Chemiluminescence and bioluminescence : past, present and future

608 Pages·2010·272.743 MB·English

by  A Roda

Chemiluminescence and Bioluminescence
Past, Present and Future

Chemiluminescence and
Bioluminescence
Past, Present and Future
Edited by
Aldo Roda
Department of Pharmaceutical Sciences, University of Bologna-Alma Mater
Studiorum, Bologna, Italy
ISBN:978-1-84755-812-1
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rRoyalSocietyofChemistry2011
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Preface
The use of chemiluminescence and bioluminescence detection techniques in
various fields of analytical and bioanalytical chemistry is continuously
expanding thanks to recent achievements that have made available both new
chemical or molecular biology tools and advanced instrumentation for light
measurement and imaging.
The recent 2008 Nobel Prize in Chemistry awarded to Osamu Shimomura,
Martin Chalfie and Roger Y. Tsien for the discovery and development of the
green fluorescent protein (GFP) testifies to the importance of luminescence in
biosciences.
The observation of bioluminescence in nature has stimulated, in the last 50
years, basic photophysics and biochemical research aimed at explaining dif-
ferentaspectsofthisfascinatingphenomenon,suchasunravellingitsfunctions
innature,studyingtheevolutionofbioluminescentspeciesandinvestigatingits
biochemicalmechanisms. As aresult, manybioluminescentsystems have been
carefullycharacterizedandvariousluciferinsandluciferaseenzymeshavebeen
isolated and are nowadays available as analytical tools. Nevertheless, much
work needs to be done, since many bioluminescent marine and terrestrial sys-
tems are still unknown.
Disclosure of the fine mechanism responsible for light emission in biolumi-
nescent systems also enabled scientists to design new synthetic chemilumines-
cent compounds, exploiting the knowledge of which functional groups are
responsibleforlightemissioninnature.Allworkperformedinthe1500–1700s
ontheobservationandaccurateclassificationofbioluminescentorganismsand
the early attempts to demonstrate the mechanisms of the light emission phe-
nomenonpavedthewayforsubsequentachievements,particularlyattheendof
the 1800s and during the 1900s. Nowadays, we have extraordinary tools,
allowing us to detect a few molecules in a complex sample.
In recent years, tremendous progress in the chemiluminescence field has
occurred, thanks to the development of new chemical probes, enhancers and
advanced instrumentation. Bio- and chemiluminescence have been employed
successfully in biospecific assays, exploiting the high detectability of such
ChemiluminescenceandBioluminescence:Past,PresentandFuture
EditedbyAldoRoda
rRoyalSocietyofChemistry2011
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v
vi Preface
detection systems in combination with high specificity of target recognition
offered by antibodies and nucleic acid probes. Furthermore, the intrinsic high
sensitivity of bio- and chemiluminescence in small reaction volumes has also
allowedthedevelopmentofhigh-throughputscreeningmethods,thusboosting
the drug discovery process. The possibility of coupling bio- or chemilumines-
cent reactions with other enzyme reactions has led to amplified enzyme-based
assayssuitableforautomationandminiaturizationusingimmobilizedenzymes.
Finally, the availability of sensitive and compact light detectors has allowed
successful implementation of bio- and chemiluminescence detections in por-
table analytical devices.
Bioluminescent reporter gene technology has propelled revolutionary
advances in many fields of basic and applied science, from drug discovery to
environmental monitoring. Thanks to its high sensitivity, bioluminescence has
been widely used to monitor cellular events and unravel the molecular
mechanisms associated with signal transduction and gene expression. More
recently, its potential has been also applied to monitor protein–protein inter-
actions via resonance energy transfer processes or split-complementation
strategies. These findings in signal transduction and protein‘‘chattering’’have
beenachievedatthecellularandtissuelevelwithinvitrobioluminescentassays
andalsoinwholeorganisms,asinbioluminescenceimaging.Non-invasive‘‘in
vivo’’ bioluminescence imaging has emerged as a powerful alternative to other
imagingtechniquesandhasbeenappliedforthestudyoftumormetastasisand
progression,formonitoringbacterialandviralinfectionsandinstudiesofstem
cell homing. In recent years many xenograft and transgenic bioluminescent
animals have been created and proposed as preclinical models for drug devel-
opment and for pathophysiological studies.
