Bioluminescence: Chemical Principles and Methods

Bioluminescence: Chemical Principles and Methods

by Osamu Shimomura
     
 

ISBN-10: 9812568018

ISBN-13: 9789812568014

Pub. Date: 09/28/2006

Publisher: World Scientific Publishing Company, Incorporated

This book is an authoritative monograph on the recent progresses in the chemistry of bioluminescence. It provides a comprehensive overview of the past and the latest developments in understanding the biochemical mechanisms of some 35 different types of luminous organisms, together with information helpful to students and researchers in an Appendix. It is the first

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Overview

This book is an authoritative monograph on the recent progresses in the chemistry of bioluminescence. It provides a comprehensive overview of the past and the latest developments in understanding the biochemical mechanisms of some 35 different types of luminous organisms, together with information helpful to students and researchers in an Appendix. It is the first and only book that provides chemical information on all currently known bioluminescence systems. Dr Shimomura is the leading practitioner in the field for the past half century, and is best known for his discovery of the jellyfish photoprotein aequorin and the green fluorescent protein. This book is the bible of bioluminescence, and is "a must read," not only for the students who study bioluminescence but also for those who work in various aspects relating to bioluminescence. This book will be an important source of chemical knowledge on bioluminescence for a long period of time in future.

Fully revised since its publication in 2006, it now incorporates the most recent advances in the subject area. A new section on "Green Fluorescent Protein" has been added at the end of Chapter 4. It contains an extensive reference section.

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Product Details

ISBN-13:
9789812568014
Publisher:
World Scientific Publishing Company, Incorporated
Publication date:
09/28/2006
Pages:
470
Product dimensions:
6.20(w) x 9.20(h) x 1.10(d)

