| 14.3 Transport and Metabolism of Organic Selenium Compounds in Humans | 379 | ||
| 14.3.1 Transport | 380 | ||
| 14.4 Metabolism | 382 | ||
| 14.4.1 Selenocystine/Selenomethionine | 382 | ||
| 14.4.2 Methylselenocysteine | 386 | ||
| 14.5 Selenium Compounds and Cancer Prevention | 388 | ||
| 14.6 Key Aspects of Selenium Compounds as Prospective Cancer Therapeutics | 390 | ||
| 14.6.1 Pharmacokinetics | 393 | ||
| 14.7 Conclusion | 394 | ||
| Acknowledgments | 395 | ||
| References | 395 | ||
| Chapter 15 Organoselenium Compounds as Cancer Therapeutic Agents | 401 | ||
| 15.1 Introduction | 401 | ||
| 15.2 Selenium and Cancer Treatment | 402 | ||
| 15.2.1 Increased Oxidative Stress as a Selective Anticancer Strategy | 402 | ||
| 15.3 Organoselenium Compounds as Potential Anticancer Agents | 405 | ||
| 15.3.1 Selenoaminoacid Derivatives | 405 | ||
| 15.3.2 Selenides and Diselenides | 418 | ||
| 15.3.3 Selenocyantes | 420 | ||
| 15.3.4 Selenoesters | 422 | ||
| 15.3.5 Ethaselen and Ebselen | 423 | ||
| 15.3.6 Other Seleno-heterocycles | 424 | ||
| 15.3.7 Selenium-non-steroidal Anti-inflammatory Drugs | 426 | ||
| 15.3.8 Selenium-containing Histone Deacetylase Inhibitors | 426 | ||
| 15.4 Conclusion | 427 | ||
| References | 427 | ||
| Chapter 16 Cancer Prevention by Different Forms of Selenium | 436 | ||
| 16.1 Introduction | 436 | ||
| 16.2 Does Selenium Prevent Cancer? | 438 | ||
| 16.3 Mechanisms by which Selenium can Prevent Cancer | 439 | ||
| 16.3.1 In Vitro Studies | 439 | ||
| 16.3.2 Effects of Chemical Forms of Selenium on Selenoprotein Levels | 440 | ||
| 16.3.3 Selenium and the Repair of DNA Damage | 441 | ||
| 16.3.4 Animal Studies | 442 | ||
| 16.4 Human Studies | 443 | ||
| 16.5 The Impact of SELECT on Evaluating Chemoprevention with Selenium | 445 | ||
| 16.6 Which forms of Selenium Should be Investigated for Cancer Prevention? | 445 | ||
| 16.7 Conclusions | 446 | ||
| Acknowledgments | 447 | ||
| References | 447 | ||
| Subject Index | 452 |