Inthisbook,thehistoryandmostrecentadvancesintheapplicationsofbio-
and chemiluminescence in analytical chemistry are reported. The first part
(Basics of Chemiluminescence and Bioluminescence) reviews the historical
developmentofbio-andchemiluminescence,aswellasthefundamentsofsuch
phenomena and the most recent advancements in luminescence instrumenta-
tion. The second part (Analytical Applications of Chemiluminescence and
Bioluminescence) deals with applications of bio- and chemiluminescence in
various research fields, such as life sciences, drug discovery, diagnostics,
environment, agrofood and forensics.
I hope that this book will become a reference text not only for researchers
currently employing such detection techniques in their research activity, but
also for those approaching bio- and chemiluminescence for the first time.
Aldo Roda
Bologna, Italy
Contents
Part 1: Basics of Chemiluminescence and Bioluminescence
Chapter 1 A History of Bioluminescence and Chemiluminescence from
Ancient Times to the Present 3
Aldo Roda
1.1 Introduction 3
1.2 Ancient Era 4
1.3 Middle Ages to the Sixteenth Century 7
1.4 Seventeenth Century 9
1.5 Eighteenth Century 23
1.6 Nineteenth Century: Modern Science 25
1.7 Twentieth Century: the Brightest Era 27
1.7.1 Bio- and Chemiluminescence in the United
States and the Americas 29
1.7.2 Bio- and Chemiluminescence in Europe 38
1.7.3 Bio- and Chemiluminescence in Russia 40
1.7.4 Bio- and Chemiluminescence in Japan 41
1.7.5 Bio- and Chemiluminescence in China 41
1.8 Suggested Further Reading 41
1.9 Conclusions 43
References 43
Chapter 2 The Nature of Chemiluminescent Reactions 51
Gijsbert Zomer
2.1 Introduction 51
2.2 1,2-Dioxetane Chemiexcitation 56
2.2.1 Synthesis of 1,2-Dioxetanes 61
2.3 Peroxyoxalates 63
ChemiluminescenceandBioluminescence:Past,PresentandFuture
EditedbyAldoRoda
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2.4 Luminol 69
2.5 Acridinium and Acridine Compounds 73
2.6 Acridan Esters 81
2.7 Concluding Remarks 85
References 85
Chapter 3 Progress and Perspectives on Bioluminescence: from
Luminous Organisms to Molecular Mechanisms 91
J. Woodland Hastings
3.1 Introduction 91
3.2 Isolation of Many Different Bioluminescence Systems 92
3.2.1 Insects: Beetles and Diptera 93
3.2.2 Bacterial Luminescence 94
3.2.3 Fungi:SimilarbutnottheSameMechanismas
Bacteria 96
3.2.4 Dinoflagellates: Scintillons and Novel
Regulation by pH 97
3.2.5 Cypridinids: Luminous Ostracod Crustacea 99
3.2.6 Coelenterates: Aequorin and GFP 100
3.2.7 Pholas 101
3.3 Discussion 102
3.3.1 Milky Seas 102
3.3.2 Beetle Luciferase Structure and Color of
Emission 102
3.3.3 Evolutionary Origins and Phylogeny of
Luciferases; Lateral Gene Transfer 102
3.3.4 Luciferins: Biosynthesis and Nutritional
Transfer 103
3.3.5 Biochemical Basis for Flashing in Luminous
Organisms; the Off Rate 103
3.3.6 BasicandAppliedResearch–thePositivesand
Negatives 104
3.4 Definitions and Terms 105
3.4.1 Luciferin 105
3.4.2 Photoprotein 106
3.4.3 A More Inclusive Terminology for Luciferin
and Luciferase 107