Table of Contents

Abbreviations, Symbols and Definitions xiii

Introduction xvii

1 The Fireflies and Luminous Insects 1

1.1 The Fireflies 2

1.1.1 An overview of the firefly luminescence reaction 2

1.1.2 Firefly luciferin and oxyluciferin 5

1.1.3 Firefly luciferase 7

1.1.4 Assays of luciferase activity, ATP and luciferin 10

1.1.5 General characteristics of the bioluminescence of fireflies 11

1.1.6 Mechanism of firefly bioluminescence 15

1.1.7 Identification of light emitter 17

1.1.8 A note on the dioxetanone pathway and the 18O-incorporation experiment 20

1.2 Phengodidae and Elateroidae 24

1.2.1 Phengodidae 25

1.2.2 Elateridae 25

1.3 Diptera 26

1.3.1 The glow-worm Arachnocampa 26

1.3.2 The American glow-worm Orfelia 29

2 Luminous Bacteria 31

2.1 Factors Required for Bioluminescence 32

2.2 Bacterial Luciferase 33

2.3 Long-chain Aldehyde 35

2.4 Mechanism of Luminescence Reaction 38

2.5 Assay of Luciferase Activity 39

2.6 Quantum Yield of Long-chain Aldehydes 41

2.7 In vivo Luminescence of Luminous Bacteria 42

3 The Ostracod Cypridina (Vargula) and Other Luminous Crustaceans 49

3.1 The Ostracod Cypridina 51

3.1.1 Overview of Ostracoda 51

3.1.2 Cypridina hilgendorfii Müller 52

3.1.3 Research on Cypridina luminescence before 1955 55

3.1.4 Purification and crystallization of Cypridina luciferin 56

3.1.5 Properties of Cypridina luciferin 60

3.1.6 Oxyluciferin and etioluciferin 63

3.1.7 Purification and molecular properties of Cypridina luciferase 64

3.1.8 Luciferin-luciferase luminescence reaction 65

3.1.9 Quantum yield 71

3.2 Euphausiids Euphausia pacifica and Meganyctiphanes Norvegica 73

3.2.1 Involvement of the fluorescent compound F and protein P 74

3.2.2 Fluorescent compound F 75

3.2.3 Protein P 80

3.2.4 Luminescence reaction 81

3.3 The Decapod Shrimp Oplophorus gracilirostris 83

3.3.1 Oplophorus luciferase 83

3.3.2 Coelenterazine-luciferase reaction 85

3.4 Copepoda 89

4 The Jellyfish Aequorea and Other Luminous Coelenterates 91

4.1 The Hydrozoan Medusa Aequorea aequorea 92

4.1.1 History of the biochemical study of Aequorea bioluminescence 95

4.1.2 Extraction and purification of aequorin 96

4.1.3 Properties of aequorin 101

4.1.4 Discovery of the coelenterazine moiety in aequorin 112

4.1.5 Regeneration of aequorin from apoaequorin 114

4.1.6 Recombinant aequorin 117

4.1.7 Semisynthetic aequorins 119

4.1.8 The in vivo luminescence of Aequorea 130

4.2 The Hydroid Obelia (Hydrozoan) 131

4.2.1 Natural obelins 132

4.2.2 Recombinant obelin 133

4.3 The Hydrozoan Medusa Phialidium gregarium 136

4.4 Other Bioluminescent Hydrozoans 138

4.5 The Scyphozoans Pelagia and Periphylla 139

4.5.1 Pelagia noctiluca 139

4.5.2 Periphylla periphylla 139

4.6 The Anthozoan Renilla (Sea Pansy) 146

4.7 The Ctenophores 149

4.8 The green fluorescent protein (GFP) 154

4.8.1 Properties of Aequorea GFP 156

4.8.2 Chromophore of Aequorea GFP 158

4.8.3 Various natural GFPs 159

4.8.4 Various improved forms of GFP 162

5 The Coelenterazines 167

5.1 Discovery of Coelenterazine 167

5.2 Occurrence of Coelenterazine 168

5.3 Properties of Coelenterazine and its Derivatives 173

5.4 Chemi - and Bioluminescence Reactions of Coelenterazine 175

5.5 Various Chemical Reactions of Coelenterazine 182

5.6 Synthesis of Coelenterazines 185

5.7 Coelenterazine Luciferases 185

6 Luminous Mollusca 189

6.1 The Limpet Latia 190

6.2 The Clam Pholas dactylus 201

6.3 Luminous Squids (Cephalopoda) 208

6.3.1 The firefly squid Watasenia scintillans 209

6.3.2 The purpleback flying squid Symplectoteuthis oualaniensis (Tobi-ika) 214

6.3.3 The luminous flying squid Symplectoteuthis luminosa (Suji-ika) 219

7 Annelida 225

7.1 The Tubeworm Chaetopterus variopedatus 225

7.1.1 Biochemistry of the Luminescence of Chaetopterus variopedatus 226

7.1.2 Properties of the Chaetopterus photoprotein and its luminescence reaction 230

7.2 The Bermuda Fireworm Odontosyllis 233

7.3 Luminous Earthworms (Oligochaeta) 243

7.4 Polynoid Scaleworm Harmothoë lunulata 251

7.5 The Polychaete Tomopteris 255

8 Dinoflagellates and Other Protozoa 257

8.1 Radiolarians 257

8.2 Dinoflagellates 258

8.2.1 Cultivation and harvesting of dinoflagellates 259

8.2.2 Scintillons 260

8.2.3 The luciferase of Gonyaulax polyedra 261

8.2.4 Extraction and purification of dinoflagellate luciferin 264

8.2.5 Properties of dinoflagellate luciferin 266

8.2.6 Chemical structures of dinoflagellate luciferin and its oxidation products 269

8.2.7 Chemical mechanism of dinoflagellate bioluminescence 272

8.2.8 Luciferin binding protein of dinoflagellates 273

9 Luminous Fungi 275

9.1 An Overview on Fungal Bioluminescence 275

9.2 Early Studies on the Biochemistry of Luminous Fungi 277

9.3 Role of Superoxide in Fungal Luminescence 279

9.4 Studies on Panellus stipticus 284

9.4.1 Panal 285

9.4.2 Activation products of panal 287

9.4.3 PS-A and PS-B 290

9.4.4 Activation of PS-A and PS-B 292

9.4.5 Mechanism of the in vivo bioluminescence of P. stipticus 297

9.4.6 Synthetic studies of Panellus luciferin 300

9.5 Studies on Mycena citricolor 301

9.5.1 Luciferin obtained by Kuwabara and Wassink 301

9.5.2 Studies on the Mycena citricolor luminescence by the author 303

9.6 Summary on the Chemistry of Fungal Luminescence 307

10 Other Luminous Organisms 309

10.1 Ophiuroidea: Brittle Stars 309

10.1.1 The brittle star Ophiopsila californica 310

10.1.2 The brittle star Amphiura filiformis 314

10.2 Millipede Luminodesmus sequoiae (Diplopoda) 315

10.3 Centipede Orphaneus brevilabiatus (Chilopoda) 321

10.4 Hemicordata 322

10.4.1 The acorn worm Balanoglossus biminiensis 323

10.4.2 The luciferin of Ptychodera flava 325

10.5 Tunicates (Phylum Chordata) 327

10.6 The Luminous Fishes 329

10.6.1 Coastal and shallow-water fishes that utilize Cypridina luciferin 330

10.6.2 Oceanic deep-sea luminous fishes 334

10.6.3 Future research on fish bioluminescence 337

Appendix 339

A Taxonomic Classification of Selected Luminous Organisms 339

B Lists of Luciferins, Luciferases and Photoproteins Isolated 345

C Miscellaneous Technical Information 353

C1 Basic Principle of the Isolation of Bioluminescent Substances 353

C1.1 Reversible inhibition of bioluminescence 354

C1.2 Extraction of luciferin-luciferase systems 357

C1.3 Solubilization of proteins 357

C1.4 Purification 359

C2 Storage of Samples 360

C3 Measurement of Luminescence 363

C4 Calibration of Luminometer and the Measurement of Quantum Yield 365

C5 Detection and Assay of Coelenterazine, its Derivatives, and Other Important Substances in Bioluminescence 367

C5.1 Assay of coelenterazine 367

C5.2 Assay of the coelenterazine luciferase activity 368

C5.3 Assay of the stabilized forms of coelenterazine 369

C5.4 Assay of dehydrocoelenterazine 370

C5.5 Assay of Cypridina luciferin 370

C5.6 Assay of Cypridina luciferase 371

C5.7 Assay of Ca2+-sensitive photoproteins 372

C5.8 Measuring bioluminescence in the field 373

C6 18O-Labeling of the Reaction Product CO2 374

C7 Glassblowing 378

D Advice to Students Who are Interested in Studying the Chemistry of Bioluminescence 379

References 383

Index 457

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