References 107
Chapter 4 Instrumentation for Chemiluminescence and
Bioluminescence 113
Fritz Berthold, Manfred Hennecke and Ju¨rgen Wulf
4.1 Introduction 113
4.2 Luminometers 114
Contents ix
4.2.1 Detector 114
4.2.2 Reagent Injectors 118
4.2.3 Transfer Optics 119
4.2.4 Multimode Readers 119
4.2.5 High-throughput Luminometers 119
4.2.6 Tube Luminometers 119
4.2.7 Temperature Control 120
4.2.8 Relative Light Units 120
4.2.9 Sensitivity and Dynamic Range 120
4.2.10 Clinical Applications 121
4.2.11 Practical Hints 121
4.3 Imagers 122
4.3.1 Camera Principles and Types 123
4.3.2 General Camera Aspects 127
4.3.3 Transfer Optics 130
4.3.4 System Sensitivity 130
4.3.5 Sample Illumination 131
4.3.6 Sample Holder 131
4.3.7 Accessories for Dedicated Applications 132
4.3.8 In Vivo Imaging 134
4.3.9 Multimodal Imaging 135
4.3.10 Software 135
4.3.11 Plant Imager 136
References 138
Part 2: Analytical Applications of Chemiluminescence and Bioluminescence
Chapter 5 ‘‘Classical’’ Applications of Chemiluminescence and
Bioluminescence 143
Massimo Guardigli, Arne Lundin and Aldo Roda
5.1 Introduction 143
5.2 Luminol Chemiluminescence 144
5.2.1 Analytical Applications 144
5.3 Peroxyoxalate Chemiluminescence 148
5.3.1 Analytical Applications 148
5.4 Other CL Systems 149
5.5 Detection of Free Radicals by Chemiluminescence 150
5.5.1 Ultraweak Chemiluminescence 151
5.5.2 Enhanced Chemiluminescence 152
5.5.3 Study of ROS Production 154
5.6 Evaluation of Antioxidant Activity 157
5.6.1 Chemiluminescence Methods 158
5.6.2 Clinical Applications 159
5.6.3 Antioxidant Activity of Foods and Food
Derivatives 161
x Contents
5.7 Firefly Luciferase Reaction 162
5.8 Kinetics of Light Emission 164
5.9 DegradationofAdenineNucleotidesinLuminescent
Reagents 165
5.10 Reducing Contamination Problems in Assays
of ATP 166
5.11 Internal ATP Standard Technique 166
5.12 ATP Biomass Testing 169
5.12.1 ATP per Cell 169
5.12.2 Pretreatment of Samples 169
5.12.3 Extraction of ATP from Cells 170
5.12.4 Assay of ATP in Eukaryotes 172
5.12.5 Assay of ATP in Prokaryotes 173
5.13 Measurement of ATP/ADP/AMP 174
5.13.1 Energy Charge Concept 174
5.13.2 Measuring Energy Charge 175
5.14 Hygiene Control 175
5.15 Enumeration of Bacterial Cells on Filter without
Cultivation 176
5.16 Coliform Test 176
5.17 Assays of Enzymes and Metabolites 177
5.17.1 ATP Monitoring Concept 177
5.17.2 Monitoring ATP Forming Enzyme
Reactions 178
5.17.3 Monitoring Oxidative Phosphorylation
and Photophosphorylation 178
5.17.4 Monitoring ATP Degrading Enzyme
Reactions 179
5.18 Reporter Gene Assays 182
5.19 Bacterial Luciferase 182
5.19.1 Enzymatic Assays 182
5.19.2 Cell-based Tests 182
5.20 Conclusions 183
Acknowledgements 183
References 183
Chapter 6 Flow-assisted Analysis 191
Aldo Roda, Mara Mirasoli, Barbara Roda and
Pierluigi Reschiglian
6.1 Introduction 191
6.2 Fundamental and Analytical Setup 192
6.2.1 Flow Injection Analysis 192
6.2.2 Sequential Injection Analysis 193
6.2.3 Multisyringe Flow Injection Analysis and
Multicommutation in Flow Analysis 194